Patents by Inventor Keith M. Wampler
Keith M. Wampler has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 11779911Abstract: In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.Type: GrantFiled: July 30, 2021Date of Patent: October 10, 2023Assignee: PROVIVI, INC.Inventors: Keith M. Wampler, Peter Meinhold, Pedro Coelho, Vu Bui, Hasan Mehdi
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Publication number: 20230095259Abstract: Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.Type: ApplicationFiled: November 16, 2022Publication date: March 30, 2023Applicant: Provivi, Inc.Inventors: Keith M. Wampler, Richard L. Pederson
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Publication number: 20220136018Abstract: The present application relates to methods of producing one or more fatty alcohols and/or one or more fatty aldehydes from one or more unsaturated lipid moieties by combining the obtainment or production of the one or more unsaturated lipid moieties from a biological source with conversion by non-biological means of the one or more unsaturated lipid moieties to one or more fatty alcohols and/or one or more fatty aldehydes. The present application also relates to recombinant microorganisms having a biosynthesis pathway for the production of one or more unsaturated lipid moieties. The one or more fatty alcohols can further be chemically converted to one or more corresponding fatty acetates. The one or more fatty alcohols, one or more fatty aldehydes and/or one or more fatty acetates produced by the methods described herein may be one or more insect pheromones, one or more fragrances, one or more flavoring agents, or one or more polymer intermediates.Type: ApplicationFiled: November 15, 2021Publication date: May 5, 2022Inventors: Konrad B. OTTE, Micah SHEPPARD, Vu BUI, Keith M. WAMPLER, Effendi LEONARD
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Publication number: 20220032280Abstract: In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.Type: ApplicationFiled: July 30, 2021Publication date: February 3, 2022Applicants: Provivi, Inc., XiMo AGInventors: Keith M. Wampler, Peter Meinhold, Pedro Coelho, Vu Bui, Hasan Mehdi
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Publication number: 20220017449Abstract: Methods for preparing conjugated dienes are described. An ?,?-unsaturated E olefin intermediate may be prepared via cross-metathesis using a catalyst comprising a transition metal (e.g., ruthenium), a first carbene ligand (e.g., a substituted indenylidene) and an N-heterocyclic carbene ligand (e.g., an imidazolidinylidene). The catalyst further includes a phenylphosphine ligand, a tri(isopropoxy)phosphine ligand, a dimethylsulfoxide ligand, an acetonitrile ligand, or a pyridine ligand. Following the cross metathesis-step, the ?,?-unsaturated aldehyde intermediate may be converted to the conjugated diene product via reaction with a phosphonium ylide. Products obtained via the methods of the disclosure include (7E,9Z)-dodeca-7,9-dien-1-yl acetate, a pheromone produced by Lobesia botrana (European grapevine moth), and other insect pheromones.Type: ApplicationFiled: December 10, 2019Publication date: January 20, 2022Inventors: Keith M. Wampler, Choon Woo Lee, David Rozzell
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Patent number: 11214818Abstract: The present application relates to methods of producing one or more fatty alcohols and/or one or more fatty aldehydes from one or more unsaturated lipid moieties by combining the obtainment or production of the one or more unsaturated lipid moieties from a biological source with conversion by non-biological means of the one or more unsaturated lipid moieties to one or more fatty alcohols and/or one or more fatty aldehydes. The present application also relates to recombinant microorganisms having a biosynthesis pathway for the production of one or more unsaturated lipid moieties. The one or more fatty alcohols can further be chemically converted to one or more corresponding fatty acetates. The one or more fatty alcohols, one or more fatty aldehydes and/or one or more fatty acetates produced by the methods described herein may be one or more insect pheromones, one or more fragrances, one or more flavoring agents, or one or more polymer intermediates.Type: GrantFiled: June 6, 2017Date of Patent: January 4, 2022Assignee: Provivi, Inc.Inventors: Konrad B. Otte, Micah Sheppard, Vu Bui, Keith M. Wampler, Effendi Leonard
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Patent number: 11155505Abstract: Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.Type: GrantFiled: August 16, 2019Date of Patent: October 26, 2021Assignee: PROVIVI, INC.Inventors: Keith M. Wampler, Vu Bui, David Rozzell, Pedro Coelho, Arthur Floruti, Levente Ondi, Hasan Mehdi, Gabor Eros
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Patent number: 11077433Abstract: In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.Type: GrantFiled: February 24, 2020Date of Patent: August 3, 2021Assignee: PROVIVI, INC.Inventors: Keith M. Wampler, Peter Meinhold, Pedro Coelho, Vu Bui, Levente Ondi, Hasan Mehdi
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Publication number: 20210130270Abstract: Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.Type: ApplicationFiled: January 14, 2021Publication date: May 6, 2021Applicant: Provivi, Inc.Inventors: Keith M. WAMPLER, Choon Woo LEE, David ROZZELL
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Publication number: 20200261898Abstract: In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.Type: ApplicationFiled: February 24, 2020Publication date: August 20, 2020Applicant: Provivi, Inc.Inventors: Keith M. Wampler, Peter Meinhold, Pedro Coelho, Vu Bui, Levente Ondi, Hasan Mehdi
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Patent number: 10596562Abstract: In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.Type: GrantFiled: September 29, 2017Date of Patent: March 24, 2020Assignee: PROVIVI, INC.Inventors: Keith M. Wampler, Peter Meinhold, Pedro Coelho, Vu Bui, Levente Ondi, Hasan Mehdi
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Publication number: 20200039900Abstract: Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.Type: ApplicationFiled: August 16, 2019Publication date: February 6, 2020Applicant: Provivi, Inc.Inventors: Keith M. Wampler, Vu Bui, David Rozzell, Pedro Coelho, Arthur Floruti, Levente Ondi, Hasan Mehdi, Gabor Eros
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Patent number: 10479755Abstract: Methods of carrying out metathesis reactions of natural oil-derived polyenes (e.g., dienes and trienes), including functionalized polyenes, are generally disclosed herein. In some embodiments, the dienes or trienes contain a terminal carbon-carbon double bond, and the metathesis reaction is selective toward reaction of the terminal carbon-carbon double bonds in the polyene. Compounds made by such methods are also generally disclosed herein.Type: GrantFiled: December 12, 2016Date of Patent: November 19, 2019Assignee: Elevance Renewable Sciences, Inc.Inventors: Keith M. Wampler, Jane Uy, Steven A. Cohen
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Publication number: 20190136272Abstract: The present application relates to methods of producing one or more fatty alcohols and/or one or more fatty aldehydes from one or more unsaturated lipid moieties by combining the obtainment or production of the one or more unsaturated lipid moieties from a biological source with conversion by non-biological means of the one or more unsaturated lipid moieties to one or more fatty alcohols and/or one or more fatty aldehydes. The present application also relates to recombinant microorganisms having a biosynthesis pathway for the production of one or more unsaturated lipid moieties. The one or more fatty alcohols can further be chemically converted to one or more corresponding fatty acetates. The one or more fatty alcohols, one or more fatty aldehydes and/or one or more fatty acetates produced by the methods described herein may be one or more insect pheromones, one or more fragrances, one or more flavoring agents, or one or more polymer intermediates.Type: ApplicationFiled: June 6, 2017Publication date: May 9, 2019Inventors: Konrad B. OTTE, Micah SHEPPARD, Vu BUI, Keith M. WAMPLER, Effendi LEONARD
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Patent number: 9981898Abstract: The present invention relates, in part, to an improved process for oxidation of alcohols containing oxidatively sensitive functional groups, using inexpensive reagents under mild reaction conditions to provide high yields of carbonyl products such as aldehydes or ketones. In certain embodiments, an aldehyde product is obtained by contacting an oxidatively sensitive alcohol, such as an alkenol, with an oxidant and a TEMPO catalyst under conditions sufficient to convert the alkenol to the aldehyde.Type: GrantFiled: March 10, 2017Date of Patent: May 29, 2018Assignee: PROVIVI, INC.Inventors: Vu Bui, Peter Meinhold, Pedro Coelho, Keith M. Wampler, Michael Cockrem
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Publication number: 20180099268Abstract: In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.Type: ApplicationFiled: September 29, 2017Publication date: April 12, 2018Applicant: Provivi, Inc.Inventors: Keith M. Wampler, Peter Meinhold, Pedro Coelho, Vu Bui, Levente Ondi, Hasan Mehdi
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Patent number: 9776179Abstract: In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.Type: GrantFiled: November 17, 2016Date of Patent: October 3, 2017Assignee: PROVIVI, INC.Inventors: Keith M Wampler, Peter Meinhold, Pedro Coelho, Vu Bui, Levente Ondi, Hasan Mehdi
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Publication number: 20170183289Abstract: Methods of carrying out metathesis reactions of natural oil-derived polyenes (e.g., dienes and trienes), including functionalized polyenes, are generally disclosed herein. In some embodiments, the dienes or trienes contain a terminal carbon-carbon double bond, and the metathesis reaction is selective toward reaction of the terminal carbon-carbon double bonds in the polyene. Compounds made by such methods are also generally disclosed herein.Type: ApplicationFiled: December 12, 2016Publication date: June 29, 2017Applicant: Elevance Renewable Sciences, Inc.Inventors: Keith M. Wampler, Jane Uy, Steven A. Cohen
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Publication number: 20170137365Abstract: In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.Type: ApplicationFiled: November 17, 2016Publication date: May 18, 2017Applicant: PROVIVI, INC.Inventors: KEITH M. WAMPLER, PETER MEINHOLD, PEDRO COELHO, VU BUI, LEVENTE ONDI, HASAN MEHDI
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Publication number: 20170066993Abstract: A method for treating a substrate prior to a metathesis reaction includes treating the substrate with a first agent configured to mitigate potentially adverse effects of one or more contaminants in the substrate on a catalyst used to catalyze the metathesis reaction. The treating reduces a level of the one or more contaminants by an amount sufficient to enable the metathesis reaction to proceed at a substrate-to-catalyst molar ratio of at least about 7,500 to 1. Methods for metathesizing substrates are described.Type: ApplicationFiled: June 16, 2016Publication date: March 9, 2017Applicant: Elevance Renewable Sciences, Inc.Inventors: Keith M. Wampler, Steven A. Cohen, Georg E. Frater, Levente Ondi, Jeno Varga