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-. |
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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. |
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Name(s): |
The University of Toledo, assignee Yamamoto, Kana, inventor Viamajala, Sridhar, inventor Varanasi, Sasidhar, inventor Mudiyanselage, Ajith Yapa, inventor Abel, Godwin Ameh, inventor |
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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) |
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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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