Kinetics and mechanism of the alkylation of phenol with cyclohexene in the presence of aluminum phenolate

Journal Article · Wed Oct 01 00:00:00 EDT 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:7005979

Kozlivoskii, Y B; Chernyaev, B V; Koshchii, V A

The kinetics of the alkylation of phenol with cyclohexene in the presence of aluminum phenolate was studied. A mechanism is proposed for the ortho-alkylation of phenols by olefins, involving the intermediate formation of the ion pair (Al(OPh)/sub 4/)/sup -/R/sup +/ at a steady concentration. The ion pair is transformed into the o-alkylphenol in the controlling stage. The alkylation rate of phenol is higher than that of 2-cyclohexylphenol, and this is due to the determining effect of the entropy factor.

• Research Organization: Kiev Polytechnic Institute
• OSTI ID: 7005979
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:5,PT.2; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKENES
ALKYLATION
ALUMINIUM COMPOUNDS
AQUEOUS SOLUTIONS
AROMATICS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CYCLOALKENES
DISPERSIONS
ENTROPY
HEXENES
HYDROCARBONS
HYDROXY COMPOUNDS
KINETICS
MIXTURES
ORGANIC COMPOUNDS
ORGANOMETALLIC COMPOUNDS
PHENOL
PHENOLATES
PHENOLS
PHYSICAL PROPERTIES
QUANTITY RATIO
REACTION KINETICS
SOLUTIONS
SYNTHESIS
TEMPERATURE DEPENDENCE
TEMPERATURE EFFECTS
THERMODYNAMIC PROPERTIES
YIELDS