公开(公告)号：US20190062292A1

公开(公告)日：2019-02-28

申请号：US16052203

申请日：2018-08-01

Applicant: MICROMIDAS, INC.

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

IPC: 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：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：US09586922B2

公开(公告)日：2017-03-07

申请号：US14852306

申请日：2015-09-11

Applicant: MICROMIDAS, INC.

Inventor： Alex B. Wood ,  Shawn M. Browning ,  Makoto N. Masuno ,  Ryan L. Smith ,  John Bissell, II

IPC: C07D307/48 ,  C07D307/46

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.

Abstract translation: 本公开提供在操作条件下纯化5-（卤代甲基）糠醛组合物的方法，其包括5-（氯甲基）糠醛，其在该过程中减少或最小化5-（氯甲基）糠醛的分解或降解。 这些方法可以使用某些溶剂，操作条件和/或技术（例如，汽提）。 从该方法产生的气态5-（卤代甲基）糠醛可以冷凝或沉积以产生液体或固体形式的5-（卤甲基）糠醛。 固体5-（卤甲基）糠醛可以是无定形或结晶的。

公开(公告)号：US20150376153A1

公开(公告)日：2015-12-31

申请号：US14852134

申请日：2015-09-11

Applicant: MICROMIDAS, INC. ,  THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

Inventor： Makoto N. MASUNO ,  Saikat DUTTA ,  Mark MASCAL

IPC: C07D307/36

CPC classification number: C07D307/36 ,  C07D307/52 ,  Y02P20/582

Abstract: Provided herein are methods for preparing alkylfurans, such as 2,5-dialkylfurans and 2-alkylfurans. Furfural or 5-alkylfurfural can be reacted with aniline or diaminobenzene, or derivatives thereof, to form the corresponding imine, which can be reduced to form alkylfurans and to regenerate the aniline or diaminobenzene, or derivatives thereof. The alkylfuran may be, for example, 2,5-dimethylfuran or 2-methylfuran.

Abstract translation: 本文提供了制备烷基呋喃的方法，例如2,5-二烷基呋喃和2-烷基呋喃。 糠醛或5-烷基糠醛可以与苯胺或二氨基苯或其衍生物反应形成相应的亚胺，其可以还原形成烷基呋喃并使苯胺或二氨基苯或其衍生物再生。 烷基呋喃可以是例如2,5-二甲基呋喃或2-甲基呋喃。

公开(公告)号：US20130245316A1

公开(公告)日：2013-09-19

申请号：US13838761

申请日：2013-03-15

Applicant: MICROMIDAS, INC.

Inventor： Makoto N. MASUNO ,  Patrick B. SMITH ,  Dennis A. HUCUL ,  Adina DUMITRASCU ,  Katherine BRUNE ,  Ryan L. SMITH ,  John BISSELL ,  Marc FOSTER

IPC: 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.

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：US20190270717A1

公开(公告)日：2019-09-05

申请号：US16132321

申请日：2018-09-14

Applicant: MICROMIDAS, INC.

Inventor： Makoto Nathanael MASUNO ,  John BISSELL, II ,  Ryan L. SMITH ,  Brian HIGGINS ,  Alex B. WOOD

IPC: 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：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.