γ-Ketosulfides and Hydroxysulfides from Sodium Methanthiolate of Sulfidic Spent Caustics

Condensation of pentan-3-one, hexan-2-one, 4-methylpentan-2-one, 5-methylhexan-3-one, or 2,6-dimethylheptan-4-one with formaldehyde and sodium methanethiolate, which is present in sulfidic spent caustic from the Orenburg gas processing plant, yields the corresponding mono- and bis[(methylsulfanyl)me...

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Bibliographic Details
Published in:Petroleum chemistry 2019-06, Vol.59 (6), p.615-621
Main Authors: Baeva, L. A., Biktasheva, L. F., Fatykhov, A. A., Lyapina, N. K.
Format: Article
Language:English
Subjects:
Alkalies
Chemistry
Chemistry and Materials Science
Formaldehyde
Industrial Chemistry/Chemical Engineering
Ketones
Reagents
Sodium
Substitutes
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Summary:Condensation of pentan-3-one, hexan-2-one, 4-methylpentan-2-one, 5-methylhexan-3-one, or 2,6-dimethylheptan-4-one with formaldehyde and sodium methanethiolate, which is present in sulfidic spent caustic from the Orenburg gas processing plant, yields the corresponding mono- and bis[(methylsulfanyl)methyl]-substituted ketones or their mixtures depending on the reactant ketone structure. Alkylthiomethylation of butan-2-one with equimolar amounts of formaldehyde and sodium methanethiolate results in 3-methyl-5-thiahexan-2-one or, in the case of a twofold excess of the reagents, in 2-methyl-1,5-bis(methylsulfanyl)-4-[(methylsulfanyl)methyl]pentan-3-one. On the basis of 3-methyl-5-thiahexan-2-one, new polyfunctional [(methylsulfanyl)methyl]-substituted alcohol, α-hydroxymethylketone, 1,3-diol, and 1,3-dioxane have been obtained.
ISSN:0965-5441
1555-6239
DOI:10.1134/S0965544119060045