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 journalArticle

15 Citations (Scopus)

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

Fingerprint

Polyesters
alkene
Biomass
Monomers
catalyst
biomass
Alkenes
Isomerization
recycling
glass
Olefins
Hydrogenation
Maleic Anhydrides
Catalysts
Maleic anhydride
Glycerol
temperature
Byproducts
Recycling
Thermodynamic stability

All Science Journal Classification (ASJC) codes

  • Environmental Chemistry
  • Pollution

Cite this

Dakshinamoorthy, D., Lewis, S. P., Cavazza, M. P., Hoover, A. M., Iwig, D. F., Damodaran, K., & Mathers, R. T. (2014). Streamlining the conversion of biomass to polyesters: Bicyclic monomers with continuous flow. Green Chemistry, 16(4), 1774-1783. https://doi.org/10.1039/c3gc41479e
Dakshinamoorthy, Deivasagayam ; Lewis, Stewart P. ; Cavazza, Michael P. ; Hoover, Aaron M. ; Iwig, David F. ; Damodaran, Krishnan ; Mathers, Robert T. / Streamlining the conversion of biomass to polyesters : Bicyclic monomers with continuous flow. In: Green Chemistry. 2014 ; Vol. 16, No. 4. pp. 1774-1783.
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Dakshinamoorthy, D, Lewis, SP, Cavazza, MP, Hoover, AM, Iwig, DF, Damodaran, K & Mathers, RT 2014, 'Streamlining the conversion of biomass to polyesters: Bicyclic monomers with continuous flow', Green Chemistry, vol. 16, no. 4, pp. 1774-1783. https://doi.org/10.1039/c3gc41479e

Streamlining the conversion of biomass to polyesters : Bicyclic monomers with continuous flow. / Dakshinamoorthy, Deivasagayam; Lewis, Stewart P.; Cavazza, Michael P.; Hoover, Aaron M.; Iwig, David F.; Damodaran, Krishnan; Mathers, Robert T.

In: Green Chemistry, Vol. 16, No. 4, 04.2014, p. 1774-1783.

Research output: Contribution to journalArticle

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Dakshinamoorthy D, Lewis SP, Cavazza MP, Hoover AM, Iwig DF, Damodaran K et al. Streamlining the conversion of biomass to polyesters: Bicyclic monomers with continuous flow. Green Chemistry. 2014 Apr;16(4):1774-1783. https://doi.org/10.1039/c3gc41479e