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

5 Citations (Scopus)

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

Fingerprint

catalysis
Catalysis
Acids
acid
Lactones
Isoprene
isoprene
Catalysts
Kinetics
catalyst
Rubber
kinetics
Dehydration
Sugars
Fermentation
Feedstocks
Hydrogenation
Biomass
rubber
dehydration

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

Cite this

Multifunctional Cascade Catalysis of Itaconic Acid Hydrodeoxygenation to 3-Methyl-tetrahydrofuran. / Park, Dae Sung; Abdelrahman, Omar A.; Vinter, Katherine P.; Howe, Patrick M.; Bond, Jesse Quentin; Reineke, Theresa M.; Zhang, Kechun; Dauenhauer, Paul J.

In: ACS Sustainable Chemistry and Engineering, Vol. 6, No. 7, 02.07.2018, p. 9394-9402.

Research output: Contribution to journalArticle

Park, DS, Abdelrahman, OA, Vinter, KP, Howe, PM, Bond, JQ, Reineke, TM, Zhang, K & Dauenhauer, PJ 2018, 'Multifunctional Cascade Catalysis of Itaconic Acid Hydrodeoxygenation to 3-Methyl-tetrahydrofuran', ACS Sustainable Chemistry and Engineering, vol. 6, no. 7, pp. 9394-9402. https://doi.org/10.1021/acssuschemeng.8b01743
Park, Dae Sung ; Abdelrahman, Omar A. ; Vinter, Katherine P. ; Howe, Patrick M. ; Bond, Jesse Quentin ; Reineke, Theresa M. ; Zhang, Kechun ; Dauenhauer, Paul J. / Multifunctional Cascade Catalysis of Itaconic Acid Hydrodeoxygenation to 3-Methyl-tetrahydrofuran. In: ACS Sustainable Chemistry and Engineering. 2018 ; Vol. 6, No. 7. pp. 9394-9402.
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