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Issue 4, 2014
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Streamlining the conversion of biomass to polyesters: bicyclic monomers with continuous flow

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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.

Graphical abstract: Streamlining the conversion of biomass to polyesters: bicyclic monomers with continuous flow

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Publication details

The article was received on 24 Jul 2013, accepted on 11 Nov 2013 and first published on 11 Nov 2013


Article type: Paper
DOI: 10.1039/C3GC41479E
Citation: Green Chem., 2014,16, 1774-1783
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    Streamlining the conversion of biomass to polyesters: bicyclic monomers with continuous flow

    D. Dakshinamoorthy, S. P. Lewis, M. P. Cavazza, A. M. Hoover, D. F. Iwig, K. Damodaran and R. T. Mathers, Green Chem., 2014, 16, 1774
    DOI: 10.1039/C3GC41479E

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