CA1070715A - Process for the hydroalkylation of paraffins - Google Patents

Process for the hydroalkylation of paraffins

Info

Publication number
CA1070715A
CA1070715A CA252,941A CA252941A CA1070715A CA 1070715 A CA1070715 A CA 1070715A CA 252941 A CA252941 A CA 252941A CA 1070715 A CA1070715 A CA 1070715A
Authority
CA
Canada
Prior art keywords
hydrogen
alkylation
halide
catalyst
mixtures
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA252,941A
Other languages
English (en)
French (fr)
Inventor
Michael Siskin
Joseph J. Porcelli
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Exxon Research and Engineering Co filed Critical Exxon Research and Engineering Co
Application granted granted Critical
Publication of CA1070715A publication Critical patent/CA1070715A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/56—Addition to acyclic hydrocarbons
    • C07C2/58—Catalytic processes
    • C07C2/62—Catalytic processes with acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
    • C07C6/10—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond in hydrocarbons containing no six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C07C2527/12—Fluorides
    • C07C2527/1206—Hydrogen fluoride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/133—Compounds comprising a halogen and vanadium, niobium, tantalium, antimonium or bismuth
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/8995—Catalyst and recycle considerations
    • Y10S585/905—Catalyst and recycle considerations by-product conversion to feed

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA252,941A 1975-06-12 1976-05-20 Process for the hydroalkylation of paraffins Expired CA1070715A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/586,176 US4025577A (en) 1975-06-12 1975-06-12 Hydroalkylation of paraffins with olefins utilizing hydrogen fluoride and metal pentafluoride catalyst

Publications (1)

Publication Number Publication Date
CA1070715A true CA1070715A (en) 1980-01-29

Family

ID=24344619

Family Applications (1)

Application Number Title Priority Date Filing Date
CA252,941A Expired CA1070715A (en) 1975-06-12 1976-05-20 Process for the hydroalkylation of paraffins

Country Status (9)

Country Link
US (2) US4025577A (OSRAM)
JP (1) JPS51149205A (OSRAM)
AU (1) AU1425576A (OSRAM)
CA (1) CA1070715A (OSRAM)
DE (1) DE2625919A1 (OSRAM)
FR (1) FR2314162A1 (OSRAM)
GB (1) GB1554229A (OSRAM)
IT (1) IT1195022B (OSRAM)
NL (1) NL7606227A (OSRAM)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4025577A (en) * 1975-06-12 1977-05-24 Exxon Research And Engineering Company Hydroalkylation of paraffins with olefins utilizing hydrogen fluoride and metal pentafluoride catalyst
AU1439476A (en) * 1975-06-13 1977-12-01 Exxon Research Engineering Co Alkylation of light paraffins
US4065381A (en) * 1976-12-29 1977-12-27 Exxon Research And Engineering Company Maintaining effective molar ratio of HF to metal pentafluoride in a hydrocarbon conversion process
US4105704A (en) * 1976-12-29 1978-08-08 Exxon Research & Engineering Co. Method for preparing and using a soluble metal pentafluoride-hydrogen fluoride catalyst
USRE33080E (en) * 1981-08-31 1989-10-03 Exxon Research And Engineering Company Adamantane catalyzed paraffin isomerization
US4467130A (en) * 1981-09-01 1984-08-21 Olah George A Condensation of natural gas or methane into gasoline-range hydrocarbons
US4465893A (en) * 1982-08-25 1984-08-14 Olah George A Oxidative condensation of natural gas or methane into gasoline range hydrocarbons
US4513164A (en) * 1981-09-01 1985-04-23 Olah George A Condensation of natural gas or methane into gasoline range hydrocarbons
US4472268A (en) * 1983-01-18 1984-09-18 El Paso Products Company Upgrading of natural gasoline with trifluoromethane sulfonic acid, hydrofluoric acid and Lewis acid catalyst
US4582571A (en) * 1984-07-20 1986-04-15 Ashland Oil, Inc. Separation of tantalum or antimony pentafluoride from isobutyryl fluoride and anhydrous hydrogen fluoride
AU626091B2 (en) * 1988-07-15 1992-07-23 Mobil Oil Corporation Heterogeneous isoparaffin/olefin alkylation process
US5238961A (en) * 1990-06-14 1993-08-24 Allergan, Inc. Pgf 1-alcohols and their use as ocular hypotensives
EP0796657B1 (en) 1991-06-21 2002-01-16 Phillips Petroleum Company Alkylation catalyst containing hydrofluoric acid and a sulfone
US5220096A (en) * 1991-06-21 1993-06-15 Mobil Oil Corporation Liquid acid alkylation catalyst composition and isoparaffin:olefin alkylation process
US5569807A (en) * 1992-05-01 1996-10-29 Phillips Petroleum Company Isoparaffin-olefin alkylation
US5534657A (en) * 1991-06-21 1996-07-09 Phillips Petroleum Company Isoparaffin-olefin alkylation
US5196628A (en) * 1991-06-21 1993-03-23 Mobil Oil Corporation Liquid acid alkylation catalyst and isoparaffin:olefin alkylation process
AU2679092A (en) * 1991-09-25 1993-04-27 Mobil Oil Corporation Improved liquid acid alkylation catalyst and isoparaffin:olefin alkylation process
US5382746A (en) * 1992-02-11 1995-01-17 Mobil Oil Corporation Removal of light ASO in HF alkylation process
US5191150A (en) * 1992-02-11 1993-03-02 Mobil Oil Corporation Method for separating conjunct polymeric byproducts from mixture containing hydrofluoric acid and a sulfone
US5414186A (en) * 1992-08-05 1995-05-09 Mobil Oil Corporation Liquid acid alkylation catalyst and isoparaffin-olefin alkylation process
US5304522A (en) * 1993-06-01 1994-04-19 Mobil Oil Corporation Liquid acid regeneration method
US6265630B1 (en) * 1998-12-30 2001-07-24 Phillips Petroleum Company Process for pentane disproportionation
US20040010175A1 (en) * 2002-07-11 2004-01-15 Randolph Bruce B. Catalyst and process for contacting a hydrocarbon and ethylene
EP2014641A3 (en) * 2007-06-06 2009-03-18 Huntsman International Llc Process for preparing mixtures of diphenylmethane diisocyanates and polyphenyl polymethylene polyisocyanates
US8704018B2 (en) * 2012-07-31 2014-04-22 Chevron U.S.A. Inc. Extracted conjunct polymer naphtha
US9567534B2 (en) 2014-04-21 2017-02-14 Uop Llc Flexible gasoline process using multiple feedstocks
US11149214B2 (en) * 2018-12-17 2021-10-19 Saudi Arabian Oil Company Method and process to maximize diesel yield

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR823592A (fr) * 1937-06-25 1938-01-22 Universal Oil Prod Co Procédé d'alkylation des hydrocarbures paraffiniques
GB498260A (en) * 1937-11-09 1939-01-05 Universal Oil Prod Co Process for the production of alkylated hydrocarbons
US2355339A (en) * 1939-03-21 1944-08-08 Texas Co Manufacture of motor fuels
US2360444A (en) * 1942-12-10 1944-10-17 Pollock Leo Electric socket
US2406954A (en) * 1943-09-20 1946-09-03 Universal Oil Prod Co Alkylation of isoparaffinic hydrocarbons
US3201494A (en) * 1962-08-27 1965-08-17 Shell Oil Co Hexafluoroantimonic acid-catalyzed hydrocarbon conversions
US3678120A (en) * 1970-01-29 1972-07-18 Universal Oil Prod Co Hydrocarbon conversion catalyst and process
US3903196A (en) * 1972-07-03 1975-09-02 Chevron Res Isomerization
US3819743A (en) * 1972-12-15 1974-06-25 Standard Oil Co Alkylation of heptanes with isobutane using antimony pentafluoride-fluorosulfonic acid mixtures
US3809728A (en) * 1973-01-19 1974-05-07 Chevron Res Catalyst rejuvenation
US3979476A (en) * 1973-01-19 1976-09-07 Chevron Research Company Hydrocarbon conversion catalyst and process
US3852371A (en) * 1973-04-11 1974-12-03 Chevron Res Isoparaffin-olefin alkylation with a supported hf antimony pentafluoride catalyst
US4025577A (en) * 1975-06-12 1977-05-24 Exxon Research And Engineering Company Hydroalkylation of paraffins with olefins utilizing hydrogen fluoride and metal pentafluoride catalyst

Also Published As

Publication number Publication date
US4064189A (en) 1977-12-20
DE2625919A1 (de) 1976-12-23
NL7606227A (nl) 1976-12-14
AU1425576A (en) 1977-12-01
FR2314162A1 (fr) 1977-01-07
US4025577A (en) 1977-05-24
FR2314162B1 (OSRAM) 1981-03-20
JPS51149205A (en) 1976-12-22
GB1554229A (en) 1979-10-17
IT1195022B (it) 1988-09-28

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