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EC number: 246-438-8 | CAS number: 24731-73-5
Hydrolysis
Administrative data
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- key study
- Study period:
- 2006-04-13 to 2007-11-12
- Reliability:
- 1 (reliable without restriction)
- Rationale for reliability incl. deficiencies:
- other: Recent, well documented GLP and guideline study.
Data source
Reference
- Reference Type:
- study report
- Title:
- Unnamed
- Year:
- 2 007
- Report date:
- 2007
Materials and methods
Test guideline
- Qualifier:
- according to guideline
- Guideline:
- EU Method C.7 (Degradation: Abiotic Degradation: Hydrolysis as a Function of pH)
- Deviations:
- no
- GLP compliance:
- yes (incl. QA statement)
Test material
- Reference substance name:
- N,N'-1,4-phenylenebis[3-oxobutyramide]
- EC Number:
- 246-438-8
- EC Name:
- N,N'-1,4-phenylenebis[3-oxobutyramide]
- Cas Number:
- 24731-73-5
- Molecular formula:
- C14H16N2O4
- IUPAC Name:
- 3-oxo-N-[4-(3-oxobutanamido)phenyl]butanamide
- Details on test material:
- -
- Date of expiry: 22.07.2007
- Reference to Certificate of analysis: AZ-215, 23.06-2005 (DI S. Bär, Clariant GmbH, Production Services, CLAS Rhein-Main, Site Höchst)
Constituent 1
Study design
- Analytical monitoring:
- yes
- Details on sampling:
- The samples (filled in vials) were taken out of the water bath, cooled down to room temperature to slow down the hydrolysis progress and then placed into the auto sampler for analysis. The pH of each sample was measured in an aliquot of the solution.
- Buffers:
- • Standard-buffer solution pH4.00, Bernd Kraft GmbH, Art.-No.: 03083.3000
• Standard-buffer solution pH7.00, Bernd Kraft GmbH, Art.-No.: 03086.3000
• Standard-buffer solution pH9.00, Bernd Kraft GmbH, Art.-No.: 03088.3000
Duration of testopen allclose all
- Duration:
- 504 h
- pH:
- 4
- Temp.:
- 50 °C
- Initial conc. measured:
- 79.68 mg/L
- Duration:
- 52 h
- pH:
- 4
- Temp.:
- 65 °C
- Initial conc. measured:
- 81.06 mg/L
- Duration:
- 24 h
- pH:
- 4
- Temp.:
- 75 °C
- Initial conc. measured:
- 75.34 mg/L
- Duration:
- 503 h
- pH:
- 7
- Temp.:
- 50 °C
- Initial conc. measured:
- 78.46 mg/L
- Duration:
- 51 h
- pH:
- 7
- Temp.:
- 65 °C
- Initial conc. measured:
- 78.68 mg/L
- Duration:
- 23.5 h
- pH:
- 7
- Temp.:
- 75 °C
- Initial conc. measured:
- 80.41 mg/L
- Duration:
- 427 h
- pH:
- 9
- Temp.:
- 50 °C
- Initial conc. measured:
- 78.51 mg/L
- Duration:
- 65.3 h
- pH:
- 9
- Temp.:
- 65 °C
- Initial conc. measured:
- 73.48 mg/L
- Duration:
- 24 h
- pH:
- 9
- Temp.:
- 75 °C
- Initial conc. measured:
- 80.09 mg/L
Results and discussion
- Transformation products:
- not specified
Total recovery of test substance (in %)open allclose all
- % Recovery:
- 41.7
- pH:
- 4
- Temp.:
- 50 °C
- Duration:
- 504 h
- % Recovery:
- 51
- pH:
- 4
- Temp.:
- 65 °C
- Duration:
- 52 h
- % Recovery:
- 34.1
- pH:
- 4
- Temp.:
- 75 °C
- Duration:
- 24
- % Recovery:
- 35.6
- pH:
- 7
- Temp.:
- 50 °C
- Duration:
- 503 h
- % Recovery:
- 47.4
- pH:
- 7
- Temp.:
- 65 °C
- Duration:
- 51 h
- % Recovery:
- 29.8
- pH:
- 7
- Temp.:
- 75 °C
- Duration:
- 23.5 h
- % Recovery:
- 38.9
- pH:
- 9
- Temp.:
- 50 °C
- Duration:
- 427 h
- % Recovery:
- 38.1
- pH:
- 9
- Temp.:
- 65 °C
- Duration:
- 65.3
- % Recovery:
- 31.1
- pH:
- 9
- Temp.:
- 75 °C
- Duration:
- 24 h
Dissipation DT50 of parent compoundopen allclose all
- pH:
- 4
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.002 h-1
- DT50:
- 396.85 h
- Type:
- (pseudo-)first order (= half-life)
- Remarks on result:
- other: r=0.9998
- pH:
- 4
- Temp.:
- 65 °C
- Hydrolysis rate constant:
- 0.013 h-1
- DT50:
- 53.17 h
- Type:
- (pseudo-)first order (= half-life)
- Remarks on result:
- other: r=0.99989
- pH:
- 4
- Temp.:
- 75 °C
- Hydrolysis rate constant:
- 0.045 h-1
- DT50:
- 15.45 h
- Type:
- (pseudo-)first order (= half-life)
- Remarks on result:
- other: r=0.99998
- pH:
- 7
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.002 h-1
- DT50:
- 333.78 h
- Type:
- (pseudo-)first order (= half-life)
- Remarks on result:
- other: r=0.99939
- pH:
- 7
- Temp.:
- 65 °C
- Hydrolysis rate constant:
- 0.015 h-1
- DT50:
- 47.21 h
- Type:
- (pseudo-)first order (= half-life)
- Remarks on result:
- other: r=0.99969
- pH:
- 7
- Temp.:
- 75 °C
- Hydrolysis rate constant:
- 0.051 h-1
- DT50:
- 13.54 h
- Type:
- (pseudo-)first order (= half-life)
- Remarks on result:
- other: r=0.99948
- pH:
- 9
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.002 h-1
- DT50:
- 315.45 h
- Type:
- (pseudo-)first order (= half-life)
- Remarks on result:
- other: r=0.99846
- pH:
- 9
- Temp.:
- 65 °C
- Hydrolysis rate constant:
- 0.015 h-1
- DT50:
- 47.13 h
- Type:
- (pseudo-)first order (= half-life)
- Remarks on result:
- other: r=0.99944
- pH:
- 9
- Temp.:
- 75 °C
- Hydrolysis rate constant:
- 0.048 h-1
- DT50:
- 14.39 h
- Type:
- (pseudo-)first order (= half-life)
- Remarks on result:
- other: r=0.9994
Any other information on results incl. tables
RESULTS OF THE PRELIMINARY TEST
The measured values and calculated results of the preliminary test are summarized in thefollowing table.
Test conditions: Temperature = 50.0°C
test |
sample |
duration of |
concentration |
hydrolysed [%] |
pH-value |
results |
|
VT pH 4 Start |
0.0 |
74.04 |
0.0 |
4.0 |
|
4.0 |
VT pH 4 El |
2.4 |
73.79 |
0.3 |
4.0 |
further testing necessary |
|
VT pH 4 E2 |
120 |
60.40 |
18.4 |
4.0 |
50% (2.4 h) > deg. > 10% (5 d) |
|
VT pH 7 Start |
0.0 |
72.85 |
0.0 |
7.0 |
|
7.0 |
VT pH 7 El |
2.4 |
72.61 |
0.3 |
7.0 |
further testing necessary |
|
VT pH 7 E2 |
120 |
58.49 |
19.7 |
7.0 |
50% (2.4 h) > deg. > 10% (5 d) |
|
VT pH 9 Start |
0.0 |
73.10 |
0.0 |
9.0 |
|
9.0 |
VT pH 9 El |
2.4 |
71.35 |
2.4 |
9.0 |
further testing necessary |
|
VT pH 9 E2 |
120 |
43.16 |
41.0 |
9.0 |
50% (2.4 h) > deg. > 10% (5 d) |
At all tested pH-values more than 10% of hydrolysis after five days but less than 50% after 2.4hours was observed. To determine the reaction order and the rate constants of the hydrolysisreaction at these pH-values the main test had to be performed.
Extrapolation
| pH | Temperature | Hydrolysis rate constant | Half life | Type |
| 4 | 25 °C | 0.000039452 h^(-1) | 732 days | extrapolated |
| 7 | 25 °C | 0.000049092 h^(-1) | 588 days | extrapolated |
| 9 | 25 °C | 0.000059712 h^(-1) | 484 days | extrapolated |
Applicant's summary and conclusion
- Validity criteria fulfilled:
- yes
- Conclusions:
- The half-life times and the rate constants of the test item at the tested pH-values and at 25°C, were extrapolated using the corresponding regressed data from the testing at 50°C, 65°C and75°C. The half-life times at 25°C were:
pH4: 2.0 years,
pH7: 1.6 years and
pH9: 1.3 years - Executive summary:
The abiotic degradation of the test item Bis-acetoacetic-p-phenylenediamine was determined according to EC-guideline 92/69/EC, C.7.
The rate of degradation was estimated in preliminary tests at three different pH-values (pH4, pH7,and pH9).
At all three tested pH-values further tests according to the corresponding guideline had to be performed, because the test item had hydrolyzed less than 50% after 2.4 hours but more than 10% after five days at 50°C.
The main test for for all pH-values was performed at three temperatures (50°C, 65°C and 75°C). In each case a linear dependence of the time of degradation on the natural logarithm of the test item concentration was obtained, which means, that the hydrolysis reaction was pseudo-firstorder.
The relevant results are summarized in the following table.
pH4
pH7
pH9
Test type Temp.
Time
Hydrolysis
Time
Hydrolysis
Time
Hydrolysis
Preliminary test 50°C
2.4 h
5d
0.3 %
18.4%
2.4 h
5d
0.3 %
19.7%
2.4 5d
2.4 %
41.0%
Further testing (yes/no)
yes
yes
yes
Test type
EC-Test
Temp.
t(1/2) [h]
kobs [h-1]
t(1/2) [h]
kobs [h-1]
t(1/2) [h]
kobs[h-1]
Main test
1
50°C
396.9
1.7462 * 10-3
333.8
2.0762 * 10-3
315.5
2.1969 *10-3
3
65°C
53.2
1.3034 *10-2
47.2
1.4679 *10-2
47.1
1.4705 * 10.2
75°C
15.5
4.4857* 10-2
13.5
5.1191 * 10-2
14.4
4.8142 *10-2
Extrapolation
25°C
2.0a
3.9454 * 10-5
1.6a
4.9092 * 10-5
1.3a
5.9712 *10-5
Summing up it can be said, that the hydrolysis of Bis-acetoacetic-p-phenylenediamine was basecatalyzed but the effect of pH on the rate constant was not very strong.
The half-life times and the rate constants of the test item at the tested pH-values and at 25°C, were extrapolated using the corresponding regressed data from the testing at 50°C, 65°C and75°C. The half-life times at 25°C were:
pH4: 2.0 years,
pH7: 1.6 years and
pH9: 1.3 years
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