Thermal degradation of bis (2-chloroethyl) sulfide (mustard gas)

Article abstract of DOI:10.1080/10426509908031618

The thermal degradation of mustard gas (ClCH₂CH₂SCH₂CH₂Cl, HD ), with and without 5% added water, is examined. GC/MS, LC/MS and NMR were employed to comprehensively analyze the products. After 75 days at 90°C, 91% HD remains (80% with 5% water). After 40 days at 140°C, 30% HD remains (24% with 5% water) and black tar precipitates form. The apparent E_a is 22.4 kcal/mol. Major products include Q (ClCH₂CH₂SCH₂CH₂SCH₂CH₂Cl), 1,2-dichloroethane, polysulfides and 1,4-dithiane. With 5% water, oxygenates such as 1,4-thioxane and 2-chloroethanol are produced as are numerous sulfonium ions, including S-(2-chlorethyl)-1,4-dithianium, a major component of mustard heels. The decomposition does not go to completion due to the equilibrium nature of the reaction at these temperatures.

Full text of DOI:10.1080/10426509908031618

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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THERMAL DEGRADATION OF
BIS (2-CHLOROETHYL) SULFIDE
(MUSTARD GAS)
George W. Wagner a , Brian K. Maciver b , Dennis K.
Rohrbaugh b & Yu-Chu Yang b c
a Geo-Centers, Inc. , Gunpowder Branch Box 68,
Aberdeen Proving Ground, MD, 21010-0068
b Reseach and Technology Directorate, U.S. Army
ERDEC , Aberdeen Proving Ground, MD, 21010
c U.S. Army European Research Office , USARDSG-
UK, PSC 802 Box 15, FPO, AE, 09499-1500
Published online: 24 Sep 2006.
To cite this article: George W. Wagner , Brian K. Maciver , Dennis K. Rohrbaugh & Yu-
Chu Yang (1999) THERMAL DEGRADATION OF BIS (2-CHLOROETHYL) SULFIDE (MUSTARD
GAS), Phosphorus, Sulfur, and Silicon and the Related Elements, 152:1, 65-76, DOI:
10.1080/10426509908031618
To link to this article: http://dx.doi.org/10.1080/10426509908031618
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