By Dehydrogenation Patents (Class 585/654)
  • Patent number: 4476339
    Abstract: Steam dehydrocyclization of paraffinic hydrocarbons to aromatic hydrocarbons is effected in the presence of supported catalyst, typically bearing rhodium and preferably chromium and potassium, and characterized by a pH less than about 8.
    Type: Grant
    Filed: February 5, 1981
    Date of Patent: October 9, 1984
    Assignee: Texaco Inc.
    Inventors: Russell R. Reinhard, Tansukhial G. Dorawala, Edwin R. Kerr
  • Patent number: 4451686
    Abstract: Catalytic dehydrogenation of alkyl- or dialkyl- aromatic hydrocarbons such as ethylbenzene or ethyltoluene to vinyl aromatic hydrocarbons is achieved by passing the aromatic hydrocarbons on a crystalline silica which has been calcined under an inert atmosphere and which contains from about 0.05 to about 1 weight percent of an alkali metal oxide such as sodium oxide. In the preparation of the crystalline silica, limited washing of the crystalline silica precursor is performed to obtain an amount of alkali metal oxide remaining in the crystalline silica between about 0.05 and about 1 weight %.
    Type: Grant
    Filed: May 9, 1983
    Date of Patent: May 29, 1984
    Assignee: Cosden Technology, Inc.
    Inventors: Georges E. M. J. De Clippeleir, Raymond M. Cahen, Francisco A. Martins Mendes Cerejo
  • Patent number: 4444984
    Abstract: A method for synthesizing hydrocarbons from a methane source which comprises contacting methane with an oxide of tin at a temperature of about 500.degree. to 1000.degree. C. The oxide is reduced by the contact and coproduct water is formed. A reducible oxide of tin is regenerated by oxidizing the reduced composition with molecular oxygen. The oxide SnO.sub.2 is a particularly effective synthesizing agent.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: April 24, 1984
    Assignee: Atlantic Richfield Company
    Inventors: C. Andrew Jones, John J. Leonard, John A. Sofranko
  • Patent number: 4443646
    Abstract: A method for synthesizing hydrocarbons from a methane source which comprises contacting methane with an oxide of bismuth at a temperature of about 500.degree. to 850.degree. C. The oxide is reduced by the contact and coproduct water is formed. A reducible oxide of bismuth is regenerated by oxidizing the reduced composition with molecular oxygen. The oxide Bi.sub.2 O.sub.3 is a particularly effective solid synthesizing agent.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: April 17, 1984
    Assignee: Atlantic Richfield Company
    Inventors: C. Andrew Jones, John J. Leonard, John A. Sofranko
  • Patent number: 4443645
    Abstract: A method for synthesizing hydrocarbons from a methane source which comprises contacting methane with an oxide of germanium at a temperature of 500.degree. to 800.degree. C. The oxide is reduced by the contact and coproduct water is formed. A reducible oxide of germanium is regenerated by oxidizing the reduced composition with molecular oxygen. The oxide GeO.sub.2 is a particularly effective synthesizing agent.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: April 17, 1984
    Assignee: Atlantic Richfield Company
    Inventors: C. Andrew Jones, John J. Leonard, John A. Sofranko
  • Patent number: 4443644
    Abstract: A method for synthesizing hydrocarbons from a methane source which comprises contacting methane with an oxide of antimony at a temperature of about 500.degree. to 1000.degree. C. The oxide is reduced by the contact and coproduct water is formed. A reducible oxide of antimony is regenerated by oxidizing the reduced composition with molecular oxygen. The oxide Sb.sub.2 O.sub.3 is a particularly effective synthesizing agent.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: April 17, 1984
    Assignee: Atlantic Richfield Company
    Inventors: C. Andrew Jones, John J. Leonard, John A. Sofranko
  • Patent number: 4443649
    Abstract: A method for synthesizing hydrocarbons from a methane source which comprises contacting methane with an oxide of manganese at a temperature of about 500.degree. to 1000.degree. C. The oxide is reduced by the contact and coproduct water is formed. A reducible oxide of manganese is regenerated by oxidizing the reduced composition with molecular oxygen. The oxide Mn.sub.3 O.sub.4 is a particularly effective synthesizing agent.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: April 17, 1984
    Assignee: Atlantic Richfield Company
    Inventors: C. Andrew Jones, John J. Leonard, John A. Sofranko
  • Patent number: 4443647
    Abstract: A method for synthesizing hydrocarbons from a methane source which comprises contacting methane with an oxide of lead at a temperature of about 500.degree. to 1000.degree. C. The oxide is reduced by the contact and coproduct water is formed. A reducible oxide of lead is regenerated by oxidizing the reduced composition with molecular oxygen. The oxide PbO is a particularly effective synthesizing agent.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: April 17, 1984
    Assignee: Atlantic Richfield Company
    Inventors: C. Andrew Jones, John J. Leonard, John A. Sofranko
  • Patent number: 4443648
    Abstract: A method for synthesizing hydrocarbons from a methane source which comprises contacting methane with an oxide of indium at a temperature of about 500.degree. to 850.degree. C. The oxide is reduced by the contact and coproduct water is formed. A reducible oxide of indium is regenerated by oxidizing the reduced composition with molecular oxygen. The oxide In.sub.2 O.sub.3 is a particularly effective solid synthesizing agent.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: April 17, 1984
    Assignee: Atlantic Richfield Company
    Inventors: C. Andrew Jones, John J. Leonard, John A. Sofranko
  • Patent number: 4435607
    Abstract: Dehydrogenatable hydrocarbons may be subjected to a dehydrogenation reaction in which the hydrocarbons are treated with a dehydrogenation catalyst such as a modified iron compound in the presence of steam in a multi-catalyst bed system. The reaction mixture containing unconverted hydrocarbon, dehydrogenated hydrocarbon, hydrogen and steam is then contacted with a selective oxidation catalyst such as a noble metal of Group VIII of the Periodic Table, a metal of Group IVA of the Periodic Table and, if so desired, a metal of Group IA or IIA of the Periodic Table composited on a highly porous inorganic support. The oxidation catalyst will selectively oxidize the hydrogen to improve the combustion thereof and supply the necessary heat required for a subsequent dehydrogenation treatment.
    Type: Grant
    Filed: September 22, 1982
    Date of Patent: March 6, 1984
    Assignee: UOP Inc.
    Inventor: Tamotsu Imai
  • Patent number: 4423251
    Abstract: A hydrocarbon conversion process is disclosed which may be used to produce high purity isobutylene and/or tertiary butyl alcohol and methyl tertiary butyl ether. A mixed C.sub.4 feed stream is divided into two portions with a first portion being passed through a hydration zone to produce the tertiary butyl alcohol. The remaining hydrocarbons withdrawn from the hydration zone and the second portion of the feed stream are changed to an etherification zone. The unconverted hydrocarbons exiting the etherification zone may be subjected to isomerization and/or dehydrogenation to produce additional isobutylene. The high purity isobutylene is obtained by dehydrating the tertiary butyl alcohol.
    Type: Grant
    Filed: September 9, 1982
    Date of Patent: December 27, 1983
    Assignee: UOP Inc.
    Inventors: Peter R. Pujado, Bipin V. Vora
  • Patent number: 4420649
    Abstract: Dehydrogenatable hydrocarbons are dehydrogenated by contacting them at hydrocarbon dehydrogenation conditions with a multimetallic catalytic composite comprising a combination of a catalytically effective amount of a pyrolyzed ruthenium carbonyl component with a porous carrier material containing a uniform dispersion of catalytically effective amounts of a platinum group component maintained in the elemental metallic state, and of a rhenium component. An optional non-acidic multimetallic catalytic composite disclosed herein is a combination of a catalytically effective amount of a pyrolyzed ruthenium carbonyl component with a porous carrier material containing a uniform dispersion of catalytically effective amounts of a platinum group component which is maintained in the elemental metallic state during the incorporation of the ruthenium carbonyl component, a rhenium component, and an alkali or alkaline earth component.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: December 13, 1983
    Assignee: UOP Inc.
    Inventor: George J. Antos
  • Patent number: 4413147
    Abstract: Isobutane is converted to methacrolein in an integrated two-step process wherein isobutane is dehydrogenated in a first step to isobutylene, hydrogen, and by-products and the reaction effluent is passed directly into a second step where isobutylene is oxidized to methacrolein without significant oxidation of the hydrogen and by-products. The methacrolein and by-products may be separated and the unreacted isobutylene and isobutane recycled to the first step. Alternatively, the effluent from the second step may be used as feed to a further oxidation step for conversion of methacrolein to methacrylic acid. In one embodiment, the hydrogen produced in the first step is oxidized using the excess oxygen from the second step under conditions selected to avoid loss of the C.sub.4 components. In an alternative embodiment, the unreacted isobutane and isobutylene are absorbed and separated from the remaining components before being recycled to the first step.
    Type: Grant
    Filed: April 14, 1982
    Date of Patent: November 1, 1983
    Assignee: The Halcon SD Group, Inc.
    Inventor: Sargis Khoobiar
  • Patent number: 4409417
    Abstract: Isobutane may be dehydrogenated to isobutylene with increased selectivity by passing isobutane together with hydrogen and ammonia at 700.degree. F.-1200.degree. F. in the presence of a supported catalyst containing Group IA metals (Li, K) plus Pt-Re, Pt-Ge, or Pt-Re-Ge.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: October 11, 1983
    Assignee: Texaco Inc.
    Inventor: Sheldon Herbstman
  • Patent number: 4393259
    Abstract: A multi-step hydrocarbon conversion process for producing gasoline from propane or butane is disclosed. The feed hydrocarbon is passed into a dehydrogenation zone and the entire dehydrogenation zone effluent including hydrogen and light by-products is then passed into a catalytic condensation zone wherein the resulting olefins are converted into dimers and trimers. The condensation zone effluent stream is passed into a separation zone in which the dimers and trimers are concentrated into a product stream, with unconverted feed hydrocarbon and hydrogen being recycled to the dehydrogenation zone.
    Type: Grant
    Filed: August 5, 1981
    Date of Patent: July 12, 1983
    Assignee: UOP Inc.
    Inventors: Dennis J. Ward, Bipin V. Vora
  • Patent number: 4392003
    Abstract: This invention relates to a method of dehydroisomerizing n-butane by contacting at elevated temperatures a feedstock containing n-butanes with a catalyst composition containing a gallium compound on a support. The process affords a valuable method of producing iso-butene which is a basic chemical feedstock for a number of products including polyisobutenes, methacrolein and methyl tertiary butyl ether, to name a few. The last named compound can be prepared by reacting isobutene with methanol and is a convenient means of separating iso-butene from the products of the dehydroisomerization stage.
    Type: Grant
    Filed: June 8, 1981
    Date of Patent: July 5, 1983
    Assignee: The British Petroleum Company Limited
    Inventors: Alexander J. Kolombos, Clive D. Telford, Dennis Young
  • Patent number: 4381418
    Abstract: A process for the catalytic dehydrogenation of C.sub.2 + normally gaseous paraffinic hydrocarbons to produce the corresponding monoolefinic hydrocarbons is disclosed. The energy-efficient process is particularly directed to the separation of recycle hydrogen from the olefinic hydrocarbon products and unreacted paraffinic hydrocarbons.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: April 26, 1983
    Assignee: UOP Inc.
    Inventors: Steve A. Gewartowski, Dennis E. O'Brien
  • Patent number: 4381417
    Abstract: A process for the catalytic dehydrogenation of low molecular weight paraffinic hydrocarbons is disclosed. The process is particularly directed to the separation of hydrogen from the olefinic hydrocarbon products and unreacted paraffinic hydrocarbons.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: April 26, 1983
    Assignee: UOP Inc.
    Inventors: Bipin V. Vora, Dennis E. O'Brien, Norman H. Scott
  • Patent number: 4371730
    Abstract: The catalytic dehydrogenation of at least one dehydrogenatable organic compound which has at least one ##STR1## grouping is carried out in the presence of a zinc silicate catalyst and in the substantial absence of free oxygen.
    Type: Grant
    Filed: June 5, 1981
    Date of Patent: February 1, 1983
    Assignee: Phillips Petroleum Company
    Inventor: Alan D. Eastman
  • Patent number: 4329516
    Abstract: A process is described for producing methyl tert.-butyl ether from butane-containing light hydrocarbon mixtures. The n-butane is isomerized to isobutane which is dehydrogenated to an isobutene/isobutane molar ratio of 0.4 to 2:1, the isobutene in the mixture is etherified with methanol to form methyl tert.-butyl ether and the residual isobutane is recycled for dehydrogenation. After the isomerization step, the n-butane and isobutane can be separated and the n-butane recycled. The product containing methyl tert.-butyl ether can be used as a gasoline additive.
    Type: Grant
    Filed: June 3, 1980
    Date of Patent: May 11, 1982
    Assignee: Davy International Aktiengesellschaft
    Inventor: Ghazi R. Al-Muddarris
  • Patent number: 4324937
    Abstract: A hydrocarbon conversion process for the production of motor fuel blending stocks from propane and butane is disclosed. Preferably a charge stream comprising a mixture of C.sub.3 -C.sub.4 saturated hydrocarbons is split into a C.sub.3 stream passed into a dehydrogenation zone and a C.sub.4 stream passed into an isostripper column. Normal butanes are removed from the isostripper and passed into an isomerization zone, with product isobutane being concentrated by fractionation in the isostripper. Isobutane and propylene from the dehydrogenation zone are then reacted in an alkylation zone which produces C.sub.5 -plus product hydrocarbons. The effluent of the alkylation zone enters the isostripper. The product stream and a propane-containing stream are withdrawn from the isostripper, with the propane-containing stream being passed into a second separation zone. Alternative butane fractionation systems are disclosed.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: April 13, 1982
    Assignee: UOP Inc.
    Inventor: Bipin V. Vora
  • Patent number: 4313013
    Abstract: A palladium or palladium alloy hydrogen diffusion membrane which has been treated with silane and/or silicon tetrafluoride is employed to separate hydrogen from a hydrocarbon with which it is in admixture and from which it may have been produced under dehydrogenation conditions in the presence of said membrane.
    Type: Grant
    Filed: August 1, 1980
    Date of Patent: January 26, 1982
    Assignee: Phillips Petroleum Company
    Inventor: Jesse R. Harris
  • Patent number: 4309275
    Abstract: A process for selectively converting adsorbable hydrocarbon feeds containing straight-chain and slightly branched-chain hydrocarbons to olefins by contacting the feeds with crystalline silicates.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: January 5, 1982
    Assignee: Chevron Research Company
    Inventor: Bernard F. Mulaskey
  • Patent number: 4309276
    Abstract: Hydrocarbon conversion in the presence of a low-sodium form crystalline silicate converts normal and slightly branched paraffins, at least in part, to olefins.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: January 5, 1982
    Assignee: Chevron Research Company
    Inventor: Stephen J. Miller
  • Patent number: 4304948
    Abstract: A multi-step hydrocarbon conversion process for producing gasoline from butane is disclosed. Butane is passed into a dehydrogenation zone and the entire dehydrogenation zone effluent is then passed into a catalytic condensation zone wherein butylene is converted into C.sub.8 and C.sub.12 hydrocarbons. The condensation zone effluent, a stripper overhead stream and an absorber bottoms stream are commingled and then separated into vapor and liquid portions. The liquid is passed into the stripper, and the vapor portion is contacted with stripper bottoms liquid in an absorber. The absorber overhead stream is contacted with liquid butane in a second absorber to remove C.sub.8 hydrocarbons and is then recycled to the dehydrogenation zone. Debutanizing a portion of the stripper bottoms yields the liquid butane and a gasoline product.
    Type: Grant
    Filed: June 27, 1980
    Date of Patent: December 8, 1981
    Assignee: UOP Inc.
    Inventors: Bipin V. Vora, Dennis J. Ward
  • Patent number: 4293722
    Abstract: A multi-step hydrocarbon conversion process for producing gasoline from propane is disclosed. Propane is passed into a dehydrogenation zone and the entire dehydrogenation zone effluent is then passed into a catalytic condensation zone wherein propylene is converted into C.sub.6 and C.sub.9 hydrocarbons. The condensation zone effluent, a stripper overhead stream and an absorber bottoms stream are commingled and then separated into vapor and liquid portions. The liquid is passed into the stripper, and the vapor portion is contacted with stripper bottoms liquid in an absorber. The absorber overhead stream is contacted with liquid propane in a second absorber to remove C.sub.6 hydrocarbons and is then recycled to the dehydrogenation zone. Depropanizing a portion of the stripper bottoms yields the liquid propane and a gasoline product.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: October 6, 1981
    Assignee: UOP Inc.
    Inventors: Dennis J. Ward, Bipin V. Vora
  • Patent number: 4235755
    Abstract: Dehydrogenatable hydrocarbons are dehydrogenated by contacting them, at dehydrogenation conditions, with a nonacidic catalytic composite comprising a combination of catalytically effective amounts of a platinum group component, a cobalt component, a lanthanide series component and an alkali or alkaline earth component with a porous carrier material. A specific example of the nonacidic catalytic composite disclosed herein is a combination of a platinum group component, a cobalt component, a lanthanide series component, and an alkali or alkaline earth component with a porous carrier material in amounts sufficient to result in a composite containing about 0.01 to about 2 wt. % platinum group metal, about 0.05 to about 5 wt. % cobalt, about 0.01 to about 5 wt. % lanthanide series metal and about 0.1 to about 5 wt. % alkali metal or alkaline earth metal.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: November 25, 1980
    Assignee: UOP Inc.
    Inventor: George J. Antos
  • Patent number: 4200764
    Abstract: The present invention provides an unsupported catalyst with superior crush strength for use in a vapor phase reaction for the high yield conversion of lower aliphatic hydrocarbons such as n-butane to corresponding monocarboxylic acids used as acetic acid. The catalyst is prepared by the reduction of a vanadium oxide containing chromium catalyst.
    Type: Grant
    Filed: December 12, 1977
    Date of Patent: April 29, 1980
    Assignee: Celanese Corporation
    Inventors: William E. Slinkard, Anthony B. Baylis, Michael P. Hughes