Trichloroisocyanuric acid

Last updated
Trichloroisocyanuric acid
Trichloorisocyanuurzuur.png
Trichloroisocyanuric-acid-3D-balls.png
Symclosene Trichloroisocyanuric-acid-3D-spacefill.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-782-8
240759
KEGG
PubChem CID
RTECS number
  • XZ1925000
UNII
UN number 2468
  • InChI=1S/C3Cl3N3O3/c4-7-1(10)8(5)3(12)9(6)2(7)11 Yes check.svgY
    Key: YRIZYWQGELRKNT-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceColorless 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 solventsSoluble in chlorocarbons, acetone, and acetonitrile
Structure
planar
0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
lung irritant
GHS labelling:
GHS-pictogram-rondflam.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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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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.

Contents

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

Related Research Articles

<span class="mw-page-title-main">Chlorine</span> Chemical element, symbol Cl and atomic number 17

Chlorine is a chemical element; it has symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

<span class="mw-page-title-main">Sodium hypochlorite</span> Chemical compound (known in solution as bleach)

Sodium hypochlorite, commonly known in a dilute solution as (chlorine) bleach, is an inorganic chemical compound with the formula NaOCl, consisting of a sodium cation and a hypochlorite anion. It may also be viewed as the sodium salt of hypochlorous acid. The anhydrous compound is unstable and may decompose explosively. It can be crystallized as a pentahydrate NaOCl·5H
2
O
, a pale greenish-yellow solid which is not explosive and is stable if kept refrigerated.

<span class="mw-page-title-main">Disinfectant</span> Antimicrobial agent that inactivates or destroys microbes

A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than sterilization, which is an extreme physical or chemical process that kills all types of life. Disinfectants are generally distinguished from other antimicrobial agents such as antibiotics, which destroy microorganisms within the body, and antiseptics, which destroy microorganisms on living tissue. Disinfectants are also different from biocides—the latter are intended to destroy all forms of life, not just microorganisms. Disinfectants work by destroying the cell wall of microbes or interfering with their metabolism. It is also a form of decontamination, and can be defined as the process whereby physical or chemical methods are used to reduce the amount of pathogenic microorganisms on a surface.

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

Hypochlorous acid is an acid that forms when chlorine dissolves in water, and itself partially dissociates, forming hypochlorite, ClO. HClO and ClO are oxidizers, and the primary disinfection agents of chlorine solutions. HClO cannot be isolated from these solutions due to rapid equilibration with its precursor, chlorine.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

<span class="mw-page-title-main">Hypochlorite</span> Ion

In chemistry, hypochlorite, or chloroxide is an anion with the chemical formula ClO. It combines with a number of cations to form hypochlorite salts. Common examples include sodium hypochlorite and calcium hypochlorite. The Cl-O distance in ClO is 1.69 Å.

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

Nitrogen trichloride, also known as trichloramine, is the chemical compound with the formula NCl3. This yellow, oily, pungent-smelling and explosive liquid is most commonly encountered as a byproduct of chemical reactions between ammonia-derivatives and chlorine (for example, in swimming pools). Alongside monochloramine and dichloramine, trichloramine is responsible for the distinctive 'chlorine smell' associated with swimming pools, where the compound is readily formed as a product from hypochlorous acid reacting with ammonia and other nitrogenous substances in the water, such as urea from urine.

<span class="mw-page-title-main">Cyanuric acid</span> Chemical compound belonging to the class of triazine

Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleaches, disinfectants, and herbicides. In 1997, worldwide production was 160 000 tonnes.

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

Sodium chlorite (NaClO2) is a chemical compound used in the manufacturing of paper and as a disinfectant.

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

Cyanuric chloride is an organic compound with the formula (NCCl)3. This white solid is the chlorinated derivative of 1,3,5-triazine. It is the trimer of cyanogen chloride. Cyanuric chloride is the main precursor to the popular but controversial herbicide atrazine.

Calcium hypochlorite is an inorganic compound with formula Ca(ClO)2. It is a white solid, although commercial samples appear yellow. It strongly smells of chlorine, owing to its slow decomposition in moist air. This compound is relatively stable as a solid and solution and has greater available chlorine than sodium hypochlorite. "Pure" samples have 99.2% active chlorine. Given common industrial purity, an active chlorine content of 65-70% is typical. It is the main active ingredient of commercial products called bleaching powder, used for water treatment and as a bleaching agent.

1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

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">Sodium dichloroisocyanurate</span> Chemical compound

Sodium dichloroisocyanurate is a chemical compound widely used as a cleansing agent and disinfectant. It is a colorless, water-soluble solid, produced as a result of reaction of cyanuric acid with chlorine. The dihydrate is also known as is the potassium salt.

Monochloramine, often called chloramine, is the chemical compound with the formula NH2Cl. Together with dichloramine (NHCl2) and nitrogen trichloride (NCl3), it is one of the three chloramines of ammonia. It is a colorless liquid at its melting point of −66 °C (−87 °F), but it is usually handled as a dilute aqueous solution, in which form it is sometimes used as a disinfectant. Chloramine is too unstable to have its boiling point measured.

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

Rongalite is a chemical compound with the molecular formula Na+HOCH2SO2. This salt has many additional names, including Rongalit, sodium hydroxymethylsulfinate, sodium formaldehyde sulfoxylate, and Bruggolite. It is listed in the European Cosmetics Directive as sodium oxymethylene sulfoxylate (INCI). It is water-soluble and generally sold as the dihydrate. The compound and its derivatives are widely used in the dye industry. The structure of this salt has been confirmed by X-ray crystallography.

Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds. Two classes of compounds are considered: inorganic chloramines and organic chloramines.

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

Dichloroisocyanuric acid, also known as dichlor or dichloro-s-triazinetrione and is marketed under many names (e.g. troclosene), is a chemical compound with the formula (C(O)NCl)2(C(O)NH).

<span class="mw-page-title-main">Bleach</span> Chemicals used to whiten or disinfect

Bleach is the generic name for any chemical product that is used industrially or domestically to remove colour (whitening) from fabric or fiber or to clean or to remove stains in a process called bleaching. It often refers specifically to a dilute solution of sodium hypochlorite, also called "liquid bleach".

<span class="mw-page-title-main">Chlorine-releasing compounds</span>

Chlorine-releasing compounds, also known as chlorine base compounds, is jargon to describe certain chlorine-containing substances that are used as disinfectants and bleaches. They include the following chemicals: sodium hypochlorite, chloramine, halazone, and sodium dichloroisocyanurate. They are widely used to disinfect water and medical equipment, and surface areas as well as bleaching materials such as cloth. The presence of organic matter can make them less effective as disinfectants. They come as a liquid solution, or as a powder that is mixed with water before use.

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.