GB1046099A - Continuous process for alkylating an aromatic hydrocarbon - Google Patents

Continuous process for alkylating an aromatic hydrocarbon

Info

Publication number
GB1046099A
GB1046099A GB27261/64A GB2726164A GB1046099A GB 1046099 A GB1046099 A GB 1046099A GB 27261/64 A GB27261/64 A GB 27261/64A GB 2726164 A GB2726164 A GB 2726164A GB 1046099 A GB1046099 A GB 1046099A
Authority
GB
United Kingdom
Prior art keywords
zone
red oil
paraffin
aromatic hydrocarbon
feed
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
GB27261/64A
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.)
Chevron USA Inc
Original Assignee
Chevron Research and Technology Co
Chevron Research 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 Chevron Research and Technology Co, Chevron Research Co filed Critical Chevron Research and Technology Co
Publication of GB1046099A publication Critical patent/GB1046099A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02Monocyclic hydrocarbons
    • C07C15/107Monocyclic hydrocarbons having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/86Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/861Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00Chemistry of hydrocarbon compounds
    • Y10S585/8995Catalyst and recycle considerations
    • Y10S585/901Catalyst and recycle considerations with recycle, rehabilitation, or preservation of solvent, diluent, or mass action agent
    • Y10S585/902Recycle of solvent and catalyst
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00Chemistry of hydrocarbon compounds
    • Y10S585/8995Catalyst and recycle considerations
    • Y10S585/904Catalyst rehabilitation by reversion from different compound
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00Chemistry of hydrocarbon compounds
    • Y10S585/8995Catalyst and recycle considerations
    • Y10S585/905Catalyst and recycle considerations by-product conversion to feed

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Detergent alkylate is obtained by contacting an excess of aromatic hydrocarbon with a C9-C18 alkyl chloride in a first zone in the presence of a red oil complex catalyst to effect condensation of a major proportion of the alkyl chloride, separating red oil from the effluent and contacting the remainder in a second zone with aluminium to complete condensation, separating red oil from the effluent for use as catalyst in the first zone and recovering alkylate from the remainder. In a preferred embodiment partially chlorinated n-paraffin containing 10-50% mol. of alkyl chloride together wit fresh feed n-paraffin boiling in the range 300-605 DEG F. and 2-25 mols. of aromatic hydrocarbon per mol. of chloride are contacted with red oil complex forming 5-25% by volume of the reaction mixture are contacted in the first zone at 100-185 DEG F. for 3-15 minutes to condense 90-95% of the alkyl chloride. Part of the red oil complex is recycled and an amount equivalent to that from the second zone is discarded. Hydrogen chloride may also be separated and washed with the n-paraffin feed to recover organic compounds. Consumption of aluminium in the second zone is regulated either by using a zone packed with metal and limiting the amount of hydrogen chloride introduced, e.g. 1-30 parts per 1000 parts of feed or a saturated solution, or by feeding aluminium at a controlled rate of 0.03-0.1 gram atom per gram atom of chlorine in the chlorinated paraffin feed to the first zone. Red oil may be maintained in an amount of 5-25% vol. of the reaction mixture. Reaction is effected at 100-185 DEG F. for 0.3-15 minutes. Red oil is separated and passed to the first reactor and/or recycled to the second. The product is separated into aromatic hydrocarbon for recycle, n-paraffin which is partially chlorinated and passed to the first zone and alkylate boiling in the range 520-730 DEG F.
GB27261/64A 1963-07-03 1964-07-01 Continuous process for alkylating an aromatic hydrocarbon Expired GB1046099A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US292578A US3355508A (en) 1963-07-03 1963-07-03 Continuous process for alkylating an aromatic hydrocarbon

Publications (1)

Publication Number Publication Date
GB1046099A true GB1046099A (en) 1966-10-19

Family

ID=23125280

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27261/64A Expired GB1046099A (en) 1963-07-03 1964-07-01 Continuous process for alkylating an aromatic hydrocarbon

Country Status (3)

Country Link
US (1) US3355508A (en)
DE (1) DE1443648B2 (en)
GB (1) GB1046099A (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1093994A (en) * 1966-07-12 1967-12-06 Shell Int Research A process for preparing detergent alkylate
US3538177A (en) * 1968-09-25 1970-11-03 Continental Oil Co Preparation of high molecular weight dialkyl aromatic compounds
US3494971A (en) * 1969-04-18 1970-02-10 Universal Oil Prod Co Process for the production of a monoalkylated aromatic hydrocarbon
US3671601A (en) * 1970-09-03 1972-06-20 Continental Oil Co Process for the purification of alkylate
US3674885A (en) * 1970-10-09 1972-07-04 Atlantic Richfield Co Alkylation of benzene utilizing fischer-tropsch olefin-paraffin mixtures
IT946067B (en) * 1971-11-17 1973-05-21 Sir Soc Italiana Resine Spa IMPROVEMENTS IN THE ALKYLATION PROCEDURES
US20030105352A1 (en) * 2001-08-03 2003-06-05 Dado Gregory P. Arylalkylsulfonic acids and methods for producing same

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1995827A (en) * 1933-08-28 1935-03-26 Sharples Solvents Corp Production of alkyl substituted aryl hydrocarbons
US2057306A (en) * 1934-04-24 1936-10-13 Martin Friedrich Aluminum catalyst
US2078238A (en) * 1935-05-07 1937-04-27 Dow Chemical Co Separation of ethylene from its homologues
US2233408A (en) * 1938-03-11 1941-03-04 Nat Aniline & Chem Co Inc Method of producing higher alkyl aromatic sulphonates
US2244512A (en) * 1939-03-04 1941-06-03 Preparation of aliphatic-aromatic
US2388428A (en) * 1943-03-31 1945-11-06 Universal Oil Prod Co Catalysis of organic reactions
US2740807A (en) * 1951-04-09 1956-04-03 Ruhrchemie Ag Preparation of pure white alkyl aryl sulfonates
US3169987A (en) * 1960-12-30 1965-02-16 Universal Oil Prod Co Alkaryl sulfonate production via n-olefin isomerization
US3078322A (en) * 1961-03-08 1963-02-19 Standard Oil Co Hydrogen fluoride alkylation process

Also Published As

Publication number Publication date
DE1443648B2 (en) 1973-08-23
US3355508A (en) 1967-11-28
DE1443648A1 (en) 1968-11-14

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