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Palladium-Catalyzed Decarbonylative Dehydration of Fatty Acids for the Production of Linear Alpha Olefins

Liu, Yiyang and Kim, Kelly E. and Herbert, Myles B. and Fedorov, Alexey and Grubbs, Robert H. and Stoltz, Brian M. (2014) Palladium-Catalyzed Decarbonylative Dehydration of Fatty Acids for the Production of Linear Alpha Olefins. Advanced Synthesis and Catalysis, 356 (1). pp. 130-136. ISSN 1615-4150. PMCID PMC3998208. http://resolver.caltech.edu/CaltechAUTHORS:20140122-135551444

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Abstract

A highly efficient palladium-catalyzed decarbonylative dehydration reaction of carboxylic acids is reported. This method transforms abundant and renewable even-numbered natural fatty acids into valuable and expensive odd-numbered alpha olefins. Additionally, the chemistry displays a high functional group tolerance. The process employs a low loading of palladium catalyst and proceeds under solvent-free and relatively mild conditions.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://onlinelibrary.wiley.com/doi/10.1002/adsc.201301109/abstractPublisherArticle
http://dx.doi.org/10.1002/adsc.201301109DOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998208/PubMed CentralArticle
ORCID:
AuthorORCID
Fedorov, Alexey0000-0001-9814-6726
Grubbs, Robert H.0000-0002-0057-7817
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2014 Wiley-VCH Verlag GmbH & Co. Received: December 9, 2013; Published online: January 13, 2014. The authors wish to thank the Resnick Sustainability Institute at Caltech (graduate fellowship to Y.L.), BP (postdoctoral fellowship to A.F. under the XC2 program), NIH-NIGMS (R01GM080269, B.M.S.), NIH (NIH 5R01GM031332-27, R.H.G.), the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. Materia, Inc. is thanked for the generous donation of ruthenium catalysts. Dr. David Vander-Velde is acknowledged for NMR spectroscopy assistance. Dr. Mona Shahgholi and Naseem Torian are acknowledged for high-resolution mass spectrometry assistance. Dr. Scott Virgil is acknowledged for helpful discussions.
Group:Resnick Sustainability Institute
Funders:
Funding AgencyGrant Number
Resnick Sustainability InstituteUNSPECIFIED
BP XC2 Program Postdoctoral FellowshipUNSPECIFIED
NIHR01GM080269
NIH5R01GM031332-27
Gordon and Betty Moore FoundationUNSPECIFIED
Caltech Center for Catalysis and Chemical SynthesisUNSPECIFIED
Subject Keywords:decarbonylative dehydration; fatty acids; large-scale process; linear alpha olefins; palladium; renewable feedstocks; Z-selective metathesis
PubMed Central ID:PMC3998208
Record Number:CaltechAUTHORS:20140122-135551444
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20140122-135551444
Official Citation:Liu, Y., Kim, K. E., Herbert, M. B., Fedorov, A., Grubbs, R. H. and Stoltz, B. M. (2014), Palladium-Catalyzed Decarbonylative Dehydration of Fatty Acids for the Production of Linear Alpha Olefins. Adv. Synth. Catal., 356: 130–136. doi: 10.1002/adsc.201301109
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:43475
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:22 Jan 2014 22:21
Last Modified:21 Jul 2017 19:41

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