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：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：US20180044311A1

公开(公告)日：2018-02-15

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: C07D307/50 ,  C07D307/46

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：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：US20170137397A1

公开(公告)日：2017-05-18

申请号：US15418385

申请日：2017-01-27

Applicant: MICROMIDAS, INC.

Inventor： Alex B. WOOD ,  Shawn M. BROWNING ,  Makoto N. MASUNO ,  Ryan L. SMITH ,  John BISSELL, II

IPC: C07D307/48

CPC classification number: C07D307/48 ,  C07D307/46

Abstract: The present disclosure provides methods for purifying a 5-(halomethyl)furfural composition, including 5-(chloromethyl)furfural, at operating conditions that decrease or minimize the decomposition or degradation of 5-(chloromethyl)furfural during the process. The methods may employ certain solvents, operating conditions, and/or techniques (e.g., gas stripping). The gaseous 5-(halomethyl)furfural produced from the process can be condensed or deposited to yield 5-(halomethyl)furfural in liquid or solid form. The solid 5-(halomethyl)furfural may be amorphous or crystalline.

公开(公告)号：US20170096385A1

公开(公告)日：2017-04-06

申请号：US15154804

申请日：2016-05-13

Applicant: MICROMIDAS, INC.

Inventor： Ryan L. SMITH ,  John BISSELL ,  Makoto N. MASUNO ,  Douglas CANNON ,  Alex B. WOOD

IPC: C07C67/31 ,  C07C67/30

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.

公开(公告)号：US20170081470A1

公开(公告)日：2017-03-23

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

CPC classification number: C08G69/08 ,  C07C29/132 ,  C07C29/149 ,  C07C45/29 ,  C07C45/66 ,  C07C209/68 ,  C07C2601/14 ,  C07D223/10 ,  C07D307/16 ,  C07D307/52 ,  C08G69/04 ,  C08G69/26 ,  C08G69/28 ,  C07C211/12

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：US20160207897A1

公开(公告)日：2016-07-21

申请号：US15022882

申请日：2014-09-19

Applicant: MICROMIDAS, INC.

Inventor： Alex B. WOOD ,  Makoto N. MASUNO ,  Ryan L. SMITH ,  John BISSEL ,  Dimitri A. HIRSCH-WEIL ,  Robert Joseph ARAIZA ,  Daniel R. HENTON ,  James H. PLONKA

IPC: C07D307/46

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.

Abstract translation: 本公开内容提供了通过C6糖的酸催化转化，包括其异构体，其聚合物及其某些衍生物来生产5-（卤甲基）糠醛的方法，包括5-（氯甲基）糠醛。 该方法利用较低浓度的酸，并允许在更高的温度和更快的反应或停留时间将糖转化为5-（卤甲基）糠醛。

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。