Patents by Inventor Kenneth M. Doll
Kenneth M. Doll 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: 11186802Abstract: Disclosed herein are processes for the decarboxylation, isomerization, hydrogenation, dehydrogenation, and cyclization/aromatization of fatty acids involving contacting a starting material which is an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride, in the presence of a catalyst at a temperature at which decarboxylation, isomerization, hydrogenation, dehydrogenation, and cyclization/aromatization occurs and recovering the unsaturated organic compound product; wherein the catalyst is chloro-1,5-cyclooctadiene iridium (I) dimer. The product may contain at least about 8% by volume aromatic content and less than about 25% by volume aromatic content, and wherein the product contains less than about 1% by volume of naphthalenes.Type: GrantFiled: July 1, 2020Date of Patent: November 30, 2021Assignee: The United States of America, as represented by The Secretary of AgricultureInventors: Kenneth M. Doll, Bryan R. Moser, Gerhard H. Knothe
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Publication number: 20210032565Abstract: Disclosed herein are processes for the decarboxylation, isomerization, hydrogenation, dehydrogenation, and cyclization/aromatization of fatty acids involving contacting a starting material which is an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride, in the presence of a catalyst at a temperature at which decarboxylation, isomerization, hydrogenation, dehydrogenation, and cyclization/aromatization occurs and recovering the unsaturated organic compound product; wherein the catalyst is chloro-1,5-cyclooctadiene iridium (I) dimer. The product may contain at least about 8% by volume aromatic content and less than about 25% by volume aromatic content, and wherein the product contains less than about 1% by volume of naphthalenes.Type: ApplicationFiled: July 1, 2020Publication date: February 4, 2021Inventors: Kenneth M. Doll, Bryan R. Moser, Gerhard H. Knothe
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Patent number: 10457615Abstract: Disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the isomerization of an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride. Also disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the decarboxylation of an unsaturated organic compound. Also disclosed is the use of a catalyst or catalyst precursor for the dual function isomerization and decarboxylation of an unsaturated fatty acid to an unsaturated organic compound.Type: GrantFiled: December 7, 2017Date of Patent: October 29, 2019Assignee: The United States of America, as represented by the Secretary of AgricultureInventors: Rex E. Murray, Kenneth M. Doll, Zengshe Liu
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Publication number: 20180222812Abstract: Disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the isomerization of an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride. Also disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the decarboxylation of an unsaturated organic compound. Also disclosed is the use of a catalyst or catalyst precursor for the dual function isomerization and decarboxylation of an unsaturated fatty acid to an unsaturated organic compound.Type: ApplicationFiled: December 7, 2017Publication date: August 9, 2018Inventors: Rex E. Murray, Kenneth M. Doll, Zengshe Liu
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Patent number: 9868679Abstract: Disclosed is a method for using a metal catalyst or catalyst precursor that catalyzes the isomerization of an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride. Also disclosed is a method for using a metal catalyst or catalyst precursor that catalyzes the decarboxylation of an unsaturated organic compound. Also disclosed is a method for using a catalyst or catalyst precursor for the dual function isomerization and decarboxylation of an unsaturated fatty acid to an unsaturated organic compound.Type: GrantFiled: March 11, 2014Date of Patent: January 16, 2018Assignee: THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF AGRICULTUREInventors: Rex E. Murray, Kenneth M. Doll, Zengshe Liu
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Patent number: 9850222Abstract: Disclosed herein are the conversion of estolide compounds having unsaturated fatty acid groups into estolides containing cyclic carbonate moieties and methods of making and using the same. The estolides containing a cyclic carbonate may be used to produce urethane containing estolides.Type: GrantFiled: August 1, 2016Date of Patent: December 26, 2017Assignee: The United States of America, as represented by the Secretary of AgricultureInventors: Kenneth M. Doll, Terry Isbell, Steven C. Cermak, James A. Kenar
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Publication number: 20170044128Abstract: Disclosed herein are the conversion of estolide compounds having unsaturated fatty acid groups into estolides containing cyclic carbonate moieties and methods of making and using the same. The estolides containing a cyclic carbonate may be used to produce urethane containing estolides.Type: ApplicationFiled: August 1, 2016Publication date: February 16, 2017Inventors: Kenneth M. Doll, Terry Isbell, Steven C. Cermak, James A. Kenar
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Patent number: 9540264Abstract: We have now discovered a novel process for the removal or extraction of metal species from a variety of solid, liquid or gas phase materials. Metal species may be removed by contacting the material suspected of containing one or more metals with a thiolated fatty acid or ester thereof for a period of time and under conditions effective far the sequestration of the metal species by the thiolated fatty acid or ester thereof. The thiolated fatty acid or ester thereof comprising sequestered metal species may then be separated and recovered from the treated material. Moreover, following the treatment of aqueous liquids or mixtures, or suspensions or dispersions of solids in aqueous liquids, the resultant thiolated fatty acid or ester thereof comprising the sequestered metal species is insoluble in water and forms a separate layer from the aqueous liquid phase, which layer may be readily removed.Type: GrantFiled: August 3, 2015Date of Patent: January 10, 2017Assignee: The United States of America, as Represented by the Secretary of AgricultureInventors: Rex E. Murray, Grigor B. Bantchev, Kenneth M. Doll, Robert O. Dunn, Kim L. Ascherl
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Publication number: 20150336883Abstract: We have now discovered a novel process for the removal or extraction of metal species from a variety of solid, liquid or gas phase materials. Metal species may be removed by contacting the material suspected of containing one or more metals with a thiolated fatty acid or ester thereof for a period of time and under conditions effective far the sequestration of the metal species by the thiolated fatty acid or ester thereof. The thiolated fatty acid or ester thereof comprising sequestered metal species may then be separated and recovered from the treated material. Moreover, following the treatment of aqueous liquids or mixtures, or suspensions or dispersions of solids in aqueous liquids, the resultant thiolated fatty acid or ester thereof comprising the sequestered metal species is insoluble in water and forms a separate layer from the aqueous liquid phase, which layer may be readily removed.Type: ApplicationFiled: August 3, 2015Publication date: November 26, 2015Inventors: Rex E. Murray, Grigor B. Bantchev, Kenneth M. Doll, Robert O. Dunn, Kim L. Ascherl
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Patent number: 9126909Abstract: We have now discovered a novel process for the removal or extraction of metal species from a variety of solid, liquid or gas phase materials. Metal species may be removed by contacting the material suspected of containing one or more metals with a thiolated fatty acid or ester thereof for a period of time and under conditions effective for the sequestration of the metal species by the thiolated fatty acid or ester thereof. The thiolated fatty acid or ester thereof comprising sequestered metal species may then be separated and recovered from the treated material. Moreover, following the treatment of aqueous liquids or mixtures, or suspensions or dispersions of solids in aqueous liquids, the resultant thiolated fatty acid or ester thereof comprising the sequestered metal species is insoluble in water and forms a separate layer from the aqueous liquid phase, which layer may be readily removed.Type: GrantFiled: December 6, 2012Date of Patent: September 8, 2015Assignee: The United States of America, as represented by The Secretary of AgricultureInventors: Rex E. Murray, Grigor B. Bantchev, Kenneth M. Doll, Robert O. Dunn, Kim L. Ascherl
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Patent number: 8841470Abstract: Chemically-modified fatty acids are prepared by reacting epoxidized fatty acids, their esters or triglyceride oils with amines of cyclic or aromatic hydrocarbons. The fatty acid derivatives produced are of the formula: wherein R is an H, branched or straight chain alkyl or alkenyl group, aromatic-containing group, glycerol, or glyceride, R? is a C3 to C29 aliphatic chain comprising one or more of the derivatized methylene groups of the formula: wherein R1 and R2 are independently selected from the group consisting of H, cyclic hydrocarbons, substituted cyclic hydrocarbons, and aryl groups, with the proviso that only one of said R1 and R2 may be H. These fatty acid derivatives have utility as antiwear/antifriction additives for industrial oils and automotive applications.Type: GrantFiled: August 24, 2011Date of Patent: September 23, 2014Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research FoundationInventors: Atanu Biswas, Kenneth M. Doll, Huai Nan Cheng, Brajendra K. Sharma
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Publication number: 20140275592Abstract: Disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the isomerization of an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride. Also disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the decarboxylation of an unsaturated organic compound. Also disclosed is the use of a catalyst or catalyst precursor for the dual function isomerization and decarboxylation of an unsaturated fatty acid to an unsaturated organic compound.Type: ApplicationFiled: March 11, 2014Publication date: September 18, 2014Applicant: The United States of America, as represented by the Secretary of AgricultureInventors: Rex E. Murray, Kenneth M. Doll, Zengshe Liu
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Patent number: 8822712Abstract: Chemically-modified triglycerides are prepared by reacting epoxidized triglyceride oils with phosphorus-based acid hydroxide or esters. The phosphorus-containing triglyceride derivatives are of the formula: wherein R1?, R2? and R3? are independently selected from C3 to C29 aliphatic fatty acid residues, at least one of which comprising one or both of the derivatized methylene groups of the formula: wherein m is 0, 1 or 2, n is 0 or 1, q is 1, 2 or 3, and R and R? are independently selected from the group consisting of H, straight, branched or cyclic hydrocarbons and substituted hydrocarbons, and aryl groups. The phosphorus-containing triglyceride derivatives so produced have utility as antiwear/antifriction additives for industrial oils and automotive applications.Type: GrantFiled: August 30, 2011Date of Patent: September 2, 2014Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research FoundationInventors: Kenneth M. Doll, Brajendra K. Sharma, Paulo A. Suarez
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Patent number: 8173825Abstract: Fatty acid ester derivatives and a process for their production from unsaturated fatty acids are disclosed. The process comprises: a) reacting an unsaturated fatty acid or an ester thereof having one or more sites of unsaturation, with an epoxidation reagent to form a fatty acid epoxide wherein at least one of the sites of unsaturation of the fatty acid or fatty acid ester is converted to an oxirane ring; and b) reacting the fatty acid epoxide produced in a) with a carboxylic acid to form a hydroxy fatty acid ester derivative wherein the oxirane ring is opened and converted to a hydroxy ester comprising a hydroxyl group at one carbon of the opened oxirane ring and an ester of the carboxylic acid at the other carbon of the opened oxirane ring.Type: GrantFiled: March 13, 2007Date of Patent: May 8, 2012Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research FoundationInventors: Sevim Z. Erhan, Kenneth M. Doll, Brajendra K. Sharma
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Publication number: 20080154053Abstract: Fatty acid ester derivatives and a process for their production from unsaturated fatty acids are disclosed. The process comprises: a) reacting an unsaturated fatty acid or an ester thereof having one or more sites of unsaturation, with an epoxidation reagent to form a fatty acid epoxide wherein at least one of the sites of unsaturation of the fatty acid or fatty acid ester is converted to an oxirane ring; and b) reacting the fatty acid epoxide produced in a) with a carboxylic acid to form a hydroxy fatty acid ester derivative wherein the oxirane ring is opened and converted to a hydroxy ester comprising a hydroxyl group at one carbon of the opened oxirane ring and an ester of the carboxylic acid at the other carbon of the opened oxirane ring.Type: ApplicationFiled: March 13, 2007Publication date: June 26, 2008Applicants: The Unites States of America, as represented by the Secretary of Agriculture, The Penn State Research FoundationInventors: Sevim Z. Erhan, Kenneth M. Doll, Brajendra K. Sharma