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).

  • Patent number: 11932616
    Abstract: 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: Grant
    Filed: April 30, 2019
    Date of Patent: March 19, 2024
    Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
    Inventors: Marc Crockatt, Johan Urbanus
  • Publication number: 20240067593
    Abstract: 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: Application
    Filed: October 22, 2020
    Publication date: February 29, 2024
    Applicant: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
    Inventor: Marc CROCKATT
  • Patent number: 11912656
    Abstract: 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: Grant
    Filed: December 20, 2019
    Date of Patent: February 27, 2024
    Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
    Inventors: Marc Crockatt, Roman Latsuzbaia, Johan Urbanus, Earl Lawrence Vincent Goetheer, Richard Antonius Van Heck
  • Patent number: 11725014
    Abstract: 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: Grant
    Filed: October 3, 2018
    Date of Patent: August 15, 2023
    Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
    Inventors: Marc Crockatt, Leonard Ferdinand Gerard Geers, Johan Urbanus, Rudolf Gijsbertus Van Someren, Jan Cornelis Van Der Waal
  • Patent number: 11603361
    Abstract: 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: Grant
    Filed: September 30, 2019
    Date of Patent: March 14, 2023
    Assignee: Nederlandse Organisatie voor toegepastnatuurwetens
    Inventors: Marc Crockatt, Carol Andrea Roa Engel, Cornelis Petrus Marcus Roelands, Johannes Van Der Meer
  • Publication number: 20220363624
    Abstract: 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: Application
    Filed: October 5, 2020
    Publication date: November 17, 2022
    Applicant: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
    Inventors: Marc CROCKATT, Jan Comelis VAN DER WAAL, Johan URBANUS
  • Patent number: 11384095
    Abstract: 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: Grant
    Filed: August 29, 2019
    Date of Patent: July 12, 2022
    Assignee: Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek TNO
    Inventors: Marc Crockatt, Johan Urbanus, Pieter Cornelis Antonius Bruijnincx, Christopher Stuart Lancefield, Bart Fölker
  • Publication number: 20220090274
    Abstract: 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: Application
    Filed: December 20, 2019
    Publication date: March 24, 2022
    Inventors: Marc Crockatt, Roman Latsuzbaia, Johan Urbanus, Earl Lawrence Vincent Goetheer, Richard Antonius Van Heck
  • Patent number: 11267796
    Abstract: 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: Grant
    Filed: February 28, 2018
    Date of Patent: March 8, 2022
    Assignee: Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek TNO
    Inventors: Marc Crockatt, Roel Johannes Martinus Bisselink, Roman Latsuzbaia, Cornelis Petrus Marcus Roelands, Earl Lawrence Vincent Goetheer
  • Publication number: 20220064097
    Abstract: 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: Application
    Filed: December 20, 2019
    Publication date: March 3, 2022
    Applicant: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
    Inventors: Johan URBANUS, Marc CROCKATT, Earl Lawrence Vincent GOETHEER, Roman LATSUZBAIA
  • Publication number: 20210332021
    Abstract: 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: Application
    Filed: September 30, 2019
    Publication date: October 28, 2021
    Inventors: Marc CROCKATT, Carol Andrea ROA ENGEL, Cornelis Petrus Marcus ROELANDS, Johannes VAN DER MEER
  • Publication number: 20210323973
    Abstract: 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: Application
    Filed: August 29, 2019
    Publication date: October 21, 2021
    Inventors: Marc CROCKATT, Johan URBANUS, Pieter Cornelis Antonius BRUIJNINCX, Christopher Stuart LANCEFIELD, Bart FÖLKER
  • Patent number: 11104656
    Abstract: 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: Grant
    Filed: December 31, 2018
    Date of Patent: August 31, 2021
    Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
    Inventors: Carol Andrea Roa Engel, Johannes Van Der Meer, Leonard Ferdinand Gerard Geers, Marc Crockatt
  • Publication number: 20210115005
    Abstract: 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: Application
    Filed: April 30, 2019
    Publication date: April 22, 2021
    Inventors: Marc CROCKATT, Johan URBANUS
  • Publication number: 20210070722
    Abstract: 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: Application
    Filed: December 31, 2018
    Publication date: March 11, 2021
    Inventors: Carol Andrea Roa Engel, Johannes Van Der Meer, Leonard Ferdinand Gerard Geers, Marc Crockatt
  • Patent number: 10934242
    Abstract: 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: Grant
    Filed: August 17, 2018
    Date of Patent: March 2, 2021
    Assignee: Stichting Wageningen Research
    Inventors: Roel Johannes Martinus Bisselink, Marc Crockatt, Earl Lawrence Vincent Goetheer
  • Publication number: 20200283366
    Abstract: 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: Application
    Filed: August 17, 2018
    Publication date: September 10, 2020
    Applicant: Stichting Wageningen Research
    Inventors: Roel Johannes Martinus BISSELINK, Marc CROCKATT, Earl Lawrence Vincent GOETHEER
  • Publication number: 20200239492
    Abstract: 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: Application
    Filed: October 3, 2018
    Publication date: July 30, 2020
    Inventors: Marc Crockatt, Leonard Ferdinand Gerard Geers, Johan Urbanus, Rudolf Gijsbertus Van Someren, Jan Cornelis Van Der Waal
  • Publication number: 20200055832
    Abstract: 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: Application
    Filed: February 28, 2018
    Publication date: February 20, 2020
    Inventors: Marc CROCKATT, Roel Johannes Martinus BISSELINK, Roman LATSUZBAIA, Cornelis Petrus Marcus ROELANDS, Earl Lawrence Vincent GOETHEER
  • Patent number: 10562875
    Abstract: 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: Grant
    Filed: February 27, 2017
    Date of Patent: February 18, 2020
    Assignee: Nederlandse Organisaite Voor Toegepast-Natuurwetenschappelijk Onderzoek TNO
    Inventors: Marc Crockatt, Jan Harm Urbanus