Symclosene

Stability in organic solvents and identity of relevant degradation products

Link to relevant study record(s)

Reference

Reference 1

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.

Reference 2

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.

Reference 3

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

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.

Conclusions:

TCCA reacts exothermically at room temperature with aliphatic cyclic ethers such as tetrahydrofuran and tetrahydropyran.

Reference 4

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.

Reference 5

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).

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).

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).

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.