Renewable Isoprene by Sequential Hydrogenation of Itaconic Acid and Dehydra-Decyclization of 3-Methyl-Tetrahydrofuran

Omar A. Abdelrahman; Dae Sung Park; Katherine P. Vinter; Charles S. Spanjers; Limin Ren; Hong Je Cho; Kechun Zhang; Wei Fan; Michael Tsapatsis; Paul J. Dauenhauer

doi:10.1021/acscatal.6b03335

Renewable Isoprene by Sequential Hydrogenation of Itaconic Acid and Dehydra-Decyclization of 3-Methyl-Tetrahydrofuran

Omar A. Abdelrahman, Dae Sung Park, Katherine P. Vinter, Charles S. Spanjers, Limin Ren, Hong Je Cho, Kechun Zhang, Wei Fan, Michael Tsapatsis, Paul J. Dauenhauer

Chemical Engineering and Materials Science

Research output: Contribution to journal › Article › peer-review

69 Scopus citations

Abstract

Catalytic hydrogenation of itaconic acid (obtained from glucose fermentation) yields 3-methyl-tetrahydrofuran (3-MTHF), which then undergoes catalytic dehydra-decyclization to isoprene. It is demonstrated that a one-pot cascade reaction converts itaconic acid to 3-MTHF at ∼80% yield with Pd-Re/C catalyst and 1000 psig H₂. Subsequent gas-phase catalytic ring opening and dehydration of 3-MTHF with phosphorus-containing zeolites including P-BEA, P-MFI, and P-SPP (self-pillared pentasil) exhibits 90% selectivity to dienes (70% isoprene, 20% pentadienes) at 20-25% conversion.

Original language	English (US)
Pages (from-to)	1428-1431
Number of pages	4
Journal	ACS Catalysis
Volume	7
Issue number	2
DOIs	https://doi.org/10.1021/acscatal.6b03335
State	Published - Feb 3 2017

Bibliographical note

Funding Information:
This work was supported by the National Science Foundation through the University of Minnesota Center for Sustainable Polymers under award number CHE-1413862.

Publisher Copyright:
© 2017 American Chemical Society.

Keywords

hydrogenation
isoprene
itaconic acid
phosphorus
zeolite

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title = "Renewable Isoprene by Sequential Hydrogenation of Itaconic Acid and Dehydra-Decyclization of 3-Methyl-Tetrahydrofuran",

abstract = "Catalytic hydrogenation of itaconic acid (obtained from glucose fermentation) yields 3-methyl-tetrahydrofuran (3-MTHF), which then undergoes catalytic dehydra-decyclization to isoprene. It is demonstrated that a one-pot cascade reaction converts itaconic acid to 3-MTHF at ∼80% yield with Pd-Re/C catalyst and 1000 psig H2. Subsequent gas-phase catalytic ring opening and dehydration of 3-MTHF with phosphorus-containing zeolites including P-BEA, P-MFI, and P-SPP (self-pillared pentasil) exhibits 90% selectivity to dienes (70% isoprene, 20% pentadienes) at 20-25% conversion.",

keywords = "hydrogenation, isoprene, itaconic acid, phosphorus, zeolite",

author = "Abdelrahman, {Omar A.} and Park, {Dae Sung} and Vinter, {Katherine P.} and Spanjers, {Charles S.} and Limin Ren and Cho, {Hong Je} and Kechun Zhang and Wei Fan and Michael Tsapatsis and Dauenhauer, {Paul J.}",

note = "Funding Information: This work was supported by the National Science Foundation through the University of Minnesota Center for Sustainable Polymers under award number CHE-1413862. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acscatal.6b03335",

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T1 - Renewable Isoprene by Sequential Hydrogenation of Itaconic Acid and Dehydra-Decyclization of 3-Methyl-Tetrahydrofuran

AU - Abdelrahman, Omar A.

AU - Park, Dae Sung

AU - Vinter, Katherine P.

AU - Spanjers, Charles S.

AU - Ren, Limin

AU - Cho, Hong Je

AU - Zhang, Kechun

AU - Fan, Wei

AU - Tsapatsis, Michael

AU - Dauenhauer, Paul J.

N1 - Funding Information: This work was supported by the National Science Foundation through the University of Minnesota Center for Sustainable Polymers under award number CHE-1413862. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/2/3

Y1 - 2017/2/3

N2 - Catalytic hydrogenation of itaconic acid (obtained from glucose fermentation) yields 3-methyl-tetrahydrofuran (3-MTHF), which then undergoes catalytic dehydra-decyclization to isoprene. It is demonstrated that a one-pot cascade reaction converts itaconic acid to 3-MTHF at ∼80% yield with Pd-Re/C catalyst and 1000 psig H2. Subsequent gas-phase catalytic ring opening and dehydration of 3-MTHF with phosphorus-containing zeolites including P-BEA, P-MFI, and P-SPP (self-pillared pentasil) exhibits 90% selectivity to dienes (70% isoprene, 20% pentadienes) at 20-25% conversion.

AB - Catalytic hydrogenation of itaconic acid (obtained from glucose fermentation) yields 3-methyl-tetrahydrofuran (3-MTHF), which then undergoes catalytic dehydra-decyclization to isoprene. It is demonstrated that a one-pot cascade reaction converts itaconic acid to 3-MTHF at ∼80% yield with Pd-Re/C catalyst and 1000 psig H2. Subsequent gas-phase catalytic ring opening and dehydration of 3-MTHF with phosphorus-containing zeolites including P-BEA, P-MFI, and P-SPP (self-pillared pentasil) exhibits 90% selectivity to dienes (70% isoprene, 20% pentadienes) at 20-25% conversion.

KW - hydrogenation

KW - isoprene

KW - itaconic acid

KW - phosphorus

KW - zeolite

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Renewable Isoprene by Sequential Hydrogenation of Itaconic Acid and Dehydra-Decyclization of 3-Methyl-Tetrahydrofuran

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