Names | |||
---|---|---|---|
Preferred IUPAC name Ethaneperoxoic acid [1] | |||
Other names Peroxyacetic acid Acetic peroxide Acetyl hydroperoxide Proxitane | |||
Identifiers | |||
3D model (JSmol) | |||
Abbreviations | PAA | ||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.001.079 | ||
EC Number |
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KEGG | |||
PubChem CID | |||
RTECS number |
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UNII | |||
UN number | 3107 3105 | ||
CompTox Dashboard (EPA) | |||
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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 | 3.280 cP | ||
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 their standard state (at 25 °C [77 °F], 100 kPa). |
Peracetic acid (also known as peroxyacetic acid, or PAA) is an organic compound with the formula CH3CO3H. This peroxy acid is a colorless liquid with a characteristic acrid odor reminiscent of acetic acid. It can be highly corrosive.
Peracetic acid is a weaker acid than the parent acetic acid, with a pKa of 8.2. [2]
Peracetic acid is produced industrially by the autoxidation of acetaldehyde: [2]
In the presence of a strong acid catalyst, such as sulfuric acid, acetic acid and hydrogen peroxide produce peracetic acid: [3]
However, in concentrations (3-6%) of vinegar and hydrogen peroxide marketed for household use, mixing without a strong acid catalyst will not form peracetic acid.
As an alternative, acetyl chloride and acetic anhydride can be used to generate a solution of the acid with lower water content.
Peracetic acid is generated in situ by some laundry detergents. This is achieved by the action of bleach activators, such as tetraacetylethylenediamine and sodium nonanoyloxybenzenesulfonate, upon hydrogen peroxide formed from sodium percarbonate in water. The peracetic acid is a more effective bleaching agent than hydrogen peroxide itself. [4] [5] PAA is also formed naturally in the environment through a series of photochemical reactions involving formaldehyde and photo-oxidant radicals. [6]
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.
The United States Environmental Protection Agency first registered peracetic acid as an antimicrobial 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. [7] 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 a cooling tower water disinfectant, where it prevents biofilm formation and effectively controls Legionella bacteria. Nu-Cidex is the trade name for a brand of antimicrobial peracetic acid. [8]
In the European Union, peroxyacetic acid was reported by the EFSA after submission in 2013 by the US Department of Agriculture. [9]
Decontamination kits for cleaning fentanyl analogues from surfaces (as used by many police forces, amongst others) often contain solid peracetyl borate, which mixes with water to produce peracetic acid. [10]
Although less active than more acidic peracids (e.g., m-CPBA), peracetic acid in various forms is used for the epoxidation of various alkenes (Prilezhaev reaction). Useful applications are for unsaturated fats, synthetic and natural rubbers, and some natural products such as pinene. A variety of factors affect the amount of free acid or sulfuric acid (used to prepare the peracid). [11]
Peracetic acid is a strong oxidizing agent and severe irritant to the skin, eyes, and respiratory system. The U.S. Environmental Protection Agency published the following Acute Exposure Guideline Levels (AEGL): [12]
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 |
The cumene process is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene, the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR), and independently by Heinrich Hock in 1944.
In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.
In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.
Methyl ethyl ketone peroxide (MEKP) is an organic peroxide with the formula [(CH3)(C2H5)C(O2H)]2O2. MEKP is a colorless oily liquid. It is widely used in vulcanization (crosslinking) of polymers.
Hydrogen peroxide - urea is a white crystalline solid chemical compound composed of equal amounts of hydrogen peroxide and urea. It contains solid and water-free hydrogen peroxide, which offers a higher stability and better controllability than liquid hydrogen peroxide when used as an oxidizing agent. Often called carbamide peroxide in dentistry, it is used as a source of hydrogen peroxide when dissolved in water for bleaching, disinfection and oxidation.
A peroxy acid is an acid which contains an acidic –OOH group. The two main classes are those derived from conventional mineral acids, especially sulfuric acid, and the peroxy derivatives of organic carboxylic acids. They are generally strong oxidizers.
In organic chemistry, organic peroxides are organic compounds containing the peroxide functional group. If the R′ is hydrogen, the compounds are called hydroperoxides, which are discussed in that article. The O−O bond of peroxides easily breaks, producing free radicals of the form RO•. Thus, organic peroxides are useful as initiators for some types of polymerization, such as the acrylic, unsaturated polyester, and vinyl ester resins used in glass-reinforced plastics. MEKP and benzoyl peroxide are commonly used for this purpose. However, the same property also means that organic peroxides can explosively combust. Organic peroxides, like their inorganic counterparts, are often powerful bleaching agents.
Potassium peroxymonosulfate is widely used as an oxidizing agent, for example, in pools and spas. It is the potassium salt of peroxymonosulfuric acid. Usually potassium peroxymonosulfate is available as the triple salt 2KHSO5·KHSO4·K2SO4, known as Oxone.
Tetraacetylethylenediamine, commonly abbreviated as TAED, is an organic compound with the formula (CH3C(O))2NCH2CH2N(C(O)CH3)2. This white solid is commonly used as a bleach activator in laundry detergents and for paper pulp. It is produced by acetylation of ethylenediamine.
Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group. Hydroperoxide also refers to the hydroperoxide anion and its salts, and the neutral hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.
Epichlorohydrin is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.
In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains.
A phlegmatizer is a compound that minimizes the explosive tendency of compound or material. The term is derived from the word phlegmatic, meaning 'not easily excited'. Many chemical compounds that are potentially explosive have useful non-explosive applications. One large family of phlegmatizers are phthalate esters, which are used as solvents to minimize the explosive tendency of organic peroxides, such as dibenzoyl peroxide and MEKP, which are widely used initiators for polymerizations.
Pyridine-N-oxide is the heterocyclic compound with the formula C5H5NO. This colourless, hygroscopic solid is the product of the oxidation of pyridine. It was originally prepared using peroxyacids as the oxidising agent. The compound is used infrequently as an oxidizing reagent in organic synthesis.
Allyl acetate is an organic compound with formula C3H5OC(O)CH3. This colourless liquid is a precursor to especially allyl alcohol, which is a useful industrial intermediate. It is the acetate ester of allyl alcohol.
Diacetyl peroxide is the organic peroxide with the formula (CH3CO2)2. It is a white solid or oily liquid with a sharp odor. As with a number of organic peroxides, it is explosive. It is often used as a solution, e.g., in dimethyl phthalate.
Cycloheptanone, (CH2)6CO, is a cyclic ketone also referred to as suberone. It is a colourless volatile liquid. Cycloheptanone is used as a precursor for the synthesis of pharmaceuticals.
Lauroyl chloride is the organic compound with the formula CH3(CH2)10COCl. It is the acid chloride of lauric acid. Lauroyl chloride is a standard reagent for installing the lauroyl group. It is mainly produced as a precursor to dilauroyl peroxide, which is widely used in free-radical polymerizations.
in chemistry, sulfoxidation refers to two distinct reactions.
Dicumyl peroxide is an organic compound with the formula (C6H5CMe2O)2 (Me = CH3). Classified as a dialky peroxide, it is produced on a large scale industrially for use as an initiator for the production of low density polyethylene.