Diethyl Sulfide Oxidation with Activated Hydrogen Peroxide

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Resumo

The development of environmentally favorable and effective methods for the disposal of chemical weapons is an important task in ensuring the ecological stability of the environment and reducing the risk of emergency situation. The review presents a comparative analysis of metal-free oxidation systems of diethyl sulfide (Et2S), a simulator of the chemical warfare agent mustard gas (2,2′-dichlorodiethyl sulfide), based on hydrogen peroxide and its activators that meet the requirements of “green chemistry”. The ways for increasing the solubility of the thioester in the reaction mixture that lead to an increase of oxidation rate were analyzed. A choice of oxidation systems, depending on the pH of the reaction medium, is proposed.

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Sobre autores

T. Bezbozhnaya

L.M. Litvinenko Institute of Physical Organic and Coal Chemistry

Autor responsável pela correspondência
Email: b.t.v.57@rambler.ru
Rússia, R. Luxemburg st., 70, Donetsk, DPR, 283048

А. Liubymova

L.M. Litvinenko Institute of Physical Organic and Coal Chemistry

Email: b.t.v.57@rambler.ru
Rússia, R. Luxemburg st., 70, Donetsk, DPR, 283048

V. Lobachev

L.M. Litvinenko Institute of Physical Organic and Coal Chemistry

Email: b.t.v.57@rambler.ru
Rússia, R. Luxemburg st., 70, Donetsk, DPR, 283048

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2. Fig. 1. pH-dependences of the oxidation rate constants of Et2S in the systems: 1 – H2O2 (0.03 mol/l), 2 – H2O2 (0.03 mol/l)–NaHCO3 (0.006 mol/l) [22].

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3. Fig. 2. Dependences of the rate constants of diethyl sulfide oxidation by hydrogen peroxide on the concentration of surfactants: CTAB (1), Triton (2), GC-MCIH (3) and SDS (4) [23].

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4. Fig. 3. Dependences of the rate constants of oxidation of diethyl sulfide by peroxymonocarbonate on the concentration of surfactants: CTAB (1), Triton (2), GK-MCIH (3) and SDS (4) [23].

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5. Fig. 4. pH-dependences of the rate constants of Et2S oxidation in the H2O2 (0.02 mol/l)–B(OH)3 (0.02 mol/l) system at a temperature of 25°C in water (1) and in aqueous-alcoholic media with a H2O : ROH (vol. %) ratio of 70 : 30: H2O–C2H4(OH)2 (2), H2O–i-PrOH (3), H2O–EtOH (4); H2O–t-BuOH (5) [24].

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6. Fig. 5. Dependences of the rate constants of Et2S oxidation by hydrogen peroxide (1) and in the H2O2 (0.02 mol/l)–B(OH)3 (0.02 mol/l) system (2) on the concentration of CTAB. Conditions: pH 9.0; 25°C [28].

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7. Fig. 6. Dependences of the rate constants of Et2S oxidation by aqueous solutions of hydrogen peroxide (1) and sodium peroxoborate (2) on the pH of the medium [13].

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8. Fig. 7. pH-dependences of the rate constants of Et2S oxidation at a temperature of 25°C with hydrogen peroxide (1); peroxoborate (0.015 mol/l) (3) and in the systems H2O2 (0.03 mol/l)–NaHCO3 (0.06 mol/l) (2); PB (0.015 mol/l)–NaHCO3 (0.006 mol/l) (4) [22].

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9. Fig. 8. pH-dependences of the initial rates of Et2S oxidation by hydrogen peroxide in aqueous solutions (1) and in a mixture of H2O–MeCN ([MeCN] = 1 vol. %) (2). Conditions: [H2O2] = 0.006 mol/l, [Et2S] = 4.2 × 10-5 mol/l; 25°C [29].

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10. Fig. 9. pH-dependences of the initial rates of Et2S oxidation at 25°C: 1 – with sodium peroxoborate in aqueous solutions ([PB] = 0.002 M); 2 – in the H2O–PB–MeCN system ([MeCN] = 0.19 M (1 vol. %), [PB] = 0.002 M); 3 – in the H2O2–MeCN– –H2O system ([H2O2] = 0.006 M, [MeCN] = 0.19 M (1 vol. %)); [Et2S] = 4.2 × 10-5 mol/L [34].

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11. Scheme 1. State of hydrogen peroxide in various environments.

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12. Scheme 2. Structural formulas of surfactants.

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13. Scheme 3. State of boric acid in solutions.

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14. Scheme 4. Oxidation of diethyl sulfide with hydrogen peroxide in acetonitrile.

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