[klone]

Hi everybody

A kind help would be strongly appreciated!

In many books of Organic Chemistry, a typical example of SN2 reaction is the formation of ethanol starting from chloroethane reacting with NaOH in water solutions.
But, as far as I trying, I cannot find papers publishing experimental kinetic data of such a simple reaction.
Probably I was not so good in searching … and it be great if someone could quote some old reference to me.
Many thanks in advance!!!

[Babcock_Hall]

Which search engines have you used?  Which books or journals have you checked, so far?

[klone]

I was googling opening many pages and links.
and Scifinder.

US283811 the only doc related

thks

[pgk]

Theoretically, ethanol can be prepared by a SN2 reaction of NaOH with chloroethane and thus, the method is cited in some textbooks. But this method has no practical value because ethanol is industrially prepared by low cost, fermentation methods or by large scale, petrochemical methods starting from acetylene or ethylene. So, nobody is interested to publish or claim anything about a SN2 synthesis of ethanol.
Note: US Patent 283811 is published in 1883, refers to a “two wheeled vehicle” and has nothing to do with the issue.

[klone]

Hi thanks for the reply!
Sorry for my typo ... US2832811 is the right one.

But IMHO I don't think literature only shows data of reactions of practical/commercial interest.
In this case, probably there's something studied in the beginning of 1900 ...

[pgk]

US Patent 2832811 (1958) claims a method of purifying light hydrocarbons by removing ethyl chloride impurity, using its alkaline hydrolysis that leads to the formation of ethanol as a byproduct; but the method is not claimed for the preparation of ethanol.
Nevertheless, literature is roughly divided in three groups:
a). Books that describe the theoretical basis and the progress of Science, regardless their practical/economical interest.
b). Scientific articles that announce the novelties in Pure and/or Applied Science, in preference but not limited to if having a practical/economical interest. However, it is unlike to often see scientific articles (even, older ones) about the preparation of an alcohol from the hazardous, pollutant and more expensive, corresponding alkyl halide; except/may be in Radiochemistry.
c). Patents that claim novelties in scientific and technical fields, only of practical/technical/economical interest.

[klone]

Hi everybody

US5969195 shows how sometimes (by products) process streams could be re-utilized. In this cas exploiting SN2 reaction of the topic with some experimental data on mileage conversion at 150°C.
This is not the foundamental expression of kinetic data is was looking for but at least an indication of the reaction rates.

[pgk]

The reaction works perfectly but it is anti-economical for industrial application. Besides, US Patent 5969195, (1999) mainly claims a method of detoxication/ remediation of wastes from chlorine petrochemical procedures, by transformation of alkyl monochlorides to the corresponding alcohols, similarly as the already expired US Patent 2832811 (1958).