GB895928A - A process for the preparation of 2,6-dialkyl phenols - Google Patents

A process for the preparation of 2,6-dialkyl phenols

Info

Publication number
GB895928A
GB895928A GB39934/60A GB3993460A GB895928A GB 895928 A GB895928 A GB 895928A GB 39934/60 A GB39934/60 A GB 39934/60A GB 3993460 A GB3993460 A GB 3993460A GB 895928 A GB895928 A GB 895928A
Authority
GB
United Kingdom
Prior art keywords
phenol
dialkyl
catalyst
reaction mixture
alkyl
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
GB39934/60A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB895928A publication Critical patent/GB895928A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/06Alkylated phenols
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54Preparation 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
    • C07C2/64Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66Catalytic processes

Landscapes

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

Abstract

A process for the preparation of a 2,6-di-alkyl phenol unsubstituted in the 4 position comprises mixing an aluminium halide catalyst with a phenol having a replaceable hydrogen atom on the ring carbon atoms in the para and at least one of the ortho positions relative to the hydroxyl group, at a temperature of at least 130 DEG C., mixing the resulting mixture with a molar excess of a mono-olefin, heating the mixture of phenol, mono-olefin and catalyst under pressure and separaing the 2,6-dialkyl phenol from the reaction mixture. The product is preferably separated from the reaction mixture between the time at which the ratio of the molar concentration of the 2,6-dialkyl phenol to the sum of the molar concentrations of 2,6-dialkyl phenol, 4-alkyl phenol, 2,4-dialkyl phenol and 2,4,6-trialkyl phenol is a maximum and the time at which the concentration of the 2,6-dialkyl phenol in the reaction mixture is a maximum. The preferred reactants are phenol itself or phenol substituted by alkyl, halogen, amino or nitro groups and alkenes containing up to 10 carbon atoms or aryl olefins. The reaction is preferably carried out at 100 DEG C.-150 DEG C. in the absence of a molecular oxygen, water and iron and using a catalyst promotor, e.g. a halogen compound. In the example phenol is alkylated with isobutylene in the presence of aluminium chloride and tert. butyl chloride as promotor using various temperatures for the catalyst addition and the alkylation. Reference has been directed by the Comptroller to Specification 843,745.
GB39934/60A 1959-11-23 1960-11-21 A process for the preparation of 2,6-dialkyl phenols Expired GB895928A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US895928XA 1959-11-23 1959-11-23

Publications (1)

Publication Number Publication Date
GB895928A true GB895928A (en) 1962-05-09

Family

ID=31975708

Family Applications (1)

Application Number Title Priority Date Filing Date
GB39934/60A Expired GB895928A (en) 1959-11-23 1960-11-21 A process for the preparation of 2,6-dialkyl phenols

Country Status (1)

Country Link
GB (1) GB895928A (en)

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