Patents Assigned to MICROMIDAS, INC.
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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: 10604498Abstract: The present disclosure provides methods for purifying a 5-(halomethyl)furfural composition, including 5-(chloromethyl)furfural, at operating conditions that decrease or minimize the decomposition or degradation of 5-(chloromethyl)furfural during the process. The methods may employ certain solvents, operating conditions, and/or techniques (e.g., gas stripping). The gaseous 5-(halomethyl)furfural produced from the process can be condensed or deposited to yield 5-(halomethyl)furfural in liquid or solid form. The solid 5-(halomethyl)furfural may be amorphous or crystalline.Type: GrantFiled: August 1, 2018Date of Patent: March 31, 2020Assignee: MICROMIDAS, INC.Inventors: Alex B. Wood, Shawn M. Browning, Makoto N. Masuno, Ryan L. Smith, John Bissell, II
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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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Publication number: 20190270717Abstract: The present disclosure provides methods to produce substituted furans (e.g., halomethylfurfural, hydroxymethylfurfural, and furfural), by acid-catalyzed conversion of biomass using a gaseous acid in a multiphase reactor, such as a fluidized bed reactor.Type: ApplicationFiled: September 14, 2018Publication date: September 5, 2019Applicant: MICROMIDAS, INC.Inventors: Makoto Nathanael MASUNO, John BISSELL, II, Ryan L. SMITH, Brian HIGGINS, Alex B. WOOD
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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: 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: 20190062292Abstract: The present disclosure provides methods for purifying a 5-(halomethyl)furfural composition, including 5-(chloromethyl)furfural, at operating conditions that decrease or minimize the decomposition or degradation of 5-(chloromethyl)furfural during the process. The methods may employ certain solvents, operating conditions, and/or techniques (e.g., gas stripping). The gaseous 5-(halomethyl)furfural produced from the process can be condensed or deposited to yield 5-(halomethyl)furfural in liquid or solid form. The solid 5-(halomethyl)furfural may be amorphous or crystalline.Type: ApplicationFiled: August 1, 2018Publication date: February 28, 2019Applicant: MICROMIDAS, INC.Inventors: Alex B. WOOD, Shawn M. BROWNING, Makoto N. MASUNO, Ryan L. SMITH, John BISSELL, II
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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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Patent number: 10093638Abstract: The present disclosure provides methods to produce substituted furans (e.g., halomethylfurfural, hydroxymethylfurfural, and furfural), by acid-catalyzed conversion of biomass using a gaseous acid in a multiphase reactor, such as a fluidized bed reactor.Type: GrantFiled: March 24, 2017Date of Patent: October 9, 2018Assignee: MICROMIDAS, INC.Inventors: Makoto Nathanael Masuno, John Bissell, II, Ryan L. Smith, Brian Higgins, Alex B. Wood
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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
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Patent number: 10053441Abstract: The present disclosure provides methods for purifying a 5-(halomethyl)furfural composition, including 5-(chloromethyl)furfural, at operating conditions that decrease or minimize the decomposition or degradation of 5-(chloromethyl)furfural during the process. The methods may employ certain solvents, operating conditions, and/or techniques (e.g., gas stripping). The gaseous 5-(halomethyl)furfural produced from the process can be condensed or deposited to yield 5-(halomethyl)furfural in liquid or solid form. The solid 5-(halomethyl)furfural may be amorphous or crystalline.Type: GrantFiled: January 27, 2017Date of Patent: August 21, 2018Assignee: MICROMIDAS, INC.Inventors: Alex B. Wood, Shawn M. Browning, Makoto N. Masuno, Ryan L. Smith, John Bissell, II
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Patent number: 10011577Abstract: 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: September 19, 2014Date of Patent: July 3, 2018Assignee: 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: 20180065944Abstract: 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: November 1, 2017Publication date: March 8, 2018Applicant: 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