Patents by Inventor Marc CROCKATT
Marc CROCKATT has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 11932616Abstract: 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.Type: GrantFiled: April 30, 2019Date of Patent: March 19, 2024Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNOInventors: Marc Crockatt, Johan Urbanus
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Publication number: 20240067593Abstract: The invention is directed to a process for the preparation of an aromatic acid or a phenolic compound, said process comprising reacting a dienophile and a furanic compound comprising an acetal moiety in a Diels-Alders reaction to obtain an aromatic compound comprising said acetal moiety, followed by hydrolysis and oxidation of said acetal moiety into a hydroxide or carboxylate moiety to form the aromatic acid or phenolic compound, wherein said dienophile is selected from the group consisting of alkylenes, acetylenes, acrylates, maleates, fumarates, maleimides, propiolates, acetylene dicarboxylates, and benzynes and wherein said acetal moiety is bound directly to the 2-position of the furanic compound.Type: ApplicationFiled: October 22, 2020Publication date: February 29, 2024Applicant: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNOInventor: Marc CROCKATT
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Patent number: 11912656Abstract: 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-?-formylacrylic acid to maleic acid or a derivative thereof by contacting the 5-hydroxy-2(5H)-furanone and/or cis-?-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-?-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.Type: GrantFiled: December 20, 2019Date of Patent: February 27, 2024Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNOInventors: Marc Crockatt, Roman Latsuzbaia, Johan Urbanus, Earl Lawrence Vincent Goetheer, Richard Antonius Van Heck
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Patent number: 11725014Abstract: 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.Type: GrantFiled: October 3, 2018Date of Patent: August 15, 2023Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNOInventors: Marc Crockatt, Leonard Ferdinand Gerard Geers, Johan Urbanus, Rudolf Gijsbertus Van Someren, Jan Cornelis Van Der Waal
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Patent number: 11603361Abstract: 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.Type: GrantFiled: September 30, 2019Date of Patent: March 14, 2023Assignee: Nederlandse Organisatie voor toegepastnatuurwetensInventors: Marc Crockatt, Carol Andrea Roa Engel, Cornelis Petrus Marcus Roelands, Johannes Van Der Meer
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Publication number: 20220363624Abstract: A process for the preparation of an aromatic product is disclosed which includes a step b) of contacting one or more intermediate compounds with a further acid to form the aromatic product. The intermediate compounds can be obtained in step a) that includes contacting a 7-oxabicyclo[2.2.1]hept-2-ene core structure with an acidic mixture. The amount of acid in step b) is higher than the amount of acid in step a).Type: ApplicationFiled: October 5, 2020Publication date: November 17, 2022Applicant: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNOInventors: Marc CROCKATT, Jan Comelis VAN DER WAAL, Johan URBANUS
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Patent number: 11384095Abstract: 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 ?,?-unsaturated carbonyl comprising an ??-leaving group. The inventions further involved preparation of phthalic anhydride compounds, phthalic acid compounds and reduction products of the intermediate phthalide compounds.Type: GrantFiled: August 29, 2019Date of Patent: July 12, 2022Assignee: Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek TNOInventors: Marc Crockatt, Johan Urbanus, Pieter Cornelis Antonius Bruijnincx, Christopher Stuart Lancefield, Bart Fölker
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Publication number: 20220090274Abstract: 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-?-formylacrylic acid to maleic acid or a derivative thereof by contacting 5-hydroxy-2(5H)-furanone and/or cis-?-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-?-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.Type: ApplicationFiled: December 20, 2019Publication date: March 24, 2022Inventors: Marc Crockatt, Roman Latsuzbaia, Johan Urbanus, Earl Lawrence Vincent Goetheer, Richard Antonius Van Heck
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Patent number: 11267796Abstract: The invention is directed to the to the electrochemical preparation of 2,5-furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF) by electrochemical oxidation, comprising a first oxidation step of oxidizing HMF to 5-hydroxymethyl-2-furan-carboxylic acid (HMFCA) in an electrochemical cell, subsequently a first isolation step of isolating HMFCA, followed by a second oxidation step of HMFCA to FDCA.Type: GrantFiled: February 28, 2018Date of Patent: March 8, 2022Assignee: Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek TNOInventors: Marc Crockatt, Roel Johannes Martinus Bisselink, Roman Latsuzbaia, Cornelis Petrus Marcus Roelands, Earl Lawrence Vincent Goetheer
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Publication number: 20220064097Abstract: The invention is directed to a process for the preparation of maleic acid or a derivative thereof. Said process comprising an electrochemical oxidation of a furoic acid compound into maleic acid in an electrolyte solution; and optionally further comprising a step of reacting the maleic acid to the derivative thereof. In an alternative embodiment, said process comprising a first step comprising an electrochemical oxidation in an electrolyte solution of a furanic compound into one or more intermediates; followed by a second step comprising a chemo-catalytic oxidation of said intermediates to provide maleic acid or a derivative thereof.Type: ApplicationFiled: December 20, 2019Publication date: March 3, 2022Applicant: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNOInventors: Johan URBANUS, Marc CROCKATT, Earl Lawrence Vincent GOETHEER, Roman LATSUZBAIA
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Publication number: 20210332021Abstract: 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.Type: ApplicationFiled: September 30, 2019Publication date: October 28, 2021Inventors: Marc CROCKATT, Carol Andrea ROA ENGEL, Cornelis Petrus Marcus ROELANDS, Johannes VAN DER MEER
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Publication number: 20210323973Abstract: 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 ?,?-unsaturated carbonyl comprising an ??-leaving group. The inventions further involved preparation of phthalic anhydride compounds, phthalic acid compounds and reduction products of the intermediate phthalide compounds.Type: ApplicationFiled: August 29, 2019Publication date: October 21, 2021Inventors: Marc CROCKATT, Johan URBANUS, Pieter Cornelis Antonius BRUIJNINCX, Christopher Stuart LANCEFIELD, Bart FÖLKER
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Patent number: 11104656Abstract: 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.Type: GrantFiled: December 31, 2018Date of Patent: August 31, 2021Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNOInventors: Carol Andrea Roa Engel, Johannes Van Der Meer, Leonard Ferdinand Gerard Geers, Marc Crockatt
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Publication number: 20210115005Abstract: 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.Type: ApplicationFiled: April 30, 2019Publication date: April 22, 2021Inventors: Marc CROCKATT, Johan URBANUS
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Publication number: 20210070722Abstract: 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.Type: ApplicationFiled: December 31, 2018Publication date: March 11, 2021Inventors: Carol Andrea Roa Engel, Johannes Van Der Meer, Leonard Ferdinand Gerard Geers, Marc Crockatt
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Patent number: 10934242Abstract: The invention is directed to a method of electrochemically producing valeric acid. The method of the invention comprises contacting a solution of levulinic acid with an anode and a cathode in an electrochemical cell; and electrochemically reducing levulinic acid at the cathode to form valeric acid, wherein the cathode comprises one or more materials selected from the group consisting of cadmium, zinc, and indium.Type: GrantFiled: August 17, 2018Date of Patent: March 2, 2021Assignee: Stichting Wageningen ResearchInventors: Roel Johannes Martinus Bisselink, Marc Crockatt, Earl Lawrence Vincent Goetheer
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Publication number: 20200283366Abstract: The invention is directed to a method of electrochemically producing valeric acid. The method of the invention comprises contacting a solution of levulinic acid with an anode and a cathode in an electrochemical cell; and electrochemically reducing levulinic acid at the cathode to form valeric acid, wherein the cathode comprises one or more materials selected from the group consisting of cadmium, zinc, and indium.Type: ApplicationFiled: August 17, 2018Publication date: September 10, 2020Applicant: Stichting Wageningen ResearchInventors: Roel Johannes Martinus BISSELINK, Marc CROCKATT, Earl Lawrence Vincent GOETHEER
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Publication number: 20200239492Abstract: 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.Type: ApplicationFiled: October 3, 2018Publication date: July 30, 2020Inventors: Marc Crockatt, Leonard Ferdinand Gerard Geers, Johan Urbanus, Rudolf Gijsbertus Van Someren, Jan Cornelis Van Der Waal
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Publication number: 20200055832Abstract: The invention is directed to the to the electrochemical preparation of 2,5- furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF) by electrochemical oxidation, comprising a first oxidation step of oxidizing HMF to 5-hydroxymethyl-2-furan-carboxylic acid (HMFCA) in an electrochemical cell, subsequently a first isolation step of isolating HMFCA, followed by a second oxidation step of HMFCA to FDCA.Type: ApplicationFiled: February 28, 2018Publication date: February 20, 2020Inventors: Marc CROCKATT, Roel Johannes Martinus BISSELINK, Roman LATSUZBAIA, Cornelis Petrus Marcus ROELANDS, Earl Lawrence Vincent GOETHEER
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Patent number: 10562875Abstract: 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.Type: GrantFiled: February 27, 2017Date of Patent: February 18, 2020Assignee: Nederlandse Organisaite Voor Toegepast-Natuurwetenschappelijk Onderzoek TNOInventors: Marc Crockatt, Jan Harm Urbanus