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：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。

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：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：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：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：US09840486B2

公开(公告)日：2017-12-12

申请号：US15503681

申请日：2015-08-14

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 ,  C07C2/86

CPC classification number: C07D307/36 ,  C07C2/865 ,  C07D307/38 ,  C07D307/44 ,  C07D307/48

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 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.

公开(公告)号：US20160200700A1

公开(公告)日：2016-07-14

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

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.

Abstract translation: 本文提供了生产二烷基呋喃的方法，例如2,5-二甲基呋喃和其它烷基呋喃，如2-甲基呋喃。 例如，可以通过还原（5-甲基呋喃-2-基）甲醇或2-（氯甲基）-5-甲基呋喃来制备2,5-二甲基呋喃。