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Mechanism of hydroquinone-inhibited oxidation of acrylic acid and methyl methacrylate

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Abstract

The kinetics of hydroquinone-inhibited oxidation of acrylic acid and methyl methacrylate was studied volumetrically by measuring the oxygen uptake in the presence of an initiator (azobisisobutyronitrile) at T = 333 K and P O 2 = 1 and 0.21 atm. The oxidation of acrylic acid inhibited by 4-methoxyphenol was studied under the same conditions for comparison. The rate constants of the reactions of the peroxyl radicals of acrylic acid (∼CH2CH(COOH)O ·2 ) and methyl methacrylate (∼CH2CMe(COOMe)O ·2 ) with hydroquinone (HOC6H4OH) (1.20 × 105 and 7.16 × 104 l mol−1 s−1, respectively) and of the reaction of peroxyl radicals of acrylic acid with 4-methoxyphenol (p-CH3OC6H4OH) (3.25 × 104 l mol−1 s−1) were measured. The stoichiometric inhibition factors f were determined. The reaction between the semiquinone radical and oxygen, O2 + HOC6H4O·, plays an important role, decreasing the factor f and the efficiency of the inhibition effect of hydroquinone. The rate constants of this reaction were calculated from kinetic data: k = 5.72 × 102 (in acrylic acid) and 4.60 × 102 l mol−1 s−1 (in methyl methacrylate).

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow oblast, 142432, Russia

    N. N. Pozdeeva & E. T. Denisov

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  1. N. N. Pozdeeva
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  2. E. T. Denisov
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Correspondence to E. T. Denisov.

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Original Russian Text © N.N. Pozdeeva, E.T. Denisov, 2011, published in Kinetika i Kataliz, 2011, Vol. 52, No. 4, pp. 517–523.

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Pozdeeva, N.N., Denisov, E.T. Mechanism of hydroquinone-inhibited oxidation of acrylic acid and methyl methacrylate. Kinet Catal 52, 506–512 (2011). https://doi.org/10.1134/S0023158411040136

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  • DOI: https://doi.org/10.1134/S0023158411040136

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