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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 10
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Original Articles

Organic Preparations with Molar Amounts of Volatile Malodorous Thiols

, &
Pages 1447-1454 | Received 06 Sep 2011, Published online: 05 Mar 2013
 

Abstract

Thiols are indispensable for the preparation of many organic sulfur compounds. Their strong smell and use for gas leakage perception render it almost impossible to work with them without arousing public attention. Molar amounts of the very odoriferous thiol 2-methyl-2-propanethiol (t-butylthiol) are needed, for example, for the large-scale synthesis of two useful synthetic building blocks, 1,2,4,5-tetrakis(t-butylthio)benzene and tetramethylbenzo-2,2,6,6-[1,2-d;4,5-d']bis[1,3]dithiol. We investigated an array of alternatives to circumvent the problem: (1) alternative thiols (primary, long-chain, tertiary thiols of larger molar mass); (2) exhaust cleaning methods (adsorption, oxidation, conversion to a salt); and (3) thermal exhaust treatment. Only combustion of the fumehood exhaust with domestic gas at 900 °C in a regenerative thermal oxidation unit was able to completely prevent the thiol smell from escaping.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

GRAPHICAL ABSTRACT

Notes

a Scheme , method a.

b Scheme , method b.

c Synthesis according to Ref. 22.

d Synthesis according to Ref. 23.

e Un-identifiable product mixture.

f Not synthesized, thiol smell much too storng.

g Not synthesized, thiol insoluble in toluene.

h Synthesis according to Ref. 31.

i Incomplete substitution.

j Not synthesized.

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