Peracetic acid (also known as peroxyacetic acid, or PAA) is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...
CH
3CO
3H. This
peroxy acid is a colorless liquid with a characteristic acrid odor reminiscent of
acetic acid
Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...
. It can be highly
corrosive
A corrosive substance is one that will damage or destroy other substances with which it comes into contact by means of a chemical reaction.
Etymology
The word ''corrosive'' is derived from the Latin verb ''corrodere'', which means ''to gnaw'', ...
.
Peracetic acid is a weaker acid than the parent acetic acid, with a
p''K''a of 8.2.
[
]
Production
Peracetic acid is produced industrially by the autoxidation of acetaldehyde
Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...
:
:O2 + CH3CHO → CH3CO3H
It forms upon treatment of acetic acid
Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...
with hydrogen peroxide
Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%†...
with a strong acid catalyst:
:H2O2 + CH3CO2H CH3CO3H + H2O
As an alternative, acetyl chloride
Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.
Synthesis
On a ...
and acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a col ...
can be used to generate a solution of the acid with lower water content.
Peracetic acid is generated ''in situ
''In situ'' (; often not italicized in English) is a Latin phrase that translates literally to "on site" or "in position." It can mean "locally", "on site", "on the premises", or "in place" to describe where an event takes place and is used in ...
'' by some laundry detergent
Laundry detergent is a type of detergent (cleaning agent) used for cleaning dirty laundry (clothes). Laundry detergent is manufactured in powder (washing powder) and liquid form.
While powdered and liquid detergents hold roughly equal share o ...
s. This is achieved by the action of bleach activator
Bleach activators are compounds that allow a lower washing temperature than would be required otherwise to achieve the full activity of bleaching agents in the wash liquor. Bleaching agents, usually peroxides, are usually sufficiently active only ...
s, such as tetraacetylethylenediamine
Tetraacetylethylenediamine, commonly abbreviated as TAED, is an organic compound with the chemical formula, 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 ...
and sodium nonanoyloxybenzenesulfonate
Sodium nonanoyloxybenzenesulfonate (NOBS) is an important component of laundry detergents and bleaches. It is known as a bleach activator for active oxygen sources, allowing formulas containing hydrogen peroxide releasing chemicals (specificall ...
, upon hydrogen peroxide formed from sodium percarbonate
Sodium percarbonate is a chemical substance with formula . It is an adduct of sodium carbonate ("soda ash" or "washing soda") and hydrogen peroxide (that is, a perhydrate) whose formula is more properly written as 2 · 3 . I ...
in water. The peracetic acid is a more effective bleaching agent
Bleach is the generic name for any chemical product that is used industrially or domestically to remove color (whitening) from a fabric or fiber or to clean or to remove stains in a process called bleaching. It often refers specifically, to ...
than hydrogen peroxide itself. PAA is also formed naturally in the environment through a series of photochemical reaction Organic photochemistry encompasses organic reactions that are induced by the action of light. The absorption of ultraviolet light by organic molecules often leads to reactions. In the earliest days, sunlight was employed, while in more modern times ...
s involving formaldehyde
Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...
and photo-oxidant radical
Radical may refer to:
Politics and ideology Politics
*Radical politics, the political intent of fundamental societal change
*Radicalism (historical), the Radical Movement that began in late 18th century Britain and spread to continental Europe and ...
s.
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.
Uses
The United States Environmental Protection Agency
The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it be ...
first registered peracetic acid as an antimicrobial
An antimicrobial is an agent that kills microorganisms or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ar ...
in 1985 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. 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
A cooling tower is a device that rejects waste heat to the atmosphere through the cooling of a coolant stream, usually a water stream to a lower temperature. Cooling towers may either use the evaporation of water to remove process heat and ...
water disinfectant, where it prevents biofilm formation and effectively controls ''Legionella
''Legionella'' is a genus of pathogenic gram-negative bacteria that includes the species '' L. pneumophila'', causing legionellosis (all illnesses caused by ''Legionella'') including a pneumonia-type illness called Legionnaires' disease and a mil ...
'' bacteria. A trade name
A trade name, trading name, or business name, is a pseudonym used by companies that do not operate under their registered company name. The term for this type of alternative name is a "fictitious" business name. Registering the fictitious name w ...
for peracetic acid as an antimicrobial is Nu-Cidex.
In the European Union, peroxyacetic acid was reported by the EFSA after submission in 2013 by the US Department of Agriculture .
Decontamination kits for cleaning fentanyl
Fentanyl, also spelled fentanil, is a very potent synthetic opioid used as a pain medication. Together with other drugs, fentanyl is used for anesthesia. It is also used illicitly as a recreational drug, sometimes mixed with heroin, cocaine ...
analogues from surfaces (as used by many police forces, amongst others) often contain solid peracetyl borate, which mixes with water to produce peracetic acid.
Epoxidation
Although less active than more acidic peracids (e.g., ''m''-CPBA), peracetic acid in various forms is used for the epoxidation
In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for ...
of various alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
s (Prilezhaev reaction
The Prilezhaev reaction, also known as the Prileschajew reaction or Prilezhaev epoxidation, is the chemical reaction of an alkene with a peroxy acid to form epoxides. It is named after Nikolai Prilezhaev, who first reported this reaction in 1909 ...
). Useful application are for unsaturated fats, synthetic and natural rubbers, and some natural products such as pinene
Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major comp ...
. A variety of factors affect the amount of free acid or sulfuric acid (used to prepare the peracid in the first place).
Safety
Peracetic acid is a strong oxidizing agent
An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or "Electron acceptor, accepts"/"receives" an electron from a (called the , , or ). In ot ...
and severe irritant to the skin, eyes, and respiratory system. The U.S. Environmental Protection Agency
A biophysical environment is a biotic and abiotic surrounding of an organism or population, and consequently includes the factors that have an influence in their survival, development, and evolution. A biophysical environment can vary in scale f ...
published the following Acute Exposure Guideline Levels Acute Exposure Guideline Levels (AEGLs) set levels of chemical concentration that pose a defined level of risk to humans (the general population, including susceptible individuals). These levels are used in preventing and responding to disasters. Th ...
(AEGL):
See also
*Disinfectant
A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than st ...
*Hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
*Organic peroxide
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 b ...
* Peroxy acid
*Trifluoroperacetic acid
Trifluoroperacetic acid (trifluoroperoxyacetic acid, TFPAA) is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula . It is a strong oxidizing agent for organic oxidation reactions, suc ...
References
{{Authority control
Bleaches
Disinfectants
Organic peroxy acids
Foul-smelling chemicals