THE KINETICS OF THE TERTIARY-AMINE-CATALYZED REACTION OF ORGANIC ISOCYANATES WITH THIOLS | Zendy

Yoshio Iwakura | Zendy; Hisao Okada | Zendy

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THE KINETICS OF THE TERTIARY-AMINE-CATALYZED REACTION OF ORGANIC ISOCYANATES WITH THIOLS

Author(s) -

Yoshio Iwakura,

Hisao Okada

Publication year - 1960

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v60-328

Subject(s) - chemistry , tertiary amine , thiophenol , triethylamine , phenylisocyanate , isocyanate , catalysis , ethanethiol , kinetics , organic chemistry , amine gas treating , pyridine , cyclohexylamine , thiol , medicinal chemistry , piperidine , polymer chemistry , chemical kinetics , polyurethane , physics , quantum mechanics

The kinetics of the reactions of isocyanates with thiols in the presence of tertiary amines were examined. The rate of the reaction was of the first order with respect to the concentration of isocyanate, thiol, and tertiary amine. The catalytic action of tertiary amines decreased in the order of triethylenediamine, triethylamine, diethylcyclohexylamine, tributylamine, N-methylmorpholine, pyridine, and quinoline. The relative rate of the reaction of phenylisocyanate with thiols decreased in the order of phenylmethanethiol, 1,4-butanedithiol, 1-butanethiol, 1-dodecanethiol, and thiophenol. The reaction took place more smoothly in strong ionizing solvents. These facts can be explained by the reaction mechanism indicated by the equations [6] to [8].

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