Patents by Inventor John W. Frost

John W. Frost 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: 9499465
    Abstract: Methods for producing bio-terephthalic acid and bio-isophthalic acid are provided. The methods comprise a cycloaddition reaction to produce bio-4-methyl-3-cyclohexene-1-carboxylic acid, and bio-3-methyl-3-cyclohexene-1-carboxylic from bio-isoprene and bio-acrylic acid. An aromatization reaction produces bio-para-toluic acid and bio-meta-toluic acid from the bio-4-methyl-3-cyclohexene-1-carboxylic acid, and bio-3-methyl-3-cyclohexene-1-carboxylic. An oxidation reaction produces the bio-terephthalic acid and iso-phthalic acid from the bio-para-toluic acid and bio-meta-toluic acid.
    Type: Grant
    Filed: March 14, 2014
    Date of Patent: November 22, 2016
    Assignee: Board of Trustees of Michigan State University
    Inventor: John W. Frost
  • Publication number: 20160176799
    Abstract: A method for isolating and purifying shikimic acid from a fermentation broth is provided. The method includes performing a liquid-liquid extraction on the fermentation broth with an alcohol solution to generate an extract, crystallizing solids from the extract, dissolving the solids in a second alcohol solution to generate a solution having shikimic acid, and filtering the solution having shikimic acid through a filter that does not contain ion exchange resins. Methods for dehydrating the shikimic acid to yield p-hydroxybenzoic acid are also provided.
    Type: Application
    Filed: December 18, 2015
    Publication date: June 23, 2016
    Inventors: Karen M. FROST, John W. FROST
  • Publication number: 20160031787
    Abstract: Methods for producing bio-terephthalic acid and bio-isophthalic acid. Methods comprise a cycloaddition reaction to produce bio-4-methyl-3-cyclohexene-1-carboxylic acid, and bio-3-methyl-3-cyclohexene-1-carboxylic from bio-isoprene and bio-acrylic acid. An aromatization reaction produces bio-para-toluic acid and bio-meta-toluic acid from the bio-4-methyl-3-cyclohexene-1-carboxylic acid, and bio-3-methyl-3-cyclohexene-1-carboxylic. An oxidation reaction produces the bio-terephthalic acid and isophthalic acid from the bio-para-toluic acid and bio-meta-toluic acid.
    Type: Application
    Filed: March 14, 2014
    Publication date: February 4, 2016
    Applicant: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY
    Inventor: John W. FROST
  • Patent number: 9073867
    Abstract: Provided herein are processes for preparing caprolactam from a starting material such as one or more of the cis,cis-, cis,trans- and trans,trans-double-bond isomers of muconamide, muconic acid ester, or muconic acid. The starting material, intermediates, and caprolactam prepared therefrom can contain carbon atoms derived from biomass containing detectable 14C content determined according to ASTM D6866 and optionally containing a 14C content up to 0.0000000001% (one part per trillion). Caprolactam so prepared can be used to make various polyamides.
    Type: Grant
    Filed: April 9, 2012
    Date of Patent: July 7, 2015
    Assignee: Amyris, Inc.
    Inventors: Laetitia Coudray, Vu Bui, John W. Frost, Dirk Schweitzer
  • Patent number: 8492581
    Abstract: The present invention provides improved process for the sulfonation of hydroxyaromatics amenable to direct isolation of the sulfonylated hydroxyaromatics in their free-acid forms. The process allows for the recyclization of sulfuric acid and minimizes waste. The starting materials are from a renewal resource, e.g., biomass, and contain detectable 14C up to a 14C content of 0.0000000001% (one part per trillion). The products made include sulfonated catechol, disulfonated pyrogallol and sulfonated protocatechuic acid.
    Type: Grant
    Filed: August 20, 2010
    Date of Patent: July 23, 2013
    Assignee: Amyris, Inc.
    Inventors: John W Frost, Vu Bui
  • Patent number: 8426639
    Abstract: The present invention relates to the isomerization of cis,cis and/or cis,trans muconic acid or esters thereof to trans,trans muconic acid or esters thereof and to the esterification of such muconic acids.
    Type: Grant
    Filed: June 16, 2010
    Date of Patent: April 23, 2013
    Assignee: Amyris, Inc.
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui
  • Patent number: 8415496
    Abstract: The present invention relates to polyesters prepared from benzene, cyclohexene and cyclohexane compounds having carboxylic acid groups at the 1 and 4, and optionally the 2, positions, such as terephthalic acid or dimethyl terephthalates, and alkylene glycols, such ethylene glycol or 1,4-butane diol. The invention also relates to processes for preparing such polyesters. The invention also relates to such polyesters derived from starting materials derived from renewable resources.
    Type: Grant
    Filed: June 16, 2010
    Date of Patent: April 9, 2013
    Assignee: Amyris, Inc.
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui, Edward Paschke, Douglas A. Wicks
  • Publication number: 20130085255
    Abstract: Provided herein are processes for preparing caprolactam from a starting material such as one or more of the cis,cis-, cis,trans- and trans,trans-double-bond isomers of muconamide, muconic acid ester, or muconic acid. The starting material, intermediates, and caprolactam prepared therefrom can contain carbon atoms derived from biomass containing detectable 14C content determined according to ASTM D6866 and optionally containing a 14C content up to 0.0000000001% (one part per trillion). Caprolactam so prepared can be used to make various polyamides.
    Type: Application
    Filed: April 9, 2012
    Publication date: April 4, 2013
    Applicant: Amyris, Inc.
    Inventors: Laetitia Coudray, Vu Bui, John W. Frost, Dirk Schweitzer
  • Patent number: 8372621
    Abstract: Novel enzymes and novel enzymatic pathways for the pyruvate-based synthesis of shikimate or at least one intermediate thereto or derivative thereof, nucleic acids encoding the enzymes, cells transformed therewith, and kits containing said enzymes, cells, or nucleic acid. A KDPGal aldolase is used to perform condensation of pyruvate with D-erythrose 4-phosphate to form 3-deoxy-D-arabino-heptulosonate-7-phosphate (DAHP); a 3-dehydroquinate synthase is used to convert the DAHP to 3-dehydroquinate (DHQ); DHQ dehydratase can then convert DHQ to the key shikimate intermediate, 3-dehydroshikimate.
    Type: Grant
    Filed: July 20, 2010
    Date of Patent: February 12, 2013
    Assignee: Board of Trustees Operating Michigan State University
    Inventor: John W. Frost
  • Patent number: 8367859
    Abstract: The present invention relates to cyclohexanes having carboxylate derivatives at the 1 and 4, and optionally the 2, position. The invention also relates to processes for preparing such compounds wherein a portion of the starting materials utililzed is derived from renewable resources.
    Type: Grant
    Filed: June 16, 2010
    Date of Patent: February 5, 2013
    Assignee: Amyris, Inc.
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui, Douglas A. Wicks
  • Patent number: 8367819
    Abstract: In various embodiments, the present invention can involve a method of synthesizing ?-amino-?-caprolactam. The method can comprise heating a salt of L-lysine in a solvent comprising an alcohol. In other embodiments, the present invention can involve methods for synthesizing ?-caprolactam. The methods can comprise heating a salt of L-lysine in a solvent comprising an alcohol and deaminating the reaction product. In various embodiments, the invention can include methods of converting biomass into nylon 6. The methods can comprise heating L-lysine in a solvent comprising an alcohol to produce ?-amino-?caprolactam, deaminating to produce ?-caprolactam and polymerizing into nylon 6, wherein the L-lysine is derived from the biomass. In other embodiments, the present invention can include methods of making nylon 6. The methods can comprise synthesizing ?-caprolactam and then polymerizing, wherein the ?-caprolactam is derived from L-lysine.
    Type: Grant
    Filed: July 1, 2011
    Date of Patent: February 5, 2013
    Assignee: Board of Trustees of Michigan State University
    Inventor: John W. Frost
  • Patent number: 8367858
    Abstract: The present invention relates to novel substituted and unsubstituted terephthalic acid and carboxylate derivatives and products prepared therefrom having a significant renewable content. The invention also relates to processes for preparing substituted and unsubstituted terephthalic and carboxylate derivatives thereof wherein a portion of the starting materials utilized is derived from renewable resources. The invention also relates to novel cyclohexene based intermediates prepared in these processes and to conversion of these intermediates to substituted and unsubstituted cyclohexane-1,4-dicarboxylates and carboxylate derivatives thereof and novel forms of the resulting products having renewable content. The invention also relates to products prepared from substituted and unsubstituted terephthalic acid and carboxylate derivatives thereof derived from starting materials derived from renewable resources.
    Type: Grant
    Filed: June 16, 2010
    Date of Patent: February 5, 2013
    Assignee: Amyris, Inc.
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui, Douglas A. Wicks
  • Patent number: 8329445
    Abstract: The present invention provides methods, enzymes, and cells for the biosynthetic production of phloroglucinol from malonyl-CoA, which is ultimately obtained from simple starting materials such as glucose; also provided are methods for preparing derivatives of biosynthetic phloroglucinol, including, e.g., resorcinol.
    Type: Grant
    Filed: April 7, 2011
    Date of Patent: December 11, 2012
    Assignee: Board of Trustees of Michigan State University
    Inventor: John W. Frost
  • Patent number: 8283466
    Abstract: Catalytic processes for preparing caprolactam, pipecolinic acid, and their derivatives, from lysine or alpha-amino-epsilon-caprolactam starting materials, and products produced thereby. A process for preparing caprolactam or a derivative thereof, the process comprising contacting a reactant comprising lysine or alpha aminocaprolactam with a catalyst and a gas comprising hydrogen gas, in the presence of a solvent. The catalyst may be provided on a support material, such as a transition metal.
    Type: Grant
    Filed: February 20, 2008
    Date of Patent: October 9, 2012
    Assignee: Board of Trustees of Michigan State University
    Inventor: John W. Frost
  • Publication number: 20120142886
    Abstract: In various embodiments, the present invention can involve a method of synthesizing ?-amino-?-caprolactam. The method can comprise heating a salt of L-lysine in a solvent comprising an alcohol. In other embodiments, the present invention can involve methods for synthesizing ?-caprolactam. The methods can comprise heating a salt of L-lysine in a solvent comprising an alcohol and deaminating the reaction product. In various embodiments, the invention can include methods of converting biomass into nylon 6. The methods can comprise heating L-lysine in a solvent comprising an alcohol to produce ?-amino-?caprolactam, deaminating to produce ?-caprolactam and polymerizing into nylon 6, wherein the L-lysine is derived from the biomass. In other embodiments, the present invention can include methods of making nylon 6. The methods can comprise synthesizing ?-caprolactam and then polymerizing, wherein the ?-caprolactam is derived from L-lysine.
    Type: Application
    Filed: July 1, 2011
    Publication date: June 7, 2012
    Applicant: Board of Trustees of Michigan State University
    Inventor: John W. Frost
  • Patent number: 8080397
    Abstract: A bioengineered synthesis scheme for the production of quinic acid from a carbon source is provided. Methods of producing quinic acid from a carbon source based on the synthesis scheme as well as conversion of quinic acid to hydroquinone are also provided.
    Type: Grant
    Filed: November 20, 2009
    Date of Patent: December 20, 2011
    Assignee: Board of Trustees Operating Michigan State University
    Inventors: John W. Frost, Karen M. Frost
  • Publication number: 20110288310
    Abstract: The present invention relates to cyclohexanes having carboxylate derivatives at the 1 and 4, and optionally the 2, position. The invention also relates to processes for preparing such compounds wherein a portion of the starting materials utililzed is derived from renewable resources.
    Type: Application
    Filed: June 16, 2010
    Publication date: November 24, 2011
    Applicant: Draths Corporation
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui, Douglas A. Wicks
  • Publication number: 20110288263
    Abstract: The present invention relates to polyesters prepared from benzene, cyclohexene and cyclohexane compounds having carboxylic acid groups at the 1 and 4, and optionally the 2, positions, such as terephthalic acid or dimethyl terephthalates, and alkylene glycols, such ethylene glycol or 1,4-butane diol. The invention also relates to processes for preparing such polyesters. The invention also relates to such polyesters derived from starting materials derived from renewable resources.
    Type: Application
    Filed: June 16, 2010
    Publication date: November 24, 2011
    Applicant: Draths Corporation
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui, Edward Paschke, Douglas A. Wicks
  • Publication number: 20110288311
    Abstract: The present invention relates to novel substituted and unsubstituted terephthalic acid and carboxylate derivatives and products prepared therefrom having a significant renewable content. The invention also relates to processes for preparing substituted and unsubstituted terephthalic and carboxylate derivatives thereof wherein a portion of the starting materials utilized is derived from renewable resources. The invention also relates to novel cyclohexene based intermediates prepared in these processes and to conversion of these intermediates to substituted and unsubstituted cyclohexane-1,4-dicarboxylates and carboxylate derivatives thereof and novel forms of the resulting products having renewable content. The invention also relates to products prepared from substituted and unsubstituted terephthalic acid and carboxylate derivatives thereof derived from starting materials derived from renewable resources.
    Type: Application
    Filed: June 16, 2010
    Publication date: November 24, 2011
    Applicant: Draths Corporation
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui, Douglas A. Wicks
  • Publication number: 20110282078
    Abstract: The present invention relates to cyclohexenes having carboxylate derivatives at the 1 and 4, and optionally the 2, position. The invention also relates to processes for preparing such compounds wherein a portion of the starting materials utilized is derived from renewable resources.
    Type: Application
    Filed: June 16, 2010
    Publication date: November 17, 2011
    Applicant: Draths Corporation
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui, Douglas A. Wicks