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：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：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：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：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：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。