utpatents-US9845294

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Abstract/Description: 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-.
Subject(s): C07D225/02
Date Issued: 2017-12-19
Title: Ring closing metathesis approach to produce precursors of nylon 11, 12, and 13 from oleic acid.
Name(s): The University of Toledo, assignee
Yamamoto, Kana, inventor
Viamajala, Sridhar, inventor
Varanasi, Sasidhar, inventor
Mudiyanselage, Ajith Yapa, inventor
Abel, Godwin Ameh, inventor
Type of Resource: text
Genre: patent
Publisher: United States Patent and Trademark Office
Other Date: Date Filed: 2015-07-02
Date Issued: 2017-12-19
Physical Form: application/pdf
Extent: 25 p.
Abstract/Description: 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-.
Identifier(s): utpatents-US9845294 (IID)
Patent No.: US9845294 (patno)
Appl. No.: 15/323583 (appno)
Subject(s): C07D225/02
Held by: United States Patent and Trademark Office (USPTO) Public Search Facility
Location: University of Toledo Digital Repository
Rights Statement: No Copyright - United States
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