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

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 t...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 58; no. 11; pp. 3193 - 3196
Main Authors Itoi, Yasushi, Inoue, Masami, Enomoto, Saburo
Format Journal Article
LanguageEnglish
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
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Summary: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.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.58.3193