Patents Assigned to MICROMIDAS, INC.
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Patent number: 9908862Abstract: 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: August 15, 2014Date of Patent: March 6, 2018Assignee: 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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Publication number: 20180044311Abstract: 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: March 24, 2017Publication date: February 15, 2018Applicant: MICROMIDAS, INC.Inventors: Makoto Nathanael MASUNO, John BISSELL, II, Ryan L. SMITH, Brian HIGGINS, Alex B. WOOD
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Patent number: 9890101Abstract: The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose) and ethylene in the presence of an acid, such as a Lewis acid. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF) and 2-methylfuran, which may be converted into para-xylene and toluene, respectively. In particular, para-xylene can then be oxidized to form terephthalic acid.Type: GrantFiled: January 12, 2016Date of Patent: February 13, 2018Assignee: MICROMIDAS, INC.Inventors: Makoto N. Masuno, Douglas Cannon, John Bissell, II, Ryan L. Smith, Alex B. Wood, Patrick B. Smith, Dennis A. Hucul, Katherine Brune
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Patent number: 9840486Abstract: 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 hydrogenation of (5-methylfuran-2-yl) methanol or 2-(chloromethyl)-5-methylfuran in the presence of a solid supported metal catalyst having an excess of either basic or acidic sites (as determined by chemisorption of CO2 or NH3). The process could further include a urea reagent (TMU, DMPU, TMI) and an alkyl benzene.Type: GrantFiled: August 14, 2015Date of Patent: December 12, 2017Assignee: 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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Publication number: 20170275236Abstract: 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: ApplicationFiled: August 27, 2015Publication date: September 28, 2017Applicant: 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: 20170267654Abstract: 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 hydrogenation of (5-methylfuran-2-yl) methanol or 2-(chloromethyl)-5-methylfuran in the presence of a solid supported metal catalyst having an excess of either basic or acidic sites (as determined by chemisorption of CO2 or NH3). The process could further include a urea reagent (TMU, DMPU, TMI) and an alkyl benzene.Type: ApplicationFiled: August 14, 2015Publication date: September 21, 2017Applicant: 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: 9718798Abstract: Provided are solid forms of 5-(halomethyl)furfural, including a crystalline form of 5-(chloromethyl)furfural. Provided are also methods for preparing solid forms of 5-(halomethyl)furfural by crystallization using certain solvents.Type: GrantFiled: September 11, 2015Date of Patent: August 1, 2017Assignee: MICROMIDAS, INC.Inventors: Shawn M. Browning, Makoto N. Masuno, John Bissell, II, Benjamin F. Nicholson
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Patent number: 9688603Abstract: Provided herein are methods that utilize polyhydroxyalkanoates (PHAs) as a substrate for further conversion to C4 and C5 compounds. Polyhydroxyalkanoates can undergo esterification to yield alkyl hydroxyalkanoates and alkyl alkenoates, which may serve as useful precursors in the production of alkadienes and alkenedioic acids, including for example butadiene and butenedioic acid.Type: GrantFiled: May 13, 2016Date of Patent: June 27, 2017Assignee: MICROMIDAS, INC.Inventors: Ryan L. Smith, John Bissell, Makoto N. Masuno, Douglas Cannon, Alex B. Wood
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Publication number: 20170137397Abstract: 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: January 27, 2017Publication date: May 18, 2017Applicant: MICROMIDAS, INC.Inventors: Alex B. WOOD, Shawn M. BROWNING, Makoto N. MASUNO, Ryan L. SMITH, John BISSELL, II
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Patent number: 9637463Abstract: 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: July 21, 2015Date of Patent: May 2, 2017Assignee: MICROMIDAS, INC.Inventors: Makoto Nathanael Masuno, John Bissell, II, Ryan L. Smith, Brian Higgins, Alex B. Wood
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Publication number: 20170096385Abstract: Provided herein are methods that utilize polyhydroxyalkanoates (PHAs) as a substrate for further conversion to C4 and C5 compounds. Polyhydroxyalkanoates can undergo esterification to yield alkyl hydroxyalkanoates and alkyl alkenoates, which may serve as useful precursors in the production of alkadienes and alkenedioic acids, including for example butadiene and butenedioic acid.Type: ApplicationFiled: May 13, 2016Publication date: April 6, 2017Applicant: MICROMIDAS, INC.Inventors: Ryan L. SMITH, John BISSELL, Makoto N. MASUNO, Douglas CANNON, Alex B. WOOD
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Publication number: 20170081470Abstract: Provided herein are methods of producing compounds, such as cyclohexanone, hexanediamine, hexanediol, hexamethylenediamine, caprolactam and nylon, from 5-(halomethyl)furfural.Type: ApplicationFiled: May 12, 2015Publication date: March 23, 2017Applicant: MICROMIDAS, INC.Inventors: Makoto Nathanael MASUNO, Dimitri A. HIRSCH-WEIL, Ryan L. SMITH, John Albert BISSELL, II
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Patent number: 9586922Abstract: 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: September 11, 2015Date of Patent: March 7, 2017Assignee: MICROMIDAS, INC.Inventors: Alex B. Wood, Shawn M. Browning, Makoto N. Masuno, Ryan L. Smith, John Bissell, II
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Patent number: 9556137Abstract: Provided herein are methods for preparing alkylfurans, such as 2,5-dialkylfurans and 2-alkylfurans. Furfural or 5-alkylfurfural can be reacted with aniline or diaminobenzene, or derivatives thereof, to form the corresponding imine, which can be reduced to form alkylfurans and to regenerate the aniline or diaminobenzene, or derivatives thereof. The alkylfuran may be, for example, 2,5-dimethylfuran or 2-methylfuran.Type: GrantFiled: September 11, 2015Date of Patent: January 31, 2017Assignees: Micromidas, inc., The Regents Of The University of CaliforniaInventors: Makoto N. Masuno, Saikat Dutta, Mark Mascal
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Publication number: 20160368837Abstract: 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: ApplicationFiled: January 21, 2016Publication date: December 22, 2016Applicant: MICROMIDAS, INC.Inventors: Makoto N. MASUNO, Patrick B. SMITH, Dennis A. HUCUL, Adina DUMITRASCU, Katherine BRUNE, Ryan L. SMITH, John A. BISSELL, II, Marc FOSTER
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Publication number: 20160362357Abstract: The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose) and ethylene in the presence of an acid, such as a Lewis acid. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF) and 2-methylfuran, which may be converted into para-xylene and toluene, respectively. In particular, para-xylene can then be oxidized to form terephthalic acid.Type: ApplicationFiled: January 12, 2016Publication date: December 15, 2016Applicant: MICROMIDAS, INC.Inventors: Makoto N. MASUNO, Douglas CANNON, John BISSELL, II, Ryan L. SMITH, Alex B. WOOD, Patrick B. SMITH, Dennis A. HUCUL
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Publication number: 20160207897Abstract: 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: September 19, 2014Publication date: July 21, 2016Applicant: MICROMIDAS, INC.Inventors: Alex B. WOOD, Makoto N. MASUNO, Ryan L. SMITH, John BISSEL, Dimitri A. HIRSCH-WEIL, Robert Joseph ARAIZA, Daniel R. HENTON, James H. PLONKA
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Publication number: 20160200700Abstract: 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: August 15, 2014Publication date: July 14, 2016Applicant: 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: 9388151Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of biomass. The methods make use of certain organic solvents with temperature-dependent solubility for 5-(halomethyl)furfural. This allows for temperature-dependent phase separation of the 5-(halomethyl)furfural from the reaction mixture. In certain embodiments, solid 5-(halomethyl)furfural may be obtained. The solid 5-(halomethyl)furfural obtained may be amorphous or crystalline.Type: GrantFiled: October 25, 2013Date of Patent: July 12, 2016Assignee: Micromidas, Inc.Inventors: Shawn M. Browning, John Bissell, II, Ryan L. Smith, Makoto N. Masuno, Benjamin F. Nicholson, Alex B. Wood
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Publication number: 20160168107Abstract: 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: July 21, 2015Publication date: June 16, 2016Applicant: MICROMIDAS, INC.Inventors: Makoto Nathanael MASUNO, John BISSELL, II, Ryan L. SMITH, Brian HIGGINS, Alex B. WOOD