Unsaturated Sorbate Patents (Class 585/829)
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Patent number: 6080905Abstract: Processes using heterogeneous adsorbents are disclosed for purification of olefins such as are typically produced by thermal cracking of suitable hydrocarbon feedstocks, by passing a stream of olefin having from 2 to about 8 carbon atoms, containing acetylenic impurities having the same or similar carbon content, and optionally saturated hydrocarbon gases, through a particulate bed of predominantly a support material having high surface area on which is dispersed at least one metallic element. Adsorption is carried out in an essentially dihydrogen-free atmosphere within the bed, selective and reversible adsorption and/or complexing of the contained acetylenic contaminants with the adsorbent, and thereby obtain purified effluent which contains less than a predetermined level of the acetylenic impurities.Type: GrantFiled: February 12, 1998Date of Patent: June 27, 2000Assignee: BP Amoco CorporationInventors: Mark P. Kaminsky, Shiyou Pei, Richard A. Wilsak, Robert C. Whittaker
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Patent number: 6069289Abstract: A process to separate multimethyl-branched alkanes from a mixture of multimethyl-branched alkanes, monomethyl-branched alkanes, and normal alkanes has been developed. The mixture is introduced to a simulated moving bed of solid adsorbent particles having the selectivity normal alkanes>monomethyl-branched alkanes>multimethyl-branched alkanes. The adsorbent may be silicalite, ferrierite, zeolite Beta, MAPO-31, SAPO-31, SAPO-11, zeolite X ion exchanged with alkaline cations, alkaline earth cations, or a mixture thereof, and zeolite Y ion exchanged with alkaline cations, alkaline earth cations, or a mixture thereof. A raffinate stream enriched in multimethyl-branched alkanes is removed from the simulated moving bed.Type: GrantFiled: August 31, 1998Date of Patent: May 30, 2000Assignee: UOP LLCInventors: Hemant W. Dandekar, Gregory A. Funk, Herman A. Zinnen
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Patent number: 6060032Abstract: A process is set forth for the production of a carbon monoxide stream from a feed stream comprising carbon monoxide, hydrogen, carbon dioxide, methane, nitrogen and moisture. The process comprises contacting the feed stream at elevated pressure with a layered adsorbent bed comprising (i) a pretreatment adsorbent in order to adsorb moisture preferentially over methane, nitrogen and carbon dioxide and (ii) a main adsorbent in order to adsorb carbon monoxide preferentially over hydrogen, carbon dioxide, methane and nitrogen. A key to the present invention is that a carbon-based adsorbent is used as the pretreatment adsorbent.Type: GrantFiled: July 27, 1998Date of Patent: May 9, 2000Assignee: Air Products and Chemicals, Inc.Inventors: Christopher Thomas Hable, Timothy Christopher Golden, Wilbur Clymer Kratz
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Patent number: 5912395Abstract: The capacity of a simulated moving bed adsorptive separation process is increased by flushing the contents of the transfer line just previously used to remove the raffinate stream from the adsorbent chamber back into the adsorbent chamber. This step is performed immediately upstream of the point of raffinate withdrawal. Preferably the feed stream to the process is used as the flushing liquid. This flush step eliminates the passage of a quantity of the raffinate material into the adsorbent chamber when the process conduit is subsequently used to charge the feed stream to the adsorbent chamber.Type: GrantFiled: February 9, 1998Date of Patent: June 15, 1999Assignee: UOP LLCInventor: Robert J.L. Noe
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Patent number: 5863315Abstract: Four adsorbers 1 to 4, each operating in a cycle comprising (described for adsorber 2): an adsorption step 1 wherein a feed from adsorber 2 is circulated to adsorber 2; an adsorption step 2 wherein feed is injected to the bottom of adsorber 2 and a product rich in isoparaffins is recovered from the head of adsorber 2; an adsorption step 3 wherein a portion of the fluid leaving adsorber 2 is sent to adsorber 3; an adsorption step 4 wherein the head of adsorber 2 receiving the feed is connected to the bottom of adsorber 3; a first depressurisation step 5 wherein adsorber 2 at high pressure is connected to adsorber 4 at a lower pressure; a second depressurisation step 6 wherein the head of adsorber 2 is closed; a stripping step 7 wherein the bottom of adsorber 2, which receives desorbent overhead, is connected to the top of adsorber 2; two principal stripping steps 8 and 9 wherein adsorber 2 alone is supplied with desorbent; a stripping finishing step 10 wherein adsorber 2 is continued to be supplied with desorbType: GrantFiled: July 25, 1997Date of Patent: January 26, 1999Assignee: Institut Francais du PetroleInventors: Sophie Jullian, Jean-Louis Ambrosino, Alain Chansolme, Valerie Wiss-Henrard
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Patent number: 5744687Abstract: A hydrocarbon stream is cracked to produce a hot gaseous stream which is compressed and cooled to condense almost all of the hydrocarbons contained in the stream. A noncondensed stream remaining after the condensation step, comprised predominantly of hydrogen and C.sub.1 to C.sub.3 hydrocarbons, is subjected to pressure swing adsorption or temperature swing adsorption at an adsorption temperature of about 0.degree. to about 250.degree. C. in a bed of adsorbent which selectively adsorbs ethylene and propylene, thereby adsorbing substantially all of the ethylene and propylene from the gas stream. The ethylene and/or propylene is recovered upon bed regeneration.Type: GrantFiled: April 22, 1994Date of Patent: April 28, 1998Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc H. Dao
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Patent number: 5488185Abstract: An ethene stream which contains ethane as an impurity or a propene stream which contains propane as an impurity is hydrated with water vapor in the presence of a hydration catalyst to produce ethanol or isopropanol, respectively. After removal of the alcohol the gaseous product stream is subjected to adsorption, thereby producing an ethene-enriched stream or a propene-enriched stream. The ethene-enriched stream or the propene-enriched stream is recycled to the hydration reactor.Type: GrantFiled: April 22, 1994Date of Patent: January 30, 1996Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc H. Dao
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Patent number: 5442040Abstract: The present invention is directed to adsorbing polymeric hydrocarbons (ie. polymers of iso-butylene, polymers of the isomers of iso-butylene (poly-butenes) and co-polymers of iso-butylene and other olefins (butyl rubber) from hydrocarbon or raffinate streams using activated carbon as the adsorbent. One embodiment includes the selective removal of poly-isobutylene (PIB) from a hydrocarbon stream by activated carbon. The stream which can exceed 100 ppm PIB is contacted with the activated carbon for a sufficient time to reduce the PIB content of the hydrocarbon stream to less than about 1 ppm.Type: GrantFiled: January 10, 1994Date of Patent: August 15, 1995Assignee: Exxon Chemical Patents Inc.Inventor: John D.-Y. Ou
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Patent number: 5365011Abstract: Method of separating a gaseous alkene from a gaseous alkane by a pressure swing adsorption process unit alone or in combination with the distillation column wherein the alkene is preferentially adsorbed onto a bed of 4A zeolite at a temperature of about 50.degree. to about 200.degree. C.Type: GrantFiled: May 5, 1993Date of Patent: November 15, 1994Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc H. Dao
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Patent number: 5322927Abstract: Polyolefins are produced by a process which includes the steps of: polymerizing an olefin in a reaction zone; removing unreacted olefin from the polymer in a flash chamber and recycling the unreacted olefin to the reaction zone; stripping unreacted olefin from the polymer by passing a stripping gas through the polymer in a stripping zone; passing the unreacted olefin from the stripping zone at superatmospheric pressure through an adsorbent which selectively adsorbs olefins; depressurizing the adsorbent to produce a substantially pure olefin and recycling the substantially pure olefin to the reaction zone; purging the adsorbent bed with a nonadsorbable gas to remove residual unreacted olefin from the adsorbent; and passing the purge gas-unreacted olefin to the stripping zone to be used as stripping gas.Type: GrantFiled: September 2, 1992Date of Patent: June 21, 1994Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Virginia Malik
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Patent number: 5276246Abstract: A chromatographic process for separating normal olefins from mixtures with branched-chain olefins with a high silica zeolitic molecular sieve, e.g., silicalites, ZSM-5, etc., having low acid catalytic reactivity, which selectively adsorbs the normal olefins, and uses alkyl-substituted cycloparaffins, e.g., methylcyclohexane, as desorbents.Type: GrantFiled: December 23, 1991Date of Patent: January 4, 1994Assignee: UOPInventors: Beth McCulloch, James R. Lansbarkis
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Patent number: 5258571Abstract: The present invention is directed to a process for adsorptive separation of carbon monoxide or olefins from gas mixtures using adsorbents, which comprise cuprous compounds dispersed on amorphous oxide or carbon macroporous supports. The compositions are prepared by impregnating cupric compounds on, preferably pretreated, supports with the aid of an aqueous solution of an ammonium salt of a di- or polycarboxylic acid dispersant, such as ammonium citrate, followed by reduction of the cupric compound to the corresponding cuprous compound. The reduction can be performed either by the use of elevated temperature or by the use of a reducing gas preferably carbon monoxide at relatively low temperatures up to 150.degree. C. Methods of synthesis are also disclosed.Type: GrantFiled: September 14, 1992Date of Patent: November 2, 1993Assignee: Air Products and Chemicals, Inc.Inventors: Timothy C. Golden, Wilbur C. Kratz, Frederick C. Wilhelm, Ronald Pierantozzi, Andrzej Rokicki
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Patent number: 5245099Abstract: A process is provided for the concentration and recovery of ethylene and heavier components from a hydrocarbon feedstream. A pressure swing adsorption (PSA) process is used to remove from hydrocarbon feedstream light cut comprising hydrogen, carbon monoxide, and methane and subsequently concentrate a heavy cut comprising the ethylene and heavy components in the PSA tail gas. In one aspect of the invention, an FCC off gas is separated into a light cut and a heavy cut and the heavy cut is routed to an ethylene plant. In another aspect of the invention, a C.sub.2 -rich stream is withdrawn from an ethylene plant and used to enhance the recovery of the ethylene and heavier stream in the PSA process and an ethylene-rich stream is returned to the ethylene plant.Type: GrantFiled: July 22, 1992Date of Patent: September 14, 1993Assignee: UOPInventor: Michael J. Mitariten
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Patent number: 5227567Abstract: A process for the separation and recovery of the product stream resulting from the dehydrogenation of dehydrogenatable hydrocarbons which process utilizes a chiller system for the recovery of olefin product liquid and a pressure swing adsorption unit to concentrate the olefin product liquid which is not recovered by the chiller.Type: GrantFiled: January 27, 1992Date of Patent: July 13, 1993Assignee: UOPInventors: Michael J. Mitariten, Norman H. Scott
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Patent number: 5220102Abstract: A chromatographic process for separating linear olefins from mixtures with branched-chain olefins with a high silica zeolitic molecular sieve, e.g., silicalites, ZSM-5, etc., having low acid catalytic reactivity, which selectively adsorbs the normal olefins, and uses ketones as desorbents.Type: GrantFiled: June 9, 1992Date of Patent: June 15, 1993Assignee: UOPInventors: Gregory A. Funk, James R. Lansbarkis, Anil R. Oroskar, Beth McCulloch
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Patent number: 5220099Abstract: A process for purifying linear paraffins in which a hydrocarbon stream containing linear paraffins contaminated with aromatics, sulfur-, nitrogen-, and oxygen-containing compounds, and color bodies, but essentially free of olefins, is contacted with a zeolitic solid adsorbent such as a NaX zeolite or zeolite MgY. After adsorption the zeolitic solid adsorbent is desorbed with an alkyl-substituted aromatic desorbent such as toluene.Type: GrantFiled: August 31, 1988Date of Patent: June 15, 1993Assignee: Exxon Chemical Patents Inc.Inventors: James L. Schreiner, Robert A. Britton, Charles T. Dickson, Frederick A. Pehler, Jr.
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Patent number: 5132485Abstract: A process using zeolites, or molecular sieves, for separating an alpha-olefin having five or more carbons and the corresponding internal olefin or olefins. A mixture containing the alpha-olefin and one or more of the corresponding internal olefins is contacted with a zeolite which had previously undergone cation exchange. The selectivity of the zeolite, or molecular sieve, changes and eventually reverses as the carbon number increases. The selectivity is also related to the identity of the cation introduced during the cation exchange.Type: GrantFiled: November 21, 1990Date of Patent: July 21, 1992Assignee: Exxon Chemical Patents Inc.Inventor: Di-Yi Ou
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Patent number: 4864071Abstract: A solid adsorbent for an unsaturated hydrocarbon comprising (a) (i) a silver or copper(I) halide or (ii) a silver or copper(I) halide and the halide of a bivalent metal, or (iii) a silver or copper(I) halide and an aluminum halide, and (b) polystyrene or a derivative thereof.This solid adsorbent can effectively adsorb an unsaturated hydrocarbon such as ethylene from a gas mixture by contacting the gas mixture therewith at a temperature of -40.degree. C. to 140.degree. C. under normal pressures.Type: GrantFiled: September 4, 1987Date of Patent: September 5, 1989Assignee: Hidefumi HiraiInventors: Hidefumi Hirai, Makoto Komiyama, Susumu Hara
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Patent number: 4747855Abstract: A solid adsorbent for an unsaturated hydrocarbon including (a) (i) a copper(I) halide or oxide or (ii) a halide, carboxylate, sulfate, basic salt, oxide, or amine complex salt of copper(II) and (b) activated carbon or graphite is described.This solid adsorbent can effectively adsorb an unsaturated hydrocarbon such as ethylene from a gas mixture by being placed in contact with the gas mixture at a temperature of -40.degree. C. to 90.degree. C. under normal pressure.Type: GrantFiled: January 21, 1987Date of Patent: May 31, 1988Assignee: Hidefumi HiraiInventors: Hidefumi Hirai, Makoto Komiyama, Keiichiro Wada
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Patent number: 4727122Abstract: There is disclosed a process for recovering olefin monomers, e.g., C.sub.3 -C.sub.10 alpha-olefins, from a vent gas of a vapor phase process for polymerizing olefins. The method comprises passing the vent gas, obtained by purging a resin produced in the polymerization process with an inert gas, such as nitrogen, into contact with an adsorbent to effect the adsorption of an olefin monomer. Subsequently, the adsorbed monomer is removed by contacting the adsorbent with a second monomer having lower molecular weight than the adsorbed monomer.Type: GrantFiled: September 4, 1986Date of Patent: February 23, 1988Assignee: Mobil Oil CorporationInventors: Carol S. Lee, John L. Pickering, Jr.
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Patent number: 4675309Abstract: There is disclosed an adsorbent comprising a macroreticular polystyrene type resin having amino groups selected from the group consisting of primary, secondary and tertiary amino groups and combinations thereof, and a copper(I) halide fixed to the macroreticular polystyrene type resin. Such an adsorbent has been found to be advantageously employed for the selective adsorption-separation of a gas from a gaseous mixture.Type: GrantFiled: April 21, 1986Date of Patent: June 23, 1987Assignee: Hidefumi HiraiInventors: Hidefumi Hirai, Makoto Komiyama, Kazunori Kurima, Keiichiro Wada
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Patent number: 4650917Abstract: The viscosity index of synthetic lubricant stocks such as those produced by olefin oligomerization is increased by contacting such stocks with a solid acidic isomerization catalyst such as boron trifluoride at elevated temperatures, say above about 200.degree. C. The high viscosity index fractions of the resulting product may be sorbed by a shape-selective zeolite such as ZSM-5 and recovered to produce a high VI lubricant.Type: GrantFiled: August 19, 1985Date of Patent: March 17, 1987Assignee: Mobil Oil CorporationInventors: Ralph M. Dessau, David H. Olson
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Patent number: 4645576Abstract: This invention provides a process for isolating and recovering butene-1 of high purity at high yield. Firstly, a butane-butene fraction containing 0.1 to 7 wt % of isobutylene, 10 to 50 wt % of butene-1 and 5 to 20 wt % of isobutane is rectified to reduce the content of isobutane to not more than 0.1 wt %. Then, the rectified butane-butene fraction is passed through a reactor packed with an extrusion molded silica-alumina catalyst to polymerize isobutylene at a reaction velocity as high as 50 times or more of that of butene-1, thus forming oligomers of isobutylene. Finally, the hydrocarbon mixture from the reactor is rectified to remove the oligomers of isobutylene and the other C.sub.4 -hydrocarbons.Type: GrantFiled: May 10, 1984Date of Patent: February 24, 1987Assignee: Nippon Oil Co., Ltd.Inventors: Tetsuya Takezono, Takaaki Amari, Hirosuke Imai
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Patent number: 4570029Abstract: A process for separating isoprene from isobutylene, isopentane, and pentene-1. The process uses an adsorbent comprising activated carbon or molecular sieve carbon to selectively adsorb isoprene from the other hydrocarbons. High purity isoprene is recovered by desorption using desorbent materials which include olefinic hydrocarbons. The process is particularly suited for a simulated moving bed apparatus.Type: GrantFiled: March 4, 1985Date of Patent: February 11, 1986Assignee: UOP Inc.Inventors: Santi Kulprathipanja, Chin-Hsiung Chang
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Patent number: 4567309Abstract: A process for separating 1,3-butadiene from a feed mixture comprising 1,3-butadiene and at least one other C.sub.4 hydrocarbon. The process comprises contacting the feed, in liquid phase at adsorption conditions, with an adsorbent comprising activated or molecular sieve carbon which selectively adsorbs the 1,3-butadiene. The feed is then removed from the adsorbent and the 1,3-butadiene recovered by desorption at desorption conditions with a desorbent material comprising a hydrocarbon. The feed mixture and desorbent material have boiling points of at least 5.degree. C. difference.Type: GrantFiled: May 29, 1984Date of Patent: January 28, 1986Assignee: UOP Inc.Inventor: Santi Kulprathipanja
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Patent number: 4554390Abstract: A method for harvesting algae of the genus Dunaliella from suspensions thereof in brines containing sodium chloride at a concentration of about 3M or above, wherein the algal suspension is contacted with an adsorbent having a hydrophobic surface so as to adsorb the algae thereon, and the adsorbent with the algae adsorbed thereon is separated from the brine..beta.-carotene and other useful cell components may be extracted from the adsorbed algae by treatment with a suitable solvent.Type: GrantFiled: June 7, 1983Date of Patent: November 19, 1985Assignees: Commonwealth Scientific and Industrial Research Organization, Betatene LimitedInventors: Cyril C. Curtain, Harvey Snook
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Patent number: 4546094Abstract: A solid adsorbent for an unsaturated hydrocarbon comprising (a) (i) a silver or copper(I) halide or (ii) a silver or copper(I) halide and the halide of a bivalent metal, or (iii) a silver or copper(I) halide and an aluminum halide, and (b) polystyrene or a derivative thereof.This solid adsorbent can effectively adsorb an unsaturated hydrocarbon such as ethylene from a gas mixture by contacting the gas mixture therewith at a temperature of -40.degree. C. to 140.degree. C. under normal pressures.Type: GrantFiled: March 8, 1984Date of Patent: October 8, 1985Assignee: Hidefumi HiraiInventors: Hidefumi Hirai, Makoto Komiyama, Susumu Hara
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Patent number: 4486618Abstract: A process for separating a normal C.sub.6 olefin hydrocarbon from a mixture of the same with a C.sub.6 olefin branched chain and/or cyclic hydrocarbon. The process comprises contacting the mixture at separation conditions with a molecular sieve comprising a crystalline silica. The normal C.sub.6 olefin hydrocarbon is selectively retained and will be recovered from the molecular sieve by displacement with a displacement material comprising pentene-1 or butene-1. The process preferably employs a simulated moving bed.Type: GrantFiled: August 12, 1983Date of Patent: December 4, 1984Assignee: UOP Inc.Inventors: Santi Kulprathipanja, Richard W. Neuzil
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Patent number: 4469913Abstract: An improved technique for sorption of certain members of a ZSM-5 type of zeolites is provided. The class of zeolites is characterized by a silica to alumina mole ratio greater than 12 and a Constraint Index within the approximate range of greater than about 2 to about 12. The process of this invention involves sorption and/or selective separation of bicyclic fused-ring aromatic compounds, having a critical dimension less than 6.8 Angstrom units.Type: GrantFiled: June 6, 1983Date of Patent: September 4, 1984Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 4455445Abstract: A process for the separation of normal C.sub.4 hydrocarbons from isobutylene. A mixture of the normal C.sub.4 hydrocarbons and isobutylene is contacted with a molecular sieve comprising silicalite which is selective for the normal C.sub.4 hydrocarbons. The isobutylene is then recovered in the raffinate stream and the normal C.sub.4 hydrocarbons recovered by displacement with pentene-1.Type: GrantFiled: December 20, 1982Date of Patent: June 19, 1984Assignee: UOP Inc.Inventors: Richard W. Neuzil, Santi Kulprathipanja
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Patent number: 4444986Abstract: An improved hydrocarbon separation process by the selective sorption properties of certain members of a novel class of zeolites is provided. The novel class of zeolites is characterized by a silica to alumina mole ratio greater than 12 and a Constraint Index within the approximate range of greater than about 2 to about 12. The process of this invention involves selective separation of higher molecular weight hydrocarbon compounds in admixture with lower molecular weight hydrocarbon compounds within a homolgous series by contacting the respective mixture with a zeolite having a SiO.sub.2 /Al.sub.2 O.sub.3 mole ratio of at least about 12 and a Constraint Index with the approximate range of greater than 2 to about 12, to effect the selective sorption of said higher molecular weight hydrocarbon compounds by said zeolite.Type: GrantFiled: September 30, 1981Date of Patent: April 24, 1984Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 4438289Abstract: A process for reducing the level of cyclopentadiene present in a hydrocarbon stream containing isoprene and cyclopentadiene which involves contacting the stream with a base wherein said base is selected from the group consisting of potassium hydroxide, sodium hydroxide and potassium fluoride. The base is situated on activated carbon carrier.Type: GrantFiled: July 1, 1983Date of Patent: March 20, 1984Assignee: The Goodyear Tire & Rubber CompanyInventor: Richard M. D'Sidocky
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Patent number: 4433195Abstract: A process for the separation of a trans-olefin from a cis-olefin. A mixture of the trans- and cis-olefins is contacted with an adsorbent comprising silicalite which is selective for the trans-olefin. The process is particularly suitable for the separation of trans-2-butene from cis-2-butene.Type: GrantFiled: March 2, 1983Date of Patent: February 21, 1984Assignee: UOP Inc.Inventor: Santi Kulprathipanja
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Patent number: 4423280Abstract: An improved hydrocarbon separation process by the selective sorption properties of certain members of a novel class of zeolites is provided. The novel class of zeolites is characterized by a silica to alumina mole ratio greater than 12 and a Constraint Index within the approximate range of greater than about 2 to about 12. The process of this invention involves selective separation of non-aromatic compounds in admixture with aromatic compounds by contacting the mixture with zeolite ZSM-5, ZSM-11, ZSM-23 or ZSM-35, said zeolite having a SiO.sub.2 /Al.sub.2 O.sub.3 mole ratio of at least about 12, to effect the selective sorption of said non-aromatic compounds by said zeolite.Type: GrantFiled: September 30, 1981Date of Patent: December 27, 1983Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 4392004Abstract: A process for reducing the level of cyclopentadiene present in a hydrocarbon stream containing isoprene and cyclopentadiene which involves contacting the stream with a base wherein said base is selected from the group consisting of potassium hydroxide, sodium hydroxide and potassium fluoride. The base is situated on activated carbon carrier.Type: GrantFiled: February 22, 1982Date of Patent: July 5, 1983Assignee: The Goodyear Tire & Rubber CompanyInventor: Richard M. D'Sidocky
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Patent number: 4390742Abstract: A process for reducing the level of cyclopentadiene present in a hydrocarbon stream containing isoprene and cyclopentadiene which involves contacting the stream with an alkali metal hydroxide wherein the reaction product is an insoluble salt of CPD.Type: GrantFiled: February 22, 1982Date of Patent: June 28, 1983Assignee: The Goodyear Tire & Rubber CompanyInventor: Lawson G. Wideman
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Patent number: 4356339Abstract: A process for isolating and recovering butene-1 of high purity at a high yield is provided. The process comprises the steps of continuously passing a butane-butene fraction containing 0.1 to 15 wt % of isobutylene and 10 to 50 wt % of butene-1 through a first reactor packed with a strongly acidic cation exchange resin having an average particle size of from 0.2 to 10 mm at a temperature of from 30.degree. to 100.degree. C. and at a space velocity of liquid of from 0.1 to 50 hr.sup.-1 under a pressure of from 1 to 50 atm., dividing the output mixture flowing out of said first reactor into two flows at a division ratio in flow rate of 1.about.15:1, recirculating the first flow having the flow rate of 1.about.Type: GrantFiled: December 7, 1981Date of Patent: October 26, 1982Assignee: Nippon Oil Company, LimitedInventors: Masao Imaizumi, Tetsuya Takezono, Takaaki Amari, Yutaka Oguchi