Multifunctional Cascade Catalysis of Itaconic Acid Hydrodeoxygenation to 3-Methyl-tetrahydrofuran

Dae Sung Park, Omar A. Abdelrahman, Katherine P. Vinter, Patrick M. Howe, Jesse Quentin Bond, Theresa M. Reineke, Kechun Zhang, Paul J. Dauenhauer

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Hybrid production of isoprene from biomass-derived sugar as a feedstock for renewable rubber is a three-part process comprising glucose fermentation to itaconic acid, liquid-phase hydrodeoxygenation to 3-methyl-tetrahydrofuran, followed by vapor-phase dehydra-decyclization to isoprene. Here, we investigate a multifunctional catalyst design for itaconic acid hydrodeoxygenation to 3-methyl-tetrahydrofuran. The production of 3-methyl-tetrahydrofuran from itaconic acid is a multistep process involving hydrogenation, acid-catalyzed dehydration, and hydrodeoxygenation of multiple organic functionalities. A detailed kinetic analysis of this multistep reaction network over a Pd/C catalyst revealed a kinetic bottleneck in the reduction of methyl-γ-butyrolactone to 1,4-methylbutanediol, which was accelerated through the use of Re as an oxophillic promoter. Varying ratios of Pd:Re indicated a maximum overall rate of lactone ring opening with a 3.5:1.0 Pd:Re ratio, likely due to the combined capability of Pd to hydrogenate double bonds and Re to open the lactone ring. Applying this insight, the overall rate of itaconic acid hydrodeoxygenation to 3-methyl-tetrahydrofuran increased by more than an order of magnitude.

Original languageEnglish (US)
Pages (from-to)9394-9402
Number of pages9
JournalACS Sustainable Chemistry and Engineering
Volume6
Issue number7
DOIs
StatePublished - Jul 2 2018

Keywords

  • 3-Methyl-tetrahydrofuran
  • Bimetallic
  • Biomass
  • Hydrogenation
  • Isoprene
  • Itaconic acid

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

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  • Cite this

    Park, D. S., Abdelrahman, O. A., Vinter, K. P., Howe, P. M., Bond, J. Q., Reineke, T. M., Zhang, K., & Dauenhauer, P. J. (2018). Multifunctional Cascade Catalysis of Itaconic Acid Hydrodeoxygenation to 3-Methyl-tetrahydrofuran. ACS Sustainable Chemistry and Engineering, 6(7), 9394-9402. https://doi.org/10.1021/acssuschemeng.8b01743