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公开(公告)号：US09556137B2
公开(公告)日：2017-01-31
申请号：US14852134
申请日：2015-09-11
Inventor： Makoto N. Masuno , Saikat Dutta , Mark Mascal
IPC: C07D307/36 , C07D307/52
CPC classification number: C07D307/36 , C07D307/52 , Y02P20/582
Abstract: 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.
Abstract translation: 本文提供了制备烷基呋喃的方法，例如2,5-二烷基呋喃和2-烷基呋喃。 糠醛或5-烷基糠醛可以与苯胺或二氨基苯或其衍生物反应形成相应的亚胺，其可以还原形成烷基呋喃并使苯胺或二氨基苯或其衍生物再生。 烷基呋喃可以是例如2,5-二甲基呋喃或2-甲基呋喃。
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公开(公告)号：US09388151B2
公开(公告)日：2016-07-12
申请号：US14438600
申请日：2013-10-25
Applicant: MICROMIDAS, INC.
Inventor： Shawn M. Browning , John Bissell, II , Ryan L. Smith , Makoto N. Masuno , Benjamin F. Nicholson , Alex B. Wood
IPC: C07D307/50
CPC classification number: C07D307/50
Abstract: 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.
Abstract translation: 本公开提供通过酸催化转化生物质来生产5-（卤甲基）糠醛的方法，包括5-（氯甲基）糠醛。 该方法利用某些具有温度依赖性溶解度的有机溶剂对5-（卤甲基）糠醛。 这允许5-（卤甲基）糠醛与反应混合物的温度依赖性相分离。 在某些实施方案中，可以获得固体5-（卤代甲基）糠醛。 得到的固体5-（卤甲基）糠醛可以是无定形或结晶的。
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公开(公告)号：US09359283B2
公开(公告)日：2016-06-07
申请号：US14404384
申请日：2013-05-31
Applicant: MICROMIDAS, INC.
Inventor： Ryan L. Smith , John Bissell , Makoto N. Masuno , Douglas Cannon , Alex B. Wood
CPC classification number: C07C67/31 , C07C1/24 , C07C29/095 , C07C29/149 , C07C51/16 , C07C67/03 , C07C67/30 , C07C2527/167 , C07C69/675 , C07C69/533 , C07C11/167 , C07C57/15 , C07C69/56 , C07C31/207
Abstract: 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.
Abstract translation: 本文提供了利用聚羟基链烷酸酯（PHA）作为底物进一步转化成C4和C5化合物的方法。 聚羟基链烷酸酯可以进行酯化以得到烷基羟基链烷酸酯和烷基链烯酸酯，其可用作生产烷二烯和烯二酸的有用前体，包括例如丁二烯和丁烯二酸。
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公开(公告)号：US20150266793A1
公开(公告)日：2015-09-24
申请号：US14428339
申请日：2013-09-13
Applicant: MICROMIDAS, INC.
Inventor： 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
IPC: C07C2/86
CPC classification number: C07C2/867 , C07C6/04 , C07C2521/04 , C07C2521/18 , C07C2523/08 , C07C2523/10 , C07C2523/72 , C07C2527/122 , C07C2527/125 , C07C2527/126 , C07C2527/128 , C07C2527/133 , C07C2527/135 , C07C2527/138 , C07C2527/18 , C07C2527/19 , C07C2529/14 , C07C2529/24 , C07C2531/025 , C07C2531/04 , C07C2531/22 , C07C15/08
Abstract: 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.
Abstract translation: 本公开提供了在催化剂存在下从可再生来源（例如纤维素，半纤维素，淀粉，糖）和乙烯生产对二甲苯，甲苯和其它化合物的方法。 例如，纤维素和/或半纤维素可以转化成2,5-二甲基呋喃（DMF），其可以通过乙烯与DMF的加成转化成对二甲苯。 然后可以将对二甲苯氧化形成对苯二甲酸。
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公开(公告)号：US10125060B2
公开(公告)日：2018-11-13
申请号：US15003613
申请日：2016-01-21
Applicant: MICROMIDAS, INC.
Inventor： Makoto N. Masuno , Patrick B. Smith , Dennis A. Hucul , Katherine Brune , Ryan L. Smith , John A. Bissell, II , Dimitri Hirsch-Weil , Edmund J. Stark
Abstract: 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.
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Patent Agency Ranking
公开(公告)号：US10011577B2
公开(公告)日：2018-07-03
申请号：US15022882
申请日：2014-09-19
Applicant: MICROMIDAS, INC.
Inventor： Alex B. Wood , Makoto N. Masuno , Ryan L. Smith , John Bissell , Dimitri A. Hirsch-Weil , Robert Joseph Araiza , Daniel R. Henton , James H. Plonka
IPC: C07D307/46 , C07D307/50 , B01J27/10
CPC classification number: C07D307/46 , B01J27/10 , C07D307/50
Abstract: 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.
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公开(公告)号：US09908862B2
公开(公告)日：2018-03-06
申请号：US14912052
申请日：2014-08-15
Applicant: MICROMIDAS, INC.
Inventor： Dimitri A. Hirsch-Weil , Makoto N. Masuno , John Bissell , Dennis A. Hucul , Alex B. Wood , Robert Joseph Araiza , Daniel R. Henton
IPC: C07D307/36 , C07D307/34
CPC classification number: C07D307/36 , C07D307/34
Abstract: 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.
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公开(公告)号：US09890101B2
公开(公告)日：2018-02-13
申请号：US14993833
申请日：2016-01-12
Applicant: MICROMIDAS, INC.
Inventor： Makoto N. Masuno , Douglas Cannon , John Bissell, II , Ryan L. Smith , Alex B. Wood , Patrick B. Smith , Dennis A. Hucul , Katherine Brune
CPC classification number: C07C51/16 , C07C2/52 , C07C2/862 , C07C2/865 , C07C15/08 , C07C2521/18 , C07C2527/02 , C07C2527/053 , C07C2527/08 , C07C2527/10 , C07C2527/122 , C07C2527/126 , C07C2527/128 , C07C2527/132 , C07C2527/133 , C07C2527/135 , C07C2527/138 , C07C2527/14 , C07C2527/16 , C07C2529/08 , C07C2529/14 , C07C2529/24 , C07C2531/02 , C07C2531/04 , C07C2531/12 , C07C15/06
Abstract: 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.
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公开(公告)号：US09718798B2
公开(公告)日：2017-08-01
申请号：US14852152
申请日：2015-09-11
Applicant: MICROMIDAS, INC.
Inventor： Shawn M. Browning , Makoto N. Masuno , John Bissell, II , Benjamin F. Nicholson
IPC: C07D307/18 , C07D307/46 , C07D307/48
CPC classification number: C07D307/46 , C07D307/18 , C07D307/48
Abstract: 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.
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公开(公告)号：US20150266843A1
公开(公告)日：2015-09-24
申请号：US14438600
申请日：2013-10-25
Applicant: MICROMIDAS, INC.
Inventor： Shawn M. Browning , John Bissell, II , Ryan L. Smith , Makoto N. Masuno , Benjamin F. Nicholson , Alex B. Wood
IPC: C07D307/50
CPC classification number: C07D307/50
Abstract: 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.
Abstract translation: 本公开提供通过酸催化转化生物质来生产5-（卤甲基）糠醛的方法，包括5-（氯甲基）糠醛。 该方法利用某些具有温度依赖性溶解度的有机溶剂对5-（卤甲基）糠醛。 这允许5-（卤甲基）糠醛与反应混合物的温度依赖性相分离。 在某些实施方案中，可以获得固体5-（卤代甲基）糠醛。 得到的固体5-（卤甲基）糠醛可以是无定形或结晶的。
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