Partial Patents (Class 585/271)
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Patent number: 6281397Abstract: A catalytic composition effective in the selective hydrogenation of olefinic double bonds, comprising the reaction product between: (A) at least one complex of a transition metal having the following general formula (I): M(R1)(R2)(R3)(R4) (I) wherein: M is selected from titanium and zirconium, preferably titanium; each of the radicals R1, R2, R3 or R4, independently, represents an organic or inorganic group of an anionic nature &sgr;-bound to M, on the condition that at least one, and preferablyat at least two, of these radicals is an organic group; and (B) at least one organometallic compound of magnesium having the following formula (II): Mg(R5)n(R6)(2−n) (II) wherein: R5 or R6 each independently represent an aliphatic or aromatic hydrocarbon group having from 1 to 20 carbon atoms, and “n” is a decimal number between 0 and 2.0.Type: GrantFiled: January 22, 1999Date of Patent: August 28, 2001Assignee: Enichem S.p.A.Inventors: Roberto Santi, Francesco Masi, Gianfranco Longhini
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Patent number: 6239322Abstract: A particulate selective hydrogenation catalyst for hydrogenating unsaturated diolefinic hydrocarbons to &agr;-olefinic hydrocarbons at rates which are at least 1.5 times higher than the rate of hydrogenation of &agr;-olefinic hydrocarbons to saturated compounds contains palladium distributed at the periphery of particles (spherules or extrudates), and at least one element selected from tin and lead. Further, the tin and/or lead is advantageously distributed at the periphery of the spherules or extrudates.Type: GrantFiled: September 17, 1999Date of Patent: May 29, 2001Assignee: Institut Francais du PetroleInventors: Blaise Didillon, Charles Cameron, Christophe Gautreau
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Patent number: 5981818Abstract: A novel process is provided which integrates the cracking of hydrocarbon containing feedstocks with the olefins purification and olefins derivative process utilizing dilute olefin feedstocks.Type: GrantFiled: October 18, 1996Date of Patent: November 9, 1999Assignee: Stone & Webster Engineering Corp.Inventors: David Purvis, Richard H. Mc Cue
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Patent number: 5969202Abstract: A method for producing a cycloolefin and a cycloalkane, which method comprises: a step of hydrogenating a monocyclic aromatic hydrocarbon under an acidic condition in the presence of a catalyst composition, (i) wherein said catalyst composition is a slurry which comprises a ruthenium catalyst, water and zinc sulfate, and which is preserved, prior to being used in said hydrogenation reaction, under a high temperature and high pressure hydrogen atmosphere of from 100 to 200.degree. C. and from 1 to 100 atm for 1 hour or more, and (ii) wherein said hydrogenation reaction is conducted under a controlled pressure, while maintaining a phase separated state of: (a) an oil phase comprising, as main components, the starting materials and the products; and (b) a water phase comprising water as a main component, to thereby control a formation molar ratio of the cycloolefin and the cycloalkane to be formed.Type: GrantFiled: April 2, 1998Date of Patent: October 19, 1999Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Keita Ashida, Mineyuki Iwasaki
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Patent number: 5898091Abstract: For the conversion of an olefinic C.sub.4 or C.sub.5 cut to an alkyl-tertiobutylether or alkyl-tertioamylether and to propylene, by metathesis, the process comprises four successive steps: (1) selective hydrogenation of the diolefins with simultaneous isomerisation of the alpha olefins to internal olefins; (2) etherification of the isoolefins; (3) elimination of oxygen-containing impurities; (4) metathesis of internal olefins with ethylene. The process has application, e.g., to C.sub.4 and C.sub.5 steam cracking cuts.Type: GrantFiled: May 10, 1996Date of Patent: April 27, 1999Assignee: Institut Francais du PetroleInventors: Jean-Alain Chodorge, Dominique Commereuc, Jean Cosyns, Didier Duee, Bernard Torck
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Patent number: 5817901Abstract: A process for the selective hydrogenation of a fraction of hydrocarbons containing 2 to 20 carbon atoms and comprising monounsaturated olefinic hydrocarbons and/or aromatic compounds and at least one polyunsaturated hydrocarbon from the group formed by acetylenic compounds and dienes, in which the hydrocarbon fraction, which is at least partially in the liquid phase, circulates with hydrogen in a given direction in a reactor containing at least one fixed bed of a hydrogenation catalyst in the form of a divided solid, characterized in that said reactor is provided with at least one inlet conduit for a fluid mixture comprising said hydrocarbon fraction and hydrogen and at least one outlet conduit for the hydrogenated hydrocarbon fraction, and in that it comprises at least one static mixer upstream of said outlet for the hydrogenated hydrocarbon fraction.Type: GrantFiled: September 7, 1995Date of Patent: October 6, 1998Assignee: Institut Francais du PetroleInventors: Pierre Trambouze, Jean-Paul Euzen, Gerard Leger, Henri Delhomme
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Patent number: 5777186Abstract: A process for selectively hydrogenating benzene in a hydrocarbon oil is disclosed. The process comprises reacting the hydrocarbon oil with hydrogen gas in the presence of a hydrogenation catalyst comprising at least one metal in Group VIII of the Periodic Table and an alkaline aqueous layer which contains zinc or a zinc compound. Benzene in hydrocarbon oils can be selectively converted into cyclohexane by the process, while suppressing the hydrogenation reaction of alkyl aromatic compounds which are important high octane materials for gasoline.Type: GrantFiled: October 6, 1997Date of Patent: July 7, 1998Assignees: Cosmo Research Institute, Cosmo Oil Co., Ltd.Inventor: Toshio Shimizu
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Patent number: 5698752Abstract: A selective hydrogenation of an alkyne in an olefin-containing fluid is provided which comprises contacting the fluid and hydrogen gas with a catalyst in the presence of at least one sulfur compound, under reaction conditions effective to produce at least one alkene wherein the catalyst comprises at least one alkali metal, fluorine and an inorganic support material.Type: GrantFiled: July 23, 1996Date of Patent: December 16, 1997Assignee: Phillips Petroleum CompanyInventors: Scott H. Brown, James B. Kimble, Stan A. Zisman
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Patent number: 5656761Abstract: A method for pretreating a slurry containing a ruthenium catalyst for use in the continuous partial hydrogenation of monocyclic aromatic hydrocarbons is disclosed. In this method, the above-mentioned slurry is heat-treated at a temperature of from 60.degree. to 180.degree. C. for at least 10 minutes while agitating. By using the pretreated catalyst slurry in the above-mentioned continuous partial hydrogenation, partial hydrogenation reaction products can be efficiently obtained without suffering from the excess mixing of the components of the catalyst slurry into an oil phase containing the partial hydrogenation reaction products, thereby enabling operations and facilities required for separation to be simplified.Type: GrantFiled: May 16, 1994Date of Patent: August 12, 1997Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hajime Nagahara, Koji Nakagawa
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Patent number: 5639927Abstract: A process of producing cycloolefin, comprises the step of subjecting a monocyclic aromatic hydrocarbon to partial hydrogenation reaction in the presence of water and a ternary catalyst containing (a) ruthenium, (b) zinc and (c) at least one selected from the group consisting of gold, silver and copper.Type: GrantFiled: December 18, 1995Date of Patent: June 17, 1997Assignee: Mitsubishi Chemical CorporationInventors: Toshiyuki Suzuki, Tatsuya Ezaki
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Patent number: 5589600Abstract: A process for the preparation of cyclohexene by partial hydrogenation of benzene with hydrogen in the presence of water and ruthenium catalysts modified with nickel, at elevated temperature in the liquid phase, wherein alloys of ruthenium with nickel are used as catalysts.Type: GrantFiled: May 25, 1995Date of Patent: December 31, 1996Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Roman Dostalek, Laszlo Marosi
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Patent number: 5583274Abstract: C.sub.2 -C.sub.6 alkynes (preferably acetylene) contained in feeds which also contain sulfur impurities are hydrogenated to the corresponding alkenes in the presence of a supported palladium catalyst which has been promoted with alkali metal fluoride (preferably potassium fluoride).Type: GrantFiled: January 20, 1995Date of Patent: December 10, 1996Assignee: Phillips Petroleum CompanyInventors: Tin-Tack P. Cheung, Marvin M. Johnson
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Patent number: 5569803Abstract: A method for producing a cycloolefin, which comprises partially hydrogenating a monocyclic aromatic hydrocarbon in the presence of water and a ruthenium catalyst supported on silica modified by zirconium oxide.Type: GrantFiled: December 23, 1994Date of Patent: October 29, 1996Assignee: Mitsubishi Chemical CorporationInventors: Takahiko Takewaki, Naoko Fujita, Toshiharu Yokoyama, Takao Maki
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Patent number: 5569802Abstract: The present invention relates to a catalyst for the selective hydrogenation of an unsaturated compound, based on a noble metal and/or a noble-metal oxide on an aluminum oxide support, and to a process for the preparation of the catalyst. The present invention further relates to a process for the selective hydrogenation of unsaturated compounds.Type: GrantFiled: September 28, 1994Date of Patent: October 29, 1996Assignee: Huels AktiengesellschaftInventors: Hans-Gerd L uken, Lothar Fischer, Wilhelm Droste, Bernd Nowitzki
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Patent number: 5491233Abstract: A catalytic asymmetric reduction process, which, by hydrogenating trisubstituted olefins, yields a corresponding organic compound having a high level of enantiomeric purity is disclosed. The process is also effective for the catalytic asymmetric reduction of certain enamines and related compounds to yield a corresponding amine or related compound, respectively, having a high level of enantiomeric purity. The reduction process utilizes a chiral metal catalyst that includes a metal or metal complex that is selected from groups 3, 4, 5, or 6, lanthanides and actinides. Moreover, the process uses hydrogen as the stoichiometric reducing agent and may be carried out at pressures ranging from about 0.5 to 200 atmospheres. The reaction can also be carried out using an acidic compound as a rate enhancing additive.Type: GrantFiled: July 12, 1994Date of Patent: February 13, 1996Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Richard D. Broene, Nancy E. Lee
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Patent number: 5475173Abstract: A supported catalyst composition, which is effective as a diolefin hydrogenation catalyst, comprises palladium, silver and alkali metal fluoride. This catalyst composition is employed in the selective hydrogenation of C.sub.4 -C.sub.10 diolefins (preferably 1,3-butadiene) with hydrogen gas to the corresponding monoolefins.Type: GrantFiled: July 19, 1994Date of Patent: December 12, 1995Assignee: Phillips Petroleum CompanyInventors: Tin-Tack P. Cheung, Marvin M. Johnson
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Patent number: 5475172Abstract: Di-addended and tetra-addended Buckminster fullerenes are synthesized through the use of novel organoborane intermediates. The C.sub.60, C.sub.70, or higher fullerene is reacted with a borane such as BH.sub.3 in a solvent such as toluene to form an organoborane intermediate. Reaction of the organoborane such as hydrolysis with water or alcohol results in the product di-addended and tetra-addended fullerene in up to 30% yields. Dihydrofullerenes and tetrahydrofullerenes are produced by the process of the invention.Type: GrantFiled: December 1, 1993Date of Patent: December 12, 1995Assignee: Sandia CorporationInventors: Paul A. Cahill, Craig C. Henderson
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Patent number: 5475174Abstract: The invention concerns a process for the selective hydrogenation of polyunsaturated cyclic compounds comprising at least one endocyclic carbon-carbon double bond and at least one terminal exocyclic carbon-carbon double bond, said double bonds not being conjugated, to form a mixture essentially containing the saturated ring compound and comprising at least one terminal exocyclic double bond, the process being carried out in the presence of hydrogen under a pressure of from 1 to 10 MPa and at a temperature of from 0.degree. to 200.degree. C., and in the presence of a catalyst including a support and (a) from 0.1 to 5% by weight of at least one metal from group VIII (iridium, osmium, nickel, palladium, platinum and rhodium) and (b) from 0.01 to 15% by weight of at least one metal from group IVa (tin, germanium and lead), the molar ratio between metals of group VIII and group IVa being between 0.3 and 3. The process is used for the hydrogenation of 4-vinylcylcohexene to vinylcyclohexane.Type: GrantFiled: November 24, 1993Date of Patent: December 12, 1995Assignee: Institut Francais du PetroleInventors: Christine Lucas, Jean-Pierre Candy, Jean-Marie Basset, Blaise Didillon, Jean-Paul Boitiaux
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Patent number: 5414171Abstract: This is a catalyst and a process for partially hydrogenating polycyclic and monocyclic aromatic hydrocarbons such as benzene, naphthalenes, biphenyls, and alkylbenzenes to produce the corresponding cycloolefins. The catalyst is a hydrogenation catalyst comprising ruthenium and a promoter metal, such as cobalt, on a composite support. It is a process in which the product cycloolefin is produced in high yield and with high selectivity.Type: GrantFiled: February 26, 1992Date of Patent: May 9, 1995Assignee: Catalytica, Inc.Inventors: Michael A. Richard, Jacques C. De Deken, David K. Yee
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Patent number: 5334790Abstract: This is a catalyst and a process for partially hydrogenating polycyclic and monocyclic aromatic hydrocarbons such as benzene, naphthalenes, biphenyls, and alkylbenzenes to produce the corresponding cycloolefins. The catalyst is a hydrogenation catalyst comprising ruthenium on a composite support. It is a process in which the product cycloolefin is produced in high yield and with high selectivity.Type: GrantFiled: February 26, 1992Date of Patent: August 2, 1994Assignee: CatalyticaInventors: Michael A. Richard, Jacques De Deken, David K. Yee
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Patent number: 5264641Abstract: There is provided a method for hydrogenating aromatics with a catalyst comprising a crystalline ultra-large pore oxide material. The catalyst also comprises a hydrogenation metal, such as palladium. The process may be used to saturate benzene to form cyclohexane.Type: GrantFiled: December 14, 1992Date of Patent: November 23, 1993Assignee: Mobil Oil Corp.Inventors: William S. Borghard, Cynthia T. Chu, Thomas F. Degnan, Stuart S. Shih
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Patent number: 5256163Abstract: The present invention provides a flow liquid-phase chemical reaction system in which a high pressure reservoir unit holds a solvent solution which contains an organic reactant and a gas reactant. The quantity of gas reactant dissolved in the solvent solution is determined by the level of gas reactant vapor pressure in the reservoir unit. The solvent solution is passed through a solid catalyst reactor unit to achieve a selective reaction between the two reactant components of the solvent solution.Type: GrantFiled: September 11, 1991Date of Patent: October 26, 1993Assignees: Philip Morris Incorporated, Philip Morris Products Inc.Inventors: Robert L. Augustine, Glen Wolosh
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Patent number: 5254761Abstract: A reducible unsaturated organic compound is reduced with diimide in an aqueous emulsion comprised of water, an organic phase which contains the compound to be reduced, and an effective stabilizing amount of an anionic surfactant. The organic compound is preferably an unsaturated organic compound containing a carbon-to-carbon multiple bond, which is preferably a carbon-to-carbon double bond. Diimide is formed by reaction of hydrazine with an oxidant in the aqueous emulsion described above. The preferred oxidant is hydrogen peroxide. A product is obtained in high yield and purity in most cases. This process is especially useful for the selective reduction of a compound having two or more carbon-to-carbon double bonds of different reactivities or a carbon-to-carbon double bond and a functionality (e.g., an O--O or S--S linkage) which is reducible by catalytic hydrogenation but not diimide.Type: GrantFiled: May 18, 1992Date of Patent: October 19, 1993Assignee: The Goodyear Tire & Rubber CompanyInventor: Dane K. Parker
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Patent number: 5233110Abstract: A process for the preparation of cyclooctene which comprises irradiating 1,5-cyclooctadiene with light in the presence of a photodehydrogenation catalyst, acetone and an alcohol to partially hydrogenate the 1,5-cyclooctadiene.Type: GrantFiled: February 28, 1992Date of Patent: August 3, 1993Assignee: Agency of Industrial Science & TechnologyInventors: Taka-aki Hanaoka, Yoshihiro Sugi, Takehiko Matsuzaki, Kazuhiko Takeuchi, Hironori Arakawa
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Patent number: 5227553Abstract: A process for the selective hydrogenation of butadiene to butenes in the liquid phase or trickle phase in contact with a fixed-bed supported noble metal catalyst, wherein a high-butadiene C.sub.4 stream having a butadiene content of from 20 to 80% w/w, based on the weight of the C.sub.4 stream, is hydrogenated in a cascade of two reaction zones such that the hydrogenation product from the first reaction zone has a butadiene content of from 0.1 to 20% w/w and the hydrogenation product from the second reaction zone has a butadiene content of from 0.005 to 1% w/w, based in both cases on the weight of the C.sub.4 stream, provided that the butadiene content of the hydrogenation product from the second reaction zone is at least 5 times smaller than that of the hydrogenation product from the first reaction zone.Type: GrantFiled: May 22, 1992Date of Patent: July 13, 1993Assignee: BAST AktiengesellschaftInventors: Peter Polanek, Dietmar Posselt, Peter Schreyer
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Patent number: 5171907Abstract: A cobalt carbonyl phosphine complex useful for hydrogenation of cyclic polyenes to corresponding cyclic monoenes is prepared by reaction of dicobalt carbonyl and a phosphine compound in at least one non-oxygenated aliphatic solvent. Selective hydrogenation of the cyclic polyenes comprises an induction period during which the polyenes are contacted with the cobalt carbonyl complex catlayst under hydrogen pressure followed by decreasing the reaction temperature and pressure for a period of time sufficient to complete the hydrogenation.Type: GrantFiled: July 1, 1991Date of Patent: December 15, 1992Assignee: Phillips Petroleum CompanyInventors: Michael S. Matson, Stan A. Zisman
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Patent number: 5157179Abstract: A method for producing a cycloolefin which comprises partially hydrogenating an aromatic hydrocarbon with hydrogen in a liquid phase in the presence of water and a catalyst having as main component ruthenium supported on a carrier, to form the corresponding cycloolefin, wherein an oxide with the total pore volume of pores having radii of from 20 to 100,000 .ANG. being from 0.3 to 10 cc/g and with the volume of pores having radii of from 20 to 200 .ANG. constituting at most 15% of the total pore volume, is used as the carrier for the catalyst.Type: GrantFiled: July 5, 1991Date of Patent: October 20, 1992Assignee: Mitsubishi Kasei CorporationInventors: Tohru Setoyama, Takahiko Takewaki, Takao Maki
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Patent number: 4908420Abstract: A method for preparing a resin having light color comprises the steps of: hydrogenating a compound represented by the formula (1) ##STR1## wherein l, m and n are integers of 0.ltoreq.l.ltoreq.3, 0.ltoreq.m.ltoreq.8 and l.ltoreq.n.ltoreq.3, respectively, and R.sup.1 and R.sup.6 each represent a hydrogen atom or a hydrocarbon residue having 1 to 3 carbon atoms, with or without R.sup.5 and R.sup.6 forming a ring, in the presence of a Ziegler catalyst containing a transition metal compound of the groups IV to VI of the Periodic Table and an organometallic compound of the groups I to III of the Periodic Table in combination to obtain a norbornene compound represented by the formula (2) ##STR2## wherein l, m, n and R.sup.1 and R.sup.6 are the same as above; and polymerizing the norbornene compound to give the resin having light color.Type: GrantFiled: July 21, 1989Date of Patent: March 13, 1990Assignee: Nippon Oil Company, Ltd.Inventors: Makoto Sasaki, Yukio Kobayashi, Shozo Tsuchiya
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Patent number: 4891456Abstract: A method for preparing a norbornene structure compound comprises hydrogenating a compound represented by the formula of ##STR1## wherein l, m and n are integers of 0.ltoreq.l.ltoreq.3, 0.ltoreq.m.ltoreq.8 and 1.ltoreq.n.ltoreq.3, respectively, and each of R.sup.1 to R.sup.6 is a hydrogen atom or a hydrocarbon residue having 1 to 3 carbon atoms with or without R.sup.6 forming a ring with R.sup.4 or R.sup.5, in the presence of a Ziegler type catalyst containing in combination a compound of a transition metal of Groups IV to VI of the periodic table and an organometallic compound of Groups I to III of the periodic table, to thereby convert the compound of the formula (1) into a compound represented by the following formula of ##STR2## wherein l, m and n are the same as above.Type: GrantFiled: June 30, 1988Date of Patent: January 2, 1990Assignee: Nippon Oil Co., Ltd.Inventors: Hitoshi Yuasa, Mitsuo Matsuno, Tetsuo Satoh
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Patent number: 4748290Abstract: Novel alumina-supported nickel boride catalysts prepared by the borohydride promoted reduction of nickel arsenate are described. Method of catalyst preparation and process for hydrogenation of acetylenic and diolefinic compounds employing the invention catalysts are also described.Type: GrantFiled: October 5, 1987Date of Patent: May 31, 1988Assignee: Phillips Petroleum CompanyInventor: Ted H. Cymbaluk
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Patent number: 4727202Abstract: Catalytically-active metallic glasses containing at least one element from a subgroup of the periodic system and at least one element from a main group of the periodic system. Process for the production of catalytically-active metallic glasses where the metallic glass is produced from at least one element from a subgroup of the periodic system and at least from one element from a main group of the periodic system. The metallic glasses are activated by self-activation or by an oxidative and/or reductive treatment. The catalytically-active metallic glasses can be used as hydrogenation, oxidation or isomerization catalysts.Type: GrantFiled: May 18, 1987Date of Patent: February 23, 1988Assignee: Lonza Ltd.Inventors: Volker Franzen, Hans-Joachim Guntherodt, Alfons Baiker, Erich Armbruster, Halim Baris
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Patent number: 4705906Abstract: Ethylene is produced by the selective hydrogenation of acetylene in the presence of carbon monoxide at a concentration of greater than 1% vol, generally greater than 5% vol, and optionally also ethylene by contact at an elevated temperature in the range from 100.degree. to 500.degree. C. with a catalyst comprising a metal oxide or sulphide or mixture of metal oxides or sulphides having hydrogenation activity, for example ZnO either alone or in combination with other metal oxides or sulphides.Type: GrantFiled: November 12, 1986Date of Patent: November 10, 1987Assignee: The British Petroleum Company, p.l.c.Inventors: John H. Brophy, Anthony Nock
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Patent number: 4678861Abstract: A process for producing a cycloolefin which comprises partially hydrogenating a monocyclic aromatic hydrocarbon in the presence of a ruthenium catalyst composed of a rare earth element compound solid carrier and a ruthenium component supported thereon. The resulting cycloolefin is obtained in high yield and high selectivity and the catalyst can be repeatedly used for a prolonged period of time.Type: GrantFiled: October 23, 1985Date of Patent: July 7, 1987Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Osamu Mitsui, Yohei Fukuoka
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Patent number: 4673714Abstract: An olefin hydrogenation catalyst containing as an essential component a compound represented by the formula: ##STR1## The catalyst is capable of selectively hydrogenating the unsaturated double bonds of the diene units of a conjugated diene polymer or copolymer having a number average molecular weight of 500 to 1,000,000, particularly a styrenebutadiene block copolymer comprising at least one polymer block A composed mainly of styrene and at least one polymer block B composed mainly of 1,3-butadiene and/or isoprene. The hydrogenated block copolymer obtained from such selective hydrogenation is useful as an elastomer, a thermoplastic elastomer or a thermoplastic resin having excellent weather resistance and oxidation resistance.Type: GrantFiled: April 10, 1985Date of Patent: June 16, 1987Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Yasushi Kishimoto, Tetsuo Masubuchi
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Patent number: 4613714Abstract: Catalyst for the selective hydrogenation of multi-unsaturated organic compounds, in particular of diolefins and dienes in mixtures with other hydrocarbons; the catalyst is characterized by(A) a metal component from one or more elements of Group VIII of the Periodic Table on(B) a support material on the basis(b.sub.1) of one or more n-semiconducting oxides of one or more elements from the Subgroups IVb, Vb and VIb of the Periodic Table or of thorium or cerium, or respectively on the basis(b.sub.2) of one or more n-semiconducting mixed oxide systems of the formula Me.sub.2 Me.sub.1 (0).sub.x, where Me.sub.1 is an element of the group defined in (b.sub.1), Me.sub.2 an alkaline earth metal or an element different from Me.sub.1 or the group defined in (b.sub.1), and x signifies the number of oxygen atoms required for the saturation of Me.sub.1 and Me.sub.Type: GrantFiled: October 8, 1985Date of Patent: September 23, 1986Assignee: Sud-Chemie AktiengesellschaftInventors: Karl-Heinz Stadler, Karel Kochloefl
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Patent number: 4590319Abstract: A method for the partial hydrogenation of conjugated dienes, characterized in that a chain conjugated diene in which the conjugated two double bonds have different numbers of substituents, is hydrogenated at a temperature of not higher than 50.degree. C. in the presence of a catalyst composed essentially of (1) a cobalt compound, (2) an organophosphine compound and (3) an aluminum compound, to obtain a partially hydrogenated product wherein as between said conjugated two double bonds, the one having a greater number of substituents is selectively hydrogenated.Type: GrantFiled: February 26, 1985Date of Patent: May 20, 1986Assignee: Mitsubishi Chemical Industries, Ltd.Inventors: Naoshi Imaki, Yoshiko Fukumoto
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Patent number: 4533752Abstract: Olefins are produced by containing an organic compound having at least one benzene ring with ethylenediamine and calcium metal, the calcium metal being used in large excess or alternatively in conjunction with an inert abrasive particulate substance. Substantially all of the organic compounds are converted to corresponding cyclic olefins, largely mono-olefins.Type: GrantFiled: August 23, 1984Date of Patent: August 6, 1985Assignee: Purdue Research FoundationInventors: Robert A. Benkeser, James A. Laugal, Angela Rappa
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Patent number: 4533760Abstract: Olefins are produced by contacting an organic compound having at least one benzene ring with calcium metal, ethylenediamine, a low molecular weight aliphatic alcohol, and optionally a low molecular weight aliphatic primary amine, and/or an inert, abrasive particulate substance. The reduction is conducted at temperatures ranging from about -10.degree. C. to about 30.degree. C. or somewhat higher. Substantially all of the organic compounds are converted to corresponding cyclic olefins, primarily diolefins.Type: GrantFiled: August 23, 1984Date of Patent: August 6, 1985Assignee: Purdue Research FoundationInventors: Robert A. Benkeser, James A. Laugal, Angela Rappa
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Patent number: 4390741Abstract: This invention discloses a process for the separation of diisopropenylbenzene from organic impurities in a dehydrogenation mixture comprising: (1) hydrogenating said dehydrogenation mixture to a maximum isopropenylstyrene concentration of no more than about 5% by weight in the presence of a rhodium catalyst and hydrogen to form a hydrogenated dehydrogenation mixture, followed by, (2) fractionally distilling said hydrogenated dehydrogenation mixture under conditions sufficient to separate said diisopropenylbenzene from said organic impurities in said hydrogenated dehydrogenation mixture.Type: GrantFiled: September 3, 1982Date of Patent: June 28, 1983Assignee: The Goodyear Tire & Rubber CompanyInventors: Howard A. Colvin, Joel Muse, Jr.
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Patent number: 4345105Abstract: Methylacetylene is removed prior to unduly raising its temperature from a stream containing the same but thus to minimize any danger of violent decomposition or explosion or coke formation. In one embodiment, a stream is obtained from the cracking of propane to produce ethylene, is fractionated to obtain a concentrate of methylacetylene and any propadiene which may be present, the concentrate is subjected to hydrogenation, thus converting methylacetylene and propadiene to propylene and the propylene is recovered.Type: GrantFiled: August 12, 1980Date of Patent: August 17, 1982Assignee: Phillips Petroleum CompanyInventor: David L. Rogers
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Patent number: 4313017Abstract: Polynuclear aromatic reactants are selectively hydrogenated in the presence of hydrogen gas with a zinc titanate catalyst.Type: GrantFiled: December 29, 1980Date of Patent: January 26, 1982Assignee: Phillips Petroleum Co.Inventors: Roger N. McGinnis, Lloyd E. Gardner, Floyd Farha, Jr.
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Patent number: 4251674Abstract: In an ethylene manufacturing process in which the effluent from the cracking furnaces is provided to an acetylene reactor to therein selectively hydrogenate acetylene to ethylene, method and apparatus is provided whereby methanol is injected into the cracking furnace to produce carbon monoxide in sufficient quantities to substantially optimize the selectivity of the conversion of acetylene to ethylene in the acetylene reactors. The concentration of the carbon monoxide in the effluent flowing from the cracking furnace is utilized to manipulate the flow of methanol to the cracking furnace so as to maintain a desired concentration of carbon monoxide in the effluent flowing from the cracking furnace.Type: GrantFiled: October 22, 1979Date of Patent: February 17, 1981Assignee: Phillips Petroleum CompanyInventors: Ricardo J. Callejas, John R. Mitchell
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Patent number: 4204081Abstract: There is disclosed a process for the preparation of cyclopentene which comprises selectively hydrogenating cyclopentadiene in a liquid phase by contacting cyclopentadiene with hydrogen in the presence of a hydrogenation catalyst comprising (1) a soluble nickel compound, (2) an organoaluminum compound or a lithium alkyl compound, and (3) at least one cocatalyst compound selected from the group consisting of H.sub.2 O; NH.sub.3 ; ROH where R is an alkyl or a halogenated alkyl radical containing from 1 to 20 carbon atoms; ##STR1## where R.sub.1, R.sub.2 and R.sub.3 may be hydrogen, or an alkyl radical containing from 1 to 6 carbon atoms; ##STR2## where R.sub.1, R.sub.2 and R.sub.3 may be hydrogen or halogen, or an alkyl radical containing from 1 to 6 carbon atoms; R.sub.1 O R.sub.2 wherein R.sub.1 and R.sub.2 may be the same or different alkyl radicals containing from 1 to 6 carbon atoms; and ##STR3## wherein R.sub.1 may be alkyl or an aromatic radical containing from 1 to 8 carbon atoms and R.sub.Type: GrantFiled: August 30, 1978Date of Patent: May 20, 1980Assignee: The Goodyear Tire & Rubber CompanyInventor: Henry R. Menapace