Organic Patents (Class 502/28)
  • Patent number: 5183933
    Abstract: Provided is a continuous process for producing 2,6-naphthalenedicarboxylic acid by the liquid phase oxidation of 2,6-dimethylnaphthalene comprising continuously adding to a reaction zone the oxidation reaction components comprising 2,6-dimethylnaphthalene, a source of molecular oxygen, a solvent comprising an aliphatic monocarboxylic acid, and a catalyst comprising cobalt, manganese and bromine components, wherein the atom ratio of manganese to cobalt is about 5:1 to about 0.3:1, the total of cobalt and manganese is at least about 0.40 weight percent based on the weight of solvent, and maintaining the contents of the reaction zone at a temperature of about 370.degree. F. to about 420.degree. F. and at a pressure sufficient to maintain at least a portion of the monocarboxylic acid in the liquid phase thereby oxidizing the 2,6-dimethylnaphthalene to 2,6-naphthalenedicarboxylic acid.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: February 2, 1993
    Assignee: Amoco Corporation
    Inventors: Jon J. Harper, George E. Kuhlmann, Keith D. Larson, Rosemary F. McMahon, Paul A. Sanchez
  • Patent number: 5141904
    Abstract: A spent metal contaminated zeolite-containing catalytic cracking catalyst composition is reactivated by a process which comprises contacting with an aqueous solution of at least one carboxylic acid (preferably at least one of formic acid, acetic acid, citric acid and lactic acid). The thus reactivated catalyst composition can be employed in a catalytic cracking process.
    Type: Grant
    Filed: February 15, 1991
    Date of Patent: August 25, 1992
    Assignee: Phillips Petroleum Company
    Inventors: Donald H. Kubicek, Chia-Min Fu, Richard E. Lowery, Michael K. Maholland
  • Patent number: 5100850
    Abstract: Disclosed is an oxidative process for recovering rhodium catalyst values from "tars" formed during the preparation of acetic anhydride by the rhodium catalyzed carbonylation of a mixture of methyl iodide and methyl acetate and/or dimethyl ether. The disclosed process includes the treatment of a tar/methyl iodide solution, which contains rhodium values normally not extracted by aqueous hydrogen iodide, with a solution of hydrogen peroxide and acetic acid.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: March 31, 1992
    Assignee: Eastman Kodak Company
    Inventors: Carl F. Fillers, Eric D. Middlemas, Charles E. Outlaw, Jerry A. Barron
  • Patent number: 5068477
    Abstract: This invention concerns a process for reducing a refining catalyst before it is put into use, the catalyst containing a support and an active phase based on at least one noble or non-noble metal of group VIII or of group Ib of the periodic classification of elements, consisting of:(a) impregnating the catalyst with an aqueous or organic solution of a reducing agent,(b) decomposing the reducing agent by heating with a catalyst, and(c) drying the catalyst thus obtained.The catalyst is used in selective hydrogention of a feed such as olefin, acetylenes, diolefins etc.
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: November 26, 1991
    Assignee: Europeenne de Retraitement de Catalyseurs Eurecat
    Inventor: Georges Berrebi
  • Patent number: 4960862
    Abstract: A process is provided for regenerating metallo-organic catalyst used in copolymerizing carbon dioxide with epoxides to form poly(alkylene carbonates). The catalyst is a polyvalent metal dicarboxylate and the regeneration procedure involves contacting spent or deactivated catalyst with dicarboxylic acid, preferably in a slurry. In one aspect the copolymerization is carried out and catalyst is separated from the polymerization mixture, reactivated with the dicarboxylic acid, such as glutaric or adipic acid, and reused in copolymerization to form poly(alkylene carbonate).
    Type: Grant
    Filed: March 31, 1989
    Date of Patent: October 2, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventors: W. Eamon Carroll, Stephen A. Motika
  • Patent number: 4952542
    Abstract: Cyclic alkylene carbonates are produced by the homogeneous catalytic reaction of alkylene oxides with carbon dioxide during which process, polyglycols are formed. The catalyst is separated by distillation from the alkylene carbonate and is recycled to the reaction while associated with polyglycols. A purge stream is removed from the recycle to prevent an undue concentration of polyglycols in the reaction and catalyst is separated from the purge stream by acylation of the polyglycols enabling precipitation of the catalyst.
    Type: Grant
    Filed: August 4, 1989
    Date of Patent: August 28, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: Bernard C. Ream
  • Patent number: 4950629
    Abstract: The present invention provides a process for recovering homogeneous metallic catalysts from catalytic reaction mixtures, in active form, suitable for immediate re-use. The process comprises removing the reaction solution solvent, adding a lower alkanoic acid, and recovering the precipitated homogeneous catalyst.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: August 21, 1990
    Assignee: Eli Lilly and Company
    Inventor: Christina C. Bodurow
  • Patent number: 4945075
    Abstract: Disclosed is a process for recovering rhodium catalyst values from "tars" formed during the preparation of acetic anhydride by the rhodium catalyzed carbonylation of a mixture of methyl iodide and methyl acetate and/or dimethyl ether. The disclosed process provides a means for the recovery of rhodium values which normally are not extracted from the tars by treating a methyl iodide solution of such tars with certain oxidants.
    Type: Grant
    Filed: December 4, 1989
    Date of Patent: July 31, 1990
    Assignee: Eastman Kodak Company
    Inventors: Michael R. Cushman, Vincent A. Nicely, Brent A. Tennant, Joseph R. Zoeller
  • Patent number: 4944927
    Abstract: A process for recovering Group VIII metals from process streams derived from carbonylation processes is provided. The process comprises contacting the process stream with an extracting stream comprising acetic acid in water and thereafter recovering the extracting stream. The process stream is preferably one which contains tar and is produced by diluting a side stream from a carbonylation reactor with methyl iodide. During the process the Group VIII metal is extracted into the extracting stream from the process stream.
    Type: Grant
    Filed: May 17, 1989
    Date of Patent: July 31, 1990
    Assignee: BP Chemicals Limited
    Inventor: David J. Gulliver
  • Patent number: 4910175
    Abstract: Recovery of cobalt and manganese catalyst from oxidation process, by precipitation with oxalic acid and alkali metal hydroxide, followed by oxidation of the precipitate in acetic acid to form cobalt and manganese acetate.
    Type: Grant
    Filed: December 12, 1988
    Date of Patent: March 20, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Robert E. Michel, Matthew R. Kegelman, Frederick J. Sebelist
  • Patent number: 4876386
    Abstract: A process is disclosed for the oxidation of di- or trimethyl benzenes with molecular oxygen under liquid-phase conditions in the presence of a recovered cobalt and manganese catalyst, which has been recovered by heating oxidation incinerator ash in the presence of acetic acid and a reducing agent wherein the weight ratio of acetic acid to said oxidation incinerator ash is from about 1:1 to about 50:1, and the ratio of electrons which the reducing agent can deliver to atoms of the cobalt plus manganese in the oxidation incinerator ash is from about 0.1:1 to about 4:1 at about the boiling point of the acetic acid at atmospheric pressure and recovering the cobalt and manganese in liquid solution as the metal acetic acid salt, wherein the oxidation is carried out at a temperature of from about 100.degree. C. to about 250.degree. C.
    Type: Grant
    Filed: May 26, 1988
    Date of Patent: October 24, 1989
    Assignee: Amoco Corporation
    Inventors: Juergen K. Holzhauer, Dennis J. Michalak, Wayne P. Schammel
  • Patent number: 4861738
    Abstract: The present invention relates to a process for the regeneration and stabilization of certain phosphorus-vanadium-oxygen complex catalysts or phosphorus-vanadium-oxygen co-metal complex catalysts, with halogen-containing components and subsequently treating the catalyst with phosphorus compounds. These catalysts are useful for the manufacture of maleic anhydride from butane feedstock.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: August 29, 1989
    Assignee: Amoco Corporation
    Inventor: Robert C. Edwards
  • Patent number: 4830997
    Abstract: The process has as an object the regeneration of catalysts containing at least one contaminating metal of the vanadium, nickel and iron group. The operation is conducted as follows:(a) The catalyst (1) is roasted in the presence of an oxygen-containing gas so as to remove at least 90% of the sulfur;(b) The catalyst obtained in step (a) is contacted with a hydrogen peroxide aqueous solution containing at least one organic compound comprising an acidic functional group, so as to remove at least 10% of the deposited metals of the vanadium, nickel and iron group; and(c) The regenerated catalyst (11) is separated from the aqueous solution of metal ions (5). The latter can be regenerated by passage over a complexing resin (6).The process is applicable to the regeneration of used catalysts, particularly to hydrotreatment catalysts in the oil industry.
    Type: Grant
    Filed: September 4, 1987
    Date of Patent: May 16, 1989
    Assignee: Institut Francais du Petrole
    Inventors: Dinh Chan Trinh, Alain Desvard, Germain Martino
  • Patent number: 4826792
    Abstract: A method for reactivating noble metal-containing zeolites containing sulfur oxide poisoned noble metal such as oxygen regenerated platinum zeolite beta catalysts, by contacting the catalyst with an acidic aqueous solution having a pH below about 7. The solution contains a Bronsted acid compound having a dissociation constant ranging from about 1.times.10.sup.-14 to about 2.times.10.sup.-1.
    Type: Grant
    Filed: May 5, 1988
    Date of Patent: May 2, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Quang N. Le, Stephen S. Wong
  • Patent number: 4822760
    Abstract: A process of regenerating a palladium salt catalyst comprising, in combination, steps of:(I) heating an organic residue containing a palladium salt catalyst which has been separated from a reaction solution, at a temperature of not lower than 330.degree. C. under an inert gas atmosphere to produce a reduced and thermally decomposed porous product;(II) firing the porous product produced in the step I under an oxygen-containing atmosphere; and(III) treating the product fired in the step II with an acid to produce a palladium salt.
    Type: Grant
    Filed: December 24, 1987
    Date of Patent: April 18, 1989
    Assignee: UBE Industries, Ltd.
    Inventors: Masaki Kashibe, Hideyuki Sugishita, Nobuyoshi Okada
  • Patent number: 4786752
    Abstract: A method is disclosed for recovery and recycle of metal catalyst components of a catalyst from the liquid-phase oxidation of pseudocumene in the presence of an oxidation catalyst comprising cobalt, manganese, and bromine components or cobalt, manganese, zirconium and bromine components wherein said catalyst components are recovered by oxalate precipitation from aqueous residue.
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: November 22, 1988
    Assignee: Amoco Corporation
    Inventors: Juergen K. Holzhauer, Wayne P. Schammel, Neal R. Nowicki
  • Patent number: 4786621
    Abstract: A process is disclosed for recovery of cobalt and manganese, and other metals, in the form of their acetate salts, directly from mixed metal oxides present in oxidation residue incinerator ash comprising fly ash and clinkers from incineration of a residue from manufacture of benzene di- and tricarboxylic acids by catalytic means. These acetate salts are recycled directly for manufacture of benzene di- and tricarboxylic acids after recovery.
    Type: Grant
    Filed: June 17, 1987
    Date of Patent: November 22, 1988
    Assignee: Amoco Corporation
    Inventors: Juergen K. Holzhauer, Dennis J. Michalak, Wayne P. Schammel
  • Patent number: 4717696
    Abstract: Supported zerovalent palladium used in the hydrogenation of aldose cyanohydrins is rapidly deactivated. A regeneration procedure based on a water wash and acid treatment effectively restores catalyst activity to its original level. Such a regeneration procedure may be used over several cycles to afford a catalyst with essentially unaltered activity.
    Type: Grant
    Filed: October 31, 1986
    Date of Patent: January 5, 1988
    Assignee: UOP Inc.
    Inventor: Blaise J. Arena
  • Patent number: 4714688
    Abstract: The process has as an object the regeneration catalysts containing at least one contaminating metal of the vanadium, nickel and iron group. The operation is conducted as follows:(a) The catalyst (1) is roasted in the presence of an oxygen-containing gas so as to remove at least 90% of the sulfur;(b) The catalyst obtained in step (a) is contacted with a hydrogen peroxide aqueous solution containing at least one organic compound including a polar functional group, so as to remove at least 10% of the deposited metals of the vanadium, nickel and iron group; and(c) The regenerated catalyst (11) is separated from the aqueous solution of metal ions (5). The latter can be regenerated by passage over a complexing resin (6).The process is applicable to the regerneration of used catalysts, particularly to hydrotreatment catalysts in the oil industry.
    Type: Grant
    Filed: March 7, 1986
    Date of Patent: December 22, 1987
    Assignee: Institut Francais du Petrole
    Inventors: Chan Trinh Dinh, Alain Desvard, Germain Martino
  • Patent number: 4678764
    Abstract: A method for reactivating noble metal-containing zeolites containing sulfur oxide poisoned noble metal such as oxygen regenerated platinum zeolite beta catalysts, by contacting the catalyst with an acidic aqueous solution having a pH below about 7. The solution contains a Bronsted acid compound having a dissociation constant ranging from about 1.times.10.sup.-14 to about 2.times.10.sup.-1.
    Type: Grant
    Filed: November 21, 1985
    Date of Patent: July 7, 1987
    Assignee: Mobil Oil Corporation
    Inventors: Quang N. Le, Ying-Yen P. Tsao, Stephen S. Wong
  • Patent number: 4677085
    Abstract: This invention pertains to a new process for removing metals, especially contaminant metals, from spent catalysts. Also, this invention pertains to a catalyst composite with metals removed by the new process, and to several uses for the catalyst, including as a rejuvenated hydrotreating catalyst. The new process comprises (i) contacting the spent catalyst with a complexing agent with four or more coordinating groups, including at least two carboxylic acid type groups and at least one amino type group, and (ii) separating from the spent catalyst a mixture containing the complexing agent and the removed metals. By this process contaminant metals, like vanadium, are more selectively removed from the spent catalyst than are catalytic metals, like cobalt and molybdenum.
    Type: Grant
    Filed: September 30, 1985
    Date of Patent: June 30, 1987
    Assignee: Amoco Corporation
    Inventor: Thomas D. Nevitt
  • Patent number: 4663304
    Abstract: A process for the disproportionation of olefins is disclosed employing a novel catalyst comprising an inorganic oxide support contacted with at least one of tungsten or molybdenum oxide or oxide precursor and at least one acid. Method for preparation of catalyst is also provided.
    Type: Grant
    Filed: September 27, 1985
    Date of Patent: May 5, 1987
    Assignee: Phillips Petroleum Company
    Inventors: Charles A. Drake, Robert E. Reusser
  • Patent number: 4659684
    Abstract: Described is a process for removing arsenic, vanadium, and/or nickel from petroliferous derived liquids by contacting said liquid at an elevated temperature with a divinylbenzene-crosslinked polystyrene having catechol ligands anchored thereon. For vanadium and nickel removal an amine, preferably a diamine is included.Also, described is a process for regenerating spent catecholated polystyrene by removal of the arsenic, vanadium, and/or nickel bound to it from contacting petroliferous liquid as described above and involves:treating the spent polymer containing any vanadium and/or nickel with an aqueous acid to achieve an acid pH; and,separating the solids from the liquid; and thentreating said spent catecholated polystyrene, at a temperature in the range of about 20.degree. to 100.degree. C. with an aqueous solution of at least one carbonate and/or bicarbonate of ammonium, alkali and alkaline earth metals, said solution having a pH between about 8 and 10; and,separating the solids and liquids from each other.
    Type: Grant
    Filed: March 21, 1986
    Date of Patent: April 21, 1987
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventor: Richard H. Fish
  • Patent number: 4659682
    Abstract: Heavy residues produced by noble metal catalyzed carbonylation reactions and containing Group VIII noble metals, particularly rhodium, are treated with reagents to precipitate solids containing substantially all of the noble metal contained in the residues. The solids may be further treated to concentrate the noble metals or they may be returned directly for reuse in the carbonylation reaction. Suitable reagents include aliphatic alcohols, carboxylic acids, and carboxylic acid esters. Preferred are branched-chain alcohols, especially tertiary alcohols; of the acids, acetic acid is particularly preferred; and of the esters, n-butyl acetate and ethylidene diacetate are preferred. Subsequent treatments with other solvents, e.g., alkanes, cycloalkanes, ethers, and aromatic compounds, may be used to further concentrate the rhodium content of the precipitated solids.
    Type: Grant
    Filed: July 8, 1985
    Date of Patent: April 21, 1987
    Assignee: The Halcon SD Group, Inc.
    Inventor: Joseph Pugach
  • Patent number: 4656147
    Abstract: A method for recovering a denitrating catalyst for ammonia catalytic reduction which is characterized by treating the denitrating catalyst for ammonia catalytic reduction, in which a performance has deteriorated, with at least one selected from the group consisting of SO.sub.4.sup.2- compounds, sulfur compounds and sulfonic acid compounds in order to replenish the catalyst with a sulfur content.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: April 7, 1987
    Assignee: Mitsubishi Jukogyo Kabushiki Kaisha
    Inventors: Kozo Iida, Tsuneo Nagano, Naruo Yokoyama, Yoshiaki Obayashi, Shigeaki Mitsuoka
  • Patent number: 4650649
    Abstract: This invention relates to a novel process for recovering catalyst components and, more particularly, to a method for recovering both iodine and noble metal components such as rhodium from tars formed during the preparation of acetic anhydride by the iodine and noble metal catalyzed carbonylation of methyl acetate.
    Type: Grant
    Filed: January 21, 1986
    Date of Patent: March 17, 1987
    Assignee: Eastman Kodak Company
    Inventor: Joseph R. Zoeller
  • Patent number: 4618702
    Abstract: Increased catalyst concentration relative to butadiene in its carboalkoxylation permits operation at reduced pressure and simplifies process steps.
    Type: Grant
    Filed: January 24, 1985
    Date of Patent: October 21, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Michael B. D'Amore, Roger R. Ellefson
  • Patent number: 4615991
    Abstract: A method for recovering a denitrating catalyst which is characterized by washing, with an aqueous oxalic acid solution, the used tungsten-titania or the tungsten-titania-vanadium denitrating catalyst which dust components have adhered to or have accumulated on and in which an SO.sub.2 -oxidizing power has thus risen; impregnating the catalyst with a tungsten compound; and drying and calcining the thus treated catalyst.
    Type: Grant
    Filed: April 2, 1985
    Date of Patent: October 7, 1986
    Assignee: Mitsubishi Jukogyo Kabushiki Kaisha
    Inventors: Yoshiaki Obayashi, Shigeaki Mitsuoka
  • Patent number: 4612293
    Abstract: A fluoride-containing platinum on alumina support isomerization catalyst useful for the isomerization of pentane to isopentane can be prepared by a several step treatment of substantially deactivated chloride-containing platinum on alumina support isomerization catalyst. The conversion steps include washing the chloride-containing catalyst to remove substantially all chloride ions, fluorinating the washed material with an aqueous florinating agent, then drying the fluorinated catalyst. Isomerization process employing the catalyst thus prepared is also provided.
    Type: Grant
    Filed: September 27, 1985
    Date of Patent: September 16, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Marvin M. Johnson
  • Patent number: 4608084
    Abstract: A process is disclosed for recovering cobalt and chromium from a cobalt and chromium containing alloy. The process involves first digesting the alloy in concentrated hydrochloric acid at a sufficient temperature for a sufficient time to form a first solution containing the major portion of the cobalt, chromium, and any iron and nickel present in the alloy and a first solid and separating the first solution from the first solid. Oxalic acid is then added to the first solution in an amount sufficient to subsequently precipitate the major portion of the cobalt and any iron and nickel contained in the first solution followed by adjustment of the ph to from about 1 to about 2 with a base and maintaining the temperature below about 20.degree.
    Type: Grant
    Filed: April 1, 1985
    Date of Patent: August 26, 1986
    Assignee: GTE Products Corporation
    Inventors: Richard A. Scheithauer, Michael J. Miller, Clarence D. Vanderpool, Martin B. MacInnis
  • Patent number: 4598057
    Abstract: The process of regenerating a stable organic soluble molybdenum-containing catalyst suitable for epoxidation of olefins with a hydroperoxide which comprises thermally precipitating and separating a molybdenum-containing solid obtained from a spent catalyst stream derived from a molybdenum catalyzed epoxidation of an olefin and solubilizing the precipitated solid by contacting with a liquid composition comprising a peroxy compound, a monohydroxy alcohol, optionally a polyhydroxy alcohol, and an organic dicarboxylic acid present in an amount of at least about 0.2 parts, by weight, of molybdenum contained in said solid.
    Type: Grant
    Filed: October 26, 1984
    Date of Patent: July 1, 1986
    Assignee: Atlantic Richfield Company
    Inventor: Bruce H. Isaacs
  • Patent number: 4595666
    Abstract: Spent catalysts removed from a catalytic hydrogenation process for hydrocarbon feedstocks, and containing carbon undesired metals contaminants deposits, are rejuvenated for reuse. Following solvent washing to remove process oils, the catalyst is treated either with chemicals which form sulfate or oxysulfate compounds with the metals contaminants, or with acids which remove the metal contaminants, such as 5-50 W % sulfuric acid in aqueous solution and 0-10 W % ammonium ion solutions to substantially remove the metals deposits. The acid treating occurs within the temperature range of 60.degree.-250.degree. F. for 5-120 minutes at substantially atmospheric pressure, after which the rejuvenated catalyst containing carbon deposits can be effectively reused in the catalytic hydrogenation process.
    Type: Grant
    Filed: April 30, 1984
    Date of Patent: June 17, 1986
    Assignee: HRI, Inc.
    Inventor: Partha S. Ganguli
  • Patent number: 4578367
    Abstract: The catalytic cobalt compound used in the reaction of olefins with carbon monoxide and water or alkanols which employs an oxidizing treatment is reprocessed according to the present invention. This reprocessing includes in a first embodiment treating the cobaltic residue obtained as the distillation sump product with water and a carboxylic acid having 1 to 4 C atoms. The phases generated are separated and cobalt is recovered from the carboxylic acid/water phase in the form of the corresponding carboxylic acid salt. Where appropriate, the corresponding carboxylic acid salt is transformed into another carboxylic-acid salt.A second embodiment includes the steps of hydrogenating the cobalt containing residue obtained as the distillation sump product, separating the metallic cobalt which is obtained, reacting the metallic cobalt with an acid and where appropriate converting the cobalt salt so obtained into another cobalt salt.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: March 25, 1986
    Assignee: Chemische Werke Huls Aktiengesellschaft
    Inventor: Peter Hofmann
  • Patent number: 4578368
    Abstract: Disclosed is a process for the recovery of noble metals from a catalyst-tar formed in a process in which acetic anhydride is prepared by carbonylating methyl acetate in the presence of a noble metal containing catalyst such as rhodium, lithium and methyl iodide. The rhodium is recovered from the tar formed in the process by treating the catalyst containing tar with a lower fatty acid at a temperature of at least 100.degree. C. thereby isolating the noble metal which precipitates from the tar.
    Type: Grant
    Filed: May 6, 1985
    Date of Patent: March 25, 1986
    Assignee: Eastman Kodak Company
    Inventor: Joseph R. Zoeller
  • Patent number: 4548911
    Abstract: Regeneration of a phosphorus poisoned automotive exhaust catalyst is accomplished in a preferred embodiment by washing the catalyst or soaking it to the point of incipient wetness with an aqueous solution of an acid such as HCl, HNO.sub.3 or oxalic acid and subsequent heating of the wetted catalyst in air or other oxygen-containing gas.
    Type: Grant
    Filed: October 17, 1984
    Date of Patent: October 22, 1985
    Assignee: General Motors Corporation
    Inventors: Michael J. D'Aniello, Jr., David R. Monroe, Martin H. Krueger
  • Patent number: 4548700
    Abstract: A slurry hydroconversion process is provided in which a carbonaceous chargestock such as a hydrocarbonaceous oil or coal comprising a catalyst containing vanadium or molybdenum or mixtures thereof, is converted to a hydroconverted oil product. A heavy oil portion comprising metal-containing solids is separated from the oil product and partially gasified to produce a carbon-free metal-containing ash which is extracted with oxalic acid. The resulting metal-containing oxalic acid extract is recycled to the hydroconversion zone as catalyst precursor.
    Type: Grant
    Filed: December 14, 1983
    Date of Patent: October 22, 1985
    Assignee: Exxon Research and Engineering Co.
    Inventors: Roby Bearden, Jr., Clyde L. Aldridge
  • Patent number: 4546202
    Abstract: A process for the recovery of cobalt and manganese from solid aromatic acid oxidation incinerator ash, pyrolysis sand and pyrolysis char is disclosed. The process comprises heating the solid residue at a temperature of about 120.degree. to about 300.degree. C. and a pressure of about 3 atmospheres to about 30 atmospheres. The recovered catalyst is useful for the oxidation of alkyl aromatic hydrocarbons to their corresponding di- or tricarboxylic acids which are used for the manufacture of fibers, films and molded products.
    Type: Grant
    Filed: November 29, 1983
    Date of Patent: October 8, 1985
    Assignee: Amoco Corporation
    Inventors: Robert C. Edwards, F. Austin Golson
  • Patent number: 4522928
    Abstract: A process for removing metal contaminants from a hydroconversion catalyst, said catalyst containing at least one metal from Groups VIB, VIIB or VIII supported on a refractory inorganic oxide. The process comprises contacting the contaminated catalyst with a buffered oxalic acid solution wherein contaminant is removed without dissolving the support.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: June 11, 1985
    Assignee: Exxon Research and Engineering Co.
    Inventors: Gary B. McVicker, James L. Carter, Lawrence L. Murrell, John J. Ziemiak
  • Patent number: 4521526
    Abstract: The catalytic cobalt compound used in the reaction of olefins with carbon monoxide and water or alkanols which employs an oxidizing treatment is reprocessed according to the present invention. This reprocessing includes in a first embodiment treating the cobaltic residue obtained as the distillation sump product with water and a carboxylic acid having 1 to 4 C atoms. The phases generated are separated and cobalt is recovered from the carboxylic acid/water phase in the form of the corresponding carboxylic acid salt. Where appropriate, the corresponding carboxylic acid salt is transformed into another carboxylic-acid salt.A second embodiment includes the steps of hydrogenating the cobalt containing residue obtained as the distillation sump product, separating the metallic cobalt which is obtained, reacting the metallic cobalt with an acid and where appropriate converting the cobalt salt so obtained into another cobalt salt.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: June 4, 1985
    Assignee: Chemische Werke Huls AG
    Inventor: Peter Hofmann
  • Patent number: 4501820
    Abstract: A tungsten-containing catalyst associated with coke containing vanadium and nickel is recovered by a method which includes steam gasification, low temperature burning to remove at least a portion of the coke and selective extraction of the nickel and vanadium.
    Type: Grant
    Filed: July 28, 1983
    Date of Patent: February 26, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: David E. Allan, Byron V. Molstedt, Raam R. Mohan
  • Patent number: 4486616
    Abstract: A process for alkylation of aromatic hydrocarbon reactants to dialkylbenzene products, whereby chemically modified zeolite catalysts are treated with an organic acid to enhance their intrinsic para-selectivity in the alkylation reaction. The modified zeolites which may be so reselectivated or improved comprise those crystalline zeolites having a constraint index of 1 to 12, a silica to alumina mole ratio of at least 12, and having a minor proportion of the oxide form of one or more chemical elements (e.g. phosphorus and magnesium) deposited thereon.
    Type: Grant
    Filed: May 12, 1983
    Date of Patent: December 4, 1984
    Assignee: Mobil Oil Corporation
    Inventors: Chin-Chiun Chu, Warren W. Kaeding
  • Patent number: 4485183
    Abstract: Deactivated hydrorefining catalysts are regenerated by incorporation of as phosphorus component followed by combustive coke-removal from the catalyst. The regenerated catalyst is useful for promoting hydrodesulfurization reactions, particularly those involving demetallation of hydrocarbons.
    Type: Grant
    Filed: April 12, 1982
    Date of Patent: November 27, 1984
    Assignee: Union Oil Company of California
    Inventors: Richard B. Miller, Ryden L. Richardson
  • Patent number: 4476237
    Abstract: Tarry residues often are formed in carbonylation reactions, such as those in which esters or ethers are carbonylated to produce ethylidene diacetate or carboxylic acid anhydrides, such as acetic anhydride. Such residues contain Group VIII noble metal catalysts, typically rhodium, which must be separated before the residues can be disposed of. In the process of the invention, a portion of the carbonylation reaction mixture is flashed to a lower pressure and the resulting residues-containing liquid is extracted with solvents which preferentially remove the tars. The tars are separated from the solvents and disposed of while the solvents are recycled for further use. The catalyst-containing liquid is processed to remove residual solvent and returned to the carbonylation reaction.
    Type: Grant
    Filed: May 28, 1981
    Date of Patent: October 9, 1984
    Assignee: The Halcon SD Group, Inc.
    Inventor: Richard V. Porcelli
  • Patent number: 4476238
    Abstract: Tarry residues often are formed in carbonylation reactions, such as those in which esters or ethers are carbonylated to produce ethylidene diacetate or carboxylic acid anhydrides, such as acetic anhydride. Such residues contain Group VIII noble metal catalysts, typically rhodium, which must be separated before the residues can be disposed of. In the process of the invention, the residues are extracted with solvents which preferentially dissolve the tars. Preferred solvents include alkanes, cycloalkanes, halogenated alkanes, and aromatic hydrocarbons, particularly cyclohexane, carbon tetrachloride, and toluene. Separation of the residues from the noble metal catalyst by solvent extraction makes possible the disposal of the residues and the return of the noble metals to the reaction for reuse.
    Type: Grant
    Filed: May 28, 1981
    Date of Patent: October 9, 1984
    Assignee: The Halcon SD Group, Inc.
    Inventors: Burton J. Palmer, Joseph V. Posluszny
  • Patent number: 4464477
    Abstract: A process for the recovery and reuse of heavy metal oxidation catalyst from residues in the Witten DMT process by extraction, which involves mixing and settling of the residue with water or dilute aqueous solutions of water-soluble, low-molecular, aliphatic monocarboxylic acids at 70.degree.-160.degree. C. and recycling of the extract of the high-boiling distillation residues into the DMT process. The high-boiling distillation residue and the extractant are used in a quantitative ratio of 1:0.9 to 1:0.1, preferably 1:0.5 to 1:0.3.
    Type: Grant
    Filed: December 1, 1981
    Date of Patent: August 7, 1984
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Heinrich Bunger, Rudolf Cordes, Gerhard Hoffmann
  • Patent number: 4454240
    Abstract: Spent catalysts removed from a catalytic hydrogenation process for hydrocarbon feedstocks, and containing undesired metals contaminants deposits, are regenerated. Following solvent washing to remove process oils, the catalyst is treated either with chemicals which form sulfate or oxysulfate compounds with the metals contaminants, or with acids which remove the metal contaminants, such as 5-50 W % sulfuric acid in aqueous solution and 0-10 W % ammonium ion solutions to substantially remove the metals deposits. The acid treating occurs within the temperature range of 60.degree.-250.degree. F. for 5-120 minutes at substantially atmospheric pressure. Carbon deposits are removed from the treated catalyst by carbon burnoff at 800.degree.-900.degree. F. temperature, using 1-6 V % oxygen in an inert gas mixture, after which the regenerated catalyst can be effectively reused in the catalytic process.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: June 12, 1984
    Assignee: HRI, Inc.
    Inventor: Partha S. Ganguli
  • Patent number: 4434241
    Abstract: The present invention provides a process for the recovery of rhodium, lithium, and iodine values from tar which is generated during carbonylation reactions. The process comprises sequentially extracting the tar with water and then leaching the remaining tar with acetic acid, burning the resulting residue, and recycling the resulting rhodium-enriched residue to the reaction process. Preferably, the process further comprises the recovery of iodine values by the incineration of the acetic acid leachate and treatment of the off-gas with aqueous alkali hydroxide. Lithium values are recovered by evaporating water from the aqueous phase of the water extraction step and recycling the resulting residue to the reaction process.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: February 28, 1984
    Assignee: Eastman Kodak Company
    Inventor: Thomas H. Larkins, Jr.
  • Patent number: 4410449
    Abstract: A process for the recovery and reuse of a heavy-metal oxidation catalyst solution from a high-boiling distillation residue having a cobalt content of 1-10 g/kg of residue is disclosed. The distillation residue is obtained in the production of dimethyl terephthalate by the oxidation of mixtures containing p-xylene and/or methyl p-toluate in the liquid phase with oxygen or an oxygen-containing gas under an elevated pressure and at an elevated temperature in the presence of dissolved heavy-metal oxidation catalyst, by subsequent esterification of the oxidation product with methanol and by a distillatory separation of the esterification product into a fraction rich in methyl p-toluate, a fraction rich in dimethyl terephthalate, and the high-boiling distillation residue.
    Type: Grant
    Filed: August 12, 1982
    Date of Patent: October 18, 1983
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Karl-Heinz Diessel, Rudolf Modic, Friedrich Struss