Trichloroacetic acid

Last updated
Trichloroacetic acid
Trichloroacetic acid structure.svg
Trichloroacetic-acid-3D-vdW.png
Trichloroacetic-acid-elpot.png
Names
Preferred IUPAC name
Trichloroacetic acid
Identifiers
3D model (JSmol)
970119
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.844 OOjs UI icon edit-ltr-progressive.svg
2842
KEGG
PubChem CID
RTECS number
  • AJ7875000
UNII
  • InChI=1S/C2HCl3O2/c3-2(4,5)1(6)7/h(H,6,7)
    Key: YNJBWRMUSHSURL-UHFFFAOYSA-N
  • ClC(Cl)(Cl)C(O)=O
Properties
C2HCl3O2
Molar mass 163.38 g·mol−1
AppearanceColorless to white, crystalline solid
Odor Sharp, pungent [1]
Density 1.63 g/cm3
Melting point 57 to 58 °C (135 to 136 °F; 330 to 331 K) [2]
Boiling point 196 to 197 °C (385 to 387 °F; 469 to 470 K) [2]
1000 g/100 mL [2]
Vapor pressure 1 mmHg (51.1 °C) [1]
Acidity (pKa)0.66 [3]
−73.0·10−6 cm3/mol
Structure
3.23 D
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-pollu.svg
Danger
H314, H410
P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Lethal dose or concentration (LD, LC):
5000 mg/kg orally in rats [2]
NIOSH (US health exposure limits):
PEL (Permissible)
None [1]
REL (Recommended)
TWA 1 ppm (7 mg/m3) [1]
IDLH (Immediate danger)
N.D. [1]
Related compounds
Chloroacetic acid
Dichloroacetic acid
Related compounds
 Acetic acid
Trifluoroacetic acid
Tribromoacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trichloroacetic acid (TCA; TCAA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. Salts and esters of trichloroacetic acid are called trichloroacetates.

Contents

Synthesis

Trichloroacetic acid was discovered by Jean-Baptiste Dumas in 1830. [4]

It is prepared by the reaction of chlorine with acetic acid in the presence of a suitable catalyst such as red phosphorus. This reaction is Hell–Volhard–Zelinsky halogenation.

CH
3COOH + 3 Cl
2 → CCl
3COOH + 3 HCl

Another route to trichloroacetic acid is the oxidation of trichloroacetaldehyde.

Use

It is widely used in biochemistry for the precipitation of macromolecules, such as proteins, DNA, and RNA. TCA and DCA are both used in cosmetic treatments (such as chemical peels and tattoo removal) and as topical medication for chemoablation of warts, including genital warts. It can kill normal cells as well. It is considered safe for use for this purpose during pregnancy. [5] [6]

The sodium salt (sodium trichloroacetate) was used as an herbicide starting in the 1950s but regulators removed it from the market in the late 1980s and early 1990s. [7] [8] [9] [10]

Environmental and health concerns

According to the European Chemicals Agency, "This substance causes severe skin burns and eye damage, is very toxic to aquatic life and has long lasting toxic effects." [11]

History

The discovery of trichloroacetic acid by Jean-Baptiste Dumas in 1839 delivered a striking example to the slowly evolving theory of organic radicals and valences. [12] The theory was contrary to the beliefs of Jöns Jakob Berzelius, starting a long dispute between Dumas and Berzelius. [13]

In the 1958 film The Blob , a bottle of trichloroacetic acid is tossed at the Blob in a futile attempt to fend it off.

See also

Related Research Articles

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Phosgene is an organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of carbonic acid, or structurally as formaldehyde with the hydrogen atoms replaced by chlorine atoms. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics.

The compound hydrogen chloride has the chemical formula HCl and as such is a hydrogen halide. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride gas and hydrochloric acid are important in technology and industry. Hydrochloric acid, the aqueous solution of hydrogen chloride, is also commonly given the formula HCl.

<span class="mw-page-title-main">1,4-Dichlorobenzene</span> Chemical compound

1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring.

<span class="mw-page-title-main">Jean-Baptiste Dumas</span> French chemist (1800–1884)

Jean Baptiste André Dumas was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights and molecular weights by measuring vapor densities. He also developed a method for the analysis of nitrogen in compounds.

<span class="mw-page-title-main">Parathion</span> Chemical compound

Parathion, also called parathion-ethyl or diethyl parathion and locally known as "Folidol", is an organophosphate insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms, including humans, so its use has been banned or restricted in most countries. The basic structure is shared by parathion methyl.

<span class="mw-page-title-main">Cyclohexanol</span> Chemical compound

Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Millions of tonnes are produced annually, mainly as a precursor to nylon.

In organic chemistry, the chloroacetic acids (systematic name chloroethanoic acids) are three related chlorocarbon carboxylic acids:

<span class="mw-page-title-main">Methylamine</span> Organic chemical compound

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Methyl acetate</span> Chemical compound

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

<span class="mw-page-title-main">Chlorobenzene</span> Aromatic organochlorine compound

Chlorobenzene is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

<span class="mw-page-title-main">Dimethylacetamide</span> Chemical compound

Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high-boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.

<span class="mw-page-title-main">Maleic anhydride</span> Chemical compound

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<span class="mw-page-title-main">Propyl acetate</span> Chemical compound

Propyl acetate, also known as propyl ethanoate, is an organic compound. Nearly 20,000 tons are produced annually for use as a solvent. This colorless liquid is known by its characteristic odor of pears. Due to this fact, it is commonly used in fragrances and as a flavor additive. It is formed by the esterification of acetic acid and propan-1-ol, often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

<span class="mw-page-title-main">Haloacetic acids</span>

Haloacetic acids are carboxylic acids in which a halogen atom takes the place of a hydrogen atom in acetic acid. In a monohaloacetic acid, a single halogen replaces a hydrogen atom; for example, in bromoacetic acid. Further substitution of hydrogen atoms with halogens can occur, as in dichloroacetic acid and trichloroacetic acid.

Perchloryl fluoride is a reactive gas with the chemical formula ClO
3F. It has a characteristic sweet odor that resembles gasoline and kerosene. It is toxic and is a powerful oxidizing and fluorinating agent. It is the acid fluoride of perchloric acid.

<span class="mw-page-title-main">Propargyl alcohol</span> Chemical compound

Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

Tetranitromethane or TNM is an organic oxidizer with chemical formula C(NO2)4. Its chemical structure consists of four nitro groups attached to one carbon atom. In 1857 it was first synthesised by the reaction of sodium cyanoacetamide with nitric acid.

References

  1. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards #0626 National Institute for Occupational Safety and Health (NIOSH)
  2. 1 2 3 4 Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN   0911910123
  3. ↑ Databog fysik kemi, F&K Forlaget 11. udgave 2009
  4. ↑ Terchloracetic Acid in Gmelin, L., Hand-book of Chemistry: Organic chemistry
  5. ↑ Jones, Kirtly (June 21, 2012). Marshall, Sarah (ed.). "Trichloroacetic Acid or Bichloroacetic Acid for Genital Warts (Human Papillomavirus)". WebMD. HealthWise. Archived from the original on 16 July 2015.
  6. ↑ Wiley DJ, Douglas J, Beutner K, Cox T, Fife K, Moscicki AB, Fukumoto L (2002). "External genital warts: Diagnosis, treatment, and prevention". Clinical Infectious Diseases. 35 (Suppl 2): S210–S224. doi: 10.1086/342109 . PMID   12353208.
  7. ↑ TCA-sodium in the Pesticide Properties DataBase (PPDB), accessed June 20, 2014
  8. ↑ G. S. Rai and C. L. Hamner. "Persistence of Sodium Trichloroacetate in Different Soil Types." Weeds 2(4) Oct. 1953: 271-279. JSTOR   4040104. DOI  10.2307/4040104.
  9. ↑ United Nations Environment Programme. "Trichloroacetic Acid CAS N°: 76-03-9" (OECD SIDS). Accessed June 20, 2014. Archived from the original on 15 August 2018.
  10. ↑ Heier, Al (December 1991). "Trichloroacetic Acid (TCA)". EPA. Accessed June 20, 2014 — via Cornell PMEP Pesticide Active Ingredient Information database. Archived from the original on 15 Aug 2020.
  11. ↑ "Trichloroacetic acid". C&L Inventory. European Chemical Agency . Retrieved 14 March 2022.
  12. ↑ Dumas (1839). "Trichloroacetic acid". Annalen der Pharmacie . 32: 101–119. doi:10.1002/jlac.18390320109.
  13. ↑ William Albert Noyes (1927). "Valence". Proceedings of the American Philosophical Society . 66: 287–308. JSTOR   3301070.
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