Peroxyacetic Acid Oxidation of Olefins and Alkanes Catalyzed by a Dinuclear Manganese(IV) Complex with 1,4,7-trimethyl-1,4,7-triazacyclononane

Mandelli, Dalmo; Kozlov, Yuriy N.; Golfeto, Camilla C.; Shul’pin, Georgiy B.

doi:10.1007/s10562-007-9172-z

Cited by 24 publications

(3 citation statements)

References 72 publications

(71 reference statements)

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“…The use of PAA for the degradation of pollutants in wastewater has also been studied by some researchers. In particular, activation of PAA by energy (UV or solar) or catalysts [e.g., Fe(II/III), Co(II/III), Mn(II/III/IV), Ru(III), V(IV/V), and activated carbon] creating advanced oxidation conditions has shown high efficiency for the removal of a variety of organic pollutants. ,,,− The enhanced removal of pollutants, compared to PAA alone, is derived from the formation of reactive radical species, such as • OH and CH 3 C(O)OO • , which were confirmed by electron paramagnetic resonance (EPR) analysis and/or radical quenching experiments. ,,,,− The reaction mechanism and reactivities of organic compounds with respect to radicals formed from activated PAA should be different from those of direct oxidation by PAA. This review paper focuses on the reaction of compounds by PAA, not by activated PAA.…”

Section: Background Of Paamentioning

confidence: 99%

Reactivity of Peracetic Acid with Organic Compounds: A Critical Review

2020

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As an emerging oxidant and disinfectant, peracetic acid (PAA) has increasingly been used in wastewater treatment and the food and medical industries and has attracted greater research interest. To better understand reactions initiated by PAA, this paper is among the first to comprehensively review the reactivity of PAA with respect to organic compounds of various structures. The reactivities of PAA with respect to 123 organic compounds are compiled from the literature and new experiments, and possible reaction pathways and products are discussed. Overall, PAA is an electrophile with high selectivity in reaction. The second-order rate constants of PAA oxidation of organic compounds vary by nearly 10 orders of magnitude, from 3.2 × 10 −6 to >1.0 × 10 5 M −1 s −1 , which are much larger than those of H 2 O 2 coexisting in PAA solutions. Electron-donating groups of compounds increase the reactivity with respect to PAA, evidenced by the strong negative correlations between rate constants and substituent constants [Hammett (σ) or Taft (σ*)] of compounds. Sulfur moieties show exceptionally high reactivity with respect to PAA. Limited studies have shown that generally oxygen-added reaction products are formed from PAA oxidation. This critical review provides a useful foundation for advancing our understanding of the fate of organic compounds in wastewater treatment including PAA and identifies further research needs to evaluate a broader range of compounds and their oxidation products and toxicity.

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Section: Background Of Paamentioning

confidence: 99%

Reactivity of Peracetic Acid with Organic Compounds: A Critical Review

2020

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“…Previous research has employed a variety of metals, such as Fe(II/III/VI), Co(II/III), Mn(II/III/IV), Ru(III), and V(IV/V), to activate PAA. ,− ,− Among them, Fe is environmentally abundant and benign. The Fenton reaction was first discovered by Fenton, and it has been applied for pollution remediation since the late 1960s .…”

Section: Introductionmentioning

confidence: 99%

Enhanced Degradation of Micropollutants in a Peracetic Acid–Fe(III) System with Picolinic Acid

Kim

Wang

Ashley

et al. 2022

Environ. Sci. Technol.

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Activation of peracetic acid (PAA) with iron species is an emerging advanced oxidation process (AOP). This study investigates the use of the chelating agent picolinic acid (PICA) to extend the pH range and enhance the performance of the PAA–Fe(III) AOP. Compared to the PAA–Fe(III) system, the PAA–Fe(III)–PICA system degrades various micropollutants (MPs: methylene blue, naproxen, sulfamethoxazole, carbamazepine, trimethoprim, diclofenac, and bisphenol-A) much more rapidly at higher pH, achieving almost complete removal of parent compounds within 10 min. PAA significantly outperforms the coexistent H2O2 and is the key oxidant for rapid compound degradation. Other chelating agents, EDTA, NTA, citric acid, proline, and nicotinic acid, could not enhance MP degradation in the PAA–Fe(III) system, while 2,6-pyridinedicarboxylic acid with a structure similar to PICA moderately enhanced MP degradation. Experiments with scavengers (tert-butyl alcohol and methyl phenyl sulfoxide) and a probe compound (benzoic acid) confirmed that high-valent iron species [Fe(IV) and/or Fe(V)], rather than radicals, are the major reactive species contributing to MP degradation. The oxidation products of methylene blue, naproxen, and sulfamethoxazole by PAA–Fe(III)–PICA were characterized and supported the proposed mechanism. This work demonstrates that PICA is an effective complexing ligand to assist the Fenton reaction of PAA by extending the applicable pH range and accelerating the catalytic ability of Fe(III).

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“…A relevant soluble polymer-bound Mn(IV) complex with N-alkylated 1,4,7-triazacyclononane was used as a catalyst in the H 2 O 2 oxygenation of alkanes [82]. We have also demonstrated that alkanes and olefins can be oxidized by tert-butyl hydroperoxide [72,95,96] or peroxyacetic acid [81,97] using complex 1a as a catalyst. The reaction with tert-butyl hydroperoxide is significantly accelerated in the presence of a small amount of a carboxylic acid [72,96].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of Reactive Alcohols with Hydrogen Peroxide Catalyzed by Manganese Complexes

et al. 2010

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Two manganese-containing catalysts have been employed in the oxidation with hydrogen peroxide of two reactive alcohols (1-phenylethanol and glycerol): soluble catalyst [LMn(l-O) 3 MnL](PF 6 ) 2 (1a) and heterogenized catalyst [LMn(l-O) 3 MnL] 2 [SiW 12 O 40 ] (1b) (L is 1 ,4,4, TMTACN). Oxidation of 1-phenylethanol catalyzed by 1a in acetonitrile solution proceeds at room temperature in the presence of a small amount of oxalic acid; the turnover number attains 15,000 after 3 h. It has been proposed on the basis of the kinetic study that an oxidizing species is a manganyl species containing fragment ''Mn=O'' rather that hydroxyl radical. This species reacts competitively with the alcohol, acetonitrile and hydrogen peroxide. In the case of 1b dependences of the initial rates of acetophenone accumulation on concentration of the alcohol and amount of 1b have plateau. Both homogeneous and heterogeneous catalysts are efficient in the oxidation of glycerol to produce dihydroxyacetone (DHA) as the main product. The oxidation catalyzed by 1a is one of the first examples of the glycerol oxidation by a catalytic homogeneous system. The yield of valuable products attained 45%. The oxidation of DHA in the absence of glycerol afforded mainly glycolic acid in yield 60% based on the starting DHA. The oxidation on 1b represents the first example of the glycerol transformation catalyzed by a heterogenized metal complex. Under certain conditions yields of products of deeper oxidation (glyceric, glycolic and hydroxypyruvic acids) are somewhat higher than the yield of dihydroxyacetone. Special experiments demonstrated that no leaching of active species occurs from catalyst 1b to the solution and that this catalyst can be re-used at least four times without substantial loss of activity.

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Peroxyacetic Acid Oxidation of Olefins and Alkanes Catalyzed by a Dinuclear Manganese(IV) Complex with 1,4,7-trimethyl-1,4,7-triazacyclononane

Cited by 24 publications

References 72 publications

Reactivity of Peracetic Acid with Organic Compounds: A Critical Review

Reactivity of Peracetic Acid with Organic Compounds: A Critical Review

Enhanced Degradation of Micropollutants in a Peracetic Acid–Fe(III) System with Picolinic Acid

Oxidation of Reactive Alcohols with Hydrogen Peroxide Catalyzed by Manganese Complexes

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