GB731270A - Improvements in or relating to the alkylation of phenols and naphthols - Google Patents

Improvements in or relating to the alkylation of phenols and naphthols

Info

Publication number
GB731270A
GB731270A GB13532/52A GB1353252A GB731270A GB 731270 A GB731270 A GB 731270A GB 13532/52 A GB13532/52 A GB 13532/52A GB 1353252 A GB1353252 A GB 1353252A GB 731270 A GB731270 A GB 731270A
Authority
GB
United Kingdom
Prior art keywords
give
phenol
cresol
olefines
sulphonated
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
GB13532/52A
Inventor
Leonard Harrison Groves
Arthur Lambert
Herbert Palfreeman
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 GB13532/52A priority Critical patent/GB731270A/en
Publication of GB731270A publication Critical patent/GB731270A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B01J31/08—Ion-exchange resins
    • B01J31/10—Ion-exchange resins sulfonated
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4007—Regeneration or reactivation of catalysts containing polymers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Phenols having at least one unsubstituted ortho or para position such as phenol, cresols and xylenols, and naphthols having at least one corresponding position unsubstituted, i.e. a -naphthol having the 2- and/or 4-position unsubstituted or a b -naphthol having a 2-, 3- and/or 6-position unsubstituted, are alkylated by reaction with an olefine in the presence of a cation exchange resin of the sulphonated polymer type as a catalyst. Specified olefines include aliphatic olefines of the type R.(CH3).C=CHR1 where R and R1 may be hydrogen atoms or alkyl groups of 1-5 carbon atoms, e.g. propylene, iso-butene, amylenes and octenes, cycloaliphatic olefines such as cyclohexenes and cyclopentenes which may be substituted by alkyl groups and aromatic olefines such as styrene or a -methylstyrene. Particularly suitable cation exchange resins are those of the sulphonated polystyrene and phenol/sodium bisulphite/formaldehyde type. In examples: "Zeokarb" (Registered Trade Mark) and "Amberlite" (Registered Trade Mark) cation-exchange resins comprising nuclear sulphonated phenolic, sulphonated polystyrene or phenol/sodium bisulphite/formaldehyde resins are used as catalysts in the reaction between (1) p-cresol and iso-butene to give 4-methyl-6-tert-butylphenol; (2) p-cresol and cyclohexene to give 4-methyl-2-cyclohexyl phenol; (3) phenol and diisobutene to give octylphenol; (4) p-cresol and 1-methylcyclohexene to give 2 - a - methylcyclohexyl - 4 - methylphenol; (5) a mixture of 2 : 4- and 2 : 5-dimethylphenol and isobutene to give 6-tert-butyl-2 : 4-dimethylphenol and tert-butyl-2 : 5-dimethylphenol; (6) p-cresol and 1-methylcyclohexene to give 2-a -methylcyclohexyl-4-methylphenol. Diisobutene is prepared by treating tertiary butanol with sulphuric acid.
GB13532/52A 1952-05-28 1952-05-28 Improvements in or relating to the alkylation of phenols and naphthols Expired GB731270A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB13532/52A GB731270A (en) 1952-05-28 1952-05-28 Improvements in or relating to the alkylation of phenols and naphthols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB13532/52A GB731270A (en) 1952-05-28 1952-05-28 Improvements in or relating to the alkylation of phenols and naphthols

Publications (1)

Publication Number Publication Date
GB731270A true GB731270A (en) 1955-06-08

Family

ID=10024691

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13532/52A Expired GB731270A (en) 1952-05-28 1952-05-28 Improvements in or relating to the alkylation of phenols and naphthols

Country Status (1)

Country Link
GB (1) GB731270A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2915563A (en) * 1958-01-07 1959-12-01 Shell Dev Allylation of aromatic compounds
US3422157A (en) * 1966-04-18 1969-01-14 Union Carbide Corp Process for continuous alkylation of arylhydroxides using ion exchange resins
US4292450A (en) * 1979-11-26 1981-09-29 Conoco, Inc. Selective alkylation of 2,5-xylenol in the presence of 2,4-xylenol
EP0370343A1 (en) * 1988-11-25 1990-05-30 Bayer Ag Method for the production of 4-methyl-2-cyclohexylphenol

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2915563A (en) * 1958-01-07 1959-12-01 Shell Dev Allylation of aromatic compounds
US3422157A (en) * 1966-04-18 1969-01-14 Union Carbide Corp Process for continuous alkylation of arylhydroxides using ion exchange resins
US4292450A (en) * 1979-11-26 1981-09-29 Conoco, Inc. Selective alkylation of 2,5-xylenol in the presence of 2,4-xylenol
EP0370343A1 (en) * 1988-11-25 1990-05-30 Bayer Ag Method for the production of 4-methyl-2-cyclohexylphenol
US4990687A (en) * 1988-11-25 1991-02-05 Bayer Aktiengesellschaft Preparation of 4-methyl-2-cyclohexylphenol

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