Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes

Javier Martínez; Felipe de la Cruz-Martínez; Marc Martínez de Sarasa Buchaca; Juan Fernández-Baeza; Luis F. Sánchez-Barba; Michael North; José A. Castro-Osma; Agustín Lara-Sánchez

doi:10.1002/cplu.202100079

Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes

Javier Martínez, Felipe de la Cruz-Martínez, Marc Martínez de Sarasa Buchaca, Juan Fernández-Baeza, Luis F. Sánchez-Barba, Michael North, José A. Castro-Osma, Agustín Lara-Sánchez

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Bio-derived furan- and diacid-derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO2 . Furthermore, four highly substituted terpene-derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10-undecenoic acid under mild reaction conditions were prepared, providing the corresponding carbonate products in excellent yields. The catalyst system also performed the conversion of an epoxidized fatty acid n-pentyl ester into a cyclic carbonate under relatively mild reaction conditions (80 °C, 20 bar, 24 h). This bis(cyclic carbonate) was obtained in high yields and with different cis/trans ratios depending on the co-catalyst used. An allyl alcohol by-product was only observed as a minor product when bis(triphenylphosphine)iminium chloride was used as co-catalyst. Finally, two cyclic carbonates were used as building blocks for the preparation of non-isocyanate poly(hydroxy)urethanes by reaction with 1,4-diaminobutane.

Original language	English
Pages (from-to)	460-468
Number of pages	9
Journal	ChemPlusChem
Volume	86
Issue number	3
DOIs	https://doi.org/10.1002/cplu.202100079
Publication status	Published - 11 Mar 2021

Bibliographical note

Publisher Copyright:
© 2021 Wiley-VCH GmbH.

Copyright:
This record is sourced from MEDLINE/PubMed, a database of the U.S. National Library of Medicine

Keywords

carbon dioxide utilization
cyclic carbonates
lanthanum
polyurethanes
sustainable catalysis

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10.1002/cplu.202100079

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Martínez, J., de la Cruz-Martínez, F., Martínez de Sarasa Buchaca, M., Fernández-Baeza, J., Sánchez-Barba, L. F., North, M., Castro-Osma, J. A., & Lara-Sánchez, A. (2021). Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes. ChemPlusChem, 86(3), 460-468. https://doi.org/10.1002/cplu.202100079

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abstract = "Bio-derived furan- and diacid-derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO2 . Furthermore, four highly substituted terpene-derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10-undecenoic acid under mild reaction conditions were prepared, providing the corresponding carbonate products in excellent yields. The catalyst system also performed the conversion of an epoxidized fatty acid n-pentyl ester into a cyclic carbonate under relatively mild reaction conditions (80 °C, 20 bar, 24 h). This bis(cyclic carbonate) was obtained in high yields and with different cis/trans ratios depending on the co-catalyst used. An allyl alcohol by-product was only observed as a minor product when bis(triphenylphosphine)iminium chloride was used as co-catalyst. Finally, two cyclic carbonates were used as building blocks for the preparation of non-isocyanate poly(hydroxy)urethanes by reaction with 1,4-diaminobutane.",

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Martínez, J, de la Cruz-Martínez, F, Martínez de Sarasa Buchaca, M, Fernández-Baeza, J, Sánchez-Barba, LF, North, M , Castro-Osma, JA & Lara-Sánchez, A 2021, 'Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes', ChemPlusChem, vol. 86, no. 3, pp. 460-468. https://doi.org/10.1002/cplu.202100079

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AU - Fernández-Baeza, Juan

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AU - Castro-Osma, José A.

AU - Lara-Sánchez, Agustín

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AB - Bio-derived furan- and diacid-derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO2 . Furthermore, four highly substituted terpene-derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10-undecenoic acid under mild reaction conditions were prepared, providing the corresponding carbonate products in excellent yields. The catalyst system also performed the conversion of an epoxidized fatty acid n-pentyl ester into a cyclic carbonate under relatively mild reaction conditions (80 °C, 20 bar, 24 h). This bis(cyclic carbonate) was obtained in high yields and with different cis/trans ratios depending on the co-catalyst used. An allyl alcohol by-product was only observed as a minor product when bis(triphenylphosphine)iminium chloride was used as co-catalyst. Finally, two cyclic carbonates were used as building blocks for the preparation of non-isocyanate poly(hydroxy)urethanes by reaction with 1,4-diaminobutane.

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Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes

Abstract

Bibliographical note

Keywords

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