Al-and Transition Metal-containing Patents (Class 585/512)
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Patent number: 4816610Abstract: The invention concerns a procedure for manufacturing short-chain linear .alpha.-olefines, in particular 1-butylene, selectively from ethylene. A nickel chelate in which the ligand is diphenyl (2-carboxymethyl) phosphine, diphenyl (2-carboxyethyl) phosphine, or an alkali metal salt of these, or an alkali metal salt of diphenyl (2-hydroxyethyl) phosphine, with or without a promoter, is used for a catalyst.Type: GrantFiled: February 12, 1988Date of Patent: March 28, 1989Assignee: Neste OyInventors: Salme Koskimies, Leena Rantanen, Jouni Kivi, Erkki Halme
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Patent number: 4814540Abstract: Disclosed is a process for producing propylene oligomers at high selectivities which comprises oligomerizing propylene in the presence of a catalyst comprising an alkyl substituted cyclopentadienyl compound of zirconium and/or hafnium and a condensation product of organoaluminum compound and water.Type: GrantFiled: November 13, 1987Date of Patent: March 21, 1989Assignee: Idemitsu Kosan Company LimitedInventors: Masami Watanabe, Masahiko Kuramoto
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Patent number: 4804798Abstract: Polymers of alpha-olefins of formulaR--CH.dbd.CH.sub.2wherein R=alkyl of from 1 to 6 C atoms, or of their mixtures with minor amounts of ethylene are obtained by adopting catalysts comprising:(A) a solid component obtained by treating an emulsion (a) in a perfluoropolyether liquid of a liquid compound of magnesium, of titanium or of another transition metal, either liquid or in solution, with possibly using an electron-donor compound, with (b) a reducing and/or halogenating agent capable of forming an insoluble solid product, after which, if such a product is a precursor of the catalytic components, it is treated with a tetravalent-titanium halide, or with a halide of another transition metal;(B) an aluminum-alkyl compound;(C) an outer electron-donor compound (c).Type: GrantFiled: July 27, 1987Date of Patent: February 14, 1989Assignee: Montedison S.p.A.Inventor: Enrico Albizzati
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Patent number: 4795852Abstract: An olefinic feedstock containing contaminants such as oxygenates may be oligomerized to a desired oligomer which contains a particular configuration. The process may be effected by utilizing a catalyst which comprises a porous support containing a catalytically effective amount of an iron group metal compound in combination with a catalytically effective amount of an alkyl aluminum compound and an activator comprising an aluminum alkoxide. The presence of the latter compound in the catalyst compound will permit the catalyst to maintain its activity and stability over a relatively long period of time. The catalyst of the invention is prepared by impregnating a porous support with an aqueous solution of an iron group metal salt, calcining and contacting the calcined support with a solution containing an alkyl aluminum compound and an aluminum alkoxy compound.Type: GrantFiled: December 14, 1987Date of Patent: January 3, 1989Assignee: UOP Inc.Inventors: Robert R. Frame, Paul T. Barger
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Patent number: 4795851Abstract: Olefinic feedstocks which contain catalyst contaminants or poisons such as sulfur-containing compounds may be oligomerized to a desired oligomer and configuration of the oligomer by utilizing a catalyst which is stable and will not deactivate due to the presence of the aforementioned poisons. The catalyst comprises a porous support which has been impregnated with a catalytically effective amount of an iron group metal compound and a Group IVA metal compound. In addition, the catalyst composite may also contain in combination therewith, a catalytically effective amount of an alkyl aluminum compound and an aluminum alkoxy/aluminum halide compound. The catalyst of this invention is prepared by impregnating a porous support with an aqueous solution containing an iron group metal salt and a Group IVA metal salt, calcining and containing the calcined support with a solution containing an alkyl aluminum compound.Type: GrantFiled: December 14, 1987Date of Patent: January 3, 1989Assignee: UOP Inc.Inventors: Robert R. Frame, Tamotsu Imai
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Patent number: 4777314Abstract: New nickel composition having substantial solubility in hydrocarbons and prepared by reacting at least one inorganic divalent nickel compound, at least one halogenoacetic acid and at least one ester of the formula R.sub.1 COO R.sub.2 wherein R.sub.1 is hydrogen or hydrocarbyl and R.sub.2 is hydrocarbyl. The resultant composition can be used in admixture with a hydrocarbylaluminum halide as catalyst for olefin dimerization.Type: GrantFiled: November 12, 1987Date of Patent: October 11, 1988Assignee: Institut Francais du PetroleInventors: Gerard Provin, Alain Forestiere, Dominique Commereuc
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Patent number: 4777315Abstract: A process for the trimerization of an olefin selected from the group consisting of ethylene, propylene, 1-butene, and mixtures thereof comprising passing the olefin and carbon dioxide in contact with a catalyst comprising the reaction product of (i) a chromium compound, which will provide active catalytic species under trimerization conditions, and (ii) a hydrocarbyl aluminum hydrolyzed with about 0.7 to about 1.1 moles of water per mole of aluminum compound wherein the aluminum to chromium mole ratio is in the range of up to about 200 to one and the mole ratio of olefin to carbon dioxide is in the range of about 4 to about 3000 moles of olefin per mole of carbon dioxide.Type: GrantFiled: June 1, 1987Date of Patent: October 11, 1988Assignee: Union Carbide CorporationInventors: Isaac J. Levine, Frederick J. Karol
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Patent number: 4769510Abstract: In the polymerization of propylene and other higher 1-olefins, polymers which have a high degree of isotacticity and a narrow distribution of molecular weight are obtained in the presence of a catalyst system composed of a zirconium compound which is stereo-rigid and chiral and a linear or cyclic aluminoxane. In addition, the catalyst system is exceptionally active.Type: GrantFiled: November 25, 1985Date of Patent: September 6, 1988Assignee: Hoechst AktiengesellschaftInventors: Walter Kaminsky, Klaus Kulper, Maria Buschermohle, Hartmut Luker
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Patent number: 4740652Abstract: Olefinic hydrocarbons which contain from 2 to about 6 carbon atoms may be oligomerized to form oligomers of desired configuration utilizing a process which comprises contacting said olefins with a catalyst which comprises a porous support containing a catalytically effective amount of a non-stoichiometric hydrogen and oxygen-containing iron group metal in combination with a catalytically effective amount of an alkyl aluminum compound and an aluminum halide. Oligomerization conditions which are employed to effect the process will include temperatures in the range of from about -20.degree. to about 120.degree. C. and a pressure in the range of from about 350 to about 1,000 pounds per square inch gauge.Type: GrantFiled: February 27, 1987Date of Patent: April 26, 1988Assignee: UOP Inc.Inventor: Robert R. Frame
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Patent number: 4737480Abstract: Olefinic feedstocks which contain catalyst contaminants or poisons such as sulfur-containing compounds may be oligomerized to a desired oligomer and configuration of the oligomer by utilizing a catalyst which is stable and will not deactivate due to the presence of the aforementioned poisons. The catalyst comprises a porous support which has been impregnated with a catalytically effective amount of a non-stoichiometric hydrogen and oxygen-containing iron group metal compound and a compound containing a metal of Group IVA of the Periodic Table. In addition, the catalyst composite will also contain in combination therewith, a catalytically effective amount of an alkyl aluminum compound and an aluminum alkoxy/aluminum halide compound.Type: GrantFiled: March 12, 1987Date of Patent: April 12, 1988Assignee: UOP Inc.Inventors: Robert R. Frame, Tamotsu Imai
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Patent number: 4737479Abstract: An olefinic feedstock containing contaminants such as oxygenates may be oligomerized to a desired oligomer which contains a particular configuration. The process may be effected by utilizing a catalyst which comprises a porous support containing a catalytically effective amount of a non-stoichiometric hydrogen and oxygen-containing iron group metal compound in combination with a catalytically effective amount of an alkyl aluminum compound and an activator comprising an aluminum alkoxide. The presence of the latter compound in the catalyst compound will permit the catalyst to maintain its activity and stability over a relatively long period of time.Type: GrantFiled: March 13, 1987Date of Patent: April 12, 1988Assignee: UOP Inc.Inventors: Robert R. Frame, Paul T. Barger
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Patent number: 4721762Abstract: The invention concerns a process for manufacturing low density linear polyethylene by copolymerizing ethylene and 1-butene, comprising the steps of:(a) dimerizing ethylene to 1-butene in the presence of a soluble catalyst comprising: an alkyl titanate, an aluminum compound of formula AlR.sub.3 or AlR.sub.2 H, wherein R is a hydrocarbyl radical, and an ether;(b) contacting at least a portion of the product obtained in step (a) with an inorganic compound, at least partly insoluble;(c) contacting the insoluble mixture obtained in step (b) with an halogenated aluminum compound of formula Al.sub.2 R'.sub.6-n X.sub.n, wherein R' is a hydrocarbyl radical, X a halogen atom, and n a number from 3 to 6, when an halogenated aluminum compound is not already present in said mixture;(d) using the resultant product, containing at least one inorganic carrier, at least one halogenated aluminum compound and at least one titanium compound, as catalyst in the polymerization reactor.Type: GrantFiled: June 7, 1985Date of Patent: January 26, 1988Assignee: Institut Francais du PetroleInventors: Dominique Commereuc, Francois Hugues, Nhuong Le Quan, Adberrahim Taouli
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Patent number: 4704491Abstract: A liquid ethylene-alpha-olefin random copolymer, characterized in that(a) it has an ethylene unit content of 10 to 85 mole % and an alpha-olefin unit content of 15 to 90 mole %,(b) it has a low molecular weight,(c) it has a narrow molecular weight distribution,(d) the dispersion of the ethylene units and alpha-olefin units in the polymer chain is in the advanced state, and(e) the directions of bonding of the alpha-olefin units in the polymer chain are nearly the same.The copolymer is prepared by copolymerizing ethylene and an alpha-olefin having 3 to 20 carbon atoms in the presence of a catalyst comprising a compound of a transition metal of Group IVb of the periodic table and an aluminoxane. The copolymer is very useful as a synthetic lubricant oil.Type: GrantFiled: March 25, 1986Date of Patent: November 3, 1987Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Toshiyuki Tsutsui, Mamoru Kioka, Akinori Toyota, Norio Kashiwa
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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: 4668834Abstract: Low molecular weight copolymers comprised of ethylene, an alphaolefin and (optionally) a nonconjugated polyene, which copolymers have a viscosity index of at least about 75 and vinylidene-type unsaturation, possess unexpected advantages as intermediates in epoxy-grafted electrical encapsulation compositions.Type: GrantFiled: October 16, 1985Date of Patent: May 26, 1987Assignee: Uniroyal Chemical Company, Inc.Inventors: Yong S. Rim, Demetreos N. Matthews
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Patent number: 4668838Abstract: A process for the trimerization of an olefin selected from the group consisting of ethylene, propylene, 1-butene, and mixtures thereof comprising passing the olefin in contact with a catalyst comprising the reaction product of (i) a chromium compound, which will provide active catalytic species under trimerization conditions; (ii) a hydrocarbyl aluminum hydrolyzed with about 0.8 to about 1.1 moles of water per mole of aluminum compound; and (iii) a donor ligand selected from the group consisting of hydrocarbyl isonitriles, amines, and ethers wherein the aluminum to chromium mole ratio is in the range of up to about 200 to one and the ligand to chromium mole ratio is in the range of up to about 100 to one.Type: GrantFiled: March 14, 1986Date of Patent: May 26, 1987Assignee: Union Carbide CorporationInventor: John R. Briggs
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Patent number: 4665262Abstract: An olefin polymerization catalyst system comprising (I) a polymerization catalyst produced by treating an inert support material, preferably a hydrated high surface area silica support having 1.00 to 1.50 hydroxyls per gram of silica with the reaction product of an organomagnesium compound and first a zirconium compound and/or a hafnium compound then a halogenator and tetravalent titanium compound, (II) an organoaluminum compound cocatalyst and (III) a chlorinated hydrocarbon promoter which produces polymers having broad molecular weight distribution in high yields.Type: GrantFiled: October 18, 1985Date of Patent: May 12, 1987Assignee: Exxon Research & Engineering Co.Inventor: Victoria Graves
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Patent number: 4658078Abstract: This invention relates to a process for dimerizing an alpha olefin to a vinylidene olefin which comprises contacting said alpha olefin with a catalyst comprising (a) cyclo(pentadienyl)zirconium or hafnium metallocene and (b) an aluminoxane wherein the atom ratio of Al to Zr or Hf in the catalyst ranges from about 1 to about 100.Type: GrantFiled: August 15, 1986Date of Patent: April 14, 1987Assignee: Shell Oil CompanyInventors: Lynn H. Slaugh, Galeon W. Schoenthal
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Patent number: 4615998Abstract: A catalyst is formed by reacting, in a hydrocarbon medium, a trialkylaluminum with a mixture of an alkyl titanate with an ether. The activity and the selectivity are improved when adding the trialkylaluminum to a pre-formed mixture of alkyl titanate with ether.Type: GrantFiled: April 30, 1985Date of Patent: October 7, 1986Assignee: Institut Francais du PetroleInventors: Nhuong Le Quan, Daniel Cruypelinck, Dominique Commereuc, Yves Chauvin, Gerard Leger
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Patent number: 4590325Abstract: A titanium halide containing catalyst component for polymerization of olefins which is prepared by reacting a magnesium hydrocarbyloxide with a silicon compound having a hydrogen-silicon bond, contacting the reaction product with an electron donor compound, contacting the resulting contact product two or more times with a titanium halide and between one of the multiple titanium halide contacts, contacting the titanium halide contacted solid with a halogenated hydrocarbon.Type: GrantFiled: August 15, 1985Date of Patent: May 20, 1986Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Masafumi Imai, Tadashi Yamamoto, Hiroyuki Furuhashi, Hiroshi Ueno, Naomi Inaba
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Patent number: 4538018Abstract: A method of pre-conditioning the walls of an olefin dimerization reactor and starting a dimerization process comprises sequential steps of introducing a first soluble homogeneous catalyst component comprising, e.g. a complex of a divalent metal selected from the group consisting of nickel, cobalt and iron, and a second soluble homogeneous catalyst component comprising, e.g. an organoaluminum compound, at rates such that the molar catalyst feed ratio of said aluminum to said divalent metal is maintained at a first value during the pre-conditioning and startup period and at a second, higher, value during the operating period.Type: GrantFiled: December 13, 1983Date of Patent: August 27, 1985Assignee: Phillips Petroleum CompanyInventor: Cecil O. Carter
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Patent number: 4532370Abstract: Process for synthesizing 1-butene by dimerization of ethylene, in the presence of a catalyst formed by reacting, in a hydrocarbon medium, a trialkylaluminum with a mixture of an alkyl titanate with an ether. The activity and the selectivity are improved when adding the ether to a pre-formed mixture of alkyl titanate with trialkylaluminum.Type: GrantFiled: September 20, 1984Date of Patent: July 30, 1985Assignee: Institut Francais du PetroleInventors: Nhuong Le Quan, Daniel Cruypelinck, Dominique Commereuc, Yves Chauvin, Gerard Leger
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Patent number: 4525551Abstract: This invention relates to a novel highly active and more efficient catalyst system for polymerizing alpha-olefins to prepare high, medium, and low molecular weight polymers. This highly active olefin polymerization catalyst therefore can be used to prepare both olefin waxes as well as high molecular weight crystalline polyolefins. This highly efficient, highly active catalyst is prepared by reacting a vanadium tetrahalide with a titanium tetravalent member in a hydrocarbon medium. The product of this reaction is then combined with an activating component, such as triethyl aluminum, to form a highly active and efficient polyolefin catalyst.Type: GrantFiled: December 2, 1983Date of Patent: June 25, 1985Assignee: Eastman Kodak CompanyInventor: Robert R. Schmidt
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Patent number: 4510342Abstract: A method for preparing synthetic oils characterized by a high viscosity index and prepared from 1-olefin is described. The method comprises polymerizing a 1-olefin or a mixture of 1-olefins in the presence of(a) at least one transition metal halide catalyst,(b) at least one alkyl aluminum compound containing up to about 15 carbon atoms in each alkyl group and up to about 40 carbon atoms per molecule as a co-catalyst, and(c) a saturated alkyl fluoride.The homopolymers and copolymers prepared in accordance with the method of the invention generally are characterized by a high viscosity index such as between about 100 to 300. The homopolymers and copolymers are useful as synthetic lubricants and as additives to synthetic or mineral oil lubricants for modifying the viscosity index characteristics of the lubricants.Type: GrantFiled: December 29, 1982Date of Patent: April 9, 1985Assignee: The Standard Oil CompanyInventors: Janie K. Currie, J. Robert Mooney
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Patent number: 4476341Abstract: n-Butene is dimerized with improved conversion using an in situ produced homogeneous catalyst system formed from a nickel compound such as nickel octoate, an organoaluminium compound such as aluminium monoethyl dichloride, the butene and hydrogen.Type: GrantFiled: March 30, 1983Date of Patent: October 9, 1984Assignee: Exxon Research & Engineering Co.Inventor: Georges M. K. Mathys
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Patent number: 4463201Abstract: High quality synthetic lubricating oils are provided when certain olefinic monomers such as ethylene, propylene and a third 1-olefin are copolymerized and thereafter dewaxed by means of a urea adduction process.Type: GrantFiled: January 24, 1983Date of Patent: July 31, 1984Assignee: Mobil Oil CorporationInventors: John W. Schick, Robert M. Gemmill, Jr.
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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: 4434313Abstract: A process for preparing linear alpha olefins and waxes having a total product M.sub.n in the range 200 to 700 comprising at least 90 mole percent linear alpha olefins which includes polymerizing an ethylene containing gas in the presence of the reaction product of a zirconium halide compound with an aluminum cocatalyst selected from the group consisting of dialkyl aluminum alkoxides or aryloxides and dialkyl aluminum disubstituted amides 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 aluminum cocatalyst/Zr halide, said molar ratio being less than about 10.Type: GrantFiled: December 29, 1982Date of Patent: February 28, 1984Assignee: Exxon Research and Engineering Co.Inventor: Arthur W. Langer, Jr.
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Patent number: 4418184Abstract: Improved process for preparing an ethylene polymer wax which comprises polymerizing ethylene or copolymerizing ethylene with up to 10 mole % of an alpha-olefin having 3 to 20 carbon atoms in the presence of (A) a highly active titanium catalyst component activated by a magnesium compound and (B) an organoaluminum catalyst component composed of (B-1) an organoaluminum compound free from halogen bonded directly to the aluminum atom and (B-2) a halogen compound of an element selected from the group consisting of elements other than titanium of Groups III and IV of the Mendelejeff's periodic table, the atomic ratio of halogen to aluminum in the organoaluminum catalyst component (B) being from about 1:6 to about 9:10, provided that when said halogen compound is a halogen compound of carbon, this atomic ratio is from about 1:6 to about 10:1, and said polymerization or copolymerization being carried out under such conditions that the concentration of ethylene polymer wax in the polymerization or copolymerization sysType: GrantFiled: March 22, 1982Date of Patent: November 29, 1983Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Takashi Ueda, Norio Kashiwa
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Patent number: 4410750Abstract: A process for preparing linear alpha olefins and waxes having a total product M.sub.n in the range 200 to 700 comprising at least 90 mole percent linear alpha olefins which includes polymerizing an ethylene containing gas in the presence of the reaction product of a zirconium halide compound with an aluminum cocatalyst selected from the group consisting of dialkyl aluminum alkoxides or aryloxides and dialkyl aluminum disubstituted amides in the presence of a pi base and 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 aluminum cocatalyst/Zr halide, said molar ratio being less than about 1.Type: GrantFiled: December 29, 1982Date of Patent: October 18, 1983Assignee: Exxon Research and Engineering Co.Inventor: Arthur W. Langer, Jr.
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Patent number: 4404415Abstract: A process is provided for the production of nonenes or of a nonenes/dodecenes mixture, wherein: propylene is introduced into a liquid reaction phase containing a soluble dimerization catalyst, the temperature is 20.degree.-60.degree. C., at least a portion of the resultant hexenes is recycled and the propylene concentration is maintained between 0.05 and 1% by weight.Type: GrantFiled: April 21, 1982Date of Patent: September 13, 1983Assignee: Institut Francais du PetroleInventor: Jean Gaillard
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Patent number: 4398049Abstract: A catalyst composition is manufactured by admixing a hydrocarbyl aluminum halide of a nickel compound of the formula (R.sub.1 COO)(R.sub.2 COO)Ni, where R.sub.1 is hydrocarbyl with at least 5 carbon atoms and R.sub.2 is haloalkyl of 1-3 carbon atoms. Olefins such as ethylene, propylene and butenes can be oligomerized, for example, dimerized and trimerized, with the above catalyst composition.Type: GrantFiled: September 28, 1982Date of Patent: August 9, 1983Assignee: Institut Francais du PetroleInventors: Dominique Le Pennec, Dominique Commereuc, Yves Chauvin
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Patent number: 4387262Abstract: A process for oligomerizing olefins uses a catalyst composition obtained by contacting (a) bivalent nickel compound with (b) a hydrocarbylaluminum compound of the formula Al R.sub.x X.sub.y where R is a monovalent hydrocarbon radical, X is halogen, x is from 1 to 1.5, y is from 1.5 to 2, x+y being equal to 3, and (c) a Bronsted acid consisting preferably of a halogenocarboxylic acid of the formula R.sub.1 COOH in which R.sub.1 is a halogenoalkyl radical of the formula C.sub.m H.sub.p X.sub.q X being halogen, m an integer from 1 to 3, p being zero or an integer and q being an integer, the condition p+q=2m+1 being fulfilled. A preferred Bronsted acid is of the formula R.sub.2 COOH in which R.sub.2 is a halogenomethyl group of the formula CX.sub.n H.sub.3-n, X being halogen and n an integer from 1 to 3.Type: GrantFiled: January 22, 1981Date of Patent: June 7, 1983Assignee: Institut Francais Du PetroleInventors: Yves Chauvin, Domonique Commereuc, Jean Gaillard, Gerard Leger, Nhu H. Phung
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Patent number: 4377720Abstract: A process for preparing linear alpha olefins and waxes having a total product M.sub.n in the range 200 to 700 comprising at least 90 mole percent linear alpha olefins which includes polymerizing an ethylene containing gas in the presence of the reaction product of a zirconium halide compound with an aluminum cocatalyst selected from the group consisting of dialkyl aluminum alkoxides or aryloxides and dialkyl aluminum disubstituted amides 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 aluminum cocatalyst/Zr halide, said molar ratio being less than about 1.Type: GrantFiled: December 14, 1981Date of Patent: March 22, 1983Assignee: Exxon Research and Engineering Co.Inventor: Arthur W. Langer
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Patent number: 4362650Abstract: An improved catalyst composition is obtained by contacting at least one bivalent nickel compound with at least one hydrocarbyl aluminum halide, at least one Bronsted organic acid and at least one anhydride of a carboxylic acid. The composition can be used as a catalyst for olefin oligomerization.Type: GrantFiled: May 8, 1981Date of Patent: December 7, 1982Assignee: Institut Francais du PetroleInventors: Yves Chauvin, Dominique Commereuc, Gerard Leger, Jean Gaillard, Nhu H. Phung
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Patent number: 4320243Abstract: At least one of propene and butene is oligomerized, preferably dimerized, in an elongate cylindrical reaction zone. A recycle flow and the fresh feed charge are injected tangentially into said reaction zone. The catalyst preferably comprises a nickel compound and a hydrocarbyl aluminum halide.Type: GrantFiled: March 27, 1979Date of Patent: March 16, 1982Assignee: Institut Francais du PetroleInventors: Yves Chauvin, Jean Gaillard, Gerard Leger, Hugo Van Landeghem
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Patent number: 4317948Abstract: A mixed olefin feedstock obtained from disproportionating C.sub.8 to C.sub.18 1-olefins can be used as such for a dimerization process to produce branched hydrocarbons that are useful as lubricating oils or greases.Type: GrantFiled: March 21, 1980Date of Patent: March 2, 1982Assignee: Phillips Petroleum CompanyInventor: Louis F. Heckelsberg
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Patent number: 4309387Abstract: Olefins are dimerized in a loop reactor with flashing of the reactor effluent in a flashing zone within the loop. A subsequent flash in a second flashing zone can also be used for the removal of product as flash vapor. In another embodiment, separated product dimers or product heavies are used as absorbents for unreacted ethylene. The use of a vapor-liquid contacting device incorporated in the loop reactor is especially helpful in the dimerization of an olefin when the olefin is available in low-concentration gas streams. A thermosiphon loop reactor can also be used for low-concentration olefin streams to minimize the power requirements as the energy of the feed gas is used to induce the reactor circulation.Type: GrantFiled: July 2, 1980Date of Patent: January 5, 1982Assignee: Phillips Petroleum CompanyInventor: Cecil O. Carter
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Patent number: 4293723Abstract: A novel aluminous composition prepared by impregnating porous gamma alumina with aluminum hydride and subsequently heating the impregnated alumina to a temperature of from about 300.degree. C. to about 900.degree. C. in a non-oxidizing environment. The composition is useful as a catalyst in reactions catalyzed by acid catalysts.Type: GrantFiled: April 21, 1980Date of Patent: October 6, 1981Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
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Patent number: 4283586Abstract: An aliphatic, cycloaliphatic or aromatic polyol is incorporated in a catalyst of an organoaluminum halide and a nickel compound. The catalyst is used for a dimerization or codimerization of a lower monoolefin to improve a reaction velocity and a stability in the reaction.Type: GrantFiled: April 4, 1980Date of Patent: August 11, 1981Assignee: Nissan Chemical Industries, Ltd.Inventors: Masahito Yoshimura, Satoshi Hoshiyama, Hideki Takamatsu, Hiroshi Kobayashi, Shinichiro Takigawa
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Patent number: 4283305Abstract: Catalyst composition for oligomerizing olefins, obtained by contacting (a) a bivalent nickel compound with (b) a hydrocarbylaluminum compound of the formula AIRCl.sub.2 where R is a monovalent hydrocarbon radical, and (c) a Bronsted acid consisting preferably of a halogenocarboxylic acid of the formula R.sub.1 COOH in which R.sub.1 is a halogenoalkyl radical of the formula C.sub.m H.sub.p X.sub.q, X being halogen, m an integer from 1 to 3, p being zero or an integer and q being an integer, the condition p+q=2m+1 being fulfilled. A preferred Bronsted acid is of the formula R.sub.2 COOH in which R.sub.2 is a halogenomethyl group of the formula CX.sub.n H.sub.3-n, X being halogen and n an integer from 1 to 3.Type: GrantFiled: December 11, 1979Date of Patent: August 11, 1981Assignee: Institut Francais du PetroleInventors: Yves Chauvin, Dominique Commereuc, Jean Gaillard, Gerard Leger, Nhu Hung Phung
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Patent number: 4242531Abstract: Olefins are dimerized in a loop reactor with flashing of the reactor effluent in a flashing zone within the loop. A subsequent flash in a second flashing zone can also be used for the removal of product as flash vapor. In another embodiment, separated product dimers or product heavies are used as absorbents for unreacted ethylene. The use of a vapor-liquid contacting device incorporated in the loop reactor is especially helpful in the dimerization of an olefin when the olefin is available in low-concentration gas streams. A thermosiphon loop reactor can also be used for low-concentration olefin streams to minimize the power requirements as the energy of the feed gas is used to induce the reactor circulation.Type: GrantFiled: August 14, 1978Date of Patent: December 30, 1980Assignee: Phillips Petroleum CompanyInventor: Cecil O. Carter
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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: 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