Trichloroisocyanuric acid

Trichloroisocyanuric acid is an organic compound with the formula (C3Cl3N3O3). It is used as an industrial disinfectant, bleaching agent and a reagent in organic synthesis.[1][2][3] This white crystalline powder, which has a strong "chlorine odour," is sometimes sold in tablet or granule form for domestic and industrial use.

Trichloroisocyanuric acid
Symclosene
Symclosene
Names
Preferred IUPAC name
1,3,5-Trichloro-1,3,5-triazinane-2,4,6-trione
Other names
  • Trichlor
  • Isocyanuric chloride
  • 1,3,5-Trichloro-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
  • Chloreal
  • Symclosene
  • Trichloro-s-triazinetrione
  • TCICA
  • TCCA
Identifiers
3D model (JSmol)
202022
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.621
EC Number
  • 201-782-8
240759
KEGG
RTECS number
  • XZ1925000
UNII
UN number 2468
  • InChI=1S/C3Cl3N3O3/c4-7-1(10)8(5)3(12)9(6)2(7)11 checkY
    Key: YRIZYWQGELRKNT-UHFFFAOYSA-N checkY
  • InChI=1/C3Cl3N3O3/c4-7-1(10)8(5)3(12)9(6)2(7)11
    Key: YRIZYWQGELRKNT-UHFFFAOYAR
  • ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O
Properties
C3Cl3N3O3
Molar mass 232.40 g·mol−1
Appearance Colorless solid
Density 2.19 ± 0.1 g/cm3
Melting point 246 to 247 °C (475 to 477 °F; 519 to 520 K)
Boiling point decomposes
1.2%
Solubility in other solvents Soluble in chlorocarbons, acetone, and acetonitrile
Structure
planar
0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 lung irritant
GHS labelling:
GHS03: OxidizingGHS07: Exclamation markGHS09: Environmental hazard
Warning
H272, H302, H319, H335, H410
P210, P220, P221, P261, P264, P270, P271, P273, P280, P301+P312, P304+P340, P305+P351+P338, P312, P330, P337+P313, P370+P378, P391, P403+P233, P405, P501
Flash point NA
Related compounds
Related compounds
 Cyanuric chloride
Dichloroisocyanuric acid
Tribromoisocyanuric 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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Infobox references

Synthesis

Trichloroisocyanuric acid is prepared from cyanuric acid via a reaction with chlorine gas and trisodium cyanurate.[4]

Applications

The compound is a disinfectant, algicide and bactericide mainly for swimming pools and dyestuffs, and is also used as a bleaching agent in the textile industry. It is widely used in civil sanitation for pools and spas, preventing and curing diseases in animal husbandry and fisheries, fruit and vegetable preservation, wastewater treatment, as an algicide for recycled water in industry and air conditioning, in anti shrink treatment for woolens, for treating seeds and in organic chemical synthesis. It is used in chemical synthesis as an easy to store and transport chlorine gas source, it is not subject to hazardous gas shipping restrictions, and its reaction with hydrochloric acid produces relatively pure chlorine.[5]

Trichloroisocyanuric acid as used in swimming pools is easier to handle than chlorine gas. It dissolves slowly in water, but as it reacts, cyanuric acid concentration in the pool will build-up.

See also

References
  1. Hiegel, G. A. (2001). "Trichloroisocyanuric Acid". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.rt209. ISBN 0471936235.
  2. Barros, J. C. (2005). "Trichloroisocyanuric acid". Synlett. 2005 (13): 2115–2116. doi:10.1055/s-2005-872237.
  3. Tilstam, Ulf; Weinmann, Hilmar (July 2002). "Trichloroisocyanuric Acid: A Safe and Efficient Oxidant". Organic Process Research & Development. 6 (4): 384–393. doi:10.1021/op010103h.
  4. Chattaway, F. D.; Wadmore, J. Mello (1902). "XX.—The constitution of hydrocyanic, cyanic, and cyanuric acids". J. Chem. Soc., Trans. 81: 191–203. doi:10.1039/CT9028100191.
  5. L. Lerner (2011). "Chlorine". Small-Scale Synthesis of Laboratory Reagents with Reaction Modeling. CRC Press. ISBN 9780367383046.
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