Synthesis of 5- to 8-membered cyclic carbonates from diols and CO2: A one-step, atmospheric pressure and ambient temperature procedure

Thomas M. McGuire, Eva M. López-Vidal, Georgina L. Gregory, Antoine Buchard

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Abstract

6-, 7- and 8-membered ring cyclic carbonates are of particular interest as monomers for ring-opening polymerisation towards more sustainable polymers. They are traditionally synthesised from diols and phosgene derivatives, and while alternative CO2 methods exist to make 5- and 6-membered cyclic carbonates, there is no report of the synthesis of 7- and 8-membered cyclic carbonates made directly from CO2. Herein we report an efficient one-pot synthesis of cyclic carbonates which uses diols, CO2, tosyl chloride and mild bases (NEt3 or TMP), under ambient temperature and 1 atm of CO2 pressure. Fifteen cyclic carbonates were synthesised, including twelve known monomers, and the first examples of 7- and 8-membered cyclic carbonates made using CO2.

Original languageEnglish
Pages (from-to)283-288
Number of pages6
JournalJournal of CO2 Utilization
Volume27
Early online date15 Aug 2018
DOIs
Publication statusPublished - 1 Oct 2018

Funding

The EPSRC (EP/N022793/1; EP/L016354/1/CDT in Sustainable Chemical Technologies) , Roger and Sue Whorrod (fellowship to AB) and the Royal Society (UF/160021 fellowship to AB) are acknowledgedfor research funding. We thank the University of Bath HPC for computing resources. Analytical facilities were provided through the Chemical Characterisation and Analysis Facility (CCAF) at the University of Bath ( www.bath.ac.uk/ccaf ). Appendix C

Keywords

  • Carbon dioxide
  • Cyclic carbonates
  • Cyclization
  • Diols
  • Monomers

ASJC Scopus subject areas

  • Chemical Engineering (miscellaneous)
  • Waste Management and Disposal
  • Process Chemistry and Technology

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