GB794570A - Improvements in and relating to the alkylation of aromatic hydrocarbons - Google Patents

Improvements in and relating to the alkylation of aromatic hydrocarbons

Info

Publication number
GB794570A
GB794570A GB642155A GB642155A GB794570A GB 794570 A GB794570 A GB 794570A GB 642155 A GB642155 A GB 642155A GB 642155 A GB642155 A GB 642155A GB 794570 A GB794570 A GB 794570A
Authority
GB
United Kingdom
Prior art keywords
stage
cumene
catalyst
isopropyl
taken
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
GB642155A
Inventor
Edmund Theodore Crisp
Norman Hardie Keir
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB642155A priority Critical patent/GB794570A/en
Publication of GB794570A publication Critical patent/GB794570A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/085—Isopropylbenzene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • 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
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C07C2/68—Catalytic processes with halides
    • 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
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/861—Preparation 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
    • C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
    • C07C5/2732—Catalytic processes
    • C07C5/274—Catalytic processes with inorganic acids; with salts or anhydrides of acids
    • C07C5/2748—Acids of halogen; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
    • C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
    • C07C5/2732—Catalytic processes
    • C07C5/274—Catalytic processes with inorganic acids; with salts or anhydrides of acids
    • C07C5/2748—Acids of halogen; Salts thereof
    • C07C5/2751—Metal halides; Complexes thereof with organic compounds
    • 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
    • C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
    • C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
    • 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
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

794,570. Iso-propyl benzenes. IMPERIAL CHEMICAL INDUSTRIES, Ltd. Feb. 3, 1956 [March 4, 1955], No. 6421/55. Class 2 (3). A di-isopropyl benzene and cumene are obtained by reacting benzene in a first stage in the liquid stage at 5-100‹ C. with propylene or a propylhalide in the presence of a liquid complex alkylation catalyst comprising a strongly active Friedel-Crafts catalyst, at least some hydrogen halide, and an alkylated aromatic hydrocarbon which is immiscible with the starting hydrocarbons and products, to give a mixture containing at least di-isopropyl benzenes and cumene, separating this mixture from the catalyst complex, separating off cumene and a di-isopropyl benzene, subjecting the residual mixture in a second stage in the liquid phase at from 5-100‹ C. in the presence of a further quantity of a similar complex catalyst whereby isomerization and interalkylation occur, separating the mixed product from the liquid catalyst and recovering a di-isopropyl benzene and cumene by fractional separation, preferably distillation, the formation of complexes and subsequent crystallization, adsorption and chromatography. The catalytic complex may be aluminium chloride, a hydrocarbon containing cumene and/or higher isopropyl benzenes and hydrogen chloride; or boron fluoride, a similar hydrocarbon, and hydrogen fluoride. The catalyst is preferably used fresh in the second stage and subsequently circulated to the first stage. In a preferred form of the invention, which is operated in a continuous manner, the product from the first stage reactor is fed, together with the product from the second stage reactor, to a series of 4 distillation columns. In the first of these benzene is taken off as an overhead and recycled to the first stage, in the second, cumene is taken off as overhead, in the third, mixed ortho- and meta-di-isopropyl benzenes are taken off and recycled to the second stage and in the fourth, para-di-isopropyl benzene is taken off as overhead (and taken to storage) and tri-isopropyl benzene as bottom product which is returned to the second stage reactor. The temperature is preferably from 40-80‹ C. in the first stage.
GB642155A 1955-03-04 1955-03-04 Improvements in and relating to the alkylation of aromatic hydrocarbons Expired GB794570A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB642155A GB794570A (en) 1955-03-04 1955-03-04 Improvements in and relating to the alkylation of aromatic hydrocarbons

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB642155A GB794570A (en) 1955-03-04 1955-03-04 Improvements in and relating to the alkylation of aromatic hydrocarbons

Publications (1)

Publication Number Publication Date
GB794570A true GB794570A (en) 1958-05-07

Family

ID=9814195

Family Applications (1)

Application Number Title Priority Date Filing Date
GB642155A Expired GB794570A (en) 1955-03-04 1955-03-04 Improvements in and relating to the alkylation of aromatic hydrocarbons

Country Status (1)

Country Link
GB (1) GB794570A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2920118A (en) * 1954-11-08 1960-01-05 Mid Century Corp Process for the preparation of alkylaryl compounds
DE1148220B (en) * 1959-01-10 1963-05-09 Universal Oil Prod Co Process for alkylating aromatic hydrocarbons with olefins in the presence of boron trifluoride
FR2529881A1 (en) * 1982-07-06 1984-01-13 Ugine Kuhlmann Process for the preparation of practically pure meta-diisopropylbenzene.
EP0190057A1 (en) * 1985-01-31 1986-08-06 The Dow Chemical Company Process for the alkylation of aromatic hydrocarbons
EP0395360A1 (en) * 1989-04-25 1990-10-31 Sumitomo Chemical Company, Limited Process for production of sec-butylbenzene

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2920118A (en) * 1954-11-08 1960-01-05 Mid Century Corp Process for the preparation of alkylaryl compounds
DE1148220B (en) * 1959-01-10 1963-05-09 Universal Oil Prod Co Process for alkylating aromatic hydrocarbons with olefins in the presence of boron trifluoride
FR2529881A1 (en) * 1982-07-06 1984-01-13 Ugine Kuhlmann Process for the preparation of practically pure meta-diisopropylbenzene.
EP0190057A1 (en) * 1985-01-31 1986-08-06 The Dow Chemical Company Process for the alkylation of aromatic hydrocarbons
EP0395360A1 (en) * 1989-04-25 1990-10-31 Sumitomo Chemical Company, Limited Process for production of sec-butylbenzene

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