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

Martinez, Javier; de la Cruz-Martinez, Felipe; Martinez de Sarasa Buchaca, Marc; Fernandez-Baeza, Juan; Sanchez-Barba, Luis F.; North, Michael; Castro-Osma, Jose A.; Lara-Sanchez, Agustin

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 degrees 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.

Más información

Título según WOS: Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes
Título de la Revista: CHEMPLUSCHEM
Volumen: 86
Número: 3
Editorial: WILEY-V C H VERLAG GMBH
Fecha de publicación: 2021
Página de inicio: 460
Página final: 468
DOI:

10.1002/CPLU.202100079

Notas: ISI