Antioxidant Activity of 6-Amino-5-hydroxy-2,3-dimethylpyrimidine-4(3Н)-one in Model Systems of Radical Chain Oxidation of Tetrahydrofuran and Methyloleate

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Abstract

The antioxidant activity of 6-amino-5-hydroxy-2,3-dimethylpyrimidin-4(3H)-one (ODMAU) was measured in two model radical chain reactions at a temperature of 309 K. The rate constants of the interaction of ODMAU with peroxyl radicals of tetrahydrofuran and methyl oleate (k7) are equal to: (3.8±0.5) × 105 and (5.0±0.8) × 104 L mol–1 s–1, respectively. The stoichiometric inhibition coefficient f ≈ 1 in the medium of tetrahydrofuran and methyl oleate indicates that one inhibitor molecule trap one radical. It is assumed that during the inhibited radical-chain oxidation of tetrahydrofuran and methyl oleate, chain termination occurs through the reaction of the peroxyl radical with ODMAU. The radicals formed from the inhibitor are consumed by reaction with each other.

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About the authors

L. R. Yakupova

Ufa Institute of Chemistry, Ufa Federal Research Center RAS

Author for correspondence.
Email: stargar@inbox.ru
Russian Federation, prosp. Oktyabrya, 69, Ufa, Bashkortostan, 450054

R. A. Nasibullina

Ufa Institute of Chemistry, Ufa Federal Research Center RAS

Email: stargar@inbox.ru
Russian Federation, prosp. Oktyabrya, 69, Ufa, Bashkortostan, 450054

S. A. Grabovsky

Ufa Institute of Chemistry, Ufa Federal Research Center RAS

Email: stargar@inbox.ru
Russian Federation, prosp. Oktyabrya, 69, Ufa, Bashkortostan, 450054

R. L. Safiullin

Ufa Institute of Chemistry, Ufa Federal Research Center RAS

Email: stargar@inbox.ru
Russian Federation, prosp. Oktyabrya, 69, Ufa, Bashkortostan, 450054

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Supplementary files

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2. Scheme

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3. Scheme 1. The mechanism of liquid-phase radical chain oxidation of tetrahydrofuran.

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4. 1. Typical kinetic dependences of oxygen uptake during THF oxidation: without the addition of an inhibitor (1); [ODMAU] = 1.2 × 10-5 mol/l (2); [AscH] = 1.2 × 10-5 mol/l (3); [ODMAU] = 1.2 × 10-5 mol/L, [AscH] = 1.2 × 10-5 mol/L (4). Reaction conditions: [THF] = 12.2 mol/L, wi = 2.1 × 10-8 mol l–1 s–1, 309 K.

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5. Fig. 2. Dependence of the initial oxidation rate of tetrahydrofuran on the concentration of the ODMAU compound (1) and its transformation (2) in the coordinates of equation (1). Reaction conditions: [THF] = 12.4 mol/l, wi = 2.1 × 10-8 mol l–1 s–1, 309 K.

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6. 3. Typical kinetic dependences of oxygen uptake during the oxidation of methyloleate: without the addition of an inhibitor (1); [ODMAU] = 1.1 × 10-5 mol/l (2). Reaction conditions: [MO] = 1.3 mol/l, wi = 4 × 10-8 mol l–1 s–1, 309 K.

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