Patents Assigned to Furanix Technologies B.V.
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Patent number: 9162960Abstract: 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: GrantFiled: September 28, 2012Date of Patent: October 20, 2015Assignee: Furanix Technologies B.V.Inventors: Matheus Adrianus Dam, Edserd de Jong, Jacco van Haveren, Aliaksei Pukin
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Patent number: 9145526Abstract: 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 definitioType: GrantFiled: May 1, 2013Date of Patent: September 29, 2015Assignee: FURANIX TECHNOLOGIES B.V.Inventors: Gerardus Johannes Maria Gruter, Edserd de Jong
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Patent number: 9090581Abstract: 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: GrantFiled: December 28, 2011Date of Patent: July 28, 2015Assignee: FURANIX TECHNOLOGIES B.V.Inventors: Ana Sofia Vagueiro de Sousa Dias, Gerardus Johannes Maria Gruter, Robert-Jan van Putten
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Patent number: 9073886Abstract: 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: GrantFiled: December 29, 2011Date of Patent: July 7, 2015Assignee: FURANIX TECHNOLOGIES B.V.Inventors: Laszlo Sipos, Michael Leroy Olson
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Patent number: 8877950Abstract: 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: GrantFiled: December 15, 2010Date of Patent: November 4, 2014Assignee: Furanix Technologies B.V.Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
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Patent number: 8865921Abstract: 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: GrantFiled: October 6, 2010Date of Patent: October 21, 2014Assignee: Furanix Technologies B.V.Inventors: Cesar Muñoz De Diego, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
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Publication number: 20140235892Abstract: 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: ApplicationFiled: September 28, 2012Publication date: August 21, 2014Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Matheus Adrianus Dam, Edserd de Jong, Jacco van Haveren, Alaiksai Pukin
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Publication number: 20130345453Abstract: 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: ApplicationFiled: December 29, 2011Publication date: December 26, 2013Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Laszlo Sipos, Michael Leroy Olson
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Publication number: 20130324708Abstract: 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: ApplicationFiled: December 28, 2011Publication date: December 5, 2013Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Ana Sofia Vagueiro de Sousa Dias, Gerardus Johannes Maria Gruter, Robert-Jan van Putten
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Publication number: 20130303792Abstract: 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 definitioType: ApplicationFiled: May 1, 2013Publication date: November 14, 2013Applicant: Furanix Technologies B.V.Inventors: Gerardus Johannes Maria Gruter, Edserd de Jong
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Patent number: 8519167Abstract: 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: GrantFiled: October 6, 2010Date of Patent: August 27, 2013Assignee: Furanix Technologies B.V.Inventors: Cesar Muñoz De Diego, Wayne Paul Schammel, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
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Patent number: 8435313Abstract: 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: GrantFiled: May 19, 2009Date of Patent: May 7, 2013Assignee: Furanix Technologies, B.V.Inventors: Gerardus Johannes Maria Gruter, Edserd de Jong
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Patent number: 8338626Abstract: 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: GrantFiled: December 8, 2011Date of Patent: December 25, 2012Assignee: Furanix Technologies B.V.Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
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Patent number: 8314260Abstract: 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: GrantFiled: September 5, 2008Date of Patent: November 20, 2012Assignee: Furanix Technologies B.V.Inventors: Gerardus Johannes Maria Gruter, Leo Ernest Manzer, Ana Sofia Vagueiro De Sousa Dias, Frits Dautzenberg, Jindra Purmova
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Publication number: 20120283452Abstract: 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: ApplicationFiled: October 6, 2010Publication date: November 8, 2012Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Cesar Muñoz De Diego, Wayne Paul Schammel, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
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Publication number: 20120271060Abstract: 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: ApplicationFiled: October 6, 2010Publication date: October 25, 2012Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Cesar Muñoz de Diego, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
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Patent number: 8277521Abstract: 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: GrantFiled: September 5, 2008Date of Patent: October 2, 2012Assignee: Furanix Technologies B.V.Inventor: Gerardus Johannes Maria Gruier
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Patent number: 8242293Abstract: 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: GrantFiled: March 12, 2007Date of Patent: August 14, 2012Assignee: Furanix Technologies B.V.Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
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Patent number: 8231693Abstract: 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: GrantFiled: September 5, 2008Date of Patent: July 31, 2012Assignee: Furanix Technologies B.V.Inventor: Gerardus Johannes Maria Gruter
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Publication number: 20120083610Abstract: 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: ApplicationFiled: December 8, 2011Publication date: April 5, 2012Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Gerardus Johannes Maria Gruter, F. Dautzenberg