GB606811A - Improvements relating to the preparation of cyclohexane and alkylated aromatic hydrocarbons - Google Patents

Improvements relating to the preparation of cyclohexane and alkylated aromatic hydrocarbons

Info

Publication number
GB606811A
GB606811A GB2043345A GB2043345A GB606811A GB 606811 A GB606811 A GB 606811A GB 2043345 A GB2043345 A GB 2043345A GB 2043345 A GB2043345 A GB 2043345A GB 606811 A GB606811 A GB 606811A
Authority
GB
United Kingdom
Prior art keywords
cyclohexane
benzene
methylcyclopentane
per cent
fraction
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
GB2043345A
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.)
Anglo Iranian Oil Co Ltd
Original Assignee
Anglo Iranian Oil Co 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 Anglo Iranian Oil Co Ltd filed Critical Anglo Iranian Oil Co Ltd
Priority to GB2043345A priority Critical patent/GB606811A/en
Publication of GB606811A publication Critical patent/GB606811A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
    • C07C7/14883—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds 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
    • 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
    • C07C2/54—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
    • C07C2/70—Catalytic processes with acids
    • 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
    • C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
    • C07C2527/126—Aluminium chloride
    • 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
    • C07C2527/14—Phosphorus; Compounds thereof
    • C07C2527/16—Phosphorus; Compounds thereof containing oxygen
    • C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
    • 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

Abstract

Hydrocarbon mixtures containing benzene, and cyclohexane or methylcyclopentane or both and, optionally, other hydrocarbons, except olefins, of similar boiling point, are catalytically alkylated with normally gaseous olefins, and the product fractionated to recover alkyl benzenes, and a fraction having a greater ratio of cyclohexane to benzene than the feed, or a fraction containing benzene and methylcyclopentane, which latter fraction is isomerized, and the product fractionated to recover cyclohexane. Mixtures of cyclohexane and benzene, methylcyclopentane, benzene, and hexanes, or cyclohexane, heptanes and benzene prepared as in Specifications 585,850, 606,797, [Group III], or 606,798, may be reacted with ethylene or propylene or mixtures thereof, using Friedel-Crafts' catalysts or phosphoric acid or phosphates, under alkylation conditions, viz. 30 DEG -120 DEG C. with aluminium chloride or its complexes and less than 1 per cent on the feed of hydrogen chloride as activator. Liquid phase reaction is preferred. Methylcyclopentane may simultaneously isomerize to cyclohexane. With phosphoric acid on kieselguhr, 150 DEG -450 DEG C. and 5-20 atm. is used. The combination of the present process with those disclosed in Specifications 606,799, [Group III], or 606,800, also is referred to. In examples: (1) a feed containing methylcyclopentane, n-hexane, cyclohexane, and benzene, is mixed with an aluminium chloride-xylene complex and ethylene and hydrogen chloride introduced at 70 DEG -75 DEG C., the hydrocarbon layer being fractionated to yield a mixture of hexanes, methylcyclopentane, benzene, and a little cyclohexane, pure cyclohexane, and a higher boiling fraction containing ethylbenzene and polyalkylbenzenes; (2) with solid aluminium chloride at 80 DEG C. and 100 p.s.i., 20 per cent of the benzene is converted to alkylbenzenes, about 40 per cent ethylbenzene, and 8 per cent of the methylcyclopentane is isomerized to cyclohexane.
GB2043345A 1945-08-09 1945-08-09 Improvements relating to the preparation of cyclohexane and alkylated aromatic hydrocarbons Expired GB606811A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2043345A GB606811A (en) 1945-08-09 1945-08-09 Improvements relating to the preparation of cyclohexane and alkylated aromatic hydrocarbons

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2043345A GB606811A (en) 1945-08-09 1945-08-09 Improvements relating to the preparation of cyclohexane and alkylated aromatic hydrocarbons

Publications (1)

Publication Number Publication Date
GB606811A true GB606811A (en) 1948-08-20

Family

ID=10145859

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2043345A Expired GB606811A (en) 1945-08-09 1945-08-09 Improvements relating to the preparation of cyclohexane and alkylated aromatic hydrocarbons

Country Status (1)

Country Link
GB (1) GB606811A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008100655A1 (en) * 2007-02-12 2008-08-21 Exxonmobil Chemical Patents Inc. Production of high purity cumene from non-extracted feed and hydrocarbon composition useful therein
US8222467B2 (en) 2007-02-12 2012-07-17 Exxonmobil Chemical Patents Inc. Production of high purity cumene from non-extracted feed and hydrocarbon composition useful therein

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008100655A1 (en) * 2007-02-12 2008-08-21 Exxonmobil Chemical Patents Inc. Production of high purity cumene from non-extracted feed and hydrocarbon composition useful therein
US7683228B2 (en) 2007-02-12 2010-03-23 Exxonmobil Chemical Patents Inc. Production of high purity cumene from non-extracted feed and hydrocarbon composition useful therein
US8222467B2 (en) 2007-02-12 2012-07-17 Exxonmobil Chemical Patents Inc. Production of high purity cumene from non-extracted feed and hydrocarbon composition useful therein

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