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. https://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:

URL	URL Type	Description
http://onlinelibrary.wiley.com/doi/10.1002/adsc.201301109/abstract	Publisher	Article
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998208/	PubMed Central	Article

ORCID:

Author	ORCID
Fedorov, Alexey	0000-0001-9814-6726
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 Agency	Grant Number
Resnick Sustainability Institute	UNSPECIFIED
BP XC2 Program	UNSPECIFIED
NIH	R01GM080269
NIH	5R01GM031332-27
Gordon and Betty Moore Foundation	UNSPECIFIED
Caltech Center for Catalysis and Chemical Synthesis	UNSPECIFIED

Subject Keywords:

decarbonylative dehydration; fatty acids; large-scale process; linear alpha olefins; palladium; renewable feedstocks; Z-selective metathesis

Issue or Number:

PubMed Central ID:

PMC3998208

Record Number:

CaltechAUTHORS:20140122-135551444

Persistent URL:

https://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

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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:

07 Jul 2020 20:11

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