The University of Toledo

Godwin Abel

Sasidhar Varanasi

Sridhar Viamajala

Kana Yamamoto

Ajith Yapa Mudiyanselage

Kim Nguyen

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&#x2014;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.

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

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&#x2014;(CH2)rCH&#x2550;CH&#x2014;(CH2)rCONR&#x2014;(CH2)n-CH&#x2550;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 &#x2014;(CH2)rCONR&#x2014;(CH2) n-CH&#x2550;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 &#x2014;NH&#x2014;(CH2) 10-CO&#x2014;.

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Toledo, OH, United States of America

Godwin Abel