Activity

January 16, 2025

Extracted some more aspirin last night, but haven't been up to much otherwise. 

January 10, 2025

In a similar vein to the previous post, I found a good source of ammonium nitrate from cold packs. Since Walmart has been out for quite some time, it was nice to finally find some.

Otherwise, I haven't been up to much. Cleaned and dried some molecular sieves, but that's it. 

January 8, 2025

I managed to get a little bit of CAN prills, and I'm working on finding out what percentage calcium carbonate it is before either using it as-is, or purifying it further to get pure ammonium nitrate. 

I've also purchased some pH paper, so I can hopefully do some more pH-intensive reactions, like synthesizing aminoguanidine. As of right now, I'm running on the pieces that were left in the book once all of the strips were torn out. 

January 1, 2025

I haven't been up to too much. I recrystallized the aspirin from a couple weeks ago, and got okay yields. I extracted some thiamine mononitrate from tablets and got a 59% yield, which isn't too bad considering how I just used water and how difficult the filtration was; I had to filter out the crystals through a mesh strainer. 

I ended up not getting a super bad yield on the dimethyl oxalate, about 48%. I'm still wondering if I should continue making the compound I was planning, or go a separate direction and make another isomer. Gotta just try it out, I suppose!

December 26, 2024

I've been making some dimethyl oxalate, which I've posted a procedure on the write-ups page for. I'm hoping to use this primarily to synthesize a piperidine derivative after several steps. 

December 18, 2024

Haven't been up to much, honestly. I'm currently extracting some Walmart-brand aspirin, but nothing else otherwise.

I also haven't been able to find a good project to do, anyway. They all seem to fall apart when it comes down to toxicity or difficulty. I still would like to make some of the compounds I've talked about, though. I honestly just need to get around to buying the reagents online.

December 6, 2024

I managed to spill my methyl benzoate solution containing (presumably) benzamide, so that synthesis is over with. I did a nitration reaction with acetaminophen, though, which was successful. It depleted quite a bit of my acetaminophen stash, so I'll have to do another extraction of it. 

In terms of a site I use to buy chemicals, I'm struggling to just focus on one product. The site sells sorbitol (useful to make isosorbide), inositol (potassium rhodizonate), and pretty much all of the amino acids. 

November 21, 2024

I went to the Dollar Tree a few days ago and ended up getting some aspirin. I went ahead an extracted this, and I made some salicylic acid from it. A classic, I know. I still don't have many ideas for this. I did at least get nearly an 89% yield, which was a nice surprise. I wonder if using a more concentrated solution (I used about half as much water, but about the same HCl catalyst per mol) led to getting a higher yield, or if the enteric coating was a sizeable impurity. 

November 16, 2024

I ended up keeping the excess diethyl ether in the 500mL RBF for several days, then transferred it to a glass bottle. I'm currently distilling the heptane fraction, since it's useful in its own right. I also bought some more acetone, which I've run dangerously low on. My local grocery store has it a lot cheaper than the hardware store, which I find amusing.

I have no real plans in terms of upcoming projects. Given I just made hydrazine sulfate, I should try to make some azide salts again, which I may try if I have the nerve to try it again. If I'm going to make either, I'm planning on following the procedure laid out in Small-Scale Synthesis of Laboratory Reagents. I think, in the past, I've tried to make the hydrazine incorrectly, and apparently the way I've been doing it forms a gel that traps the hydrazine sulfate from reacting. It's no wonder why none of my past procedures have succeeded. 

November 10, 2024

I bought some starting fluid from a local store that advertised it was "50% ether", and I wanted to see if that were true. Well, after distilling, even if it wasn't exact, it was pretty close! I've managed to fill up my entire 125mL bottle, which normally never happens with starting fluid distillations, and I still have quite a bit left in the receiving flask. Needless to say, I'll be using it again if I need more diethyl ether.

I don't have any use for this ether just yet, but I'm keeping it anhydrous in case I need it for something like a Grignard reaction.

November 3, 2024

I ended up doing the hydrazine sulfate synthesis I talked about a little while ago, following the procedure from Small-Scale Synthesis of Laboratory Reagents. It seems to have worked thus far, and I got a decent amount of crystals from it, but seems to require a lot more time than the other procedure I used. It should give nearly double the yield, though, so I'm hoping it's worth it. I'm writing a procedure on it, since I have one on my classic method of hydrazine sulfate. So, I think it'll be interesting to compare.

October 31, 2024

In purifying the bottoms, it seems the lowest boiling point was about 105°C (and it still struggled to distill over), which is 15°C above that of dimethyl carbonate. While I still kept it just in case, the boiling point is much to high for it to be dimethyl carbonate, and I presume it's mainly some high-boiling alkanes. The smell was similar to that, and it was insoluble in hot lye solution (which would've hydrolyzed it to sodium carbonate and methanol). So, the dimethyl carbonate likely came over with the rest. I'll have to pack my column with BBs (I lost my glass fragments) and see if I can improve separation. Whatever remained was so non-volatile that even leaving it in the sun on a warm day didn't evaporate it fully. 

I did keep the polymer, as it was able to dissolve in acetone and may prove useful as a binder in the future.

October 26, 2024

I managed to get my hands on the paint stripper I mentioned last month. The solution is more viscous than I expected, which is indicative of some kind of soluble polymer, so I'm going to purify it before I go any further.

Just for reference, the paint stripper contains a mixture of acetone, methanol, 1,3-dioxolane, dimethyl carbonate, and alkanes (light hydro-treated petroleum distillate). The only azeotropes I could find were between acetone and methanol, and methanol and some alkanes, although data is scant for the dioxolane and dimethyl carbonate. I've run a rudimentary simulation, and it seems to show that I can separate off the volatile azeotropes before the dimethyl carbonate, given I have a good enough fractionating column. This assumes a steady-state, which batch distillation is not. Nonetheless, the lack of azeotropes in the simulation give me hope that the 15°C difference in boiling point can still give a good separation.

In practice, it supported this: I obtained a lot of low-boiling liquid below 75°C, and was left with some liquid that didn't boil over. An obvious fraction occurred at the 75°C mark (representing 1,3-dioxolane), and I was unable to push anything past after. I still need to prove this is dimethyl carbonate, but it seems unlikely to be anything else. Although, the vapor pressure is nearly double that of water at room temperature, so I'm not sure. 

Even in the scenario it's not, I'm keeping both the distillate and the bottoms, so I can still isolate the dimethyl carbonate if it distilled over—with the added benefit of a lack of polymer!

October 12, 2024

I tried to synthesize some salicylamide using urea/boric acid and the salicylic acid. I was hopeful, but the melting point of what I recovered was more consistent with sodium carbonate; that is, it didn't melt at all. I've given up hope this will work with the equipment I currently have, and I need a better thermometer.

I have been looking into some dyes I can make. I'm wondering if I can couple 2,5-dichloronitrobenzene via a Goldberg reaction. Using aniline gives Disperse Yellow 26. If I were to use phenol, though, it would give 4-chloro-2-nitrophenoxybenzene, which may have a similar color. They've used copper powder as a catalyst by just melting it with potassium phenoxide, but I'm wondering if I could do the reaction in acetonitrile with a copper (i) chloride catalyst.

September 28, 2024

I haven't gotten any sorbitol yet. But, I'm currently making some salicylic acid from aspirin I picked up at the Dollar Tree. Mainly interested in seeing the yield. 

I found a good product that has dimethyl carbonate in it: Sunnyside paint stripper. Funnily enough, Sunnyside is my brand of choice for getting some increasingly-hard-to-get chemicals, like MEK and toluene. It does have quite a bit of acetone, as well as other impurities. Thankfully, the reaction I want to do (alcoholysis) doesn't seem to be intolerant of anything but the acetone, which would polymerize under the basic conditions.

I'm planning on doing a synthesis of hydrazine sulfate using an actual procedure from Small Scale Synthesis of Laboratory Reagents, and not a NileRed video. I hope that it'll give a higher yield. The theoretical part made me realize just how lax I've been with the temperature (hydrazine seems to be very prone to decomposing to nitrogen), and is probably why I've been getting half of the yield acquired in the book.

September 20, 2024

I ended up scaling up my aluminum soap synthesis and made an entire jarful. I still need to process it some more i.e. grate it through a strainer. The synthesis seems to have been a success, though, in terms of physical characteristics (not super oily) and properties (dissolves in naphtha and increases viscosity). 

A new synthesis I'm looking into is turning sorbitol into isosorbide using sulfuric acid. I don't think it'll be too difficult, either, but could have the tendency to form tar. My end goal is to make isosorbide dinitrate, which is used to treat angina. 

August 23, 2024

I ended up making some tetramminecopper(ii) sulfate with the remaining ammonia solution from a few weeks ago, plus some ammonia on-hand to go to completion. I'm probably gonna need to make some more ammonia soon. Thankfully, I don't mind the smell.

I also distilled some Coleman fuel. Boiling point was between 72°C and 88°C, so it's some and volatile light naphtha. I don't know why the SDS said the boiling point was much higher. Roughly 90% of the distillate was below 88°C. 

August 21, 2024

I honestly haven't been up to much. Last time I was off from work, I purified some caffeine from Walmart pills using water as a solvent. I ended up crushing and drying it tonight in a toaster oven. I hope to purify by sublimation, but it may not happen. This would really only remove the FD&C Yellow 6 aluminum lake, which is making my product a light yellow.

August 10, 2024

I ended up boiling the copper (ii) nitrate solution down anyway and nearly to decomposition. I managed to scrape a small amount of powder from the crystalline mass, but the deliquescence proved too difficult to work with. I ended up drying the powder in a desiccator. I re-dissolving the crystalline mass, filtered some insoluble carbonates, and bubbled ammonia through the solution, which made some tetraamminecopper(ii) nitrate solution and crystals. With the rest of the ammonia gas, I dissolved it in some distilled water to obtain some ammonia solution.

August 9, 2024

Basic copper carbonate has been isolated and dried, while the copper (ii) nitrate is still in solution. Still haven't found a good way to isolate it, as its decomposition point is too low for un-monitored boiling. I may end up making tetraamminecopper(ii) nitrate with it via an ammonia generator, since that'll crystallize.

I'm also trying to make concentrated acetic acid later. It's one of my least favorite procedures on account that I've broken both a stir bar and thermometer during the reaction, and it yields so little. I ended up trying to add additional sulfuric acid to try to help improve solution properties, and I'm barring using a thermometer or stir bar. I ended up stopping the distillation early, as the reagents were cheap, and I only needed a little bit of acetic acid. Had I needed more, I would've gone for longer. I got about 15g, or about 68% of crude acetic acid. Seemed to smell of sulfur dioxide, which is probably from the sulfuric acid oxidizing decomposed sodium acetate. 

I was looking around a little bit and found that an interesting reaction to do could be the Meerwein arylation. Of course, once I manage to get some aniline or another aryl amine, it'll be more viable, but I could, for instance, take alpha-beta carbonyls and add phenyl groups onto them. There are some interesting compounds I could make, but I'd need to look into how to get my alkene before doing anything.

One more thing I was looking into was how similar the expectorant guaifenesin is to the muscle relaxer methocarbamol. In fact, I've looked into a synthetic pathway that should be possible to turn the former into the latter. Guaifenesin can be reacted with dimethyl carbonate in a transesterification to form a cyclic carbonate ester. Afterwards, it can be directly reacted with aqueous ammonia to form both methocarbamol and, to a lesser extent, beta-methocarbamol. On paper, it seems good, but I would need to make/purchase dimethyl carbonate, which shouldn't be that hard. I don't believe it's illegal to simply make a non-controlled medication so long as it's not for human consumption, but I could be wrong; I just think it'd be cool to make a common medication from another common medication.

August 3, 2024

Recrystallization of the paracetamol yielded nothing because I fell asleep during the isopropyl distillation and cooked it.

I recently made some copper (ii) nitrate solution from copper metal and nitric acid I wanted to get rid of. Still need to isolate it. I also made a bit of basic copper (ii) carbonate from some leftover copper. My rule of thumb is to ensure both solutions (copper (ii) salt and sodium bicarbonate) are at room temperature before mixing to get the most ideal particle size.

July 19, 2024

I tried to stir the methyl salicylate, and even added some more ammonium hydroxide solution, but it didn't decrease anything, even after adding stirring for 24 hours. I'm not sure how to proceed, honestly. I left it for another week and nothing seems to have changed. Wonder if benzoic acid fusion with urea would've been better. Just need to invest in a better thermometer that goes past 150°C.

I did end up dissolving some silica gel beads in sodium hydroxide solution, then acidifying and freezing for a week. I thawed it overnight, and was left with some nice gel-like suspension. I've filtered off the silica, washed it with some sodium carbonate solution, and I'm currently drying it in a toaster oven. 

I decided to isolate some paracetamol from pills, which I'm currently working on solvent recovery from nearly 91% isopropyl alcohol. 

July 8, 2024

Benzoic acid recrystallization only yielded 25g of crystals, so I'm at a loss where it all went. I'm just glad I got some amount recovered. Sodium benzoate is cheap, though, so I'm unperturbed.

July 3, 2024

I've recovered some crude benzoic acid after working up the solution I isolated the methyl benzoate from, and I'm currently recrystallizing it using a mixed-solvent system—methanol and water.  There was quite a bit of crude, so I believe all losses were from the reaction not going nearly to completion. I'll update on my final recovery, but I'm getting a lot of needle-like crystals right now. 

The benzamide solution hasn't changed much over the past few days. I may want to stir it or add some methanol due to the biphasic mixture.

June 29, 2024

The workup on the methyl benzoate was rough. The reaction didn't come close to completion, and I got maybe a 10% yield. I attribute the loss to the reaction not going to completion, despite 8 hours of reflux. I'm working on recovering the benzoic acid, so the synthesis won't have been a complete waste. I'm also recovering the methanol. I've already started the benzamide synthesis with the methyl benzoate I recovered. Hopefully it produces the benzamide I'm expecting.

June 28, 2024

I've made some benzoic acid from the remainder of the sodium benzoate bought years ago, and I'm currently making methyl benzoate with it. I'm planning on doing the aforementioned ammonolysis over the course of the upcoming week. Hopefully, I can get some aniline after a Hofmann degradation. It helps when the aniline isn't prone to just turning to nitrogen like with hydrazine. 

June 27, 2024

I'm trying to think of reactions I can do with materials on-hand, which also won't poison me. 

I might make some benzamide, but if it's anything similar to the salicylamide, I'm not optimistic. Rather than melt with urea, though, I might make methyl benzoate, then perform an ammonolysis with aqueous ammonia. Apparently, letting it sit for several days will allow it to react in high yields. Might be interesting to try that method with salicylic acid esters as well. I should also try to make ammonia if I'm using all of it for ammonolysis reactions. 

Like I said several months ago, I still need a use for my oxalic acid. I may make formic acid, which I will store as an aqueous solution to make ammonium formate in-situ for Leuckart reactions. Alternatively, a Eschweiler-Clark reaction. Another reaction I could do is to make the personally-infamous acetic acid from sodium acetate, which I used all of in a different reaction and broke a thermometer during my last synthesis. I need to make some more, anyway, since I'm out.

Another thing I could do is a caffeine extraction, followed by purification by sublimation. I think the yield will be quite low, but it makes use of some caffeine tablets I have. It'll at least be a fun non-toxic synthesis. 

I guess we'll see what all I do tomorrow and into the rest of the weekend. 

June 23, 2024

I'm thinking about doing some azo coupling reactions lately. I have an idea of two aryl amines: aniline and toluidine. The former, I would have to synthesize from benzoic acid via benzamide and Hoffman degradation, and the latter I'd have to make from toluene via nitration and Bechamp reduction. I'm leaning towards the former because the Bechamp reduction workup is annoying, as it tends to foam due to iron oxides. Toxicity might be an issue, though, and I probably wouldn't dye a T-shirt unless I washed it a few times and the dye has been used industrially as a clothing dye. 

June 15, 2024

I've been making some dinitro-paracetamol, and its derivative, 2-amino-4,6-dinitrophenol. For the former, I used some 87% sulfuric acid, and it didn't precipitate during the nitration. It gave me some concern, but I got about 15g of damp product, so it must've worked just as well as 93%, but without the pain of stirring being seized. The latter synthesis was identical to previous procedures in terms of reaction timeline. So, it confirmed that, despite the differences in the nitration, it worked just as well.  

June 14, 2024

I ended up doing a melting point test with the bulk trinitrophenol I have. It melted at about 115°C, which is a little bit far from the ideal melting point of 121.8°C. So, I believe it's slightly contaminated with dinitrophenol. This is at least consistent with prior syntheses, in which the main product was dinitrophenol. I'm not sure why many procedures seem to think this product will be 100% pure, since the mechanism of nitration has dinitrophenol as an intermediate, and sheer electron density shows it isn't the most prone to nitration.

June 8, 2024

I haven't been up to very much. I also don't have much planned. I'm going to look into what to do with the remaining nitric acid I have, since it's a pain to keep having to avoid using my 500mL RBF to store nitric acid with.

Something I want to do is to make hydrazine sulfate via the procedure outlined in Small Scale Synthesis of Laboratory Reagents. The procedure is different than ones I've done previously, and gives over 60% yield. I don't have the capabilities yet (it requires an addition funnel), but I want to see how wrong I've been doing it the past several years (thanks NileRed).

June 6, 2024

I ended up making some trinitrophenol with the salicylic acid and some of my 87% sulfuric acid. I ended up with a 43% yield. There are many analyses I could do regarding reaction time, temperature, and reagent ratios, as varying them can drastically alter the quality of the product.

I also decided to discard the solution from the salicylamide synthesis, since I truly think it didn't work (plus the oil contamination rendered the product poor). 

June 1, 2024

I tried to evaporate the perchloroethylene/hexachlorocyclopropane solution outside with heating, but it started smelling faintly chlorine-like and I ended up abandoning the evaporation for fears of phosgene exposure.  The solution remained a slight-yellow color afterwards, which strikes me as something decomposing.

I did make some salicylic acid from aspirin today (a shocker to no-one), which I don't have a use for yet. I also distilled nearly 500mL of HEET methanol to remove any oils. 

May 25, 2024

I was able to recover 36.6g of what I believe to be ammonium methyl sulfate, which is a 57% yield. The procedure I was following got a 75%, so it's not too far off. Poor yield is probably because I washed it with methanol after filtering. I still need to figure out what I'm gonna use it for. 

I also got around to the hexachlorocyclopropane synthesis. It wasn't exactly textbook (my magnetic stirring seized, and I had to stir it by hand every so often), but I'm hoping to get some amount of product recovered. It smells different than it did initially, so it's a good sign. 

May 24, 2024

I've found even more proof that the sulfamic acid reaction doesn't work without a catalyst with ethanol. I noticed a slight ethereal smell, which is probably trace diethyl ether. I ended up pouring it down the drain. I'm currently making ammonium methyl sulfate this time, since it's proven to work from online sources. I'm predicting roughly 50g of ammonium methyl sulfate.

I've also realized that I have quite a few chemicals that I have a decent amount of, but no overt use. I should really try to do something with them. 

May 18, 2024

I don't believe I got any yield from that synthesis. I tried to recrystallize the crude material from methanol, but it didn't dissolve when it theoretically should've based on a paper I found. I've also read overshooting the temperature is detrimental to yield, and considering my lack of temperature control and the fact the oil was at its smoke point, that explains it. Also, the flask tipped over and got oil in it, which didn't help. I'm unsure if I'll retry the synthesis without proper temperature control.

I've also tried to synthesize ethyl ammonium sulfate from ethanol and sulfamic acid. I've read this might produce ethylene and ammonium sulfate, so I'm not expecting too much (despite having done so hours prior). I'll see if I get a product, but the hydrolysis reaction might only work with methanol. I'll update with a yield if I end up getting anything. 

May 15, 2024

I finally managed to get some time to do some chemistry. I'm synthesizing some salicylamide from salicylic acid, urea, and boric acid as a catalyst, using an oil bath. I'm expecting an 89% yield, but probably lower due to lack of temperature control; the oil bath should keep it below 204°C. I'll update on a yield once I'm done with the synthesis.

May 5, 2024

With the 10% bleach, I did make some chloroform after a few hours of the bleach in the freezer. It heated up immensely as I shook it after adding the acetone, and I had to vent the gas increase to prevent any blowout. I added excess acetone, and got a preliminary 22% yield. I blame the high temperature and the fact I didn't actively cool it. This yield further decreased to 13% after refluxing with sulfuric acid and distilling, though that's probably because I stopped the distillation a little bit early. Very unfortunate.

I poured about 200mL of bleach out to make the chloroform, and I decided to make some potassium chlorate with it. I ended up getting 4.9g, which is a really good 51% recovery. Chances are it's contaminated with a bit of sodium chloride, but even still, the yield is good. 

May 3, 2024

The residue didn't dissolve further, so I had to process it. Interestingly, when I precipitated anything that dissolved with sodium hydroxide solution, a lot precipitated, so I probably should've simply decanted it off. I ended up making some invert sugar and reduced the formed silver oxide to silver metal. I had tested the invert sugar with Benedict's solution and found it to be viable. I was then able to rapidly dissolve the silver to silver nitrate with a few mLs of the 56% nitric acid, and had to filter off a small amount of AgCl from using tap-water absentmindedly (some of which ended up in the resulting solution anyway). This silver nitrate solution should last for a decent amount of time, though, since I rarely use it.

Also, I got some 10% bleach solution lately as pool sanitizer, and I'm letting it cool in a freezer before making chloroform with a gallon of it. I'm hoping for at least 100mL of chloroform. I'm debating if I should add extra acetone and just reflux and distill over sulfuric acid afterwards. I still don't know what I'm going to do with the other 3 gallons, but hydrazine sulfate via Hofmann degradation of urea comes to mind. 

April 28, 2024

I made a bit of a mistake and left my silver nitrate beaker outside, and it got knocked over. Wanting to see how much silver I had, I precipitated the silver out as the oxide and got about 1.6g from both that and some old silver nitrate solution I had already. I'm not too sure if it spilled or not. I tried to redissolve the silver oxide, but it just changed color from dark gray to pink-ish and didn't dissolve, despite adding something like 5 times more nitric acid than necessary.  I'm probably going to let it sit for a while until I get a chance to process it further.

April 27, 2024

I tried my hand at a nitration reaction using the 56% nitric acid, and my yield was poorer than with potassium nitrate, and the solution still was unable to be stirred magnetically. So, I squandered about half of the nitric acid I made. But, I made it for that reaction specifically as a test run. 

I did end up making some silver nitrate solution with a couple mLs of the 56% nitric acid. But, I still need to find a use for the rest of it. 

In better news, I finally isolated the lysine hydrochloride crystals from a few weeks ago, bringing my total recovery to 65 grams. I'll still consider boiling it down further to get more lysine out, but I'm running out of desire to do so. I have no real use for the lysine, and it only cost $3. I'll give it some thought as to whether or not I ditch the rest of the solution. 

April 26, 2024

I've finally been doing some deep research into organic synthesis these past few days. There's a compound called hexachlorocyclopropane that hasn't been adequately characterized in the home lab. In fact, the only thing that shows the procedure I'm planning on using is even viable is from 1964. I'm planning on preparing it by doing a [1+2] cycloaddition of dichlorocarbene (formed from chloroform and potassium hydroxide) with tetrachloroethylene. Yield is apparently really low—about 4.5%—but for chemicals I can obtain from materials at my local superstore, it seems worth it, especially to only prove viability. The only downside is the potential for carbon monoxide generation (the main decomposition route for un-reacted dichlorocarbene in basic conditions), so I need to be careful and only do it outside. I have no real use for the hexachlorocyclopropane, otherwise.

April 20, 2024

I made some nitric acid from 87% sulfuric acid and potassium nitrate, which took about 3 hours to distill. I added some water to make it azeotropic or lower, so the end concentration was about 56% w/w and the overall yield was about 95.1%. I tried something new by purging it with air for a half hour to remove dissolved nitrogen dioxide, and it seemed to work well: the strong-yellow color turned to a crystal-clear.  Yield loss was negligible, so I'll likely do it again in the future.

April 14, 2024

I did some more work-up with the isopropyl salicylate, namely increase the pH with sodium bicarbonate and extracted the oil with heptane. I didn't get much isopropyl salicylate—maybe 1mL or so. It surprised me that a small change in sterics could affect the esterification so much, and because the paper got a much higher yield, it was a bit disappointing. But, the small amount was still enough to characterize it.  The smell is like glossy magazines when dilute, but the green mint-like smell comes out when concentrated. 

I've also been trying to get some more lysine hydrochloride from my solution, which I was successful in doing using isopropyl alcohol. This is insoluble in the lysine solution, so it seems to just pull water from it in a biphasic mixture. After mixing, the solution again supersaturated, and a seed crystal was able to  crystallize everything. I still need to get a percent recovery to see how effective it is. 

March 23, 2024

I was able to distill off the isopropyl alcohol, but was left with a lot of salicylic acid, which formed a supersaturated solution after cooling and crashed out upon shaking. Workup yielded very little oil, but I'm still going to extract what little I have. From preliminary tests, the smell is actually somewhat minty when concentrated. Hard to describe, but more "green" and spearmint-y than methyl salicylate, which is extremely peppermint-y. 

While performing the fractional distillation, I noticed a hole in my Vigreux column from where a "spire" broke off. I'm not exactly sure how I'm going to fix it aside from "band-aid" modifications e.g. plugging it with foil, but I need to be careful going forward so I don't let anything dangerous leak. 

March 22, 2024

I've finished my 8-hour isopropyl salicylate reflux. Work-up will probably occur tomorrow. Although the paper says they evaporated the excess isopropyl alcohol via vacuum (presumably roto-vap), I'm going to try a fractional distillation, since even a couple theoretical plates should be enough to separate the isopropyl alcohol and isopropyl salicylate. I should be left with a goo or oil of some kind.

March 20, 2024

I've recently been making some salicylic acid from aspirin. Repeat synthesis, I know, but I plan on making isopropyl salicylate with it. I've tried to do this synthesis in the past, but failed, and I think it's because I tried to hand-wave it. I have an actual procedure now, and want to try it out. Isopropyl salicylate, I've found, smells different than methyl salicylate. The latter smells heavily of wintergreen, but the former smells almost like a glossy magazine when dilute. I want to see if this smell is accurate when its concentrated form, or if it smells minty.

In other news, I've separated the lysine hydrochloride crystals, and recovered about 35g of the 150g I put in. I still have the mother liquor, and plan on boiling it down further to obtain more lysine hydrochloride crystals. I did make a small amount of cadaverine just to see what it smells like using sodium carbonate and a blowtorch. Initially, it smelled quite fishy, but quickly smelled like burning polyester. I think this was due to concentration, and I've read cadaverine smells like epoxy. Nonetheless, I still don't have a use for this lysine. 

March 13, 2024

I shifted from aluminum soaps (finally) and extracted some lysine hydrochloride from discounted supplement pills. Despite the high solubility (nearly 1:1 by mass with water), I've managed to grow quite large crystals by increasing my scale (I used 150 1000mg pills). They were slow to crystallize, so I've been letting the solution sit for several days after initially crystallizing to make sure it's all out. I have no idea what I'm going to do with the lysine produced, since it's a bit of a trash amino acid due to its charged side-chain. I could make crude cadaverine, but only by thermal decarboxylation (and not by catalytic decarboxylation, like e.g. phenylalanine). Otherwise, I have no idea what to do with it, much like the glutamic acid I have. 

I'd like to do some more interesting reactions with amino acids, namely the catalytic decarboxylation to substituted amines. I just need to obtain ones whose side-chains fit the procedure better.

February 28, 2024

I retried the acid hydrolysis with olive oil and, thinking it was impervious to failing, I didn't feel the need to reflux the acids in potassium hydroxide for long enough. So, it failed spectacularly; the only thing I got was fatty acids in an aluminum hydroxide gel, which leaked out and shrank the pieces over the course of a few days. Basically, I killed some time to learn not to be overconfident.

February 16, 2024

The acid hydrolysis worked wonders, and I was able to make the aluminum salts of fatty acids derived from vegetable shortening. I believe that, for fatty acids, acid hydrolysis is superior than base hydrolysis (unlike other compounds). This is because the viscosity of solution skyrockets with base hydrolysis, but stays more or less the same with acid hydrolysis due to the hydrolysis products differing in solubility i.e. the base hydrolysis makes fatty acid salts. Even just after cooling from a rolling boiling, the viscosity of a 0.77M solution was that of room-temperature hand soap. So, refluxing during the acid hydrolysis is child's play, and it can sit for hours un-monitored.

Going forward, using an acid hydrolysis for making fatty acid salts will be implemented into my procedure. Although I haven't done any kind of percent conversion analysis, the results from making aluminum salts speaks for itself (all procedures using acid hydrolysis as a first step resulted in textbook syntheses), and neutralizing the acids with potassium hydroxide and the heating required to dissolve them will hydrolyze any trace triglycerides. 

February 10, 2024

I've retried the synthesis I did using coconut oil, but it didn't work. So, I don't have a working procedure at the moment. My theory is that I didn't hydrolyze the oil enough, same with the olive oil. I either need to reflux over base/acid for hours, or do what I did the first time and do an acid hydrolysis, then base hydrolysis. Cost leans me towards the former.

I'm currently trying to hydrolyze the fats in vegetable shortening using dilute sulfuric acid. I'll need to do a basification anyway for the aluminum soap synthesis, so a pre-treatment with acid will be better than a base hydrolysis, then acidification, then basification.

January 30, 2024

Since the last entry, I've successfully made aluminum salts from fatty acids derived from coconut oil using alum. Unfortunately for me, the capric and caprylic acids that comprise about 15% of the acids smell quite bad. The aluminum salts are hard to get off of glassware without acidification as well, as they aren't too soluble in water, so I get to relive it every time I clean. I tried to do the same synthesis with olive oil fatty acids, which smell a lot better (similar to vegetable oil), but to no avail. 

January 18, 2024

In the past couple weeks, I distilled the HEET and purified some other methanol I recovered from a recrystallization. I've been making some fatty acids from oils via base hydrolysis, followed by acidifcation; I had tried acid hydrolysis, but wasn't comfortable with the possibility of incomplete hydrolysis. I plan on making some aluminum soaps from them.

January 3, 2024

Happy New Year! I haven't been doing much. I got some sodium hydroxide and some more methanol in the form of HEET, which I need to purify. I've been meaning to do that, plus the rest of my methanol, but, because it'll be a day's worth of work, and it's been very cold lately, I haven't gotten the chance to do it. 

As of right now, my plan sometime soon is to make a small amount of formic acid with my oxalic acid I bought over 5 months ago, but I have to finalize a storage bottle for it, as well as mitigating any carbon monoxide formed during the synthesis and purification. 

December 3, 2023

Well, I was correct! I got the nitromethane in the mail and, after many long hours of distilling, I got pure nitromethane (plus a bunch of methanol/nitromethane azeotrope), and 4 times the amount the video got. It just goes to show that chemists (and especially hobby chemists) really need to understand the fundamentals of batch distillation and why theoretical plates are necessary to get good separation, rather than just hand-waving it. I'm definitely guilty of doing this in the past, but my fractional column packed with tempered glass has rapidly become my favorite piece of lab equipment, and is crucial for separating volatile liquids.

November 29, 2023

The only thing I've done lately has been extracting polyisobutylene from fly traps using VM&P naphtha and acetone, which I recovered both of. 

I also purchased some 20% nitromethane racing fuel that I plan on purifying when it gets here. A YouTube video got about 15mL out of a theoretical 90mL, which is atrocious. I believe their setup allowed for too much nitromethane to come over with the methanol/nitromethane azeotrope, as they let anything below 70°C over and didn't use enough theoretical plates, which they had deemed "unnecessary". It seems incredibly necessary based on other separations I've done, but I'll do the purification and get a yield before I talk smack.

November 12, 2023

I managed to procure some tetrachloroethylene—about 300mL—from a local Autozone recently. I've distilled it to remove any solid impurities or trace oils. I'm not too sure what I'm going to do with it, but I had wanted to make hexachloroethane. 

November 3, 2023

Like last time, I haven't been doing a whole lot chemistry-wise. I recrystallized some copper (ii) sulfate that had made in bigger crystals (the new product is more similar to grains of sand). I also distilled some used isopropyl alcohol, then re-distilled using a packed fractionating column.

Tonight, I extracted some acetylsalicylic acid from aspirin using acetone as a solvent, distilled the acetone off, then hydrolyzed it to salicylic acid, which is still crystallizing. I still need to filter it off and recrystallize it.

October 24, 2023

I haven't been doing a whole lot chemistry-wise. I did a small-scale caffeine extraction using citric acid to increase the solubility in water, and I did another hydrazine sulfate synthesis (however, I misplaced the reaction mixture, so I didn't get anything from it). 

October 8, 2023

I was successful in making 68% nitric acid from the 86.5% sulfuric acid. Not sure my overall yield, since I also used the opportunity to purify some old nitric acid.  I don't have any pressing uses for it, but I have about 100mL of it. I made some tetraamminecopper(ii) nitrate with the residual nitric acid in the distilling flask after the final distillation, which is a vibrant indigo color—typical of tetraamminecopper(ii) salts.

I also had an accident whereby I added some basic copper (ii) carbonate to a container of basic nickel (ii) carbonate, and had to remedy it. I had to dissolve it in hydrochloric acid, then reduce it to the metal. I'm unsure what I plan on doing with the contaminated nickel, but I could either do a physical separation via a magnet, or chemical by letting the copper oxidize, then using dilute hydrochloric acid.

September 30, 2023

I was able to recover most of the toluene I used via distillation, and even recovered a small amount of sulfur in the process. I also was able to remove the brown impurity in the other crystals by doing several water-washings, since the impurity easily formed a suspension. I was left with some beautiful, yellow crystals of sulfur. 

I also obtained some 86% sulfuric acid from a local store at half the cost of 93%. While I don't really plan on concentrating it further, I think it has valuable use as a weaker source of sulfuric acid. For instance, it'd be very useful in making nitric acid and hydrazine sulfate, which tend to waste the "good" 93% sulfuric acid.

September 27, 2023

I've decided that refining sulfur from commercial 90% sulfur dust was a good project, since it lets me purify both sulfur and toluene at the same time. I've already obtained some nice sulfur crystals, but they still have some impurity in them, as shown by a brown layer coating the tops of the crystals. Whether I remove this impurity by another recrystallization or manual separation is a different story, but I'll end up deciding tomorrow.

September 23, 2023

I haven't been doing a whole lot. I distilled some methanol to liberate it from any potential oil it was contaminated with (considering it was a car anti-freeze), which I always do with commercial methanol. I also transferred the nitrophenols to a plastic bottle for storage, and cleaned the boiling flask for actual use. I'm letting any solids settle out, but I have no idea if I'm going to use this or not.

I have no solid plans at the moment, but I'll update with whatever I end up deciding to do.

September 15, 2023

Welp, I broke a 150mL Erlenmeyer flask while washing it the other day. Guess I'm just glad it wasn't costly, but it annoyed me nonetheless, especially considering this is 4 in about a month. Otherwise, I tried a phenol nitration, which made me practically irate during the workup involving a steam-distillation; it was all working fine (if you can call 10 drips/hr fine) until the boiling flask foamed over, which ruined everything. So, I gave up temporarily, and I'm storing the boiling flask with the contents inside. I also tried a hydrolysis of the diisononyl phthalate from gloves, which resulted in a white precipitate that mostly eluded capture by a coffee filter. The rest I dried; I have reason to believe this is not phthalic acid, as it bears too much similarity to a previous attempt at synthesis that failed. I'll update with news only if it ends up being phthalic acid. Other than that, I haven't really done anything.

September 5, 2023

I've since purified my diisononyl phthalate by simply heating in a beaker to about 105°C, then cooling back down; this removes both water and residual isopropyl alcohol. I got 39.9g, corresponding to about 1.6g of plasticizer per glove. Decent yield, in my opinion. It's currently sitting in a flask. 

I've also attempted to make the biodiesel from vegetable oil. Unfortunately, universal karma decided that I was undeserving of this synthesis, and I broke my 250mL separatory funnel and my 1L round-bottom flask upon pouring the biodiesel into it for separation. Guess it should inspire me to get more glassware, but it still feels like two knives to the chest, especially since I took all precautions to prevent such a thing from happening (filled the 1L flask about half-full with water before putting the sep funnel on top). Oh well. 

September 3, 2023

In the past few days, I've done a few things. First, I did a transesterification of castor oil with methanol, forming a biodiesel comprised mainly of methyl ricinoleate. Density was around 0.89g/mL, which is in the range of biodiesels and inconsistent with castor oil. I also extracted the plasticizer diisononyl phthalate from Equate vinyl gloves, like I did several months ago. I've done it on a larger scale, while using less isopropyl alcohol. I'm hoping to make phthalic acid, but it depends on how confident I feel about the saponification. 

Otherwise, I haven't been doing anything else, really. I plan to do a write-up on my biodiesel synthesis very soon, though.

September 1, 2023

I haven't been doing a lot since the last time I posted. I've made some more hydrazine sulfate, using 31% hydrochloric acid to neutralize the sodium hydroxide and sodium bicarbonate, then using the 50% sulfuric acid to precipitate the sulfate. I also used a mixed solvent system in the recrystallization, using a mixture of isopropyl alcohol and water.

In doing so, I'm also recovering the isopropyl alcohol I've had in my "redistill" container, using sodium chloride to separate it out from most water-soluble stuff, then a phase-separation, then distillation. I ended up with probably 80%+ isopropanol (since my still-head temperature creeped up to around 93°C before I took it off of the hotplate), which is alright for my purposes. 

In regards to the ferric ammonium citrate, I turned it into a solution and made a cuprotype with it (contact print with 120 film negative; sunlight as a UV source). Although it's somewhat underexposed, it's still very clear what's being depicted, and has a fair amount of details. So, I definitely made ferric ammonium citrate, and the process resulted in a fairly good product.

August 12, 2023

So, I've evaporated down most of the ferric ammonium citrate solution, and hope to turn it into a viable solution soon, since it doesn't seem as though it's going to crystallize. I've also attempted a Barbier reaction with zinc powder, which was mainly unsuccessful, as well as an attempt to make a nickel (ii) complex with an o-aminophenol derivative, which also failed. I was at least successful with both a paracetamol extraction, as well as a salicylic acid synthesis, which stemmed from an acetylsalicylic acid extraction. 

August 5, 2023

I've gotten back into the swing of things, and have been aspiring to do more stuff. So, in the past week, I've been up to more than usual. I've been making ferric ammonium citrate completely from scratch, and after an initial failure (a base precipitation yielded iron (ii, iii) oxide instead of ferric hydroxide), I'm having good results with my second procedure. I attribute the failure to an incomplete oxidation of the iron (ii) chloride I synthesized from steel wool. The successful procedure has had a lot of very small iron (iii) oxide particles, so it's taken a while to let everything settle. But, I've obtained a somewhat-clear olive-green liquid, which is consistent with ferric ammonium citrate; I'm currently evaporating this down. 

I've also isolated presumably-pure tetrachloroethylene from that fabric cleaner from a couple months ago. After a water wash to remove the other compounds (2-methoxyethanol and n-methylpyrrolidone) and a decent amount of sodium chloride to facilitate layer separation, followed by a distillation, I've gotten a bit more than 60mL of slightly-wet tetrachloroethylene. From what I've gleaned, it smells similar to chloroform, but very slightly different in a way I can't describe. I'm not sure what all I hope to do with it, but it's nice to have on-hand, especially when it's getting phased out as of late. Possible syntheses include hexachloropropene and hexachloroethane.

In terms of chemicals I've purchased, I got some oxalic acid dihydrate from a hardware store recently. I don't have anything immediate that I have planned with it, but I hope to make esters (namely the dimethyl ester (assuming its not as hygroscopic/moisture-sensitive as some people have reported), and some metal salts/complexes. Also, it can be used to make small amounts of formic acid, which is useful for organic reductions like the Leuckart reaction.

July 19, 2023

I've finally gotten some nice and smooth copper (ii) sulfate crystals after just under a month of growing. Pretty proud of them, especially since I dropped one upon re-positioning, which shattered a corner. I'm now in the process of reclaiming the copper (ii) sulfate from solution by boiling, as well as painting the crystals with clear nail polish to protect them from efflorescence. I've also recently attempted a distillation of orange peels to yield its essential oil, of which the distillate smells similar to Froot Loops cereal. I still need to do a solvent extraction to isolate the oil, but it's on the backburner at the moment (much like the phenol distillate). 

July 8, 2023

Haven't been doing much of anything, honestly. I made some impure phenol a little bit ago, that I'm storing as just the reaction distillate (phenol is a clear liquid that's phase-separated from the aqueous distillate; the fact it's still a liquid shows it's quite impure).  I also made some potassium chlorate, both from some really old calcium hypochlorite I was getting rid of, and some 7.5% bleach. For the latter, recovery was around 21%; I was unable to calculate a yield for the fomer, since the calcium hypochlorite had absorbed so much water that the driest part was a paste.

Also, I started growing crystals a couple weeks ago. I decided to start with copper (ii) sulfate, as I had a lot, and it's an easy compound to start growing crystals with. I've been using the evaporation technique with fishing line tied onto some small seed crystals. 

June 6, 2023

So far, I've been doing mundane things. I reduced the chromate back to chromium(iii) via adding ethanol, then recovered it as chromium (iii) hydroxide. This way, I don't have to deal with the sodium, nor do I have to deal with potent carcinogens. I also got 4lbs of fertilizer-grade ammonium sulfate, which I spent the past day crystallizing half a pound of after removing the dirt and pebbles. I was able to get a nearly-white crystalline powder. I'm not sure what all I want to do with it, but making some alums and Tutton's salts seem to be a good place to start, especially if I want to start crystal growing as a long-term project.

June 1, 2023

After a bit of a break, I was able to turn the iron and chromium hydroxide mixture to a dichromate solution (albeit with a lot of sodium contamination). I also finished synthesizing salicylic acid from the aspirin and got around an 80% yield without a recrystallization, which is honestly not bad. This comes out to about 40g of salicylic acid, which should produce roughly 13.6g of phenol. I haven't felt the urge to actually do this reaction yet, as, for the same reason as the nicotinic acid purification or inositol isolation, it seems very tedious. Perhaps, because I have so much free time now, I feel no urgency to go through the tediousness. My time is worth something, after all. 

I also attempted a paracetamol extraction from the Dollar Store. I was only partially successful due to the binders and other inactive ingredients. Just a pain overall, and it's been on the backburner in my fridge for over a week. I'm still debating whether or not to just ditch it, or just do a continuous recrystallization of the filter cake to get some pure paracetamol. 

I did manage to get my hands on some old fabric cleaner, which contains perchloroethylene (tetrachloroethylene), as well as some other impurities. My goal is to isolate this perchloroethylene and either chlorinate it to hexachloroethane, or to react it with chloroform to make heptachloropropane, which I can subsequently make hexachloropropene from. 

Also, I'm planning on getting some electrodes from eBay to re-start my potassium chlorate cell, which has been inactive for over a year now. Considering that potassium chloride is now quite easy to get from Walmart, I'm losing money not buying them. But, I still have to both research electrodes, and weigh other purchases, which include a vacuum pump, new glassware, some chemicals e.g. sulfur and cobalt(ii) carbonate, some electronics, and a low-pressure sodium lamp.

May 19, 2023

I was able to to boil down and filter off some more of the presumed nicotinic acid from the reaction mixture, bringing my filter cakes up to 3. I also got some scouring pads from the Dollar Store, which I thought would be similar to steel wool in terms of their composition. But, it turns out that they're stainless steel, so I now have a mixture of iron (ii) and chromium (iii) to separate. I used two to make the sulfate salts, which I'm crystallizing, and one to make the chloride salts, which I've precipitated as the respective hydroxides. I'm currently drying these in a toaster oven to get the dry compounds (and hopefully oxidize the iron (ii) hydroxide to iron (iii) oxide). As well as that, I'm working on the biggest aspirin extraction I've done, using 200 325mg pills. I'm hoping to eventually make a bunch of phenol, which I can then nitrate; the o-nitrophenol is what I'm after, which should be a higher yield than the p-nitrophenol. The o-nitrophenol can hopefully be reduced to o-aminophenol, which is really what I'm after (assuming it behaves a lot nicer than p-aminophenol in air).

May 17, 2023

I was able to acquire some vitamin B3 in the form of inositol hexanicotinate. While this would be a downside to some, I'm actually after both the nicotinic acid and inositol. I've hydrolyzed this compound and have started the isolation process. The only plan for the nicotinic acid is to make pyridine via catalytic decarboxylation (which I have no immediate use for), while I plan on using the inositol to make the lead-detecting compound potassium rhodizonate, as well as potentially the potassium tetrahydroxyquinone derivative. I also got some more aspirin. I would like to make some more phenol and potentially nitrate it, but I'm unsure as of yet. I'll update on how the isolation of the vitamin B3 components goes.

May 13, 2023

Now that I'm finally at home for a while post-college, I can do some cool chemistry. So far, I've made some ferrous sulfate from steel wool ,and purified my old ferrous sulfate, which yielded some excellent ferrous sulfate crystals. I tried to make some ferric sulfate as well with the waste, followed by depleting my stash of 10% ammonia trying to make ferric ammonium sulfate. I got a paste with the former, and some crystals with the latter, that I later failed to recrystallized and ditched. Otherwise, I've only made some more salicylic acid. I'm unsure what all I'm going to do in general, but I plan on updating more often, or, at least, when I get around to doing stuff. 

April 10, 2023

Been a little while, and I haven't been up to a whole lot up until the past few days. I was able to procure some 12.5% pool chlorinating bleach, which I made hydrazine sulfate with twice. I used a different workup between the two, with the first using a direct acid workup with recrystallization, and the second using the methyl ethyl ketazine route; the former yielded about 3 times as much than the latter. I also made some more salicylic acid from dollar store aspirin, and recrystallized my stockpile of salicylic acid due to a pervasive isopropyl salicylate smell. 

I also produced some calcium cyanamide by calcination of calcium cyanate in a metal pipe. It seems to have worked well; adding some of the white powder to an ammoniacal silver nitrate solution yielded a yellow precipitate, consistent with cyanamide. I also did a cyanide test by adding the solid a ferrous sulfate solution, followed by acidification. There was no Prussian blue formation, so I believe I was able to wash out any sodium contamination to prevent sodium cyanide formation. It's possible that there was either too little sodium cyanide to be detected, residual sodium remained as the chloride, or I did the test wrong. 

In regards to the white precipitate from last post, upon heating with a blowtorch, an amount of the solid I obtained from the previous procedure produced a white smoke and deposited a white residue on a watchglass. Despite this, both a sublimation test and a failed copper phthalocyanine synthesis showed that there was only trace phthalic acid; I'm not sure where all of the phthalic acid went, though, considering I was able to characterize (by smell) and store the isononyl alcohol. I also obtained some 12% hydrogen peroxide from the hardware store, which should be useful for oxidation reactions in the future.

In terms of things I've been looking into, I had seen a procedure regarding oxidation of amines to oximes and oximes to nitro compounds, which can be used to make aldehydes via the Nef reaction. I'm interested in seeing if this is viable for phenethylamine to produce phenylacetaldehyde, which can possibly form phenelzine via reductive amination/"hydrazination". But, this might be a bit of a pain compared to the styrene/2-phenethyl bromide pathway. 

January 10, 2023

I had a few weeks to do some chemistry over the holidays, and I was able to do a few interesting things. I distilled some ethanol from a gallon of RV antifreeze, and managed to collect nearly 500mL of 95% ethanol. I also was able to procure some vinyl gloves from Walmart that had diisononyl phthalate (DINP) as the plasticizer. I was able to extract this by boiling with 91% isopropyl alcohol, which left very brittle pieces of vinyl plastic. A base hydrolysis procedure with acid workup to get the phthalic acid only resulted in an obnoxious smell of isononyl alcohol and a white precipitate upon acidification that did not dissolve in 400mL of boiling water. As a result, I'm unsure if this is phthalic acid, or just an impurity; I was unable to do a sublimation test to say for certain. I plan on redoing this procedure at a later date to obain phthalic acid, as well as using the near-pure DINP to plasticizer other materials. I hope to do a few things with the phthalic acid, including synthesizing luminol and copper phthalocyanine.

One other synthesis I did was synthesizing a copper(i) chloride/p-benzoquinone complex by mixing copper(ii) chloride, hydroquinone, and ammonium chloride, followed by adding a concentrated sodium hydroxide solution. The complex seemed to oxidize too fast in air to be isolated (or, perhaps, some of the ratios were off), but beautiful red crystals were formed in the reaction mixture.

November 15, 2022

The past weekend, I was pretty productive. Produced isopropyl nitrite using 91% isopropanol, 31% hydrochloric acid, and sodium nitrite, and I distilled it for the first time. It was probably the fastest distillation I've ever done, considering I was only distilling around 15mL and the boiling point is 40°C; I don't really have any plan on what to use it for.

Finally, I also did a somewhat-interesting purification of some impure 2,5-dichloroaniline I had stored. To do this, I formed the trinitrophenolate salt of 2,5-dichloroaniline, which is reported as a good way to purify primary, secondary, and aryl amines. I purified this by evaporating the solvent off, crystallizing, re-dissolving and separating off some red impurity that precipitated out. To work this now-orange solution up, I added it to some hot sodium hydroxide solution with some toluene on top. This way, the sodium trinitrophenolate could stay in the water layer and the freebase 2,5-dichloraniline moved into the toluene layer. After some washing, I bubbled hydrogen chloride through the solution, which caused some 2,5-dichloroaniline hydrochloride to precipitate out as a pink powder. I didn't get a whole lot of product, but the color seemed to indicate that it was a lot purer than the brown material I started with before. As for the pink color, I'm not sure where it comes from, but I've gotten the same pale-pink color from toluidine hydrochloride, so it at least seems consistent.

October 19, 2022

The past few days have been fall break, and I was pretty busy. In regards to synthesis, I haven't done anything groundbreaking. I successfully synthesized copper (i) iodide from iodine tincture (non-povidone) and copper (ii) sulfate, albeit only getting maybe 10–20mg. Considering I didn't use pure iodide salts, I'm okay with this. I hope to use this in conjunction with some acetonitrile to synthesize a dye formed between 2,5-dichloronitrobenzene and aniline via Ullmann condensation.

Also, I realized that my 20cm Vigreaux column only provided 2 theoretical plates, so I packed it with some shattered tempered glass and got the best results of a packed column yet—no flooding, very nice separation, and the glass was easy to remove from the column. Had I used BBs, it probably would've both flooded and been a pain to remove the packing material. 

I tested it out with some starting fluid, containing diethyl ether and some heptane. In the past, I would get a slowly-rising head temperature, which rose well above the boiling point of diethyl ether. This time, it stagnated at this point, indicating an actual fraction coming through, and it started to drop significantly when the diethyl ether wasn't coming over anymore. So, it works very nicely.

September 6, 2022

This past weekend, I was able to do some stuff at home. To start, I bought some RV and Marine antifreeze for around $4, as well as an aquarium air pump. The antifreeze consists of mainly water with a bit of propylene glycol (around 4%) and ethanol (around 10%), plus some dye, phosphate, and other stuff I'm sure. I also extracted some caffeine and purified it by sublimation, which I might do a write-up on. One final thing I did was make nickel (ii) sulfate heptahydrate by reacting basic nickel carbonate and dilute sulfuric acid, followed by evaporation to crystallize it. It's a nice blueish-green powder, and I plan on making some hexaamminenickel (ii) sulfate at some point, which should be less soluble in isopropanol than hexaamminenickel (ii) chloride.

I should really pick a longer project to invest my time in, but I don't really feel like pickings something on a whim. A lot of projects I had wanted to do have the downside of being low-yield and high-cost/time commitment, so I need to pick it wisely. 

August 26, 2022

Well, now I'm back in school. Between the last post and this one, I haven't done a whole lot. I made some more 1,4-dioxane, which I'm going to do a write-up on after a few weeks of being over sieves. I made some trimethyl borate by adding old boron trioxide to methanol with some sulfuric acid. All of it dissolved overnight at room temperature, which I attribute to the boron trioxide becoming less glass-like over time, instead having a more porous structure. I also was able to concentrate 3% hydrogen peroxide to about 6% hydrogen peroxide via repeated partial freezing. One final thing I did was made a possible copper (i) complex by reaction of copper (ii) chloride with acetone azine, which formed small gold crystals. However, I need to repeat the experiment again to ensure it's able to be replicated. Other than that, I haven't had too much time to do chemistry stuff. 

I did, however, finish Pharmacology for Chemists, which was incredibly informative in regards to pharmacology, metabolism, and overall drug effects in the body. It's helping me a lot with a course I'm taking currently, which is biochemistry. I returned it upon my arriving at school, and found another interesting book in a field I wanted to know more about: Lawrance's Introduction to Coordination Chemistry. So far, it's pretty good, although things like crystal field theory and ligand field theory are still a bit hard to wrap my head around (likely because I haven't delved into the fun world of molecular orbital theory all that much). 

Anyway, I'm going to be trying to do more in terms of write-ups when I get the chance, since the only ones I currently have are from 2021. Even if it's something pretty mundane, it reflects good lab practices to have things like overall note-taking and reflection. I'm also going to try to do some more product characterization, which is also something I've been slacking on.

July 9, 2022

I've been pretty busy at work, so I haven't had a whole lot of opportunities to do any extensive syntheses. Regardless, I've bought a few chemicals: 3A molecular sieves, acetonitrile, 3 micron zinc dust, and nickel metal. I've already put to use my molecular sieves in drying all of my solvents that I need anhydrous, namely my absolute methanol and isopropanol, as well as my diethyl ether, ethyl bromide, and 1,4-dioxane (even though it's not the best for this). The acetonitrile is just useful to have around as a solvent, being polar and aprotic, and I'm planning on exploring some interesting reactions utilizing it. The zinc dust is going to be useful for reductions, namely Clemmenson reductions and the production of hydrogenation catalysts. The nickel is useful with the zinc in the production of hydrogenation catalysts, but I also hope to make some interesting complexes.

With the nickel, I oxidized it to nickel (ii) chloride electrolytically, which worked much faster than typical methods, given nickel's corrosion resistance. I oxidized about 30g of it over the course of a couple days, then added a bunch of sodium bicarbonate followed by extensive water washings and drying to yield basic nickel carbonate. With this, I've successfully made nickel (ii) chloride, albeit in its dihydrate, not more-common tetrahydrate, state. 

Other syntheses I've done include producing even more methyl salicylate from aspirin, which I don't have a solid use for. Perhaps a transesterification to other salicylate esters, namely isopropyl. I've also synthesized methyl benzoate, which has a distinct smell: a little bit minty, but smells more "chemically" than methyl salicylate in terms of its mintiness.

In regards to Tyrian purple, I synthesized about 100mL of fuming nitric acid, which had an orange color. I had attempted to make dinitrotoluene, which is the first step, but the quality of the mononitrotoluenes was lacking (a viscous red/black liquid instead of yellow), so I scrapped it. I attribute this to dissolved nitrogen dioxide doing EAS reactions and tarring up the product. As a result, I've decided I no longer want to deal with the risks at the moment, so the synthesis is on hold indefinitely. I do plan on doing a different synthesis altogether, but I won't reveal what it is just yet.

May 13, 2022

I've been quite busy recently. Since I've been slacking in the write-up aspect of my syntheses, I've started meticulously writing down every procedure I'm doing. Onto detailing what they were:

I first made benzoic acid from sodium benzoate, followed by a recrystallization to obtain pure benzoic acid. I attempted to make isopropyl salicylate, but it only yielded a drop or so after 5 hours of reflux. I managed to at least recover the salicylic acid from it. I distilled some gasoline, collecting the amount under 85°C. I then further purified this distillate using water to remove ethanol, permanganate to remove alkenes, and distilled over base to remove carbonyls, collecting products in two temperature ranges. The smell was more butane-like than gasoline. I made some azeotropic nitric acid with a 68% yield, but had foam-over issues that made me quite earlier than I could have. I hydrolyzed some ethyl acetate with sodium hydroxide and obtained ethanol, then dried the ethanol over anhydrous copper (ii) sulfate. I used this for a sodium ethyl sulfate synthesis that I'm currently in the process of finishing. I purified out my chromium from the chromate I made a couple months ago by reducing it and precipitating it as the hydroxide. 

I went to Walmart and bought another pound of pure sodium hydroxide drain opener, a half-gallon of 93% sulfuric acid, and some methanol. The sulfuric acid is definitely going to be useful in the future for a variety of reactions and syntheses, for instance nitric acid, nitrotoluene, and producing hydrogen chloride.

Some projects I have planned that aren't the dyes are pyrolyzing polystyrene to styrene, which can then be used to make 2-phenethyl bromide with hydrobromic acid and a free-radical initiator. This can be reacted with hydrazine to produce phenelzine, which I've been after for 18 months now. I briefly looked into other hydrazine MAOIs, but none seemed to be as viable to synthesize as phenelzine.

May 8, 2022

The semester has officially ended, and so I'm home for the summer. Before I left, though, I picked up a book titled Pharmacology for Chemists by Joseph Cannon from my school's library. It's a good book to read for basic pharmacology with a focus on the chemistry aspect. Although some of it was stuff I had already known, I did learn some stuff about absorption and metabolism, namely how strong the effect of hydrophilic/hydrophobic characteristics are in regards to these. 

So far, I've recovered some dry mercuric chloride crystals, which have been drying in a jar filled with calcium chloride for the past 4 months. I recovered 5.3g, which was more than I was expecting based on looks. I failed on making aluminum isopropoxide with it, but managed to recover the mercury using water, then hydrochloric acid to dissolve the aluminum, followed by copper powder to aggregate the mercury, then more hydrochloric acid, hydrogen peroxide, and potassium permanganate, which gave a small bead of mercury metal. I plan on using the mercuric chloride for some kind of reductive amination. 

I also made some salicylic acid, of course. It's probably the most typical reaction I do, I'm finding, since aspirin is cheap from the Dollar Tree. I don't have a plan on what to use it for, however; I have enough phenol, and some other things like methyl salicylate and salicylamide aren't piquing my interest. I might make some amount of isopropyl salicylate, though, as it has a unique smell: like a glossy magazine with a hint of mint in higher concentrations.

I also have some starting fluid that I would like to distill as soon as possible; it's going to be in the mid-80°Fs soon, which is terrible for the collection diethyl ether. While I don't know what it'll be used for, I'm actually going to stablize it with a small amount of hydroquinone to prevent peroxide formation, and it's just nice to have on-hand in general; the heptane will also be nice to have. 

May 1, 2022

I recently had a break for Easter, and got to do a couple of cool procedures. 

The Dollar Tree finally stocked 325mg aspirin pills again, so I used a bottle of those (100 pills in total) to make methyl salicylate. This was done by first extracting the aspirin, hydrolyzing the acetylsalicylic acid to salicylic acid, and then esterifying the salicylic acid with methanol to form methyl salicylate. I got 6.1g of a liquid that smelled very similar to wintergreen Lifesavers.

Another thing I did was synthesize hydrazine sulfate from bleach on a larger scale than I was used to, using 500mL of 7.5% bleach. The reaction itself was nothing special, but I tried using 31% HCl instead of sulfuric acid to neutralize the sodium hydroxide and sodium carbonate. I then added 50% sulfuric acid once the bubbling died down, and was somewhat concerned when nothing precipitated. So, I let it sit to cool down, and some glittery white crystals formed. I filtered these off, then recrystallized in water to remove any sodium salts and acid. I was left with some very nice hydrazine sulfate crystals, with a yield of about 32%, which is typical according to previous syntheses of this. 

Other than that, I didn't do much. Over the summer, since I'll have more time, I'd like to look into getting some dry ice from a regional hypermarket for nitrotoluene isomer separation. Because my plan of using manganese dioxide to oxidize a substituted toluene to a substituted benzaldehyde probably won't work, I'm also going to look into a different oxidation pathway, perhaps the Étard reaction or a two-step reaction involving chlorine gas and sunlight, then hexamine and hydrochloric acid.

Other plans that I'd like to accomplish are the synthesis of various other compounds; if I can perform a multi-step, somewhat-difficult synthesis, it will be worth writing an extensive write-up on and it'll be something I can talk about in the future with potential jobs or research positions.

March 20, 2022

Since I'm wrapping up spring break now, I did a decent amount of cool chemistry. I ended up distilling out the diethyl ether from the starting fluid. Thankfully, it had snowed, so distillation was facile—I used snow to cool both the receiving flask and condenser water. I ended up getting about 100mL of ether that may have been slightly contaminated with heptane, but this wasn't a big issue (I plan on using it for Grignard reactions if it doesn't leak out of the bottle first).

I also made some phenol from the thermal decarboxylation of salicylic acid. I got about 4.5g out of a theoretical 30g, which is incredibly poor. But, I attribute the low yield to both isopropyl salicylate formation during the extraction/hydrolysis and side reactions occurring during the thermal decarboxylation due to poor temperature control. Although disappointing, I didn't have plans for this phenol, so it's alright. 

I also tried another synthesis involving the reduction of 2,5-dichloronitrobenzene, like I've done in the past. This time, however, I used iron powder from a Hothands packet. Upon reacting, filtration, boiling-down, and cooling, I got some amount of needle-like crystals, which is consistent with the PubChem data for 2,5-dichloroaniline. On the ScienceMadness forums, I was informed that the hydrochloride salt of 2,5-dichloroaniline readily reforms the freebase and hydrochloric acid, which is consistent with my observations. I'll see how well it crystallizes over the course of however long I'm not home for, since I don't plan on recovering the crystals at the moment.

I did try—and kinda fail—to do some other stuff over break. I had attempted to make sodium dichromate from stainless steel via dissolving the steel in HCl, then adding carbonate, drying, and reacting with bleach. The half-cell reaction to make chromate is incredibly important for this reaction, since a lack of added hydroxide causes hypochlorous acid to be formed, which quickly decomposes. So, sodium hydroxide has to be added in order to maintain equilibrium. The reason I failed was because I didn't dissolve enough steel, so I ended up overestimating the amount of bleach, which, in turn, made me add way too much acid to convert everything to dichromate. I did this outside, but there was absolutely a lethal amount of chlorine gas generated. After sitting outside, though, the chlorine dissipated. I have an estimated 10–20g of sodium dichromate in >1L of water, which also contains a significant amount of sodium chloride. So, it'll be hard to 100% purify without getting into sludge territory.

I also tried to make some copper complexes, namely a cupric chloride-urea complex. It didn't work, possibly because I didn't cool it down enough. Nonetheless, I think that urea isn't a great ligand. Something like hydrazine would be interesting to investigate, but I lack the knowledge to handle dilute hydrazine solutions in a manner I would be comfortable with.

Another thing that I did was test the crystalline precipitate I obtained from nitrotoluenes that I believed to be p-nitrotoluene. Turns out, it was dinitrotoluene isomers, since the melting point was in the mid to high 60°Cs, which is significantly above that of p-nitrotoluene. This does make more sense in hindsight, but it means that I'll be unable to proceed with my indigo procedure unless my home freezer can get below -12°C. 

March 7, 2022

This past weekend, I was able to do some syntheses. Although, I didn't really do a whole lot of in-depth chemistry. I purified my ~600g of copper (ii) sulfate pentahydrate by hot filtration and recrystallization. I made some huge crystals by letting the beaker cool insulated overnight, but decided that it was too difficult to remove the crystalline mass, so I redissolved and recrystallized it into much finer crystals, around the size of sand. This is useful because I won't have to break up any crystals. With the copper waste, such as residual copper (ii) sulfate stuck to the sides of the beaker, I redissolved it and added a bit of hydrochloric acid, followed by aluminum foil. This made some copper powder, which is useful for Ullmann-style reactions. It also helps recycle the copper and not just pour it down the drain. This process took a good day's worth of work.

I also did a few distillations of various solvents I had. First was some waste 91% isopropanol from drying the copper (ii) sulfate. Another was some 1,4-dioxane that I had stored over iron (ii) sulfate for a few months to destroy any peroxides. I added some hydroxide to the distillate to prevent peroxide formation, as well as stored it in a jar and not a soda bottle. Overnight, this turned orange, indicating acetaldehyde polymerization. So, it's unusable until I redistilll it. I also distilled some ethylene glycol from antifreeze. I added two pinches of sand, plus I insulated the entire distilling side and used magnetic stirring, so bumping was non-existent. I don't have any plans for this ethylene glycol, but I also opted to store it in a jar, owing to its hygroscopic nature.

Some lab equipment I've been thinking about buying lately include a vacuum aspirator and water pump,  molecular sieves, and a stand. Also, I bought some engine starting fluid this past weekend, which I plan to distill when the weather gets cold this upcoming weekend.

February 2, 2022

Well, I've thought of a good way to make Tyrian purple using dinitrotoluene as a main starting material. It's nothing atypical, just a para-reduction, Sandmeyer reaction, and benzyl oxidation, followed by the indigo synthesis. The good thing about this reaction is that there's no isomer separation needed. The downside is that the yield seems like it'll be pretty bad, probably around 10%. But, I could surprise myself and it'll be higher. I still plan on making just indigo, too, and I might do that first or do a large-scale toluene nitration, of which some goes to another nitration to form the dinitrotoluene. Since I'd need a bunch of nitric acid, though, I'll probably need to get some more sulfuric acid and potassium nitrate. But, that's not too much of a problem.

I did get inspired to re-visit a project I've tried multiple times in the past, albeit not the same procedure. It's the synthesis of phenelzine, which is a hydrazine-based MAOI. I think that this compound would be really cool to make just to say I did.  In the past, I've followed a Chinese patent that, after trying it multiple times and asking some people, turned out to be faulty. Now, I'm researching some possible pathways, one of which involves 2-phenethyl bromide. 

I may end up just not doing that, though, since this is now my fourth multi-step project that I want to do, the other three being the synthesis of indigo, Tyrian purple, and benzo-[c]-cinnoline. Considering I don't have opportunities to do chemistry at school, it'll take several weeks to do a single project, even longer if purification is difficult. But, I'll cross that bridge when I'm actually able to go home and do some reactions.

January 31, 2022

While I've been at school, I've been doing some research about interesting projects I can do with the chemicals I have. The first one I thought of was performing the Ullmann reaction of 2,5-dichloronitrobenzene to form 4,4'-dichloro-2,2'-dinitrobiphenyl. This opens up a lot of potential derivatives by reduction of the nitro groups and/or reduction of the chloro groups. The latter just replaces the chloro groups with hydrogen groups. The former, however, isn't as straightforward as it may seem. Most attempts to reduce the nitro groups results in heterocycle formation, most notably forming benzo-[c]-cinnoline (which isn't all that bad—I'll go into it in a bit). The only procedure I've found that completely reduces it to a 2,2'-diamine involves fine tin powder and 31% HCl. Diazotization of this diamine in acetic acid forms carbazole, albeit in around a 50% yield, and at that point in the synthesis, I'd probably need around 100g of 2,5-dichloronitrobenzene to get a decent overall recovery.

The benzo-[c]-cinnoline isn't bad because recent studies have successfully used it as a catalyst in oxidizing alkyl halides to aldehydes. Although this reaction is performed in DMF and takes 16 hours to complete, the advantages are a pretty high yield, few side products, and cheap starting materials. I may end up using this to make good benzaldehyde from benzyl chloride, but I might also just stop at synthesizing the benzo-[c]-cinnoline.

Another project is the synthesis of indigo using the traditional Baeyer-Drewson synthetic pathway. The 2-nitrobenzaldehyde can be made using o-nitrotoluene and either chlorination plus Sommelet reaction or direct benzylic oxidation using manganese dioxide. I'd prefer to do the latter, but the former is an option. If I synthesize this, I plan on dyeing a t-shirt with it; I'm not one to normally wear jeans, but depending on how proud I feel of the dye, I'll consider dyeing a pair of those as well. I had also considered synthesizing Tyrian purple instead, since it just requires bromination of the 2-nitrobenzaldehyde, but the isomer separation seems annoying without a good separation techniques e.g. column chromatography, and I'd rather try the traditional way first.

January 26, 2022

In the past couple months, I've done quite a bit. I'm only going to focus on what I did over Christmas break, though, since I don't believe I did a whole lot between the last post and then. I ordered 25g of mercury metal, which arrived shortly after the break started. I also got some lead metal in the form of sinkers. I made some 50% nitric acid with water, sulfuric acid, and potassium nitrate, which I used to dissolve some of the mercury and lead. I also made some benzaldehyde with it, using the rest of my benzyl alcohol. I made some more benzoin, then attempted to make deoxybenzoin twice, both of which failed.

With the mercury nitrate, I precipitated out mercury (ii) hydroxide, then redissolved it using drops of hydrochloric acid to generate a neutral mercuric chloride solution. With the waste, I made sure it wasn't acidic then added some sodium polysulfides (formed by reacting sulfur and sodium hydroxide in water). This precipitated mercury (ii) sulfide, which both removed the mercury from solution and meant I could recover the mercury at a later time.

With the lead nitrate, I primarily made lead (ii) chloride. I followed a procedure to make ammonium hexachloroplumbate, which turned out quite well! I got some shiny bright-yellow crystals, which is consistent with literature.

Other projects I did included making more ammonia solution. While generating the ammonia, I made some tetraamminecopper(ii) sulfate, which formed beautiful navy-blue crystals. I also learned my nitrotoluene isomers had separated, and I was left with p-nitrotoluene crystals under liquid o-nitrotoluene. I filtered them off and recrystallized them from water and isopropanol. With the o-nitrotoluene, I reduced it using steel wool in HCl, followed by basification and steam-distillation into toluene. I bubbled some HCl gas through this toluene, and recovered, in a low yield, o-toluinide hydrochloride as a slightly-pink powder.

I also attempted to do some reductive aminations, none of which were successful, and nitration/reduction of naphthalene, using sodium dithionite as a reducing agent. It did not result in any product. One last failure I had was trying to make aluminum isopropoxide, which did not turn out. With this and the reductive aminations, I'm thinking it was due to the poor method of amalgamation.

For my next project, I'm planning on doing a multi-step reaction starting with p-dichlorobenzene. I plan on first nitrating it, then using copper at high temperatures to join two molecules to each other, then reducing off the chlorides, then finally reducing the two nitro groups to an azo group. This makes benzo-[c]-cinnoline, which can be used as  a catalyst to oxidize alkyl halides to aldehydes using air as the oxidizing agent.  If I can make this compound, I can make benzaldehyde just using toluene, bleach, hydrochloric acid, and atmospheric oxygen.

November 29, 2021

So, I did quite a bit over Thanksgiving break. I recrystallized some more potassium chlorate, made some benzoin (which I'm posting a procedure on), salicylic acid, benzyl chloride, and broke in my new distillation adaptor. It worked quite well, and I'm making sure that I'm always wrapping the joint leading to the flask in Teflon tape. I'm hoping to research and actually have a synthesis planned for Christmas break in a few weeks. 

I had attempted to make some manganese salts from battery-grade manganese dioxide, but after boiling the solution to near-dryness, I got a chartreuse salt instead of the pale-pink salt I was expecting. I had a feeling it wasn't some manganese (ii) chloride complex because Woelen from ScienceMadness tested it, and it didn't ever form a green color.  So, I concluded it was either ferric chloride or a higher oxidation state manganese compound. The color made me immediately think of ferric chloride, so I tested its reaction with both salicylic acid and sodium ferrocyanide. It formed a purple color and deep blue precipitate, respectively, so it was definitely ferric chloride. I honestly didn't know where the manganese went.

Otherwise, I don't really know what my plans are for the chemicals I made.  Possibly making some benzilic acid with the benzoin and doing some Grignards with the benzyl chloride. I'm not sure, but I'll figure it out.

November 16, 2021

This weekend, I mainly recrystallized all of the chlorate I had to make some beautiful crystals. In the end, I got a bit more than 40g of nice crystals of potassium chlorate. Plus, some powdery crystals that I put into its own container; I didn't weigh these. I also made some manganese dioxide, though I probably only got a 20% yield. But, considering how cheap zinc carbon batteries are, I don't really care. I plan on using this for benzylic oxidations at some point. Also, when I get the chance again, I'm going to try and make some really soluble, but not deliquescent, salts and let them evaporate over time to give nice crystals.

In other news, I bought a new distillation adapter to replace the one I broke. It's going to arrive in December, but I'm still glad I bought it now than later.

November 9, 2021

Yesterday, after about 36 hours, my chlorate cell had crystallized, so I recovered the potassium chlorate in a similar way as last time. It wasn't as pure because I had to hot filter, which didn't get all of the graphite out. Nonetheless, I recovered 7.0g after drying, which, for that short of a time, I'm happy with. 

November 7, 2021

Well, I managed to do exactly that with my chlorate cell. I bought some potassium chloride as "Nu-Salt" from Meijer (a local superstore), since it was cheaper than the "NoSalt". It was just a matter filtering off the big graphite pieces from the chlorate, then adding a solution of KCl and cooling in the freezer. I decanted off the liquid from the slush of crystals at the bottom into a separate container, then poured the slush onto a paper towel to wick away most of the water. I then squeezed it as hard as possible to get rid of the rest, then put it into a small cup of 70% isopropanol. I swished it around until it was a slush again, then poured it onto another paper towel. I put this on a fan to dry, scraped off the dry crystals into a filter paper. I repeated this process about 3 or 4 times due to the amount of chlorate that was there. Afterwards, I put it in a desiccator jar to dry overnight, and my yield was 12.9g, which I'm really happy about! I also switched the cell over to a potassium chlorate cell, so hopeful I get some more apparent results going forward.

November 3, 2021

Today, I decided to return Essentials of Medicinal Chemistry, both because it wasn't all that interesting anymore and because I wanted to check out a different book: Comprehensive Organic Named Reactions and Reagents v.3. by Wang.  The reason I chose the third volume is because I found a .pdf online of all three volumes, but it's missing the appendix, which is located in the third version. I want the appendix because it shows the reaction and name, but doesn't have any details as to the background or modifications. So, one can think of it as almost an index. I plan on scanning this so I can have it along with the rest of the book.

The copper wire on my graphite anode got corroded, so I've decided to halt it for a little bit. I'm planning on switching it over to a potassium chlorate cell as soon as I can, because the potassium chlorate is not only more recoverable, it's also less hygroscopic and thus more useful as an anhydrous oxidizer. I think I'm going to turn the sodium chlorate I have into potassium chlorate, since I have yet to have anything precipitate, and then filter and recrystallize.

November 1, 2021

Yesterday, I added more salt to my cell, and the caulk on the epoxy came loose. So, when the cell runs, there's a small amount of bubbling that occurs occurs between the caulk and the cathode. Nothing too dangerous, just messy. The amount of salt I added formed a thick layer on the bottom of the cell, and it caused the bubbling rate to increase somewhat. This morning, I got somewhat worried and filtered the salt out of the solution. A short while later, the cell stopped working, which I later learned was due to the copper wire oxidizing from the graphite rod. So, I ended up taking out the short piece of tubing that was epoxied in and just dangled the graphite rod in the solution through the hole in the lid. So, it's not a closed system anymore, but the majority of salt "mist" should be mitigated by having the lid remain on.

As for my Disperse Yellow 26 research, I've been looking into Ullmann condensations some more; so far, the biggest hurdle I've found is in the copper catalyst. From what I've seen, in order to get decent selectivity, you need to use a copper compound that's bound to certain ligands, such as copper (i) iodide and a certain 1,3-diketone. Not terribly difficult to obtain, but just really annoying. I also don't know how selective this reaction is. So, I may look into other methods of synthesizing this. 

October 29, 2021

I ended up changing my graphite electrode to a brand new one (plus added more salt), and the cell seems to be performing a lot better. The temperature of the cell has gone up 10°C–20°C, and the rate of bubbling of hydrogen has nearly doubled. The temperature raise is definitely going to improve cell efficiency by favoring the disproportionation of hypochlorite. I'm not too sure why it shot up like this, but I think it has to do with current density and surface area of the graphite rod. I hope that it doesn't start to disintegrate for a while, at least until I'm able to get more electrodes (I only have two other ones—both already heavily eroded). 

I did do some research today, and I stumbled across a dye called Disperse Yellow 26. As the name implies, it's a yellow dye, though it can also be orange. Unlike dyes that I've made in the past, it's not an azo dye; rather, it's formed by the SnAr substitution of 2,5-dichloronitrobenzene with aniline. This, however, is disadvantageous, as the substitution isn't very easy for the home chemist, requiring high pressures to allow for higher temperatures than the boiling point of the solvent allows for. So, to get around this, I believe Ullmann-type condensations can be done. In this reaction, an aryl halide is reacted with a nucleophile in the presence of a copper compound to form a substituted nucleophile. In my case, this would be the reaction between 2,5-dichloronitrobenzene and aniline to form the Disperse Yellow 26. I still need to look into it further, of course, but it's definitely an interesting synthesis.

October 28, 2021

Today, I picked up two new books from my library: The Nitro Group in Organic Synthesis by Ono and Modern Organic Synthesis in the Laboratory: A Collection of Standard Experimental Procedures by Li, Limberakis and Pflum. I haven't done much except skim through them, but they're quite interesting so far. One thing from the latter book that I thought was really fascinating was a procedure involving using baking yeast and sucrose to reduce certain functional groups. You don't see too many enzymatic procedures that can be useful to the home chemist. I'm looking into just how accessible it is.

My chlorate cell is still going well. I added more salt yesterday, which all seems to have disappeared. There is starting to be some salt creep that is happening from between the threads and goes down the side of the jar. It's not that big of an issue because I have a plastic container underneath it to catch anything like that. The only issue I can foresee there being is if the lid of the jar starts to rust. I coated it twice in clear nail polish to attempt to protect it before starting the cell, so we'll see how that goes. Seems like the graphite rod is starting to degrade a decent amount, judging by the color of the solution. I may check on it within the next day; I'd like to avoid my cathode completely rusting from standing in the solution.

October 26, 2021

Well, this is officially the first post here, and it certainly won't be the last. I should probably talk about all that I'm currently doing. 

While I haven't been doing a whole lot of research at the moment, a synthesis that I recently attempted, but got a dismal yield, was the synthesis of 2,5-dichloroaniline from 2,5-dichloronitrobenzene using a Béchamp reduction and steam distillation. In a brief summary, my reduction only worked for half of the reactants, and the subsequent steam distillation caused a bubble-over of a lot of particulate iron hydroxide. Not to mention, my 3-way distillation adapter got fused to my flask, so I had to chisel it out. I ended up recovering around a 20% overall yield using an acid/base extraction with toluene and HCl. Not a fun synthesis all around. More info about it is on my write-ups page. The purpose for making 2,5-dichloroaniline is to make 2,5-dichlorophenylhydrazine, and subsequently both 4,7-dichloro-2-methylindole and 4,7-dichloro-2,3-dimethylindole using acetone and methyl ethyl ketone, respectively.

Another thing I have now is a small sodium chlorate cell running in my room. I've had a lot of success with potassium chlorate with this charger (5V and 2A), but haven't ever done a sodium chlorate cell. Unlike previous cells, I'm doing this inside, so I drilled holes in the lid of the jar for my stainless steel cathode, and two small pieces of tubing—one for graphite rods to fit in and the other for a longer tube to go in for gas exchange. I also caulked it so it withstands the saltwater mist that's produced, as well as wrapped the threads in Teflon tape. It seems to be holding up thus far; no leaks have developed, the pressure is high enough in the cell to bubble gas out through the tube, and the smell of chlorine is minimal, so I'm hopeful it continues to work.

As for books, I'm off-and-on reading Essentials of Medicinal Chemistry by Korolkovas and Burckhalter. I saw it in my school's library, and thought it would be interesting to read. I was right, though there's not as much opportunity to take notes compared to previous books. I think the most interesting thing that I've learned in it thus far is that receptor antagonists can theoretically be made by putting bulkier groups on a receptor agonist. Pharmacology is quite interesting to me, but I have little interest in pursuing it further than learning about how different compounds affect the brain.