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Haloacetic acids

January 01, 1970

Haloacetic acids or HAAs are carboxylic acids in which one or more halogen atoms take the place of hydrogen atoms in the methyl group of acetic acid. Those acids have a general chemical formula X1X2X3C−CO2H, where X is hydrogen or halogen, and at least one X is a halogen. In a monohaloacetic acid (XCH2−CO2H), a single halogen replaces a hydrogen atom: for example, in bromoacetic acid (BrCH2−CO2H). Further substitution of hydrogen atoms with halogens can occur, as in dichloroacetic acid (Cl2CH−CO2H) and trichloroacetic acid (Cl3C−CO2H).

Bromoacetic acid
Trichloroacetic acid
Examples of haloacetic acids

Haloacetic acids are a common contaminant in treated drinking water, particularly water subjected to chlorination.

Contaminants in treated water edit

Haloacetic acids (HAAs) are a common undesirable by-product of water treatment by chlorination. Exposure to such disinfection by-products in drinking water, at high levels over many years, has been associated with a number of health outcomes by epidemiological studies.[1]

HAAs can be formed following chlorination, ozonation, or chloramination of water, as chlorine from the water disinfection process can react with organic matter and small amounts of bromide present in water.[2] HAAs are highly chemically stable, and therefore persist in water after formation.[3]

A study published in August 2006 found that total levels of HAAs in drinking water were not affected by storage or boiling, but that filtration was effective in decreasing levels.[4]

HAA5 edit

In the United States, the EPA regulates the five HAAs most commonly found in drinking water, collectively referred to as "HAA5."[2] These are:

The regulation limit for these five acids combined is 60 parts per billion (ppb).[5] The sum of bromodichloroacetic acid, dibromochloroacetic acid and tribromoacetic acid concentrations is known as HAA3.[6]

HAA9 edit

The designation "HAA9" refers to a larger group of HAAs, including all of the acids in HAA5, along with:

  • Bromochloroacetic acid (ClBrCH−CO2H)
  • Bromodichloroacetic acid (Cl2BrC−CO2H)
  • Dibromochloroacetic acid (ClBr2C−CO2H)
  • Tribromoacetic acid (Br3C−CO2H)

The level of these four acids in drinking water is not regulated by the EPA.[7][8] HAA6 refers to the sum of HAA5 and bromochloroacetic acid concentrations.[6]

Health effects edit

Haloacetic acids are readily absorbed by the human body after being ingested, and can be absorbed slightly through the skin. At high concentrations, HAAs have irritating and corrosive properties; however, typical concentrations of HAAs found in drinking water are extremely low. HAAs are typically eliminated from the body through normal processes between 1 day and 2 weeks after ingestion, depending on the type of acid.[2]

Highly concentrated HAAs have been found to cause toxicity in various organs, including the liver and pancreas, in animal studies. This includes an increased risk of cancer, particularly of the liver and bladder. For this reason, the EPA considers a few HAAs (namely DCA and TCA) as potential human carcinogens.[2] They may also cause developmental and reproductive problems during pregnancy.[9] However, short-term adverse health effects are unlikely after ingesting dilute quantities of HAAs,[2] and the long-term low-level risks associated with drinking treated water with residual HAAs are much lower than the risks of drinking untreated water.[10]

Chemical characteristics edit

The inductive effect caused by the electronegative halogens often results in the higher acidity of these compounds by stabilising the negative charge of the conjugate base.

See also edit

References edit

  1. ^ . cehtp.org. Archived from the original on 2019-04-08. Retrieved 2016-08-15.
  2. ^ a b c d e "Haloacetic Acids (five) (HAA5): Health Information Summary" (PDF). New Hampshire Department of Environmental Services. Retrieved 27 October 2023.
  3. ^ "Occurrence Assessment for the Final Stage 2 Disinfectants and Disinfection Byproducts Rule". United States Environmental Protection Agency. Retrieved 27 October 2023.
  4. ^ Levesque, S; Rodriguez, MJ; Serodes, J; Beaulieu, C; Proulx, F (2006). "Effects of indoor drinking water handling on trihalomethanes and haloacetic acids". Water Res. 40 (15): 2921–30. doi:10.1016/j.watres.2006.06.004. PMID 16889815.
  5. ^ "Disinfection Byproducts: A Reference Resource". United States Environmental Protection Agency. Retrieved 27 October 2023.
  6. ^ a b https://www.gov.nl.ca/ecc/waterres/drinkingwater/haa/
  7. ^ "Column Name: HAA9". United States Environmental Protection Agency. Retrieved 27 October 2023.
  8. ^ "Haloacetic acids (HAA9)". Environmental Working Group. Retrieved 27 October 2023.
  9. ^ "Haloacetic Acids in Public Water and Health". Iowa Public Health Tracking Portal. Iowa Department of Public Health. Retrieved 2023-10-27.
  10. ^ "Disinfection byproducts: HAA5". Minnesota Public Health Data Access. Minnesota Department of Health. Retrieved 2023-10-27.

Further reading edit

  • ANSI
  • National Institute of Health

External links edit

  • "Drinking Water Contaminants – Standards and Regulations". US Environmental Protection Agency.

January 01, 1970
haloacetic, acids, haas, carboxylic, acids, which, more, halogen, atoms, take, place, hydrogen, atoms, methyl, group, acetic, acid, those, acids, have, general, chemical, formula, x1x2x3c, co2h, where, hydrogen, halogen, least, halogen, monohaloacetic, acid, x. Haloacetic acids or HAAs are carboxylic acids in which one or more halogen atoms take the place of hydrogen atoms in the methyl group of acetic acid Those acids have a general chemical formula X1X2X3C CO2H where X is hydrogen or halogen and at least one X is a halogen In a monohaloacetic acid XCH2 CO2H a single halogen replaces a hydrogen atom for example in bromoacetic acid BrCH2 CO2H Further substitution of hydrogen atoms with halogens can occur as in dichloroacetic acid Cl2CH CO2H and trichloroacetic acid Cl3C CO2H Bromoacetic acidTrichloroacetic acidExamples of haloacetic acids Haloacetic acids are a common contaminant in treated drinking water particularly water subjected to chlorination Contents 1 Contaminants in treated water 1 1 HAA5 1 2 HAA9 2 Health effects 3 Chemical characteristics 4 See also 5 References 6 Further reading 7 External linksContaminants in treated water editHaloacetic acids HAAs are a common undesirable by product of water treatment by chlorination Exposure to such disinfection by products in drinking water at high levels over many years has been associated with a number of health outcomes by epidemiological studies 1 HAAs can be formed following chlorination ozonation or chloramination of water as chlorine from the water disinfection process can react with organic matter and small amounts of bromide present in water 2 HAAs are highly chemically stable and therefore persist in water after formation 3 A study published in August 2006 found that total levels of HAAs in drinking water were not affected by storage or boiling but that filtration was effective in decreasing levels 4 HAA5 edit In the United States the EPA regulates the five HAAs most commonly found in drinking water collectively referred to as HAA5 2 These are Chloroacetic acid ClCH2 CO2H Dichloroacetic acid Cl2CH CO2H Trichloroacetic acid Cl3C CO2H Bromoacetic acid BrCH2 CO2H Dibromoacetic acid Br2CH CO2H The regulation limit for these five acids combined is 60 parts per billion ppb 5 The sum of bromodichloroacetic acid dibromochloroacetic acid and tribromoacetic acid concentrations is known as HAA3 6 HAA9 edit The designation HAA9 refers to a larger group of HAAs including all of the acids in HAA5 along with Bromochloroacetic acid ClBrCH CO2H Bromodichloroacetic acid Cl2BrC CO2H Dibromochloroacetic acid ClBr2C CO2H Tribromoacetic acid Br3C CO2H The level of these four acids in drinking water is not regulated by the EPA 7 8 HAA6 refers to the sum of HAA5 and bromochloroacetic acid concentrations 6 Health effects editHaloacetic acids are readily absorbed by the human body after being ingested and can be absorbed slightly through the skin At high concentrations HAAs have irritating and corrosive properties however typical concentrations of HAAs found in drinking water are extremely low HAAs are typically eliminated from the body through normal processes between 1 day and 2 weeks after ingestion depending on the type of acid 2 Highly concentrated HAAs have been found to cause toxicity in various organs including the liver and pancreas in animal studies This includes an increased risk of cancer particularly of the liver and bladder For this reason the EPA considers a few HAAs namely DCA and TCA as potential human carcinogens 2 They may also cause developmental and reproductive problems during pregnancy 9 However short term adverse health effects are unlikely after ingesting dilute quantities of HAAs 2 and the long term low level risks associated with drinking treated water with residual HAAs are much lower than the risks of drinking untreated water 10 Chemical characteristics editThe inductive effect caused by the electronegative halogens often results in the higher acidity of these compounds by stabilising the negative charge of the conjugate base See also editFluoroacetic acid FCH2 CO2H Difluoroacetic acid F2CH CO2H Trifluoroacetic acid F3C CO2H Iodoacetic acid ICH2 CO2H Diiodoacetic acid I2CH CO2H Triiodoacetic acid I3C CO2H Bromodifluoroacetic acid F2BrCH CO2H References edit Drinking Water cehtp org Archived from the original on 2019 04 08 Retrieved 2016 08 15 a b c d e Haloacetic Acids five HAA5 Health Information Summary PDF New Hampshire Department of Environmental Services Retrieved 27 October 2023 Occurrence Assessment for the Final Stage 2 Disinfectants and Disinfection Byproducts Rule United States Environmental Protection Agency Retrieved 27 October 2023 Levesque S Rodriguez MJ Serodes J Beaulieu C Proulx F 2006 Effects of indoor drinking water handling on trihalomethanes and haloacetic acids Water Res 40 15 2921 30 doi 10 1016 j watres 2006 06 004 PMID 16889815 Disinfection Byproducts A Reference Resource United States Environmental Protection Agency Retrieved 27 October 2023 a b https www gov nl ca ecc waterres drinkingwater haa Column Name HAA9 United States Environmental Protection Agency Retrieved 27 October 2023 Haloacetic acids HAA9 Environmental Working Group Retrieved 27 October 2023 Haloacetic Acids in Public Water and Health Iowa Public Health Tracking Portal Iowa Department of Public Health Retrieved 2023 10 27 Disinfection byproducts HAA5 Minnesota Public Health Data Access Minnesota Department of Health Retrieved 2023 10 27 Further reading editANSI National Institute of HealthExternal links editHaloacetic Acids For Private Water and Health Regulated Public Water Supplies Drinking Water Contaminants Standards and Regulations US Environmental Protection Agency Retrieved from https en wikipedia org w index php title Haloacetic acids amp oldid 1219271754, wikipedia, wiki, book, books, library,

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