Patents by Inventor Makoto N. MASUNO
Makoto N. MASUNO 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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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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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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Patent number: 9359283Abstract: 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 31, 2013Date of Patent: June 7, 2016Assignee: Micromidas, Inc.Inventors: Ryan L. Smith, John Bissell, Makoto N. Masuno, Douglas Cannon, Alex B. Wood
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Patent number: 9260359Abstract: 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: September 14, 2012Date of Patent: February 16, 2016Assignee: Micromidas, Inc.Inventors: Makoto N. Masuno, Douglas Cannon, John Bissell, Ryan L. Smith, Alex Benjamin Wood, Patrick B. Smith, Dennis A. Hucul, Katherine Brune
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Publication number: 20160002190Abstract: 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: ApplicationFiled: September 11, 2015Publication date: January 7, 2016Applicant: MICROMIDAS, INC.Inventors: Shawn M. BROWNING, Makoto N. MASUNO, John BISSELL, II, Benjamin F. NICHOLSON
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Publication number: 20160002191Abstract: 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: September 11, 2015Publication date: January 7, 2016Applicant: MICROMIDAS, INC.Inventors: Alex B. WOOD, Shawn M. BROWNING, Makoto N. MASUNO, Ryan L. SMITH, John BISSELL, II
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Publication number: 20150376153Abstract: 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: ApplicationFiled: September 11, 2015Publication date: December 31, 2015Applicants: MICROMIDAS, INC., THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: Makoto N. MASUNO, Saikat DUTTA, Mark MASCAL
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Publication number: 20150266793Abstract: 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: September 13, 2013Publication date: September 24, 2015Applicant: MICROMIDAS, INC.Inventors: Makoto N. Masuno, Ryan L. Smith, John Bissell, II, Marc Foster, Patrick B. Smith, Dennis A. Hucul, Edmund J. Stark, Daniel R. Henton, Adina Dumitrascu, Katherine Brune
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Publication number: 20150266843Abstract: 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: ApplicationFiled: October 25, 2013Publication date: September 24, 2015Applicant: 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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Patent number: 9126964Abstract: 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: June 6, 2012Date of Patent: September 8, 2015Assignee: MICROMIDAS, INC.Inventors: Makoto N. Masuno, John Bissell, Ryan L. Smith, Brian Higgins, Alex Be. Wood
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Publication number: 20150148560Abstract: 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 31, 2013Publication date: May 28, 2015Applicant: MICROMIDAS, INC.Inventors: Ryan L. Smith, John Bissell, Makoto N. Masuno, Douglas Cannon, Alex B. Wood, Marc Foster
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Publication number: 20150141695Abstract: 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: October 20, 2014Publication date: May 21, 2015Applicant: MICROMIDAS, INC.Inventors: Makoto N. MASUNO, Patrick B. SMITH, Dennis A. HUCUL, Adina DUMITRASCU, Katherine BRUNE, Ryan L. SMITH, John A. BISSELL, Marc FOSTER
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Publication number: 20140350294Abstract: 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: September 14, 2012Publication date: November 27, 2014Applicant: MICROMIDAS, INC.Inventors: Makoto N. Masuno, Douglas Cannon, John Bissell, Ryan L. Smith, Marc Foster, Alex Benjamin Wood, Patrick B. Smith, Dennis A. Hucul
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Patent number: 8889938Abstract: 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: March 15, 2013Date of Patent: November 18, 2014Assignee: Micromidas, Inc.Inventors: Makoto N. Masuno, Patrick B. Smith, Dennis A. Hucul, Katherine Brune, Ryan L. Smith, John Bissell, Dimitri A. Hirsch-Weil, Edmund J. Stark