Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Pressure-hydrogenation of Organic Compounds by Molybdenum Sulfide Catalyst. XI
Synthesis of Dodecyl mercaptan from Dodecanonitrile
Kunio ITABASHI
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1961 Volume 19 Issue 8 Pages 597-601

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Abstract
Dodecanonitrile in xylene as a solvent and in the presence of sulfur was reduced with molybdenum sulfide catalyst at an initial pressure of hydrogen 100 atmospheres.
The reaction was started at around 150°C and yielded 70-5% dodecylmercaptan at 200-50°C.
The reaction below 200°C left much of unreacted raw material, besides showing much yield of didodecyl disulfide as a by-product, while the reaction above 250°C was accompanied with the cleavage to dodecane and the yield of mercaptan was low.
The results of reaction by using varied amount of sulfur indicated that the yield of mercaptan was increased with an increase of sulfur and it reached a constant value at the molar ratio of 1.5.
The formation of amine was only a small amount in all cases.
The result indicated that the route of reaction is the formation of thioamide from hydrogen sulfide, produced from reduction of sulfur, and the sample, and the mercaptan is presumed to be formed from its reduction.
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© The Society of Syhthetic Organic Chemistry, Japan
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