GB1076031A - Improvments in or relating to the reaction between conjugated diolefines and phenols - Google Patents

Improvments in or relating to the reaction between conjugated diolefines and phenols

Info

Publication number
GB1076031A
GB1076031A GB17142/64A GB1714264A GB1076031A GB 1076031 A GB1076031 A GB 1076031A GB 17142/64 A GB17142/64 A GB 17142/64A GB 1714264 A GB1714264 A GB 1714264A GB 1076031 A GB1076031 A GB 1076031A
Authority
GB
United Kingdom
Prior art keywords
alkylated
acid
cyclopentadiene
phenol
lambda
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
GB17142/64A
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.)
RUDOLPH SCHACHERL
Carless Capel and Leonard Ltd
Original Assignee
RUDOLPH SCHACHERL
Carless Capel and Leonard 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 RUDOLPH SCHACHERL, Carless Capel and Leonard Ltd filed Critical RUDOLPH SCHACHERL
Priority to GB17142/64A priority Critical patent/GB1076031A/en
Publication of GB1076031A publication Critical patent/GB1076031A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • 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
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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)

Abstract

A process for preparing hydroxy aromatic compounds which carry unsaturated side groups comprises reacting together at least one monohydric phenol having no substituents which contain atoms other than carbon and hydrogen and having at least one unsubstituted position ortho or para to the hydroxy group and a conjugated acyclic or cyclic diene having at least 5 carbon atoms in the presence of a catalytic quantity of an acid having a first dissociation constant, K25 DEG c., greater than 7 x 10-2 or phosphoric acid, and a quantity of water which is at least twice the weight of the anhydrous acid present and at least 1% by weight of the phenol to be reacted. In a modification of the process a catalytic amount of a weak acid, other than phosphoric or hydrofluoric acid, having a dissociation constant K25 DEG c. of less than 7 x 10-2 is employed. In examples: phenol is alkylated with liquid and gaseous cyclopentadiene, p-cresol is alkylated with cyclopentadiene, lambda-nonylphenol is alkylated with cyclopentadiene, b -naphthol is alkylated with cyclopentadiene, lambda-cresol is alkylated with cyclo-hexadiene and phenol is alkylated with piperylene. Catalysts specified in examples include lambda-toluene sulphonic acid and sulphuric acid. The production of cyclic ethers as by-products is mentioned.
GB17142/64A 1964-04-24 1964-04-24 Improvments in or relating to the reaction between conjugated diolefines and phenols Expired GB1076031A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB17142/64A GB1076031A (en) 1964-04-24 1964-04-24 Improvments in or relating to the reaction between conjugated diolefines and phenols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB17142/64A GB1076031A (en) 1964-04-24 1964-04-24 Improvments in or relating to the reaction between conjugated diolefines and phenols

Publications (1)

Publication Number Publication Date
GB1076031A true GB1076031A (en) 1967-07-19

Family

ID=10090021

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17142/64A Expired GB1076031A (en) 1964-04-24 1964-04-24 Improvments in or relating to the reaction between conjugated diolefines and phenols

Country Status (1)

Country Link
GB (1) GB1076031A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932537A (en) * 1971-09-09 1976-01-13 Reichhold Chemicals, Inc. Alkylation of phenols
EP0148817A1 (en) * 1983-06-27 1985-07-24 The Dow Chemical Company Phenolic hydroxyl-containing compositions and epoxy resins prepared therefrom and solid compositions prepared therefrom

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932537A (en) * 1971-09-09 1976-01-13 Reichhold Chemicals, Inc. Alkylation of phenols
EP0148817A1 (en) * 1983-06-27 1985-07-24 The Dow Chemical Company Phenolic hydroxyl-containing compositions and epoxy resins prepared therefrom and solid compositions prepared therefrom
EP0148817A4 (en) * 1983-06-27 1985-11-21 Dow Chemical Co Phenolic hydroxyl-containing compositions and epoxy resins prepared therefrom and solid compositions prepared therefrom.

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