| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name Ethaneperoxoic acid[1] | |||
| Other names Peroxyacetic acid Acetic peroxide Acetyl hydroperoxide Proxitane Percidine | |||
| Identifiers | |||
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3D model (JSmol) | |||
| Abbreviations | PAA | ||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.001.079 | ||
| EC Number |
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| KEGG |
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| RTECS number |
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| UNII | |||
| UN number | 3107 3105 | ||
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| Properties | |||
| CH3CO3H | |||
| Molar mass | 76.05 g/mol | ||
| Appearance | Colorless liquid | ||
| Density | 1.0375 g/mL | ||
| Melting point | 0 °C (32 °F; 273 K)[2] | ||
| Boiling point | 105 °C (221 °F; 378 K) 25 C @ (1.6 kPa)[2] | ||
| Acidity (pKa) | 8.2 | ||
Refractive index (nD) | 1.3974 (589 nm, 20 °C)[2] | ||
| Viscosity | 3.280cP | ||
| Pharmacology | |||
| QG51AD03 (WHO) | |||
| Hazards | |||
| GHS labelling: | |||
    | |||
| Danger | |||
| H226,H242,H302,H312,H314,H332,H400 | |||
| P210,P220,P233,P234,P240,P241,P242,P243,P260,P261,P264,P270,P271,P273,P280,P301+P312,P301+P330+P331,P302+P352,P303+P361+P353,P304+P312,P304+P340,P305+P351+P338,P310,P312,P321,P322,P330,P363,P370+P378,P391,P403+P235,P405,P411,P420,P501 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 40.5 °C (104.9 °F; 313.6 K) | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Peracetic acid (also known asperoxyacetic acid, orPercidine) is anorganic compound with theformula CH3CO3H. Thisperoxy acid is a colorless liquid with a characteristic acrid odor reminiscent ofacetic acid. It can be highlycorrosive.
Peracetic acid is a weaker acid than the parent acetic acid, with apKa of 8.2.[2]
Peracetic acid is produced industrially by theautoxidation ofacetaldehyde:[2]
Peracetic acid is conventionally prepared by combiningacetic acid andhydrogen peroxide with homogeneous acid catalysts (e.g., sulfuric acid), which facilitate the reaction and achieve equilibrium between the reagents and product:[3]
While it is feasible to create peracetic acid by combining consumer-grade vinegar (5%acetic acid) andhydrogen peroxide (3%) without an acid catalyst, the low concentration of reagents will result in a slow reaction rate at room temperature. Extrapolating from published reaction rates,[4] the time to equilibrium is estimated to be on the order of weeks.
As an alternative,acetyl chloride andacetic anhydride can be used to generate a solution of the acid with lower water content.
Peracetic acid is also generatedin situ by somelaundry detergents. This is achieved by the action ofbleach activators, such astetraacetylethylenediamine andsodium nonanoyloxybenzenesulfonate, upon hydrogen peroxide formed fromsodium percarbonate in water. The peracetic acid is a more effectivebleaching agent than hydrogen peroxide itself.[5][6] PAA is also formed naturally in the environment through a series ofphotochemical reactions involvingformaldehyde and photo-oxidantradicals.[7]
Peracetic acid is always sold in solution as a mixture with acetic acid and hydrogen peroxide to maintain its stability. The concentration of the acid as the active ingredient can vary.
TheUnited States Environmental Protection Agency first registered peracetic acid as anantimicrobial in 1986 for indoor use on hard surfaces. Use sites include agricultural premises, food establishments, medical facilities, and home bathrooms. Peracetic acid is also registered for use in dairy and cheese processing plants, on food processing equipment, and in pasteurizers in breweries, wineries, and beverage plants.[8] It is also applied for the disinfection of medical supplies, to prevent biofilm formation in pulp industries, and as a water purifier and disinfectant. Peracetic acid can be used as acooling tower water disinfectant, where it prevents biofilm formation and effectively controlsLegionella bacteria. Nu-Cidex is thetrade name for a brand of antimicrobial peracetic acid.[9]
In the European Union, peroxyacetic acid was reported by the EFSA after submission in 2013 by the US Department of Agriculture.[10]
Decontamination kits for cleaningfentanyl analogues from surfaces (as used by many police forces, amongst others) often contain solidperacetyl borate, which mixes with water to produce peracetic acid.[11]
Although less active than more acidic peracids (e.g.,m-CPBA), peracetic acid in various forms is used for theepoxidation of variousalkenes (Prilezhaev reaction). Useful applications are for unsaturated fats, synthetic and natural rubbers, and some natural products such aspinene. A variety of factors affect the amount of free acid or sulfuric acid (used to prepare the peracid).[12]
Peracetic acid is a strongoxidizing agent and severe irritant to the eyes, skin, and respiratory system. The U.S.Environmental Protection Agency published the followingAcute Exposure Guideline Levels (AEGL):[13]
| eight-hour TWA AEGL | Definition | mg/m3 | ppm |
|---|---|---|---|
| 1 | The concentration at which the general population will experience transient and reversible problems, such as notable discomfort, irritation, or certain asymptomatic non-sensory effects. | 0.52 | 0.17 |
| 2 | The concentration that results in irreversible or other serious, long-lasting adverse health effects or an impaired ability to escape. | 1.6 | 0.52 |
| 3 | The concentration that results in life-threatening health effects or death. | 4.1 | 1.3 |
