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EC number: 203-618-0 | CAS number: 108-80-5
- 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 and scientifically acceptable patent demonstrating the stability of cyanuric acid in an variety of organic solvents
- Principles of method if other than guideline:
- This patent provides data on the pyrolysis of urea to CYA in diphenyl and diphenyl oxide solvents at 220-258ºC for 2-3 hours. The isolated yield of CYA was 90% or higher.
- GLP compliance:
- not specified
- Test substance stable:
- yes
- Conclusions:
- Cyanuric acid is stable in diphenyl and diphenyl oxide at temperatures up to 260ºC.
- 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 and scientifically acceptable patent demonstrating the stability of cyanuric acid in a variety of organic solvents
- Principles of method if other than guideline:
- An alternate method of manufacturing CYA is to conduct the urea pyrolysis reaction in an inert solvent. The reaction solvent must be inert to urea and the CYA product. This patent provides data on the pyrolysis of urea to CYA in adiponitrile solvent at 230ºC for 1.5 hours.
- GLP compliance:
- not specified
- Test substance stable:
- yes
- Conclusions:
- The patent provides information of the preparation of cyanuric acid from urea pyrolysis and determines that cyanuric acid is stable in aliphatic dinitriles such as malononitrile, succinonitrile, glutaronitrile, adiponitrile, pimelonitrile at temperatures up to 250ºC.
- 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 and scientifically acceptable patent demonstrating the stability of cyanuric acid in an organic solvent
- Principles of method if other than guideline:
- This patent provides data on the pyrolysis of urea to CYA in sulfolane or 3-methylsulfolane solvent at 205-210ºC for 2.5 hours. The isolated yield of CYA was 93-97%.
- Test substance stable:
- yes
- Conclusions:
- Cyanuric acid is stable in alkyl sulfones such as tetramethylene sulfone (sulfolane) or 3-methylsulfolane at temperatures up to 210ºC
- 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 and scientifically acceptable patent demonstrating the stability of cyanuric acid in an variety of organic solvents
- Principles of method if other than guideline:
- The patent provides data on the preparation of acyl derivatives of cyanuric acid and the base catalyzed reaction of CYA with ketene at 10-100°C to produce alkylated cyanurates.
- GLP compliance:
- not specified
- Test substance stable:
- yes
- Conclusions:
- Cyanuric acid is stable in acetone, tetrahydrofuran, dioxane, methyl ethyl ketone, ethylene glycol ethers, ethyl acetate, isopropyl acetate, butyl acetate, alkyl ethers, ethylene glycol dimethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol diethyl ether, ethylene glycol monoethyl ether acetate.
- 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 and scientifically acceptable patent demonstrating the stability of cyanuric acid in an variety of organic solvents
- Principles of method if other than guideline:
- This patent provides data on the pyrolysis of urea to CYA in N-cyclohexylpyrrolidone solvent at 225-240ºC for 0.5-4 hours.
- Test substance stable:
- yes
- Conclusions:
- Cyanuric acid is stable in 2-pyrrolidones, 2-oxazolidones, and tetrahydro-1,3-oxazine-2-ones at temperatures up to 240ºC
- 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 and scientifically acceptable patent demonstrating the stability of cyanuric acid in an variety of organic solvents
- Principles of method if other than guideline:
- This patent provides data on the pyrolysis of urea to CYA in various solvents at 170-245ºC for 1-6 hours.
- Test substance stable:
- yes
- Conclusions:
- Cyanuric acid is stable in tetralkylurea, cresol, xylenol, cresylic acid, dialkylformamide, dimethylacetamide, diethylene glycol monomethyl ether, dipropylene glycol monomethyl ether
- 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 and scientifically acceptable patent demonstrating the stability of cyanuric acid in an variety of organic solvents
- Principles of method if other than guideline:
- The patent describes a catalyzed base reaction of CYA with alkylating agents (R-X) at 150-200°C for several hours to produce alkylated cyanurates
- Test substance stable:
- yes
- Conclusions:
- Cyanuric acid is stable in halogenated aromatics such as o-dichlorobenzene, bromobenzene, trichlorobenzenes, chlorinated naphthalenes, chlorinated biphenyls; other aromatics such as toluene, xylenes, anisole and nitrobenzene; high boiling esters such as amyl acetate or dibutyl phthalate; ethers such as dioxane and diphenyl ether; and dimethylformamide
- 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 and scientifically acceptable patent demonstrating the stability of cyanuric acid in a variety of organic solvents
- Principles of method if other than guideline:
- This patent provides data on the pyrolysis of urea to CYA in N-methylpyrrolidone solvent at 200-210ºC for 3.5 hours.
- Test substance stable:
- yes
- Conclusions:
- The patent demsontrates that cyanuric acid is stable in 2-pyrrolidones, 2-oxazolidones, and tetrahydro-1,3-oxazine-2-ones at temperatures up to 240ºC.
Referenceopen allclose all
This patent provides data on the pyrolysis of urea to CYA in diphenyl and diphenyl oxide solvents at 220-258ºC for 2-3 hours. The isolated yield of CYA was 90% or higher.
Cyanuric acid was produced by the pyrolysis of urea to using sulfolane or 3 -methylsulfolane solvent at 205-210ºC for 2.5 hours. The isolated yield of CYA was 93-97%.
Cyanuric acid is stable in acetone, tetrahydrofuran, dioxane, methyl ethyl ketone, ethylene glycol ethers, ethyl acetate, isopropyl acetate, butyl acetate, alkyl ethers, ethylene glycol dimethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol diethyl ether, ethylene glycol monoethyl ether acetate. These are suitable solvents which are used as reaction medium for the acylation of cyanuric acid.
.
This patent provides data on the pyrolysis of urea to CYA in N-cyclohexylpyrrolidone solvent at 225-240ºC for 0.5-4 hours. The isolated yield of CYA was 95-99%.
Table 1:
Example |
Ratio ml solvent/g urea |
Time hrs |
Product assay |
|
Cyanuric acid % |
Ammelide % |
|||
Cresol (USP) as solvent |
||||
1 |
1 |
1 |
87.1 |
11.1 |
2 |
2 |
1 |
95.3 |
4.5 |
3 |
2 |
1 |
96.2 |
4.2 |
4 |
6 |
1 |
99.8 |
<0.2 |
5 |
6 |
1 |
99.3 |
<0.2 |
Tetramethylurea as solvent |
||||
6 |
1 |
1 |
68.2 |
12.3 |
7 |
1 |
1.5 |
83.3 |
8.0 |
8 |
1.6 |
1.5 |
95.5 |
1.9 |
9 |
1.6 |
1.5 |
94.4 |
1.5 |
10 |
4 |
1.5 |
99.6 |
0.2 |
11 |
6 |
1.5 |
99.7 |
<0.02 |
12 |
6 |
1.5 |
99.7 |
<0.02 |
Diethylene glycol monomethyl ether solvent |
||||
13 |
1 |
1 |
85.7 |
12.7 |
14 |
1 |
1 |
82.6 |
15.6 |
15 |
2 |
1 |
93.6 |
3.8 |
16 |
2 |
1 |
92.9 |
6.3 |
17 |
6 |
1 |
98.2 |
<0.1 |
Dipropylene glycol monomethyl ether solvent |
||||
18 |
1 |
1 |
79.0 |
15.7 |
19 |
2 |
1 |
91.2 |
7.4 |
20 |
10 |
1 |
98.7 |
0.04 |
Table 2:
Example |
Ratio ml solvent/g urea |
Time hrs |
Product assay |
|
Cyanuric acid % |
Ammelide % |
|||
Dimethylformamide as solvent |
||||
22 |
6 |
4 |
99.1 |
0 |
23 |
6 |
4 |
99.6 |
0 |
Diethylacetamide as solvent |
||||
24 |
2 |
3 |
89.8 |
0.02 |
25 |
2 |
3 |
96.5 |
0.16 |
26 |
2 |
3 |
96.9 |
0.43 |
27 |
2 |
1.5 |
98.2 |
0.55 |
28 |
6 |
1.5 |
100.0 |
0 |
29 |
6 |
1.5 |
100.0 |
0 |
30 |
6 |
1.5 |
99.9 |
0 |
The quantities of materials and rates of urea addition along with the results obtained are shown in table 1.
Cyanuric acid purity as a function of urea addition time |
|||||
Example |
Urea addition time (hrs) |
Urea (gms) |
Solvent (gms) |
G of urea per hour per grams of solvent |
Total ammelide and ammeline % |
1 |
0.55 |
169.8 |
266.4 |
1.15 |
2.34 |
2 |
0.90 |
270 |
360 |
0.83 |
2.22 |
3 |
1.02 |
270 |
360 |
0.73 |
1.92 |
4 |
3.5 |
335 |
375 |
0.26 |
0.46 |
Description of key information
A number of United States patents have been cited which demonstrate that cyanuric acid can be prepared by the pyrolysis of urea. The production of cyanuric acid involves dissolving the urea in a suitable organic solvent and heating to a high temperature. The patents demonstrate that often high yields of cyanuric acid are obtained by this method and therefore provide a reasoned weight of evidence that cyanuric acid is stable in a variety of organic solvents.
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