Patents by Inventor Jan Cornelis van der Waal

Jan Cornelis van der Waal 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).

  • Publication number: 20240391929
    Abstract: The invention is directed to a hydrogenated Diels-Alder adduct according to formula (I) or a salt thereof wherein X is H or an aliphatic moiety that is optionally substituted with one or more heteroatom-comprising substitutents such as hydroxyl, preferably CH2OH or H, more preferably H; R3 is an aliphatic chain comprising at least 6 consecutive carbon atoms: Q1 and Q2 together or individually comprise one or more carboxylic acid moieties, sulfonic acid moieties, salts thereof and/or combinations thereof. In a further aspect, the invention is directed to intermediate compounds and methods to prepare the hydrogenated Diels-Alder adduct.
    Type: Application
    Filed: September 26, 2022
    Publication date: November 28, 2024
    Inventors: Marc Crockatt, Paul Könst, Jan Cornelis Van Der Waal
  • 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: 11578046
    Abstract: A process includes the following steps: a) converting a solid material containing hemicellulose, cellulose and lignin, by: (i) hydrolyzing at least part of the hemicellulose of the solid material with a first aqueous hydrochloric acid solution, yielding a remaining solid material and a hydrochloric acid-containing, aqueous, first hydrolysate product solution; (ii) hydrolyzing at least part of the cellulose of the remaining solid material with a second aqueous hydrochloric acid solution, yielding a residue and a hydrochloric acid-containing, aqueous, second hydrolysate product solution; (b) forwarding to step (c) a, hydrochloric acid-containing, aqueous intermediate product solution comprising: a part of or the whole of the hydrochloric acid-containing, aqueous first and/or second hydrolysate product solution of step (a); and (c) heating at least part of the hydrochloric acid-containing, aqueous intermediate product solution to yield a product solution containing 5-(chloromethyl)furfural, and extracting the 5-
    Type: Grant
    Filed: January 31, 2019
    Date of Patent: February 14, 2023
    Assignee: Furanix Technologies B.V.
    Inventors: Robert-Jan van Putten, Benjamin McKay, Gerardus Johannes Maria Gruter, Jan Cornelis van der Waal
  • Patent number: 11358129
    Abstract: The invention relates to a process for the production of ethylene glycol including the steps of: (i) reacting, in a reactor, at a temperature in the range from equal to or more than 170° C. to equal to or less than 270° C., at least a portion of a carbohydrate source in the presence of hydrogen, a solvent, a homogeneous catalyst, which homogeneous catalyst contains tungsten, and a heterogeneous catalyst, which heterogeneous catalyst contains one or more transition metals from groups 8, 9 and 10 of the Periodic Table of the Elements, yielding ethylene glycol and a spent heterogeneous catalyst; (ii) regenerating the spent heterogeneous catalyst by removing at least a portion of deposited tungsten species from the spent heterogeneous catalyst, yielding a regenerated heterogeneous catalyst; and (iii) using at least a portion of the regenerated heterogeneous catalyst as heterogeneous catalyst in the reaction of step (i).
    Type: Grant
    Filed: March 14, 2019
    Date of Patent: June 14, 2022
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Jagdeep Singh, Paula Dekker, Jan Cornelis Van Der Waal, Benjamin McKay
  • Patent number: 11332454
    Abstract: A process for the conversion of solid lignocellulosic material containing hemicellulose, cellulose and lignin, includes (a) hydrolyzing, at a temperature equal to or less than 40° C. at least part of the hemicellulose and at least part of the cellulose of the solid lignocellulosic material with an aqueous hydrochloric acid solution, containing in the range from equal to or more than 40.0 wt. % to equal to or less than 51.0 wt. % hydrochloric acid, based on the combined weight amount of water and hydrochloric acid in the aqueous hydrochloric acid solution; yielding a hydrochloric acid-containing, aqueous hydrolysate solution; (b) separating the hydrochloric acid-containing, aqueous hydrolysate solution from the lignin; and (c) heating at least part of the hydrochloric acid-containing, aqueous hydrolysate solution to a temperature equal to or more than 60° C.
    Type: Grant
    Filed: January 31, 2019
    Date of Patent: May 17, 2022
    Assignee: Furanix Technologies B.V.
    Inventors: Robert-Jan van Putten, Benjamin McKay, Gerardus Johannes Maria Gruter, Jan Cornelis van der Waal
  • Patent number: 11059768
    Abstract: A continuous or semi-continuous process for the preparation of ethylene glycol from a carbohydrate source including: reacting, in a reactor, at a temperature in the range from equal to or more than 170° C. to equal to or less than 270° C., at least a portion of a carbohydrate source in the presence of hydrogen, a solvent, and a catalyst system, to yield ethylene glycol; wherein the catalyst system includes: a homogeneous catalyst, which homogeneous catalyst contains tungsten; and a heterogeneous catalyst, which heterogeneous catalyst contains one or more transition metals from groups 8, 9 and 10 of the Periodic Table of the Elements supported on a carrier; and wherein continuously or periodically additional heterogeneous catalyst is added to the reactor. Further described is a catalyst system that can be used in such a process.
    Type: Grant
    Filed: March 14, 2019
    Date of Patent: July 13, 2021
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Jan Cornelis Van Der Waal, Paula Dekker, Jagdeep Singh, Benjamin McKay
  • Patent number: 11060197
    Abstract: A process for treating a dicarboxylic acid composition, with the proviso that the dicarboxylic acid is not furan 2,5-dicarboxylic acid, which process comprises: —introducing a dicarboxylic acid composition, which dicarboxylic acid composition contains an impurity compound and which impurity compound is an organic compound comprising a carbonyl group, into a cathode compartment of an electrochemical cell; and electrochemically reducing the impurity compound in the cathode compartment.
    Type: Grant
    Filed: November 24, 2017
    Date of Patent: July 13, 2021
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Klaas Jan Pieter Schouten, Gerardus Johannes Maria Gruter, Jan Cornelis Van Der Waal
  • Patent number: 11008269
    Abstract: A process for the production of ethylene glycol including the steps of: (i) providing, to a first reactor, a carbohydrate source, a solvent, hydrogen, a first heterogeneous catalyst, which first heterogeneous catalyst contains one or more transition metals from groups 8, 9 and 10 of the Periodic Table of the Elements, and a homogeneous catalyst, which homogeneous catalyst contains tungsten; (ii) reacting, in the first reactor, at a temperature in the range from equal to or more than 170° C. to equal to or less than 270° C.
    Type: Grant
    Filed: March 14, 2019
    Date of Patent: May 18, 2021
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Paula Dekker, Jan Cornelis Van Der Waal, Gerardus Johannes Maria Gruter, Jagdeep Singh, Benjamin McKay
  • Publication number: 20210040022
    Abstract: A process for the production of ethylene glycol including the steps of: (i) providing, to a first reactor, a carbohydrate source, a solvent, hydrogen, a first heterogeneous catalyst, which first heterogeneous catalyst contains one or more transition metals from groups 8, 9 and 10 of the Periodic Table of the Elements, and a homogeneous catalyst, which homogeneous catalyst contains tungsten; (ii) reacting, in the first reactor, at a temperature in the range from equal to or more than 170° C. to equal to or less than 270° C.
    Type: Application
    Filed: March 14, 2019
    Publication date: February 11, 2021
    Inventors: Paula Dekker, Jan Cornelis Van Der Waal, Gerardus Johannes Maria Gruter, Jagdeep Singh, Benjamin McKay
  • Publication number: 20210032217
    Abstract: A process includes the following steps: a) converting a solid material containing hemicellulose, cellulose and lignin, by: (i) hydrolyzing at least part of the hemicellulose of the solid material with a first aqueous hydrochloric acid solution, yielding a remaining solid material and a hydrochloric acid- containing, aqueous, first hydrolysate product solution; (ii) hydrolyzing at least part of the cellulose of the remaining solid material with a second aqueous hydrochloric acid solution, yielding a residue and a hydrochloric acid-containing, aqueous, second hydrolysate product solution; (b) forwarding to step (c) a, hydrochloric acid-containing, aqueous intermediate product solution comprising: a part of or the whole of the hydrochloric acid-containing, aqueous first and/or second hydrolysate product solution of step (a); and (c) heating at least part of the hydrochloric acid-containing, aqueous intermediate product solution to yield a product solution containing 5-(chloromethyl)furfural, and extracting the 5
    Type: Application
    Filed: January 31, 2019
    Publication date: February 4, 2021
    Inventors: Robert-Jan van Putten, Benjamin McKay, Gerardus Johannes Maria Gruter, Jan Cornelis van der Waal
  • Publication number: 20210032216
    Abstract: A process for the conversion of solid lignocellulosic material containing hemicellulose, cellulose and lignin, includes (a) hydrolyzing, at a temperature equal to or less than 40° C. at least part of the hemicellulose and at least part of the cellulose of the solid lignocellulosic material with an aqueous hydrochloric acid solution, containing in the range from equal to or more than 40.0 wt. % to equal to or less than 51.0 wt. % hydrochloric acid, based on the combined weight amount of water and hydrochloric acid in the aqueous hydrochloric acid solution; yielding a hydrochloric acid-containing, aqueous hydrolysate solution; (b) separating the hydrochloric acid-containing, aqueous hydrolysate solution from the lignin; and (c) heating at least part of the hydrochloric acid-containing, aqueous hydrolysate solution to a temperature equal to or more than 60° C.
    Type: Application
    Filed: January 31, 2019
    Publication date: February 4, 2021
    Inventors: Robert-Jan van Putten, Benjamin McKay, Gerardus Johannes Maria Gruter, Jan Cornelis van der Waal
  • Publication number: 20210002192
    Abstract: A continuous or semi-continuous process for the preparation of ethylene glycol from a carbohydrate source including: reacting, in a reactor, at a temperature in the range from equal to or more than 170° C. to equal to or less than 270° C., at least a portion of a carbohydrate source in the presence of hydrogen, a solvent, and a catalyst system, to yield ethylene glycol; wherein the catalyst system includes: a homogeneous catalyst, which homogeneous catalyst contains tungsten; and a heterogeneous catalyst, which heterogeneous catalyst contains one or more transition metals from groups 8, 9 and 10 of the Periodic Table of the Elements supported on a carrier; and wherein continuously or periodically additional heterogeneous catalyst is added to the reactor. Further described is a catalyst system that can be used in such a process.
    Type: Application
    Filed: March 14, 2019
    Publication date: January 7, 2021
    Inventors: Jan Cornelis Van Der Waal, Paula Dekker, Jagdeep Singh, Benjamin McKay
  • Publication number: 20200406237
    Abstract: The invention relates to a process for the production of ethylene glycol including the steps of: (i) reacting, in a reactor, at a temperature in the range from equal to or more than 170° C. to equal to or less than 270° C., at least a portion of a carbohydrate source in the presence of hydrogen, a solvent, a homogeneous catalyst, which homogeneous catalyst contains tungsten, and a heterogeneous catalyst, which heterogeneous catalyst contains one or more transition metals from groups 8, 9 and 10 of the Periodic Table of the Elements, yielding ethylene glycol and a spent heterogeneous catalyst; (ii) regenerating the spent heterogeneous catalyst by removing at least a portion of deposited tungsten species from the spent heterogeneous catalyst, yielding a regenerated heterogeneous catalyst; and (iii) using at least a portion of the regenerated heterogeneous catalyst as heterogeneous catalyst in the reaction of step (i).
    Type: Application
    Filed: March 14, 2019
    Publication date: December 31, 2020
    Inventors: Jagdeep Singh, Paula Dekker, Jan Cornelis Van Der Waal, Benjamin McKay
  • Patent number: 10858601
    Abstract: A fuel composition comprises humins and at least one organic oxygenated solvent which has an apparent viscosity of at most 1.5 Pa·s at 100° C. at a shear rate of 30 s?1. Humins are produced by the dehydration of carbohydrates. The organic oxygenated solvent is selected from the group consisting of alcohols, ethers, aldehydes, ketones, acids, esters, which may be aromatic, cycloaliphatic and aliphatic, and mixtures thereof. The fuel compositions can be used as marine fuel.
    Type: Grant
    Filed: February 10, 2016
    Date of Patent: December 8, 2020
    Inventors: Edserd De Jong, Jan Cornelis Van Der Waal, Michael Dirk Boot
  • Patent number: 10787748
    Abstract: An aromatic dicarboxylic acid of chemical formula HOOC—Ar1—COOH is prepared in a process wherein a feedstock comprising at least an aromatic aldehyde compound of chemical formula (1): OHC—Ar1—COOH, wherein Ar1 represents an arylene or heteroarylene moiety, and an aqueous electrolyte are provided; the feedstock and the aqueous electrolyte are introduced into an electrolytic cell comprising electrodes, wherein at least one of the electrodes comprises a non-noble metal and/or an oxide and/or a hydroxide thereof and/or carbon; and the aromatic aldehyde compound of formula (1) is oxidized electrochemically to yield the aromatic dicarboxylic acid.
    Type: Grant
    Filed: May 20, 2016
    Date of Patent: September 29, 2020
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Klaas Jan Pieter Schouten, Jan Cornelis Van Der Waal, Maria Varini, Gerardus Johannes Maria Gruter
  • Patent number: 10752747
    Abstract: A foam includes a cellular structure and having a density of at most 0.50 g/cm3, where the cellular structure is provided by a solid material that includes humins. Such a foam is prepared in a process, which includes: providing a starting material containing humins; and heating the starting material to a temperature in the range of 150 to 450° C. The foam can be used in articles for a variety of applications such as substrate for plant growth, as adsorbent for treating waste water or waste gases, as support for solid catalysts, as insulation material, or packaging material.
    Type: Grant
    Filed: October 26, 2016
    Date of Patent: August 25, 2020
    Assignee: Furanix Technologies B.V.
    Inventors: Alice Cristina Mija, Edserd De Jong, Jan Cornelis Van Der Waal, Gerardus Petrus Maria Van Klink
  • 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
  • Patent number: 10550128
    Abstract: A hydrogenated Diels-Alder adduct of the formula (III) a hydrogenated Diels-Alder adduct of the formula (IV) and a lactone compound of formula (V) are disclosed and described.
    Type: Grant
    Filed: March 4, 2019
    Date of Patent: February 4, 2020
    Assignees: Avantium Knowledge Centre B.V., Stichting Wageningen Research
    Inventors: Jan Cornelis Van Der Waal, Edserd De Jong, Jacco Van Haveren, Shanmugam Thiyagarajan
  • Publication number: 20190382905
    Abstract: A process for treating a dicarboxylic acid composition, with the proviso that the dicarboxylic acid is not furan 2,5-dicarboxylic acid, which process comprises: —introducing a dicarboxylic acid composition, which dicarboxylic acid composition contains an impurity compound and which impurity compound is an organic compound comprising a carbonyl group, into a cathode compartment of an electrochemical cell; and electrochemically reducing the impurity compound in the cathode compartment.
    Type: Application
    Filed: November 24, 2017
    Publication date: December 19, 2019
    Inventors: Klaas Jan Pieter Schouten, Gerardus Johannes Maria Gruter, Jan Cornelis Van Der Waal
  • Publication number: 20190352784
    Abstract: A process for treating a furan-2,5-dicarboxylic acid composition, which process comprises: introducing a furan-2,5-di-carboxylic acid composition, which furan-2,5-dicarboxylic acid composition contains an impurity compound and which impurity compound is 5-formyl-furan-2-carboxylic acid, into a cathode compartment of an electrochemical cell; and electrochemically reducing the impurity compound in the cathode compartment.
    Type: Application
    Filed: November 24, 2017
    Publication date: November 21, 2019
    Inventors: Klaas Jan Pieter Schouten, Gerardus Johannes Maria Gruter, Jan Cornelis van der Waal