YT2095 Posted January 4, 2006 Posted January 4, 2006 I`ve heard that Acetone in Ethanol will make a Keytone if left to stand over time, is there any truth in this?
stsanthony Posted January 4, 2006 Posted January 4, 2006 i haven't heard of this, but what do you mean about "keytone"? Is that ketone?
YT2095 Posted January 4, 2006 Author Posted January 4, 2006 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.
YT2095 Posted January 4, 2006 Author Posted January 4, 2006 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 Posted January 4, 2006 Posted January 4, 2006 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 Posted January 4, 2006 Author Posted January 4, 2006 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 Posted January 4, 2006 Posted January 4, 2006 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 Posted January 4, 2006 Posted January 4, 2006 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.
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