Trichlorisocyanursäure

Trichloroisocyanuric Acid

HCID 6909CAS 87-90-1

Grundinformationen

Standard-SMILES
O=c1n(Cl)c(=O)n(Cl)c(=O)n1Cl
InChIKey
YRIZYWQGELRKNT-UHFFFAOYSA-N
Summenformel
C3Cl3N3O3
Durchschnittliche Molmasse
232,41 g/mol
Monoisotopische Masse
230,9005239

Überblick

Trichloro-s-triazinetrione, dry appears as a white slightly hygroscopic crystalline powder or lump solid with a mild chlorine-like odor. Said to have 85 percent available chlorine. Decomposes at 225 °C. Moderately toxic by ingestion. May irritate skin and eyes. Active ingredient in household dry bleaches. Used in swimming pools as a disinfectant.

Namen und Bezeichner

Bevorzugter Name
Trichloroisocyanuric Acid
IUPAC
1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione
Lokaler Name
Trichlorisocyanursäure
Englischer Name
Trichloroisocyanuric acid
Summenformel
C3Cl3N3O3
Molmasse
232.41

Namen und Synonyme

TRICHLOROISOCYANURIC ACIDSymclosene87-90-1Trichlorocyanuric acidSymclosenChlorealTrichloro-s-triazinetrioneFi Clor 91Fichlor 91Isocyanuric chlorideTrichloroisocyanic acidNeochlor 90
Weitere Namen anzeigen
TCCATCICABLEACH1,3,5-Trichloro-1,3,5-triazinane-2,4,6-trionetrichloroisocyanuric1,3,5-TRICHLORO-2,4,6-TRIAZINETRIONE
1,3,5-Trichloroisocyanuric acidACL 85SinclosenoNSC-405124Trichloroiminocyanuric acidSymclosenumKyselina trichloisokyanurovaTrichlorisocyanursaeure

Datenbank-Bezeichner

CAS
87-90-1
PubChem CID
6909
DTXSID
DTXSID2026523
ChEMBL
CHEMBL1698868
ChEBI
CHEBI:33015
UNII
RL3HK1I66B
EC Number
201-782-8
Nikkaji
J4.283H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,2
Polarare Oberfläche (TPSA)
60,9 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
0
Schwere Atome
12

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Uses -> Biocides/Disinfectants

Reactive agents - 2nd degree

pHpH = 4.4
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP0.26
OdorChlorine odor
Density · 4 Einträge

greater than 1 at 68 °F (est) (USCG, 1999)

Greater than 1 at 20 °C (solid)

2.07 g/cm³

> 1

Physikochemische Eigenschaften

Schmelzpunkt
249 · 249-251 °C (lit.)
Siedepunkt
272.3 · 272.3±23.0 °C(Predicted)
Dichte
2.07 · 2.07
Dampfdruck
0.001 · 0.001-0.002Pa at 20-25℃
Flammpunkt
121 °C · 121°C
storage temp.
30 °C · Store below +30°C.

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H272: May intensify fire; oxidizer [Danger Oxidizing liquids; Oxidizing solids]

P210, P220, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P304+P340, P305+P351+P338, P319, P330, P337+P317, P370+P378, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H272 (100%): May intensify fire; oxidizer [Danger Oxidizing liquids; Oxidizing solids]

P210, P220, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P330, P337+P317, P363, P370+P378, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-trichloro-

1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-trichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-trichloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 15-08-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24502

1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-trichloro-: HSNO Approval: HSR001359 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-trichloro-: Human health tier II assessment
DOT LabelOxidizer
Fire Hazards · 3 Einträge

Special Hazards of Combustion Products: Toxic chlorine or nitrogen trichloride may be formed in fires.

CAUTION: Ammonium nitrate products may explode if involved in fire or contaminated with hydrocarbons (fuels), organic matter, other contaminants or when hot molten and contained. Treat as an explosive (GUIDE 112).

Not combustible but enhances combustion of other substances. Gives off irritating or toxic fumes (or gases) in a fire. Risk of explosion on heating. Risk of explosion on contact with combustible substances or incompatible substances. See Chemical Dangers.

Fire Potential · 2 Einträge

Noncombustible, but due to high reactivity (chlorination, oxidation), may cause ignition by contact with many substances, organic substances easily chlorinated or oxidizeD.

Not combustible. Reacts with combustible materials, ammonium salts, or foreign substances, resulting in fire.

Health Hazards · 2 Einträge

Inhalation causes sneezing and coughing. Contact with dust causes moderate irritation of eyes and itching and redness of skin. Ingestion causes burns of mouth and stomach. (USCG, 1999)

· Inhalation, ingestion or contact (skin, eyes) with vapors or substance may cause severe injury, burns or death.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fire Extinguishing Agents: Water in large amounts (USCG, 1999)

Use water in large amounts, foam, dry powder. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.

First Aid Measures · 4 Einträge

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Keep combustibles (wood, paper, oil, etc.) away from spilled material.

First Aid · 2 Einträge

INHALATION: remove victim to fresh air.

General First Aid:

Safe StorageDry. Well closed. Separated from amines, combustible substances and reducing agents. See Chemical Dangers. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Firefighting HazardsClosed containers may rupture violently when heated. Thermally unstable. Decomposes at 437 °F (225 °C).

Toxikologische Informationen

InteractionsHalogenated isocyanurates exhibit biocidal synergism when used with 3-isothiazolone derivatives.
Ecotoxicity Values · 5 Einträge

LC50; Species: Anas platyrhynchos (Mallard duck, age 14 days) diet >10000 ppm for 8 days

LC50; Species: Anas platyrhynchos (Mallard duck) diet >5000 ppm for 8 days

LC50; Species: Anas platyrhynchos (Mallard duck, age 9 days) diet >5620 ppm for 8 days

LD50; Species: Anas platyrhynchos (Mallard duck, age 14 days) oral via capsule 1890 mg/kg

For more Ecotoxicity Values (Complete) data for Trichloroisocyanuric acid (21 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 25(SRC), determined from a water solubility of 1.2X10+4 mg/L(2) and a regression-derived equation(3), indicates that trichloroisocyanuric acid is expected to have very high mobility in soil(SRC). Volatilization of trichloroisocyanuric acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.2X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Trichloroisocyanuric acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data for trichloroisocyanuric acid in the terrestrial environment were not available(SRC,2009). However, in the Japanese MITI test, trichloroisocyanuric acid reacted with water to form isocyanuric acid, which is confirmed to be biodegradable(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 25(SRC), determined from a water solubility of 1.2X10+4 mg/L(2) and a regression-derived equation(3), indicates that trichloroisocyanuric acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 6.2X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 3.1(SRC), from its water solublity(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Trichloroisocyanuric acid is expected to undergo hydrolysis in the environment since this compound contains functional groups that hydrolyze under environmental conditions(4). Biodegradation data for trichloroisocyanuric acid in the aquatic environment were not available(SRC,2009). However, in the Japanese MITI test, trichloroisocyanuric acid reacted with water to form isocyanuric acid, which is confirmed to be biodegradable(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trichloroisocyanuric acid, which has an estimated vapor pressure of 1.6X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase trichloroisocyanuric acid may be removed from the air by wet or dry deposition(SRC). Trichloroisocyanuric acid does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body in hazardous amounts by inhalation and by ingestion.
Ecotoxicity Excerpts · 2 Einträge

/AQUATIC SPECIES/ The effects of trichloroisocyanuric acid (TCCA) ... on the freshwater alga Chlorella vulgaris were assessed by toxicity bioassays and by the values of biomarkers in phase I and phase II. The biomarkers included growth rate, concentration of chlorophyll a, activities of 7-ethoxyresorufin-O-dealkylases (EROD), glutathione S-transferase (GST), catalase (CAT), and total glutathione (GSH) ... Trichloroisocyanuric acid was a strong growth inhibitor and, at concentrations of greater than 0.80 mg/L, caused 100% inhibition on 24-hr exposure. The 96-hr EC50 of TCCA was 0.313 mg/L ... In TCCA exposure, GST activity was significantly stimulated, and GSH concentration was increased. Catalase activity increased only at TCCA concentrations of greater than 0.12 mg/L, and no change in EROD activity was observed.

/AQUATIC SPECIES/ This paper reports the acute toxicity of three biocides used in the disinfection of cooling towers, tetrakis(hydroxymethyl) phosphonium chloride (THPC), trichloroisocyanuric acid (TCIC), and sodium bromide (NaBr), on Artemia larvae, their effect on the phototactic response of this organism, and the potential of bioaccumulation in this species. The 24-hr median lethal concentration (LC50) values for these biocides with respect to 24-, 48-, and 72-hr-old Artemia, determined by static bioassays, showed the following rank order of toxicity: THPC < TCIC < NaBr. An age-dependent increase in sensitivity was seen for each compound. All three biocides reduced the phototactic response of 24-hr-old Artemia larvae in 24-hr static bioassays; the median inhibitory concentration ratios obtained were 30 to 40 times lower than their respective 24-hr LC50 values. The results suggest that phototaxis bioassays could provide the speed and simplicity required for screening many potential pollutants for harmful effects. The bioconcentration factors obtained for Artemia larvae exposed to 10% LC50 for 168 hr in renewal assays were 93.75, 1.67, and 0.23 for THPC, TCIC, and NaBr, respectively. This shows these biocides pose no bioaccumulation risk in this organism, although the value of 93.75 obtained for THPC is close to the threshold above which such a risk is considered to exist.

Regulatorische Informationen

FIFRA Requirements · 3 Einträge

Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. ... (c) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-processing equipment and utensils. 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-trichloro- is included on this list. Limit: When ready for use, the end-use concentration of all di- or trichloroisocyanuric acid chemicals in the solution is not to exceed 100 ppm determined as total available chlorine.

The Agency has sufficient information on the health effects of the chlorinated isocyanurates and on their potential for causing adverse effects in fish and wildlife and the environment for all uses registered for these chemicals. The Agency therefore concludes that products containing the chlorinated isocyanurates for these uses are eligible for reregistration. Only product chemistry data on certain manufacturing use products are still needed. The Agency has determined that the chlorinated isocyanurate products, labeled and used as specified in this Reregistration Eligibility Document, will not pose unreasonable risks or adverse effects to humans or the environment.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Sodium dichloroisocyanurate is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0569; Pesticide type: antimicrobial; Registration Standard Date: 5/20/88 PB88-220660; Case Status: RED Approved 09/02; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): trichloroisocyanuric acid; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
UN 2468 (TRICHLOROISOCYANURIC ACID, DRY)
hs_code
29336980
RTECS-Nr.
XZ1925000
risk_code
8-22-31-36/37-50/53-36/37/38

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Both s-triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-trichloro- and s-triazine-2,4,6(1H,3H,5H)-trione, 1,3-dichloro-, sodium salt are unstable in the body (particularly the stomach) because the available chlorine is rapidly reduced. Cyanuric acid (or its monosodium salt) is the degradation product from both products.

Verwendung und Herstellung

Uses · 6 Einträge

Used in swimming pool sanitizers, industrial deodorants, bleaches, scouring powders, and dishwashing compounds; [HSDB] Used as a disinfectant, chlorinating agent, stainless steel cleaner, and non-shrink agent for wool; [Merck Index]

Metal Degreasing [Category: Clean]

For trichloroisocyanuric acid (USEPA/OPP Pesticide Code: 081405) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Fumigant

Microbicide/microbistat (slime forming bacteria, fungi, algae), disinfectant, sanitizer, fungicide, algicide, bacteriostat.

Chlorinating agent, disinfectant, industrial deodorant. In household cleansers. In removing oil and protein in stainless steel. In non-shrink treatment for wool. Oxidant and chlorinating reagent in organic synthesis.

U.S. Exports(1974) 6.36X10+9 grams (Dichloro & Trichloro & Salts)
U.S. Production · 6 Einträge

2023: 2,500,000 - <4,000,000 lb

(1972) 2.87X10+10 grams (di & tri & salts)

(1974) 3.63X10+10 g /Chlorinated isocyanurates/

1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-trichloro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2340]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-trichloro-. Aggreated National Production Volume: 500,000 to < 1 million lbs.

Consumption Patterns · 1 Eintrag

(For all chlorinated isocyanurates-trichloroisocyanuric acid, sodium dichloroisocyanurate, and potassium dichloroisocyanurate) 53% as swimming pool sanitizer; 19.6% in commercial bleach; 7.6% in household bleach; 7.6% in dishwasher compounds; 6.1% in scouring powders; 6.1% in chlorinated cleaners and sanitizers (1974)

Consumer UsesBleaching agent
Industry UsesNot Known or Reasonably Ascertainable
Anwendungen · 2 Einträge

BeschreibungTrichlorisocyanursäure bildet farblose Kristalle; aus Dichlorethan kristallisiert, bildet es Nadeln mit einem Schmelzpunkt von 246-247 ℃ (1) (Zersetzung) bzw. 249-251 ℃ (2). Bei Kontakt mit Wasser tritt unter Freigabe von Hypochloriger Säure Zersetzung in Cyanursäure auf. In Wasser ist es schlecht, (0.2% bei 25 ℃) in organischen Lösemitteln allgemein gut löslich. Es findet Anwendung als Bleichmittel für Textilien, in Scheuer- und Reinigungsmitteln sowie zur Desinfektion von Schwimmbecken. Zudem ist es ein vielseitiges Chlorierungs- und Oxidationsreagenz in der organischen Chemie. Es kann zur Umwandlung von primären Alkoholen zu Methylestern, und Diolen zu Lactonen eingesetzt werden (3). Eine gute Übersicht über die Synthesemöglichkeiten mit Trichlorisocyanursäure zeigt Organic Process Research & Development 2002, 6, 384-393. Des Weiteren ist es für die Chlorgasgenerierung mit Salzsäure geeignet (gegen Schwefelsäure ist es hingegen innert).

VerwendenTrichloroisocyanuric Acid is a disinfectant and anti-bacterial. It can also be used in the synthesis of napthols.

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