Catalyst Utilized Patents (Class 568/885)
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Patent number: 7834223Abstract: Process for the conversion of carbon oxide(s) and hydrogen containing feedstocks to oxygen-containing hydrocarbon compounds in the presence of a particulate catalyst, by reacting carbon oxide(s) and hydrogen in the presence of a particulate catalyst in a conversion reactor to form oxygen-containing hydrocarbon compounds. A saturated monocarboxylic acid having from 1 to 3 carbon atoms and/or an ester of a saturated monocarboxylic acid having from 1 to 3 carbon atoms with a monohydric aliphatic paraffinic alcohol having from 1 to 4 carbon atoms is added to the conversion reactor.Type: GrantFiled: May 18, 2006Date of Patent: November 16, 2010Assignee: BP Chemicals LimitedInventors: Martin Philip Atkins, Leslie William Bolton, Benjamin Patrick Gracey, John Glenn Sunley
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Patent number: 7834224Abstract: Disclosed are iron ligand catalysts for selective hydrogenation of aldehydes, ketones and imines. A catalyst such as dicarbonyl iron hydride hydroxycyclopentadiene) complex uses the OH on the five member ring and hydrogen linked to the iron to facilitate hydrogenation reactions, particularly in the presence of hydrogen gas.Type: GrantFiled: November 20, 2007Date of Patent: November 16, 2010Assignee: Wisconsin Alumni Research FoundationInventors: Charles P. Casey, Hairong Guan
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Publication number: 20100286454Abstract: A process for the co-production of a stream of a fatty alcohol having first carbon chain lengths and a stream of a fatty alcohol having a second carbon chain lengths, said second carbon chain lengths being longer than said first carbon chain lengths, said process comprising the steps of: (a) supplying a stream comprising lower alkyl esters of fatty acids having chain lengths comprising the first and second chain lengths to a first vaporisation zone and contacting said stream with an amount of hydrogen which is sufficient to vaporise the lower alkyl esters of the fatty acids having the first carbon chain lengths into the hydrogen; (b) supplying the hydrogen and the vaporised lower alkyl esters of fatty acids having the first carbon chain lengths to a first reaction zone comprising catalyst and operating under reaction conditions to allow hydrogenation to the desired alcohol having first carbon chain lengths; (c) recovering from the first reaction zone an alcohol product stream having first carbon chain lengthsType: ApplicationFiled: October 3, 2008Publication date: November 11, 2010Applicant: DAVY PROCESS TECHNOLOGY LIMITEDInventors: Donald Hugh McKinley, Richard John Hensman, Andrew George Hiles, Rikard Umberto Andersson
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Patent number: 7777083Abstract: A process for the reduction of compounds comprising one or more carbon-oxygen (C?0) double bonds, to provide the corresponding alcohol, comprising contacting the compound with hydrogen gas at a pressure greater than 3 atm and a catalyst comprising an iridium aminodiphosphine complex.Type: GrantFiled: May 30, 2008Date of Patent: August 17, 2010Assignee: Kanata Chemical Technologies Inc.Inventors: Kamaluddin Abdur-Rashid, Rongwei Guo, Xuanhua Chen, Wenli Jia
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Patent number: 7772445Abstract: The present disclosure relates to a process for the hydrogenation of compounds comprising one or more carbon-oxygen (C?O) double bonds, to provide the corresponding alcohol, comprising contacting the compound with hydrogen gas at and a catalyst comprising a ruthenium-aryl-aminophosphine complex.Type: GrantFiled: July 7, 2008Date of Patent: August 10, 2010Assignee: Kanata Chemical Technologies Inc.Inventors: Xuanhua Chen, Wenli Jia, Kamaluddin Abdur-Rashid, Rongwei Guo
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Publication number: 20100197985Abstract: A process for selective formation of ethanol from acetic acid by hydrogenating acetic acid in the presence of first metal, a silicaceous support, and at least one support modifier. Preferably, the first metal is selected from the group consisting of copper, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, titanium, zinc, chromium, rhenium, molybdenum, and tungsten. In addition the catalyst may comprise a second metal preferably selected from the group consisting of copper, molybdenum, tin, chromium, iron, cobalt, vanadium, tungsten, palladium, platinum, lanthanum, cerium, manganese, ruthenium, rhenium, gold, and nickel.Type: ApplicationFiled: February 2, 2010Publication date: August 5, 2010Applicant: CELANESE INTERNATIONAL CORPORATIONInventors: Victor J. Johnston, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, James H. Zink, Heiko Weiner, John L. Potts, Radmila Jevtic
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Publication number: 20100137625Abstract: An objective is to provide a process for preparing 1,5-pentanediol and/or 1,6-hexanediol comprising esterifying, with an alcohol such as methanol, ethanol, butanol or 1,6-hexanediol, a mixture of carboxylic acids such as glutaric acid, adipic acid and 6-hydroxycaproic acid which are a by-product in preparation of cyclohexanone by oxidation of cyclohexane with oxygen or an oxygen-containing gas; and hydrogenating the resulting esterified product in the presence of a copper-containing catalyst, which process is an industrially suitable process for preparing 1,5-pentanediol and/or 1,6-hexanediol in a high yield while controlling deterioration of the catalyst. The above objective is achieved by hydrogenating the esterified product with a catalyst obtained by prereducing a copper-containing catalyst in an alcohol having an acid value (AV) of 0.5 mg KOH/g or less or an ester having an acid value (AV) of 0.5 mg KOH/g or less.Type: ApplicationFiled: May 15, 2008Publication date: June 3, 2010Inventor: Hirofumi II
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Patent number: 7728182Abstract: The process for producing a predetermined CXHYOZ product from a primary feedstock containing hydrocarbons and a secondary feedstock is disclosed, wherein X, Y and Z are integers. The process includes the steps of: providing primary feedstock; indirectly heating it generally in the absence of oxygen; cleaning the gas stream produced therefrom by removing CO2 and solids; determining the amount of CO and H2 therein; comparing the percentage of CO and H2 in the cleaned gas stream with the required CO and H2 to produce the predetermined CXHYOZ product; determining the additional of CO and H2 required; determining the secondary feedstock; calculating the amount of CO, H2 and heat produced from the secondary feedstock; partially oxidizing the secondary feedstock to produce heat and a secondary gas stream; combining the CO and H2 from both feedstocks to produce a mixed gas stream; adding a catalyst; and distilling to produce the predetermined CXHYOZ product.Type: GrantFiled: July 19, 2005Date of Patent: June 1, 2010Assignee: Woodland Biofuels Inc.Inventors: Larry Jack Melnichuk, Karen (Sue) Venita Kelly
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Publication number: 20100121114Abstract: A process for selective formation of ethanol from acetic acid includes contacting a feed stream containing acetic acid and hydrogen at an elevated temperature with catalyst comprising platinum and tin on a high surface area silica promoted with calcium metasilicate. Selectivities to ethanol of over 85% are achieved at 280° C. with catalyst life in the hundreds of hours.Type: ApplicationFiled: October 26, 2009Publication date: May 13, 2010Inventors: Heiko Weiner, Victor J. Johnston, John L. Potts, Radmila Jevtic
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Publication number: 20100113837Abstract: Compounds of the formula (I) wherein R2 is a branched or unbranched, saturated or ethylenically mono or di unsaturated aliphatic radical, Z is —CH2OH, —CH2OAc or —CHO, m is a whole positive integer of one or more, and Ac is an acetyl group are synthesized by a process wherein a 1-alken-3-yl alkylate, is reacted with a halo alkanol Grignard reagent.Type: ApplicationFiled: October 31, 2008Publication date: May 6, 2010Inventors: Robert H. Bedoukian, Linda C. Passaro
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Publication number: 20100113843Abstract: Disclosed herein is a method for producing monohydric alcohols from monocarboxylic acids or derivatives thereof using a catalyst comprising ruthenium (Ru) and tin (Sn) using zinc oxide (ZnO) as both a catalyst support and an active promoter; a catalyst prepared by adding an inorganic binder such as silica, alumina or titania in a limited range to the catalyst comprising the above components in order to impart a shaping ability to the catalyst; or, a modified catalyst reformed by adding at least one reducing component selected from the group consisting of Co, Ni, Cu, Ag, Rh, Pd, Re, Ir, and Pt to the catalyst in order to improve the reducing ability of the catalyst.Type: ApplicationFiled: February 27, 2009Publication date: May 6, 2010Applicant: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGYInventors: Jung Ho Lee, Jong San Chang, Young Kyu Hwang, Hyun Kwan Shin, Kwang Myung Cho, Bong Keun Song, Yong Hwan Kim
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Patent number: 7709689Abstract: A homogenous process for the hydrogenation of the carboxylic acids and/or derivatives thereof in the presence of a catalyst comprising ruthenium, rhodium, iron, osmium or palladium, and an organic phosphine is described in which the hydrogenation is carried out in the presence of at least about 1% by weight water. A process for regenerating a catalyst comprising ruthenium, rhodium, iron, osmium or palladium and an organic phosphine is also described in which the regeneration is carried out in the presence of hydrogen and water.Type: GrantFiled: April 29, 2003Date of Patent: May 4, 2010Assignee: Davy Process Technololgy LimitedInventors: Melvyn Kilner, Derek Vincent Tyers, Simon Peter Crabtree, Michael Anthony Wood
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Patent number: 7663003Abstract: A process for hydrogenating an organic compound which has at least one carbonyl group, in which the organic compound is brought into contact in the presence of hydrogen with a shaped article which can be produced in a process in which (i) an oxidic material comprising copper oxide, aluminum oxide and at least one of the oxides of lanthanum, tungsten, molybdenum, titanium or zirconium is prepared, (ii) powdered metallic copper, copper flakes, powdered cement, graphite or a mixture thereof is added to the oxidic material, and (iii) the mixture resulting from (ii) is shaped to a shaped article.Type: GrantFiled: November 9, 2007Date of Patent: February 16, 2010Assignee: BASF AktiengesellschaftInventors: Sylvia Huber-Dirr, Michael Hesse, Andrea Haunert, Henrik Junicke
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Publication number: 20100029996Abstract: The present invention provides a catalyst for producing alcohols from carboxylic acids by hydrogenation, containing Co metal as an essential component and one or more elements selected from Zr, Y, La, Ce, Si, Al, Sc, V and Mo as a first co-catalyst component, and having 20% or more of cubic phase in the crystal phase of the Co metal, the method for producing the catalyst, and the method for producing an alcohol from a carboxylic acid as a raw material by hydrogenation using the catalyst.Type: ApplicationFiled: February 14, 2008Publication date: February 4, 2010Applicant: Kao CorporationInventors: Hiroshi Danjo, Noriaki Fukuoka, Taku Mimura
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Patent number: 7642386Abstract: The invention relates to a process for producing an alcohol from fats and oils, including: step 1 of reacting starting fats and oils with water to produce a reaction product containing a glycerin unit, and step 2 of subjecting the reaction product obtained in step 1 to a hydrogenation reaction in the presence of a catalyst in the coexistence of water in an amount of 0.5 mole or more relative to 1 mole of the glycerin unit contained in the reaction product.Type: GrantFiled: March 7, 2006Date of Patent: January 5, 2010Assignee: Kao CorporationInventors: Toru Sakamoto, Masanori Namba, Nobuhiro Tatsumi
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Patent number: 7608744Abstract: A process for the selective production of ethanol by vapor phase reaction of acetic acid over a hydrogenating catalyst composition to form ethanol is disclosed and claimed. In an embodiment of this invention reaction of acetic acid and hydrogen over either cobalt and palladium supported on graphite or cobalt and platinum supported on silica selectively produces ethanol in a vapor phase at a temperature of about 250° C.Type: GrantFiled: July 31, 2008Date of Patent: October 27, 2009Assignee: Celanese International CorporationInventors: Victor J. Johnston, Josefina T. Chapman, Laiyuan Chen, Barbara F. Kimmich, James H. Zink, Jan Cornelis van der Waal, Virginie Zuzaniuk
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Patent number: 7608743Abstract: An efficient and environmentally beneficial method of recycling and producing methanol from varied sources of carbon dioxide including flue gases of fossil fuel burning powerplants, industrial exhaust gases or the atmosphere itself. Converting carbon dioxide by chemical or electrochemical reduction secondary treatment to produce essentially methanol, dimethyl ether and derived products.Type: GrantFiled: June 21, 2007Date of Patent: October 27, 2009Assignee: University of Southern CaliforniaInventors: George A. Olah, G. K. Surya Prakash
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Patent number: 7605293Abstract: An environmentally beneficial method of producing methanol from varied sources of carbon dioxide including flue gases of fossil fuel burning powerplants, industrial exhaust gases or the atmosphere itself. Converting carbon dioxide by electrochemical reduction produces formic acid acid and some formaldehyde and methanol mixtures. The formic acid can be used as source of carbon as well as hydrogen to produce methanol, dimethyl ether and other products.Type: GrantFiled: April 12, 2006Date of Patent: October 20, 2009Assignee: University of Southern CaliforniaInventors: George A. Olah, G. K. Surya Prakash
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Patent number: 7579508Abstract: The invention provides a process for producing an alcohol, including the step of hydrogenating a glyceride in the presence of a catalyst, adding water, or a process for producing an alcohol, including the step of hydrogenating a glyceride in the presence of a catalyst and in the presence of from 0.5 or more of water per mole of the starting glyceride.Type: GrantFiled: September 8, 2004Date of Patent: August 25, 2009Assignee: Kao CorporationInventors: Toru Sakamoto, Osamu Tabata, Hideaki Ueoka
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Patent number: 7538060Abstract: Disclosed are catalysts comprising copper chromite, palladium and lanthanum having hydrogenation activity. The combination of copper chromite with palladium and lanthanum enhances catalyst activity more than the presence of either palladium alone or palladium in combination with alkali or alkaline earth metals. The catalysts are useful for the preparation of methanol from carbon monoxide and hydrogen and for the hydrogenation of carbonyl compounds such as, for example, aldehydes, ketones, and esters, to their corresponding alcohols. The catalysts may be used for the preparation of cyclohexanedimethanols from dialkyl cyclohexanedicarboxylates or of ethylene glycol from alkyl glycolates.Type: GrantFiled: February 14, 2007Date of Patent: May 26, 2009Assignee: Eastman Chemical CompanyInventors: Scott Donald Barnicki, Bruce LeRoy Gustafson, Zhufang Liu, Steven Thomas Perri, Paul Randolph Worsham
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Patent number: 7518022Abstract: The invention is directed to liquid vegetable unsaturated alcohol mixture having an iodine value of 88 to 100 and a cloud point less than 7° C., the unsaturated alcohol mixture being prepared by reduction of a vegetable unsaturated fatty acid mixture and/or an alkyl ester thereof in the presence of a zinc-type catalyst having a copper content of 30 ppm or less, the vegetable unsaturated fatty acid mixture being prepared from at least one vegetable oil selected from the group consisting of palm oil, coconut oil and palm kernel oil. The invention also concerns a liquid vegetable unsaturated alcohol mixture having an iodine value of 88 to 100, a cloud point less than 7° C. or lower and a conjugated diene content of 1 wt. % or less.Type: GrantFiled: April 17, 2003Date of Patent: April 14, 2009Assignee: New Japan Chemical Co., Ltd.Inventors: Hisao Nakaoka, Mamoru Mototani
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Publication number: 20090023962Abstract: The invention relates to a process for producing an alcohol from fats and oils, including: step 1 of reacting starting fats and oils with water to produce a reaction product containing a glycerin unit, and step 2 of subjecting the reaction product obtained in step 1 to a hydrogenation reaction in the presence of a catalyst in the coexistence of water in an amount of 0.5 mole or more relative to 1 mole of the glycerin unit contained in the reaction product.Type: ApplicationFiled: March 7, 2006Publication date: January 22, 2009Applicant: KAO CORPORATIONInventors: Toru Sakamoto, Masanori Namba, Nobuhiro Tatsumi
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Publication number: 20090018366Abstract: Method for the production of supported activated metal catalysts, whereby an alloy, a metal powder, a pore builder is dispersed in a water, the dispersion is sprayed on a support which is the dried, calcined and activated. The catalysts can be used for organic transformations, i.e. for hydrogenation reactions.Type: ApplicationFiled: September 8, 2005Publication date: January 15, 2009Inventors: Monika Berweiler, Daniel Ostgard, Thomas Quandt, Stefan Roder
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Patent number: 7459590Abstract: A method for producing methanol and dimethyl ether using the air as the sole source of materials is disclosed. The invention relates to a method for producing methanol by removing water from atmospheric air, obtaining hydrogen from the removed water, obtaining carbon dioxide from atmospheric air; and converting the carbon dioxide under conditions sufficient to produce methanol. Thereafter, the methanol can be dehydrated to produce dimethyl ether or further processed to produce synthetic hydrocarbons, polymers, and products derived from them.Type: GrantFiled: May 22, 2008Date of Patent: December 2, 2008Assignee: University of Southern CaliforniaInventors: George A. Olah, Robert Aniszfeld
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Publication number: 20080275145Abstract: A catalyst including cobalt, zinc oxide and aluminium is described, having a total cobalt content of 15-75% by weight (on reduced catalyst), an aluminium content ?10% by weight (based on ZnO) and which when reduced at 425° C., has a cobalt surface area as measured by hydrogen chemisorption at 150° C. of at least 20 m2/g cobalt. A method for preparing the catalyst is also described including combining a solution of cobalt, zinc and aluminium with an alkaline solution to effect co-precipitation of a cobalt-zinc-aluminium composition from the combined solutions, separating of the co-precipitated composition form the combined solutions, heating the composition to form an oxide composition, and optionally reducing at least a portion of the cobalt to cobalt metal. The catalysts may be used for hydrogenation reactions and for the Fischer-Tropsch synthesis of hydrocarbons.Type: ApplicationFiled: April 15, 2005Publication date: November 6, 2008Inventors: John Leonello Casci, Carl Leonard Huitson, Cornelis Martinus Lok
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Publication number: 20080242899Abstract: A process for producing purified alcohols yielding good results in the acid wash color test which comprises the condensation step of subjecting an aldehyde to aldol condensation and dehydration to obtain a corresponding condensate, the hydrogenation step of hydrogenating the condensate into a crude alcohol, and the purification step of distilling the crude alcohol to obtain a purified alcohol, characterized by feeding into the purification step a crude alcohol containing compounds having oxygenic heterocycles bearing carbon-carbon double bonds in the cycle in a concentration of as low as 200 ppm by weight or below. In particular, the aldehyde is n-butyraldehyde, the condensate is 2-ethylhexenal, and the alcohol is 2-ethylhexanol.Type: ApplicationFiled: March 14, 2005Publication date: October 2, 2008Applicant: MITSUBISHI CHEMICAL CORPORATIONInventors: Hirofumi Oota, Hiroki Kawasaki
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Patent number: 7408087Abstract: Unsaturated coconut and/or palm nut fatty alcohols having an iodine number in the range from 65 to 85, which essentially comprise unsaturated fatty alcohols and mixtures of saturated fatty alcohols of the formula (I): R1OH ??(I) in which R1 is a saturated or unsaturated, linear or branched alkyl radical having 12 to 20 carbon atoms, obtainable by fractionating coconut and/or palm nut fatty acid methyl esters to obtain a fraction containing predominantly C16-C18 portions, fractionating the C16-C18 fatty acid methyl ester fraction into a predominantly saturated distillate and a predominantly unsaturated bottom product, and hydrogenating the bottom product with retention of the double bonds to give the corresponding alcohols; are disclosed.Type: GrantFiled: June 5, 2001Date of Patent: August 5, 2008Assignee: Cognis Deutschland GmbH & Co. KGInventors: Stephan Heck, Norbert Klein, Horst-Dieter Komp, Christiane Boehr, Norbert Huebner, Alfred Westfechtel
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Patent number: 7378561Abstract: A method for producing methanol and dimethyl ether using the air as the sole source of materials is disclosed. The invention relates to a method for separating the water (i.e., the moisture in the air) and carbon dioxide content of atmospheric air for their use in the subsequent production of methanol, dimethyl ether and derived synthetic hydrocarbons as products. The method includes the conversion of carbon dioxide and water under conditions sufficient to produce methanol and/or dimethyl ether. Methanol and/or dimethyl ether can be used as fuel or fuel additives or further converted to synthetic hydrocarbons and their products. Carbon dioxide is captured on a suitable absorbent, preferentially polyethyleneimine supported on nano-structured fumed silica. The process can also involve hydrogenation with hydrogen produced by electrolysis of water obtained from the air or from any other water source.Type: GrantFiled: July 19, 2007Date of Patent: May 27, 2008Assignee: University of Southern CaliforniaInventors: George A. Olah, Robert Aniszfeld
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Patent number: 7265237Abstract: Certain chiral monophosphites and their monothio derivatives are suitable as ligands in the asymmetrical transition-metal-catalyzed hydrogenation, hydroborination and hydrocyanation of prochiral olefins, ketones and imines.Type: GrantFiled: June 5, 2001Date of Patent: September 4, 2007Assignee: Studiengesellschaft Kohle mbHInventors: Manfred T. Reetz, Gerlinde Mehler, Andreas Meiswinkel
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Patent number: 7217847Abstract: The invention relates to a process for preparing optically active 2-amino-, 2-chloro-, 2-hydroxy- or 2-alkoxy-1-alcohols by catalytically hydrogenating appropriate optically active 2-amino-, 2-chloro-, 2-hydroxy- and 2-alkoxycarboxylic acids or their acid derivatives in the presence of catalysts comprising palladium and rhenium or platinum and rhenium.Type: GrantFiled: August 28, 2003Date of Patent: May 15, 2007Assignee: BASF AktiengesellschaftInventors: Rolf-Hartmuth Fischer, Nils Bottke
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Patent number: 7208642Abstract: A production process and a catalyst are provided, which can be less decreased in activity of the catalyst even when CO2, water and the like are present in the starting material and/or the reaction system, and which can produce a formic ester or a methanol at a low temperature and a low pressure. The present invention relates to a process for producing methanol, comprising reacting carbon monoxide with an alcohol in the presence of an alkali metal-type catalyst, and/or an alkaline earth metal-type catalyst to produce a formic ester, wherein a hydrogenolysis catalyst of formic ester and hydrogen are allowed to be present together in the reaction system to hydrogenate the produced formic ester and thereby obtain a methanol.Type: GrantFiled: February 23, 2001Date of Patent: April 24, 2007Assignee: Nippon Steel CorporationInventors: Kaoru Fujimoto, Noritatsu Tsubaki, Kenichiro Fujimoto
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Patent number: 7208643Abstract: The invention relates to a process for producing a fatty alcohol, including hydrogenating a fatty acid ester to prepare a crude fatty alcohol product, and distilling and refining the resulting crude fatty alcohol to prepare a fatty alcohol, further including recovering a part or the whole of distillation residues obtained in the distillation step and removing an alkali component from the distillation residues, adding the treated distillation residues to hydrogenation step or to a starting fatty acid ester feed.Type: GrantFiled: March 21, 2005Date of Patent: April 24, 2007Assignee: Kao CorporationInventors: Masanori Namba, Toru Sakamoto
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Patent number: 7183443Abstract: Process for the preparation of enantiomerically enriched amino aldehydes and amino alcohols, wherein a corresponding enantiomerically enriched amino nitrile is subjected to hydrogenation in the presence of hydrogen, a hydrogenation catalyst, preferably a Pd-catalyst and a mineral acid. For the preparation of an amino aldehyde hydrogen preferably is present at a hydrogen-pressure between 0.1 and 2 MPa, in particular between 0.5 and 1 MPa. The amino aldehyde preferably is isolated in the form of a chemically and configurationally stable derivative. For the preparation of an amino alcohol, preferably at least during part of the hydrogenation hydrogen is present at a hydrogen-pressure between 2 and 10 MPa, in particular between 4 and 6 MPa. In a preferred embodiment the hydrogen-pressure initially is between 0.5 and 2 MPa and subsequently, after most of the nitrile starting material is converted, the hydrogen pressure is increased to a value between 2 and 10 MPa.Type: GrantFiled: April 7, 2003Date of Patent: February 27, 2007Assignee: DSM IP Assets B.V.Inventors: Bernardus Henricus Nicolaas Dassen, Bernardus Kaptein, Quirinus Bernardus Broxterman
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Patent number: 7169749Abstract: Alkyl-substituted butenols having the formula (I): R1—CH2—CH?CR2—CH2OH ??(I) wherein R1 is a saturated or olefinically unsaturated alkyl or cycloalkyl group having from 4 to 16 carbon atoms and wherein R1 is optionally substituted by an alkyl, cycloalkyl, aryl or alkaryl having up to 12 carbon atoms; R2 is hydrogen or an alkyl group having from 1 to about 6 carbon atoms are produced by a process which comprises: (1) reacting an aldehyde of the formula (II): R1—CH2—CHO ??(II) wherein R1 has the same meaning as in formula (I), with the corresponding lower aldehyde to form an unsaturated aldehyde in an inert organic solvent; (2) continuously contacting an optionally calcined copper/zinc catalyst with the unsaturated aldehyde under isothermal conditions at temperatures of from about 45 to about 60° C. and under a hydrogen pressure of from 1 to about 300 bar.Type: GrantFiled: September 8, 2000Date of Patent: January 30, 2007Assignee: Kao CorporationInventors: Lothar Friesenhagen, Stephan Heck, Norbert Klein, Thomas Markert, Gerrit Pelzer, Markus Schneider
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Patent number: 7169959Abstract: Unsaturated palm oil fatty alcohols with an iodine number in the range from 65 to 85, which contain substantially unsaturated fatty alcohols and mixtures of saturated fatty alcohols of the formula (I): R1OH ??(I) in which R1 is a saturated or unsaturated, linear or branched alkyl radical having 14 to 20 carbon atoms, are obtained by (a) fractionating palm oil fatty acid methyl esters into a mainly saturated C16-distillate and a mainly unsaturated C16/18-bottom product; and (b) hydrogenating the bottom product with retention of the double bonds to give the corresponding alcohols.Type: GrantFiled: June 12, 2001Date of Patent: January 30, 2007Assignee: Cognis Deutschland GmbH & Co. KGInventors: Stephan Heck, Norbert Klein, Horst-Dieter Komp, Christiane Boehr, Norbert Huebner, Alfred Westfechtel
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Patent number: 7138552Abstract: The present invention relates to a process for preparing a C13-alcohol mixture which is suitable, in particular, as precursor for the preparation of compounds having surfactant properties and of plasticizers.Type: GrantFiled: March 25, 2003Date of Patent: November 21, 2006Assignee: OXENO Olefinchemie GmbHInventors: Alfred Kaizik, Walter Tötsch, Wilhelm Droste, Wilfried Büschken, Dirk Röttger, Klaus-Diether Wiese
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Patent number: 7126034Abstract: Disclosed is a process for hydrogenating 3-hydroxypropionic acid, or esters thereof, or mixtures of the acid and the ester, in a liquid phase, in the presence of a ruthenium catalyst, alone, or in combination with at least one or more additional metal catalyst wherein the metal is molybdenum, tungsten, titanium, zirconium, niobium, vanadium, chromium, or mixtures of the metals.Type: GrantFiled: October 30, 2003Date of Patent: October 24, 2006Assignee: Cargill, IncorporatedInventors: Xiangsheng Meng, Timothy W. Abraham, Paraskevas Tsobanakis
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Patent number: 7119237Abstract: Alcohols prepared by reacting carboxylic acids and/or carboxylic esters with hydrogen in the presence of a special catalyst.Type: GrantFiled: February 19, 2003Date of Patent: October 10, 2006Assignee: Bayer AktiengesellschaftInventors: Thomas Prinz, Jürgen Kintrup, Andreas Schulze Tilling, Jörg-Dietrich Jentsch, Gerald John, Hans-Jürgen Grob, Guido Giffels
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Patent number: 7098369Abstract: A process for producing primary alcohols from secondary alcohols and/or tertiary alcohols and/or ketones, wherein the process comprises reacting a compound selected from a secondary alcohol, a tertiary alcohol, a ketone, or mixtures thereof, with carbon monoxide and hydrogen in the presence of a catalyst based on: (i) a source of Group VIII metal, (ii) a bidentate ligand having the general formula (I): R1R2M1-R-M2R3R4??(I) wherein M1 and M2 are independently P, As or Sb; R1 and R2 together represent a bivalent substituted or unsubstituted cyclic aliphatic group whereby the two free valencies are linked to M1; R3 and R4 independently represent a substituted or unsubstituted hydrocarbyl group, or together represent a bivalent or non-substituted cyclic group whereby the two free valencies are linked to M2; and R represents a bivalent aliphatic bridging group; and (iii) an acid having a pKa of 3 or less which is in excess over the Group VIII metal.Type: GrantFiled: September 24, 2003Date of Patent: August 29, 2006Assignee: Shell Oil CompanyInventors: Eit Drent, Renata Helena Van Der Made
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Patent number: 7084313Abstract: Processes for separating supercritical or near-critical mixtures containing hydrogen, a solvent gas, methanol and a fatty alcohol under an initial pressure of from 100 to 300 bar are described, wherein the processes comprise: (a) reducing the pressure of such a mixture in a first stage to a pressure of from 50 to 150 bar to form a first recycle gas and a first partially-separated intermediate mixture, wherein the reduced pressure in the first stage is at least below the initial pressure; (b) reducing the pressure of the first partially-separated intermediate mixture in a second stage to a pressure of from 10 to 50 bar to form a second recycle gas and a second partially-separated intermediate mixture; and (c) reducing the pressure of the second partially-separated intermediate mixture in a third stage to a pressure of from 1 to 10 bar to form a third recycle gas and a fatty alcohol product.Type: GrantFiled: April 2, 2003Date of Patent: August 1, 2006Assignee: Cognis Deutschland GmbH & Co. KGInventors: Bernhard Gutsche, Wilhelm Johannisbauer, Harald Roessler, Magnus Topphoff
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Patent number: 7084312Abstract: A process for the hydrogenation of an organic compound containing at least one carbonyl group comprises bringing the organic compound in the presence of hydrogen into contact with a shaped body which can be produced by a process in which (i) an oxidic material comprising copper oxide, zinc oxide and aluminum oxide is made available, (ii) pulverulent metallic copper or pulverulent cement or a mixture thereof is added to the oxidic material, and (iii) the mixture resulting from (ii) is shaped to form a shaped body.Type: GrantFiled: August 22, 2000Date of Patent: August 1, 2006Assignee: BASF AktiengesellschaftInventors: Sylvia Huber, Michael Jolyon Sprague, Boris Breitscheidel, Joachim Wulff-Döring, Michael Hesse, Rolf Pinkos, Shelue Liang, Otto Kumberger, Marc Walter
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Patent number: 7049446Abstract: The invention relates to processes for converting amino acids and amides to desirable conversion products including pyrrolidines, pyrrolidinones, and other N-substituted products. L-glutamic acid and L-pyroglutamic acid provide general reaction pathways to numerous and valuable selective conversion products with varied potential industrial uses.Type: GrantFiled: May 6, 2004Date of Patent: May 23, 2006Assignee: Battelle Memorial InstituteInventor: Jonathan E. Holladay
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Patent number: 6982340Abstract: There is provided a process wherein a lower alkyl ester of a fatty acid derived from natural fats and oils and a lower alcohol containing 1 to 4 carbon atoms is produced in a lower sulfur content at lower costs without causing a reduction in yield and a deterioration in selectivity, as well as a process for producing an alcohol without reducing the activity of a catalyst. The process comprises the step of adsorption treatment of an ester with at least one adsorbent selected from clay and activated carbon. Further are provided a process for producing an ester which further comprises adsorption treatment with a hydrogenating decomposition-type adsorbent containing Ni and/or Cu, in hydrogen or a mixed gas atmosphere of hydrogen and an inert gas, and a process for producing an alcohol which comprises hydrogenation reaction with an ester produced by any one of these processes as the starting material.Type: GrantFiled: March 11, 2003Date of Patent: January 3, 2006Assignee: Kao CorporationInventors: Taku Mumura, Hidetoshi Kadowaki, Futoshi Nishigaki
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Patent number: 6916457Abstract: A non-chrome, copper-containing catalyst, Cu—Al—O and method of preparing the same are provided wherein the Cu—Al—O catalyst is prepared by the co-precipitation of copper nitrate (Cu(NO3)2) and sodium aluminate (Na2Al2O4) solutions using sodium carbonate (Na2CO3) as a precipitant. The precipitate is filtered, washed to removed excess sodium, and dried. The dried product, to be used in a powder form, is calcined at a preferred temperature of approximately 700° to 900° C. for approximately 1 to 4 hours. The dry powder, to be tableted or extruded, is calcined at a temperature of approximately 400° to 700° C. The activity of the Cu—Al—O catalyst can be promoted in hydrogenolysis applications by the addition of various agents. The Cu—Al—O catalyst can be employed in applications in place of Cu/Cr, or other copper based catalysts.Type: GrantFiled: July 16, 2002Date of Patent: July 12, 2005Assignee: Engelhard CorporationInventor: Jianping Chen
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Patent number: 6916964Abstract: The present invention relates to a continuous process for the selective hydrogenation of olefinically unsaturated carbonyl compounds to give unsaturated alcohols in particular of citral to give a mixture of geraniol and nerol, in a reactor containing a liquid phase, in which at least one catalyst is suspended, and which can additionally contain a gas phase, wherein the liquid phase and, if present, the gas phase are passed through a device in the reactor having openings or channels.Type: GrantFiled: December 4, 2002Date of Patent: July 12, 2005Assignee: BASF AGInventors: Hans-Georg Göbbel, Till Gerlach, Frank Funke, Klaus Ebel, Signe Unverricht, Gerd Kaibel
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Patent number: 6906228Abstract: In a process for preparing alcohols by catalytic hydrogenation of carbonyl compounds over a catalyst comprising rhenium on activated carbon, the catalyst used comprises rhenium (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5, platinum (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5 and, if appropriate, at least one further metal selected from among Zn, Cu, Ag, Au, Ni, Fe, Ru, Mn, Cr, Mo, W and V in a weight ratio to the activated carbon of from 0 to 0.25, and the activated carbon has been nonoxidatively pretreated It is also possible to prepare ethers and lactones if the hydrogen pressure is not more than 25 bar. In this case, the activated carbon in the catalyst may also have been nonoxidatively pretreated.Type: GrantFiled: March 1, 2001Date of Patent: June 14, 2005Assignee: BASF AGInventors: Rolf Hartmuth Fischer, Rolf Pinkos, Stephan Andreas Schunk, Joachim Wulff-Döring, Frank Stein, Thomas Nöbel, Sylvia Huber
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Patent number: 6878665Abstract: The invention relates to novel diphosphines, in optically pure or racemic form, of formula (I): in which: R1 and R2 are a (C5-C7)cycloalkyl group, an optionally substituted phenyl group or a 5-membered heteroaryl group; and A is (CH2—CH2) or CF2. The invention further relates to the use of a compound of formula (I) as a ligand for the preparation of a metal complex useful as a chiral catalyst in asymmetric catalysis, and to the chiral metal catalysts comprising at least one ligand of formula (I).Type: GrantFiled: September 16, 2002Date of Patent: April 12, 2005Assignee: SynkemInventors: Sébastien Duprat de Paule, Nicolas Champion, Virginie Vidal, Jean-Pierre Genet, Philippe Dellis
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Patent number: 6878852Abstract: A process for the hydrogenation, using molecular hydrogen (H2) of a catalytic system, wherein the catalytic system includes a base and a complex of formula (II): Ru(P2N2)Y2??(II) wherein Y represent simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, and P2N2 is a tetradentate diimino-diphosphine ligand.Type: GrantFiled: November 11, 2001Date of Patent: April 12, 2005Assignee: Firmenich SAInventors: Valentin Rautenstrauch, Raphaël Churlaud, Robert Harold Morris, Kamaluddin Abdur-Rashid
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Patent number: 6855851Abstract: The present invention relates to a process for producing aliphatic C3-C10-alcohols, in particular 2-ethylhexanol, from high boilers by thermal treatment in the presence of an alkali metal compound and subsequent hydrogenation of the volatile products.Type: GrantFiled: October 30, 2003Date of Patent: February 15, 2005Assignee: Celanese Chemicals Europe GmbHInventors: Wolfgang Zgorzelski, Wilhelm Glick
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Patent number: 6841499Abstract: A supported catalyst comprises a cationic rhodium(I) complex of the formula wherein R1 and R2 are the same or different hydrocarbon groups of up to 30 C atoms, or R1 and R2 are linked to form a ring, and a heterogeneous support medium that provides anionic binding sites. Such a complex is particularly useful as a catalyst in a process of hydrogenating an aldehyde to produce the corresponding primary alcohol.Type: GrantFiled: October 6, 2000Date of Patent: January 11, 2005Assignee: Chirotech Technology LimitedInventors: Mark Joseph Burk, Arne Gerlach