Abstract

Provided herein is a method of producing C11, C12, and C13 nylon precursors from oleic acid or esters of oleic acid, the method involving amide formation, ring-closing metathesis, and hydrogenation. Further provided are the products of the method described. Provided herein is a method for producing a lactam, the method comprising the steps of converting oleic acid or an ester of oleic acid into an amide having a general formula of H3C—(CH2)rCH═CH—(CH2)rCONR—(CH2)n-CH═CH2, wherein n is 1, 2, or 3, and R is either hydrogen or benzyl; subjecting the amide to a ring-closing metathesis reaction to produce an intermediate having a general formula of —(CH2)rCONR—(CH2) n-CH═CH2-, wherein n is 1, 2, or 3, R is either hydrogen or benzyl, and both ends are connected to each other; and hydrogenating the intermediate to produce a saturated lactam. In certain embodiments, the saturated lactam has a formula of —NH—(CH2) 10-CO—.

Document Type

Patent

Primary Class

C07D225/02

Application Number

15/323583

Filing Date

7-2-2015

Patent Number

US9845294

Assignee(s)

The University of Toledo

Publication Date

12-19-2017

Patent Country

United States

Language

en_US

Institution

The University of Toledo

Repository

University of Toledo Digital Libraries

Digital Publisher

Digital Initiatives

Rights

These materials are free of copyright restrictions and are in the public domain within the United States only. The USPTO reserves the right to assert copyright protection internationally.

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