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Vapour-phase Chemistry of Arenes. Part 11. Autoxidation of Chlorobenzene between 500-1100 K. Mechanisms of Formation of Chlorophenols and Phenol

DOI: 10.1039/P29860001541

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1541 - 1550 (1986)

Update date:2022-08-25

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Authors:

Mulder, PeterMulder, Peter

Louw, RobertLouw, Robert

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Article abstract of DOI:10.1039/P29860001541

Slow combustion of chlorobenzene (1) has been studied at low degrees of conversion (<5percent); mostly at atmospheric pressure, but at ca. 1080 K under FVT-like conditions.Emphasis was on formation of the hydroxy derivatives o/m/p-ClC6H4OH (2) and the ipso substitution product phenol (3).A variety of ingredients, such as ButOOH, cyclohexane, nitroethane, and hydrogen peroxide, forming .OH in situ by thermolysis or autoxidation, has been used to induce the reaction of (1).The change in product composition (2,3) with temperature revealed a major change in mechanism of hydroxylation between 600-700 K.Above ca. 600 K, H-abstraction (1) + .OH -> o/m/p-ClC6H4. .OH -> Cl. + (3)> is followed by rapid addition of O2 (step 4) to give C6H4OO. radicals (v).At moderate temperatures (v) reacts bimolecularly, with itself or with HO2., leading to ClC6H4O. (iv) and therefrom to (2).Thermokinetic analysis emphasises that at elevated temperatures (v) decomposes into (iv) and O(3P).The latter species adds to (1) and forms (2) rather efficiently, with an isomer distribution different from that associated with the pathway Ar. -> ArO2. -> ArOH.Data on model runs, including kinetic isotope effect measurements on p-DC6H4Cl and C6H6/C6D6 support our mechanistic interpretation.

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