By Alkyl Transfer, E.g., Disproportionation, Etc. Patents (Class 585/643)
  • Patent number: 4925822
    Abstract: This invention relates to a catalyst composition prepared by reacting in a hydrocarbon solvent a molybdenum or tungsten halide with siloxyalane selected from [(CH.sub.3 CH.sub.2).sub.2 AlO].sub.2 SiR.sub.2 and (R'.sub.3 SiO).sub.2 AlCH.sub.2 CH.sub.3 wherein R and R' are aryl or C.sub.1 -C.sub.5 alkyl. Preferably the halide is tungsten hexachloride, R is phenyl and R' is ethyl. The instant compositions are particularly useful as olefin disproportionation catalysts.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: May 15, 1990
    Assignee: Shell Oil Company
    Inventors: Lynn H. Slaugh, Thomas H. Johnson, Ronald J. Hoxmeier
  • Patent number: 4895997
    Abstract: The disclosure of the invention relates to a process for double bond isomerization in which the double bond of an alpha olefinic molecule is moved from the alpha position to an internal position of the olefinic molecule. The catalyst utilized for this migration is a catalyst prepared by incorporating palladium into an alumina hydrogel.
    Type: Grant
    Filed: August 31, 1988
    Date of Patent: January 23, 1990
    Assignee: Shell Oil Company
    Inventors: David M. Hamilton, Jr., Richard A. Kemp
  • Patent number: 4880520
    Abstract: Crystalline molecular sieves having three-dimensional microporous framework structures of TiO.sub.2, AlO.sub.2, SiO.sub.2 and PO.sub.2 tetrahedral units are disclosed. These molecular sieves have an empirical chemical composition on an anhydrous basis expressed by the formula:mR: (Ti.sub.w Al.sub.x P.sub.y Si.sub.z)O.sub.2wherein "R" represents at least one organic templating agent present in the intracrystalline pore system; "m" represents the molar amount of "R" present per mole of (Ti.sub.w Al.sub.x P.sub.y Si.sub.z)O.sub.2 ; and "w", "x", "y" and "z" represent the mole fractions of titanium, aluminum, phosphorus and silicon, respectively, present as tetrahedral oxides. Their use as adsorbents, catalysts, etc. is also disclosed.
    Type: Grant
    Filed: October 21, 1988
    Date of Patent: November 14, 1989
    Assignee: UOP
    Inventors: Brent M. T. Lok, Bonita K. Marcus, Edith M. Flanigen
  • Patent number: 4837188
    Abstract: Improved catalytic systems of long active duration, comprising initially (a) a tungsten compound, (b) an organometallic compound and (c) a partially or totally fluorinated organic compound.Process of stabilization of these catalytic systems, comprising dissolving (a) in an organic solvent, contacting (b) with (a), agitation and heating at 0.degree. to 100.degree. C. for 0.5 to 60 minutes, then introduction of (c) into the mixture of (a) and (b).Use of these stabilised catalytic systems for the metathesis of olefins which carry functional groups or do not carry such groups.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: June 6, 1989
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Jean-Paul Laval, Michel Leconte, Jean Ollivier, Emile Perez, Francoise Quignard, Isabelle Rico
  • Patent number: 4818442
    Abstract: A process for the disproportionation of olefins comprising contacting said olefins under suitable reaction conditions with a neutral-carbene complex catalyst and then using anhydrous ammonia to effect separation of the catalyst and the organic products.
    Type: Grant
    Filed: October 9, 1984
    Date of Patent: April 4, 1989
    Assignee: Phillips Petroleum Company
    Inventors: John W. Vanderveen, Dennis S. Banasiak
  • Patent number: 4784746
    Abstract: A crude oil is upgraded by thermal treatment at a temperature of at least 400.degree. C. under at least autogenous pressure and preferably from 100 to 1000 psig for about 20 to 30 minutes in order to increase the proportion of distillable components in the crude. The improvement is attributed to alkylation of lower molecular weight components, especially aromatics, by alkyl groups derived from the high boiling component of the crude. The process reduces the nondistillable residue and enables subsequent processing to be carried out with lower gas and coke make. The process may be operated with a whole crude or a topped crude as feed.
    Type: Grant
    Filed: April 22, 1987
    Date of Patent: November 15, 1988
    Assignee: Mobil Oil Corp.
    Inventors: Malvina Farcasiu, Rene B. LaPierre
  • Patent number: 4777310
    Abstract: A method for the selective gas-phase equilibration of at least one C.sub.3 or greater monoalkene over a HAMS-1B crystalline borosilicate-based catalyst composition employing operating conditions in which the total butylene and t-amylene C.sub.5 and lower fraction of the product are maximized and the formation of C.sub.1 to C.sub.3 hydrocarbons, total aromatics and total paraffins are minimized. In another aspect of the invention the equilibration product is usefully separated by converting the isobutylene and t-amylene fractions to their methyl ethers by reaction with methanol.
    Type: Grant
    Filed: December 30, 1987
    Date of Patent: October 11, 1988
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Chander Balakrishnan
  • Patent number: 4754099
    Abstract: This invention relates to a process for disproportionation of hydrocarbon olefins by contacting said hydrocarbon at disproportionation conditions with a catalyst prepared by incorporating a metals solution containing cobalt and an element selected from the group consisting of molybdenum and tungsten into an alumina hydrogel. The final calcined catalysts have surface areas greater than about 300 m.sup.2 /g and more than about 40% of their pore volume in pores having diameters less than about 50 .ANG..
    Type: Grant
    Filed: May 27, 1987
    Date of Patent: June 28, 1988
    Assignee: Shell Oil Company
    Inventors: Richard A. Kemp, David M. Hamilton, Jr.
  • Patent number: 4754098
    Abstract: Catalyst composition is provided which is prepared by impregnating high surface area, high pore volume alumina with at least one magnesium compound convertible to the oxide, and, optionally, at least one alkali metal compound which is convertible to the oxide, and/or at least one zirconium compound convertible to the oxide, then subjecting the impregnated support to an oxygen-containing atmosphere under conditions suitable to convert at least a portion of the magnesium, alkali metal and zirconium compounds to the oxide form. The resulting catalyst is an effective double bond isomerization catalyst, and also greatly enhances the disproportionation activity of disproportionation catalysts when used in combination therewith.
    Type: Grant
    Filed: March 30, 1987
    Date of Patent: June 28, 1988
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4727215
    Abstract: Compounds of the formula:M(NR.sup.1)(OR.sup.2).sub.2 (CHR.sup.3)whereinM is molybdenum or tungsten;R.sup.1 and R.sup.2 are alkyl, aryl, aralkyl or halogen-substituted derivatives or silicon-containing analogs thereof;R.sup.3 is an alkyl, aryl, aralkyl or any substituent that results from the initial reaction between the M.dbd.CHR.sup.3 complex and the olefin(s) that is(are) being metathesized;alkyl has 1-20 carbons, aryl has 6-20 carbons and aralkyl has 7-20 carbons.These compounds are catalysts for the metathesis of ordinary olefins (hydrocarbons) and especially functionalized olefins in the homogeneous phase.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: February 23, 1988
    Assignee: Massachusetts Institute of Technology
    Inventor: Richard R. Schrock
  • Patent number: 4709115
    Abstract: A catalytic process for the disproportionation of alkenes in a distillation column reactor, whereby high conversion and selectivity are simultaneously achieved.
    Type: Grant
    Filed: October 9, 1986
    Date of Patent: November 24, 1987
    Assignee: The Dow Chemical Company
    Inventors: Chu W. Jung, Philip E. Garrou, Gary R. Strickler
  • Patent number: 4676885
    Abstract: The invention disclosed herein comprises a process for the selective upgrading of combustion quality of a distillate transportation fuel by careful selective dehydrogenation, disproportionation and hydrogenation to convert cycloparaffinic materials contained in the distillate transportation fuel to acyclic paraffinic hydrocarbons, wherein said conversion is undertaken by first forming cyclomonoolefinic hydrocarbons from cycloparaffinic hydrocarbons via dehydrogenation, disproportionating the cyclomonoolefinic hydrocarbons to acyclic di-.alpha.-olefin hydrocarbons and then selectively hydrogenating said di-.alpha.-olefin hydrocarbons in the presence of hydrogen to saturate the double bonds of the di-.alpha.-olefin to form acyclic paraffinic hydrocarbons. The selective disproportionation reaction includes the addition of ethylene or an ethylene acting material to ring open the cyclomonoolefinic material.
    Type: Grant
    Filed: May 28, 1986
    Date of Patent: June 30, 1987
    Assignee: Shell Oil Company
    Inventor: Warren V. Bush
  • Patent number: 4654462
    Abstract: Improved process of metathesis of olefins by contact of one or more olefins with a catalyst comprising a tungsten complex with two phenoxy groups, carrying substituents and four other ligands, the complex carrying as coordination groups a halogen atom, an alkyl radical and a carbene. The catalyst preferably is of the formula ##STR1## where X is halogen, R is hydrocarbon or an electronegative group or atom, R.sup.1 is alkyl and R.sup.2 and R.sup.3 are individually hydrogen or alkyl groups.
    Type: Grant
    Filed: February 6, 1986
    Date of Patent: March 31, 1987
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Jean M. Basset, Michel Leconte, Jean Ollivier, Francoise Quignard
  • Patent number: 4613721
    Abstract: The process for the interconversion of "small olefins" selected from the class consisting of ethylene, propylene, butenes and mixtures thereof comprising contacting said small olefin(s) with non-zeolitic molecular sieves.
    Type: Grant
    Filed: May 6, 1985
    Date of Patent: September 23, 1986
    Assignee: Union Carbide Corporation
    Inventor: Steven W. Kaiser
  • Patent number: 4609769
    Abstract: Olefins are converted into other olefins having different numbers of carbon atoms by contact with a catalyst comprising a silica support containing tungsten oxide and a promoting amount of at least one titaniferous agent and activated under conditions suitable for the titaniferous agent to promote the activity of tungsten oxide and silica for the disproportionation and isomerization reaction.
    Type: Grant
    Filed: February 15, 1984
    Date of Patent: September 2, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Simon Kukes, Robert L. Banks
  • Patent number: 4605810
    Abstract: Process for activation of tungsten on silica disproportionation catalyst by contacting the catalyst with at least one acetylenic compound is disclosed. In a specific embodiment, the acetylenic compound can be prepared by isomerization of an allene compound when contacted with magnesium oxide, either as a separate catalyst bed, or as part of the disproportionation catalyst system.
    Type: Grant
    Filed: August 9, 1985
    Date of Patent: August 12, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Robert L. Banks
  • Patent number: 4556753
    Abstract: A process for producing isobutene, comprising contacting, at elevated temperatures, a feed containing propylene with a catalyst comprising a crystalline silica polymorph of the silicalite type in the presence of steam to recover a stream containing isobutene. The reaction can be carried out in either liquid or vapor phase.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: December 3, 1985
    Assignee: Labofina, S.A.
    Inventors: Guy L. G. Debras, Georges E. M. J. De Clippeleir, Raymond M. Cahen
  • Patent number: 4550216
    Abstract: Improved catalyst for the metathesis of olefins comprising a compound of W with a halogen and with a phenoxy group which can carry substituents. It contains 4 halogen atoms and 2 phenoxy groups per atom of W. Preferably, the phenoxy group is halogenated. This catalyst allows the more rapid carrying out of various types of metathesis reactions, when it is used as a co-catalyst in conjunction with organo-metallic compounds, particularly Al or Sn. Among others, it allows the economical preparation of pheromones. It is practically insensitive to traces of water and oxygen.
    Type: Grant
    Filed: June 15, 1984
    Date of Patent: October 29, 1985
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Jean M. M. Basset, Michel Leconte, Jean Ollivier, Francoise Quignard
  • Patent number: 4527001
    Abstract: The process for the interconversion of "small olefins" selected from the class consisting of ethylene, propylene, butenes and mixtures thereof comprising contacting said small olefin(s) with non-zeolitic molecular sieves.
    Type: Grant
    Filed: November 15, 1983
    Date of Patent: July 2, 1985
    Assignee: Union Carbide Corporation
    Inventor: Steven W. Kaiser
  • Patent number: 4517401
    Abstract: Olefins are converted into other olefins having different numbers of carbon atoms by contact with a catalyst comprising an inorganic refractory oxide support containing at least one of tungsten oxide and molybdenum oxide and a promoting amount of at least one methylating agent under conditions suitable for the methylating agent compounds to promote the activity of tungsten and molybdenum oxides for the disproportionation reaction.
    Type: Grant
    Filed: July 26, 1983
    Date of Patent: May 14, 1985
    Assignee: Phillips Petroleum Co.
    Inventors: Simon G. Kukes, Robert L. Banks
  • Patent number: 4504694
    Abstract: Olefins are converted into other olefins having different numbers of carbon atoms by contact with a catalyst comprising an inorganic refractory material containing at least one of tungsten oxide and molybdenum oxide and a promoting amount of at least one treating agent selected from chlorinated silicon compounds, thionyl chloride, and sulfuryl chloride under conditions suitable for the treating agent to promote the activity of tungsten and molybdenum oxides for the disproportionation reaction.
    Type: Grant
    Filed: September 28, 1983
    Date of Patent: March 12, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Simon G. Kukes, Robert L. Banks
  • Patent number: 4499328
    Abstract: Olefins are converted into other olefins having different numbers of carbon atoms by contact with a catalyst comprising silica containing tungsten oxide and a promoting amount of silver under conditions suitable for silver to promote the activity of tungsten oxide for the disproportionation reaction.
    Type: Grant
    Filed: October 5, 1983
    Date of Patent: February 12, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Simon G. Kukes, Robert L. Banks
  • Patent number: 4490478
    Abstract: An improved olefin disproportionation catalyst produced by contacting an inorganic refractory oxide containing a catalytic amount of tungsten oxide or molybdenum oxide with a promoting amount of at least one elemental metal selected from zinc and manganese.
    Type: Grant
    Filed: July 29, 1983
    Date of Patent: December 25, 1984
    Assignee: Phillips Petroleum Company
    Inventors: Robert L. Banks, Simon G. Kukes
  • 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: 4435606
    Abstract: Internal olefins are subjected to metathesis closely coupled after an isomerization reaction to obtain desired molecular weight range linear olefins. Specific process steps and separation conditions are necessary to obtain the desired linear olefins.
    Type: Grant
    Filed: December 24, 1981
    Date of Patent: March 6, 1984
    Assignee: Conoco Inc.
    Inventors: Kaye L. Motz, Paul H. Washecheck, Ronald L. Poe, James E. Yates
  • Patent number: 4420646
    Abstract: Novel feedstocks for the production of synthetic lubricant base oils are described. The feedstock is a blend of internal and alpha olefins with the internal olefins comprising more than 50 but less than 99 weight percent of the blend. The alpha olefins may be derived from ethylene polymerization or wax pyrolysis. The olefins may be oligomerized over a boron trifluoride catalyst and a promoter. When the oligomers are hydrogenated they provide a synthetic lubricant base stock having excellent properties.
    Type: Grant
    Filed: April 28, 1982
    Date of Patent: December 13, 1983
    Assignee: Texaco Inc.
    Inventors: Jerome W. Darden, Lewis W. Watts, Jr., Edward T. Marquis
  • Patent number: 4420647
    Abstract: A synthetic lubricating oil composition comprising a major portion of a synthetic lubricant component or a mixture of a synthetic lubricant component and a hydrocarbon mineral base oil and a minor portion of various additive components is described. The synthetic lubricant component is manufactured from internal olefins.The process for making the synthetic lubricant component utilizes boron trifluoride catalysis with a promoter to produce oligomer mixtures that have surprisingly low viscosities at low temperatures and surprisingly high viscosity indexes as compared with the oligomers found in other methods. It is important that internal olefins be used predominantly to make the oligomers. Alpha olefins make up the balance of the olefins.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: December 13, 1983
    Assignee: Texaco Inc.
    Inventors: Kenneth G. Hammond, Joseph C. Sendra, Lewis W. Watts, Jr., Edward T. Marquis, John M. Larkin
  • Patent number: 4368345
    Abstract: The present invention relates to a process for the disproportionation of n-olefins comprising contacting the olefin feed with a catalyst composition comprising molybdenum oxide or tungsten oxide supported on silica. The catalyst composition is produced by impregnating a silica support with an alcoholic solution of a halide of a metal selected from molybdenum and tungsten, removing the alcoholic solvent by evaporation, and heat treating the impregnated support at an elevated temperature such that (a) the metal halide is converted to the corresponding oxide and/or an oxy-salt and (b) the halogen content thereof is reduced to less than 0.1% by weight of the total composition. By using a catalyst produced by this method, it is possible to carry out the process so as to selectively produce linear higher olefins.
    Type: Grant
    Filed: December 22, 1981
    Date of Patent: January 11, 1983
    Assignee: BP Chemicals Limited
    Inventor: Kathleen F. Dickinson
  • Patent number: 4367352
    Abstract: A process is disclosed for the production of high quality synthetic lubricants which comprises transforming ethylene into a mix of alpha olefins, separating from this mix of alpha olefins the alpha olefins in the range from about 14 to 20 carbon atoms, oligomerizing the alpha olefins in the range from about 14 to 20 atoms with a perfluorosulfonic acid resin catalyst and hydrogenating these oligomerized olefins. The olefins from the original mix of alpha olefins which are lighter and heavier than the 14 to 20 carbon atom alpha olefins processed above are combined and subjected to an isomerization/disproportionation process and the resulting olefins in the range of about 14 to 20 carbon atoms are oligomerized with perfluorosulfonic acid resin catalyst as above. Optionally, these olefins in the range of 14 to 20 carbon atoms may be combined with the olefins prepared directly from ethylene before oligomerization takes place. The resulting oligomers are hydrogenated.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: January 4, 1983
    Assignee: Texaco Inc.
    Inventors: Lewis W. Watts, Jr., Edward T. Marquis
  • 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: 4262156
    Abstract: A process and a catalyst for the disproportionation of olefins is disclosed wherein the catalyst consists essentially of (1) at least one neutral tungsten carbene complex, (2) at least one halogenated promoter, and (3) at least one tin promoter.
    Type: Grant
    Filed: February 6, 1980
    Date of Patent: April 14, 1981
    Assignee: Phillips Petroleum Co.
    Inventor: Dennis S. Banasiak
  • Patent number: 4188501
    Abstract: Purity of hydrocarbon streams is increased by contacting with stable oxides of calcium, titanium, zinc, or zirconium prior to passage to a catalytic conversion process. In one embodiment, the stable metal oxides are preactivated by heating with vaporous hydrocarbon at an elevated temperature which is effective in extending the temperature at which metal oxides are subsequently effective for purification of hydrocarbon streams.
    Type: Grant
    Filed: August 25, 1978
    Date of Patent: February 12, 1980
    Assignee: Phillips Petroleum Company
    Inventors: Mark R. Rycheck, Filippo Pennella