Tungstic Acid–Tributyltin Chloride on a Charcoal Catalyst in the Epoxidation of Alkenes with Hydrogen Peroxide

• Published in: Bulletin of the Chemical Society of Japan Vol. 58; no. 11; pp. 3193 - 3196
• Main Authors: Itoi, Yasushi, Inoue, Masami, Enomoto, Saburo
• Format: Journal Article
• Language: English
• Published: Tokyo The Chemical Society of Japan 01.11.1985; Chemical Society of Japan
• Subjects: Chemistry; Exact sciences and technology; Kinetics and mechanisms; Organic chemistry; Reactivity and mechanisms; Hydrocarbon; Aliphatic compound; Medium effect; Content; Epoxidation; PH; Benzenic compound; Aqueous solution; Hydrogen Peroxides; Supported catalyst; Monocyclic compound; Ethylenic compound
• DOI: 10.1246/bcsj.58.3193
• ISSN: 0009-2673

Several alkenes, such as cyclopentene, cyclohexene, 1-octene, 2-octene, 1-decene, styrene, and 1-methyl-1-cyclohexene, were epoxidized with aqueous (30%) hydrogen peroxide. n-Bu3SuCl was a good co-catalyst of H2WO4 for the selective epoxidation. The conversion was improved by modifying charcoal as the carrier with such alkylating or alkylsilylating agents as N,N-dimethylformamide dibutyl acetal (DMFBA) or N,O-bis(trimethylsilyl)acetamide. Cyclopentene oxide, cyclohexene oxide, and 2-octene oxide were obtained from the corresponding olefins in the good yields of 74, 64, and 76% respectively by using DMFBA-modified charcoal as the support. The epoxidation was first-order with respect to both cyclohexene and H2O2. The apparent activation energy of the epoxidation of cyclohexene was 11.2 kcal/mol.