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：US09890101B2

公开(公告)日：2018-02-13

申请号：US14993833

申请日：2016-01-12

Applicant: MICROMIDAS, INC.

Inventor： Makoto N. Masuno ,  Douglas Cannon ,  John Bissell, II ,  Ryan L. Smith ,  Alex B. Wood ,  Patrick B. Smith ,  Dennis A. Hucul ,  Katherine Brune

IPC: C07C51/16 ,  C07C2/86 ,  C07C2/52 ,  C07C15/08

CPC classification number: C07C51/16 ,  C07C2/52 ,  C07C2/862 ,  C07C2/865 ,  C07C15/08 ,  C07C2521/18 ,  C07C2527/02 ,  C07C2527/053 ,  C07C2527/08 ,  C07C2527/10 ,  C07C2527/122 ,  C07C2527/126 ,  C07C2527/128 ,  C07C2527/132 ,  C07C2527/133 ,  C07C2527/135 ,  C07C2527/138 ,  C07C2527/14 ,  C07C2527/16 ,  C07C2529/08 ,  C07C2529/14 ,  C07C2529/24 ,  C07C2531/02 ,  C07C2531/04 ,  C07C2531/12 ,  C07C15/06

Abstract: The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose) and ethylene in the presence of an acid, such as a Lewis acid. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF) and 2-methylfuran, which may be converted into para-xylene and toluene, respectively. In particular, para-xylene can then be oxidized to form terephthalic acid.

公开(公告)号：US09718798B2

公开(公告)日：2017-08-01

申请号：US14852152

申请日：2015-09-11

Applicant: MICROMIDAS, INC.

Inventor： Shawn M. Browning ,  Makoto N. Masuno ,  John Bissell, II ,  Benjamin F. Nicholson

IPC: C07D307/18 ,  C07D307/46 ,  C07D307/48

CPC classification number: C07D307/46 ,  C07D307/18 ,  C07D307/48

Abstract: Provided are solid forms of 5-(halomethyl)furfural, including a crystalline form of 5-(chloromethyl)furfural. Provided are also methods for preparing solid forms of 5-(halomethyl)furfural by crystallization using certain solvents.

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：US20160368837A1

公开(公告)日：2016-12-22

申请号：US15003613

申请日：2016-01-21

Applicant: MICROMIDAS, INC.

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

IPC: C07C2/86 ,  C07C51/16

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：US20160168107A1

公开(公告)日：2016-06-16

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: C07D307/50

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.

Abstract translation: 本公开提供了通过在多相反应器如流化床反应器中使用气态酸的酸催化转化生物质来生产取代呋喃（例如卤代甲基糠醛，羟甲基糠醛和糠醛）的方法。

公开(公告)号：US20150266843A1

公开(公告)日：2015-09-24

申请号：US14438600

申请日：2013-10-25

Applicant: MICROMIDAS, INC.

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

IPC: C07D307/50

CPC classification number: C07D307/50

Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of biomass. The methods make use of certain organic solvents with temperature-dependent solubility for 5-(halomethyl)furfural. This allows for temperature-dependent phase separation of the 5-(halomethyl)furfural from the reaction mixture. In certain embodiments, solid 5-(halomethyl)furfural may be obtained. The solid 5-(halomethyl)furfural obtained may be amorphous or crystalline.

Abstract translation: 本公开提供通过酸催化转化生物质来生产5-（卤甲基）糠醛的方法，包括5-（氯甲基）糠醛。 该方法利用某些具有温度依赖性溶解度的有机溶剂对5-（卤甲基）糠醛。 这允许5-（卤甲基）糠醛与反应混合物的温度依赖性相分离。 在某些实施方案中，可以获得固体5-（卤代甲基）糠醛。 得到的固体5-（卤甲基）糠醛可以是无定形或结晶的。

公开(公告)号：US08889938B2

公开(公告)日：2014-11-18

申请号：US13838761

申请日：2013-03-15

Applicant: Micromidas, Inc.

Inventor： Makoto N. Masuno ,  Patrick B. Smith ,  Dennis A. Hucul ,  Katherine Brune ,  Ryan L. Smith ,  John Bissell ,  Dimitri A. Hirsch-Weil ,  Edmund J. Stark

IPC: C07C2/06 ,  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.

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：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.