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EC number: 201-782-8 | CAS number: 87-90-1
- Life Cycle description
- Uses advised against
- Endpoint summary
- Appearance / physical state / colour
- Melting point / freezing point
- Boiling point
- Density
- Particle size distribution (Granulometry)
- Vapour pressure
- Partition coefficient
- Water solubility
- Solubility in organic solvents / fat solubility
- Surface tension
- Flash point
- Auto flammability
- Flammability
- Explosiveness
- Oxidising properties
- Oxidation reduction potential
- Stability in organic solvents and identity of relevant degradation products
- Storage stability and reactivity towards container material
- Stability: thermal, sunlight, metals
- pH
- Dissociation constant
- Viscosity
- Additional physico-chemical information
- Additional physico-chemical properties of nanomaterials
- Nanomaterial agglomeration / aggregation
- Nanomaterial crystalline phase
- Nanomaterial crystallite and grain size
- Nanomaterial aspect ratio / shape
- Nanomaterial specific surface area
- Nanomaterial Zeta potential
- Nanomaterial surface chemistry
- Nanomaterial dustiness
- Nanomaterial porosity
- Nanomaterial pour density
- Nanomaterial photocatalytic activity
- Nanomaterial radical formation potential
- Nanomaterial catalytic activity
- Endpoint summary
- Stability
- Biodegradation
- Bioaccumulation
- Transport and distribution
- Environmental data
- Additional information on environmental fate and behaviour
- Ecotoxicological Summary
- Aquatic toxicity
- Endpoint summary
- Short-term toxicity to fish
- Long-term toxicity to fish
- Short-term toxicity to aquatic invertebrates
- Long-term toxicity to aquatic invertebrates
- Toxicity to aquatic algae and cyanobacteria
- Toxicity to aquatic plants other than algae
- Toxicity to microorganisms
- Endocrine disrupter testing in aquatic vertebrates – in vivo
- Toxicity to other aquatic organisms
- Sediment toxicity
- Terrestrial toxicity
- Biological effects monitoring
- Biotransformation and kinetics
- Additional ecotoxological information
- Toxicological Summary
- Toxicokinetics, metabolism and distribution
- Acute Toxicity
- Irritation / corrosion
- Sensitisation
- Repeated dose toxicity
- Genetic toxicity
- Carcinogenicity
- Toxicity to reproduction
- Specific investigations
- Exposure related observations in humans
- Toxic effects on livestock and pets
- Additional toxicological data

Stability in organic solvents and identity of relevant degradation products
Administrative data
Link to relevant study record(s)
- Endpoint:
- stability in organic solvents and identity of relevant degradation products
- Type of information:
- experimental study
- Adequacy of study:
- weight of evidence
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- other: A well documented patent which is considered scientifically acceptable. The patent describes a process which demonstrates that TCCA is stable in cyclohexanone.
- Principles of method if other than guideline:
- The patent describes applying solutions of TCCA in various solvents that are used for bonding vulcanised rubber surfaces and thus provides data on stablity of TCCA in an organic solvent which is used in this process.
- Test substance stable:
- yes
- Conclusions:
- TCCA is stable in aliphatic ketones such as cyclohexanone.
- Endpoint:
- stability in organic solvents and identity of relevant degradation products
- Type of information:
- experimental study
- Adequacy of study:
- weight of evidence
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- other: A well documented patent which is considered scientifically acceptable. The patent describes a process which demonstrates the stability of TCCA in a variety of organic solvents.
- Principles of method if other than guideline:
- Solutions of TCCA in various solvents are used for attachment of elastomeric shoe sole material to shoe upper material such as leather.
- Test substance stable:
- yes
- Conclusions:
- TCCA is stable in mixtures of 1,1,1-trichloroethane, t-butanol, and toluene for as long as one year.
- Endpoint:
- stability in organic solvents and identity of relevant degradation products
- Type of information:
- experimental study
- Adequacy of study:
- weight of evidence
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- other: Well documented paper which meets basic scientific principles.
- Principles of method if other than guideline:
- The experiment describes a procedure whereby trichloroisocyanuric acid (TCCA) is reacted with aliphatic cyclic ethers such as tetrahydrofuran and tetrahydropyran and thus provides information on the stability of TCCA in these compounds
- Test substance stable:
- no
- Conclusions:
- TCCA reacts exothermically at room temperature with aliphatic cyclic ethers such as tetrahydrofuran and tetrahydropyran.
- Endpoint:
- stability in organic solvents and identity of relevant degradation products
- Type of information:
- experimental study
- Adequacy of study:
- weight of evidence
- Reliability:
- 4 (not assignable)
- Rationale for reliability incl. deficiencies:
- other: Literature review of trichloroisocyanuric acid. Includes some information on TCCA reactions whereby organic solvents have been used.
- Principles of method if other than guideline:
- Reactions involving TCCA as a reagent are reviewed. Reactions with a wide variety of compounds are described.
- Test substance stable:
- yes
- Conclusions:
- TCCA is stable in carbon tetrachloride, methylene chloride, dimethylformamide, acetonitrile, toluene, acetone, acetic acid. TCCA reacts with organic sulfides, pyrazolines, primary alcohols and diols, primary lactones, secondary alcohols, amides, lactams and carbamates, alkenes, alkynes, α-amino-acids.
- Endpoint:
- stability in organic solvents and identity of relevant degradation products
- Type of information:
- experimental study
- Adequacy of study:
- weight of evidence
- Reliability:
- 4 (not assignable)
- Rationale for reliability incl. deficiencies:
- other: Literature review of trichloroisocyanuric acid. Includes some information on TCCA reactions whereby organic solvents have been used.
- Principles of method if other than guideline:
- The literature on trichloroisocyanuric acid has been reviewed. The review includes information on reactions involving TCCA as a reagent with organic solvents.
- Test substance stable:
- ambiguous
- Remarks:
- The report lists a number of solvents in which TCCA is stable and also a number of solvents with which it reacts (see below).
- Conclusions:
- TCCA is stable in carbon tetrachloride, chloroform, methylene chloride, dimethylformamide, ethyl acetate, acetonitrile, acetone, toluene and acetic acid.
TCCA reacts with alkenes, alkyl N-heterocycles such as alkyl pyridine, cyclic ethers such as tetrahydrofuran, tetrahydropyran or p-dioxane, aliphatic ethers such as diethyl ether and dibutyl ether, aldehydes, secondary alcohols, diols such as 1,4-butanediol,
Some of these reactions can be very vigorous to violent. TCCA reacts violently with pure secondary alcohols and alkenes.
Methyl t-butyl ether has been used as an inert solvent at low temperature (-20°C).
Referenceopen allclose all
TCCA reacts exothermically at room temperature with aliphatic cyclic ethers to give chlorinated products. For example, dry tetrahydrofuran and tetrahydropyran give 2,3-dichloro-tetrahydrofuran or 2,3-dichloro- tetrahydropyran, respectively. The reaction can be violent or even explosive if not controlled.
TCCA in the presence of water readily oxidizes tetrahydrofuran or tetrahydropyran at room temperature in a exothermic reaction to give γ-butyrolactone or δ-valerolactone, respectively.
Carbon tetrachloride, chloroform, methylene chloride, dimethylformamide, ethyl acetate, acetonitrile, acetone, toluene and acetic acid are typical solvents which do not interfere with the desired reactions, and thus are inert to TCCA under reaction conditions.
As TCCA is a neutral molecule, it is quite soluble in polar solvents which do not react. The solubility of TCCA in three solvents was measured
ethyl acetate: 385 g/L
acetone: 350 g/L
toluene: 70 g/L
Analysis for chlorination of these three solvents did not observe reaction with these solvents. TCCA reacts with a number of organics, producing either chlorinated or oxidized products. Reactions with specific functional groups are described below.
TCCA readily chlorinates alkenes. For example, TCCA reacts with cyclohexene in carbon tetrachloride to give 3-chlorocyclohexene in 29% yield.
TCCA chlorinates alkyl N-heterocycles, such as alkyl pyridine, in a chlorinated solvent at the α-position of the alkyl group.
TCCA in³50% H2SO4will react with aromatic compounds to give ring chlorination.
TCCA reacts with cyclic ethers, including tetrahydrofuran, tetrahydropyran or p-dioxane, to give chlorinated products.
TCCA in the presence of water oxidizes aliphatic ethers to give the corresponding esters, for example: diethyl ether to ethyl acetate or dibutyl ether to butylvalerate. The actual oxidant is probably HOCl.
TCCA oxidizes aldehydes in the presence of alcohols to the corresponding alcohol esters. The reaction is done in acetonitrile solvent.
TCCA oxidizes secondary alcohols or diols in acetone solvent to the corresponding ketones or lactones at room temperature in good to high yields. For example, cyclohexanol to cyclohexanone or 1,4-butanediol to γ-butyrolactone. Secondary alcohols are oxidized considerably faster than primary alcohols. TCCA reacts violently with pure secondary alcohols.
TCCA oxidizes indolines to indoles in methyl t-butyl ether solvent at low temperature (-20°C).
Description of key information
TCCA is stable in a variety of organic solvents such as carbon tetrachloride, chloroform, methylene chloride, dimethylformamide, ethyl acetate, acetonitrile, acetone, toluene and acetic acid.
Additional information
Several patents and journal articles are available which provide information on the stability of trichloroisocyanuric acid.
Information on Registered Substances comes from registration dossiers which have been assigned a registration number. The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). This information has not been reviewed or verified by the Agency or any other authority. The content is subject to change without prior notice.
Reproduction or further distribution of this information may be subject to copyright protection. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner.

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