Patents Assigned to Furanix Technologies B.V.
  • Patent number: 9162960
    Abstract: A substituted benzene derivative is prepared in a process, which includes reacting a furan derivative of formula (I): wherein R is an alkyl group, with an olefin of formula (II): R1—CH?CH—R2??(II) wherein R1 and R2 are the same or different and independently are selected from the group consisting of hydrogen, —CN, —CHO and —COOR3, wherein R3 is selected from hydrogen or an alkyl group, or R1 and R2 together form a —C(O)—O—(O)C— group, with the proviso that R1 and R2 are not both hydrogen, to produce a bicyclic ether; and dehydrating the bicyclic ether to obtain a benzene derivative. The benzene derivative thus obtained can suitably be converted to a benzene carboxylic acid compound by oxidation.
    Type: Grant
    Filed: September 28, 2012
    Date of Patent: October 20, 2015
    Assignee: Furanix Technologies B.V.
    Inventors: Matheus Adrianus Dam, Edserd de Jong, Jacco van Haveren, Aliaksei Pukin
  • Patent number: 9145526
    Abstract: A process for the preparation of a ring-hydrogenated alkyl furfuryl ether of the general formula (I) or a mixture of such ethers: (I) R?-TF—CH2-O—R where TF represents a 2,5-disubstituted tetrahydrofuran ring, where each R independently represents a hydrocarbyl group having from 1 to 20 carbon atoms and where each R? independently represents a methyl group, a hydroxymethyl group, the product of an aldol condensation reaction or an alkoxymethyl group of the general formula (II): (II) —CH2-O—R? where each R? independently represents a hydrocarbyl group having from 1 to 20 carbon atoms, the process including the step of reacting a 5-(alkoxymethyl)furfural of the general formula (III) or a 2,5-bis(dialkoxymethyl)furan of the general formula (IV) under hydrogenation conditions: (III) R?—O—CH2-F—CH?O (IV) R?—O—CH2-F—CH2-O—R? to form said ring-hydrogenated alkyl furfuryl ether of the general formula (I) or a mixture of said ethers wherein F represents a 2,5-disubstituted furan ring, and R?, and R? have the definitio
    Type: Grant
    Filed: May 1, 2013
    Date of Patent: September 29, 2015
    Assignee: FURANIX TECHNOLOGIES B.V.
    Inventors: Gerardus Johannes Maria Gruter, Edserd de Jong
  • Patent number: 9090581
    Abstract: A carbohydrate-containing feedstock is converted in a process by contacting the feedstock in a first step with an alcohol in the presence of a first acid catalyst at a temperature below 100° C. to yield an intermediate product, and contacting at least part of the intermediate product in a second step with an alcohol in the presence of a second acid catalyst at a temperature of at least 100° C. Products of such conversion may include hydroxymethylfurfural, hydroxymethylfurfural ethers, levulinic acid, esters thereof and furfural.
    Type: Grant
    Filed: December 28, 2011
    Date of Patent: July 28, 2015
    Assignee: FURANIX TECHNOLOGIES B.V.
    Inventors: Ana Sofia Vagueiro de Sousa Dias, Gerardus Johannes Maria Gruter, Robert-Jan van Putten
  • Patent number: 9073886
    Abstract: A product including a furandicarboxylate compound and diol is obtained from a furandicarboxylate containing polyester in a process, which includes reacting a polymer composition including furandicarboxylate containing polyester with water or an alcohol, such as an alkyl alcohol with from 1 to 12 carbon atoms, in the presence of a base, that is preferably selected from the group consisting of metal hydrides, metal alkoxides, metal carbonates, metal carboxylates, N-heterocyclic carbenes, amidines, guanidines, phosphazenes and mixtures thereof.
    Type: Grant
    Filed: December 29, 2011
    Date of Patent: July 7, 2015
    Assignee: FURANIX TECHNOLOGIES B.V.
    Inventors: Laszlo Sipos, Michael Leroy Olson
  • Patent number: 8877950
    Abstract: Method for the manufacture of 5-hydroxymethylfurfural derivatives by reacting a fructose and/or glucose-containing starting material with an alcohol in the presence of a catalytic or sub-stoichiometric amount of solid (“heterogeneous”) acid catalyst. The catalysts may be employed in a continuous flow fixed bed or catalytic distillation reactor. The ethers can be applied as a fuel or fuel additive.
    Type: Grant
    Filed: December 15, 2010
    Date of Patent: November 4, 2014
    Assignee: Furanix Technologies B.V.
    Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
  • Patent number: 8865921
    Abstract: A method for the preparation of 2,5-furan dicarboxylic acid includes the step of contacting a feed comprising a compound selected from the group consisting of 5-hydroxymethylfurfural (“HMF”), an ester of 5-hydroxymethyl-furfural, 5-methylfurfural, 5-(chloromethyl)furfural, 5-methylfuroic acid, 5-(chloromethyl)furoic acid, 2,5-dimethylfuran and a mixture of two or more of these compounds with an oxidant in the presence of an oxidation catalyst at a temperature higher than 140° C.
    Type: Grant
    Filed: October 6, 2010
    Date of Patent: October 21, 2014
    Assignee: Furanix Technologies B.V.
    Inventors: Cesar Muñoz De Diego, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
  • Publication number: 20140235892
    Abstract: A substituted benzene derivative is prepared in a process, which includes reacting a furan derivative of formula (I): wherein R is an alkyl group, with an olefin of formula (II): R1—CH?CH—R2??(II) wherein R1 and R2 are the same or different and independently are selected from the group consisting of hydrogen, —CN, —CHO and —COOR3, wherein R3 is selected from hydrogen or an alkyl group, or R1 and R2 together form a —C(O)—O—(O)C— group, with the proviso that R1 and R2 are not both hydrogen, to produce a bicyclic ether; and dehydrating the bicyclic ether to obtain a benzene derivative. The benzene derivative thus obtained can suitably be converted to a benzene carboxylic acid compound by oxidation.
    Type: Application
    Filed: September 28, 2012
    Publication date: August 21, 2014
    Applicant: FURANIX TECHNOLOGIES B.V.
    Inventors: Matheus Adrianus Dam, Edserd de Jong, Jacco van Haveren, Alaiksai Pukin
  • Publication number: 20130345453
    Abstract: A product including a furandicarboxylate compound and diol is obtained from a furandicarboxylate containing polyester in a process, which includes reacting a polymer composition including furandicarboxylate containing polyester with water or an alcohol, such as an alkyl alcohol with from 1 to 12 carbon atoms, in the presence of a base, that is preferably selected from the group consisting of metal hydrides, metal alkoxides, metal carbonates, metal carboxylates, N-heterocyclic carbenes, amidines, guanidines, phosphazenes and mixtures thereof.
    Type: Application
    Filed: December 29, 2011
    Publication date: December 26, 2013
    Applicant: FURANIX TECHNOLOGIES B.V.
    Inventors: Laszlo Sipos, Michael Leroy Olson
  • Publication number: 20130324708
    Abstract: A carbohydrate-containing feedstock is converted in a process by contacting the feedstock in a first step with an alcohol in the presence of a first acid catalyst at a temperature below 100° C. to yield an intermediate product, and contacting at least part of the intermediate product in a second step with an alcohol in the presence of a second acid catalyst at a temperature of at least 100° C. Products of such conversion may include hydroxymethylfurfural, hydroxymethylfurfural ethers, levulinic acid, esters thereof and furfural.
    Type: Application
    Filed: December 28, 2011
    Publication date: December 5, 2013
    Applicant: FURANIX TECHNOLOGIES B.V.
    Inventors: Ana Sofia Vagueiro de Sousa Dias, Gerardus Johannes Maria Gruter, Robert-Jan van Putten
  • Publication number: 20130303792
    Abstract: A process for the preparation of a ring-hydrogenated alkyl furfuryl ether of the general formula (I) or a mixture of such ethers: (I) R?-TF—CH2-O—R where TF represents a 2,5-disubstituted tetrahydrofuran ring, where each R independently represents a hydrocarbyl group having from 1 to 20 carbon atoms and where each R? independently represents a methyl group, a hydroxymethyl group, the product of an aldol condensation reaction or an alkoxymethyl group of the general formula (II): (II) —CH2-O—R? where each R? independently represents a hydrocarbyl group having from 1 to 20 carbon atoms, the process including the step of reacting a 5-(alkoxymethyl)furfural of the general formula (III) or a 2,5-bis(dialkoxymethyl)furan of the general formula (IV) under hydrogenation conditions: (III) R??O—CH2-F—CH?O (IV) R?—O—CH2-F—CH2-O—R? to form said ring-hydrogenated alkyl furfuryl ether of the general formula (I) or a mixture of said ethers wherein F represents a 2,5-disubstituted furan ring, and R?, and R? have the definitio
    Type: Application
    Filed: May 1, 2013
    Publication date: November 14, 2013
    Applicant: Furanix Technologies B.V.
    Inventors: Gerardus Johannes Maria Gruter, Edserd de Jong
  • Patent number: 8519167
    Abstract: A method for the preparation of 2,5-furandicarboxylic acid (“FDCA”) and/or an alkyl ester of FDCA includes the step of contacting a feed comprising a starting material selected from 5-alkoxymethylfurfural, 2,5-di(alkoxymethyl)furan and a mixture thereof with an oxidant in the presence of an oxidation catalyst. The feed may also comprise 5-hydroxymethylfurfural as a further starting material.
    Type: Grant
    Filed: October 6, 2010
    Date of Patent: August 27, 2013
    Assignee: Furanix Technologies B.V.
    Inventors: Cesar Muñoz De Diego, Wayne Paul Schammel, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
  • Patent number: 8435313
    Abstract: A fuel composition includes a ring-hydrogenated alkyl furfuryl ether of the general formula (I): R?-TF-CH2-O—R or a mixture of the ethers, where TF represents a 2,5-disubstituted tetrahydrofuran ring, where each R independently represents a hydrocarbyl group having from 1 to 20 carbon atoms and where each R? independently represents a methyl group, a hydroxymethyl group, the product of an aldol condensation reaction or an alkoxymethyl group of the general formula (II): —CH2-O—R?, where each R? independently represents a hydrocarbyl group having from 1 to 20 carbon atoms, in combination with diesel fuels of petroleum origin or diesel fuels of bioorganic origin.
    Type: Grant
    Filed: May 19, 2009
    Date of Patent: May 7, 2013
    Assignee: Furanix Technologies, B.V.
    Inventors: Gerardus Johannes Maria Gruter, Edserd de Jong
  • Patent number: 8338626
    Abstract: Method for the manufacture of 5-alkoxymethylfurfural derivatives by reacting a fructose and/or glucose-containing starting material with an alcohol in the presence of a catalytic or sub-stoechiometric amount of heterogeneous acid catalyst. The catalysts may be employed in a continuous flow fixed bed or catalytic distillation reactor. The ethers can be applied as a fuel or fuel additive.
    Type: Grant
    Filed: December 8, 2011
    Date of Patent: December 25, 2012
    Assignee: Furanix Technologies B.V.
    Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
  • Patent number: 8314260
    Abstract: Accordingly, the current invention provides a method for the manufacture of an ether or ester of 5-hydroxymethyl-furfural by reacting a hexose-containing starting material or HMF with an alcohol or an organic acid dissolved into an ionic liquid, using a metal chloride as catalyst.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: November 20, 2012
    Assignee: Furanix Technologies B.V.
    Inventors: Gerardus Johannes Maria Gruter, Leo Ernest Manzer, Ana Sofia Vagueiro De Sousa Dias, Frits Dautzenberg, Jindra Purmova
  • Publication number: 20120283452
    Abstract: A method for the preparation of 2,5-furandicarboxylic acid (“FDCA”) and/or an alkyl ester of FDCA includes the step of contacting a feed comprising a starting material selected from 5-alkoxymethylfurfural, 2,5-di(alkoxymethyl)furan and a mixture thereof with an oxidant in the presence of an oxidation catalyst. The feed may also comprise 5-hydroxymethylfurfural as a further starting material.
    Type: Application
    Filed: October 6, 2010
    Publication date: November 8, 2012
    Applicant: FURANIX TECHNOLOGIES B.V.
    Inventors: Cesar Muñoz De Diego, Wayne Paul Schammel, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
  • Publication number: 20120271060
    Abstract: A method for the preparation of 2,5-furan dicarboxylic acid includes the step of contacting a feed comprising a compound selected from the group consisting of 5-hydroxymethylfurfural (“HMF”), an ester of 5-hydroxymethyl-furfural, 5-methylfurfural, 5-(chloromethyl)furfural, 5-methylfuroic acid, 5-(chloromethyl)furoic acid, 2,5-dimethylfuran and a mixture of two or more of these compounds with an oxidant in the presence of an oxidation catalyst at a temperature higher than 140° C.
    Type: Application
    Filed: October 6, 2010
    Publication date: October 25, 2012
    Applicant: FURANIX TECHNOLOGIES B.V.
    Inventors: Cesar Muñoz de Diego, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
  • Patent number: 8277521
    Abstract: Accordingly, the current invention provides a method for the manufacture of a mixture of a furfural and a 5-(alkoxymethyl)furfural derivative by reacting a C5 and C6 sugar-containing starting material with an alcohol in the presence of an acid catalyst, followed by the hydrogenation and/or etherification of the mixture of furfural and 5-(alkoxymethyl)furfural to convert the aldehyde function of both 5-(alkoxymethyl)furfural and furfural into an alkoxymethyl function or methyl function.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: October 2, 2012
    Assignee: Furanix Technologies B.V.
    Inventor: Gerardus Johannes Maria Gruier
  • Patent number: 8242293
    Abstract: Method for the manufacture of organic acid esters of 5-hydroxymethylfurfural by reacting a fructose or glucose-containing starting material with an organic acid or its anhydride in the presence of a catalytic or sub-stoechiometric amount of solid acid catalyst. The catalysts are heterogeneous and may be employed in a continuous flow fixed bed reactor. The esters can be applied as a fuel or fuel additive.
    Type: Grant
    Filed: March 12, 2007
    Date of Patent: August 14, 2012
    Assignee: Furanix Technologies B.V.
    Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
  • Patent number: 8231693
    Abstract: The present invention concerns a method for the manufacture of a 5-substituted 2-(alkoxymethyl)furan (or a mixture of such furans) by reacting a starting material comprising at least a 5-substituted furfural with hydrogen in the presence of an alcohol and a catalyst system.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: July 31, 2012
    Assignee: Furanix Technologies B.V.
    Inventor: Gerardus Johannes Maria Gruter
  • Publication number: 20120083610
    Abstract: Method for the manufacture of 5-alkoxymethylfurfural derivatives by reacting a fructose and/or glucose-containing starting material with an alcohol in the presence of a catalytic or sub-stoechiometric amount of heterogeneous acid catalyst. The catalysts may be employed in a continuous flow fixed bed or catalytic distillation reactor. The ethers can be applied as a fuel or fuel additive.
    Type: Application
    Filed: December 8, 2011
    Publication date: April 5, 2012
    Applicant: FURANIX TECHNOLOGIES B.V.
    Inventors: Gerardus Johannes Maria Gruter, F. Dautzenberg