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：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：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：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。

公开(公告)号：US20150148560A1

公开(公告)日：2015-05-28

申请号：US14404384

申请日：2013-05-31

Applicant: MICROMIDAS, INC.

Inventor： Ryan L. Smith ,  John Bissell ,  Makoto N. Masuno ,  Douglas Cannon ,  Alex B. Wood ,  Marc Foster

IPC: C07C67/31 ,  C07C1/24 ,  C07C51/16 ,  C07C67/03 ,  C07C29/09

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.

Abstract translation: 本文提供了利用聚羟基链烷酸酯（PHA）作为底物进一步转化成C4和C5化合物的方法。 聚羟基链烷酸酯可以进行酯化以得到烷基羟基链烷酸酯和烷基链烯酸酯，其可用作生产烷二烯和烯二酸的有用前体，包括例如丁二烯和丁烯二酸。

公开(公告)号：US20140100378A1

公开(公告)日：2014-04-10

申请号：US14124240

申请日：2012-06-06

Applicant: MICROMIDAS, INC.

Inventor： Makoto N. Masuno ,  John Bissell ,  Ryan L. Smith ,  Brian Higgins ,  Alex Benjamin Wood ,  Marc Foster

IPC: 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.

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：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：US09688603B2

公开(公告)日：2017-06-27

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: C07C69/66 ,  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.