Sciencemadness Discussion Board

Hexanol from Hexane

Meltonium - 27-9-2016 at 17:26

So I have this 1 liter bottle of hexane just sitting in my refrigerator and was wondering if I could make some hexanol from it. Unfortunately, I do not have much knowledge of organic chemistry, can I do this easily? If so how?

Maroboduus - 27-9-2016 at 17:41

Do you just mean any old hexanol, or some specific hexanol? This makes a bit of a difference.

Even more so since your hexane may be a mixture of hexane isomers.

Meltonium - 27-9-2016 at 18:01

Oh yeah that does make a difference. I'm thinking of 1, hexanol (I think; this nomenclature is still new to me). Also the supplier I bought the hexane from assures me it's n-hexane.

Maroboduus - 27-9-2016 at 18:37

You sure got me there. All I can think of is halogenation and hydrolysis, which would give you some random oh group on the chain, but I don't know HOW you'd get it at one end. probably somebody more experienced will straighten this out, and I'll be looking on with interest.
All that occurs to me is maybe you could dissolve it in carbon tetrachloride and use molecular sieves of the right size to bind up most of the hexane molecule to make terminal halogenation more likely. That's a total shot in the dark though.

I'm guessing you'd have an easier time making it out of goat's milk.

Sorry I can't be of more help.

Metacelsus - 27-9-2016 at 18:43

I wouldn't store n-hexane in a normal refrigerator. First, it's metabolized to a neurotoxin (2,5-hexanedione), so you don't want to store it with food. Second, you need a specially designed refrigerator to store flammable, volatile chemicals. Standard refrigerators can produce sparks and cause explosions.

Also, there's no easy way I can think of to selectively introduce an alcohol at the 1-position of hexane.

CuReUS - 28-9-2016 at 04:29

there are some methods ,but like metacelsus mentioned,they aren't easy

http://onlinelibrary.wiley.com/doi/10.1002/1521-3773(2000070...
http://pubs.rsc.org/en/content/articlelanding/2001/p2/b10144...
http://www.sciencedirect.com/science/article/pii/S0040403901...
http://www.sciencedirect.com/science/article/pii/S0021951706...
http://www.sciencedirect.com/science/article/pii/S0040403900...
http://pubs.rsc.org/en/content/articlelanding/2011/ob/c1ob05...

the last one gives only 1-hexanol ,if you can get the enzyme ;)