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).

  • Patent number: 11186802
    Abstract: 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: Grant
    Filed: July 1, 2020
    Date of Patent: November 30, 2021
    Assignee: The United States of America, as represented by The Secretary of Agriculture
    Inventors: Kenneth M. Doll, Bryan R. Moser, Gerhard H. Knothe
  • Publication number: 20210032565
    Abstract: 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: Application
    Filed: July 1, 2020
    Publication date: February 4, 2021
    Inventors: Kenneth M. Doll, Bryan R. Moser, Gerhard H. Knothe
  • Patent number: 10457615
    Abstract: 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: Grant
    Filed: December 7, 2017
    Date of Patent: October 29, 2019
    Assignee: The United States of America, as represented by the Secretary of Agriculture
    Inventors: Rex E. Murray, Kenneth M. Doll, Zengshe Liu
  • Publication number: 20180222812
    Abstract: 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: Application
    Filed: December 7, 2017
    Publication date: August 9, 2018
    Inventors: Rex E. Murray, Kenneth M. Doll, Zengshe Liu
  • Patent number: 9868679
    Abstract: 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: Grant
    Filed: March 11, 2014
    Date of Patent: January 16, 2018
    Assignee: THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF AGRICULTURE
    Inventors: Rex E. Murray, Kenneth M. Doll, Zengshe Liu
  • Patent number: 9850222
    Abstract: 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: Grant
    Filed: August 1, 2016
    Date of Patent: December 26, 2017
    Assignee: The United States of America, as represented by the Secretary of Agriculture
    Inventors: Kenneth M. Doll, Terry Isbell, Steven C. Cermak, James A. Kenar
  • Publication number: 20170044128
    Abstract: 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: Application
    Filed: August 1, 2016
    Publication date: February 16, 2017
    Inventors: Kenneth M. Doll, Terry Isbell, Steven C. Cermak, James A. Kenar
  • Patent number: 9540264
    Abstract: 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: Grant
    Filed: August 3, 2015
    Date of Patent: January 10, 2017
    Assignee: The United States of America, as Represented by the Secretary of Agriculture
    Inventors: Rex E. Murray, Grigor B. Bantchev, Kenneth M. Doll, Robert O. Dunn, Kim L. Ascherl
  • Publication number: 20150336883
    Abstract: 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: Application
    Filed: August 3, 2015
    Publication date: November 26, 2015
    Inventors: Rex E. Murray, Grigor B. Bantchev, Kenneth M. Doll, Robert O. Dunn, Kim L. Ascherl
  • Patent number: 9126909
    Abstract: 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: Grant
    Filed: December 6, 2012
    Date of Patent: September 8, 2015
    Assignee: The United States of America, as represented by The Secretary of Agriculture
    Inventors: Rex E. Murray, Grigor B. Bantchev, Kenneth M. Doll, Robert O. Dunn, Kim L. Ascherl
  • Patent number: 8841470
    Abstract: 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: Grant
    Filed: August 24, 2011
    Date of Patent: September 23, 2014
    Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research Foundation
    Inventors: Atanu Biswas, Kenneth M. Doll, Huai Nan Cheng, Brajendra K. Sharma
  • Publication number: 20140275592
    Abstract: 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: Application
    Filed: March 11, 2014
    Publication date: September 18, 2014
    Applicant: The United States of America, as represented by the Secretary of Agriculture
    Inventors: Rex E. Murray, Kenneth M. Doll, Zengshe Liu
  • Patent number: 8822712
    Abstract: 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: Grant
    Filed: August 30, 2011
    Date of Patent: September 2, 2014
    Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research Foundation
    Inventors: Kenneth M. Doll, Brajendra K. Sharma, Paulo A. Suarez
  • Patent number: 8173825
    Abstract: 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: Grant
    Filed: March 13, 2007
    Date of Patent: May 8, 2012
    Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research Foundation
    Inventors: Sevim Z. Erhan, Kenneth M. Doll, Brajendra K. Sharma
  • Publication number: 20080154053
    Abstract: 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: Application
    Filed: March 13, 2007
    Publication date: June 26, 2008
    Applicants: The Unites States of America, as represented by the Secretary of Agriculture, The Penn State Research Foundation
    Inventors: Sevim Z. Erhan, Kenneth M. Doll, Brajendra K. Sharma