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Published September 22, 2020 | Accepted Version + Supplemental Material
Journal Article Open

Efficient Synthesis of Geminal-Dialkyl Dienes for Olefin Metathesis Polymerization


A robust synthesis of gem-dialkyl acyclic diene monomers has been developed. This route is scalable, flexible, and biorenewable, allowing for the production of a wide range of diene monomers of different lengths and different gem-dialkyl substitutions starting from unsaturated esters derived from seed oils. The metathesis polymerization of these monomers and the hydrogenation of the resulting polyolefins lead to telechelic gem-dialkyl polyethylenes, which can be used as elastomers in the synthesis of polyurethanes and other block polymers.

Additional Information

© 2020 American Chemical Society. Received: July 13, 2020; Revised: August 25, 2020; Published: September 10, 2020. W.J.W. gratefully acknowledges the support of the Arnold O. Beckman postdoctoral fellowship. B.M.S. thanks the NIH-GMS (R01GM080269) for generous support. We thank Mr. Doug Rose and Prof. Heather Maynard (UCLA) for use of their DSC instrument, and Prof. Marc Hillmyer (UMN) for sharing the details of the synthesis of 38. We are grateful to Steve Cohen and Elevance Renewable Sciences for their donation of methyl 9-decenoate. Author Contributions. W.J.W. and J. L. contributed equally. The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript. The authors declare the following competing financial interest(s): A provisional patent regarding this work (CIT-8317-P) has been filed.

Attached Files

Accepted Version - nihms-1626180.pdf

Supplemental Material - ma0c01606_si_001.pdf


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