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).
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Publication number: 20240391929Abstract: 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: ApplicationFiled: September 26, 2022Publication date: November 28, 2024Inventors: Marc Crockatt, Paul Könst, Jan Cornelis Van Der Waal
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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: 11578046Abstract: 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: GrantFiled: January 31, 2019Date of Patent: February 14, 2023Assignee: Furanix Technologies B.V.Inventors: Robert-Jan van Putten, Benjamin McKay, Gerardus Johannes Maria Gruter, Jan Cornelis van der Waal
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Patent number: 11358129Abstract: 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: GrantFiled: March 14, 2019Date of Patent: June 14, 2022Assignee: Avantium Knowledge Centre B.V.Inventors: Jagdeep Singh, Paula Dekker, Jan Cornelis Van Der Waal, Benjamin McKay
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Patent number: 11332454Abstract: 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: GrantFiled: January 31, 2019Date of Patent: May 17, 2022Assignee: Furanix Technologies B.V.Inventors: Robert-Jan van Putten, Benjamin McKay, Gerardus Johannes Maria Gruter, Jan Cornelis van der Waal
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Patent number: 11059768Abstract: 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: GrantFiled: March 14, 2019Date of Patent: July 13, 2021Assignee: Avantium Knowledge Centre B.V.Inventors: Jan Cornelis Van Der Waal, Paula Dekker, Jagdeep Singh, Benjamin McKay
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Patent number: 11060197Abstract: 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: GrantFiled: November 24, 2017Date of Patent: July 13, 2021Assignee: Avantium Knowledge Centre B.V.Inventors: Klaas Jan Pieter Schouten, Gerardus Johannes Maria Gruter, Jan Cornelis Van Der Waal
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Patent number: 11008269Abstract: 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: GrantFiled: March 14, 2019Date of Patent: May 18, 2021Assignee: Avantium Knowledge Centre B.V.Inventors: Paula Dekker, Jan Cornelis Van Der Waal, Gerardus Johannes Maria Gruter, Jagdeep Singh, Benjamin McKay
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Publication number: 20210040022Abstract: 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: ApplicationFiled: March 14, 2019Publication date: February 11, 2021Inventors: Paula Dekker, Jan Cornelis Van Der Waal, Gerardus Johannes Maria Gruter, Jagdeep Singh, Benjamin McKay
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Publication number: 20210032217Abstract: 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 5Type: ApplicationFiled: January 31, 2019Publication date: February 4, 2021Inventors: Robert-Jan van Putten, Benjamin McKay, Gerardus Johannes Maria Gruter, Jan Cornelis van der Waal
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Publication number: 20210032216Abstract: 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: ApplicationFiled: January 31, 2019Publication date: February 4, 2021Inventors: Robert-Jan van Putten, Benjamin McKay, Gerardus Johannes Maria Gruter, Jan Cornelis van der Waal
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Publication number: 20210002192Abstract: 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: ApplicationFiled: March 14, 2019Publication date: January 7, 2021Inventors: Jan Cornelis Van Der Waal, Paula Dekker, Jagdeep Singh, Benjamin McKay
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Publication number: 20200406237Abstract: 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: ApplicationFiled: March 14, 2019Publication date: December 31, 2020Inventors: Jagdeep Singh, Paula Dekker, Jan Cornelis Van Der Waal, Benjamin McKay
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Patent number: 10858601Abstract: 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: GrantFiled: February 10, 2016Date of Patent: December 8, 2020Inventors: Edserd De Jong, Jan Cornelis Van Der Waal, Michael Dirk Boot
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Patent number: 10787748Abstract: 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: GrantFiled: May 20, 2016Date of Patent: September 29, 2020Assignee: Avantium Knowledge Centre B.V.Inventors: Klaas Jan Pieter Schouten, Jan Cornelis Van Der Waal, Maria Varini, Gerardus Johannes Maria Gruter
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Patent number: 10752747Abstract: 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: GrantFiled: October 26, 2016Date of Patent: August 25, 2020Assignee: Furanix Technologies B.V.Inventors: Alice Cristina Mija, Edserd De Jong, Jan Cornelis Van Der Waal, Gerardus Petrus Maria Van Klink
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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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Patent number: 10550128Abstract: 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: GrantFiled: March 4, 2019Date of Patent: February 4, 2020Assignees: Avantium Knowledge Centre B.V., Stichting Wageningen ResearchInventors: Jan Cornelis Van Der Waal, Edserd De Jong, Jacco Van Haveren, Shanmugam Thiyagarajan
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Publication number: 20190382905Abstract: 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: ApplicationFiled: November 24, 2017Publication date: December 19, 2019Inventors: Klaas Jan Pieter Schouten, Gerardus Johannes Maria Gruter, Jan Cornelis Van Der Waal
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Publication number: 20190352784Abstract: 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: ApplicationFiled: November 24, 2017Publication date: November 21, 2019Inventors: Klaas Jan Pieter Schouten, Gerardus Johannes Maria Gruter, Jan Cornelis van der Waal