Mono- and tri-ester hydrogenolysis using tandem catalysis. Scope and mechanism

Lohr, Tracy L.; Li, Zhi; Assary, Rajeev S.; Curtiss, Larry A.; Marks, Tobin J.

doi:10.1039/C5EE03256C

Mono- and tri-ester hydrogenolysis using tandem catalysis. Scope and mechanism

Journal Article · Fri Nov 25 23:00:00 EST 2016 · Energy & Environmental Science

DOI:https://doi.org/10.1039/C5EE03256C· OSTI ID:1386764

Lohr, Tracy L. ^[1]; Li, Zhi ^[1]; Assary, Rajeev S. ^[2]; Curtiss, Larry A. ^[3]; Marks, Tobin J. ^[1]

Northwestern Univ., Evanston, IL (United States)
Argonne National Lab. (ANL), Argonne, IL (United States)
Argonne National Lab. (ANL), Argonne, IL (United States). Center for Nanoscale Materials

In this work, the scope and mechanism of thermodynamically leveraged ester RC(O)O–R' bond hydrogenolysis by tandem metal triflate + supported Pd catalysts are investigated both experimentally and theoretically by DFT and energy span analysis. This catalytic system has a broad scope, with relative cleavage rates scaling as, tertiary > secondary > primary ester at 1 bar H₂, yielding alkanes and carboxylic acids with high conversion and selectivity. Benzylic and allylic esters display the highest activity. The rate law is ν = k[M(OTf)_n]¹[ester]⁰[H₂]⁰ with an H/D kinetic isotope effect = 6.5 ± 0.5, implying turnover-limiting C–H scission following C–O cleavage, in agreement with theory. Intermediate alkene products are then rapidly hydrogenated. Applying this approach with the very active Hf(OTf)₄ catalyst to bio-derived triglycerides affords near-quantitative yields of C₃ hydrocarbons rather than glycerol. From model substrates, it is found that RC(O)O–R' cleavage rates are very sensitive to steric congestion and metal triflate identity. For triglycerides, primary/external glyceryl CH₂–O cleavage predominates over secondary/internal CH–O cleavage, with the latter favored by less acidic or smaller ionic radius metal triflates, raising the diester selectivity to as high as 48% with Ce(OTf)₃.

View Accepted Manuscript (DOE)

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Institute for Atom-efficient Chemical Transformations (IACT); Argonne National Laboratory (ANL), Argonne, IL (United States). Laboratory Computing Resource Center (LCRC) and Center for Nanoscale Materials (CNM); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)

Grant/Contract Number:: AC02-06CH11357; AC02-05CH11231

OSTI ID:: 1386764

Alternate ID(s):: OSTI ID: 1253016

Journal Information:: Energy & Environmental Science, Journal Name: Energy & Environmental Science Journal Issue: 2 Vol. 9; ISSN EESNBY; ISSN 1754-5692

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Handbook of Cosmetic Science and Technology Barel, André O.; Paye, Marc; Maibach, Howard I. https://doi.org/10.1201/b15273	book	January 2010
Oxidative Addition of Aryl and Benzyl Trifluoroacetates to Zerovalent Palladium Complexes with Two Modes of C–O Bond Cleavage Processes Nagayama, Kazuhiro; Shimizu, Isao; Yamamoto, Akio Bulletin of the Chemical Society of Japan, Vol. 72, Issue 4 https://doi.org/10.1246/bcsj.72.799	journal	April 1999

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Octanoic acid hydrodeoxygenation over bifunctional Ni/Al-SBA-15 catalysts Baharudin, Khairul Basyar; Arumugam, Mahashanon; Hunns, James Catalysis Science & Technology, Vol. 9, Issue 23 https://doi.org/10.1039/c9cy01710k	journal	January 2019
Selective hydrodeoxygenation of biomass-derived furfural-acetone to prepare 1-octyl acetate Liu, Xuyang; Li, Yanbing; Deng, Jin Green Chemistry, Vol. 21, Issue 16 https://doi.org/10.1039/c9gc01767d	journal	January 2019

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