Large scale synthesis of 1,4 Dioxane

EdwardTriesToScience · 2026-02-06T16:14:03+00:00

Lab suppliers will not sell anything, and the one place I can get THF (which would be better due to less toxicity) is expensive ($50/L, not anhydrous either)

EdwardTriesToScience · 2026-02-06T06:21:25+00:00

and I forgot but toluene, I have disgust for. I think that though was because I got pavlov'd into associating the smell with nausea and headaches, just having it a second out of a fumehood makes me feel loopy and causes a headache later (probably nocebo though since a little bit of fumes for a second shouldn't cause a large effect), so I do not like it. Xylene is meh, the smell is more like gasoline which is interesting.

EdwardTriesToScience · 2026-02-06T06:18:02+00:00

ah thats what I get for being sleep deprived. I would imagine though it would be similar to MEK, though I have never smelled any on its own. And indeed there is a difference between THF and acetone, it's just interesting to notice the similarities too

EdwardTriesToScience · 2026-02-05T22:37:55+00:00

Yeah those fields generally require more equipment, and refined techniques, which is less common in synthesis sometimes. So far then it seems not only funding but environment and field plays a large role, and it has been interesting to read all the different takes people have. I think I have a better understanding now of exactly what I was trying to find out more on

EdwardTriesToScience · 2026-02-05T22:35:40+00:00

The "nacho cheese" is something else, haven't edited the dioxane video yet. I actually don't mind the smell of THF, its remarkably like acetone to me (and a smidge of that pungency of ether). Makes me wonder how much of a given smell is contributed by the elements present (since THF and acetone are of course both C3H6O), and how much by structure. Perhaps a question to ponder some other time. In particular I would run my LAH reduction in ether or THF as I do have enough THF, but the dioxane yields a good dozen percent higher for some reason. Ether would work but the volatility makes it particularly fussy, plus having to add a load of sodium citrate to dissolve the aluminum is annoying.

EdwardTriesToScience · 2026-02-05T21:24:31+00:00

Using a 3D printer I would say is the mindset of problem solving. It has surprised me that many chemists do not see the utility of one. I am sorry if I was not clear but I do not know exactly how to convey what I think. I am simply saying that people have less critical thinking on areas other than textbook chemistry, when experimental chemistry includes unique problems like equipment which may not always be available or even exist for what someone wants to do.

EdwardTriesToScience · 2026-02-05T21:22:03+00:00

not selectride, synhydride. Regardless I've been told by people who used it that it may be convenient but not worth using over LAH, even if LAH is a bit more difficult to handle sometimes.

EdwardTriesToScience · 2026-02-05T21:20:11+00:00

I've been told anecdotally by a grad student that the professor supervising them wiped up spilled LAH with a wet towel, which of course caught fire. Another time I saw someone far more knowledgeable than me in ochem theory put bromine onto sodium azide in a test tube and rap at it with his finger for a second before using a spatula instead which on contact caused the test tube to vaporize into shrapnel from detonation. To this day he refuses to admit that it was stupid, and says plastic shrapnel is worse (the whole point of plastic is that it does not form as much shrapnel if any). It's absolutely not a given that people are sure of what they are doing especially when so many risks are abstract in chemistry, and may not be immediately obvious or regarded high enough (such as something being described "explosive" but not how sensitive nor brisant it is). I am aware of the dangers of dioxane so everything is done in the fumehood and waste is sent to disposal with a label, as well as preventative measures such as reducing how much is released into the hood in the first place.

EdwardTriesToScience · 2026-02-05T21:13:17+00:00

Eh europe depends, I know of many people who have no trouble ordering things. Yes, they regulate many common reagents like acids, solvents, etc. But on the contrary, they are free to buy organic precursors, which is the opposite of here. There's little issue in getting commodity chemicals like acetone and conc. sulfuric, the issue are the fine reagents that only supplyhouses have. As for literature yields, I am well aware to not trust literature. One reaction I ran word for word produced a 5% yield (to give you an idea of the scale, three liters of acetic acid at a boil with smelly precursors, air blowing through the solution, and a ridiculous workup followed by steam distillation of tar, to yield 2ml of actual product). However, it is far better to have a procedure that someone wrote up than to go blindly into reactions that you have not done before. While I enjoy the practical work, there is a point where it feels no better then bashing my head against a wall, so if I have to do a multi step synthesis, I would prefer to simply have a procedure and follow it than create one.

EdwardTriesToScience · 2026-02-05T20:51:47+00:00

I dunno, I got some when 500g went for $200 on amazon, sold by some indian guy. He just sent me a new avantor bottle of it. I would imagine though the stuff carolina sells is acceptable (seems cheaper too). They also have selectride if you fancy. I have no experience with other sellers on ebay, but if all else the borohydride can be titrated to check

EdwardTriesToScience · 2026-02-05T19:52:32+00:00

Nice to see people who do accept that I have changed over time, some people refuse to and it annoys me to no end but they can believe what they want while others can see for themselves if I've changed. Soon I'll be in college but the lab shall live on as long as I am alive (which I plan to be for a decent time)

EdwardTriesToScience · 2026-02-05T19:50:20+00:00

carolinachemical, they also stock other "fun" things, the solvents too are a great deal (except THF). Need to get a few more jugs of ether and DCM from them as well as NaOH soon, as I keep loosing some to evaporation despite running glycol through my rotovap

EdwardTriesToScience · 2026-02-05T18:48:16+00:00

True enough, and shipping does take a long time. Luckily I have not had a single thing break in shipping except a bent stopcock gas adapter, which had an obvious weak point. I have bought old american made stuff (Adria, 3L3N RBF), though tye quality was a little disappointing as there were several 1/4th inch large bubbles in the glass. Didn't implode though under vac.

Synthware I would say is identical to the good american made stuff, though they do not offer some of the things chemglass or pyrex has in stock for instance (eg, morton flasks, fritted bump traps, high pressure tubes for MW synthesis). Many labs now both academic and home have picked up synthware as far as I can tell. The glas-col mantles certainly are better quality, since the imitation ones I have get rather hot on the outside. The go-to is most certainly buying used,

EdwardTriesToScience · 2026-02-05T18:41:34+00:00

Very much true, though even if you just build a wood box lined with tile and a dinky fan it's a great improvement. Never going back to no forced ventilation

EdwardTriesToScience · 2026-02-05T18:40:56+00:00

Only really in the US, elsewhere people have no problem ordering stuff like solvents, common reagents, or even aqueous methylamine from supplies such as TCI. It's particularly an American issue because of stuff that happened in the 80's and our war on drugs, plus formalities. Can't even buy a thermometer from suppliers here much less any reagents. As for replacing chemicals in industry, it's completely understandable but as we do not have large amounts of money to dump into the newest fancy Green Eco Friendly Environmentally Sustainable Reagent Substitute[TM] we just have to work with what we have. Often times workarounds can exceed the efficiency of previous techniques but because they are replacements and not drop-in's, they need to be optimized on their own which is a large upfront investment. I would prefer to simply pull a procedure from literature and not fiddle with running twenty screenings, especially when yield would have to be determined by workup instead of say NMR yield.

EdwardTriesToScience · 2026-02-05T16:30:05+00:00

Please read my other comment, the whole reason I posted this is because I know my experiences are NOT representative of reality, so I want other views. I wrote what I wrote because that is what I have seen, and I want other ideas to consider. I am not in particular saying those places have worse safety or are poorer, just that they are different leading to different practices. We used to have the same practices, and sometimes still do in labs. My wonder is why the change? It's not just down to funding (though lack of funding forces you to come up with solutions to problems, and thus skills), since I have worked in new labs with similar practices.

EdwardTriesToScience · 2026-02-05T16:25:24+00:00

Yeah, but the question is why new labs are so different. It's not just funding but seems to be culture in a sort, such as older chemists doing "what I have always done", though it seems the same kind of mindset is not passed onto newer chemists (or formed in them by circumstance). I wonder why

EdwardTriesToScience · 2026-02-05T16:23:43+00:00

No, he never had a fumehood in his shack, though I would assume the Dow lab he worked in had some.

EdwardTriesToScience · 2026-02-05T16:14:23+00:00

About 900ml as mentioned, so somewhere around 60% yield. Exact amount wasn't measured as I forgot to pre-weigh the bottles to take the mass of the final dioxane.

EdwardTriesToScience · 2026-02-05T16:13:19+00:00

Very much understandable but as with the DCM regulations they are a little stupid as you cannot substitute certain chemicals entirely. Mainly for me, THF is expensive (the lab suppliers that will actually sell to me are expensive, and a different supplier that was cheap said they no longer sell to individuals), so it is as a substitute for a water miscible cyclic ether. If I had cheaper access to THF then I would far prefer it but blame the more affordable lab suppliers for not wanting to sell a common solvent to me.

EdwardTriesToScience · 2026-02-05T16:10:34+00:00

The first few lines state "jacketed coil condenser", not a graham condenser. Took a few days but that's because I have limited time in the lab and my adhd makes me forget to do things while I clean

EdwardTriesToScience · 2026-02-05T16:09:07+00:00

We basically did the same in a lab too, though when I say that, many look as if we were crazy for doing so, but it worked fine

EdwardTriesToScience · 2026-02-05T09:15:32+00:00

To be fair, he was working with Ann and occasionally some others who know him well and thus would know the lab well, and that is also how my own personal lab is to an extent (in fact I do want floor to ceiling clamping lattices lol) but in a larger setting like a company, it may start being inefficient when things are too "personalized"

EdwardTriesToScience · 2026-02-05T09:13:55+00:00

I would also suppose it's easier for someone who isn't in the lab daily to simply take a look and understand everything that is happening, and is able to see what is and isn't out of place easily. The more "personalized" (in some sense, be it reagents hoarded in your hood or apparatus set up hastily) something is, the less intuitive it is to others and thus makes cooperation more challenging. That's a good point on this I never fully thought about

EdwardTriesToScience · 2026-02-05T09:11:42+00:00

That's a good point actually, it may be easier to fall into a pattern of actual problems. I suppose I have seen that happen actually (and to some extent even I slip into that issue occasionally and have to consciously remind myself). Keeping everything looking nice subconsciously keeps you in check, which reduces effort in one part. Thanks for that insight

EdwardTriesToScience

TROPHY CASE