Ring closing metathesis approach to produce precursors of nylon 11, 12, and 13 from oleic acid
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United States of America Patent
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Dec 19, 2017
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app pub date -
Jul 2, 2015
filing date -
Jul 3, 2014
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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—.
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