Communications. Free Radical Hydroxylations with Peracetic Acid

Heywood, D. L.; Phillips, Benjamin; Stansbury, Harry A.

doi:10.1021/jo01060a629

Cited by 21 publications

(6 citation statements)

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“…Peracetic acid is in chemical equilibrium with acetic acid and hydrogen peroxide ( K eq 0.37 at room temperature; eq 2) and may undergo homolytic cleavage of the peroxy bond to produce hydroxyl radicals and acetoxyl radicals (eq 3). These radical species may react further to produce peroxyacetoxyl radicals (eq 4), acetaldehyde (eq 5), and methyl radicals (eq 6). , Relative concentrations of these various reactive species are influenced by additional factors, such as the concentration of peracetic acid, temperature, and the availability of metal ions (e.g., Fe 2+ present in some foods may facilitate catalytic Fenton-like reactions to release hydroxyl radicals). Thus, the presence of multiple reactive species in varying concentrations complicates the predictability of reaction mechanisms involving peracids.…”

Section: Resultsmentioning

confidence: 99%

Chemical Inactivation of Protein Toxins on Food Contact Surfaces

Tolleson

Jackson

Triplett

et al. 2012

J. Agric. Food Chem.

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We compared the kinetics and efficacies of sodium hypochlorite, peracetic acid, phosphoric acid-based detergent, chlorinated alkaline detergent, quaternary ammonium-based sanitizer, and peracetic acid-based sanitizer for inactivating the potential bioterrorism agents ricin and abrin in simple buffers, food slurries (infant formula, peanut butter, and pancake mix), and in dried food residues on stainless steel. The intrinsic fluorescence and cytotoxicity of purified ricin and abrin in buffers decreased rapidly in a pH- and temperature-dependent manner when treated with sodium hypochlorite but more slowly when treated with peracetic acid. Cytotoxicity assays showed rapid and complete inactivation of ricin and crude abrin in food slurries and dried food residues treated 0-5 min with sodium hypochlorite. Toxin epitopes recognized by ELISA decayed more gradually under these conditions. Higher concentrations of peracetic acid were required to achieve comparable results. Chlorinated alkaline detergent was the most effective industrial agent tested for inactivating ricin in dried food residues.

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Section: Resultsmentioning

confidence: 99%

Chemical Inactivation of Protein Toxins on Food Contact Surfaces

Tolleson

Jackson

Triplett

et al. 2012

J. Agric. Food Chem.

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“…Relatively short chains are involved in the homolytic cleavage of peracetic acid. The initiation reaction involves the homolysis of PAA peroxy bond into two primary radicals: acyloxy and hydroxyl radicals according to the reaction proposed by Heywood and colleagues in 1961 CH 3 C ( = O ) OOH → CH 3 C ( = O ) O • + • OH …”

Section: Resultsmentioning

confidence: 99%

Free Radical Reaction Pathway, Thermochemistry of Peracetic Acid Homolysis, and Its Application for Phenol Degradation: Spectroscopic Study and Quantum Chemistry Calculations

Rokhina

Makarova

Golovina

et al. 2010

Environ. Sci. Technol.

131

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The homolysis of peracetic acid (PAA) as a relevant source of free radicals (e.g., *OH) was studied in detail. Radicals formed as a result of chain radical reactions were detected with electron spin resonance and nuclear magnetic resonance spin trapping techniques and subsequently identified by means of the simulation-based fitting approach. The reaction mechanism, where a hydroxyl radical was a primary product of O-O bond rupture of PAA, was established with a complete assessment of relevant reaction thermochemistry. Total energy analysis of the reaction pathway was performed by electronic structure calculations (ab initio and semiempirical methods) at different levels and basis sets [e.g., HF/6-311G(d), B3LYP/6-31G(d)]. Furthermore, the heterogeneous MnO2/PAA system was tested for the elimination of a model aromatic compound, phenol from aqueous solution. An artificial neural network (ANN) was designed to associate the removal efficiency of phenol with relevant process parameters such as concentrations of both the catalyst and PAA and the reaction time. Results were used to train and test ANN to identify an optimized network structure, which represented the correlations between the operational parameters and removal efficiency of phenol.

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“…The first and the rate-determining step is the homolysis of the oxygen-oxygen bond (Reaction 2), which requires activation by a transition metal catalyst, UV irradiation, or activated carbon, for instance [81][82][83][84]. All of the generated radicals contribute to the oxidation reactions, but HO·, peracetyl radical (CH 3 COO·), and to a lesser extent the methyl radical (·CH 3 ) have been suggested to be the most important [80,85].…”

Section: Reactions In Aqueous Media: Disinfection and Oxidation Mechamentioning

confidence: 99%

Peracids in water treatment: A critical review

Luukkonen

Pehkonen

2016

Critical Reviews in Environmental Science and Technology

271

122

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Peracids have gained interest in the water treatment over the last few decades. Peracetic acid (CH 3 CO 3 H) has already become an accepted alternative disinfectant in wastewater disinfection whereas performic acid (CHO 3 H) has been studied much less, although it is also already commercially available. Peracids have also been tested for drinking water disinfection, oxidation of aqueous (micro)pollutants, sludge treatment and ballast water treatment, to name just a few examples. The purpose of this review paper is to represent comprehensive up-to-date information about the water treatment applications, aqueous reaction mechanisms, and disinfection byproduct formation of peracids, namely performic, peracetic and perpropionic acids. and PFA have several of the qualities of an ideal disinfectant: toxicity to microorganisms, but not to higher forms of life; effectivity at ambient temperatures; stability and long shelf-life; low corrosivity; deodorizing ability; widespread availability and reasonable cost [12].PAA and PFA are colorless liquids with characteristic pungent odors. Both are thermodynamically unstable and can decompose spontaneously or explode when highly concentrated, heated, under mechanical stress or exposed to catalytic effects of impurities [1,13,14]. The recommended storage temperatures are below 30 and 20°C for PAA and PFA, respectively [6,14]. Longer carbon chain length increases stability, and thus PAA is more stable than PFA [1]. However, the O-O bond dissociation energy of PFA and PAA has been calculated to be similar: 48 kcal/mol [15]. Percarboxylic acids have typically pK a values 3-4 units higher than the parent carboxylic acids [1]. Nonetheless, PFA and PAA are corrosive [16]. ACCEPTED MANUSCRIPT ACCEPTED MANUSCRIPT 3Exposure to PAA and PFA causes irritation and possibly permanent damage to the skin (cutaneous emphysema), eyes and the respiratory system. In the skin contact, 0.2% is proposed as the no-observed-effect concentration (NOEC) for short and medium length exposure [17].When inhaled, airborne concentrations less than 0.16-0.17 ppm (0.50-0.52 mg/m 3 ) are considered to cause no irritation [17,18]. However, higher concentrations are harmful and a case study suggested that PAA could cause occupational asthma [19].The largest users of PAA on a global scale (estimated in 2013) are shown in Fig. 1. Similar numbers are not available for PFA, but it is probably used at significantly lower quantities.The largest user, the food industry, applies PAA as a disinfectant in fresh produce washing water, clean-in-place (CIP) processes, on food processing equipment, and in pasteurizers, to name just a few examples [21,22]. PFA is also a suitable disinfectant in low-temperature refrigerated food processing and storage rooms [23]. In healthcare, PAA is used for instance in Recently, methods to determine the residual PAA from wastewater were compared: the spectrophotometric method using DPD and catalase was recommended for 0.1-0.5 mg/L PAA concentrations and the cerimetric/iodometric titration...

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Communications. Free Radical Hydroxylations with Peracetic Acid

Cited by 21 publications

References 0 publications

Chemical Inactivation of Protein Toxins on Food Contact Surfaces

Chemical Inactivation of Protein Toxins on Food Contact Surfaces

Free Radical Reaction Pathway, Thermochemistry of Peracetic Acid Homolysis, and Its Application for Phenol Degradation: Spectroscopic Study and Quantum Chemistry Calculations

Peracids in water treatment: A critical review

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