Trichloroacetic acid
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Names | |||
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Preferred IUPAC name
Trichloroacetic acid | |||
Identifiers | |||
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Properties | |||
C2HCl3O2 | |||
Molar mass | 163.38 g·mol−1 | ||
Appearance | Colorless 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] | ||
1000g/100mL[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 | |||
R-phrases (outdated) | Template:R35, Template:R50/53 | ||
S-phrases (outdated) | Template:S1/2, S26, Template:S36/37/39, Template:S45, Template:S60, Template:S61 | ||
NFPA 704 (fire diamond) | |||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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5000 mg/kg orally in rats[2] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[1] | ||
REL (Recommended)
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TWA 1 ppm (7 mg/m3)[1] | ||
IDLH (Immediate danger)
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N.D.[1] | ||
Related compounds | |||
Related chloroacetic acids
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Chloroacetic acid Dichloroacetic acid | ||
Related compounds
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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). | |||
verify (what is ?) | |||
Infobox references | |||
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as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms.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.
Synthesis
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.[4][5] 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.[6][7][8][9]
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Trichloracetic acid for TCA CROSS procedures
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Applying trichloracetic acid for TCA CROSS procedures
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Frosting after applying trichloracetic acid in TCA CROSS procedure
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.[10] The theory was contrary to the beliefs of Jöns Jakob Berzelius, starting a long dispute between Dumas and Berzelius.[11]
See also
References
- ↑ 1.0 1.1 1.2 1.3 1.4 NIOSH Pocket Guide to Chemical Hazards #0626National Institute for Occupational Safety and Health (NIOSH)
- ↑ 2.0 2.1 2.2 2.3 Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
- ↑ Databog fysik kemi, F&K Forlaget 11. udgave 2009
- ↑ "Trichloroacetic Acid or Bichloroacetic Acid for Genital Warts (Human Papillomavirus)". WebMD. Archived from the original on 2015-07-16. Retrieved 2021-04-27.
{{cite web}}
: More than one of|archivedate=
and|archive-date=
specified (help); More than one of|archiveurl=
and|archive-url=
specified (help) - ↑ 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.
- ↑ TCA-sodium in the Pesticide Properties DataBase (PPDB), accessed June 20, 2014
- ↑ G. S. Rai and C. L. Hamner Persistence of Sodium Trichloroacetate in Different Soil Types Archived 2020-07-20 at the Wayback Machine Weeds 2(4) Oct. 1953: 271-279
- ↑ OECD Trichloroacetic Acid CAS N°: 76-03-9 Archived 2016-03-04 at the Wayback Machine Accessed June 20, 2014
- ↑ EPA December 1991. trichloroacetic acid (TCA) EPA Cancellation 12/91 Archived 2020-08-15 at the Wayback Machine Accessed June 20, 2014
- ↑ Dumas (1839). "Trichloroacetic acid". Annalen der Pharmacie. 32: 101–119. doi:10.1002/jlac.18390320109. Archived (PDF) from the original on 2021-08-29. Retrieved 2021-04-27.
{{cite journal}}
: More than one of|accessdate=
and|access-date=
specified (help); More than one of|archivedate=
and|archive-date=
specified (help); More than one of|archiveurl=
and|archive-url=
specified (help) - ↑ William Albert Noyes (1927). "Valence". Proceedings of the American Philosophical Society. 66: 287–308. JSTOR 3301070.
External links
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- Acetic acids
- IARC Group 2B carcinogens
- Trichloromethyl compounds