Premium
Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes
Author(s) -
Martínez Javier,
CruzMartínez Felipe,
Martínez de Sarasa Buchaca Marc,
FernándezBaeza Juan,
SánchezBarba Luis F.,
North Michael,
CastroOsma José A.,
LaraSánchez Agustín
Publication year - 2021
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202100079
Subject(s) - iminium , triphenylphosphine , catalysis , chemistry , furan , carbonate , isocyanate , organic chemistry , carbon dioxide , epoxide , polymer chemistry , polyurethane
Bio‐derived furan‐ and diacid‐derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO 2 . 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.