The Hetero Ring Contains Five Members Including Carbon And Chalcogen Patents (Class 44/350)
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Patent number: 10898888Abstract: The present disclosure discloses the preparation and application of magnetic metallic oxide cross-linked acidic polyionic liquid, belonging to the technical field of solid acid catalysis. The catalyst prepared by the present disclosure has good Lewis acid site and Brönsted acid site, and has the characteristics of high speed, high efficiency, environment friendliness and the like when catalyzing preparation of furfural from xylose. The catalyst has the advantages of easy separation, multiple cycles of recycling and the like, and is green and pollution-free. The magnetic metal oxide cross-linked acidic polyionic liquid prepared by using the present disclosure has the characteristics of high speed, high efficiency, environment friendliness and the like when catalyzing preparation of furfural from xylose, and meanwhile, the catalyst has the advantages of easy separation, multiple cycles of recycling and the like, and is green and pollution-free.Type: GrantFiled: March 20, 2019Date of Patent: January 26, 2021Assignee: JIANGNAN UNIVERSITYInventors: Haijun Wang, Chunyan Wu, Yi Huang, Wenwen Yuan
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Patent number: 10301563Abstract: Gasoline blends and methods for producing gasoline blends containing high concentrations of a butanol isomer and having good cold start and warm-up driveability characteristics are disclosed.Type: GrantFiled: June 10, 2016Date of Patent: May 28, 2019Assignee: Butamax Advanced Biofuels LLCInventors: Rowena Justo Torres-Ordonez, Melanie Kuberka, Peter Placzek, Leslie R. Wolf, James J. Baustian
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Patent number: 10081611Abstract: An improved process for acid-catalyzed acylation using water-tolerant Lewis acid catalysts is described. The method involves reacting a reduction products of 5-(hydroxylmethyl)-furfural (HMF), in particular either furan-2,5-dimethanol (FDM) or bis-2,5-(hydroxymethyl)-tetrahydrofuran (bHMTHFs), with an excess of an organic acid in the presence of a Lewis acid metal triflate at a temperature and time sufficient to produce esters. The conversions of the reduction products of HMF to corresponding diesters can be quantitative with certain favored Lewis acids catalysts.Type: GrantFiled: November 21, 2014Date of Patent: September 25, 2018Inventor: Kenneth Stensrud
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Patent number: 10066168Abstract: A process for liquefying a cellulosic material to produce a liquefied product from cellulosic material is provided. Products obtained from such process and use of such products to prepare biofuels is also provided.Type: GrantFiled: May 17, 2016Date of Patent: September 4, 2018Assignee: SHELL OIL COMPANYInventors: Klaas Lambertus Von Hebel, Jean Paul Andre Marie Joseph Ghislain Lange
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Patent number: 9988362Abstract: The present invention relates to a method for preparing for a furan derivative from biomass, comprising step (1) of preparing 5-hydroxymethylfurfural by reacting biomass and a solid acid catalyst in butanol; and step (2) of preparing a furan derivative by reacting the butanol solution of 5-hydroxymethylfurfural, obtained in step (1), with a hydrogenation catalyst.Type: GrantFiled: April 14, 2016Date of Patent: June 5, 2018Assignee: Korea Research Institute of Chemical TechnologyInventors: Dong Won Hwang, Pravin P. Upare, Jong San Chang, Young Kyu Hwang, U Hwang Lee, Do Young Hong
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Patent number: 9656980Abstract: Provided are catalysts suitable for the production of tetrahydrofuran from 1,4-butanediol. Also provided are methods of use of these catalyst, as well as catalyst systems. The catalysts described herein contain only Lewis acidity, but not Broønsted acidity, which results in decreased production of ether byproducts.Type: GrantFiled: November 21, 2014Date of Patent: May 23, 2017Assignee: BASF CORPORATIONInventors: Rostam Jal Madon, Rolf Pinkos, Olga Osetska, Deepak S Thakur, Ronald L. Jagta
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Patent number: 9611197Abstract: A filter media for the removal of undesirable solid components from a fuel feedstock contains biomass and a catalyst used from the thermocatalytic conversion of biomass into bio-oil.Type: GrantFiled: March 14, 2014Date of Patent: April 4, 2017Assignee: Inaeris Technologies, LLCInventors: Changan Zhang, Ronny W. Lin, Lorenz J. Bauer, Ronald Cordle
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Patent number: 9403787Abstract: An object of the present invention is to provide a method for suppressing the corrosion of a reactor and reducing waste in the production of 2-furaldehyde from a sugar raw material containing a hexose as a constituent component, and another object of the invention is to provide an industrially advantageous method for producing 2-furaldehyde, which suppresses a decrease in the activity of a catalyst in a case of using an acid catalyst and provides a higher yield. The present invention relates to a method for producing 2-furaldehyde comprising heating a sugar raw material containing a hexose as a constituent component in an aprotic polar solvent in the presence of a solid acid catalyst.Type: GrantFiled: July 29, 2013Date of Patent: August 2, 2016Assignee: MITSUBISHI CHEMICAL CORPORATIONInventors: Toru Okoshi, Hideto Tsuji
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Publication number: 20150113860Abstract: The object of the present invention relates to a composition that can be used as fuel comprising: at least one hydrocarbon mixture at least one hydrophobic ketal or acetal of glycerine. Said composition can be advantageously used as fuel for diesel or gasoline engines.Type: ApplicationFiled: April 3, 2013Publication date: April 30, 2015Applicant: ENI S.p.A.Inventors: Alberto De Angelis, Giulio Assanelli, Paolo Pollesel
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Publication number: 20150047251Abstract: Ester derivatives of furoic acids and in particular of 5-methyl-2-furoic acid can be used as fuel as fuel additives. Such esters can be used to displace crude oil products such as gasoline, diesel, jet fuel, etc. As fuel additives, such esters had been shown to improve the performance of spark ignition internal combustion engines, compression ignition internal combustion engines. In addition, testing shows indications that said molecule will improve the performance of air breathing engines as well.Type: ApplicationFiled: October 1, 2014Publication date: February 19, 2015Inventors: Peter Mikochik, Aviad Cahana
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Patent number: 8821594Abstract: Disclosed herein is a fuel oil composition with enhanced conductivity. The oil composition comprises a Petroleum Based Component and a combination of Lubricity and Conductivity additives. In one aspect, additional additives can be added such as: (a) low temperature operability/cold flow additives, (b) corrosion inhibitors, (c) cetane improvers, (d) detergents, and (e) dyes and markers (f) anti-icing additives, (g) demulsifiers/anti haze additives, (h) antioxidants, (i) metal deactivators, (j) biocides, and (k) thermal stabilizers. Further, the present disclosure describes a method of using such composition is described.Type: GrantFiled: September 27, 2006Date of Patent: September 2, 2014Assignee: Innospec Fuel Specialities LLCInventors: Cenk R. Burgazli, Cyrus P. Henry, Jr.
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Patent number: 8795393Abstract: Disclosed is a method of preparing a petroleum-alternative bio fuel material such as 5-hydroxymethyl-2-furfural (HMF), 5-alkoxymethyl-2-furfural, levulinic acid alkil ester, etc. through a single process without saccharification, using a catalyst conversion reaction, from galactan that can be massively supplied at low costs and extracted from macroalgae of marine reusable resources. Thus, the macroalgae of the marine biomass resources is used so that a carbon source can be more easily extracted than that of a lignocellulosic biomass resource without a problem of having an effect on grain price like a crop-based biomass.Type: GrantFiled: April 15, 2010Date of Patent: August 5, 2014Assignee: Korea Institute of Industrial TechnologyInventors: Jin-Ku Cho, Sang-Yong Kim, Do-Hoon Lee, Bo-Ra Kim, Jae-Won Jung
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Patent number: 8715372Abstract: Diesel cycle fuel compositions are described containing at least one dianhydrohexitol compound according to the general formula 2 and/or its derived hydrocarbyl ethers or nitric ethers compounds, where the R? and R? substituents are both H or one or both of R? and R? is alkyl, cycloalkyl or phenyl, or one or both are —NO2. A preferred fuel composition is that containing dimethyl isosorbide (DMI) added or not of isosorbide dinitrate (ISDN) as ignition improver. The dianhydrohexitols compounds form compositions with at least one of the components selected among petroleum-derived diesel fuel, biodiesel, ethanol and water. The mixture of DMI and ISDN has excellent cetane number (IQT). Still, the oxygenated nature of the dianhydrohexitols and related compounds of the fuel compositions inhibits soot formation upon burning of the said Diesel cycle fuel compositions.Type: GrantFiled: August 10, 2009Date of Patent: May 6, 2014Assignee: Petroleo Brasileiro S.A.—PetrobrasInventors: Rafael Menegassi De Almeida, Carlos Rene Klotz Rabello
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Publication number: 20140075830Abstract: A biofuel consisting of a mixture of furanic compounds and polymethoxy benzene compounds which can be mixed with standard fuel consisting in hydrocarbons, and the process to obtain these compounds from sugar cane by converting cellulose, hemicellulose and sugars in furan derivatives and levullinic acid esthers and by converting lignin in alkoxy benzene compounds by hydrolysing the cellulose and lignin of sugar cane first in a mixture of N alkyl imidazolium chloride, hydrochloric acid 37% and an alcohol, dehydrating pentoses and hexoses so obtained from cellulose, stabilising the aldehyde groups as acetal and stabilising the phenolic hydroxyls obtained from lignin as alkyl ethers.Type: ApplicationFiled: September 14, 2012Publication date: March 20, 2014Inventor: Pedro Manuel Brito da Silva Correia
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Publication number: 20140007497Abstract: The invention provides new methods for the direct umpolung self-condensation of 5-hydroxymethylfurfural (HMF) by organocatalysis, thereby upgrading the readily available substrate into 5,5?-di(hydroxymethyl)furoin (DHMF). While many efficient catalyst systems have been developed for conversion of plant biomass resources into HMF, the invention now provides methods to convert such nonfood biomass directly into DHMF by a simple process as described herein. The invention also provides highly effective new methods for upgrading other biomass furaldehydes and related compound to liquid fuels. The methods include the organocatalytic self-condensation (umpolung) of biomass furaldehydes into (C8-C12)furoin intermediates, followed by hydrogenation, etherification or esterification into oxygenated biodiesel, or hydrodeoxygenation by metal-acid tandem catalysis into premium hydrocarbon fuels.Type: ApplicationFiled: July 2, 2013Publication date: January 9, 2014Inventors: Eugene Y. CHEN, Dajiang LIU
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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: 8372164Abstract: A gasoline composition containing in the range of from 0.1 to 30 wt % alkylfurfuryl ether with an alkyl group having 1 to 4 carbon atoms is provided. The gasoline composition is prepared by blending the alkylfurfuryl ether in a gasoline base fuel. The alkylfurfuryl ether is prepared by reacting an alkyl alcohol having in the range of 1 to 4 carbon atoms is reacted with furfuryl alcohol by contacting a liquid phase comprising the alkyl alcohol and furfuryl alcohol with an acidic zeolite catalyst at a temperature in the range of from 50 to 200° C.Type: GrantFiled: December 18, 2008Date of Patent: February 12, 2013Assignee: Shell Oil CompanyInventors: Rene Johan Haan, Jean-Paul Lange
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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: 20120110899Abstract: An additive mixture for fuels including a) at least one N-formal, b) at least one antioxidant and c) at least one corrosion inhibitor. The additive mixture ensures that the additized fuels and lubricants have biocidal and corrosion-inhibiting additization, especially when they include proportions of renewable raw materials, such as biodiesel, and when they are in contact with copper-containing surfaces.Type: ApplicationFiled: June 21, 2010Publication date: May 10, 2012Applicant: L'AIR LIQUIDE SOCIETE ANONYME POUR L'ETUDE ET L'EXPLOITATION DES PROCEDES GEORGInventors: Wolfgang Beilfuss, Ralf Grastke, Jennifer Knopf, Ingo Krull
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Publication number: 20120077234Abstract: A method and system are provided for producing biofuel from cellulosic feedstock. In the method, the cellulosic feedstock is pretreated to separate cellulose, hemicellulose, and lignin. Thereafter, the cellulose and hemicellulose are converted into sugars through enzymatic hydrolysis. Then, the sugars are converted into lipids, e.g. triglycerides, through a microbial process. Specifically, heterotrophic microalgae is grown on the triglycerides and forms triglycerides. While triglycerides are formed from the cellulose and hemicellulose, the lignin is converted into ringed hydrocarbons, such as aromatic hydrocarbons and cycloalkanes, e.g., cycloparaffins. To form the biofuel, the triglycerides and ringed hydrocarbons are processed together. During this step, the triglycerides are converted into straight chain paraffins and esters. Preferably, the biofuel is a surrogate for jet quality JP-8 fuel.Type: ApplicationFiled: September 29, 2010Publication date: March 29, 2012Inventor: David A. Hazlebeck
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Patent number: 8142525Abstract: This invention describes the preparation of fatty acid esters of glycerol formal either by a triglyceride transesterification process or, alternatively, by an esterification process of fatty acids previously obtained from the hydrolysis of triglycerides (fat splitting), with glycerol formal in the presence of an acid or basic catalyst. Also the invention describes the use of these fatty acid esters of glycerol formal prepared by said process as biofuel. In an embodiment, such biofuel is used in the preparation of other biofuels by its mixture with a product selected from a group formed by: glycerol formal, biodiesel, petrol-derived diesel, and mixtures thereof. The biofuels thus obtained are characterized to allow the complete incorporation of the glycerol obtained in the current biodiesel production process in a biodiesel fuel.Type: GrantFiled: July 11, 2007Date of Patent: March 27, 2012Assignee: Institut Univ. De Ciencia I Tecnologia, S.A.Inventors: Carles Estevez Company, Natividad Bayarri Ferrer, Josep Castells Boliart
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Patent number: 8133289Abstract: 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 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: March 12, 2007Date of Patent: March 13, 2012Assignee: Furanix Technologies B.V.Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
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Publication number: 20110302826Abstract: 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: ApplicationFiled: September 5, 2008Publication date: December 15, 2011Applicant: Furanix Technologies B.V.Inventor: Gerardus Johannes Maria Gruter
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Publication number: 20110173877Abstract: A process for preparing a hydrocarbon or mixture of hydrocarbons comprising the steps of (i) hydrogenating furfural, 5-hydroxymethylfurfural or a mixture of furfural and 5-hydroxymethylfurfural to provide furfuryl alcohol, 2,5-furandimethanol or a mixture of furfuryl alcohol and 2,5-furandimethanol; (ii) oligomerizing the alcohol or mixture of alcohols of step (i) in the presence of an acidic catalyst to provide a carbon-carbon coupled oligomer; and (iii) hydrogenating the oligomer of step (ii) is provided. The hydrocarbons are useful as fuel blending components. Processes for controlling the oligomerization of alcohol or mixture of alcohols to optimise the production of oligomers suitable for conversion to hydrocarbons useful as kerosene and diesel components are also provided.Type: ApplicationFiled: December 17, 2010Publication date: July 21, 2011Inventors: Jeroen Van Buijtenen, Jean-Paul Lange, Richard John Price
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Publication number: 20110154724Abstract: Compositions containing unsaturated fatty esters may be stabilized against atmospheric oxidation by the addition of an antioxidant package containing at least one nitroxide free-radical scavenger and at least one alkylalkanolamine. Compositions treated in this manner show good resistance to atmospheric oxidation and resultant viscosity increase. An advantage of the nitroxide free-radical scavenger is that it stops the oxidation of the unsaturated fatty esters already during the initiation stage. Moreover, it is much less volatile than for example the known alkylhydroxylamine oxygen scavengers. By the use of a nitroxide free-radical scavenger, the composition can thus be stabilized for a longer period of time. The stability period is moreover less affected by the supply of oxygen to the composition. The solubility problem of the nitroxide in the fatty ester component can be solved by dissolving the nitroxide first in the alkylalkanolamine.Type: ApplicationFiled: August 28, 2009Publication date: June 30, 2011Applicant: TAMINCOInventors: Nicholas M. Martyak, Daniel Alford, Conor M. Dowling, Michael D. Gernon
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Publication number: 20110138681Abstract: A process and system for separating bio-gasoline, bio-diesel and bio-fuel oil fractions from a bio-oil, and for producing a renewable gasoline including at least in part the bio-gasoline fraction, is provided. The process comprises separating bio-oil into a bio-gasoline fraction and a heavy fraction based on their boiling points. At least a portion of the bio-gasoline fraction is directly blended with a petroleum-derived gasoline, without any prior hydrotreatment, to thereby provide a renewable gasoline composition.Type: ApplicationFiled: October 29, 2010Publication date: June 16, 2011Applicant: KiOR, Inc.Inventors: Maria Magdalena Ramirez Corredores, Vicente Sanchez Iglesias
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Publication number: 20110107659Abstract: The invention provides a fuel composition comprising a ring-hydrogenated alkyl furfuryl ether of the general formula (I): (I) R?-TF-CH2-O—R wherein TF represents a 2,5-disubstituted tetrahydrofuran ring, wherein each R independently represents a hydrocarbyl group having from 1 to 20 carbon atoms and wherein 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? wherein each R? independently represents a hydrocarbyl group having from 1 to 20 carbon atoms. The invention also provides novel and useful ring-hydrogenated alkoxymethyltetrahydrofuran ethers of the general formula (I) above. Moreover, these ring-hydrogenated alkoxymethyltetrahydrofuran ethers disclosed herein have never been used as fuel component, and therefore the use of these ethers has also been claimed as an invention. A further embodiment of the current invention is the process for preparing these components.Type: ApplicationFiled: May 19, 2009Publication date: May 12, 2011Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Gerardus Johannes Maria Gruter, Edserd de Jong
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Publication number: 20110035991Abstract: A gasoline composition containing in the range of from 0.1 to 30 wt % alkylfurfuryl ether with an alkyl group having 1 to 4 carbon atoms is provided. The gasoline composition is prepared by blending the alkylfurfuryl ether in a gasoline base fuel. The alkylfurfuryl ether is prepared by reacting an alkyl alcohol having in the range of 1 to 4 carbon atoms is reacted with furfuryl alcohol by contacting a liquid phase comprising the alkyl alcohol and furfuryl alcohol with an acidic zeolite catalyst at a temperature in the range of from 50 to 200° C.Type: ApplicationFiled: December 18, 2008Publication date: February 17, 2011Applicant: SHELL OIL COMPANYInventors: Rene Johan Haan, Jean-Paul Lange
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Publication number: 20100319243Abstract: The present disclosure relates to a gasoline combustion improver comprising an organic nitro compound with C—NO2 bond dissociation energy of about 60 to about 80 Kcal/mol of compound, wherein the organic nitro compound is selected from the group consisting of nitro-aromatics, heteroatom aromatic ring compounds, heteroatom nonaromatic ring compounds, and nitrated furfuryls, and wherein the organic nitro compound is not nitrotoluene or dinitrotoluene.Type: ApplicationFiled: June 22, 2009Publication date: December 23, 2010Applicant: Afton Chemical CorporationInventors: Allen A. ARADI, Joseph W. Roos
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Publication number: 20100218415Abstract: Accordingly, the current invention provides a method for the manufacture of an ether of 5-hydroxymethylfurfural by reacting a hexose-containing starting material with a higher alcohol in the presence of an acid catalyst, and at a temperature in the range of from 125 to 250 degrees Centigrade.Type: ApplicationFiled: September 5, 2008Publication date: September 2, 2010Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Gerardus Johannes Maria Gruter, Leo Ernest Manzer
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Publication number: 20100218416Abstract: The current invention provides a method for the manufacture of an ether of 5-hydroxymethylfurfural by reacting a hexose-containing starting material with a branched C3-C20 monoalcohol in the presence of a catalytic or sub-stoichiometric amount of an acid catalyst.Type: ApplicationFiled: September 5, 2008Publication date: September 2, 2010Applicant: FURANIX TECHNOLOGIES B.V.Inventor: Gerardus Johannes Maria Gruter
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Publication number: 20100212217Abstract: The current invention provides a method for the manufacture of an ether of 5-hydroxymethylfurfural through hydroxy-alkoxy-addition by reacting 5-hydroxymethylfurfural with an olefin in the presence of an acid catalystType: ApplicationFiled: September 5, 2008Publication date: August 26, 2010Applicant: Furanix Technologies B.V.Inventor: Gerardus Johannes Maria Gruter
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Publication number: 20100083565Abstract: 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: ApplicationFiled: September 5, 2008Publication date: April 8, 2010Applicant: FURANIX TECHNOLOGIES B.V.Inventor: Gerardus Johannes Maria Gruter
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Publication number: 20100058650Abstract: Accordingly, the current invention provides a method for the manufacture of a mixture of 5-hydroxymethylfurfural ethers by reacting a hexose-containing starting material or HMF with mixed alcohols in the presence of an acid catalyst.Type: ApplicationFiled: September 5, 2008Publication date: March 11, 2010Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Gerardus Johannes Maria Gruter, Leo Ernest Manzer
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Publication number: 20090313889Abstract: The invention provides a process for making hydroxymethylfurfural. A reaction mixture comprising a saccharide and a metal complex of an N-heterocyclic carbene is initially provided. The saccharide is then allowed to react at about 70° C. or below to form hydroxymethylfurfural. The saccharide may be a hexose or a mixture of hexoses, or a dimer, oligomer or polymer or copolymer of a hexose or a mixture thereof.Type: ApplicationFiled: April 8, 2009Publication date: December 24, 2009Applicant: Agency for Science, Technology and ResearchInventors: Yugen ZHANG, Jin Y.G. Chan
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Patent number: 7520905Abstract: Aqueous sulfuric acid is used for hydrolysis of a biomass, constituting a hydrolysate, to produce organic compounds. Organic compounds such as furfural and hyroxymethylfurfural are formed within the hydrolysate. Heterocyclic ring opening within hyroxymethylfurfural forms levulinic acid within the hydrolysate. Furfural and levulinic acid are extracted by a biodiesel fuel oil to increase content of biodiesel fuel oil. Biodiesel fuel oil generally consists of vegetable oils, insoluble in aqueous sulfuric acid, and affords access to, extraction of furfural and levulinic acid. Extracted hydrolysate is recycled for further hydrolysis of biomass.Type: GrantFiled: February 6, 2006Date of Patent: April 21, 2009Inventor: Gene E Lightner
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Patent number: 7323020Abstract: A method of making a fuel composition for a modified internal combustion spark ignition engine comprising combining a fuel grade ethanol, an oxygen-containing component and at least one C6-C12 hydrocarbon. A fuel produced by such a method is also provided.Type: GrantFiled: December 15, 2003Date of Patent: January 29, 2008Inventors: Angelica Hull, Igor Golubkov
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Patent number: 7195656Abstract: Fuel compositions containing (a) pulverized coal; and (b) an oxygenate selected from glycerol, glycerol derivatives, propylene glycol, propylene glycol derivatives, ethylene glycol, ethylene glycol derivatives, fatty acid alkyl esters, fatty alcohols, and mixtures thereof. Methods of reducing the NOx emissions generated from the burning of pulverized coal in a heat-producing unit, wherein the method comprises the steps of: (a) introducing pulverized coal into a combustion chamber of the heat-producing unit; and (b) co-firing the pulverized coal with an oxygenate source selected from glycerol, glycerol derivatives, propylene glycol, propylene glycol derivatives, ethylene glycol, ethylene glycol derivatives, fatty acid alkyl esters, fatty alcohols, and mixtures thereof, where the combustion of the oxygenate source generates at least 2.5%, on a heat input basis, of the total heat generated by the co-firing.Type: GrantFiled: July 2, 2003Date of Patent: March 27, 2007Assignee: Procter & Gamble CompanyInventors: Donald Benjamin Appleby, Joia Kirin Spooner-Wyman
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Patent number: 7175678Abstract: The present invention provides a polymeric a fuel composition comprising (i) a fuel; and (ii) a polymeric compound; wherein the polymeric compound comprises at least one monomer unit of Formula I wherein R1 is H or a C1-10 hydrocarbyl group; wherein L is an optional C1-30 hydrocarbyl linker group; and wherein heterocycle is an optionally substituted heterocyclic ring.Type: GrantFiled: September 26, 2003Date of Patent: February 13, 2007Assignee: Innospec LimitedInventors: Cyrus Pershing Henry, David Leonard Pinch, Andrea Sneddon, Derek Richard Green
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Patent number: 7097674Abstract: A diese fuel composition containing a major proportion of at least one diesel fuel and a minor proportion of at least one glycerol acetal carbonate of the formulae: in which: R1 and R2 each represent a hydrogen atom, a hydrocarbon radical with 1 to 20 carbon atoms that is aliphatic, cycloaliphatic or aromatic, an alkyl-ether chain, whereby R1 and R2 together can form an oxygenated heterocyclic radical; R3 is a radical that is defined as R1 or R2, except for the hydrogen atom, or a radical of the formula: where R1 and R2 are defined as above.Type: GrantFiled: December 19, 2002Date of Patent: August 29, 2006Assignee: Institut du PetroleInventors: Bruno Delfort, Isabelle Durand, Anne Jaecker, Thierry Lacome, Xavier Montagne, Fabrice Paille
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Patent number: 6890364Abstract: A diesel fuel compound has a major proportion of at least one diesel fuel and a minor proportion of at least one glycerol acetal corresponding to one of general formulas: in which: R1 and R2 each represent a hydrogen atom, a hydrocarbon radical with 1 to 20 carbon atoms, aliphatic, cycloaliphatic or aromatic, or an alkyl-ether chain, R1 and R2 being able together to form an oxygenated heterocyclic radical; R3 represents a hydrogen atom or a radical of general formula: where R4 is a radical defined as R1 or R2, except for the hydrogen atom, or a radical of general formula: where R1 and R2 are defined as above, the sum of the number of carbon atoms of R1, R2 and R3 in formulas (1) and (2) being at least 2 and it has no metal compounds of group IIA.Type: GrantFiled: December 19, 2002Date of Patent: May 10, 2005Assignee: InstitutFrancais du PetroleInventors: Bruno Delfort, Isabelle Durand, Anne Jaecker, Thierry Lacome, Xavier Montagne, Fabrice Paille
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Patent number: 6761745Abstract: A method of reducing the vapor pressure of a C3 to C12 hydrocarbon-based motor fuel mixture containing 0.1 to 20% by volume of ethanol for conventional spark ignition internal combustion engines, wherein, in addition to an ethanol component (b) and a C3 to C12 hydrocarbon component (a), an oxygen-containing additive (c) selected from at least one of the following types of compounds: alcohol other than ethanol, ketone, ether, ester, hydroxy ketone, ketone ester, and a heterocyclic-containing oxygen compound in an amount of at least 0.05 by volume of the total fuel and at least one C6-C12 hydrocarbon (d) are used in the fuel mixture, is disclosed. A mixture of fuel grade ethanol (b), oxygen-containing additive (c) and C6-C12 hydrocarbon (d) usable in the method of the invention is also disclosed.Type: GrantFiled: September 9, 2002Date of Patent: July 13, 2004Inventors: Angelica Hull, Igor Golubkov
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Publication number: 20040025417Abstract: A diesel fuel composition comprises a major proportion of at least one diesel fuel and a minor proportion of at least one glycerol acetal carbonate that corresponds to one of the general formulas: 1Type: ApplicationFiled: December 19, 2002Publication date: February 12, 2004Applicant: Institut Francais du PetroleInventors: Bruno Delfort, Isabelle Durand, Anne Jaecker, Thierry Lacome, Xavier Montagne, Fabrice Paille
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Patent number: 6676715Abstract: There is provided use of a thermal stabiliser for increasing the thermal stability of a cetane improver in a fuel composition comprising (i) a fuel, and (ii) the cetane improver wherein the thermal stabiliser is a compound of the formula H—R1 wherein H is a group comprising a heterocyclic group and R1 is a hydrocarbyl group having from 10 to 200 carbons.Type: GrantFiled: May 11, 2001Date of Patent: January 13, 2004Assignees: The Associated Octel Company Limited, Octel Starreon, LLCInventors: Cyrus Pershing Henry, Barbara Elizabeth Goodrich
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Patent number: 6656237Abstract: This invention provides a fuel composition having a sulphur content of not more than 50 ppm by weight and comprising at least 50 ppm based on the total weight of the fuel composition of at least one fused polycyclic aromatic compound which comprises at least one exocyclic group containing nitrogen wherein the nitrogen is attached directly to a ring carbon atom. Specific examples of such compounds include 1-amino naphthalene, 1,8-diaminonaphthalene, or 5-aminoindole, 2-(2-aminophenyl)indole and 8-aminoquinoline. These compounds are capable of improving the antiwear and lubricity properties of a low sulphur fuel when compared with that of the same fuel in the absence of such compounds.Type: GrantFiled: August 20, 2001Date of Patent: December 2, 2003Assignee: ExxonMobil Research and Engineering CompanyInventors: Robert Howie Barbour, David John Rickeard, Alan Mark Schilowitz
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Publication number: 20030163949Abstract: A diesel fuel compound has a major proportion of at least one diesel fuel and a minor proportion of at least one glycerol acetal corresponding to one of general formulas: 1Type: ApplicationFiled: December 19, 2002Publication date: September 4, 2003Applicant: Institut Francais du PetroleInventors: Bruno Delfort, Isabelle Durand, Anne Jaecker, Thierry Lacome, Xavier Montagne, Fabrice Paille
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Publication number: 20030154647Abstract: The invention provides photoluminescent markers consisting essentially of fluorene copolymers, which are colorless or nearly colorless to the naked eye and exhibit strong photoluminescence between about 380-800 nm upon exposure to ultra-violet radiation or laser light. The soluble fluorene copolymers described in this invention having a general formula as shown in Formula 1.Type: ApplicationFiled: December 26, 2001Publication date: August 21, 2003Inventors: My T. Nguyen, Francois Raymond, Steven Xiao
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Publication number: 20030154648Abstract: This invention is a fuel composition having a sulphur content of ≦50 ppm by weight and comprising ≧50 ppm by weight of at least one fused polycyclic aromatic compound which has at least one hetero-atom selected from O and N either (a) as a heterocyclic group, or, (b) as an exocyclic group in which the hetero-atom is attached either directly or through one other carbon atom to a ring carbon atom wherein the fused polycyclic aromatic compound is substituted on at least one of its ring carbon atoms by a C1-C4 alkyl group. These compounds are capable of improving the antiwear and lubricity properties of a low sulphur fuels, especially diesel fuels, when compared with the performance of the same fuel in the absence of such compounds.Type: ApplicationFiled: September 27, 2002Publication date: August 21, 2003Inventors: Robert Howie Barbour, David John Rickeard, Alan Mark Schilowitz