The Trimerization of Isothiocyanates under High Pressure

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Bibliographic Information

Other Title
  • 高圧下でのイソチオシアン酸エステルの三量化反応

Description

The trimerization of methyl isothiocyanate in the presence of triethylamine was accelerated under high pressure to give 1, 3, 5-trimethyl-1, 3, 5-triazine-2, 4, 6(1 H, 3 H, 5 H)-trithione in high yield. Trialkylamines such as triethylamine were good catalyst s of the trimerization under high presssre. Pyridine also catalyzed the trimerization, but '2-methylpyridine and 2, 6-dimethylpyridine had no catalytic activity. The rate of the trimerization of methyl isothiocyanate was proportional to the amount of triethylamine catalyst so far as a limited amount of triethylamine was used. Ethyl isothiocyanate trimerized in high yield on the same reaction conditions as the trimerization of methyl isothiocyanate, however, isothiocyanates having more bulky groups such as propyl, butyl, allyl, phenyl, and cyclohexyl trimerized in poor yields on such reaction conditions. Propyl and butyl isothiocyanates in the presence of DBU trimerized in good yields under 800 MPa at 130 °C f or 20 h. Althouth allyl isothiocyanate, which has a C-C double bond, polymerized by DBU catalyst or at i ncreased temperature, the trimer was obtained in good yield in the presence of triethylamine under 1200 MPa,

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1992 (4), 383-387, 1992-04-10

    The Chemical Society of Japan

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