Branched Diol Monomers from the Sequential Hydrogenation of Renewable Carboxylic Acids

Charles S. Spanjers, Deborah K. Schneiderman, Jay Z. Wang, Jingyu Wang, Marc A. Hillmyer, Kechun Zhang, Paul J. Dauenhauer

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

A prominent challenge in replacing petrochemical polymers with bioderived alternatives is the efficient transformation of biomass into useful monomers. In this work, we demonstrate a practical process for the synthesis of multifunctional alcohols from five- and six-carbon acids using heterogeneous catalysts in aqueous media. Design of this process was guided by thermodynamic calculations, which indicate the need for two sequential high-pressure hydrogenations: one, reduction of the acid to a lactone at high temperature; two, further reduction of the lactone to the corresponding diol or triol at low temperature. For example, the conversion of mesaconic acid into (α or β)-methyl-γ-butyrolactone was achieved with 95 % selectivity at a turnover frequency of 1.2 min−1 over Pd/C at 240 °C. Subsequent conversion of (α or β)-methyl-γ-butyrolactone into 2-methyl-1,4-butanediol was achieved with a yield of 80 % with Ru/C at 100 °C. This process is an efficient method for the production of lactones, diols, and triols, all valuable monomers for the synthesis of bioderived branched polyesters.

Original languageEnglish (US)
Pages (from-to)3031-3035
Number of pages5
JournalChemCatChem
Volume8
Issue number19
DOIs
StatePublished - Oct 6 2016

Fingerprint

Lactones
Carboxylic Acids
Carboxylic acids
triols
carboxylic acids
Hydrogenation
hydrogenation
monomers
Monomers
acids
Acids
Carbon
Polyesters
carbon
polyesters
synthesis
biomass
Petrochemicals
Polymers
Biomass

Keywords

  • biomass
  • diols
  • heterogeneous catalysis
  • polymers
  • sustainable chemistry

Cite this

Branched Diol Monomers from the Sequential Hydrogenation of Renewable Carboxylic Acids. / Spanjers, Charles S.; Schneiderman, Deborah K.; Wang, Jay Z.; Wang, Jingyu; Hillmyer, Marc A.; Zhang, Kechun; Dauenhauer, Paul J.

In: ChemCatChem, Vol. 8, No. 19, 06.10.2016, p. 3031-3035.

Research output: Contribution to journalArticle

Spanjers, Charles S. ; Schneiderman, Deborah K. ; Wang, Jay Z. ; Wang, Jingyu ; Hillmyer, Marc A. ; Zhang, Kechun ; Dauenhauer, Paul J. / Branched Diol Monomers from the Sequential Hydrogenation of Renewable Carboxylic Acids. In: ChemCatChem. 2016 ; Vol. 8, No. 19. pp. 3031-3035.
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