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

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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 languageEnglish
Pages (from-to)460-468
Number of pages9
Issue number3
Publication statusPublished - 11 Mar 2021

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  • carbon dioxide utilization
  • cyclic carbonates
  • lanthanum
  • polyurethanes
  • sustainable catalysis

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