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：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.

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：US10604498B2

公开(公告)日：2020-03-31

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：US10053441B2

公开(公告)日：2018-08-21

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：US09388151B2

公开(公告)日：2016-07-12

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：US20150266793A1

公开(公告)日：2015-09-24

申请号：US14428339

申请日：2013-09-13

Applicant: MICROMIDAS, INC.

Inventor： Makoto N. Masuno ,  Ryan L. Smith ,  John Bissell, II ,  Marc Foster ,  Patrick B. Smith ,  Dennis A. Hucul ,  Edmund J. Stark ,  Daniel R. Henton ,  Adina Dumitrascu ,  Katherine Brune

IPC: C07C2/86

CPC classification number: C07C2/867 ,  C07C6/04 ,  C07C2521/04 ,  C07C2521/18 ,  C07C2523/08 ,  C07C2523/10 ,  C07C2523/72 ,  C07C2527/122 ,  C07C2527/125 ,  C07C2527/126 ,  C07C2527/128 ,  C07C2527/133 ,  C07C2527/135 ,  C07C2527/138 ,  C07C2527/18 ,  C07C2527/19 ,  C07C2529/14 ,  C07C2529/24 ,  C07C2531/025 ,  C07C2531/04 ,  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：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.