Trichloroisocyanuric acid
{{chembox
| Watchedfields = changed
| verifiedrevid = 470613519
| Name = Trichloroisocyanuric acid
| ImageFile1 = Trichloorisocyanuurzuur.png
| ImageSize1 = 150px
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = Trichloroisocyanuric-acid-3D-balls.png
| ImageFileR1 = Trichloroisocyanuric-acid-3D-spacefill.png
| ImageNameR1 = Symclosene
| PIN = 1,3,5-Trichloro-1,3,5-triazinane-2,4,6-trione
| OtherNames = {{unbulleted list|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}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 87-90-1
| Beilstein = 202022
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 33015
| ChEMBL = 1698868
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6643
| EC_number = 201-782-8
| Gmelin = 240759
| KEGG = D05985
| PubChem = 6909
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = RL3HK1I66B
| UNNumber = 2468
| RTECS = XZ1925000
| SMILES = ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O
| InChI = 1/C3Cl3N3O3/c4-7-1(10)8(5)3(12)9(6)2(7)11
| InChIKey = YRIZYWQGELRKNT-UHFFFAOYAR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3Cl3N3O3/c4-7-1(10)8(5)3(12)9(6)2(7)11
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YRIZYWQGELRKNT-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=3 | Cl=3 | N=3 | O=3
| Appearance = Colorless solid
| Density = 2.19 ± 0.1 g/cm3
| Solubility = 1.2%
| Solvent = other solvents
| SolubleOther = Soluble in chlorocarbons, acetone, and acetonitrile
| MeltingPtC = 246 to 247
| BoilingPt = decomposes
}}
|Section3={{Chembox Structure
| Coordination = planar
| CrystalStruct =
| Dipole = 0 D
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards = lung irritant
| FlashPt = NA
| GHSPictograms = {{GHS03}}{{GHS07}}{{GHS09}}{{GHS05}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|272|302|314|319|335|410}}
| PPhrases = {{P-phrases|210|220|260|261|264|264+265|270|271|273|280|301+317|301+330+331|302+361+354|304+340|305+351+338|316|319|321|330|337+317|363|370+378|391|403+233|405|501}}
}}
|Section8={{Chembox Related
| OtherCompounds = Cyanuric chloride
Dichloroisocyanuric acid
Tribromoisocyanuric acid
}}
}}
Trichloroisocyanuric acid is an organic compound with the formula (CONCl)3. It is used as an industrial disinfectant, bleaching agent and a reagent in organic synthesis.{{ cite encyclopedia | author = Hiegel, G. A. | chapter = Trichloroisocyanuric Acid | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | year = 2001 | publisher = John Wiley & Sons | location = New York | doi = 10.1002/047084289X.rt209 | isbn = 0471936235 }}{{ cite journal | author = Barros, J. C. | title = Trichloroisocyanuric acid | journal = Synlett | year = 2005 | volume = 2005 | issue = 13 | pages = 2115–2116 | doi = 10.1055/s-2005-872237 | doi-access = free }}{{cite journal|last1=Tilstam|first1=Ulf|last2=Weinmann|first2=Hilmar|title=Trichloroisocyanuric Acid: A Safe and Efficient Oxidant|journal=Organic Process Research & Development|date=July 2002|volume=6|issue=4|pages=384–393|doi=10.1021/op010103h}} This white crystalline powder, which has a strong "chlorine odour," is sometimes sold in tablet or granule form for domestic and industrial use.
Synthesis
Trichloroisocyanuric acid is prepared from cyanuric acid via a reaction with chlorine gas and trisodium cyanurate.{{cite journal|last1=Chattaway|first1=F. D.|last2=Wadmore|first2=J. Mello|title=XX.—The constitution of hydrocyanic, cyanic, and cyanuric acids|journal=J. Chem. Soc., Trans.|date=1902|volume=81|pages=191–203|doi=10.1039/CT9028100191|url=https://zenodo.org/record/2128442}}
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.{{ cite book | author = L. Lerner | title = Small-Scale Synthesis of Laboratory Reagents with Reaction Modeling | chapter = Chlorine | year = 2011 | publisher = CRC Press | isbn = 9780367383046 }}
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. In large bodies of water, the TCCA is soluble and breaks down slowly, releasing chlorine in the water to sanitize contaminants. When TCCA instead comes in contact with or is wetted/moistened by a small amount of water and does not dissolve, it can experience a chemical reaction, generating heat and causing the decomposition of the chemical, which in turn produces toxic chlorine gas and can produce explosive nitrogen trichloride. {{cite book |title=Trichloroisocyanuric Acid Reaction, Decomposition, and Toxic Gas Release at Bio-Lab, Inc., Westlake, LA, Incident Date: August 27, 2020, Report No. 2020-05-I-LA |publisher=U.S. Chemical Safety and Hazard Investigation Board | year = 2023 |ref=No. 2020-05-I-LA |url=https://www.csb.gov/bio-lab-lake-charles-chemical-fire-and-release-/}}
See also
References
{{reflist}}
External links
- [https://pubchem.ncbi.nlm.nih.gov/compound/6909 Symclosene data page]
- [http://msds.orica.com/pdf/shess-en-cds-010-000031021401.pdf MSDS for Trichloroisocyanuric acid]
- [http://derpharmachemica.com/vol8-iss4/DPC-2016-8-4-286-290.pdf Oxidation of primary alcohol to aldehyde]
{{DEFAULTSORT:Trichloroisocyanuric Acid}}