Sulfur Containing Catalyst Utilized Patents (Class 568/899)
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Patent number: 5011506Abstract: A method is disclosed combining the process for the hydration or etherification of light linear olefins, such as the production of diisopropyl ether (DIPE), with the process for the etherification of C.sub.4 + or C.sub.4 hydrocarbons containing isobutylene to produce alkyl tertiary butyl ether or ether-rich gasoline in a manner which effectively dewaters alkanol using the iso-olefin hydrocarbon feedstream as extractant. The combined process leads to the production of isopropyl tert-alkyl ethers. In the integrated process the high octane ethers produced may include methyl tert-butyl ether, methyl tert-amyl ether, isopropyl tert-butyl ether and diisopropyl ether. The process also results in the production of a gasoline stream rich in high octane ethers.Type: GrantFiled: September 29, 1989Date of Patent: April 30, 1991Assignee: Mobil Oil CorporationInventors: Mohsen N. Harandi, Hartley Owen
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Patent number: 4990692Abstract: Cyclohexanol is removed from aqueous solutions containing it and aromatic sulfonic acids by extraction with one or more cyclohexyl ethers liquid under extraction conditions and having the formula ##STR1## where R is alkyl of from 1 to 16 catbon atoms, cycloalkyl of from 5 to 8 carbon atoms, aralkyl of from 7 to 10 carbon atoms or phenyl, which may additionally have substituents which are inert under reaction conditions.Type: GrantFiled: July 21, 1989Date of Patent: February 5, 1991Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Gosch, Rolf Fischer
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Patent number: 4982022Abstract: A process for the production of tertiary alcohols by the reaction of the corresponding isoolefin and water is disclosed. In particular the production of tertiary butyl alcohol and tertiary amyl alcohol is disclosed. The isoolefin and water are contacted over an acid cation exchange resin catalyst in a distillation column reactor where the products and reactants are separated by fractional distillation. In one embodiment a liquid level is maintained in the catalyst bed.Type: GrantFiled: August 28, 1989Date of Patent: January 1, 1991Assignee: Chemical Research & Licensing CompanyInventors: Lawrence A. Smith, Jr., Robert P. Arganbright
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Patent number: 4960961Abstract: Tert.-Amyl alcohol (TAA) can be prepared in an advantageous manner by hydrating of i-amylenes on an acid cation exchanger by carrying out the reaction in the vicinity of the boiling point of the i-amylenes under the appropriate reaction pressure. A higher content of TAA is thereby obtained in the reaction mixture.Type: GrantFiled: January 6, 1989Date of Patent: October 2, 1990Assignee: EC Erdolchemie GmbHInventors: Bernhard Schleppinghoff, Reiner Malessa, Christian Gabel, Hans-Volker Scheef, Mathias Lux
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Patent number: 4956506Abstract: A gas containing water vapor and a minor amount of ethylene and/or propylene is passed through several reactors in series containing a perfluorinated ion-exchange polymer catalyst to convert olefins to alcohols, and alcohol product is recovered from the effluent gases from each reactor.Type: GrantFiled: December 21, 1989Date of Patent: September 11, 1990Assignee: Conoco Inc.Inventor: Edward G. Latimer
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Patent number: 4954660Abstract: Linear olefins are converted into the corresponding secondary alcohols by treatment with methyl alcohol and a tertiary alcohol, in the presence of an acidic catalyst, at a temperature ranging from 120.degree. to 200.degree. C. The product mixture substantially consists of the desired secondary alcohol and of the methyl ether of the charged tertiary alcohol.The reaction products can be easily isolated by fractionation, or, in some instances, the liquid product mixture can be used as such.Of particular interest is the direct hydration of n-butenes using tert-butyl alcohol as the tertiary alcohol. The obtained product mixture can be used as such, as an additive to methanol-containing gasolines for internal combustion engines.Type: GrantFiled: October 28, 1988Date of Patent: September 4, 1990Assignee: Enichem Anic S.p.A.Inventors: Giuseppe Messina, Carmelo Nurra, Oscar Cappellazzo, Angelo Virdis, Loreno Lorenzoni
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Patent number: 4861923Abstract: A process for the hydration of lower olefins to a corresponding alcohol by reacting the olefins with water in the presence of a solid perfluorinated sulfonic superacid catalyst.Type: GrantFiled: September 7, 1984Date of Patent: August 29, 1989Assignee: PCUK Products Chimiques Uqine KuhlmannInventor: George A. Olah
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Patent number: 4849551Abstract: An industrially excellent method for separating cyclohexanol which comprises carrying out the hydration of cyclohexane in the presence of an acid, and bringing the reaction solution into contact with a mixed solution of a hydrocarbon and phenol to extraction-separate cyclohexanol from the reaction solution.Type: GrantFiled: March 24, 1988Date of Patent: July 18, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Tamio Shirafuji, Itaru Kawata
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Patent number: 4849550Abstract: A industrially excellent method for producing a cycloalkanol by the hydration of a cycloalkene having from 4 to 8 carbon atoms with an aromatic sulfonic acid as a catalyst which comprises carrying out said hydration in the presence of a phenol.Type: GrantFiled: March 24, 1988Date of Patent: July 18, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Tamio Shirafuji, Itaru Kawata
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Patent number: 4831197Abstract: An improved process for the production of lower aliphatic alcohols by the catalytic hydration of a lower aliphatic olefin in the presence of a strongly acidic cation exchange resin catalyst in a fixed bed reactor and in which a cationic surfactant has been added to the process water is provided.Type: GrantFiled: September 2, 1987Date of Patent: May 16, 1989Assignee: Deutsche Texaco AktiengesellschaftInventors: Friedrich Henn, Wilhelm Neier, Gunter Strehlke, Werner Webers
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Patent number: 4760202Abstract: Tertiary alcohols with 4 or 5 carbon atoms are produced by reacting an isoolefin-containing hydrocarbon stream with water in the presence of a strongly acidic, solid hydration catalyst in such a way that each of the two process streams, the hydrocarbon stream and the process water, is cascaded through several reactors connected in series such that one process stream is fed to one end of the line of reactors and the other process stream to the other end of the line of reactors, and the two process streams pass through the line of reactors in opposite directions, while they pass through the individual reactors as parallel currents.Type: GrantFiled: August 18, 1987Date of Patent: July 26, 1988Assignee: Deutsche Texaco AktiengesellschaftInventors: Michael Dettmer, Gunther Osterburg, Milan Prezelj, Werner Webers
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Patent number: 4760203Abstract: A direct hydration process for the production of isopropyl alcohol by reacting a propene-containing hydrocarbon stream with an aqueous stream in an interconnected series of reactors in the presence of an acidic cation exchange resin catalyst wherein the improvement comprises charging a propene-containing hydrocarbon stream to one end of a series of interconnected reactors and charging an aqueous stream to the opposite end of a series of interconnected reactors and directing the streams through the series of reactors so that the hydrocarbon stream and the aqueous stream flow in opposite directions with respect to the series of interconnected reactors and flow in parallel streams through each individual reactor is provided.Type: GrantFiled: August 18, 1987Date of Patent: July 26, 1988Assignee: Deutsche Texaco AktiengesellschaftInventors: Rolf-Rainer Carls, Gunther Osterburg, Milan Prezelj, Werner Webers
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Patent number: 4731489Abstract: A process for producing a gasoline blending stock of methyl tertiary butyl ether and tertiary butyl alcohol wherein a first catalytic etherification of isobutene and methanol produces methyl tertiary butyl ether and unreacted methanol. The etherification product including isobutene and remaining methanol is reacted with water and fresh isobutene in a second catalytic reaction where both etherification and hydration occur. This essentially exhausts the methanol while the hydration reaction to tertiary butyl alcohol prevents undesired side reactions.Type: GrantFiled: July 18, 1986Date of Patent: March 15, 1988Assignee: Conoco Inc.Inventors: David E. Whisenhunt, Gregg L. Byers, Uday S. Hattiangadi
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Patent number: 4670612Abstract: A method for producing alicyclic alcohols by the hydration of olefins in the presence of an aromatic sulfonic acid, which comprises incorporating molybdic acid or its salt and/or vanadium oxide, vanadic acid or its salt in the reaction system. The alicyclic alcohols are useful as intermediates for caprolactam, adipic acid, insecticides, etc.Type: GrantFiled: June 2, 1986Date of Patent: June 2, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Tamio Shirafuji, Kiyomi Sakai, Itaru Kawata
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Patent number: 4645863Abstract: Process for the preparation of unsaturated alcohols and/or esters thereof by reacting conjugated dienes with water and/or aqueous carboxylic acid solutions in the presence of a macroporous acid ion exchanger and suitable solvents. The diene has the general formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are hydrogen or a methyl group and R.sup.2 also can represent an aliphatic hydrocarbon radical having 2 to 6 carbon atoms which may contain a double bond which is not in a conjugated position relative to the double bonds of the diene, and preferably R.sup.1 and R.sup.3 each represent groups CH.sub.3 or CH.sub.2 --CH.sub.3. Said diene is reacted in a homogeneous or quasi-homogeneous phase in the presence of said macroporous acid ion exchanger.Type: GrantFiled: January 12, 1983Date of Patent: February 24, 1987Assignee: BASF AktiengesellschaftInventors: Walter Rebafka, Helmut Nickels
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Patent number: 4629710Abstract: Heat stabilized catalyst compositions are prepared from nuclear sulfonic acid, for example, macroporous crosslinked polyvinyl aromatic compounds containing sulfonic acid groups are neutralized with a metal of Al, Fe, Zn, Cu, Ni, ions or mixtures and alkali, alkaline earth metals or ammonium ions by contacting the resin containing the sulfonic acid with aqueous solutions of the metals salts and alkali, alkaline earth metal or ammonium salts. The catalysts have at least 50% of the sulfonic acid groups neutralized with metal ions and the balance of the sulfonic acid groups neutralized with alkali, alkaline earth ions or ammonium ions.Type: GrantFiled: December 20, 1984Date of Patent: December 16, 1986Inventor: Lawrence A. Smith, Jr.
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Patent number: 4595786Abstract: A catalytic process for the hydration of cyclohexene to cyclohexanol in the presence of perfluorosulfonic acid polymer.Type: GrantFiled: November 27, 1984Date of Patent: June 17, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: Francis J. Waller
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Patent number: 4579984Abstract: A method is provided for the continuous production of isopropanol and secondary butyl alcohol by catalytically hydrating the corresponding aliphatic olefin in an elongated reaction vessel in which co-product by-product dialkyl ether is separated from the reaction product and recycled to the reaction mixture being introduced therein at a point between the olefin feed inlet and the product outlet about 5 to 30 percent of the distance before the product outlet.Type: GrantFiled: April 11, 1985Date of Patent: April 1, 1986Assignee: Deutsche Texaco AktiengesellschaftInventors: Wilhelm Neier, Werner Webers, Michael Dettmer, Gunther Osterburg
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Patent number: 4560805Abstract: An improved process is provided for forming ketones from the corresponding olefins in the vapor phase in the presence of water vapor employing a heterogeneous catalyst comprising rhenium compounds and complexes, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: December 24, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
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Patent number: 4560804Abstract: An improved process is provided for forming ketones from the corresponding olefins by vapor phase oxidation of the olefin in the presence of water vapor, and optionally in the additional presence of molecular oxygen employing a heterogeneous catalyst comprising at least one member selected from the group consisting of Ce, Nd and La and compounds and complexes thereof, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: December 24, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
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Patent number: 4551567Abstract: Ethers such as isobutyl tertiary butyl ether are dissociated into their component alcohols and isolefins by heat stabilized catalyst compositions prepared from nuclear sulfonic acid, for example, macroporous crosslinked polyvinyl aromatic compounds containing sulfonic acid groups are neutralized with a metal of Al, Fe, Zn, Cu, Ni, ions or mixtures and alkali, alkaline earth metals or ammonium ions by contacting the resin containing the sulfonic acid with aqueous solutions of the metals salts and alkali, alkaline earth metal or ammonium salts. The catalysts have at least 50% of the sulfonic acid groups neutralized with metal ions and the balance of the sulfonic acid groups neutralized with alkali, alkaline earth ions or ammonium ions.Type: GrantFiled: September 7, 1984Date of Patent: November 5, 1985Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
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Patent number: 4540831Abstract: A process is disclosed for performing an exothermic reaction such as the etherification of isobutylene with methanol. The feed is charged to a vertical reaction zone containing a solid catalyst. Heat released by the exothermic reaction partially vaporizes the reactants, with the vapors traveling upward to a condensing zone. All of the condensable vapors entering the condensing zone are condensed and returned downward to the catalyst bed. A single effluent stream made up of the product, excess reactants and any unreactive compounds present in the feed streams is removed from the bottom of the reaction zone. This total reflux reaction zone allows temperature control within a catalyst bed without the use of indirect heat exchangers located within the reaction zone.Type: GrantFiled: May 17, 1984Date of Patent: September 10, 1985Assignee: UOP Inc.Inventor: Bruce A. Briggs
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Patent number: 4528401Abstract: An improved process is provided for forming ketones from the corresponding olefins in the vapor phase in the presence of water vapor employing a heterogeneous catalyst comprising a molybdenum disulfide catalyst formed by the thermal decomposition of a thiomolybdate compound. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: July 9, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
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Patent number: 4507512Abstract: An improved process for producing an alcohol by hydrating an olefin wherein the improvement comprises hydrating an olefin in the presence of a hydrogen-type catalyst having a silica/alumina molar ratio of 20 to 500 and a solvent using either:A. hydrogen-type mordenite or hydrogen-type zeolite Y, and a sulfone; orB. hydrogen-type crystalline aluminosilicate in which the entrance of the main void is formed by a 10-membered or 12-membered oxygen ring, and a C.sub.2 to C.sub.5 oxy acid or the lactones, lactides, methyl or ethyl esters thereof.Type: GrantFiled: May 14, 1984Date of Patent: March 26, 1985Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshiharu Okumura, Setsuo Kamiyama, Hiroshi Furukawa, Katsumi Kaneko
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Patent number: 4484013Abstract: A process is disclosed for the production of isopropanol and tertiary butyl alcohol from C.sub.3 and C.sub.4 hydrocarbons. The preferred embodiment of the invention comprises dehydrogenation of paraffins and direct hydration of the resulting olefins. Fractional distillation steps are employed between the dehydrogenation and dehydration zones and in the recycle stream to recover unconverted hydrocarbons leaving the hydration zone. This accommodates different hydration rates and prevents the passage of propylene into the dehydrogenation zone. In an alternative embodiment, the feed stream comprises olefins and is fed to the fractionation system. The dehydrogenation zone may be deleted from this embodiment.Type: GrantFiled: December 30, 1983Date of Patent: November 20, 1984Assignee: UOP Inc.Inventor: Robert J. Schmidt
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Patent number: 4482767Abstract: A hydrocarbon conversion process is disclosed for the production of lower alcohols and LPG from a mixture of C.sub.3 -minus paraffins and olefins. The feed stream is passed into a hydration zone wherein portions of the ethylene and propylene are converted to ethanol and propanol. The hydrocarbons which are not hydrated are passed into a hydrogenation zone wherein the remaining olefins are converted to paraffins. The feed stream is preferably a hydrogen-containing C.sub.1 to C.sub.3 cut separated from the effluent of a fluidized catalytic cracking unit.Type: GrantFiled: December 20, 1983Date of Patent: November 13, 1984Assignee: UOP Inc.Inventor: Tamotsu Imai
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Patent number: 4476333Abstract: A process for the production of secondary butyl alcohol by the direct hydration of n-butenes in the presence of an acidic cation exchange resin catalyst which comprises depressurizing the vaporous product stream from a reactor to a pressure ranging from 15 to 40 bar and cooling the depressurizing product stream to a temperature of 120.degree. C. or below to liquefy the product stream, separating an aqueous fraction from said stream leaving an alcohol-butene/butane organic mixture, vaporizing said organic mixture, depressurizing said organic mixture to a pressure ranging from 3 to 30 bar and including a pressure of from 3 to 8 bar and introducing said depressurized organic mixture into a separation column to separate secondary butyl alcohol from said mixture.Type: GrantFiled: January 27, 1983Date of Patent: October 9, 1984Assignee: Deutsche Texaco AktiengesellschaftInventors: Wilhelm Neier, Werner Webers, Rainer Ruckhaber, Gunther Osterburg, Wolf J. Ostwald
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Patent number: 4469903Abstract: A process is disclosed for the production of aliphatic alcohol by the direct hydration of an olefinic hydrocarbon. The process is directed to the production of isopropyl alcohol. The process includes the recovery of the alcohol from a water-rich hydration zone effluent stream by countercurrent liquid-liquid extraction against a paraffinic solvent. The solvent is derived from paraffins originally admixed with the olefin-containing feed stream, and the raffinate stream comprises water which is recycled in the process. Expensive product fractionation is eliminated in the production of a fuel grade isopropyl alcohol.Type: GrantFiled: September 21, 1983Date of Patent: September 4, 1984Assignee: UOP Inc.Inventor: Robert J. Schmidt
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Patent number: 4469905Abstract: A process for producing and recovering a C.sub.2 to C.sub.6 alcohol, which comprises contacting water and a C.sub.2 to C.sub.6 olefin with a hydration catalyst comprising an acidic ion exchange resin in a reaction zone under reaction conditions, said reaction zone containing multiple water quench points and multiple olefin injection points, and counter-currently contacting the reaction product with a solvent to extract the C.sub.2 to C.sub.6 alcohols therefrom.Type: GrantFiled: November 4, 1981Date of Patent: September 4, 1984Assignee: Union Oil Company of CaliforniaInventors: Texas V. Inwood, Carlyle G. Wight, Jeffery W. Koepke
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Patent number: 4456776Abstract: A process for continuously producing a lower aliphatic alcohol by the direct hydration of a lower aliphatic olefin having from 3 to 5 carbon atoms in the presence of a strongly acidic cation exchange resin catalyst the improvement which comprises presaturating the olefin feed with from about 0.3 to 1.8 weight percent of water prior to introducing the olefin feed into the reactor.Type: GrantFiled: January 13, 1983Date of Patent: June 26, 1984Assignee: Deutsche Texaco AktiengesellschaftInventors: Wilhelm Neier, Werner Webers, Wolf Ostwald
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Patent number: 4424388Abstract: A low temperature, low pressure process for the production of alcohol by the hydration of olefins. The olefin is contacted with a sulfonated ion-exchange resin in the presence of water and glycol diethyl solvent to hydrate said olefin, preferably propylene, and form from the olefin the corresponding aliphatic, monohydric alcohol. The solvent, a key and novel feature of the invention, at reaction conditions forms two liquid phases, a glycol diether phase and a water phase. The alcohol forms predominanty in the glycol diether phase and to a lesser extent in the water phase, with the products, inclusive of by product either, being distributed between the two phases. The glycol diethyl phase effectively displaces the equilibrium toward higher alcohol production, and the ether by product suppresses the equilibrium and minimizes formation of the ether product.Type: GrantFiled: June 25, 1982Date of Patent: January 3, 1984Assignee: ImprotecInventors: David G. Braithwaite, deceased, Joe D. Pickle
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Patent number: 4423251Abstract: A hydrocarbon conversion process is disclosed which may be used to produce high purity isobutylene and/or tertiary butyl alcohol and methyl tertiary butyl ether. A mixed C.sub.4 feed stream is divided into two portions with a first portion being passed through a hydration zone to produce the tertiary butyl alcohol. The remaining hydrocarbons withdrawn from the hydration zone and the second portion of the feed stream are changed to an etherification zone. The unconverted hydrocarbons exiting the etherification zone may be subjected to isomerization and/or dehydrogenation to produce additional isobutylene. The high purity isobutylene is obtained by dehydrating the tertiary butyl alcohol.Type: GrantFiled: September 9, 1982Date of Patent: December 27, 1983Assignee: UOP Inc.Inventors: Peter R. Pujado, Bipin V. Vora
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Patent number: 4406760Abstract: An improved process is provided for treating spent sulfuric acid streams formed in the catalytic hydration of olefins to prepare alcohols, wherein the spent acid stream containing organo-sulfonic acid impurities is treated in an electrolysis zone under conditions sufficient to electrolytically oxidize at least a portion of said organo-sulfonic acid impurities to form partially oxidized organic compounds therefrom and thereby provide a treated sulfuric acid stream of increased thermal stability. The improved process permits continuous operation at levels of total organic carbon in the treated acid which would otherwise be unacceptable and minimizes the substantial operating problems associated with formation of heavy carbon deposits in the process equipment.Type: GrantFiled: November 25, 1981Date of Patent: September 27, 1983Assignee: Exxon Research & Engineering Co.Inventors: George A. Knudsen, Charles Savini
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Patent number: 4405822Abstract: A process for producing alcohols by the direct hydration of olefins in which the ether by-product is hydrated with a large molar excess of water in a reaction zone which precedes a propylene hydration reaction zone.Type: GrantFiled: October 30, 1981Date of Patent: September 20, 1983Assignee: Chevron Research CompanyInventor: Susan A. Bezman
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Patent number: 4358626Abstract: Secondary alcohols are produced by the hydration of a n-olefin substantially free from an isoolefin in the presence as catalyst of an acidic cation exchange resin such as a sulfonated styrene-divinylbenzene copolymer and in the presence of an oxy acid or lactone thereof such as .gamma.-valerolactone. The process is especially useful for hydrating a n-butene feed or a feed consisting essentially of n-butenes and butane to produce secondary butyl alcohol.Type: GrantFiled: August 6, 1981Date of Patent: November 9, 1982Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshiharu Okumura, Tadamori Sakakibara, Katsumi Kaneko
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Patent number: 4357479Abstract: The production of alcohols in which an olefinic hydrocarbon is hydrated with a liquid water in the presence of an aqueous sulfur-containing acid catalyst such as sulfuric acid may be improved by effecting the reaction in the presence of a solid, porous carbon support which will act as the co-catalyst or promoter. The hydration reactions which are employed for the process will include a temperature in the range of from about 100.degree. to about 300.degree. C. and a pressure in the range of from about 1 to about 300 atmospheres.Type: GrantFiled: October 5, 1981Date of Patent: November 2, 1982Assignee: UOP Inc.Inventor: Tamotsu Imai
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Patent number: 4357147Abstract: A process for the production of an oxygenated fuel blending composition which contains isopropanol by the hydration of propylene in which the by-product diisopropyl ether is subjected to a reversion reaction and the resulting propylene is oligomerized to form olefinic gasoline.Type: GrantFiled: October 30, 1981Date of Patent: November 2, 1982Assignee: Chevron Research CompanyInventor: Susan A. Bezman
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Patent number: 4356126Abstract: Process for the carbonylation of alkanols and/or ethers at elevated temperature and pressure in the presence of a Group VIII metal compound and pentachlorobenzenethiol and/or salts thereof, using a pentachlorobenzenethiol compound: Group VIII metal compound molar ratio of not more than 10. The process is of special interest for the production of methyl acetate from methanol using an active, iodine-free catalytic system.Type: GrantFiled: June 17, 1981Date of Patent: October 26, 1982Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4352945Abstract: A process for the production of isopropanol by the hydration of propylene in which the by-product diisopropyl ether is subjected to a reversion reaction and the resulting propylene is recycled to the hydration stage.Type: GrantFiled: October 30, 1981Date of Patent: October 5, 1982Assignee: Chevron Research CompanyInventor: Susan A. Bezman
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Patent number: 4351970Abstract: A method is disclosed of preparing alcohols having 2 to 4 carbon atoms by catalytic hydration of the corresponding olefins on acid catalysts at elevated temperature and elevated pressure, characterized in that byproducts of the hydration, namely corresponding ethers and/or low-polymerized hydrocarbons and/or undesired alcohols, which form upon the passage of the input product through catalyst bed, are fed to the input product before entry into the reactor, said method being characterized in that:A. When ethylene is the olefin, the reaction is conducted at a temperature of 200.degree.-300.degree. C.; andB: When propylene is the olefin the reaction is conducted at a temperature of 150.degree. to 220.degree. C.Type: GrantFiled: May 21, 1980Date of Patent: September 28, 1982Assignee: Veba-Chemie AktiengesellschaftInventors: August Sommer, Wilhelm Heitmann, Rainer Brucker
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Patent number: 4340769Abstract: A method is provided for the continuous production of saturated aliphatic alcohols having from 2 to 5 carbon atoms by hydrating the corresponding aliphatic olefin in the presence of a sulfonated styrene-divinylbenzene copolymer catalyst having a specific surface area measured in the dry state employing the BET method of:(a) less than 1 m.sup.2 /g if the water-wet resin is dried, and(b) greater than 1 m.sup.2 /g if the water is displaced from the water-wet resin by a slightly polar or a nonpolar organic solvent and the so dewatered resin is dried.Type: GrantFiled: September 25, 1978Date of Patent: July 20, 1982Assignee: Deutsche Texaco AktiengesellschaftInventors: Gunter Brandes, Wilhelm Neier, Johannes Wollner, Werner Webers, Walter F. deVleesschauwer
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Patent number: 4339617Abstract: Olefinic hydrocarbons may be hydrated to form corresponding alcohols by treating said olefins with water in the presence of an acidic compound which acts as a catalyst, said hydration reaction being effected at a temperature in the range of from about 100.degree. to about 300.degree. C. and a pressure in the range of from about 1 to about 100 atmospheres. In addition, the reaction medium also contains a salt of a metal selected from the group consisting of magnesium, barium, beryllium and radium, said metal salts suppressing the corrosive nature of the acid catalyst and thus permitting the reaction to be effected in normal metal reactors.Type: GrantFiled: March 9, 1981Date of Patent: July 13, 1982Assignee: UOP Inc.Inventors: Tamotsu Imai, Robert J. Schmidt
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Patent number: 4334890Abstract: A gasoline blending stock is produced by the simultaneous reaction of a hydrocarbon feed containing at least one tertiary olefin, at least one aliphatic alcohol, and water over a suitable catalyst. In a typical embodiment, a mixed C.sub.4 stream containing isobutylene is reacted with aqueous ethanol to form a mixture of ethyl tertiary butyl ether and tertiary butanol, with minimal formation of secondary alcohols from any normal butenes present in the hydrocarbon feed.Type: GrantFiled: February 3, 1981Date of Patent: June 15, 1982Assignee: The Halcon SD Group, Inc.Inventors: Nand K. Kochar, Richard L. Marcell
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Patent number: 4327231Abstract: Tertiary alcohols are produced by the hydration of an isoolefin in the presence as catalyst of an acidic cation exchange resin such as a sulfonated styrene-divinylbenzene copolymer, and a polyhydric neo-type alcohol such as neopentyl glycol. The process is useful for separating isobutylene from a hydrocarbon mixture containing its isomers via preparation of the alcohol, separation from the unreacted hydrocarbons and dehydration of the tertiary butyl alcohol to isobutylene.Type: GrantFiled: March 3, 1980Date of Patent: April 27, 1982Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshiharu Okumura, Hiroshi Furukawa, Katsumi Kaneko
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Patent number: 4307257Abstract: An aqueous high concentration solution of tert-butyl alcohol can be produced with high conversion and high selectivity by using a material composition having special proportions of tert-butyl alcohol, water and isobutylene or an isobutylene-containing hydrocarbon mixture and reacting isobutylene with water in the presence of a cation exchange resin having sulfonic acid groups preferably in multi-stage reactors and separating inert hydrocarbons and unreacted isobutylene from the reaction solution in a distillation column.Type: GrantFiled: June 23, 1980Date of Patent: December 22, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Masao Sada, Michio Kato, Yoshihide Mori, Michikazu Sano
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Patent number: 4306101Abstract: A process is disclosed for hydrating olefins to alcohols using a very active catalyst comprising an alpha-hydroxysulfonic acid prepared by reacting a carbonyl compound with sulfur dioxide and water.Type: GrantFiled: November 5, 1980Date of Patent: December 15, 1981Assignee: Shell Oil CompanyInventors: Lynn H. Slaugh, Carl L. Willis
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Patent number: 4284831Abstract: Tertiary alcohols are produced by the hydration of an isoolefin in the presence as catalyst of an acidic cation exchange resin such as a sulfonated styrene-divinylbenzene copolymer and in the presence of an oxy acid or lactone thereof such as .gamma.-valerolactone. The process is useful for separating isobutylene from a hydrocarbon mixture containing its isomers via preparation of the alcohol, separation from the unreacted hydrocarbons and dehydration of the tertiary butyl alcohol to isobutylene.Type: GrantFiled: May 5, 1980Date of Patent: August 18, 1981Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshiharu Okumura, Katsumi Kaneko
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Patent number: 4281206Abstract: Trickle-type fixed-bed catalytic reactions are improved, prior to starting or resuming an on-stream period, by purging air from the catalyst bed and reaction zone by downward flow of an inert gas therethrough, flooding the purged reaction zone by flowing a liquid upwardly through the catalyst bed to cover same, then removing the liquid and instituting the on-stream period by introducing gaseous and liquid reactants at the upper end of the catalyst bed to flow downwardly therethrough.Type: GrantFiled: January 30, 1975Date of Patent: July 28, 1981Assignee: Deutsche Texaco AktiengesellschaftInventors: Gunter Brandes, Johannes Wollner, Wilhelm Neier, Werner Webers
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Patent number: 4270011Abstract: Isobutylene in a C.sub.4 hydrocarbon mixture with n-butenes and butanes is selectively hydrated to tertiary butyl alcohol by carrying out the reaction with water at a temperature not above 100.degree. C. in the presence of an acidic cation exchange resin and a sulfone.Type: GrantFiled: June 9, 1980Date of Patent: May 26, 1981Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshiharu Okumura, Katsumi Kaneko
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Patent number: 4267397Abstract: Olefinic compounds, and particularly olefinic hydrocarbons, containing from 2 to about 4 carbon atoms may be subjected to a direct hydration process utilizing a dilute aqueous sulfuric acid to treat the olefin at reaction conditions which will include a temperature in the range of from about 100.degree. to about 300.degree. C. and a pressure in the range of from about 1 to about 250 atmospheres. In addition, if so desired, a transition metal sulfate may also be present in the reaction mixture.Type: GrantFiled: December 21, 1979Date of Patent: May 12, 1981Assignee: UOP Inc.Inventors: Robert J. Schmidt, Tamotsu Imai