Preparation of Cyclic Urethanes from Amino Alcohols and Carbon Dioxide Using Ionic Liquid Catalysts with Alkali Metal Promoters

doi:10.3390/i7100438

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Int. J. Mol. Sci. 2006, 7(10), 438-450; doi:10.3390/i7100438

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Preparation of Cyclic Urethanes from Amino Alcohols and Carbon Dioxide Using Ionic Liquid Catalysts with Alkali Metal Promoters

Shin-ichiro Fujita * , Hiroshi Kanamaru, Hisanori Senboku and Masahiko Arai

Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan

* Author to whom correspondence should be addressed.

Received: 21 September 2006 / Accepted: 16 October 2006 / Published: 27 October 2006

(This article belongs to the Special Issue Ionic Liquids)

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Abstract: Several ionic liquids were applied as catalysts for the synthesis of cyclicurethanes from amino alcohols and pressurized CO2 in the presence of alkali metalcompounds as promoters. A comparative study was made for the catalytic performanceusing different ionic liquids, substrates, promoters, and pressures. The optimum catalyticsystem was BMIM-Br promoted by K₂CO₃, which, for 1-amino-2-propanol, produced cyclicurethane in 40% yield with a smaller yield of substituted cyclic urea and no oligomericbyproducts. For other amino alcohols, cyclic urethanes, cyclic ureas, and/or undesiredbyproducts were produced in different yields depending on the substrates used. Possiblereaction mechanisms are proposed.

Keywords: cyclic urethane; amino alcohol; carbon dioxide; ionic liquid catalyst; alkali promoter

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MDPI and ACS Style

Fujita, S.-I.; Kanamaru, H.; Senboku, H.; Arai, M. Preparation of Cyclic Urethanes from Amino Alcohols and Carbon Dioxide Using Ionic Liquid Catalysts with Alkali Metal Promoters. Int. J. Mol. Sci. 2006, 7, 438-450.

AMA Style

Fujita S.-I., Kanamaru H., Senboku H., Arai M. Preparation of Cyclic Urethanes from Amino Alcohols and Carbon Dioxide Using Ionic Liquid Catalysts with Alkali Metal Promoters. International Journal of Molecular Sciences. 2006; 7(10):438-450.

Chicago/Turabian Style

Fujita, Shin-ichiro; Kanamaru, Hiroshi; Senboku, Hisanori; Arai, Masahiko. 2006. "Preparation of Cyclic Urethanes from Amino Alcohols and Carbon Dioxide Using Ionic Liquid Catalysts with Alkali Metal Promoters." Int. J. Mol. Sci. 7, no. 10: 438-450.

Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI Publishing, Basel, Switzerland RSS E-Mail Table of Contents Alert