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EC number: 931-203-0 | CAS number: 1335202-88-4
Hydrolysis
Administrative data
Link to relevant study record(s)
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- key study
- Study period:
- 13.01.2005-15.03.2005
- Reliability:
- 1 (reliable without restriction)
- Rationale for reliability incl. deficiencies:
- guideline study
- Qualifier:
- according to guideline
- Guideline:
- OECD Guideline 111 (Hydrolysis as a Function of pH)
- Deviations:
- no
- 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)
- Analytical monitoring:
- yes
- Details on sampling:
- - Sampling intervals for the parent/transformation products: samples were taken at the beginning of the test and after 24, 48, 72, 120, 144, and 168 h at pH 4, 7, and 9 at 50°
- Sampling method: sampling was performed by adding the same volume acetonitrile (5 mL) with 2% glacial acetic acid directly to the incubation vessels and direct injection of the sample
- Sampling intervals/times for pH measurements: pH of test solution was determined at the beginning of the test and after 24, 48, 72, 120, 144, and 168 h at pH 4, 7, and 9 at 50° - Buffers:
- - pH: 4, 7, and 9
- Type and final molarity of buffer: 0.05 M citrate buffer (pH 4), 0.05 M phosphate buffer (pH 7), and 0.05 M borate buffer (pH 9) according to EC method C.7 (92/69/EC), OECD guideline 111 and/or BBA Merkblatt Nr. 55, Teil I
- Composition of buffer: not reported, but buffer systems selected according to EC method C.7 (92/69/EC), OECD guideline 111 and/or BBA Merkblatt Nr. 55, Teil I - Details on test conditions:
- TEST SYSTEM
- Type, material and volume of test flasks, other equipment used: amber glass vials (volume: 20 mL) closed with PTFE sealed screw caps
- Sterilisation method: not reported
- Measures taken to avoid photolytic effects: photolytic interference was avoided (amber glass vials)
- Measures to exclude oxygen: all suitable precautions were taken to exclude dissolved oxygen: bubbling the solution with helium for five minutes before preparing the test solution
- Details of traps for volatile, if any: no traps used
- If no traps were used, is the test system closed/open: the system was closed with PTFE sealed screw caps
- Is there any indication of the test material adsorbing to the walls of the test apparatus? no
TEST MEDIUM
- Volume used/treatment: 5 mL
- Kind and purity of water: bi-distilled grade
- Preparation of test medium: The test item was dissolved in acetone (100 mg/L). 0.5 mL of this stock solution were transferred to a series of 20 mL glass vials. The solvent was evaporated under a fume hood at ambient temperature overnight. Afterwards, 5 mL of the selected buffer was added to each vial. The vials were closed with PTFE sealed screw caps. The concentration did not exceed 0.01 M at the test temperature. The nominal concentrations were 10 mg/L at pH 4, 7, and 9.
- Renewal of test solution: no
- Identity and concentration of co-solvent: acetone was used to prepare the stock solution (100 mg test item/L); after transferring 0.5 ml of this stock solution to the test vials the solvent was evaporated (no further solvents used in the test)
OTHER TEST CONDITIONS
- Adjustment of pH: no
- Dissolved oxygen: all suitable precautions were taken to exclude dissolved oxygen: bubbling the solution with helium for five minutes before preparing the test solution - Duration:
- 7 d
- pH:
- 4
- Temp.:
- 50 °C
- Initial conc. measured:
- 7.37 mg/L
- Duration:
- 7 d
- pH:
- 7
- Temp.:
- 50 °C
- Initial conc. measured:
- 7.45 mg/L
- Duration:
- 7 d
- pH:
- 9
- Temp.:
- 50 °C
- Initial conc. measured:
- 8.17 mg/L
- Number of replicates:
- All measurements were carried out in duplicate (no further informations)
- Preliminary study:
- Only the preliminary test was carried out.
- Test performance:
- In a preliminary test conducted according to OECD Guideline 111 and EU-Method C.7 the hydrolysis of the test item as a function of pH was investigated.
- Transformation products:
- yes
- No.:
- #1
- No.:
- #2
- Details on hydrolysis and appearance of transformation product(s):
- - Formation and decline of each transformation product during test: mono-, di-, and triester were detected; the tri-esters were rapidly degraded to di-esters, which sequentially degrade to the mono-esters
- Pathways for transformation: ester cleavage - pH:
- 4
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.01 h-1
- DT50:
- 27.3 d
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 7
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.01 h-1
- DT50:
- 72.3 h
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 9
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.01 h-1
- DT50:
- 47.8 h
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 4
- Temp.:
- 25 °C
- Hydrolysis rate constant:
- 0.69 a-1
- DT50:
- > 1 yr
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 7
- Temp.:
- 25 °C
- Hydrolysis rate constant:
- 0.01 h-1
- DT50:
- 17 d
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 9
- Temp.:
- 25 °C
- Hydrolysis rate constant:
- 0.01 h-1
- DT50:
- 11.3 d
- Type:
- (pseudo-)first order (= half-life)
- Validity criteria fulfilled:
- yes
- Conclusions:
- The hydrolysis of partially unsaturated TEA-EQ as a function of pH was investigated in a study conducted according to OECD Guideline 111 and EU-method C.7. (Preliminary test; main test not conducted due to the pronounced biodegradability of the test substance). At pH 4 and 50°C, the degradation of the main component of partially unsaturated TEA-EQ was less than 10% over a period of 120 h. The corresponding half-life at 25°C is therefore assumed to be above one year (default assumption acc. to guidelines). In contrast, at pH 7 and 9 and 50°C, more than 10% of the test item were hydrolysed within 120 h. Based on the results half-lives of 17 (pH 7) and 11.3 d (pH 9) were deduced from the reaction rate constants at 25°C. Di- and mono-ester were detected as degradation products.
- Executive summary:
The hydrolysis of partially unsaturated TEA-EQ as a function of pH was investigated in a study conducted according to OECD Guideline 111 and EU-method C.7. (Preliminary test; main test not conducted due to the pronounced biodegradability of the test substance).
The following results were obtained:
Hydrolysis of partially unsaturated TEA-EQ at 50°C
pH
Temperature (°C)
Rate constant
t1/2
4
50
0.00106 1/h
27.3 d
7
50
0.00958 1/h
72.3 h
9
50
0.01449 1/h
47.8 h
Hydrolysis of partially unsaturated TEA-EQ at 25°C
pH
Temperature (°C)
Rate constant
t1/2
4
25*
0.693 1/a
>1 a*
7
25
0.00169 1/h
17.0 d
9
25
0.00256 1/h
11.3 d
* default assumption acc. to guideline
At pH 4 and 50°C, the degradation of the main component of partially unsaturated TEA-EQ was less than 10% over a period of 120 h. The corresponding half-life at 25°C is therefore assumed to be above one year (default assumption acc. to guidelines). In contrast, at pH 7 and 9 and 50°C, more than 10% of the test item were hydrolysed within 120 h. Based on the results half-lives of 17 (pH 7) and 11.3 d (pH 9) were deduced from the reaction rate constants at 25°C. Di- and mono-ester were detected as degradation products.
Reference
1. Time course of partially unsaturated TEA-EQ at pH 4, 7, and 9 and 50°C
a. Time course of partially unsaturated TEA-EQ at pH 4 and 50°C
Time (h) |
pH |
Actual concentration (mg/L) |
Actual concentration in (%) of initial conc. |
0 24 48 72 120 144 168 |
4.02 4.00 4.02 4.00 4.00 4.00 4.00 |
7.37 7.24 6.85 7.09 3.58* 7.03 5.69 |
100 98.3 92.9 96.2 48.7* 95.5 77.2 |
Mean Std. Deviation RSD |
4.01 0.01 0.25 |
*discarded as an outliner
b. Time course of partially unsaturated TEA-EQ at pH 7 and 50°C
Time (h) |
pH |
Actual concentration (mg/L) |
Actual concentration in (%) of initial conc. |
0 24 48 72 120 144 168 |
7.06 7.03 7.00 7.00 6.99 6.99 6.98 |
7.45 4.37 3.12 3.38 0.887* 1.59 1.25 |
100 58.7 41.9 45.3 11.9* 21.3 16.7 |
Mean Std. Deviation RSD |
7.01 0.03 0.43 |
*discarded as an outliner
c. Time course of partially unsaturated TEA-EQ at pH 9 and 50°C
Time (h) |
pH |
Actual concentration (mg/L) |
Actual concentration in (%) of initial conc. |
0 24 48 72 120 144 168 |
9.03 9.01 9.04 9.04 9.03 9.01 9.03 |
8.17 3.54 2.89 1.84 0.486* 0.767 0.590 |
100 43.3 35.4 22.5 5.9* 9.4 7.2 |
Mean Std. Deviation RSD |
9.03 0.01 0.11 |
*discarded as an outliner
The temperature during the entire period of the test was measured to be 50.0 to 50.2°C
The results from the 120 h sampling were regarded as artefact, and therefore excluded from the analysis. As a consequence, the measurement was extended to 168 h test duration.
2. Rate constants and half-lives at 50 and 25°C
pH 4 |
pH 7 |
pH 9 |
|
50°C |
|||
Kobs (h) |
0.00106 |
0.00958 |
0.01449 |
t1/2 (h) |
654 |
72.3 |
47.8 |
t1/2 (d) |
27.3 |
3.01 |
1.99 |
25°C |
|||
Kobs (h) |
0.000187 |
0.00169 |
0.00256 |
t1/2 (h) |
3700 |
409 |
271 |
t1/2 (d) |
154.2 |
17.0 |
11.3 |
The degradation rate was calculated according to the assumption of Arrhenius.
At pH 4 and 50°C, the degradation of the main component of partially unsaturated TEA-EQ was less than 10% over a period of 120 h. The corresponding half-life at 25°C is therefore assumed to be above one year (default assumption acc. to guidelines). In contrast, at pH 7 and 9 and 50°C, more than 10% of the test item were hydrolysed within 120 h. Based on the results half-lives of 17 (pH 7) and 11.3 d (pH 9) were deduced from the reaction rate constants at 25°C.
Description of key information
Half-life:
> 1 year at a pH of 4 and 25 °C
17 days at a pH of 7 and 25 °C
11.3 days at a pH of 9 and 25 °C
(OECD TG 111 / EU-method C.7, preliminary test; RL1; GLP)
Key value for chemical safety assessment
Additional information
The hydrolysis of partially unsaturated TEA-EQ as a function of pH was investigated in a study conducted according to OECD Guideline 111 and EU-method C.7. (Preliminary test; main test not conducted due to the pronounced biodegradability of the test substance).
The following results were obtained:
Hydrolysis of partially unsaturated TEA-EQ at 50°C
pH
| Temperature (°C)
| Rate constant
| t1/2
|
4 | 50 | 0.00106 1/h | 27.3 d |
7 | 50 | 0.00958 1/h | 72.3 h |
9 | 50 | 0.01449 1/h | 47.8 h |
Hydrolysis of partially unsaturated TEA-EQ at 25°C
pH
| Temperature (°C)
| Rate constant
| t1/2
|
4 | 25* | 0.693 1/a | >1 a* |
7 | 25 | 0.00169 1/h | 17.0 d |
9 | 25 | 0.00256 1/h | 11.3 d |
* default assumption acc. to guideline
At pH 4 and 50°C, the degradation of the main component of partially unsaturated TEA-EQ was less than 10% over a period of 120 h. The corresponding half-life at 25°C is therefore assumed to be above one year (default assumption acc. to guidelines). In contrast, at pH 7 and 9 and 50°C, more than 10% of the test item were hydrolysed within 120 h. Based on the results half-lives of 17 (pH 7) and 11.3 d (pH 9) were deduced from the reaction rate constants at 25°C. Di- and mono-ester were detected as degradation products
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