Using S-containing Catalyst Patents (Class 585/515)
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Patent number: 5124299Abstract: Improved processes for acid-catalyzed oligomerization of olefins and alkylation of toluene are disclosed using a catalyst blend of at least one perfluorinated ion-exchange polymer containing sulfonic acid groups and at least one polymer diluent in a nonpolar reaction mixture.Type: GrantFiled: November 15, 1991Date of Patent: June 23, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Francis J. Waller
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Patent number: 5113034Abstract: A solid, acid catalyst, supported or unsupported, comprised of an anion modified Group IVB oxide is used to dimerize C.sub.3 or C.sub.4 containing feedstreams.Type: GrantFiled: August 5, 1991Date of Patent: May 12, 1992Assignee: Exxon Research and Engineering CompanyInventors: Stuart L. Soled, Nicholas C. Dispenziere, Jr., Ramzi Y. Saleh, Sabato Miseo
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Patent number: 5105047Abstract: Improved processes for acid-catalyzed oligomerization of olefins and alkylation of toluene are disclosed using a catalyst blend of at least one perfluorinated ion-exchange polymer containing sulfonic acid groups and at least one polymer diluent in a nonpolar reaction mixture.Type: GrantFiled: August 2, 1989Date of Patent: April 14, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Francis J. Waller
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Patent number: 5094995Abstract: A catalyst composition comprising a perfluorinated ion-exchange polymer containing sulfonic acid groups supported on an inert carrier having a hydrophobic surface with a mean pore diameter of at least 1000 .ANG.. Use of this catalyst provides improved hydrocarbon conversion processes for oligomerization of olefins, hydration of olefins and hydrolysis of esters.Type: GrantFiled: August 2, 1989Date of Patent: March 10, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Martin H. D. Butt, Francis J. Waller
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Patent number: 5008466Abstract: Alkenes having a terminal double bond can be isomerized to give alkenes having an internal double bond if alkenes having a terminal double bond or hydrocarbon feedstock having a content of alkenes of this type having a terminal double bond are subjected to treatment, in the presence of hydrogen, over a macroporous or gel-like cation exchanger in the H.sup.+ form which contains 0.001 to 10 g of one or more metals of the VIth and/or VIIth and/or VIIIth sub-group of the periodic system of the elements in elementary form per liter of dry cation exchanger and which has a degree of crosslinking of 2 to 65% and a specific surface area of 5 to 750 m.sup.2 /g of dry exchange resin. The treatment is carried out in the liquid phase at a temperature from 0.degree. to 120.degree. C.Type: GrantFiled: April 12, 1989Date of Patent: April 16, 1991Assignee: EC Erdolchemie GmbHInventors: Bernhard Schleppinghoff, Hans-Dieter Kohler, Christian Gabel, Hans-Volker Scheef
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Patent number: 4973789Abstract: A process for preparing a lower alkene polymer from a lower alkene feedstream, including the steps of: (A) contacting the lower alkene monomer with a catalyst system comprising boron trifluoride and at least one acid selected from the group consisting of sulfuric acid, sulfurous acid, phosphoric acids and strong acid resins and (B) polymerizing the lower alkene monomer in the presence of the catalyst system at a temperature of about -3.degree. C. to about -30.degree. C. thereby obtaining a lower alkene polymer having a molecular weight of about 250 to about 500.Type: GrantFiled: July 30, 1987Date of Patent: November 27, 1990Assignee: The Lubrizol CorporationInventors: Jack L. Karn, Willis P. Nichols
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Patent number: 4910356Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.Type: GrantFiled: January 29, 1988Date of Patent: March 20, 1990Assignee: Union Oil Company of CaliforniaInventor: Donald C. Young
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Patent number: 4711969Abstract: A process for oligomerizing ethylene using a nickel ylide catalyst substituted with a sulfonato group, wherein the oligomerization is carried out in the presence of methanol and water.Type: GrantFiled: August 25, 1986Date of Patent: December 8, 1987Assignee: Chevron Research CompanyInventors: David L. Beach, James J. Harrison
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Patent number: 4689437Abstract: An olefin oligomerization/cooligomerization process with a catalyst comprising the reaction product of (1) a transition metal compound selected from the metals Ni, Co, Cr, Fe, Cu, (2) a catalyst activator capable of donating a hydride, alkyl, alkenyl or aryl group when the transition metal has the oxidation state of O or the transition metal compound does not have a hydride, alkyl, alkenyl or aryl group, and (3a) an organophosphorus sulfonate ligand containing one benzene ring with trivalent phosphorus P(III) group and SO.sub.3 M group at ortho-positions, or one benzene ring with CH.sub.2 --P(III) and CH.sub.2 --SO.sub.3 M groups at ortho-positions, or a bridging or fused aromatic ring system with P(III) or CH.sub.2 --P(III) group and SO.sub.3 M or CH.sub.2 --SO.sub.3 M group at adjacent positions on different rings, or any aromatic ring having the P(III) and SO.sub.3 M groups at adjacent positions, where M is H, Group IA or Group IIA metals, quarternary ammonium or phosphonium (NR.sub.4, PR.sub.Type: GrantFiled: July 21, 1986Date of Patent: August 25, 1987Assignee: Union Carbide CorporationInventor: Rex E. Murray
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Patent number: 4686315Abstract: A process for oligomerizing ethylene using a bicomponent catalyst comprising a nickel ylide substituted with a sulfonato group and an alkyl aluminum alkoxide.Type: GrantFiled: December 12, 1986Date of Patent: August 11, 1987Assignee: Chevron Research CompanyInventors: David L. Beach, Yury V. Kissin
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Patent number: 4677241Abstract: A process for oligomerization of a lower olefin having 2 to 8 carbon atoms which comprises contacting said lower olefin with a catalyst composition comprising a transition metal complex selected from complexes of nickel and palladium with a fluoro-organic thiol or sulfide ligand, having a single sulfur atom in a ligating position and wherein the carbon atom adjacent the carbon to which the sulfur atom is attached has at least one fluoro substituent and with the proviso that said fluoro-organic thiol or sulfide does not contain any other ligating group or atom in a ligating position which will displace fluoro as a ligand, and an organometallic-reducing agent selected from the group of borohydride and organoaluminum halides and alkoxides.Type: GrantFiled: August 15, 1986Date of Patent: June 30, 1987Assignee: Chevron Research CompanyInventor: Richard S. Threlkel
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Patent number: 4629818Abstract: There is provided a catalyst comprising (i) ZSM-5 or ZSM-11, (ii) gallium and (iii) thorium. Also provided is a process for converting ethylene, propylene and/or propane into aromatics with this catalyst. Modification of ZSM-5 with both Ga and Th has been found to result in greater yields of liquid and BTX from a refinery off gas stream than can be obtained with ZSM-5 modified only with Ga.Type: GrantFiled: November 4, 1985Date of Patent: December 16, 1986Assignee: Mobil Oil CorporationInventor: George T. Burress
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Patent number: 4579990Abstract: Propylene contained in mixed C.sub.3 /C.sub.4 streams containing at least 5 wt. % isobutene, for example, catalytic cracker offgas, may be recovered as a useful gasoline component by oligomerizing the propylene in liquid phase at 80.degree. to 130.degree. C. at LHSV 2 to 5 in the presence of an acidic cation exchange resin whereby the oligomers produced are primary C.sub.6 to C.sub.8 mono olefins.Type: GrantFiled: July 15, 1985Date of Patent: April 1, 1986Assignee: Tenneco Oil CompanyInventor: Donald A. Keyworth
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Patent number: 4571439Abstract: Propylene contained in mixed C.sub.3 /C.sub.4 streams containing at least 5 wt. % isobutene, for example, catalytic cracker offgas, may be recovered as a useful gasoline component by reacting in the presence of methanol to etherify and oligomerize the propylene in liquid phase at 80.degree. to 130.degree. C. at LHSV 2 to 5 in the presence of an acidic cation exchange resin whereby the product contains oligomers which are primary C.sub.6 to C.sub.8 mono olefins, methyl isopropyl ether, methyl tertiary butyl ether and unreacted material, by maintaining a residual of methanol in the product stream of 0.03 to 0.9 wt. % based on the product stream.Type: GrantFiled: July 22, 1985Date of Patent: February 18, 1986Assignee: Tenneco Oil CompanyInventor: Donald A. Keyworth
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Patent number: 4569725Abstract: A C.sub.4 -hydrocarbon mixture which essentially contains n-butenes and butanes is separated by a process in whichthe mixture is reacted with a carboxylic acid in the presence of an acidic catalyst to form a butyl carboxylate,the reaction mixture obtained from the esterification zone is distilled to give, as the top product, a fraction containing the butanes, and, as the bottom product, a fraction containing the resulting butyl carboxylate,the butyl carboxylate is decomposed at elevated temperatures to give the carboxylic acid and n-butenes, andthe mixture of n-butenes and carboxylic acid is then distilled, the n-butenes being obtained as the top product, and the carboxylic acid as the bottom product.Type: GrantFiled: May 23, 1984Date of Patent: February 11, 1986Assignee: BASF AktiengesellschaftInventors: Alfred Lindner, Klaus Broellos, Gerhard Sandrock, Klaus Volkamer, Werner Hefner
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Patent number: 4511750Abstract: An olefin oligomerization catalyst containing nickel sulfate on a porous support, activated by calcining in an oxidizing atmosphere, followed by inert gas treatment at a lower but elevated temperature, is useful for oligomerizing propylene and butenes.Type: GrantFiled: June 14, 1984Date of Patent: April 16, 1985Assignee: Chevron Research CompanyInventor: Stephen J. Miller
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Patent number: 4482775Abstract: A method for isomerizing isobutene or n-butene to produce a mixture of isobutene and normal butene, and polymerizing at least a portion thereof to produce isobutene/n-butene codimer, which comprieses feeding at least 80 weight % of either the isobutene or n-butene to a catalytic distillation reactor containing a fixed bed acidic cation exchange resin catalyst packing which provides both the catalyst sites and distillation sites for the reaction products, isomerizing a portion of the isobutene or n-butene to produce a mixture of isobutene and n-butene and reacting at least a portion of the isobutene and n-butene to form codimer of isobutene and n-butene, whereby an overhead fraction containing any unreacted isobutene and n-butene and a bottoms fraction containing codimer is produced. The result of the reaction is substantially the same regardless whether the feed is isobutene or n-butene. Other aspects of the invention, include combinations of procedures to produce high purity isobutene and n-butene.Type: GrantFiled: September 22, 1982Date of Patent: November 13, 1984Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
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Patent number: 4469911Abstract: The isobutene in C.sub.4 hydrocarbon streams containing 5 to 60 mole % isobutene and n-butenes may be reduced to a level of 0.2 mole % or less by passing the feed stream at LHSV 0.5 to 12 in liquid phase through a fixed bed cation exchange resin catalyst in a tubular reactor with a water heat exchange medium maintained at a temperature of 30.degree. to 80.degree. C., whereby the isobutene is oligomerized and easily separated from the remaining C.sub.4 by fractionation.Type: GrantFiled: November 8, 1982Date of Patent: September 4, 1984Assignee: Petro Tex Chemical CorporationInventor: Harold E. Manning
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Patent number: 4463211Abstract: A process for the oligomerization of normal C.sub.2 -C.sub.10 olefins, for example n-butenes by passing a feed containing said olefins in liquid phase through a fixed bed of acid, cation exchange resin at a temperature in the range of 40.degree. to 185.degree. C. at LHSV of 0.10 to 10 and recovering the oligomer product. In the case of n-butenes the principal component of the oligomer product is C.sub.8 dimer.Type: GrantFiled: September 27, 1982Date of Patent: July 31, 1984Assignee: Petro-Tex Chemical CorporationInventor: Harold E. Manning
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Patent number: 4447668Abstract: Alkyl tertiary butyl ether or alkyl tertiary amyl ether is dissociated by vapor phase contact with a cation acidic exchange resin at temperatures in the range of 150.degree. to 250.degree. F. at LHSV of 0.1 to 20 to produce a stream consisting of unreacted ether, isobutene or isoamylene and an alcohol corresponding to the alkyl radical. After the alcohol is removed, the ether/isoolefin stream may be fractionated to obtain a high purity isoolefin (99+%) or the ether/isoolefin stream can be contacted in liquid phase with a cation acidic exchange resin to selectively dimerize the isoolefin in a highly exothermic reaction, followed by fractionation of the dimerization product to produce high purity diisoolefin (97+%). In the case where the alkyl is C.sub.3 to C.sub.6 and the corresponding alcohol is produced on dissociation of the ether, combined dissociation-distillation may be carried out such that isoolefin is the overhead product and alcohol the bottom.Type: GrantFiled: May 25, 1983Date of Patent: May 8, 1984Assignee: Chemical Research & Licensing CompanyInventors: Lawrence A. Smith, Jr., Edward M. Jones, Jr., Dennis Hearn
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Patent number: 4382153Abstract: Ethylene is oligomerizied by reacting ethylene under an elevated pressure greater than about 700 pounds per square inch gauge (4826 kPa) in methanol in contact with a nickel ylide defined by the following Formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: April 5, 1982Date of Patent: May 3, 1983Assignee: Gulf Research & Development CompanyInventors: David L. Beach, James J. Harrison
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Patent number: 4375576Abstract: In the liquid phase reaction of isobutene in the presence of resin cation exchange resins with itself in a C.sub.4 hydrocarbon stream to form dimers, the formation of higher polymers, oligomers, and co-dimer by-products is suppressed by the presence of 0.0001 to 1 mole per mole of isobutene of methyl tertiary butyl ether.Type: GrantFiled: July 27, 1981Date of Patent: March 1, 1983Assignee: Chemical Research & Licensing Co.Inventor: Lawrence A. Smith, Jr.
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Patent number: 4367352Abstract: A process is disclosed for the production of high quality synthetic lubricants which comprises transforming ethylene into a mix of alpha olefins, separating from this mix of alpha olefins the alpha olefins in the range from about 14 to 20 carbon atoms, oligomerizing the alpha olefins in the range from about 14 to 20 atoms with a perfluorosulfonic acid resin catalyst and hydrogenating these oligomerized olefins. The olefins from the original mix of alpha olefins which are lighter and heavier than the 14 to 20 carbon atom alpha olefins processed above are combined and subjected to an isomerization/disproportionation process and the resulting olefins in the range of about 14 to 20 carbon atoms are oligomerized with perfluorosulfonic acid resin catalyst as above. Optionally, these olefins in the range of 14 to 20 carbon atoms may be combined with the olefins prepared directly from ethylene before oligomerization takes place. The resulting oligomers are hydrogenated.Type: GrantFiled: December 22, 1980Date of Patent: January 4, 1983Assignee: Texaco Inc.Inventors: Lewis W. Watts, Jr., Edward T. Marquis
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Patent number: 4356339Abstract: A process for isolating and recovering butene-1 of high purity at a high yield is provided. The process comprises the steps of continuously passing a butane-butene fraction containing 0.1 to 15 wt % of isobutylene and 10 to 50 wt % of butene-1 through a first reactor packed with a strongly acidic cation exchange resin having an average particle size of from 0.2 to 10 mm at a temperature of from 30.degree. to 100.degree. C. and at a space velocity of liquid of from 0.1 to 50 hr.sup.-1 under a pressure of from 1 to 50 atm., dividing the output mixture flowing out of said first reactor into two flows at a division ratio in flow rate of 1.about.15:1, recirculating the first flow having the flow rate of 1.about.Type: GrantFiled: December 7, 1981Date of Patent: October 26, 1982Assignee: Nippon Oil Company, LimitedInventors: Masao Imaizumi, Tetsuya Takezono, Takaaki Amari, Yutaka Oguchi
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Patent number: 4313016Abstract: The isobutene in C.sub.4 hydrocarbon streams containing from 0.5 to 5% isobutene and n-butenes is reduced preferably to a level of 0.2 mole % or less by passing the feed stream at LHSV 2.5 to 12 in liquid phase through a fixed-bed cation exchange resin catalyst in a tubular reactor with a water heat exchange medium maintained at a temperature of 50.degree. to 80.degree. C., whereby the isobutene is oligomerized and easily separated from the remaining C.sub.4 's by fractionation.Type: GrantFiled: October 23, 1980Date of Patent: January 26, 1982Assignee: Petro-Tex Chemical CorporationInventor: Harold E. Manning
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Patent number: 4310716Abstract: Ethylene is oligomerized by reacting ethylene in methanol under oligomerization conditions in contact with a nickel ylide defined by the following Formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 18, 1980Date of Patent: January 12, 1982Assignee: Gulf Research & Development CompanyInventors: David L. Beach, James J. Harrison
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Patent number: 4293727Abstract: Ethylene is oligomerized by contacting ethylene under oligomerization conditions with a nickel ylide defined by the following Formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 18, 1980Date of Patent: October 6, 1981Assignee: Gulf Research & Development CompanyInventors: David L. Beach, James J. Harrison
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Patent number: 4242530Abstract: A method for the separation of isobutene from a mixture comprising n-butene and isobutene comprising feeding a C.sub.4 stream containing n-butene and isobutene to a distillation column reactor into a feed zone contacting the stream with fixed bed acidic cation exchange resin to form diisobutene which passes to the bottom of the column, said n-butene being removed overhead. The reaction and distillation occur concurrently.Type: GrantFiled: July 27, 1978Date of Patent: December 30, 1980Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
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Patent number: 4232177Abstract: A method for conducting chemical reactions and fractionation of the reaction mixture comprising feeding reactants to a distillation column reactor into a feed zone and concurrently contracting the reactants with a fixed bed catalytic packing to concurrently carry out the reaction and fractionate the reaction mixture.For example, a method for preparing methyl tertiary butyl ether in high purity from a mixed feed stream of isobutene and normal butene comprising feeding the mixed feed stream to a distillation column reactor into a feed zone at the lower end of a distillation reaction zone, and methanol into the upper end of said distillation reaction zone, which is packed with a properly supported cationic ion exchange resin, contacting the C.sub.4 feed and methanol with the catalytic distillation packing to react methanol and isobutene, and concurrently fractionating the ether from the column below the catalytic zone and removing normal butene overhead above the catalytic zone.Type: GrantFiled: February 21, 1979Date of Patent: November 4, 1980Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.