Plural Metal Or Nonhalide Cu Compound-containing Patents (Class 585/848)
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Patent number: 7938955Abstract: Provided are a method for producing a super-low sulfur gas oil blending component or a super-low sulfur gas oil composition having a sulfur content of less than 5 mass ppm, under relatively mild conditions, without greatly increasing the hydrogen consumption and without remarkably decreasing the aromatic content; and a super-low sulfur gas oil composition having a sulfur content of less than 5 mass ppm which exhibits a high heating value, is excellent in fuel economy and output power, and is free from an adverse effect on a sealing rubber member or the like used in the fuel injection system and thus does not cause the leakage of a fuel. A method for producing a super-low sulfur gas oil blending component or a super-low sulfur gas oil composition having a sulfur content of less than 5 mass ppm is also disclosed.Type: GrantFiled: December 21, 2005Date of Patent: May 10, 2011Assignee: Japan Energy CorporationInventors: Yasuhiro Araki, Katsuaki Ishida
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Patent number: 7411107Abstract: A process for the oxidation of a C2 to C4 alkane to produce the corresponding alkene and carboxylic acid which process comprises separation of the alkene from a mixture of the alkene, the alkane and oxygen by absorption in a metallic salt solution, and recovery of an alkene-rich stream from the metallic salt solution. Integrated processes for the production of alkyl carboxylate and alkenyl carboxylate, which processes comprise oxidation of a C2 to C4 alkane to produce the corresponding alkene and carboxylic acid, separation of the alkene from a mixture of the alkene, the alkane and oxygen by absorption in a metallic salt solution, and recovery of an alkene-rich stream from the metallic salt solution for use in production of alkyl carboxylate or alkenyl carboxylate.Type: GrantFiled: February 12, 2003Date of Patent: August 12, 2008Assignee: BP Chemicals LimitedInventor: Andrew Richard Lucy
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Patent number: 7361800Abstract: Chitosan membranes chelated with silver or cuprous material may be used to separate olefins from a mixture of olefins and paraffins. The feed stream is humidified, demisted, treated to remove sulfur compounds and passed to a cell having a chitosan membrane containing chelated silver or cuprous compounds. The process has a reasonable flux rate and is operable at reasonable temperatures and pressures. The process could be used in an olefin separation train.Type: GrantFiled: April 5, 2004Date of Patent: April 22, 2008Assignee: Monteco Ltd.Inventors: Patricio S. Herrera, Xianshe Feng, John Donald Payzant, Jeong-Hoon Kim
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Patent number: 7019188Abstract: The present invention relates to the separation of olefins, diolefins and lower aromatics from mixed streams of hydrocarbons using ionic liquids in the absence of metal compounds. The present invention eliminates the metal complexes conventionally used in such separation and thus reduces the complexity of the process.Type: GrantFiled: June 14, 2002Date of Patent: March 28, 2006Assignee: Nova Chemicals (International) S.A.Inventors: Ronald Scott Smith, Patricio S Herrera, Sean Reynolds
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Patent number: 6395952Abstract: The present invention provides a method for recovering high purity olefins from cracked gas effluents or other paraffin/olefin gaseous mixtures by use of a chemical absorption process.Type: GrantFiled: August 16, 1996Date of Patent: May 28, 2002Assignee: Stone & Webster Process Technology, Inc.Inventor: Richard Barchas
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Patent number: 6339182Abstract: Methods for separating olefins from non-olefins, such as parafins, including cycloparaffins, oxygenates and aromatics, are provided. The methods use metal salts to complex olefins, allowing the non-olefins to be separated by a variety of methods, including decantation and distillation. The metal salts are dissolved in ionic liquids, which tend to have virtually no vapor pressure, and which poorly solubilize the non-olefins. Accordingly, the non-olefins phase separate well, and can be distilled without carrying over any of the ionic liquid into the distillate. Preferred salts are Group IB salts, more preferably silver salts. A preferred silver salt is silver tetrafluoroborate. Preferred ionic liquids are those which form stable solutions or dispersions of the metal salts, and which do not dissolve the non-olefins. Further, if the olefins are subject to isomerization, the ionic liquid is preferably relatively non-acidic.Type: GrantFiled: December 12, 2000Date of Patent: January 15, 2002Assignee: Chevron U.S.A. Inc.Inventors: Curtis L. Munson, Laura C. Boudreau, Michael S. Driver, William L. Schinski
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Patent number: 6042798Abstract: A method for the desulfurization of hydrocarbons by desulfurizing unsaturated hydrocarbons or hydrocarbon materials containing unsaturated hydrocarbons, in the presence or absence of hydrogen, using a copper-zinc desulfurizing agent prepared by the co-precipitation method. By this method, the sulfur content of the hydrocarbons can be reduced while suppressing hydrogenation of the unsaturated hydrocarbons.Type: GrantFiled: January 21, 1997Date of Patent: March 28, 2000Assignee: Osaka Gas Company LimitedInventors: Masataka Masuda, Osamu Okada, Takeshi Tabata, Yasuhiro Hirai, Hiroki Fujita
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Patent number: 5866749Abstract: Sulfur and mercaptans in reactive hydrocarbon streams are removed by contacting the hydrocarbons at mild temperatures with a hydrogen reduced metal oxide such as a hydrogen reduced copper, zinc and/or aluminum oxide.Type: GrantFiled: January 22, 1997Date of Patent: February 2, 1999Assignee: Exxon Chemical Patents Inc.Inventor: Di-Yi (John) Ou
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Patent number: 5859304Abstract: The present invention provides an improved method for recovering high purity olefins from cracked gas effluents or other parafin/olefin gaseous mixtures by use of a chemical absorption process.Type: GrantFiled: December 13, 1996Date of Patent: January 12, 1999Assignee: Stone & Webster Engineering Corp.Inventors: Richard Barchas, Richard McCue, Jr., Christopher Wallsgrove, Mark Whitney
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Patent number: 5639935Abstract: Ethylene and propylene are recovered from a mixture thereof with other hydrocarbons by: (a) feeding the mixture to a separation zone with a top and a bottom; (b) feeding to the top above the mixture an aqueous complexing solution to form Cu(I) complexes of ethylene and propylene; (c) feeding below the mixture ethylene to strip propylene from the propylene complex; (d) removing from the bottom below the stripping gas a first liquid stream containing the Cu (I) ethylene complex; (e) recovering ethylene from the Cu(I) complex using reduced pressure and/or elevated temperature; (f) removing from the separation zone between the the gaseous mixture and the complexing solution, a second liquid stream comprising Cu (I) propylene complex; (g) recovering propylene from the Cu(I) complex and producing a liquid recycle stream comprising copper (I) salt; and (h) recycling the liquid recycle stream from step (g) to the separation zone.Type: GrantFiled: September 7, 1995Date of Patent: June 17, 1997Assignee: BP Chemicals LimitedInventors: Jeremy Bernard Cooper, Karen Small
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Patent number: 5625116Abstract: The carbon monoxide contained in .alpha.-olefins and saturated hydrocarbons, in particular .alpha.-olefins and C.sub.2-4 saturated hydrocarbons, is removed, by contacting such .alpha.-olefins and saturated hydrocarbons, at a temperature ranging from 0.degree. to 150.degree. C., with a catalyst system comprising a mixture and/or the reaction product of:A) one or more oxides of metals selected from the group consisting of Cu, Fe, Ni, Co, Pt, Pd; andB) one or more oxides of metals selected from the group consisting of metals of groups V B, VI B, or VII B of the Periodic Table;thus reducing the content of carbon monoxide to values lower than 0.03 ppm.Type: GrantFiled: June 1, 1995Date of Patent: April 29, 1997Assignee: Montell North America Inc.Inventors: Roberto Flammini, Giovanni Patroncini
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Patent number: 5523512Abstract: Complexing reagents are provided which comprise Cu(I) carboxylates or Cu(I) sulfonates and high molecular weight olefins. The invention complexing reagents are useful for separating olefins from mixtures of olefins and paraffins.Type: GrantFiled: June 24, 1993Date of Patent: June 4, 1996Assignee: Phillips Petroleum CompanyInventors: Ted H. Cymbaluk, Gerhard P. Nowack, Marvin M. Johnson
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Patent number: 5516966Abstract: A method for preparing cuprous carboxylates (Cu(I) carboxylates) is provided wherein Cu(II) carboxylates are reacted with copper powder in an aromatic solvent under a reducing atmosphere, optionally in the presence of at least one of a carboxylic acid or carboxylic acid anhydride. Also, a method for preparing desired Cu(II) carboxylates is provided wherein a Cu(II) carboxylate having fewer carbon atoms is reacted with a carboxylic acid corresponding to the desired Cu(II) carboxylate. The invention method reactions achieve good conversions with rapid rates of reaction. The Cu(I) carboxylates produced according to the invention method are useful as reagents or in the preparation of olefin complexing reagents.Type: GrantFiled: June 5, 1995Date of Patent: May 14, 1996Assignee: Phillips Petroleum CompanyInventors: Gerhard P. Nowack, Marvin M. Johnson, Ted H. Cymbaluk
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Patent number: 5446232Abstract: Disclosed is a method and apparatus for removing oxygen from hydrogen, hydrocarbon, or halogenated hydrocarbon gas which contains about 0.01 to about 10 mole % oxygen. The oxygen removal is accomplished by contacting the gas with a Hopcalite catalyst at a temperature of about 100.degree. to about 300.degree. C. The invention can be part of a process for making 1,2-dichloroethane where, in a first reaction, ethane and chlorine are reacted to make ethylene and hydrogen chloride and, in a second reaction, the ethylene and hydrogen chloride are reacted with excess oxygen to make the 1,2-dichloroethane. The unreacted ethane can be recycled to the first step after the method of the invention is applied to remove the oxygen.Type: GrantFiled: February 14, 1994Date of Patent: August 29, 1995Assignee: Occidental Chemical CorporationInventors: Hang-Chang B. Chen, Deborah J. Olsen
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Patent number: 5245106Abstract: The invention relates to a method of eliminating mercury or arsenic from a fluid in the presence of a solid mass for the recovery of mercury and/or arsenic. The said mass contains copper and sulphur at least partly in the form of copper sulphide and results (a) from the incorporation of a copper compound other than a sulphide into a solid mineral support, (b) possible calcination of the product obtained in stage (a), and from bringing the product obtained previously into contact with elementary sulphur and (d) a heat treatment.Type: GrantFiled: October 30, 1991Date of Patent: September 14, 1993Assignee: Institut Francais du PetroleInventors: Charles Cameron, Philippe Courty, Jean-Paul Boitiaux, Philipe Varin, Gerard Leger
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Patent number: 5202521Abstract: A selective absorption process for separating C.sub.2 -C.sub.4 alkenes (in particular ethylene) from C.sub.1 -C.sub.5 alkanes with a liquid extractant comprising dissolved copper(I) compound(s), in particular dissolved Cu(I) hydrocarbonsulfonate(s), is carried out in a one-column operation, wherein an overhead product is withdrawn which contains alkene(s) at a lower concentration than the feed, a side product is withdrawn which contains alkene(s) at a higher concentration than the feed, and a bottoms stream is withdrawn which contains primarily the liquid extractant.Type: GrantFiled: June 5, 1992Date of Patent: April 13, 1993Assignee: Phillips Petroleum CompanyInventors: Ronald E. Brown, Robert L. Hair
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Patent number: 5191153Abstract: Olefin complexing reagents comprising Cu(I) carboxylate/BF, adducts in aromatic solvents and a method of preparation therefor, and use of said reagents in the separation of olefins from paraffins are provided.Type: GrantFiled: November 4, 1991Date of Patent: March 2, 1993Assignee: Phillips Petroleum CompanyInventors: Ted H. Cymbaluk, Donald C. Tabler, Marvin M. Johnson, Gerhard P. Nowack
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Patent number: 4691074Abstract: A compound, monochloro biphenyl: CuAlCl.sub.4, has been isolated and proven to exist. Monochloro biphenyl can be any one of the possible three isomers, ortho, meta and para or can be any mixture of the three isomers.An improved process is provided for the separation of olefins, acetylenes, carbon monoxide or hydrogen sulfide from gaseous feedstreams. A solvent is made by dissolving CuAlCl.sub.4 in a liquid mixture of monochloro biphenyls. This solvent is used to contact the gas feedstream and dissolve by complexation the ligand part of the feedstream. The ligand-fat solvent is separated from the gas feedstream and the ligand recovered by running the solvent through an atmospheric reboiler and one or more reboilers under vacuum. The gas streams of the reboilers are combined and after cooling are a nearly pure stream of the separated ligand.Solutions of CuAlCl.sub.Type: GrantFiled: June 17, 1985Date of Patent: September 1, 1987Inventor: David G. Walker
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Patent number: 4605780Abstract: Process for removing alkyl substituted phosphine from a hydroformylation medium and enhancing the rhodium complex catalyst contained therein via an oxygenation treatment.Type: GrantFiled: September 24, 1980Date of Patent: August 12, 1986Assignee: Union Carbide CorporationInventors: Ernst Billig, David B. Stanton
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Patent number: 4599472Abstract: Hydrocarbon solutions containing iodine or iodine-containing impurities are rendered essentially color-free by distillation in the presence of small amounts of a hydrocarbon soluble organometallic compound.Type: GrantFiled: June 27, 1985Date of Patent: July 8, 1986Assignee: Phillips Petroleum CompanyInventor: Raymond L. Cobb
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Patent number: 4525180Abstract: With application of new liquid absorbent, comprised of a compound selected from a group composed of silver halide and cuprous halide, an aluminium halide, a polymer selected from a group composed of styrene and styrene derivatives, and an aromatic hydrocarbon, it is possible to recover ethylene by absorbing ethylene from gaseous mixture containing ethylene such as FCC off gas, ethylene plant off gas and coke oven gas. In particular, said liquid absorbent is neither diluted nor reduced its capability to absorb ethylene by water or its vapor contained in the said gaseous mixture, so the liquid absorbent can be used repeatedly for the recovery of ethylene from gaseous mixture containing ethylene and water or its vapor, without any pretreatment to reduce the water content of said gaseous mixture.Type: GrantFiled: March 15, 1984Date of Patent: June 25, 1985Assignee: Hidefumi HiraiInventors: Hidefumi Hirai, Makoto Komiyama, Susumu Hara
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Patent number: 4471152Abstract: A process for separating a gaseous alkene mixture into components thereof which comprises contacting the gaseous alkene mixture with a cuprous complex of the formula [Cu(facac)].sub.x L.sub.y where facac is a fluorinated acetylacetonate and L is a stabilizing agent in an organic solvent wherein L is displaced by alkene. Cuprous complexes containing alkene can then be separated provided that the separation factor between alkene complex to be separated and other alkene complexes is at least about 1.05.Type: GrantFiled: May 6, 1983Date of Patent: September 11, 1984Assignee: Exxon Research and Engineering Co.Inventors: Gerald Doyle, Roy L. Pruett, David W. Savage, W. S. W. Ho
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Patent number: 4458095Abstract: An improvement in a process for the pyrolytic conversion of rubber and plastic waste to hydrocarbon products which results in reduced levels of nitrogen and sulfur impurities in these products. The improvement comprises pyrolyzing the waste in the presence of at least about 1 weight percent of salts, based on the weight of the waste, preferably chloride or carbonate salts, of zinc or copper (I).This invention was made under contract with or subcontract thereunder of the Department of Energy Contract #DE-AC02-78-ER10049.Type: GrantFiled: September 30, 1982Date of Patent: July 3, 1984Assignee: Ford Motor CompanyInventors: Robert C. Wingfield, Jr., Jacob Braslaw, Roy L. Gealer
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Patent number: 4424121Abstract: A method is disclosed for reducing the nitrogen content of hydrocarbon liquids. The method comprises contacting the hydrocarbon liquid with a solid metal salt capable of selectively extracting nitrogen-containing compounds from the hydrocarbon liquid to thereby form a nitrogen-rich solid extract. Nitrogen-lean hydrocarbon liquid is then separated from the solid extract. The solid extract is washed with a solvent capable of selectively dissolving non-nitrogen-containing compounds entrained in the solid extract. The solid extract is then treated with a release agent for selectively dissolving nitrogen-containing compounds to thereby recover the metal salt. The presently preferred metal salt is cupric chloride.Type: GrantFiled: July 30, 1982Date of Patent: January 3, 1984Assignee: Occidental Research CorporationInventors: Henry W. Choi, Martin B. Dines
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Patent number: 4400564Abstract: A process and apparatus for separating monoolefins from diolefins comprising contacting a mixture of monoolefins and diolefins with a complexing agent selected from the group consisting of copper(I) salts of sulfonic acids and copper(I) salts of dialkylphosphates and a suitable hydrocarbon solvent for the complexing agent under such conditions that the monoolefins and diolefins form complexes with the complexing agent. The monoolefin complex can be separated from the diolefin complex based either on the relative solubilities of the two complexes in the hydrocarbon solvent for the complexing agent or based on the relative strengths of the two complexes.Type: GrantFiled: April 14, 1980Date of Patent: August 23, 1983Assignee: Phillips Petroleum CompanyInventors: Marvin M. Johnson, Donald C. Tabler
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Patent number: 4398052Abstract: A process and apparatus for separating monoolefins from other monoolefins comprising contacting a mixture of different monoolefins with a complexing agent selected from the group consisting of copper (I) salts of sulfonic acids and copper (I) salts of dialkyl phosphates and a suitable hydrocarbon solvent for the complexing agent under such conditions that the monoolefins form different strength complexes with the complexing agent. The different strength of the complexes provides a mechanism by which even closely boiling monoolefin isomers may be separated.Type: GrantFiled: April 14, 1980Date of Patent: August 9, 1983Assignee: Phillips Petroleum CompanyInventors: Donald C. Tabler, Marvin M. Johnson
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Patent number: 4387055Abstract: A cuprous oxalate complex of the formula Cu.sub.2 (CO).sub.n L.sub.m C.sub.2 O.sub.4 wherein L is an unsaturated hydrocarbon containing at least one non-aromatic unsaturation and n and m are numbers from 0 to 2.Type: GrantFiled: July 13, 1981Date of Patent: June 7, 1983Assignee: Exxon Research and Engineering Co.Inventor: Gerald Doyle
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Patent number: 4353840Abstract: In processes in which liquid sorbents that are solutions in an aromatic hydrocarbon or halogenated aromatic hydrocarbon of a bimetallic salt complex having the generic formula M.sub.I M.sub.II X.sub.n.Aromatic, wherein M.sub.I is a Group I-B metal, M.sub.II is a Group III-A metal, X is halogen, n is the sum of the valences of M.sub.I and M.sub.II, and Aromatic is a monocyclic aromatic hydrocarbon or halogenated aromatic hydrocarbon are used to separate complexible ligands from a gas feedstream that comprises an olefin having 2 or 3 carbon atoms, alkylation of the aromatic hydrocarbon or halogenated aromatic hydrocarbon is inhibited by incorporating in the liquid sorbent from 8.5 mole percent to 30 mole percent, based on the Group I-B metal in the liquid sorbent, of an amine-aluminum chloride adduct, such as ammonia-aluminum chloride adduct or pyridine-aluminum chloride adduct.Type: GrantFiled: March 6, 1981Date of Patent: October 12, 1982Assignee: Tenneco Chemicals, Inc.Inventors: Donald J. Haase, David G. Walker, Paul C. Ostrowski
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Patent number: 4317950Abstract: In processes in which liquid sorbents that are solutions in an aromatic hydrocarbon or halogenated aromatic hydrocarbon of a bimetallic salt complex having the generic formula M.sub.I M.sub.II X.sub.n.Aromatic, wherein M.sub.I is a Group I-B metal, M.sub.II is a Group III-A metal, X is halogen, n is the sum of the valences of M.sub.I and M.sub.II, and Aromatic is a monocyclic aromatic hydrocarbon or halogenated aromatic hydrocarbon are used to separate complexible ligands from a gas feedstream that comprises an olefin having 2 or 3 carbon atoms, alkylation of the aromatic hydrocarbon or halogenated aromatic hydrocarbon is inhibited by incorporating in the liquid sorbent from 8.5 mole percent to 30 mole percent, based on the Group I-B metal in the liquid sorbent, of an amine-aluminum chloride adduct, such as ammonia-aluminum chloride adduct or pyridine-aluminum chloride adduct.Type: GrantFiled: July 23, 1980Date of Patent: March 2, 1982Assignee: Tenneco Chemicals, Inc.Inventors: Donald J. Haase, David G. Walker, Paul C. Ostrowski
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Patent number: 4307262Abstract: In processes in which liquid sorbents that are solutions in an aromatic hydrocarbon or halogenated aromatic hydrocarbon of a bimetallic salt complex having the generic formula M.sub.I M.sub.II X.sub.n.Aromatic, wherein M.sub.I is Group I-B metal, M.sub.II is a Group III-A metal, X is halogen, n is the sum of the valences of M.sub.I and M.sub.II, and Aromatic is a monocyclic aromatic hydrocarbon or halogenated aromatic hydrocarbon are used to separate complexible ligands from a gas feedstream that comprises an olefin having 2 or 3 carbon atoms, alkylation of the aromatic hydrocarbon or halogenated aromatic hydrocarbon is inhibited by incorporating in the liquid sorbent a small amount of zinc diphenyl.Type: GrantFiled: May 28, 1980Date of Patent: December 22, 1981Assignee: Tenneco Chemicals, Inc.Inventor: Paul C. Ostrowski
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Patent number: 4304952Abstract: In processes in which liquid sorbents that are solutions in an aromatic hydrocarbon or halogenated aromatic hydrocarbon of a bimetallic salt complex having the generic formula M.sub.I M.sub.II X.sub.n.Aromatic, wherein M.sub.I is a Group I-B metal, M.sub.II is a Group III-A metal, X is halogen, n is the sum of the valences of M.sub.I and M.sub.II, and Aromatic is an aromatic hydrocarbon or halogenated aromatic hydrocarbon are used to separate complexible ligand from a gas feedstream that comprises an olefin having 2 or 3 carbon atoms, alkylation of the aromatic hydrocarbon or halogenated aromatic hydrocarbon is inhibited by incorporating in the liquid sorbent a small amount of triphenylboron.Type: GrantFiled: July 23, 1980Date of Patent: December 8, 1981Assignee: Tenneco Chemicals, Inc.Inventor: Paul C. Ostrowski
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Patent number: 4203927Abstract: Olefins are oxidized to carbonyl compounds, for example, 2-hexene to a mixture of 2-hexanone and 3-hexanone, with a palladium/copper/boric acid catalyst and a suitable surfactant or phase transfer agent. The reaction takes place in a diluent system comprising at least two liquid phases, wherein at least one liquid phase is an aqueous phase, and in the presence of free oxygen. The catalyst system can be used to oxidize internal olefins, as well as terminal olefins, at reasonable rates. The catalyst system can also be used for the selective oxidation of linear olefins in a mixed stream containing linear and branched olefins.Type: GrantFiled: April 11, 1978Date of Patent: May 20, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4185039Abstract: Process for the selective catalytic oxidation of carbon monoxide in the presence of olefin monomers without appreciable oxidation of such monomers. According to this process, a gaseous waste stream containing carbon monoxide, olefin monomers, and a variety of other agents, is contacted with a catalytically effective amount of copper chromite, preferably in an oxygen enriched environment, at temperatures in the range from about 200.degree. C. to about 325.degree. C. The contact time of the stream with the catalyst bed can vary within broad limits, and the duration of which will vary inversely with the temperature of the catalyst bed.Type: GrantFiled: December 26, 1978Date of Patent: January 22, 1980Assignee: B. F. Goodrich CompanyInventor: Jamal S. Eden
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Patent number: 4174355Abstract: Conjugated diolefins contaminated with relatively high levels of acetylenic impurities in a hydrocarbon feedstream are purified by a cyclic, vapor phase, predominantly catalytic cracking process which selectively removes alpha-cetylenes in a single pass. A feedstream containing about equal weights of isoprene and mixed monoolefins and alkanes contaminated with alpha-acetylenes including isopropenyl acetylene inter alia, up to about 5.0 percent by weight (% by wt) of the feedstream, and a larger amount of cyclopentadiene, is contacted in the vapor phase with a supported Group I B metal oxide catalyst in the absence of hydrogen, at a temperature in the range from about 300.degree. F. to about 360.degree. F. In this narrow temperature range, the loss of diolefin is less than 1% by weight. Essentially all the cyclopentadiene (CPD) is left unconverted.Type: GrantFiled: June 19, 1978Date of Patent: November 13, 1979Assignee: The B. F. Goodrich CompanyInventors: Pradeep V. Patel, Donald E. Murphy