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Stability in organic solvents and identity of relevant degradation products

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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

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.

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

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%.

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

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.

.

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

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%.

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

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

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

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

 

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.

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.

Additional information