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
![]() |
PDF
- Accepted Version
See Usage Policy. 1MB | |
|
PDF
- Supplemental Material
See Usage Policy. 2MB |
Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20140122-135551444
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: |
| ||||||||||||||
ORCID: |
| ||||||||||||||
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: |
| ||||||||||||||
Subject Keywords: | decarbonylative dehydration; fatty acids; large-scale process; linear alpha olefins; palladium; renewable feedstocks; Z-selective metathesis | ||||||||||||||
Issue or Number: | 1 | ||||||||||||||
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 | ||||||||||||||
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: | 07 Jul 2020 20:11 |
Repository Staff Only: item control page