Patents by Inventor Dimitri A. Hirsch-Weil
Dimitri A. Hirsch-Weil 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: 12281089Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of C6 saccharides, including isomers thereof, polymers thereof, and certain derivatives thereof. The methods make use of acids with lower concentrations, and allows for conversion of sugars into 5-(halomethyl)furfural at higher temperatures and faster reaction or residence times.Type: GrantFiled: March 4, 2022Date of Patent: April 22, 2025Assignee: Origin Materials Operating, Inc.Inventors: Alex B. Wood, Makoto N. Masuno, Ryan L. Smith, John Bissell, Dimitri A. Hirsch-Weil, Robert Joseph Araiza, Daniel R. Henton, James H. Plonka
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Patent number: 11905362Abstract: Provided herein are methods of producing polymers from furan and optionally diol compounds, using an organocatalyst. A polymer composition comprising a polymer prepared by the method is contemplated. Provided herein are also polymer compositions, such as poly(alkylene-2,5-furandicarboxylate). In some embodiments, polymer compositions have any one of the characteristics discussed herein, or any combinations thereof.Type: GrantFiled: December 23, 2021Date of Patent: February 20, 2024Assignee: Origin Materials Operating, Inc.Inventors: Makoto Nathanael Masuno, Dimitri A. Hirsch-Weil, Alexander Crewe-Read Millar, Alexander Yeuham Joh
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Publication number: 20230032460Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of C6 saccharides, including isomers thereof, polymers thereof, and certain derivatives thereof. The methods make use of acids with lower concentrations, and allows for conversion of sugars into 5-(halomethyl)furfural at higher temperatures and faster reaction or residence times.Type: ApplicationFiled: March 4, 2022Publication date: February 2, 2023Applicant: Origin Materials Operating, Inc.Inventors: Alex B. WOOD, Makoto N. MASUNO, Ryan L. SMITH, John BISSELL, Dimitri A. HIRSCH-WEIL, Robert Joseph ARAIZA, Daniel R. HENTON, James H. PLONKA
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Publication number: 20220372213Abstract: Provided herein are methods of producing polymers from furan and optionally diol compounds, using an organocatalyst. A polymer composition comprising a polymer prepared by the method is contemplated. Provided herein are also polymer compositions, such as poly(alkylene-2,5-furandicarboxylate). In some embodiments, polymer compositions have any one of the characteristics discussed herein, or any combinations thereof.Type: ApplicationFiled: December 23, 2021Publication date: November 24, 2022Applicant: Origin Materials Operating, Inc.Inventors: Makoto Nathanael MASUNO, Dimitri A. HIRSCH-WEIL, Alexander Crewe-Read MILLAR, Alexander Yeuham JOH
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Publication number: 20220144647Abstract: Provided is a method of producing activated carbon from a resin composite made up of furanic polymer. The method includes producing a resin composite from feedstock (e.g., in the presence of an acid and a salt), combining the resin composite with a base to form an impregnated material, and carbonizing the impregnated material to produce the and salt activated carbon. Provided herein are also resin composites and activated carbon materials.Type: ApplicationFiled: June 14, 2021Publication date: May 12, 2022Applicant: Origin Materials Operating, Inc.Inventors: Ryan L. SMITH, Thomas D. GREGORY, John Albert BISSELL, II, Shawn M. BROWNING, Alex B. WOOD, Robert Joseph ARAIZA, Paul J. DORNATH, Alex JOH, Dimitri A. HIRSCH-WEIL, Makoto N. MASUNO
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Patent number: 11299468Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of C6 saccharides, including isomers thereof, polymers thereof, and certain derivatives thereof. The methods make use of acids with lower concentrations, and allows for conversion of sugars into 5-(halomethyl)furfural at higher temperatures and faster reaction or residence times.Type: GrantFiled: June 5, 2020Date of Patent: April 12, 2022Assignee: Origin Materials Operating, Inc.Inventors: Alex B. Wood, Makoto N. Masuno, Ryan L. Smith, John Bissell, Dimitri A. Hirsch-Weil, Robert Joseph Araiza, Daniel R. Henton, James H. Plonka
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Publication number: 20210087157Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of C6 saccharides, including isomers thereof, polymers thereof, and certain derivatives thereof. The methods make use of acids with lower concentrations, and allows for conversion of sugars into 5-(halomethyl)furfural at higher temperatures and faster reaction or residence times.Type: ApplicationFiled: June 5, 2020Publication date: March 25, 2021Applicant: Micromidas, Inc.Inventors: Alex B. WOOD, Makoto N. MASUNO, Ryan L. SMITH, John BISSELL, Dimitri A. HIRSCH-WEIL, Robert Joseph ARAIZA, Daniel R. HENTON, James H. PLONKA
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Patent number: 10710970Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of C6 saccharides, including isomers thereof, polymers thereof, and certain derivatives thereof. The methods make use of acids with lower concentrations, and allows for conversion of sugars into 5-(halomethyl)furfural at higher temperatures and faster reaction or residence times.Type: GrantFiled: June 7, 2018Date of Patent: July 14, 2020Assignee: MICROMIDAS, INC.Inventors: Alex B. Wood, Makoto N. Masuno, Ryan L. Smith, John Bissell, Dimitri A. Hirsch-Weil, Robert Joseph Araiza, Daniel R. Henton, James H. Plonka
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Patent number: 10618880Abstract: Provided herein are methods of producing dialkylfurans, such as 2,5-dimethylfuran, and other alkyl furans, such as 2-methylfuran. For example, 2,5-dimethylfuran may be produced by reducing (5-methylfuran-2-yl)methanol or 2-(chloromethyl)-5-methylfuran.Type: GrantFiled: January 12, 2018Date of Patent: April 14, 2020Assignee: MICROMIDAS, INC.Inventors: Dimitri A. Hirsch-Weil, Makoto N. Masuno, John Bissell, Dennis A. Hucul, Alex B. Wood, Robert Joseph Araiza, Daniel R. Henton
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Patent number: 10414742Abstract: Provided herein are methods of producing dialkylfurans, such as 2,5-dimethylfuran, and other alkyl furans, such as 2-methylfuran. For example, 2,5-dimethylfuran may be produced by reducing (5-methylfuran-2-yl)methanol or 2-(chloromethyl)-5-methylfuran.Type: GrantFiled: November 1, 2017Date of Patent: September 17, 2019Assignee: MICROMIDAS, INC.Inventors: Dennis A. Hucul, Dimitri A. Hirsch-Weil, Makoto Nathanael Masuno, John Albert Bissell, II, Alex B. Wood, Robert Joseph Araiza, Daniel R. Henton, Shawn M. Browning, Ryan L. Smith
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Patent number: 10407547Abstract: Provided herein are methods of producing compounds, such as cyclohexanone, hexanediamine, hexanediol, hexamethylenediamine, caprolactam and nylon, from 5-(halomethyl)furfural.Type: GrantFiled: May 12, 2015Date of Patent: September 10, 2019Assignee: MICROMIDAS, INC.Inventors: Makoto Nathanael Masuno, Dimitri A. Hirsch-Weil, Ryan L. Smith, John Albert Bissell, II
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Patent number: 10392317Abstract: The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose, starch, sugar) and ethylene in the presence of a catalyst. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF), which may be converted into para-xylene by cycloaddition of ethylene to DMF. Para-xylene can then be oxidized to form terephthalic acid.Type: GrantFiled: September 13, 2013Date of Patent: August 27, 2019Assignee: MICROMIDAS, INC.Inventors: Makoto N. Masuno, Ryan L. Smith, John Bissell, II, Patrick B. Smith, Dennis A. Hucul, Edmund J. Stark, Daniel R. Henton, Adina Dumitrascu, Katherine Brune, Dimitri A. Hirsch-Weil
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Patent number: 10392358Abstract: Provided herein are methods of producing halomethylfuroic and acyloxymethylfuroic acid and ester compounds from furfural starting compounds. For example, 5-chloromethyl-2-furoic acid may be produced from 5-chloromethylfurfural, in the presence of various oxidants. Salts of the furoic acids may also be produced.Type: GrantFiled: September 16, 2016Date of Patent: August 27, 2019Assignee: Micromidas, Inc.Inventors: Daniel R. Henton, Makoto Nathanael Masuno, Ryan L. Smith, Alex B. Wood, Dimitri A. Hirsch-Weil, Christian T. Goralski, Robert Joseph Araiza
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Patent number: 10364210Abstract: Provided herein are (phenylene)dialkanamines, and methods of producing such (phenylene)dialkanamines from various furanyl and benzyl compounds. Such furanyl compounds may include, for example, bis(nitroalkyl)furans, bis(aminoalkyl)furans, and nitroalkyl(furan)acetonitriles. Such compounds may include, for example, bis(nitroalkyl)benzenes. Provided herein are also alkyldiamines, and methods for producing such alkyldiamines from furanyl compounds.Type: GrantFiled: August 27, 2015Date of Patent: July 30, 2019Assignee: MICROMIDAS, INC.Inventors: Alex B. Wood, Makoto Nathanael Masuno, Ryan L. Smith, John Albert Bissell, II, Robert Joseph Araiza, Dimitri A. Hirsch-Weil
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Publication number: 20190202977Abstract: Provided herein are methods of producing polymers from furan and optionally diol compounds, using an organocatalyst. A polymer composition comprising a polymer prepared by the method is contemplated. Provided herein are also polymer compositions, such as poly(alkylene-2,5-furandicarboxylate). In some embodiments, polymer compositions have any one of the characteristics discussed herein, or any combinations thereof.Type: ApplicationFiled: September 15, 2017Publication date: July 4, 2019Inventors: Makoto Nathanael MASUNO, Dimitri A. HIRSCH-WEIL, Alexander Crewe-Read MILLAR, Alexander Yeuham JOH
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Publication number: 20190144408Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of C6 saccharides, including isomers thereof, polymers thereof, and certain derivatives thereof. The methods make use of acids with lower concentrations, and allows for conversion of sugars into 5-(halomethyl)furfural at higher temperatures and faster reaction or residence times.Type: ApplicationFiled: June 7, 2018Publication date: May 16, 2019Applicant: MICROMIDAS, INC.Inventors: Alex B. WOOD, Makoto N. MASUNO, Ryan L. SMITH, John BISSELL, Dimitri A. HIRSCH-WEIL, Robert Joseph ARAIZA, Daniel R. HENTON, James H. PLONKA
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Publication number: 20180362484Abstract: Provided herein are methods of producing dialkylfurans, such as 2,5-dimethylfuran, and other alkyl furans, such as 2-methylfuran. For example, 2,5-dimethylfuran may be produced by reducing (5-methylfuran-2-yl)methanol or 2-(chloromethyl)-5-methylfuran.Type: ApplicationFiled: January 12, 2018Publication date: December 20, 2018Applicant: MICROMIDAS, INC.Inventors: Dimitri A. Hirsch-Weil, Makoto N. Masuno, John Bissell, Dennis A. Hucul, Alex B. Wood, Robert Joseph Araiza, Daniel R. Henton
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Patent number: 10125060Abstract: The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose, starch, sugar) and ethylene in the presence of a catalyst. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF), which may be converted into para-xylene by cycloaddition of ethylene to DMF. Para-xylene can then be oxidized to form terephthalic acid.Type: GrantFiled: January 21, 2016Date of Patent: November 13, 2018Assignee: MICROMIDAS, INC.Inventors: Makoto N. Masuno, Patrick B. Smith, Dennis A. Hucul, Katherine Brune, Ryan L. Smith, John A. Bissell, II, Dimitri Hirsch-Weil, Edmund J. Stark
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Publication number: 20180265629Abstract: Provided herein are methods of producing polymers from furan and optionally diol compounds, using an organocatalyst. The furan compounds may include, for example, 2,5-furandicarboxylic acid or 2,5-tetrahydrofurandicarboxylic acid. Provided herein are also polymer compositions, such as poly(alkylene-2,5-furandicarboxylate). The polymer compositions herein have a low metal content.Type: ApplicationFiled: September 16, 2016Publication date: September 20, 2018Applicant: Micromidas, Inc.Inventors: John Albert BISSELL, II, Makoto Nathanael MASUNO, Alexander Crewe-Read MILLAR, Dimitri A. HIRSCH-WEIL
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Publication number: 20180265488Abstract: Provided herein are methods of producing halomethylfuroic and acyloxymethylfuroic acid and ester compounds from furfural starting compounds. For example, 5-chloromethyl-2-furoic acid may be produced from 5-chloromethylfurfural, in the presence of various oxidants. Salts of the furoic acids may also be produced.Type: ApplicationFiled: September 16, 2016Publication date: September 20, 2018Applicant: Micromidas, Inc.Inventors: Daniel R. HENTON, Makoto Nathanael MASUNO, Ryan L. SMITH, Alex B. WOOD, Dimitri A. HIRSCH-WEIL, Christian T. GORALSKI, Robert Joseph ARAIZA