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Author Topic: Possible route to Dodecanethiol via Sodium Lauryl Sulfate & Thiourea  (Read 59 times)

no1uno

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Possible route to Dodecanethiol via Sodium Lauryl Sulfate & Thiourea
« on: October 30, 2009, 12:26:56 PM »
The easiest to find dodecyl alcohols are the alkoxylated dodecanol/sodium lauryl sulfate (nb. Dodecanol is also known as lauryl alcohol). How to piss off that pesky sulfate? Well, several sources on the web report that lauryl sulfuric acid is highly unstable, giving the free alcohol (which precipitates) and sulfuric acid when autoclaved, so that should provide a reasonable hint.

If  we can get to the dodecanol, then orgsyn have procedures for forming the dodecyl bromide (usual type route, the phosphoric acid/KI route should work too), and from that, the mercaptan (via thiourea).

Why do I want it? Simple, it reportedly allows for almost quantitive demethylations – the same ones previously done with ethanethiol, without the smells normally associated with mercaptans/thiols (think sewage)…

Anyone got anything useful? A useable route to thiourea? Perhaps somewhere useful to find it (PM Please, always love to know)…
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Sedit

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Re: Possible route to Dodecanethiol via Sodium Lauryl Sulfate & Thiourea
« Reply #1 on: October 31, 2009, 02:12:53 AM »
Thiourea can be found in TarnX or what ever its called. Its a silverware polish and it contains thiourea almost exclusivly.

Seeing as the products of the autoclave is the alcohol and H2SO4 in equal molar amounts I would think that bromination should be as simple as adding NaBr and distilling. I don't know the general properties of Lauryl alcohol so obviously some tweeking of the process would be in order but sounds simple enough and high yeilding depending on the yeilds of cleavege.

Sodium Lauryl Sulfate is in damn near everything in small amounts it seems so this should be no problem to get ones hands on it from commercial sources.

Keep us updates on what you find.
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Vesp

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Re: Possible route to Dodecanethiol via Sodium Lauryl Sulfate & Thiourea
« Reply #2 on: November 01, 2009, 09:28:16 PM »
Interesting. Does it have to be Lauryl? or just some other fatty alcohol? It seems to me that a similiar alcohol is free and found in hair conditioner. Probably is quite a pain to separate it all considering the surfactants and other oil and water soluble mess of chemicals that are found in said products.
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no1uno

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Re: Possible route to Dodecanethiol via Sodium Lauryl Sulfate & Thiourea
« Reply #3 on: November 02, 2009, 02:04:59 AM »
Well Lauryl alcohol is the trivial name for 1-dodecanol and 1-dodecanethiol is one of the odourless mercaptans which have been reported to be useful for almost quantitive demethylations

As for sourcing it - yes, it is in soaps & shampoos... I believe it is possible to make soaps & shampoos at home and even order the various chemicals/supplies online?
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Vesp

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Re: Possible route to Dodecanethiol via Sodium Lauryl Sulfate & Thiourea
« Reply #4 on: November 02, 2009, 04:34:02 AM »
Oh yeah, buying it pure is always an option.. and a sensible one in this situation sense it probably has many uses, and isn't watched, etc. I found it online for $30 for 500ml but I'm sure that is a high price and can probably get it for much cheaper.
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