公开(公告)号：US09637463B2

公开(公告)日：2017-05-02

申请号：US14805321

申请日：2015-07-21

Applicant: MICROMIDAS, INC.

Inventor： Makoto Nathanael Masuno ,  John Bissell, II ,  Ryan L. Smith ,  Brian Higgins ,  Alex B. Wood

IPC: C07D307/46 ,  C07D307/50

CPC classification number: C07D307/50 ,  C07D307/46

Abstract: 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.

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：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：US10093638B2

公开(公告)日：2018-10-09

申请号：US15468728

申请日：2017-03-24

Applicant: MICROMIDAS, INC.

Inventor： Makoto Nathanael Masuno ,  John Bissell, II ,  Ryan L. Smith ,  Brian Higgins ,  Alex B. Wood

IPC: C07D307/46 ,  C07D307/50

Abstract: 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.

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.