公开(公告)号：US20180362484A1

公开(公告)日：2018-12-20

申请号：US15870691

申请日：2018-01-12

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

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.

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.

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.

公开(公告)号：US08889938B2

公开(公告)日：2014-11-18

申请号：US13838761

申请日：2013-03-15

Applicant: Micromidas, Inc.

Inventor： Makoto N. Masuno ,  Patrick B. Smith ,  Dennis A. Hucul ,  Katherine Brune ,  Ryan L. Smith ,  John Bissell ,  Dimitri A. Hirsch-Weil ,  Edmund J. Stark

IPC: C07C2/06 ,  C07C51/16 ,  C07C2/86

CPC classification number: C07C2/867 ,  C07C51/16 ,  C07C2521/18 ,  C07C2527/10 ,  C07C2527/122 ,  C07C2527/125 ,  C07C2527/126 ,  C07C2527/128 ,  C07C2527/133 ,  C07C2527/135 ,  C07C2527/138 ,  C07C2527/167 ,  C07C2527/18 ,  C07C2527/188 ,  C07C2529/08 ,  C07C2529/24 ,  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。

公开(公告)号：US10414742B2

公开(公告)日：2019-09-17

申请号：US15801235

申请日：2017-11-01

Applicant: MICROMIDAS, INC.

Inventor： 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

IPC: C07D307/36 ,  C07D307/38 ,  C07D307/44 ,  C07D307/48 ,  C07C2/86

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.

公开(公告)号：US10407547B2

公开(公告)日：2019-09-10

申请号：US15310728

申请日：2015-05-12

Applicant: MICROMIDAS, INC.

Inventor： Makoto Nathanael Masuno ,  Dimitri A. Hirsch-Weil ,  Ryan L. Smith ,  John Albert Bissell, II

IPC: C07D307/16 ,  C08G69/08 ,  C07C209/68 ,  C08G69/04 ,  C08G69/26 ,  C08G69/28 ,  C07C29/132 ,  C07C29/149 ,  C07C45/29 ,  C07C45/66 ,  C07D223/10 ,  C07D307/52

Abstract: Provided herein are methods of producing compounds, such as cyclohexanone, hexanediamine, hexanediol, hexamethylenediamine, caprolactam and nylon, from 5-(halomethyl)furfural.

公开(公告)号：US10392358B2

公开(公告)日：2019-08-27

申请号：US15760949

申请日：2016-09-16

Applicant: Micromidas, Inc.

Inventor： Daniel R. Henton ,  Makoto Nathanael Masuno ,  Ryan L. Smith ,  Alex B. Wood ,  Dimitri A. Hirsch-Weil ,  Christian T. Goralski ,  Robert Joseph Araiza

IPC: C07D307/02 ,  C07D307/54 ,  B01J19/00

Abstract: 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.

公开(公告)号：US10392317B2

公开(公告)日：2019-08-27

申请号：US14428339

申请日：2013-09-13

Applicant: MICROMIDAS, INC.

Inventor： 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

IPC: C07C6/04 ,  C07C2/86

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.

公开(公告)号：US10710970B2

公开(公告)日：2020-07-14

申请号：US16002537

申请日：2018-06-07

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: C07D307/48 ,  C07D307/46 ,  C07D307/50 ,  B01J27/10

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.

公开(公告)号：US10364210B2

公开(公告)日：2019-07-30

申请号：US15507009

申请日：2015-08-27

Applicant: MICROMIDAS, INC.

Inventor： Alex B. Wood ,  Makoto Nathanael Masuno ,  Ryan L. Smith ,  John Albert Bissell, II ,  Robert Joseph Araiza ,  Dimitri A. Hirsch-Weil

IPC: C07D307/02 ,  C07C211/51 ,  C07D307/14 ,  C07D307/38 ,  C07D307/42 ,  C07D307/52 ,  C07D307/54 ,  C07C205/04 ,  C07C211/09 ,  C07C211/27 ,  C07C255/35 ,  C08G69/04 ,  C08G69/08 ,  C08G69/26 ,  C08G69/28 ,  C07C209/32 ,  C08F210/02 ,  C08G73/02

Abstract: 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.