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：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：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：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.

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。