Cross metathesis approach to C11-C13 fatty-chain amino esters from oleic acid derivatives

Yamamoto, Kana; Viamajala, Sridhar; Varanasi, Sasidhar; Nguyen, Kim; Abel, Godwin; Mudiyanselage, Ajith Yapa

Title: Cross metathesis approach to C11-C13 fatty-chain amino esters from oleic acid derivatives

Patent · Tue Oct 02 00:00:00 EDT 2018

OSTI ID:1492012

Yamamoto, Kana; Viamajala, Sridhar; Varanasi, Sasidhar; Nguyen, Kim; Abel, Godwin; Mudiyanselage, Ajith Yapa

A concise method of producing nylon 11, 12, or 13 precursors from oleic acid or an ester of oleic acid is described. The method involves cross-metathesis reactions as the key C--C bond formation step. Subsequent steps are provided to convert the metathesis product to the corresponding nylon precursors. Also provided are the products of the method.

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Research Organization:: The University of Toledo; Toledo, OH (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: EE0005993

Assignee:: The University of Toledo (Toledo, OH)

Patent Number(s):: 10,087,137

Application Number:: 15/320,802

OSTI ID:: 1492012

Resource Relation:: Patent File Date: 2015 Jun 22

Country of Publication:: United States

Language:: English

References (5)

Synthesis of Unsaturated Amino Alcohols through Unexpectedly Selective Ru-Catalyzed Cross-Metathesis Reactions Hoveyda, Hamid R.; Vézina, Martin Organic Letters, Vol. 7, Issue 11, p. 2113-2116 https://doi.org/10.1021/ol050387g	journal	May 2005
Hoveyda–Grubbs type metathesis catalyst immobilized on mesoporous molecular sieves MCM-41 and SBA-15 Balcar, Hynek; Shinde, Tushar; Žilková, Naděžda Beilstein Journal of Organic Chemistry, Vol. 7, p. 22-28 https://doi.org/10.3762/bjoc.7.4	journal	January 2011
The Reaction of Organoboranes with Chloramine and with Hydroxylamine-O-sulfonic Acid. A Convenient Synthesis of Amines from Olefins via Hydroboration Brown, Herbert C.; Heydkamp, Wolfgang R.; Breuer, Eli. Journal of the American Chemical Society, Vol. 86, Issue 17 https://doi.org/10.1021/ja01071a036	journal	September 1964
Prevention of Undesirable Isomerization during Olefin Metathesis Hong, Soon Hyeok; Sanders, Daniel P.; Lee, Choon Woo Journal of the American Chemical Society, Vol. 127, Issue 49 https://doi.org/10.1021/ja052939w	journal	December 2005
Tandem Catalytic Acrylonitrile Cross-Metathesis and Hydrogenation of Nitriles with Ruthenium Catalysts: Direct Access to Linear α,ω-Aminoesters from Renewables Miao, Xiaowei; Fischmeister, Cédric; Bruneau, Christian ChemSusChem, Vol. 5, Issue 8, p. 1410-1414 https://doi.org/10.1002/cssc.201200086	journal	June 2012

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