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公开(公告)号：US11725014B2
公开(公告)日：2023-08-15
申请号：US16753048
申请日：2018-10-03
发明人： Marc Crockatt , Leonard Ferdinand Gerard Geers , Johan Urbanus , Rudolf Gijsbertus Van Someren , Jan Cornelis Van Der Waal
IPC分类号： B01J19/06 , B01J19/00 , B01J14/00 , C07D493/18 , B01J4/00
CPC分类号： C07D493/18 , B01J4/001 , B01J14/00 , B01J19/0013 , B01J19/06 , B01J2219/00033 , B01J2219/00119
摘要： The invention is directed to a process for the continuous preparation of a cycloadduct product from the reaction of a furanic with a dienophile, comprising heating a first liquid feed stream comprising the dienophile and a solvent in which the dienophile is dissolved; providing a second liquid feed stream comprising the furanic; leading the first liquid feed stream and the second liquid feed stream into a continuous reactor to produce a product solution stream comprising the cycloadduct product; and leading the product solution stream to an product isolation zone to produce an isolated cycloadduct product. A further aspect of the invention is an apparatus for carrying out this reaction.
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公开(公告)号：US11912656B2
公开(公告)日：2024-02-27
申请号：US17414419
申请日：2019-12-20
发明人： Marc Crockatt , Roman Latsuzbaia , Johan Urbanus , Earl Lawrence Vincent Goetheer , Richard Antonius Van Heck
IPC分类号： C07C51/21 , C07C51/29 , C07C51/305 , C25B3/07 , C25B3/23 , C07C51/235 , C25B11/04 , C25B11/052 , C25B11/042
CPC分类号： C07C51/235 , C25B3/07 , C25B3/23 , C25B11/04 , C25B11/042 , C25B11/052
摘要： The invention is directed to a process for preparing maleic acid or a derivative thereof, the process comprising a step b) of oxidizing 5-hydroxy-2(5H)-furanone and/or cis-β-formylacrylic acid to maleic acid or a derivative thereof by contacting the 5-hydroxy-2(5H)-furanone and/or cis-β-formylacrylic acid with molecular oxygen (O2) in the presence of a catalyst. In a particular embodiment, the step b) is preceded by a step a) of oxidizing a furanic compound according to formula I into the 5-hydroxy-2(5H)-furanone and/or cis-β-formylacrylic acid,
wherein R1 is H, CH2OH, CO2H or CHO and R2 is H, OH, C1-C6 alkyl or O(C1-C6 alkyl), or esters, ethers, amides, acid halides, anhydrides, carboximidates, nitriles, and salts of formula I.-
公开(公告)号：US11104656B2
公开(公告)日：2021-08-31
申请号：US16958255
申请日：2018-12-31
发明人： Carol Andrea Roa Engel , Johannes Van Der Meer , Leonard Ferdinand Gerard Geers , Marc Crockatt
IPC分类号： C07D307/68
摘要： The invention is based on the finding that when conducting crystallization of FDCA at high temperatures, the formation of significant amounts of colored byproduct can be reduced or even avoided when the FDCA mixture is kept at temperatures above 100° C. for less than 15 minutes. This is achieved by conducting the crystallization process in a continuous reactor. Accordingly, the method comprises the steps of feeding a mixture comprising undissolved FDCA and a solvent to a reactor; and dissolving FDCA by superheating the mixture in the reactor to a temperature of at least 130° C.; and crystallizing FDCA by cooling the mixture in the reactor, wherein the reactor is a continuous reactor and the residence time in the reactor zone wherein the FDCA mixture has a temperature above 100° C. is less than 15 minutes.
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公开(公告)号：US10562875B2
公开(公告)日：2020-02-18
申请号：US16079751
申请日：2017-02-27
发明人： Marc Crockatt , Jan Harm Urbanus
IPC分类号： C07D307/89 , C07C37/56 , C07C45/51 , C07C249/12 , C07C249/16 , C07C51/27 , C07D307/52 , C07C39/04 , C07C47/54 , C07C63/307 , C07C251/48 , C07C251/86 , C07B37/12
摘要： Described are methods for preparing phenols, benzene carboxylic acids, esters and anhydrides thereof from furanic compounds by reaction with a dienophile, wherein the furanic compounds are reacted with a hydrazine and/or oxime and then reacted with a dienophile.
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公开(公告)号：US11932616B2
公开(公告)日：2024-03-19
申请号：US17047573
申请日：2019-04-30
发明人： Marc Crockatt , Johan Urbanus
IPC分类号： C07D307/89 , C07C51/087 , C07C67/30 , C07C253/30 , C07D209/48 , C07D307/88
CPC分类号： C07D307/89 , C07C51/087 , C07C67/30 , C07C253/30 , C07D209/48 , C07D307/88
摘要： The invention is directed to a process for the ring-opening of a cycloadduct obtainable from a reaction of a furanic compound and a diene, said process comprising contacting the cycloadduct with an acidic mixture comprising sulfuric acid and an activating agent to obtain a ring-opened product. The present invention is particularly directed a continuous process.
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公开(公告)号：US11384095B2
公开(公告)日：2022-07-12
申请号：US17271947
申请日：2019-08-29
发明人： Marc Crockatt , Johan Urbanus , Pieter Cornelis Antonius Bruijnincx , Christopher Stuart Lancefield , Bart Fölker
IPC分类号： C07D493/18 , C07D307/89 , C07D307/88
摘要： The present invention is directed to the preparation of phthalic anhydride compounds and the intermediate phthalide compounds. In particular, the invention is directed to an improved bio-based route from furanic compounds to phthalic anhydride compounds by reacting furfuryl alcohol (i.e. 2-hydroxymethylfuran) or an analogue thereof having a nucleophilic atom on the 2-methyl, with a dienophile comprising an α,β-unsaturated carbonyl comprising an α′-leaving group. The inventions further involved preparation of phthalic anhydride compounds, phthalic acid compounds and reduction products of the intermediate phthalide compounds.
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公开(公告)号：US20220090274A1
公开(公告)日：2022-03-24
申请号：US17414419
申请日：2019-12-20
发明人： Marc Crockatt , Roman Latsuzbaia , Johan Urbanus , Earl Lawrence Vincent Goetheer , Richard Antonius Van Heck
IPC分类号： C25B3/07 , C25B3/23 , C25B11/042 , C25B11/052
摘要： The invention is directed to a process for preparing maleic acid or a derivative thereof, said process comprising a step b) of oxidizing 5-hydroxy-2(5H)-furanone and/or cis-β-formylacrylic acid to maleic acid or a derivative thereof by contacting 5-hydroxy-2(5H)-furanone and/or cis-β-formylacrylic acid with molecular oxygen (O2) in the presence of a catalyst. In a particular embodiment, step b) is preceded by a step a) of oxidizing a furanic compound according to formula I into 5-hydroxy-2(5H)-furanone and/or cis-β-formylacrylic acid, wherein R1 is H, CH2OH, CO2H or CHO and R2 is H, OH, C1-C6 alkyl or O(C1-C6 alkyl), or esters, ethers, amides, acid halides, anhydrides, carboximidates, nitriles, and salts thereof.
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公开(公告)号：US20200239492A1
公开(公告)日：2020-07-30
申请号：US16753048
申请日：2018-10-03
发明人： Marc Crockatt , Leonard Ferdinand Gerard Geers , Johan Urbanus , Rudolf Gijsbertus Van Someren , Jan Cornelis Van Der Waal
IPC分类号： C07D493/18 , B01J14/00 , B01J4/00 , B01J19/00 , B01J19/06
摘要： The invention is directed to a process for the continuous preparation of a cycloadduct product from the reaction of a furanic with a dienophile, comprising heating a first liquid feed stream comprising the dienophile and a solvent in which the dienophile is dissolved; providing a second liquid feed stream comprising the furanic; leading the first liquid feed stream and the second liquid feed stream into a continuous reactor to produce a product solution stream comprising the cycloadduct product; and leading the product solution stream to an product isolation zone to produce an isolated cycloadduct product. A further aspect of the invention is an apparatus for carrying out this reaction.
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公开(公告)号：US10100025B2
公开(公告)日：2018-10-16
申请号：US15526022
申请日：2015-11-20
发明人： Marc Crockatt , Jan Harm Urbanus , Johannes Wouterus Van Groenestijn , Martijn Constantijn De Koning
IPC分类号： C07D307/36
摘要： The invention relates to obtaining furans from biomass. In particular, the invention relates to obtaining furans from polyols, such as tetrahydroxybutane. In accordance with the invention tetrahydroxybutane is converted to furan in the presence of a catalyst. The tetrahydroxybutane may be dissolved in a solvent such as water.
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公开(公告)号：US11603361B2
公开(公告)日：2023-03-14
申请号：US17274296
申请日：2019-09-30
发明人： Marc Crockatt , Carol Andrea Roa Engel , Cornelis Petrus Marcus Roelands , Johannes Van Der Meer
IPC分类号： C07D307/68
摘要： The invention is directed to a method for the preparation, in particular for the purification of 2,5-furandicarboxylic acid or a salt thereof, comprising crystallization of a 2,5-furandicarboxylic acid mono salt and then crystallizing 2,5-furandicarboxylic diacid from this mono salt. Preferably, the method is at least partially carried out in a continuous or semi-continuous manner, preferably at least partially in one or more continuous mixed-suspension mixed product removal (MSMPR) crystallizers in series.
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