Sciencemadness Discussion Board


chemx01 - 5-4-2015 at 11:41

I need some diethylsulfide for my synthesis of precious metal complexes but sigma's price is too high. I'm looking for a synthesis, i've searched reaxys and found a couple of them, but probably the easiest one would be reacting ethyl bromide with sodium sulphide.

And so my question is, has anyone done this, what were the conditions? My idea would be make a solution of the sulfide, add some PTC (Bu4NBr) add the bromoethane and stirr, maybe gently reflux, than separate the upper layer, extract...., sounds easy enough, but i'd be happy to read from anyone who's done this.

The other thing is reagrding the smell, is is really that bad, is it like thiols, can it be used in a fumehood without gassing the whole block? With using bleach as a decontaminating agent, is it managable?

The only reference i could fing regarding this route would be this one, though it doesn't list any conditions and i deals with a deuterated version but that's not a problem:

Berkel, Werefridus W. van; Koning, Leo J. de; Nibbering, Nico M. M.
Journal of the American Chemical Society, 1987 , vol. 109, # 25 p. 7602 - 7608

blogfast25 - 5-4-2015 at 13:04

I really don't know much about diethyl sulphide but Wikipedia describes quite a simple preparation (w/o much detail):

Hellafunt - 5-4-2015 at 14:37

It says in the wikipedia article that diethyl sulphide is the chemical responsible for the smell of a durian, so I would be scared of "gassing the whole block!"

kavu - 6-4-2015 at 00:53

I have had the displeasure of working with this particular thioether. The foul smell is very pungent in ever so tiny amounts escaped from the apparatus. My advice: Do not work with/synthesize this compound unless absolutely necessary.

chemx01 - 6-4-2015 at 04:16

Thanks everyone for their opinons, i have found an excellent alternative which should work.

My new question is is anyone familiar with the smell of Methionine, does it smell at all?

DraconicAcid - 6-4-2015 at 07:30

I generally assume that if it has C-S or H-S bonds, and a boiling point of under 150oC, it's probably going to reek. Carbon disulphide is said to be odourless when absolutely pure, but it's rarely that pure.

Metacelsus - 6-4-2015 at 09:19

I've used carbon disulfide before, and it doesn't smell that bad. Carbonyl sulfide, on the other hand, absolutely reeks.

Dr.Bob - 6-4-2015 at 10:41

Methionine is polar enough to not smell too bad. It is also easier to get hold of and non-toxic, so it is ideal. It is even used as a dog food additive in small amounts.