Patents Assigned to Avantium Knowledge Centre B.V.
  • Patent number: 11814738
    Abstract: The invention concerns a process for the electrochemical production of formate. The process is performed in an electrochemical cell comprising a cathode compartment containing a cathode, an anode compartment containing a nickel-based anode and an ion exchange membrane separating the anode compartment from the cathode compartment. The process comprises the following steps: (a) feeding an anolyte comprising at least one polyol to the anode compartment; (b) feeding a catholyte comprising CO2 to the cathode compartment; (c) and applying a voltage difference between the cathode and the anode such that at the cathode CO2 is reduced to formate and at the anode the at least one polyol is oxidized to formate.
    Type: Grant
    Filed: January 28, 2021
    Date of Patent: November 14, 2023
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Bart Van Den Bosch, Marta Catarina Costa Figueiredo, Klaas Jan Pieter Schouten, Marie Brands, Brian James Rawls, Matthew Francis Philips
  • Patent number: 11548980
    Abstract: A polyester copolymer, having a number average molecular weight of equal to or more than 4000 gram/mole and having a glass transition temperature of less than 140° C., containing: (a) in the range from equal to or more than 45 mole % to equal to or less than 50 mole % of one or more bicyclic diol monomer units derived from the group consisting of isosorbide, isoidide, isomannide, 2,3:4,5-di-O-methylenegalactitol and 2,4:3,5-di-O-methylene-D-mannitol; (b) in the range from equal to or more than 25 mole % to equal to or less than 49.9 mole %, of an oxalate monomer unit; (c) in the range from equal to or more than 0.1 mole % to equal to or less than 25 mole % of one or more linear C3-C12 dicarboxylate monomer units; and (d) optionally equal to or more than 0 mole % to equal to or less than 5 mole % of one or more additional monomer units, the percentages based on the total amount of moles of monomer units within the polyester copolymer.
    Type: Grant
    Filed: May 18, 2018
    Date of Patent: January 10, 2023
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Bing Wang, Gerardus Johannes Maria Gruter
  • Publication number: 20220356134
    Abstract: A process for preparing alkylene glycol from particulate matter comprising hemicellulose, cellulose and lignin, which process comprises the steps of subjecting a reactor comprising such particulate matter to a two-stage hydrolysis in the presence of hydrochloric acid to hydrolase the hemicellulose and cellulose in the particulate matter to saccharides, followed by subjecting the obtained hydrolysates to a catalytic conversion with hydrogen and in the presence of a catalyst system to a product comprising one or more alkylene glycols.
    Type: Application
    Filed: July 13, 2020
    Publication date: November 10, 2022
    Applicant: Avantium Knowledge Centre B.V.
    Inventors: Benjamin McKay, Gerardus Johannes Maria Gruter, Martijn Kersbulck
  • Patent number: 11447836
    Abstract: A process for obtaining aqueous hydrolysates from solid material containing hemicellulose, cellulose and lignin. The process comprises hydrolysing at least part of the hemicellulose of the solid material with a first aqueous hydrochloric acid solution at a concentration of 15-40 wt %, yielding a remaining solid material and an aqueous first hydrolysate product solution. The aqueous first hydrolysate is displaced from the remaining solid material with a non-aqueous displacement fluid having a density of less than 1000 kg/m3. Thereafter, at least part of the cellulose of the remaining solid material is hydrolysed with a second aqueous hydrochloric acid solution at a concentration of 40-51 wt %, yielding a residue and an aqueous second hydrolysate product solution. This process is carried out in vertical cylindrical reactors, and the displacement fluid is supplied to a reactor in a downward fashion.
    Type: Grant
    Filed: January 31, 2019
    Date of Patent: September 20, 2022
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Martijn Kersbulck, Benjamin McKay, Gerardus Johannes Maria Gruter
  • Patent number: 11365455
    Abstract: A process for obtaining aqueous hydrolysates from solid material containing hemicellulose, cellulose and lignin, which process comprises hydrolysing at least part of the hemicellulose of the solid material with a first aqueous hydrochloric acid solution at a concentration of 15-40 wt %, yielding a remaining solid material and an aqueous first hydrolysate product solution. The aqueous first hydrolysate is displaced from the remaining solid material with a non-aqueous displacement fluid. Thereafter, at least part of the cellulose of the remaining solid material is hydrolysed with a second aqueous hydrochloric acid solution at a concentration of 40-51 wt %, yielding a residue and an aqueous second hydrolysate product solution.
    Type: Grant
    Filed: January 31, 2019
    Date of Patent: June 21, 2022
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Martijn Kersbulck, Benjamin McKay, Gerardus Johannes Maria Gruter
  • 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: 11352255
    Abstract: A purified hydrochloric acid composition is prepared from a stream of a contaminated hydrochloric acid composition by a process comprising a distillation treatment, wherein at least a first distillation column is operated at a first pressure and a second distillation column is operated at a second pressure, which second pressure is lower than the first pressure; wherein the contaminated hydrochloric acid composition comprises water, contaminants and hydrochloric acid in a first hydrochloric acid concentration of above the azeotropic composition of hydrochloric acid and water at the first pressure; wherein a part of the stream of the contaminated hydrochloric acid composition is fed into the first distillation column to yield a first bottom product comprising water and hydrochloric acid with a hydrochloric acid concentration below the first hydrochloric acid concentration and a first top product comprising hydrochloric acid in a concentration above the azeotropic hydrochloric acid composition at the first pres
    Type: Grant
    Filed: December 11, 2017
    Date of Patent: June 7, 2022
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Benjamin McKay, Johannes Hendrick Vleeming, Wei Zhao
  • Patent number: 11306179
    Abstract: The present disclosure is a polyester copolymer, having a number average molecular weight of equal to or more than 5000 grams/mole and having a glass transition temperature of less than 160° C., comprising:—in the range from equal to or more than 25.0 mole % to equal to or less than 49.9 mole %, based on the total amount of moles of monomer units within the polyester copolymer, of one or more bicyclic diol monomer units, wherein such one or more bicyclic diol monomer units is/are derived from one or more bicyclic diols chosen from the group consisting of isosorbide, isoidide, isomannide, 2,3:4,5-di-O-methylene-galactitol and 2,4:3,5-di-O-methylene-D-mannitol;—in the range from equal to or more than 45.0 mole % to equal to or less than 50.0 mole %, based on the total amount of moles of monomer units within the polyester copolymer, of an oxalate monomer unit; and/or—in the range from equal to or more than 0.1 mole % to equal to or less than 25.
    Type: Grant
    Filed: May 18, 2018
    Date of Patent: April 19, 2022
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Bing Wang, Gerardus Johannes Maria Gruter
  • Publication number: 20220081731
    Abstract: A process for the conversion of a solid material containing hemicellulose, cellulose and lignin, which process comprises the following steps: (i) hydrolyzing, at a temperature equal to or less than 40° C., preferably equal to or less than 30° C., at least part of the hemicellulose of the solid material by contacting the solid material with a first aqueous hydrochloric acid solution, which first aqueous hydrochloric acid solution has a hydrochloric acid concentration in the range from equal to or more than 15.0 wt. % to less than 40.0 wt. %, based on the weight amount of water and hydrochloric acid in such first aqueous hydrochloric acid solution, yielding a remaining solid material and an aqueous first hydrolysate product solution; (ii) displacing aqueous solution from the remaining solid material with a non-aqueous displacement fluid; (iii) hydrolyzing, at a temperature equal to or less than 40° C., preferably equal to or less than 30° C.
    Type: Application
    Filed: January 31, 2019
    Publication date: March 17, 2022
    Applicant: Avantium Knowledge Centre B.V.
    Inventors: Martijn Kersbulck, Benjamin McKay, Gerardus Johannes Maria Gruter
  • Patent number: 11131028
    Abstract: The present disclosure is a method and system for the reduction of carbon dioxide. The method may include receiving hydrogen gas at an anolyte region of an electrochemical cell including an anode, the anode including a gas diffusion electrode, receiving an anolyte feed at an anolyte region of the electrochemical cell, and receiving a catholyte feed including carbon dioxide and an alkali metal bicarbonate at a catholyte region of the electrochemical cell including a cathode. The method may include applying an electrical potential between the anode and cathode sufficient to reduce the carbon dioxide to at least one reduction product.
    Type: Grant
    Filed: May 1, 2019
    Date of Patent: September 28, 2021
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Jerry J. Kaczur, Prasad Lakkaraju, Kyle Teamey
  • Publication number: 20210238699
    Abstract: A process for the conversion of a solid material containing hemicellulose, cellulose and lignin, which process comprises the following steps: (i) hydrolyzing, at a temperature equal to or less than 40° C., preferably equal to or less than 30° C., at least part of the hemicellulose of the solid material by contacting the solid material with a first aqueous hydrochloric acid solution, which first aqueous hydrochloric acid solution has a hydrochloric acid concentration in the range from equal to or more than 15.0 wt. % to less than 40.0 wt. %, based on the weight amount of water and hydrochloric acid in such first aqueous hydrochloric acid solution, yielding a remaining solid material and an aqueous first hydrolysate product solution; (ii) displacing aqueous solution from the remaining solid material with a non-aqueous displacement fluid; (iii) hydrolyzing, at a temperature equal to or less than 40° C., preferably equal to or less than 30° C.
    Type: Application
    Filed: January 31, 2019
    Publication date: August 5, 2021
    Applicant: Avantium Knowledge Centre B.V.
    Inventors: Martijn Kersbulck, Benjamin McKay, Gerardus Johannes Maria Gruter
  • 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: 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
  • Publication number: 20210207231
    Abstract: A process for the conversion of a solid material containing hemicellulose, cellulose and lignin, which process comprises the following steps: (i) hydrolyzing, at a temperature equal to or less than 40° C., preferably equal to or less than 30° C., at least part of the hemicellulose of the solid material by contacting the solid material with a first aqueous hydrochloric acid solution, which first aqueous hydrochloric acid solution has a hydrochloric acid concentration in the range from equal to or more than 15.0 wt. % to less than 40.0 wt. %, based on the weight amount of water and hydrochloric acid in such first aqueous hydrochloric acid solution, yielding a remaining solid material and an aqueous first hydrolysate product solution; (ii) displacing aqueous solution from the remaining solid material with a non-aqueous displacement fluid; (iii) hydrolyzing, at a temperature equal to or less than 40° C., preferably equal to or less than 30° C.
    Type: Application
    Filed: January 31, 2019
    Publication date: July 8, 2021
    Applicant: Avantium Knowledge Centre B.V.
    Inventors: Martijn Kersbulck, Benjamin McKay, Gerardus Johannes Maria Gruter
  • 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
  • Patent number: 10787750
    Abstract: A method reducing carbon dioxide to one or more organic products may include steps (A) to (E). Step (A) may introduce an anolyte to a first compartment of an electrochemical cell. The first compartment may include an anode. Step (B) may introduce a catholyte and carbon dioxide to a second compartment of the electrochemical cell. Step (C) may oxidize an indium cathode to produce an oxidized indium cathode. Step (D) may introduce the oxidized indium cathode to the second compartment. Step (E) may apply an electrical potential between the anode and the oxidized indium cathode sufficient for the oxidized indium cathode to reduce the carbon dioxide to a reduced product.
    Type: Grant
    Filed: October 5, 2018
    Date of Patent: September 29, 2020
    Assignees: The Trustees of Princeton University, Avantium Knowledge Centre B.V.
    Inventors: Andrew B. Bocarsly, Zachary M. Detweiler
  • 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: 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
  • Patent number: 10435799
    Abstract: A carboxylic acid-containing composition, which composition contains an aldehyde, is purified in a process, which process comprises introducing the carboxylic acid-containing composition and an aqueous electrolyte into an electrolytic cell comprising electrodes; electrochemically oxidizing the aldehyde in the electrolytic cell to obtain an electrochemically oxidized product composition comprising a carboxylic acid derived from the aldehyde; and, optionally, separating carboxylic acid from the electrochemically oxidized product composition.
    Type: Grant
    Filed: May 20, 2016
    Date of Patent: October 8, 2019
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Klaas Jan Pieter Schouten, Jan Cornelis Van Der Waal, Maria Varini, Gerardus Johannes Maria Gruter
  • Patent number: 10370319
    Abstract: Process for the manufacture of an adipic acid product by a reduction of a tetrahydrofuran dicarboxylic acid compound, wherein the tetrahydrofuran dicarboxylic acid compound is contacted with hydrogen iodide at a temperature of at least 100° C. in an inert atmosphere to yield the adipic acid product.
    Type: Grant
    Filed: October 3, 2016
    Date of Patent: August 6, 2019
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Gerardus Johannes Maria Gruter, Jan Cornelis Van Der Waal, Lisette Magnee