By Double-bond-shift Isomerization Patents (Class 585/664)
  • Patent number: 4593146
    Abstract: Aliphatic olefinic hydrocarbons are isomerized in the presence of a catalyst consisting essentially of elemental chromium or a chromium compound and an aluminum phosphate support wherein the phosphorus/aluminum atomic ratio of the support is less than 1.
    Type: Grant
    Filed: March 29, 1985
    Date of Patent: June 3, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Marvin M. Johnson, Gerhard P. Nowack, Max P. McDaniel
  • Patent number: 4587375
    Abstract: A process for the isomerization of n-butenes, comprising contacting, at elevated temperatures, a feed containing n-butenes with a catalyst comprising a crystalline silica polymorph of the silicalite type in the presence of stream to recover a steam containing isobutene. The reaction can be carried out in either liquid or vapor phase.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: May 6, 1986
    Assignee: Labofina, S.A.
    Inventors: Guy L. G. Debras, Georges E. M. J. De Clippeleir, Raymond M. Cahen
  • Patent number: 4556754
    Abstract: A process for the isomerization of isolated double bonds to conjugated double bonds in low-molecular weight homo- and/or copolymers of 1,3-dienes uses an isomerization catalyst optionally in the presence of a solvent, wherein the isomerization catalyst is a mixture of(a) a hydroxide of the alkali metals potassium, rubidium, or cesium, and an alcohol or(b) a lithium alcoholate or sodium alcoholate and a potassium, rubidium, or cesium salt or(c) sodium hydroxide, an alcohol, and a polar, aprotic compound.The isomerization is conducted at a temperature of 80.degree.-220.degree. C.
    Type: Grant
    Filed: February 18, 1983
    Date of Patent: December 3, 1985
    Assignee: Chemische Werke Huels Aktiengesellschaft
    Inventors: Wolfgang Kampf, Christoph Herrmann
  • Patent number: 4544780
    Abstract: A process for the isomerization of a tertiary double bonded olefin having a hydrogen atom attached to a carbon atom vicinal to the tertiary carbon of the double bond comprises treating the olefin in a solution of dry liquid sulfur dioxide in the presence of a catalyst selected from oxygen, a hydroperoxide or a protic acid or mixtures thereof.
    Type: Grant
    Filed: April 27, 1984
    Date of Patent: October 1, 1985
    Assignee: Shell Oil Company
    Inventor: Stanley E. Wilson
  • Patent number: 4503282
    Abstract: A process to convert a substantially linear alkene, such as n-butene, to isomerized products comprises contacting such alkene under conversion conditions comprising a temperature of above 300.degree. C. to about 650.degree. C. and an alkene reactant partial pressure of less than about 0.4 atmospheres with an AMS-1B borosilicate catalyst composition containing at least 50 wt. % hydrogen from AMS-1B incorporated in an inert binder.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: March 5, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventor: David L. Sikkenga
  • Patent number: 4499325
    Abstract: A process to convert an alkene to oligomerized, aromatized and isomerized products comprises contacting such alkene under conversion conditions with an AMS-1B borosilicate catalyst composition.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: February 12, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventors: Marvin R. Klotz, Edwin F. Peters
  • Patent number: 4499326
    Abstract: A process to convert a normal butene to isomerized products comprises contacting such alkene under conversion conditions with a hydrogen form AMS-1B borosilicate catalyst composition at a conversion temperature below 250.degree. C.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: February 12, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventor: John L. Melquist
  • Patent number: 4451685
    Abstract: A process to convert propylene to gasoline blending stock products comprises contacting C.sub.2 -C.sub.3 olefins under conversion conditions with an AMS-1B crystalline borosilicate catalyst composition.
    Type: Grant
    Filed: April 15, 1983
    Date of Patent: May 29, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventors: Thomas D. Nevitt, Norman F. Jerome
  • Patent number: 4436949
    Abstract: A novel process for the conversion of olefins is provided by adding water to said olefin and thereafter contacting said olefin with an acidic alumina catalyst under conditions sufficient to effect the conversion of said olefin.
    Type: Grant
    Filed: September 21, 1982
    Date of Patent: March 13, 1984
    Assignee: Phillips Petroleum Company
    Inventors: John W. Myers, Daniel J. Strope
  • Patent number: 4435609
    Abstract: Isobutylene containing a minor amount, e.g. 0.06-0.10 wt %, of n-butene-1 is subjected to gas phase isomerization using hydrogen and Group VIII metal catalyst to convert the butene-1 to butene-2 with at least 65% conversion and no more than 0.3% hydrogenation of the isobutylene; butene-2 is more readily separated from the isobutylene by distillation. Isomerization conditions applied are defined by a pressure of 3 to 5 bars gauge, a temperature of from 40.degree. to 50.degree. C., a space velocity of from 150 to 300 vol/vol/hour, a mass velocity of from 1.1 to 1.5 metric tons/m2/hour and a hydrogen/feed volume ratio of not more than 2.5%.
    Type: Grant
    Filed: May 31, 1983
    Date of Patent: March 6, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventor: Wolfgang W. J. Gschwendtner
  • Patent number: 4434310
    Abstract: A process for the isomerization of isolated double bonds to conjugated double bonds in optionally substituted cyclooctadienes using alkali metal or alkaline earth metal amides, if desired in the presence of a solvent, requires that the alkali metal or alkaline earth metal amide be produced with exclusion of moisture and under a protective gas atmosphere in the presence of the cyclooctadiene to be isomerized; and that the isomerization be conducted at temperatures of 70.degree.-200.degree. C.
    Type: Grant
    Filed: January 13, 1983
    Date of Patent: February 28, 1984
    Assignee: Chemische Werke Huels Aktiengesellschaft
    Inventor: Wolfgang Kampf
  • Patent number: 4433190
    Abstract: A process to convert an alkane, such as n-butane, to dehydrogenated and isomerized products comprises contacting such alkane under conversion conditions with an AMS-1B crystalline borosilicate catalyst composition containing an ion or molecule of a catalytically active element, such as a noble metal.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: February 21, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventors: David L. Sikkenga, Thomas D. Nevitt, Norman F. Jerome
  • Patent number: 4433191
    Abstract: A novel process for the efficient, selective and steady conversion of n-alkenes, such as n-butylenes, to their skeletal isomers is disclosed. Catalysts and catalytic conditions are also disclosed.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: February 21, 1984
    Assignee: Engelhard Corporation
    Inventors: Antonio E. Eleazar, Ronald M. Heck, Joseph C. Dettling, Yiu-Kwan Lui
  • Patent number: 4410754
    Abstract: An olefin isomerization process useful in recovering isobutylene from mixed butylene feed streams is disclosed. Preferably, the feed stream is passed through a first reaction zone to convert some butene-1 to butene-2 and then fed to the lower part of a two-part fractionation system. The butene-2-rich bottoms is withdrawn and the overhead vapor is passed through a second reaction zone in admixture with hydrogen before entering the second or upper part of the fractionation system. The bottoms liquid of the upper part of the fractionation system flows into the lower part of the fractionation system. Isobutylene and recycle hydrogen are recovered from the overhead vapor of the upper part of the fractionation system.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: October 18, 1983
    Assignee: UOP Inc.
    Inventor: Steve A. Gewartowski
  • Patent number: 4400571
    Abstract: Hydrocarbons are converted by contacting them at hydrocarbon conversion conditions with a catalyst composite comprising from about 5 weight percent to about 95 weight percent of a silica polymorph consisting of crystalline silica, said silica polymorph after calcination in air at 600.degree. C. for one hour, having a mean refractive index of 1.39.+-.0.01 and a specific gravity at 25.degree. C. of 1.70.+-.0.05 g/cc and at least 5 weight percent to about 95 weight percent Ziegler alumina.
    Type: Grant
    Filed: September 10, 1982
    Date of Patent: August 23, 1983
    Assignee: UOP Inc.
    Inventor: Delmar W. Robinson
  • Patent number: 4396790
    Abstract: A hydrocarbon conversion process for light olefin isomerization is disclosed. The feed stream is admixed with the overhead vapor stream of a fractionation column, which also acts as a feed stream drying column. The resultant admixture flows through an isomerization zone, and the isomerization zone effluent is partially condensed and passed into the overhead receiver of the column. Uncondensed vapor from the overhead receiver is recycled to the isomerization zone as a hydrogen recycle stream and liquid hydrocarbons withdrawn from the receiver are charged to the top of the fractionation column as the feed stream to the column.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: August 2, 1983
    Assignee: UOP Inc.
    Inventor: Dennis J. Ward
  • Patent number: 4328385
    Abstract: Isomerizable hydrocarbons are isomerized using a catalytic composite comprising a combination of a catalytically effective amount of a pyrolyzed rhenium 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 and pyrolysis of the rhenium carbonyl component, of a tin component, and of a halogen component.
    Type: Grant
    Filed: December 3, 1980
    Date of Patent: May 4, 1982
    Assignee: UOP Inc.
    Inventor: George J. Antos
  • Patent number: 4289919
    Abstract: An aliphatic mono-olefin e.g. butene-2 is isomerized in the presence of a catalyst comprising essentially a small amount of a manganese oxide supported on an activated alumina to produce the corresponding terminal olefin selectively.
    Type: Grant
    Filed: September 12, 1980
    Date of Patent: September 15, 1981
    Assignee: Phillips Petroleum Company
    Inventor: John W. Myers
  • Patent number: 4288643
    Abstract: A process for the preparation of 2,3-dimethylbutene-2 is disclosed, which comprises the steps of converting isovaleraldehyde to isopropylacrolein, hydrogenating .alpha.-isopropylacrolein to form 2,3-dimethylbutanol, dehydrating 2,3-dimethylbutanol to form an olefin mixture comprising 2,3-dimethylbutene-1 and 2,3-dimethylbutene-2, and isomerizing the 2,3-dimethylbutene-1 contained in the mixture into 2,3-dimethylbutene-2. The present process is technically simple and inexpensive to utilize, and results in high yields of the desired product.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: September 8, 1981
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Jurgen Weber, Wolfgang Bernhagen, Helmut Springer
  • Patent number: 4287378
    Abstract: A process for the conversion of at least one olefinic organic compound by disproportionation, proportionation, and/or isomerization, in which an olefin conversion catalyst is exposed to electromagnetic radiation prior to and/or during contact of the organic compound with the catalyst. The catalyst may also be pretreated with ethylene, propylene and/or butene during exposure to radiation or the olefinic compound may be pretreated by contact with magnesium oxide while exposing the magnesium oxide to radiation.
    Type: Grant
    Filed: February 11, 1980
    Date of Patent: September 1, 1981
    Assignee: Phillips Petroleum Company
    Inventor: Filippo Pennella
  • Patent number: 4260842
    Abstract: It has been found that catalysts comprising zirconium hydrides, hydride alkyls and dihydrides bonded to metal or metalloid oxides in particular zirconium hydride bonded to silica, when contacted with olefins under mild conditions rapidly cause isomerization to thermodynamic mixtures.
    Type: Grant
    Filed: November 7, 1979
    Date of Patent: April 7, 1981
    Assignee: The Trustees of Princeton University
    Inventors: Jeffrey Schwartz, Michael D. Ward
  • Patent number: 4229610
    Abstract: Aliphatic monoolefins which can be normal or branched are isomerized at temperatures in the approximate range 500.degree.-1200.degree. F. in presence of a high surface area activated alumina containing a relatively low amount of sodium oxide (Na.sub.2 O) to form 1-olefin. Generally, from about 0.13 to about 0.39 milliequivalents of Na.sub.2 O per gram of the activated alumina containing the Na.sub.2 O, supplied by such sodium compounds as are disclosed, the activated alumina having a large surface area, i.e., about 300-400 m.sup.2 per gram, is used as a catalyst for the isomerization of, say, isomeric n-butenes. Generally, the olefin treated will have from 4 to about 20 carbon atoms per molecule.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: October 21, 1980
    Assignee: Phillips Petroleum Company
    Inventors: John W. Myers, Dean P. Montgomery
  • Patent number: 4217244
    Abstract: A magnesium oxide-containing catalyst which has been used to isomerize butene-2 to butene-1 is regenerated at a localized bed temperature to not exceed about 1000.degree. F., preferably not to exceed about 900.degree. F., by steps involving purging the catalyst with an inert gas, then admixing with said gas oxygen or oxygen-containing gas to produce a final mixture to contain not more than about 0.5 volume percent O.sub.2, and passing said mixture through the catalyst, controlling flow of the mixture to maintain the catalyst at a localized temperature not exceeding substantially about 1000.degree. F., preferably not exceeding about 900.degree. F., increasing the O.sub.2 content of the mixture gradually, but not sufficiently to substantially exceed said temperature of about 1000.degree. F., preferably 900.degree. F.
    Type: Grant
    Filed: May 11, 1978
    Date of Patent: August 12, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Dean P. Montgomery
  • Patent number: 4217461
    Abstract: A process for the isomerization of normal olefinic hydrocarbons is disclosed. The feed stream is passed through a first reaction zone and is then cooled sufficiently to cause the condensation of from about 1 to 25 mole percent of the hydrocarbons in the isomerization zone effluent stream. The uncondensed portion of the effluent of the first reaction zone is heated and passed through a second reaction zone which is maintained at a lower temperature than the first reaction zone. The product isomer is recovered from the effluent of the second reaction zone.
    Type: Grant
    Filed: July 26, 1979
    Date of Patent: August 12, 1980
    Assignee: UOP Inc.
    Inventor: Dennis J. Ward
  • Patent number: 4209655
    Abstract: Isomerizable hydrocarbons including paraffins, cycloparaffins, olefins and alkyl aromatics are isomerized by contacting the hydrocarbon at isomerization conditions with a catalytic composite comprising a platinum group metal on an alpha-alumina monohydrate support wherein said support is prepared by admixing an alpha-alumina monohydrate with an aqueous ammoniacal solution having a pH of at least about 7.5 to form a stable suspension and commingling said suspension with a salt of a strong acid to form an extrudable paste or dough. Upon extrusion, the extrudate is dried and calcined to form said alumina support.
    Type: Grant
    Filed: May 16, 1979
    Date of Patent: June 24, 1980
    Assignee: UOP Inc.
    Inventors: Roy T. Mitsche, George N. Pope
  • Patent number: 4202996
    Abstract: Isomerizable hydrocarbons including paraffins, cycloparaffins, olefins and alkyl aromatics are isomerized by contacting the hydrocarbon at isomerization conditions with a catalytic composite comprising a combination of a nickel component, a molybdenum component and a platinum component with a zeolitic carrier material wherein said platinum component is present in an amount sufficient to result in the composite containing, on an elemental basis, about 0.2 to about 0.5 percent by weight platinum.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: May 13, 1980
    Assignee: UOP Inc.
    Inventor: Lee Hilfman
  • Patent number: 4190612
    Abstract: Beta pinene is converted to alpha pinene in liquid sulfur dioxide. The process is a regioselective isomerization of organic compounds having a carbon-carbon double bond at a tertiary carbon atom, by sulfur dioxide-induced allylic rearrangement of a hydrogen atom and/or replacement of a proton in the allylic position by a deuteron. The organic compound is contacted with sulfur dioxide at temperatures between about 0.degree. and 70.degree. C. for a time sufficient to effect such isomerization to a more stable isomer; and if deuteration is to take place D.sub.2 O is provided in the solution.
    Type: Grant
    Filed: December 20, 1977
    Date of Patent: February 26, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Divakaran Masilamani, Milorad M. Rogic