Patents Represented by Attorney John W. Ditsler
  • Patent number: 4096199
    Abstract: A process for regenerating an alkylation catalyst comprising fluorosulfuric acid, said catalyst being at least partially deactivated, which comprises:(1) contacting at least a portion of the fluorosulfuric acid with water to form an acid-water mixture, thereby converting at least a portion of the fluorosulfuric acid therein to hydrogen fluoride and sulfuric acid;(2) removing at least a portion of the hydrogen fluoride from said acid-water mixture formed in step (1) by contacting same with a stripping agent to form a gaseous phase containing hydrogen fluoride and said stripping agent and a liquid phase containing sulfuric acid and sludge;(3) cooling the gas phase formed in step (2) to a temperature sufficient to form a mixed phase comprising at least a liquid phase containing hydrogen fluoride; and(4) treating the mixed phase formed in step (3) with sulfur trioxide under substantially liquid phase conditions so as to regenerate the fluorosulfuric acid.
    Type: Grant
    Filed: February 28, 1977
    Date of Patent: June 20, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventors: Donald L. Green, William C. Behrmann, David E. Allan
  • Patent number: 4096197
    Abstract: An improved process for regenerating an alkylation catalyst comprising fluorosulfuric acid, said catalyst being at least partially deactivated, which comprises the method of:(1) removing a portion of the fluorosulfuric acid from said catalyst by contacting same with a paraffin to form a liquid acid phase containing fluorosulfuric acid and an organic sludge formed during said alkylation and a gas phase containing said paraffin and fluorosulfuric acid;(2) contacting the liquid acid phase formed in step (1) with water to form an acid-water mixture, thereby coverting at least a portion of the fluorosulfuric acid contained therein to hydrogen fluoride and sulfuric acid;(3) removing at least a portion of the hydrogen fluoride from said acid-water mixture formed in step (2) by contacting same with a paraffin to form a gaseous phase containing hydrogen fluoride and paraffin; and(4) treating the gas phases formed in steps (1) and (3) with sulfur trioxide to regenerate the fluorosulfuric acid.
    Type: Grant
    Filed: February 28, 1977
    Date of Patent: June 20, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventor: Ivan Mayer
  • Patent number: 4096198
    Abstract: An integrated process for regenerating a deactivated or partially deactivated alkylation catalyst comprising fluorosulfuric acid which comprises:(1) contacting said fluorosulfuric acid with water to form an acid-water mixture, thereby converting at least a portion of the fluorosulfuric acid therein to hydrogen fluoride and sulfuric acid;(2) removing at least a portion of the hydrogen fluoride from said acid-water mixture formed in step (1) by contacting same with a paraffin to form a gaseous phase containing hydrogen fluoride and said paraffin;(3) cooling the gaseous phase formed in step (2) by contacting with liquid paraffin to condense a portion of the fluorosulfuric acid present in said gaseous phase, thereby forming a liquid phase and a gaseous phase each containing fluorosulfuric acid and hydrogen fluoride;(4) treating the liquid and gaseous phases formed in step (3) with liquid sulfur trioxide to form a mixture comprising a liquid phase containing regenerated fluorosulfuric acid and a gas phase containi
    Type: Grant
    Filed: February 28, 1977
    Date of Patent: June 20, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventors: Albert J. Mariconda, Kenneth J. Reinman, Ivan Mayer
  • Patent number: 4094924
    Abstract: Alkylates are prepared by selectively alkylating light paraffinic hydrocarbons with lower olefins at alkylation conditions in the presence of a catalyst comprising (a) one or more Lewis acids of the formula MX.sub.n where M is selected from the Group IIIA, V or VIB elements of the Periodic Table, X is a halogen, n is the ratio of halogen atoms to atoms of M and varies from 1-8, and (b) a hydrogen halide.
    Type: Grant
    Filed: July 18, 1977
    Date of Patent: June 13, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventors: Michael Siskin, Ivan Mayer
  • Patent number: 4075251
    Abstract: Novel hydrogenation catalysts are formed by impregnating a suitable support material with an aqueous solution of a salt of a transition metal; heat-treating the impregnated support at a temperature above 500.degree. F. to form chemical complexes on the surface of the support and to drive off moisture and absorbed oxygen; activating the surface complex by contacting the impregnated support with a soluble crganometallic compound wherein the metal constituent is selected from Groups I, II and III of the Periodic Chart of the Elements, and thereafter treating the activated support material in the presence of a gaseous stream containing hydrogen at a temperature of at least 300.degree. F. to form a highly stable heterogeneous catalyst. The novel supported catalysts of the instant invention have been found to be highly active for the hydrogenation of organic compounds under extremely mild conditions.
    Type: Grant
    Filed: August 30, 1976
    Date of Patent: February 21, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventors: Joseph K. Mertzweiller, Horace M. Tenney
  • Patent number: 4073821
    Abstract: Sulfur dioxide is employed as a stripping agent in the regeneration of a deactivated or partially deactivated alkylation catalyst containing fluorosulfuric acid, thereby eliminating undesirable reactions that occur between the acid component of said catalyst and the hydrocarbon stripping agents normally employed in conventional fluorosulfuric acid regeneration processes.
    Type: Grant
    Filed: February 28, 1977
    Date of Patent: February 14, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventor: Michael Siskin
  • Patent number: 4073822
    Abstract: The equivalent water content of hydrocarbon conversion catalyst comprising water and fluorosulfuric acid, i.e. the water equivalent to the water used to form the active catalyst, is determined continuously by contacting SO.sub.3, e.g. fuming sulfuric acid, with said catalyst in a flow ratio sufficient to maintain the mixture thus formed at the point of incipient fuming. The presence of SO.sub.3 evolved therefrom is determined by use of an SO.sub.3 detector. The flow ratio at the point of incipient fuming is a direct measure of the equivalent water used to form the catalyst system. The equivalent water content thus measured is then compared to the desired equivalent water content and a signal corresponding to the deviation is used to vary the rate of fresh acid makeup, the rate of water addition, or both to the hydrocarbon conversion process reaction zone so as to maintain the desired equivalent water content of the catalyst therein.
    Type: Grant
    Filed: January 3, 1977
    Date of Patent: February 14, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventor: Ivan Mayer
  • Patent number: 4071576
    Abstract: The deactivated fluorosulfuric acid catalyst in olefin-paraffin alkylation is regenerated by (1) contacting the acid phase with water to form an acid-water mixture (2) stripping the acid-water mixture with a paraffin to form a gaseous phase of hydrogen fluoride and paraffin (3) cooling the gaseous phase with liquid paraffin to form a liquid fluorosulfuric acid and a vapor containing fluorosulfuric acid, hydrogen fluoride and paraffin (4) treating the vapor with liquid SO.sub.3, and utilizing liquid fluorosulfuric acid in the treating step in countercurrent flow to the vapor to convert the hydrogen fluoride to regenerated fluorosulfuric acid, (5) the remaining gas phase containing paraffin and a minor amount of fluorosulfuric acid is cooled to condense all the fluorosulfuric acid to liquid and (6) the regenerated liquid fluorosulfuric acid is used as the countercurrent flowing liquid fluorosulfuric acid in treating step (4).
    Type: Grant
    Filed: February 28, 1977
    Date of Patent: January 31, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventors: William C. Behrmann, Robert H. Caulk
  • Patent number: 4069268
    Abstract: Deactivated or partially deactivated hydrocarbon conversion catalysts comprising (a) one or more Lewis acids of the formula MX.sub.n where M is a component selected from Group IIIA, IVB, V, VIB or VIII Elements of the Periodic Table or their mixtures, X is a halogen, and n is the atomic ratio of halogen to M and varies from 1 to 8, and (b) a strong Bronsted acid, may be regenerated by contacting said catalysts with a halogen selected from the group consisting of fluorine or chlorine. If a portion of the catalyst has been hydrolyzed, the catalyst may be regenerated via halogenation as above or by contact with a hydrogen halide selected from the group consisting of hydrogen fluoride or hydrogen chloride and then fluorine. The preferred Lewis acid is a metal halide, preferably tantalum pentafluoride, niobium pentafluoride or mixtures thereof. The preferred Bronsted acid is a hydrogen halide, preferably hydrogen fluoride.
    Type: Grant
    Filed: November 4, 1975
    Date of Patent: January 17, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventors: Michael Siskin, Ronald J. Gillespie
  • Patent number: 4065405
    Abstract: Tantalum and/or niobium pentafluorides may be recovered from a deactivated or partially deactivated hydrocarbon conversion catalyst comprising (a) a metal pentafluoride selected from the group consisting of tantalum pentafluoride, niobium pentafluoride and mixtures thereof and (b) hydrogen fluoride, by distilling said catalyst in the presence of a Lewis acid containing neither of these Group V metals, thereby displacing a pentahalide of tantalum and/or niobium into the vapor phase from which it can be condensed. Addition of hydrogen fluoride then converts the pentahalide to the pentafluoride.
    Type: Grant
    Filed: December 3, 1976
    Date of Patent: December 27, 1977
    Assignee: Exxon Research and Engineering Company
    Inventor: Roger Hulme
  • Patent number: 4065516
    Abstract: Alkylates of enhanced product quality are prepared by isomerizing a mixed butenes-containing feed prior to alkylating said feed with a saturated hydrocarbon, preferably an isoparaffin, in the presence of a catalyst comprising a strong acid such as halosulfuric acid, trihalomethanesulfonic acid or mixtures thereof and a moderator containing at least one oxygen atom per molecule. A preferred catalyst is fluorosulfuric acid and water.
    Type: Grant
    Filed: December 19, 1975
    Date of Patent: December 27, 1977
    Assignee: Exxon Research and Engineering Company
    Inventors: John F. Moser, Jr., William C. Behrmann
  • Patent number: 4065381
    Abstract: A hydrocarbon phase separated from a hydrocarbon conversion process is solvent extracted with anhydrous liquid HF to separate metal pentafluoride which is carried over into the hydrocarbon phase. The extract of HF and metal fluoride is then combined with the catalyst phase (HF and metal pentafluoride) and stripped with hydrogen to reduce the molar ratio of HF to metal pentafluoride to the level that HF + metal pentafluoride catalyst is utilized in the hydrocarbon conversion process. The metal pentafluoride is TaF.sub.5 and/or NbF.sub.5 and the hydrocarbon conversion may involve isomerization, alkylation with olefins and reactions of a paraffin with another paraffin.
    Type: Grant
    Filed: December 29, 1976
    Date of Patent: December 27, 1977
    Assignee: Exxon Research and Engineering Company
    Inventors: Geoffrey R. Say, William C. Baird, Jr., Paul W. Kamienski
  • Patent number: 4064189
    Abstract: High octane alkylates are prepared by selectively alkylating paraffinic hydrocarbons with other paraffinic hydrocarbons at alkylation conditions in the presence of hydrogen and of a catalyst comprising a metal pentafluoride selected from the group consisting of tantalum pentafluoride, niobium pentafluoride and mixtures thereof and a hydrogen halide. The product obtained is a mixture containing primarily C.sub.4 -C.sub.6 isomerized paraffins.
    Type: Grant
    Filed: January 3, 1977
    Date of Patent: December 20, 1977
    Assignee: Exxon Research & Engineering Co.
    Inventors: Michael Siskin, Joseph J. Porcelli
  • Patent number: 4062761
    Abstract: The catalyst circulation rate in a fluid catalytic cracking process is regulated by using a low pressure drop valve means in the spent catalyst circuit of said process in conjunction with a control riser in said circuit. More particularly, a reduced catalyst circulation rate may be obtained in a fluid catalytic cracking process, the spent catalyst circulation rate in said process being controlled by the injection of variable amounts of a control gas into the control riser so as to cause density variations therein, by employing a low pressure drop valve means in the spent catalyst circuit of said process such that the pressure drop across said valve means reduces the pressure drop across the riser and consequently the density within said riser. The reduction in density within the riser results in a lowering of the catalyst circulation rate.
    Type: Grant
    Filed: November 28, 1975
    Date of Patent: December 13, 1977
    Assignee: Exxon Research and Engineering Company
    Inventor: Edward C. Luckenbach
  • Patent number: 4058575
    Abstract: Partially deactivated hydrocarbon conversion catalysts comprising (a) one or more Lewis acids of the formula MX.sub.n where M is a metal selected from Group III-A, IV-B, V or VI-B elements of the Periodic Table, X is a halogen, n is the ratio of halogen atoms to atoms of M and varies from 1-8, and (b) a strong Bronsted acid are contacted with a hydrocarbon feedstock to recover the active or potentially active catalyst species from the partially deactivated catalyst stream prior to regeneration. In addition, potential organic and inorganic catalyst poisons present in said feedstock are removed therefrom during said contacting prior to introducing said feedstock into a hydrocarbon conversion process.
    Type: Grant
    Filed: June 12, 1975
    Date of Patent: November 15, 1977
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert P. Cahn, John P. Longwell
  • Patent number: 4054644
    Abstract: Hydrogen is produced by reacting carbon monoxide with steam at a temperature of at least 200.degree. F. in the presence of a supported catalyst containing: (1) at least one alkali metal compound derived from an acid having an ionization constant below 1 .times. 10.sup.-3, (2) a metallic hydrogenation- dehydrogenation material, and (3) a halogen moiety. The ratio of metal component to alkali metal compound, each calculated on the basis of the oxide thereof, ranges from 0.0001 to about 10 parts by weight per part by weight of the alkali metal compound. The halide constituent is present in amounts in excess of about 0.01 weight %, based on total catalyst. A preferred catalyst composition comprises potassium carbonate, a mixture of cobalt and molybdenum oxides and combined chlorine contained on an alumina support.
    Type: Grant
    Filed: November 25, 1974
    Date of Patent: October 18, 1977
    Assignee: Exxon Research & Engineering Co.
    Inventors: Marnell A. Segura, Clyde L. Aldridge, Kenneth L. Riley, Lloyd A. Pine
  • Patent number: 4053396
    Abstract: Organic contaminants are removed from waste water streams by initially pretreating the stream to remove suspended solids and oil therefrom and thereafter passing the pretreated waste water through bed(s) of activated carbon while adding a controlled amount of oxygen to the bed(s) in an amount ranging from about 0.05 to about 0.15 pound of oxygen consumed per pound of total COD contaminants removed from the waste water by this process. By following the method of the present invention, the balance between the aerobic/anaerobic biological oxidation of the contaminants adsorbed on the activated carbon may be controlled so as to suppress the evolution of hydrogen sulfide from the bed while minimizing the formation of aerobic biological sludge which would plug the bed(s). This controlled biological activity that occurs in the carbon adsorption system provides for a substantial increase in the effective organic contaminant removal capacity of the activated carbon.
    Type: Grant
    Filed: January 20, 1975
    Date of Patent: October 11, 1977
    Assignee: Exxon Research & Engineering Co.
    Inventors: Ronald V. Trense, Allen Clamen, John M. Fernbacher
  • Patent number: 4048251
    Abstract: Acyclic and alicyclic aliphatic hydrocarbons are isomerized to form a product of enhanced octane by contacting same, in a reaction zone and in the presence of hydrogen, with a catalyst comprising a difficultly reducible metal halide in combination with at least a molar equivalent of hydrogen halide, said reaction zone comprising at least one temperature zone, the temperature in at least one zone being controlled by using said hydrogen halide as an autorefrigerant. In a preferred embodiment, at least a portion of the autorefrigerant evolved from the reaction zone is condensed and used to extract at least a portion of the metal halide component of the catalyst from at least a portion of the hydrocarbon product. A preferred catalyst is tantalum pentafluoride, niobium pentafluoride or their mixtures in combination with at least a five-fold molar excess of hydrogen fluoride.
    Type: Grant
    Filed: January 2, 1976
    Date of Patent: September 13, 1977
    Assignee: Exxon Research and Engineering Company
    Inventors: Robert P. Cahn, Michael Siskin
  • Patent number: 4046673
    Abstract: Supported iridium-containing hydrocarbon conversion catalysts which are at least partially deactivated due to the deposition of carbonaceous residues thereon during contact with hydrocarbons are regenerated by contacting the residue-containing catalyst, prior to contact with oxygen at elevated temperature, with a chlorine-containing reagent to increase the catalyst chlorine content to a level in the range of from about 0.7 to 2.0 wt. %, based on anhydrous, carbonaceous residue-free catalyst, and thereafter contacting the catalyst with a substantially sulfur-free gaseous mixture containing oxygen at a temperature varying from about 775.degree. to 900.degree. F. for a time sufficient to burn at least a portion of the carbonaceous residue from the catalyst while maintaining at least 0.7 wt. % chlorine on the catalyst during contact with said gaseous mixture.
    Type: Grant
    Filed: September 15, 1975
    Date of Patent: September 6, 1977
    Assignee: Exxon Research and Engineering Company
    Inventors: John D. Paynter, Beverly B. Fuqua, Richard R. Cecil
  • Patent number: 4043900
    Abstract: Organic sulfur compounds are removed from hydrocarbon feedstocks by contacting said feedstocks with a catalyst system comprising a difficultly reducible metal halide and a hydrogen halide, said contacting being done in the presence of hydrogen. The preferred metal halide is tantalum pentafluoride, niobium pentafluoride or mixtures thereof. The preferred hydrogen halide is hydrogen fluoride.
    Type: Grant
    Filed: November 4, 1975
    Date of Patent: August 23, 1977
    Assignee: Exxon Research and Engineering Company
    Inventor: Michael Siskin