Sciencemadness Discussion Board

obtaining isopropenyl acetate?

davic666 - 26-3-2012 at 13:16

does anyone know where i might purchase about 250 ml. of isopropenyl acetate? its not a watched or regulated chemical, but all i've come up with are the big, big suppliers(aldrich, tci, etc.) who i'm not able to purchase from...

Hexavalent - 26-3-2012 at 13:29

Could you not synthesise it . . .an esterification reaction could be the way forward.

UnintentionalChaos - 26-3-2012 at 15:55

Quote: Originally posted by Hexavalent  
Could you not synthesise it . . .an esterification reaction could be the way forward.

At least google the compound in question before suggesting things. That is an enol ester, which cannot be made by Fisher esterification (that I am aware of).

gutter_ca - 26-3-2012 at 16:08

Dr.Bob - 27-3-2012 at 07:12

Where are you located? US or other, if US, what state? No one can help you if they don't have any idea where you are.

Hexavalent - 27-3-2012 at 12:53

Quote: Originally posted by UnintentionalChaos  
Quote: Originally posted by Hexavalent  
Could you not synthesise it . . .an esterification reaction could be the way forward.

At least google the compound in question before suggesting things. That is an enol ester, which cannot be made by Fisher esterification (that I am aware of).

I did not state a Fischer esterification.

Not exactly what the OP wanted, but could be useful^

[Edited on 27-3-2012 by Hexavalent]

davic666 - 28-3-2012 at 02:36

i'm from the usa; arizona to be specific...

Dr.Bob - 28-3-2012 at 09:39

Do you know that Heisenberg guy? I think he lives near there... Sorry, I couldn't resist. But I can understand how hard it must be to get chemicals there now.

But unsaturated esters tend (like most unsaturated compounds in general) to be unstable, so an old bottle or even freshly made batch will likely polymerize quickly if you don't add an inhibitor to it or otherwise keep it away from light, air and water.

That is just an odd enough compound to be hard to find, that you might want to check with a local university or business, if you can show a legitimate use for it. It is cheap from Acros or Alfa at $1/10 g, and does not appear to be listed, so some people might be willing to help.

I would think you might be able to make it from acetone and acetyl chloride under acidic or basic conditions, but not many papers. One is below. Most preps use acetone and ketene, which is also hard to come by.

From acetone and acetyl chloride in 2 steps
Cheng, Yongmei; Xu, Gang; Wu, Jianping; Zhang, Chensheng; Yang, Lirong
Tetrahedron Letters, 2010 , vol. 51, # 17 p. 2366 - 2369

Semibatch Reactive Distillation for Isopropyl Acetate Synthesis
Wei Qi and Michael F. Malone*
Department of Chemical Engineering, University of Massachusetts
Ind. Eng. Chem. Res., 2011, 50 (3), pp 1272–1277
DOI: 10.1021/ie100354x
Publication Date (Web): August 13, 2010

also JACS, 88, p. 2054, 1966 DOI: 10.1021/ja00961a043

DJF90 - 28-3-2012 at 10:51

Try this one...
Attachment: ja01225a002.pdf (240kB)
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isopropenyl acetate?

davic - 12-4-2018 at 23:56

DOES ANYONE HAVE ANY IDEA WHERE TO OBTAIN 500-1000 ml. of isopropenyl acetate at a reasonable price?....THANX

XeonTheMGPony - 13-4-2018 at 12:08

Make it?

weilawei - 13-4-2018 at 12:11

Xeon, I couldn't hear you. Could you say that a little louder, please? ;)

XeonTheMGPony - 13-4-2018 at 12:20

I just can't match davic's exuberance! at least not at current caffine levels!

Texium - 14-4-2018 at 07:24

Thank you, unionised, for linking to this thread. I deleted the link since it is now self-referential. Poor davic, looks like he's still been trying to acquire isopropenyl acetate for the last 6 years and now he needs even more of it.

Joking aside, isopropenyl acetate is a tough one. The syntheses suggested here look to be expensive and unwieldy on the scale that the OP needs since they require stoichiometric amounts of acetyl chloride and/or bromine. The usual industrial route, reaction of ketene with acetone, would be much cheaper and easier to run (on a large scale), but because of the dangers of ketene, it would have to be carried out by someone experienced, and in a good fume hood. Doug has a good video on making a ketene lamp.

unionised - 14-4-2018 at 07:42

Ketene isn't nice to work with but, if you insist on using it, there is an example here

VSEPR_VOID - 14-4-2018 at 08:53

If you do make some by an esterification make sure to put on entry on the List of Chemicals and Materials Made by Users

zed - 16-4-2018 at 14:33

Well, it is the enol ester of Acetone.

Not easy to trap acetone in its enol form. Super reactive Ketene, does it, easy-peasy.

All you need is acetone, a little glass ware, and electricity.

Just bubble your Ketene though Acetone rather than Acetic Acid.

Extreme caution is required when using Ketene. Given the chance, it will rip through your lungs like a Roto-Rooter.

[Edited on 16-4-2018 by zed]

[Edited on 16-4-2018 by zed]

[Edited on 16-4-2018 by zed]

clearly_not_atara - 16-4-2018 at 16:00

I had always wondered if you could make this by some sort of elimination on propylene glycol diacetate... which would allow avoiding harsh acetylating agents.

XeonTheMGPony - 16-4-2018 at 16:17


Five studies examined the toxicity of ketene in various animal species. These studies indicate that the inhalation route of exposure is of particular concern for ketene and that the chemical has similarities to phosgene in clinical effects and mode of action. Ketene is a respiratory poison that can exhibit delayed toxicity to alveolar structures (mainly capillaries) to produce death by pulmonary edema. Ketene has been shown to acetylate free amino (and other functional) groups of proteins in aqueous solution. Like phosgene, the pulmonary effects of inhalation exposure to ketene may be manifested in the absence of direct irritation by ketene or its breakdown product, acetic acid. For all species tested, the toxicologic profile of ketene is similar. Ketene is lethal at high concentrations; at lower concentrations, minor irritation during exposure and central nervous system impairment have been observed. However, severe damage to the lungs (at the alveolar level) may manifest as long as 24 h after exposure. The central nervous system effects are likely due to cerebral anoxia secondary to alveolar damage. Toxicity is greatest in mice, followed by rats, guinea pigs, cats, and rabbits. Ketene appears to exhibit a steep concentration-response relationship

AEGL-3 values are based on the mouse studies of Treon et al. (1949). A 50-min exposure to ketene at 50 ppm caused 100% mortality in mice. A 30-min exposure at 23 ppm was lethal to 7/10 mice, but a 2-h exposure at this concentration was 100% lethal. A 4.5-h exposure at 12 ppm (the next lower test concentration) did not result in deaths, but 3/7 mice died during a 5.5-h exposure at the same concentration on the subsequent day of exposure. Because the time of death during the second exposure was not reported, whether the deaths were a delayed effect of the first exposure or caused by the second exposure is uncertain. In a second repeated-exposure study (Treon et al. 1949), no deaths occurred in mice after a single 7-h exposure at 1 ppm and 1/10 mice died 3 days after the tenth exposure. The concentration of 1 ppm was considered a threshold for lethal effects caused by a single exposure to ketene and was chosen as the point of departure for calculating AEGL-3 values. A total uncertainty factor of 10 was used. Mice appeared to be the most susceptible species, so an interspecies factor of 3 was considered adequate to account for interspecies differences. An intraspecies factor of 3 was used because the mode of action (acylation of functional groups on proteins and enzymes in the lung) is not expected to vary greatly among individuals. Human studies examining the toxicity of phosgene, which appears to have a mode of action similar to ketene, did not identify sensitive subpopulations and used an intraspecies uncertainty factor of 3 in the derivation of the AEGL-2 and AEGL-3 values (NRC 2002). AEGL-3 values were derived by time scaling according to the equation Cn × t = k, using default values of n = 3 to extrapolate from longer to shorter durations and n = 1 to extrapolate from shorter to longer durations. The 10-min AEGL-3 value was set equal to the 30-min value because of the uncertainty associated with extrapolating a 7-h point of departure to a 10-min AEGL value

Snippet from link

Seems any short term exposure below 50ppm for a couple hours you'll suffer but live, odor thresh hold is stated to be 12ppm.

So basically get a whiff of it and get the hell out you'll be fine the next day, but if you smell it and hang around, there will be a mess to clean up with your body in the middle of it!

So very nasty stuff but a bit over hyped on lethality, but definitely not a substance to be messed with with out a solid grasp of lab technique!

[Edited on 17-4-2018 by XeonTheMGPony]

[Edited on 17-4-2018 by XeonTheMGPony]

zed - 17-4-2018 at 18:08

The problem is that you can't smell it in low concentrations. But, a few hours of exposure to a low concentration, and you might just go home and die in your sleep.

Traps and a really good hood, will probably protect you.

But hey! It's chemistry. You do your best, and hope you don't occupy the wrong end of the "Bell Curve".

clearly_not_atara - 7-5-2022 at 05:02

The action of excess anhydrous HBr in acetic acid on propylene glycol gives predominantly 2-acetoxy-1-bromopropane. From attached:
The reaction between propane-1,2-diol and HBA is regioselective, giving 94% of 2-acetoxy-1-bromopropane and 6% of 1-acetoxy-2-bromopropane.

Dehydrohalogenation of this product gives the target compound.

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draculic acid69 - 12-5-2022 at 04:03

Quote: Originally posted by zed  

Just bubble your Ketene though Acetone rather than Acetic Acid.

[Edited on 16-4-2018 by zed]

If it's only ketene bubbled thru acetone then perhaps the acetone trap in a ketene generator such as the bulb full of brown acetone in the Doug's lab ketene video could be distilled to recover some isopropenyl acetate possibly as a byproduct of normal ketene process.