Streamlining the conversion of biomass to polyesters: Bicyclic monomers with continuous flow

Deivasagayam Dakshinamoorthy, Stewart P. Lewis, Michael P. Cavazza, Aaron M. Hoover, David F. Iwig, Krishnan Damodaran, Robert T. Mathers

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

A three-step transformation of 1,4-cyclohexadiene (1,4-CHD) using continuous flow produced an aliphatic bicyclic monomer for polyester synthesis. The monomer synthesis involved catalytic alkene isomerization of 1,4-CHD to 1,3-CHD using a heterogeneous Na2O/Na/Al2O3 catalyst, a Diels Alder reaction with maleic anhydride, and hydrogenation of the bicyclic monomer. A partially continuous strategy was compared with a fully continuous method. The continuous flow process streamlined the transformation of waste by-product biomass by minimizing workup procedures and reducing the synthesis time from ∼1 day for batch processes to ∼2.5 h. The monomer synthesis was easily scalable and allowed recycling of the catalysts for alkene isomerization and hydrogenation. The resulting bicyclic monomers were polymerized with glycerol and 1,4-butanediol (BDO) to obtain renewable polyesters with high thermal stability and tunable glass transition temperatures.

Original languageEnglish (US)
Pages (from-to)1774-1783
Number of pages10
JournalGreen Chemistry
Volume16
Issue number4
DOIs
StatePublished - Apr 2014

All Science Journal Classification (ASJC) codes

  • Environmental Chemistry
  • Pollution

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