Keytones

[YT2095]

I`ve heard that Acetone in Ethanol will make a Keytone if left to stand over time, is there any truth in this?

[stsanthony]

i haven't heard of this, but what do you mean about "keytone"? Is that ketone?

[YT2095]

what i mean is that acetone is itself a keytone, but when mixed with ethanol and left to stand, it apparently forms another type of keytone.

I want to know if this is true, and what it`s called, so then I can find out about its ability to absorb water from the air.

[stsanthony]

well, if yes, it may be fragmentation

[YT2095]

huh?

 

my guess is that it forms MEK, but i can`t be 100% certain.

 

take a look here: http://www.pureenergysystems.com/news/2005/03/17/6900069_Acetone/

that`s why I`m asking, some fuels contain ethanol.

[RyanJ]

Well... ketones can be created by oxidation of secondary alcohols but it requires a very strong oxidant such as Potassiun Dichromate to make it occur...

 

I'm not shure if just leaving it in the open would work though :S

 

Cheers,

 

Ryan Jones

[YT2095]

well basicly what I heard was that the addition of acetone to petrol was fine (even a benefit) but some fuels contain ethanol, and it`s still ok to add acetone to this, but not to leave it standing unused for any length of time as it`ll form a ketone and absorb water from the air.

[RyanJ]

well basicly what I heard was that the addition of acetone to petrol was fine (even a benefit) but some fuels contain ethanol, and it`s still ok to add acetone to this, but not to leave it standing unused for any length of time as it`ll form a ketone and absorb water from the air.

 

I'm afraid what I posted is as much as I know....

 

Here are some links that may help you though

 

http://tellurium.chem.ox.ac.uk/Ketones/defaultf.html

http://en.wikipedia.org/wiki/Ketone

http://chemed.chem.purdue.edu/genchem/topicreview/bp/2organic/aldehyde.html

http://ull.chemistry.uakron.edu/genobc/Chapter_14/

 

Cheers,

 

Ryan Jones

[budullewraagh]

i just played around with a few mechanisms and i found something interesting and mostly unrelated. if there is a reaction between ethanol and acetone, the interactin is between the lone pair of the ethanol's O and the pi antibonding orbital of the middle carbon in acetone, bringing the pi bonding electrons from C=O to form C-O- and leaving the EtOH+ bonded to the middle carbon of the former ketone. well, the O- could just perform a lone pair push to get rid of the EtOH+, but if another EtOH takes the proton off of the EtOH+ group before this push can occur (imagine doing this in slightly alkaline conditions), the push will not occur, as the methoxide anion is a terrible leaving group. This said, it is now possible for the still negative oxygen to perform a nucleophilic attack on the previously formed EtOH2+, forming an interestingly symmetrical acetal, 2,2 diethoxy propane.

 

but anyway, i have class in about 5 minutes.

 

btw i came to the conclusion that atmospheric oxygen must be involved in your reaction, yt, as the HOMO/LUMO interactions between EtOH and acetone would undoubtedly result in the first intermediate described above.