Abstract: There are provided an ionic liquid having ether group(s) in which a copper(I) compound is included, a method for preparing the same, and a method for removing traces amounts of acetylene-based hydrocarbon compounds included in olefin by absorption or extraction using the same. When the disclosed solution is used, oxidation of Cu(I) to Cu(II) is prevented since CuX is stabilized by the ionic liquid. Thus, selective removal efficiency of acetylenic compounds is improved greatly while the removal performance is retained for a long period of time. Further, since the solution according to the present disclosure is applicable as an extractant as well as an absorbent, the associated operation is simple and apparatus cost can be decreased.

Abstract: A process for desulphurising hydrocarbons includes the steps of (i) passing a mixture of hydrocarbon and hydrogen over a hydrodesulphurisation catalyst to convert organosulphur compounds present in the hydrocarbon to hydrogen sulphide, (ii) passing the resulting mixture over a hydrogen sulphide sorbent including zinc oxide to reduce the hydrogen sulphide content of the mixture and (iii) passing the hydrogen sulphide-depleted mixture over a further desulphurisation material, where the further desulphurisation material includes one or more nickel compounds, a zinc oxide support material, and optionally one or more promoter metal compounds selected from one or more compounds of iron, cobalt, copper and precious metals, the desulphurisation material having a nickel content in the range 0.3 to 20% by weight and a promoter metal content in the range 0 to 10% by weight.

Abstract: The present invention relates to a method of purifying olefin, the method comprising removing a small amount of acetylenic compounds contained in olefin by using pyrrolidinium-based or piperidinium-based ionic liquid mixtures comprising copper (I) halide. According to the method of the present invention, copper (I) halide is stabilized by pyrrolidinium-based or piperidinium-based ionic liquids, suppressing the oxidation of Cu(I) into Cu(II), whereby the capacity of removing acetylenic compounds can be maintained for a long time and the selective removal rate of acetylenic compounds to olefin can be significantly improved. In addition, since the ionic liquid mixtures comprising copper (I) halide used in the method of the present invention can be applied to both absorption and extraction processes, it can effectively remove acetylenic compounds from olefin in a more simple and economical way compared to the existing adsorption and membrane separation processes.

Abstract: The present invention is directed to compositions and methods for the recovery of olefins from a mixture. The compositions of the present invention comprise: (1) a transition metal ion; (2) a counter anion; (3) a ligand selected from the group consisting of a bidentate ligand and a tridentate ligand, wherein the ligand comprises at least two nitrogen atoms, and wherein each of the nitrogen atoms comprises a lone pair of electrons; and (4) a polar solvent with a boiling point of at least about 200° C. The methods of the present invention comprise: (1) providing the aforementioned compositions; (2) bonding at least a portion of the olefins in a mixture to the transition metal ion in the composition to form a complex; (3) separating the complex from the mixture; and (4) recovering the olefins from the complex.

Abstract: 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.

Abstract: 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.

Abstract: Process for the removal of oxygen from a gas mixture comprising oxygen, at least one olefin, hydrogen, carbon monoxide and optionally at least one alkyne, the ratio of oxygen:hydrogen in the gas mixture being 1 part by volume of oxygen to at least 5 parts by volume of hydrogen. The process comprises contacting the gas mixture with a catalyst in a reaction zone under conditions sufficient to oxidise at least a portion of the hydrogen and to oxidize at least a portion of the carbon monoxide and without significant hydrogenation of the at least one olefin. The catalyst comprises at least one metal or oxide of a metal from the 10th group of the Periodic Table of Elements, the metal or oxide of the metal being supported on an oxide support, provided that the catalyst also comprises tin.

Abstract: Catalysts for the purification of ethylene containing copper and zinc, optionally one or more promoters or supports. These catalysts are produced by precipitation, drying, calcination and compression, optionally with the addition of additives, the compressed catalyst particles are calcinated at a temperature between from 300 to 700° C.

Abstract: 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.

Abstract: Methods for separating di-olefins from mono-olefins, and olefins from non-olefins such as paraffins, oxygenates and aromatics; are provided. The methods use metal salts which complex both mono-olefins and di-olefins, but which selectively complex di-olefins in the presence of mono-olefins. The metal salts are dissolved or suspended in ionic liquids, which tend to have virtually no vapor pressure. Preferred salts are Group IB salts, more preferably silver and copper salts. A preferred silver salt is silver tetrafluoroborate. A preferred copper salt is silver CuOTf. Preferred ionic liquids are those which form stable solutions, suspensions or dispersions of the metal salts, which do not dissolve unwanted non-olefins, and which do not isomerize the mono- or di-olefins. The equivalents of the metal salt can be adjusted so that di-olefins are selectively adsorbed from mixtures of mono- and di-olefins. Alternatively, both mono- and di-olefins can be adsorbed, and the mono-olefins selectively desorbed.

Abstract: The present invention relates to the separation of diolefins, and lower aromatics from mixed streams of hydrocarbons using ionic liquids and metal complexes. The present invention provides a novel method to separate diolefins and lower aromatics from other hydrocarbyl streams which may contain small amounts of water.

Abstract: Methods for separating di-olefins from mono-olefins, and olefins from non-olefins such as paraffins, oxygenates and aromatics; are provided. The methods use metal salts which complex both mono-olefins and di-olefins, but which selectively complex di-olefins in the presence of mono-olefins. The metal salts are dissolved or suspended in ionic liquids, which tend to have virtually no vapor pressure. Preferred salts are Group IB salts, more preferably silver and copper salts. A preferred silver salt is silver tetrafluoroborate. A preferred copper salt is silver CuOTf. Preferred ionic liquids are those which form stable solutions, suspensions or dispersions of the metal salts, which do not dissolve unwanted non-olefins, and which do not isomerize the mono- or di-olefins. The equivalents of the metal salt can be adjusted so that di-olefins are selectively adsorbed from mixtures of mono- and di-olefins. Alternatively, both mono- and di-olefins can be adsorbed, and the mono-olefins selectively desorbed.

Abstract: 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.

Abstract: 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.

Abstract: The present invention provides an improved method for deep selective hydrogenation for use in recovering high purity olefins from cracked gas effluents or other paraffin/olefin gaseous mixtures by use of a chemical absorption process.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: A process for the recovery of mercury and arsenic for which elementary mercury and/or mercury mercaptides are recovered prior to the recovery of arsenic and wherein the recovery temperature of the arsenic is higher than the recovery temperature of the mercury.

Abstract: For removing mercury and any arsenic in hydrocarbon charges containing mercury and sulfur, the charge is contacted with an arsenic collecting material having catalytic properties ("catalyst") in hydrogen, the material containing at least one metal selected from the group consisting of nickel, cobalt, iron, palladium, and platinum; at least one metal selected from the group consisting of chromium, molybdenum, tungsten, and uranium; and an active phase carrier. Downstream of the catalyst or mixed therewith is a mercury collecting material containing a sulfide of at least one metal selected from the group consisting of copper, iron, and silver or sulfur, and an active phase carrier.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: Organic sulfides are separated from olefins (in particular monoolefins) by absorption with Cu(I) salt(s) of a hydrocarbonsulfonic acid, preferably a solution of Cu(I) dodecylbenzene sulfonate(s).

Abstract: A process for absorbing olefinically-unsaturated hydrocarbon compounds from feedstreams containing such compounds by contacting said feed streams with metal-diketone absorbents of the formula: ##STR1## wherein R.sub.1 is trichloroemthyl or R.sub.F ; R.sub.F is C.sub.n F.sub.2n+1 and n is 1-8; R.sub.2 is H or hydrocarbyl of 2-20 carbon atoms having at least one olefinic unsaturated bond; M.sup.I is Cu.sup.I or Ag.sup.I and R.sub.3 is hydrocarbyl of 2-20 carbon atoms having at least one olefinic unsaturated bond.

Abstract: Process for elimination of mercury in hydrocarbon charges wherein said charge is contacted, under hydrogen, with a catalyst containing at least one metal from the group consisting of nickel, cobalt, iron and palladium followed by--or mixed with--a capture mass containing sulfur or a metal sulfide.

Abstract: Arsines are removed from streams of hydrocarbons or inert gases by contacting the streams with copper (II) chromite catalyst.

Abstract: 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.

Abstract: Arsines are removed from gaseous stream, e.g., hydrocarbon or inert gas streams, comprising arsine impurities and also hydrogen sulfide, by contacting these gas streams with a sorbent material comprising copper oxide and zinc oxide. Preferably, the sorbent material is prepared by coprecipitating of hydroxides of copper and zinc and subsequent heating the hydroxides so as to convert the hydroxides to CuO and ZnO. Optionally, aluminum oxide is also present in the sorbent material.

Abstract: An aromatic solution of the compound CuAl(CN)Cl.sub.3 alone or with additional solid CuAl(CN)Cl.sub.3 is used for the separation of some unsaturated compound (olefin, acetylene or carbon monoxide) from a feedstream.The feedstream is contacted with the solvent to form a complex of the ligand (olefin, acetylene or carbon monoxide). The feedstream is then separated from the solvent. The solvent is then treated with some combination of heat and lowered pressure to separate the ligand from the solvent. The ligand poor solvent is then recycled to contact fresh feedstream.

Abstract: An improved catalyst for removal of acetylenes from liquid hydrocarbon streams with a minimum loss of diolefinic unsaturation present in said liquid composition is disclosed. The catalytic materials, basically copper metal impregnated on a gamma alumina support prepared from an organo aluminum compound. The support has properties not found in alumina prepared from naturally occurring precursors.

Abstract: 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.

Abstract: 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.

Abstract: An improved catalyst for removal of acetylenes from liquid hydrocarbon streams with a minimum loss of diolefinic unsaturation present in said liquid composition is disclosed. The catalytic materials, basically copper metal associated with one or more activator metals are impregnated on a gamma alumina support prepared from an organo aluminum compound. The support has properties not found in alumina prepared from naturally occurring precursors.

Abstract: Alkenes, alkynes or mixtures thereof are removed from feedstreams by a process which comprises contacting the feedstream with a solution of a cuprous fluorinated acetylacetone in an organic solvent containing stabilizing agent to remove alkene, alkyne or mixture thereof by forming a first cuprous complex, decomposing the first cuprous complex whereby stabilizing agent replaces alkene or alkyne in the first cuprous complex to form a second cuprous complex, and separating the displaced component. The formation of the second cuprous complex avoids any deposition of copper metal upon heating.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: A process of removing unsaturated hydrocarbons containing at least one non-aromatic unsaturation from feedstreams which comprises contacting the feedstream with at least one of Cu.sub.2 O or Ag.sub.2 O and a fluorinated acetylacetonate of the formula ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 fluoroalkyl, C.sub.1 -C.sub.8 alkyl, C.sub.4 -C.sub.6 heterocycle containing O, S or N or C.sub.6 -C.sub.10 aryl, R.sup.2 is H or C.sub.1 -C.sub.6 alkyl with the proviso that R.sup.1 and R.sup.2 together with the carbons to which they are attached may be joined together to form a C.sub.6 ring and n is from 1 to 8, in an inert organic solvent.

Abstract: Conjugated diolefins contaminated with relatively high levels of acetylenic impurities in a hydrocarbon feedstream are purified by a cyclic, liquid phase, predominantly catalytic cracking process which selectively removes alpha-acetylenes in a single pass. The energy requirement for removing the alpha-acetylenes in this liquid phase process are from about one-third to about one-fifth as great as that required in a comparable vapor phase process. A feedstream containing about equal weights of butadiene and mixed monoolefins and alkanes contaminated with alpha-acetylenes including vinyl acetylene and methyl acetylene, inter alia, in an amount up to about 1.0 percent by weight (% by wt) of the feedstream, is contacted in the liquid phase with a supported Group I B metal oxide catalyst in the absence of hydrogen, at a temperature in the range from about 200.degree. F. to about 260.degree. F.

Abstract: 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.