Using Catalyst Containing Metal Bonded To Or Complexed With C, C-containing Compound, Or H Patents (Class 585/511)
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Patent number: 4594469Abstract: A process for oligomerizing alpha-olefins comprising contacting in a reactor zone under reaction conditions: (a) alpha-olefins having at least three carbon atoms; (b) an alkyl aluminum bromine or iodine compound having the formula R.sub.3 Al.sub.2 X.sub.3 or R.sub.n AlX.sub.3-n, wherein n is 1 or 2; R is an hydrocarbyl group and X is a reactive halogen selected from bromine and iodine; and (c) a cocatalyst which is (i) bromine, (ii) iodine, (iii) hydrocarbyl bromide having at least one halogen group reactive with said aluminum compound or (iv) hydrocarbyl iodide having at least one halogen group reactive with said aluminum compound.Type: GrantFiled: September 8, 1983Date of Patent: June 10, 1986Assignee: Uniroyal Chemical Company, Inc.Inventors: Frederick C. Loveless, Aspet V. Merijanian, David J. Smudin, Walter Nudenberg
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Patent number: 4544789Abstract: Regioselective and stereoselective synthesis of trans-internal olefins is effected with transition metal catalyst complexes having pairs of associated active sites. Photolytic conditions are generally employed.Type: GrantFiled: September 6, 1983Date of Patent: October 1, 1985Assignee: University of Illinois Board of TrusteesInventors: Theodore L. Brown, Philip O. Nubel
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Patent number: 4535135Abstract: The invention relates to new associations of strong bases, having the following general formula:n' RLi--n MZin which: n and n' are the numbers of mols of each compound, R is an alkyl or aryl radical, M is an alkali metal chosen from amongst lithium, sodium or potassium and Z is a hydride or an inorganic amide, the ratio n/n' being between 0.2 and 50.It is preferred to use bases in which the metal of the alkali metal amide or hydride is potassium or sodium. These associations are formed very rapidly and can be applied to anionic polymerization, in particular of conjugated dienes, in a solvent of low polarity or an apolar solvent.The polymers thus obtained contain a high percentage of 1,2 or 3,4 structures.Type: GrantFiled: October 24, 1983Date of Patent: August 13, 1985Assignee: Societe Nationale des Poudres et ExplosifsInventors: Serge Lecolier, Serge Raynal
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Patent number: 4528415Abstract: A novel ethylene dimerization catalyst is provided consisting essentially of a nickel compound, a phosphine compound, and an acidic compound. In addition, an improved ethylene dimerization process is provided which comprises contacting ethylene with the novel catalyst composition present, in an effective solvent, at a temperature from about 0.degree. C. to about 200.degree. C. As a result of the inventive precess, high catalyst productivity and good selectivity to the desired dimerized product, 1-butene, is obtained.Type: GrantFiled: August 20, 1981Date of Patent: July 9, 1985Assignee: Phillips Petroleum CompanyInventor: Ronald D. Knudsen
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Patent number: 4469910Abstract: A process is provided for oligomerizing alpha-olefins comprising contacting in a reaction zone under reaction conditions: (a) alpha-olefins having at least three carbon atoms; (b) an aluminum compound having the formula R.sub.3 Al, wherein R is an hydrocarbyl group and (c) a cocatalyst which is hydrocarbyl halide having at least one halogen group reactive with said aluminum compound, elemental bromine or elemental iodine.Type: GrantFiled: September 8, 1983Date of Patent: September 4, 1984Assignee: Uniroyal, Inc.Inventor: Frederick C. Loveless
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Patent number: 4451688Abstract: Olefins are polymerized in the presence of a catalyst which comprises the combination of:[I] a solid substance obtained by the reaction of at least the following two components:(i) a magnesium compound represented by the general formula R.sup.1.sub.m (OR.sup.2).sub.n MgX.sub.2-m-n wherein R.sup.1 and R.sup.2 are each a hydrocarbon radical having 1 to 24 carbon atoms, X is a halogen atom, m is 0.ltoreq.m.ltoreq.2 and n is 0.ltoreq.n.ltoreq.2, provided 0.ltoreq.m+n.ltoreq.2, and(ii) a titanium compound and/or a vanadium compound;[II] a silicon compound represented by general formula R.sup.1 mSi(OR.sup.2).sub.n X.sub.4-m-n wherein R.sup.1 and R.sup.2 are each hydrocarbon radical having 1 to 24 carbon atoms, X is a halogen atom, m is 0.ltoreq.m<4 and n is 0<n.ltoreq.4, provided 0 m+n 4;[III] an organometallic compound, where said catalyst comprises a product obtained by pre-reacting said silicon compound (II) and said organometallic compound (III).Type: GrantFiled: September 1, 1982Date of Patent: May 29, 1984Assignee: Nippon Oil Company, LimitedInventors: Nobuyuki Kuroda, Toru Nakamura, Yutaka Shikatani, Kazuo Matsuura, Mituji Miyoshi
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Patent number: 4409415Abstract: Olefin oligomers suitable as lubricants are prepared with a catalyst comprising boron trifluoride and a mixture of an alcohol, and a polyol. 1-Decene is oligomerized to a liquid product having an improved trimer to tetramer ratio using boron trifluoride and a mixture of n-butanol, and ethylene glycol.Type: GrantFiled: September 18, 1981Date of Patent: October 11, 1983Assignee: Gulf Research & Development CompanyInventors: Neal E. Morganson, Adam V. Vayda
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Patent number: 4382132Abstract: A process for the high pressure polymerization of ethylene in a reactor in the presence of conventional free radical generating initiators, wherein the initiator material is admixed with certain additives in small concentrations to lower the polymerization initiation temperature.Type: GrantFiled: June 1, 1981Date of Patent: May 3, 1983Assignee: El Paso Polyolefins CompanyInventors: Joseph M. Kelley, John J. Roderick
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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: 4377719Abstract: A process for preparing 1,7-octadiene by dimerizing butadiene in the presence of a catalytic amount of palladium acetate and a tertiary phosphine, a solvent in an amount sufficient to dissolve the catalyst, a strong base and formic acid, wherein: (a) the molar ratio of the strong base to the formic acid is 1:1-2, (b) the mole ratio of tertiary phosphine to palladium is at least 1, (c) the amount of strong base present is such that the pH of the reaction medium is from 7.5 to 10.5 and (d) the solvent is at least one member selected from the group consisting of aromatic hydrocarbons, lower alkyl substituted aromatic hydrocarbon, halogenated aromatic hydrocarbons, halogenated lower aliphatic hydrocarbons, nitriles, amides, dilower alkyl ethers, lower alkyl phenyl ethers, lower alkyl esters of lower alkanoic acids, ketones and lower alkanols.Type: GrantFiled: December 13, 1978Date of Patent: March 22, 1983Assignee: Charles U. Pittman, Jr.Inventors: Charles U. Pittman, Jr., Ronald Hanes
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Patent number: 4361714Abstract: A process for preparing linear alpha olefins and waxes having a total product M.sub.n in the range 200 to 700 which includes polymerizing an ethylene-containing gas in the presence of the reaction product of a zirconium halide with R.sub.2 Zn, wherein R is an alkyl group having about 1 to about 20 carbon atoms, in the presence of a diluent at a temperature of about 50.degree. to 200.degree. C. and an ethylene pressure above about 3.5 MPa, wherein the M.sub.n of said reaction product is controlled by the molar ratio of said R.sub.2 Zn/ZrCl.sub.4, said molar ratio being less than about 1.Type: GrantFiled: December 14, 1981Date of Patent: November 30, 1982Assignee: Exxon Research and Engineering Co.Inventors: Arthur W. Langer, John J. Steger, Terry J. Burkhardt
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Patent number: 4334117Abstract: This invention provides an improved process for producing alkadienes which comprises (1) contacting butadiene or isoprene with a catalyst such as platinum or palladium or a compound of one of said metals in a sulfolane solution, in the presence of a tertiary lower alkylamine formate and at least one phosphine compound of the formula: ##STR1## wherein R.sup.1 is a substituted or unsubstituted C.sub.1-10 hydrocarbon group; R.sup.2 is H, a saturated aliphatic C.sub.1-5 hydrocarbon group, nitro or halogen; m is 1, 2 or 3; n is 0 or 1; x is 0, 1 or 2; y and z each is 0, 1, 2 or 3 (provided that y and z are not zero concurrently and x+y+z=3); A is --SO.sub.3 M wherein M is a cation selected from among H, alkali metals, alkaline earth metals and NH.sub.4 or the formate or an inorganic acid salt of ##STR2## wherein R.sup.3 and R.sup.4 each means a saturated aliphatic C.sub.Type: GrantFiled: September 4, 1980Date of Patent: June 8, 1982Assignee: Kuraray Co., Ltd.Inventors: Noriaki Yoshimura, Masuhiko Tamura
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Patent number: 4311613Abstract: A catalyst is prepared by reacting tungsten hexafluoride with a branched-chain aliphatic alcohol in a molar ratio of 2:1 to 20:1. This catalyst can be used to oligomerize 1-butene to produce synthetic hydrocarbon oils.Type: GrantFiled: December 15, 1980Date of Patent: January 19, 1982Assignee: Gulf Research & Development CompanyInventors: John P. Pellegrini, Jr., Richard G. Austin, David L. Beach
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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: 4301318Abstract: Ammonium hydroxide is used to remove nickel ylide residue from an oligomerization reaction product obtained by contacting ethylene with a nickel ylide catalyst under oligomerization conditions. The oligomerization reaction product is contacted with ammonium hydroxide to obtain a product composed of two layers, an upper layer containing normal alpha olefins and a lower layer containing nickel ylide residue. The two layers are then separated from each other to recover the desired normal alpha olefins.Type: GrantFiled: November 25, 1980Date of Patent: November 17, 1981Assignee: Gulf Research & Development CompanyInventors: David L. Beach, James J. Harrison
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Patent number: 4293726Abstract: An alpha olefin containing three to 10 carbon atoms, or higher, is oligomerized by intimately contacting the alpha olefin, e.g., in a non-aromatic solvent, with a catalyst produced by contacting (a) a refractory metal oxide/silica support such as alumina/silica wherein the silica content of the support is from about 2 to about 95 weight percent and the metal oxide content of the support is from about 5 to about 98 percent with (b) a tris(cyclopentadienyl)trinickel dicarbonyl. This process is characterized by a relatively high reaction rate at moderate temperatures and pressures and results in the production of significant quantities of dimers, trimers and tetramers.Type: GrantFiled: May 21, 1980Date of Patent: October 6, 1981Assignee: Gulf Research & Development CompanyInventors: David L. Beach, Thaddeus P. Kobylinski
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Patent number: 4293725Abstract: Ethylene is oligomerized by intimately contacting ethylene with a metal modified catalyst. The catalyst is produced by contacting (a) a refractory metal oxide/silica support, such as alumina/silica wherein the silica content of the support is from about 2 to about 95 weight percent and the metal oxide content of the support is from about 5 to about 98 percent with (b) a solution of a basic metal and then (c) contacting the resulting metal modified support with a tris(cyclopentadienyl)trinickel dicarbonyl.Type: GrantFiled: May 21, 1980Date of Patent: October 6, 1981Assignee: Gulf Research & Development CompanyInventors: David L. Beach, Thaddeus P. Kobylinski
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Patent number: 4288648Abstract: Ethylene is oligomerized by contacting ethylene with a catalyst produced by contacting (a) a refractory metal oxide/silica support such as alumina/silica wherein the silica content of the support is from about 2 to about 95 weight percent and the metal oxide content of the support is from about 5 to about 98 percent with (b) a tris(cyclopentadienyl)trinickel dicarbony. This process is characterized by a relatively high reaction rate at moderate temperatures and pressures and results in the production of relatively high proportions of desirable trimer, tetramer, pentamer, and higher olefinic products.Type: GrantFiled: May 21, 1980Date of Patent: September 8, 1981Assignee: Gulf Research & Development CompanyInventors: David L. Beach, Thaddeus P. Kobylinski
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Patent number: 4272406Abstract: A catalyst that is highly active at low operating temperatures and pressures in the oligomerization of lower olefins such as ethylene is produced by contacting (a) a refractory metal oxide/silica support such as alumina/silica wherein the silica content of the support is from about 2 to about 95 weight percent and the metal oxide content of the support is from about 5 to about 98 percent with (b) a tris(cyclopentadienyl)trinickel dicarbonyl. When used to oligomerize ethylene, these catalysts are characterized by a relatively high reaction rate at moderate temperatures and pressures. Their use permits the production of relatively high proportions of desirable trimer, tetramer, pentamer, and higher olefinic products.Type: GrantFiled: May 21, 1980Date of Patent: June 9, 1981Assignee: Gulf Research & Development CompanyInventors: David L. Beach, Thaddeus P. Kobylinski
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Patent number: 4272407Abstract: A catalyst that is highly active in the oligomerization of lower olefins such as ethylene is produced by contacting (a) a refractory metal oxide/silica support, such as alumina/silica wherein the silica content of the support is from about 2 to about 95 weight percent and the metal oxide content of the support is from about 5 to about 98 percent with (b) a solution of a basic metal and then (c) contacting the resulting metal modified support with a tris(cyclopentadienyl)trinickel dicarbonyl.Type: GrantFiled: May 21, 1980Date of Patent: June 9, 1981Assignee: Gulf Research & Development CompanyInventors: David L. Beach, Thaddeus P. Kobylinski
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Patent number: 4245131Abstract: Tantalum and niobium catalysts or catalyst precursors of the formula: ##STR1## wherein R is cyclopentadienyl, which can be substituted with methyl up to five positions, or neopentylidene, R.sup.1 is neopentyl or benzyl, n is 0 or 1, R.sup.2 is neopentylidene, benzylidene, tetramethylene, or 2,3-dimethyltetramethylene, A is halo or a moiety of the formula YR.sup.3 R.sup.4 R.sup.5 wherein Y is a group 5 element including N, P, As, Sb and Bi and R.sup.3, R.sup.4, R.sup.5 can be the same or different and are C.sub.1 -C.sub.4 alkyl, aralkyl such as naphthyl, neophyl, tolyl or xylyl, aryl such as benzyl or phenyl or bipyridyl and Z is tantalum or niobium. The compounds selectively dimerize 1-olefins to 1-butenes; m=1 or 2.Type: GrantFiled: July 2, 1979Date of Patent: January 13, 1981Assignee: Massachusetts Institute of TechnologyInventor: Richard R. Schrock
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Patent number: 4243829Abstract: A process for preparing 1,7-octadiene by dimerizing butadiene in the presence of a catalytic amount of palladium acetate and a tertiary phosphine, a solvent in an amount sufficient to dissolve the catalyst, a strong base and formic acid, wherein: (a) the molar ratio of the strong base to the formic acid is 1:1-2, (b) the mole ratio of tertiary phosphine to palladium is at least 1, (c) the amount of strong base present is such that the pH of the reaction medium is from 7.5 to 10.5 and (d) the solvent is at least one member selected from the group consisting of aromatic hydrocarbons, lower alkyl substituted aromatic hydrocarbons, halogenated aromatic hydrocarbons, halogenated lower aliphatic hydrocarbons, nitriles, amides, dilower alkyl ethers, lower alkyl phenyl ethers, lower alkyl esters of lower alkanoic acids, ketones and lower alkanols.Type: GrantFiled: October 4, 1976Date of Patent: January 6, 1981Assignee: Charles U. Pittman, Jr.Inventors: Charles U. Pittman, Jr., Ronald Hanes
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Patent number: 4242481Abstract: Novel organoaluminum compounds having the formula XYA1 ##STR1## in which X is a halogen, Y is an alkyl group having from 1 to 10 carbon atoms, a phenyl group or a halogen, R is an alkyl group having from 2 to 9 carbon atoms, and n is an integer from 1 to 20. These compounds are less viscous and more soluble in hydrocarbon solvents than are corresponding ethylene-based or butadiene-based compounds. The novel compounds are prepared by the reaction of alkylaluminum dihalides or aluminum trihalides with a terminal olefin having from 3 to 10 carbon atoms in the presence of aluminum metal.Type: GrantFiled: May 7, 1979Date of Patent: December 30, 1980Assignee: Texas Alkyls, Inc.Inventor: Loyd W. Fannin
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Patent number: 4238628Abstract: Process for the production of undegraded alkylated aromatic compounds by alkylating an aromatic compound with a C.sub.3 or higher olefin polymer having terminal ethylene units.Type: GrantFiled: September 28, 1978Date of Patent: December 9, 1980Assignee: Standard Oil Company (Indiana)Inventors: Paul J. Cahill, Carl E. Johnson
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Patent number: 4225743Abstract: In a dimerization of butenes containing isobutene, a formation of 2,2,4-trimethyl pentenes is minimized by using a specific nickel catalyst solution and an organoaluminum catalyst. The specific nickel catalyst is a nickel salt of a fatty acid having 1.5 to 40 wt. % of a free fatty acid and less than 0.1 wt. % of water.The C.sub.8 olefins having less 2,2,4-trimethyl pentenes obtained by the dimerization are quite important to produce excellent plasticizer.Type: GrantFiled: December 15, 1978Date of Patent: September 30, 1980Assignee: Nissan Chemical Industries LimitedInventors: Satoshi Hoshiyama, Shuichi Fukushima, Hiroshi Kobayashi, Hideki Takamatsu
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Patent number: 4197419Abstract: Tantalum catalysts or catalyst precursors of the formula ##STR1## wherein X is a halide, or alkoxide and L is an alkene (CH.sub.2 .dbd.CHR) having from 2 to 20 carbon atoms, react with 1-olefins to give catalysts of the formula ##STR2## wherein R.sup.2 is hydrogen or a C.sub.1 to C.sub.18 alkyl such as methyl, ethyl, or propyl. The catalysts or catalyst precursors selectively dimerize 1-olefins to the two possible disubstituted .alpha.-olefin dimers, the ratio of which depends on the nature of R.Type: GrantFiled: December 15, 1978Date of Patent: April 8, 1980Assignee: Massachusetts Institute of TechnologyInventor: Richard R. Schrock
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Patent number: 4180694Abstract: Butadiene is hydrodimerized to 1,7-octadiene in high yield by contacting the butadiene with a formate of an alkali metal, alkaline earth metal or ammonia, a palladium catalyst, tertiary phosphine, a solvent selected from dialkyl sulfoxides, N,N-dialkylalkanamides, substituted and unsubstituted pyridines and sulfolanes and at least one mole of water per mole of formate salt.Type: GrantFiled: July 24, 1978Date of Patent: December 25, 1979Assignee: Shell Oil CompanyInventor: Kenzie Nozaki
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Patent number: 4176086Abstract: Preparation of a hydrocarbon-soluble nickel complex substantially free of moisture comprising reacting a nickel compound with an organic complexing agent in a hydrocarbon solvent to form a complex, allowing the complex to settle and separate into a water phase and a hydrocarbon solution of the complex, then drying the hydrocarbon solution of complex by azeotropic distillation. The substantially anhydrous nickel complex obtained can be mixed with an alkylaluminum halide to form a catalyst system useful for the dimerization of olefins.Type: GrantFiled: August 25, 1977Date of Patent: November 27, 1979Assignee: Phillips Petroleum CompanyInventor: Cecil O. Carter
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Patent number: 4172855Abstract: A process for making a low viscosity, low volatility .alpha.-olefin oligomer suitable for use as a functional fluid or lubricating oil comprising dimerizing a C.sub.6-12 .alpha.-olefin, reacting the resultant dimer with a C.sub.6-18 .alpha.-olefin in the presence of a Friedel-Crafts catalyst, distilling out volatile components and hydrogenating the residual product.Type: GrantFiled: April 10, 1978Date of Patent: October 30, 1979Assignee: Ethyl CorporationInventors: Ronald L. Shubkin, Ellis B. Rifkin, Martin E. Gluckstein
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Patent number: 4170603Abstract: Novel organoaluminum compounds having the formula ##STR1## in which X is a halogen, Y is an alkyl group having from 1 to 10 carbon atoms, a phenyl group or a halogen, R is an alkyl group having from 2 to 9 carbon atoms, and n is an integer from 1 to 20. These compounds are less viscous and more soluble in hydrocarbon solvents than are corresponding ethylene-based or butadiene-based compounds.The novel compounds are prepared by the reaction of alkylaluminum dihalides or aluminum trihalides with a terminal olefin having from 3 to 10 carbon atoms in the presence of aluminum metal.Type: GrantFiled: March 3, 1977Date of Patent: October 9, 1979Assignee: Stauffer Chemical CompanyInventor: Loyd W. Fannin