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EC number: 203-514-5 | CAS number: 107-71-1
Hydrolysis
Administrative data
Link to relevant study record(s)
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- key study
- Study period:
- 01.06.2017 - 31.07.2017
- 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)
- Radiolabelling:
- no
- Analytical monitoring:
- yes
- Details on sampling:
- Three samples were analysed at the start of the experiments. Two separate tubes were analysed at each analytical occasion of hydrolysis test. One sample was taken from the control vessels.
The whole amount of the vials was transferred to the SPE cartridges. The eluate was analysed by GC. - Buffers:
- pH 4.0: 1 mL 0.2 M Sodium hydroxide and 125 mL 0.2 M Potassium hydrogen phthalate were diluted to 500 mL with ultra-pure water.
pH 7.0: 74 mL 0.2 M Sodium hydroxide and 125 mL 0.2 M Potassium dihydrogen phosphate were diluted to 500 mL with ultra-pure water.
pH 9.0: 54 mL 0.2 M Sodium hydroxide and 125 mL 0.2 M Boric acid and Potassium chloride were diluted to 500 mL with ultra-pure water.
The pH of each buffer solution was checked with a calibrated pH meter. The required amount of the buffer solutions was prepared according to the above ratios. - Details on test conditions:
- TEST SYSTEM
- Equipment used: screw cap headspace vials
Balances: PG 203 S, Mettler Toledo, No.: 1122082152 BP210D, Sartorius, No.: 60602907
SPE cartridges: Discovery DSC-18, 3mL/500mg, No.: SP8914B
pH meter: InoLab pH Level 2, No.: 03260014
Ultrasonic bath: Branson 3210-E-MT, No.: A700343D
Water purification system: MILLIPORE, DIRECT Q5, No.: F0DA13956K
Thermostat: OMH 400, Heratherm, No.: 41865966
Hot air steriliser: M-53, Binder, No.: 910243
- Temperature: pH 4: 40, 50 and 60 ± 0.5 °C; pH 7: 30, 40 and 50 ± 0.5 °C; pH 9: 10, 20 and 30 ± 0.5 °C
- Lighting: no
- Measures taken to avoid photolytic effects: The hydrolysis reaction was carried out using a dark thermostat to avoid photolytic effects
- Measures to exclude oxygen: Nitrogen was bubbled into the water for five minutes before the preparation of the solutions in order to exclude oxygen.
TEST MEDIUM
- Volume used/treatment: 20 mL
- Kind and purity of water: ultra-pure water from water purification system
- Preparation of test medium: 201.65 mg of test item was dissolved in 10 mL of acetonitrile.
- Renewal of test solution: no
OTHER TEST CONDITIONS
- Adjustment of pH: yes, with Sodium hydroxide - Duration:
- 646 h
- pH:
- 4
- Temp.:
- 40 °C
- Initial conc. measured:
- 187 mg/L
- Duration:
- 525 h
- pH:
- 4
- Temp.:
- 50 °C
- Initial conc. measured:
- 187 mg/L
- Duration:
- 164 h
- pH:
- 4
- Temp.:
- 60 °C
- Initial conc. measured:
- 186 mg/L
- Duration:
- 495.5 h
- pH:
- 7
- Temp.:
- 30 °C
- Initial conc. measured:
- 206 mg/L
- Duration:
- 495.5 h
- pH:
- 7
- Temp.:
- 40 °C
- Initial conc. measured:
- 206 mg/L
- Duration:
- 164 h
- pH:
- 7
- Temp.:
- 50 °C
- Initial conc. measured:
- 187 mg/L
- Duration:
- 215 h
- pH:
- 9
- Temp.:
- 10 °C
- Initial conc. measured:
- 189 mg/L
- Duration:
- 72 h
- pH:
- 9
- Temp.:
- 20 °C
- Initial conc. measured:
- 214 mg/L
- Duration:
- 27 h
- pH:
- 9
- Temp.:
- 30 °C
- Initial conc. measured:
- 233 mg/L
- Number of replicates:
- 3
- Positive controls:
- no
- Negative controls:
- no
- Statistical methods:
- The pseudo-first order rate constant (kobs) for each test temperature was determined from the plots of the natural logarithm of the concentration versus time. Applying the Arrhenius equation the rate constant k and half-life were calculated at 20 °C from the plot of ln k versus 1/T.
- Preliminary study:
- Based on the results of the preliminary test (please refer to IUCLID section 5.1.2) the hydrolysis rate of the test substance was found to be 32 % at pH 4, 89 % at pH 7 and >99 % at pH 9 after 5 days at 50 °C. Based on the results obtained, the test substance was considered as hydrolytically unstable at pH 4, pH 7 and pH 9 under the conditions investigated and the subsequent full test was initiated.
- Test performance:
- Test solutions were prepared by adding 200 µL of Stock Solution II to 20 mL of the buffer solutions (pH = 4, pH = 7, pH = 9) in screw cap headspace vials. Before vials were closed oxygen was removed by blowing nitrogen into the tubes. Acetonitrile content of the test solutions was 1 % (v/v). Nominal starting concentration test item in the buffer solutions was 0.2 mg/mL around 1.5 mM.
SPE tubes were conditioned with 3 mL of tetrahydrofuran, then 3 mL methanol and 3 mL ultrapure water. Then 20 mL of the test solution (the whole amount of the vial) was loaded to the packing together with 0.5 mL Internal Standard Stock Solution. Then it was dried. The cartridges were washed with 1 mL ultrapure water. The test item was eluted with 5 mL of acetonitrile. The eluate was analysed by GC. - Transformation products:
- not measured
- % Recovery:
- 51
- pH:
- 4
- Temp.:
- 40 °C
- Duration:
- 646 h
- % Recovery:
- 27
- pH:
- 4
- Temp.:
- 50 °C
- Duration:
- 525 h
- % Recovery:
- 21
- pH:
- 4
- Temp.:
- 60 °C
- Duration:
- 164 h
- % Recovery:
- 27
- pH:
- 7
- Temp.:
- 30 °C
- Duration:
- 495.5 h
- % Recovery:
- 3
- pH:
- 7
- Temp.:
- 40 °C
- Duration:
- 495.5 h
- % Recovery:
- 6
- pH:
- 7
- Temp.:
- 50 °C
- Duration:
- 164 h
- % Recovery:
- 15
- pH:
- 9
- Temp.:
- 10 °C
- Duration:
- 215 h
- % Recovery:
- 21
- pH:
- 9
- Temp.:
- 20 °C
- Duration:
- 44.1 h
- % Recovery:
- 15
- pH:
- 9
- Temp.:
- 30 °C
- Duration:
- 27 h
- Key result
- pH:
- 4
- Temp.:
- 20 °C
- Hydrolysis rate constant:
- 0 h-1
- DT50:
- 8 122 h
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 7
- Temp.:
- 20 °C
- Hydrolysis rate constant:
- 0.001 h-1
- DT50:
- 784 h
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 9
- Temp.:
- 20 °C
- Hydrolysis rate constant:
- 0.022 h-1
- DT50:
- 32 h
- Type:
- (pseudo-)first order (= half-life)
- Details on results:
- TEST CONDITIONS
- pH, sterility, temperature, and other experimental conditions maintained throughout the study: Yes
MAJOR TRANSFORMATION PRODUCTS
- Transformation products were not investigated - Validity criteria fulfilled:
- yes
- Conclusions:
- The calculated half lives of the hydrolysis reactions at pH 4, pH 7 and pH 9 are as follows:
t 1/2 at pH 4 and 20 °C: 8122 h
t 1/2 at ph 7 and 20 °C: 784 h
t 1/2 at pH 9 and 20 °C: 32 h - Executive summary:
A study was conducted according to Regulation (EC) No 440/2008 Part C.7 and OECD test guideline 111 to determine the hydrolysis of the test substance as a function of pH. The tier 1 test according to guideline was conducted and revealed that the test item is hydrolytically not stable at pH 4, 7 and 9. Thus, the subsequent Tier 2 test for the determination of the hydrolysis half-life was conducted. Hydrolysis was examined at three different pH values 4, 7 and 9 at three different temperatures: pH 4: 40, 50 and 60 ± 0.5 °C; pH 7: 30, 40 and 50 ± 0.5 °C; pH 9: 10, 20 and 30 ± 0.5 °C . The hydrolysis reaction was carried out using a dark thermostat to avoid photolytic effects. Three samples were analysed at the start of the experiments. Two separate tubes were analysed at each analytical occasion of hydrolysis test. One sample was taken from the control vessels. Samples are diluted or concentrated on SPE cartridges and then analysed by a GC – FID method in the presence of benzonitrile internal standard. The pseudo-first order rate constant (kobs) for each test temperature was determined from the plots of the natural logarithm of the concentration versus time. Applying the Arrhenius equation the rate constant k and half-life were calculated at 20 °C for pH 4 = 8.5E-5 h-1 and 8122 h, respectively, for pH 7 = 8.8E-4 h-1 and 784 h, respectively and for pH 9 = 0.0217 h-1 and 32 h, respectively.
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- supporting study
- Study period:
- 2017-02 to 2017-4
- 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)
- Qualifier:
- according to guideline
- Guideline:
- EU Method C.7 (Degradation: Abiotic Degradation: Hydrolysis as a Function of pH)
- GLP compliance:
- yes (incl. QA statement)
- Specific details on test material used for the study:
- The test item was dissolved in acetonitrile.
- Radiolabelling:
- no
- Analytical monitoring:
- yes
- Details on sampling:
- - Sampling intervals: at start and at the end of test (5 days)
- Sampling method: grab samples
- Sampling times for pH measurements: at start and at the end of the test - Buffers:
- - pH: 4
- Composition of buffer: 1 mL 0.2 M Sodium hydroxide and 125 mL 0.2 M Potassium hydrogen phthalate were diluted to 500 mL with ultra-pure water.
- pH: 7
- Composition of buffer: 74 mL 0.2 M Sodium hydroxide and 125 mL 0.2 M Potassium dihydrogen phosphate were diluted to 500 mL with ultra-pure water.
- pH: 4
- Composition of buffer: 54 mL 0.2 M Sodium hydroxide and 125 mL 0.2 M Boric acid and Potassium chloride were diluted to 500 mL with ultra-pure water. - Details on test conditions:
- TEST SYSTEM
- Equipment used: screw cap headspace vials
Balances: PG 203 S, Mettler Toledo, No.: 1122082152 BP210D, Sartorius, No.: 60602907
SPE cartridges: Discovery DSC-18, 3mL/500mg, No.: SP8914B
pH meter: InoLab pH Level 2, No.: 03260014
Ultrasonic bath: Branson 3210-E-MT, No.: A700343D
Water purification system: MILLIPORE, DIRECT Q5, No.: F0DA13956K
Thermostat: OMH 400, Heratherm, No.: 41865966
Hot air steriliser: M-53, Binder, No.: 910243
- Temperature: 50 ° ± 0.5 °C
- Lighting: no
- Measures taken to avoid photolytic effects: The hydrolysis reaction was carried out using a dark thermostat to avoid photolytic effects
- Measures to exclude oxygen: Nitrogen was bubbled into the water for five minutes before the preparation of the solutions in order to exclude oxygen.
TEST MEDIUM
- Volume used/treatment: 20 mL
- Kind and purity of water: ultra-pure water from water purification system
- Preparation of test medium: 201.65 mg of test item was dissolved in 10 mL of acetonitrile.
- Renewal of test solution: no
OTHER TEST CONDITIONS
- Adjustment of pH: yes, with Sodium hydroxide - Duration:
- 5 d
- pH:
- 4
- Temp.:
- 50 °C
- Initial conc. measured:
- > 197 - < 212 mg/L
- Duration:
- 5 d
- pH:
- 7
- Temp.:
- 50 °C
- Initial conc. measured:
- > 213 - < 222 mg/L
- Duration:
- 5 d
- pH:
- 9
- Temp.:
- 50 °C
- Initial conc. measured:
- > 188 - < 219 mg/L
- Number of replicates:
- 6
- Positive controls:
- no
- Negative controls:
- no
- Statistical methods:
- The chromatograms were evaluated with the help of TotalChrom™ chromatography software. Ratio of the peak areas (the test item and the internal standard) was calculated and used for the computations. Calculations were carried out using “EXCEL for Windows".
- Preliminary study:
- pH 4: 32 % hydrolysis
pH 7: 89 % hydrolysis
pH 9: >99 % hydrolysis - Transformation products:
- no
- % Recovery:
- 68
- St. dev.:
- 2.9
- pH:
- 4
- Temp.:
- 50 °C
- Duration:
- 5 d
- % Recovery:
- 11
- St. dev.:
- 0.46
- pH:
- 7
- Temp.:
- 50 °C
- Duration:
- 5 d
- % Recovery:
- < 0.6
- pH:
- 9
- Temp.:
- 50 °C
- Duration:
- 5 d
- Remarks on result:
- other: below limit of quantification
- Details on results:
- TEST CONDITIONS
- pH and temperature maintained throughout the study: Yes
At pH 4:
- Range of maximum concentrations at end of study period:
At the end of the study period, the concentrations were 131 - 147 mg/L.
At pH 7:
- Range of maximum concentrations at end of study period:
At the end of the study period, the concentrations were 22 - 25 mg/L.
At pH 9:
- Range of maximum concentrations at end of study period:
At the end of the study period, the concentrations were below the LOQ of 1.3 mg/L. - Validity criteria fulfilled:
- yes
- Conclusions:
- Based on the results of the preliminary test the hydrolysis rate of test item was found to be 32 % at pH 4, 89 % at pH 7 and >99 % at pH 9 after 5 days at 50 °C. Based on the results obtained, test item can be considered as hydrolytically unstable at pH 4, pH 7 and pH 9 under the conditions investigated.
- Executive summary:
The hydrolysis of the test item was assessed in accordance with the OECD guideline 111 and the EU method C.7 in a preliminary test. The hydrolysis of the test item in different aqueous buffer solutions (pH = 4, 7 and 9) at 50 °C was investigated using GC. The content of test item in the different pH buffer samples was determined at the beginning and the end of the test periods. Six samples were analysed at the start of the study. Based on the measured concentration the hydrolysis of the test item was determined to be 32 % at pH = 4; 89 % at pH = 7 and >99 % at pH = 9. Based on the results obtained, test item can be considered as hydrolytically unstable at pH 4, pH 7 and pH 9 under the conditions investigated. No observations were made which case doubt on the validity of the study results.
Referenceopen allclose all
Measured data at pH 4
Temperature | Sampling time (hours) | Concentration | Hydrolysis | Measured pH |
40 °C | Control buffer | - | - | 4.00 |
Start | 187 (n = 3) | - | 4.01 | |
22 | 184 | 2 | 4.02 | |
120 | 158 | 16 | 4.00 | |
166 | 158 | 15 | 4.03 | |
222 | 140 | 26 | 4.02 | |
239 | 141 | 25 | 4.01 | |
311 | 134 | 28 | 4.04 | |
484 | 105 | 44 | 4.00 | |
646 | 95 | 49 | 4.01 | |
50 °C | Control buffer | - | - | 4.02 |
Start | 187 (n = 3) | - | 3.98 | |
22 | 181 | 4 | 4.01 | |
70 | 154 | 18 | 3.99 | |
120 | 131 | 30 | 4.00 | |
166 | 116 | 38 | 4.02 | |
239 | 93.5 | 50 | 4.01 | |
311 | 80.9 | 57 | 4.00 | |
381 | 70.4 | 62 | 3.98 | |
525 | 51.2 | 73 | 4.04 | |
60 °C | Control buffer | - | - | 4.03 |
Start | 186 (n = 3) | - | 4.02 | |
3 | 188 | 0 | 4.02 | |
20 | 166 | 11 | 4.02 | |
29 | 139 | 25 | 4.01 | |
52 | 121 | 35 | 4.02 | |
75 | 95.3 | 49 | 4.03 | |
92 | 83.2 | 55 | 4.02 | |
164 | 39.8 | 79 | 4.01 |
Measured data at pH 7
Temperature | Sampling time (days) | Concentration | Hydrolysis | Measured pH |
30 °C | Control buffer | - | - | 7.04 |
Start | 206 (n = 3) | - | 7.02 | |
15.5 | 190 | 8 | 7.04 | |
47.5 | 178 | 14 | 7.00 | |
88.5 | 163 | 21 | 6.97 | |
160.5 | 140 | 32 | 7.03 | |
230.5 | 104 | 49 | 7.04 | |
333.5 | 92.9 | 55 | 7.04 | |
423.5 | 71.2 | 65 | 7.03 | |
495.5 | 56.3 | 73 | 7.00 | |
40 °C | Control buffer | - | - | 7.02 |
Start | 206 (n = 3) | - | 7.02 | |
15.5 | 182 | 12 | 7.00 | |
47.5 | 148 | 28 | 7.02 | |
71.5 | 121 | 41 | 6.99 | |
88.5 | 112 | 46 | 7.02 | |
160.5 | 68.7 | 67 | 7.02 | |
230.5 | 45.4 | 78 | 7.01 | |
333.5 | 14.1 | 93 | 7.04 | |
423.5 | 9.65 | 95 | 7.03 | |
495.5 | 6.72 | 97 | 6.99 | |
50 °C | Control buffer | - | - | 7.04 |
Start | 187 | - | 7.00 | |
3 | 188 | 0 | 7.02 | |
20 | 137 | 27 | 7.00 | |
29 | 114 | 39 | 7.01 | |
51.5 | 84.1 | 55 | 7.02 | |
75 | 52.0 | 72 | 7.02 | |
92 | 38.6 | 79 | 7.02 | |
114 | 28.7 | 85 | 7.01 | |
164 | 11.1 | 94 | 7.02 |
Measured data at pH 9
Temperature | Sampling time (hours) | Concentration | Hydrolysis | Measured pH |
10 °C | Control buffer | - | - | 9.03 |
Start | 189 (n = 3) | - | 9.02 | |
46 | 135 | 29 | 8.99 | |
76 | 112 | 41 | 9.01 | |
94 | 101 | 47 | 9.01 | |
144 | 76.7 | 59 | 9.00 | |
175 | 63.3 | 66 | 9.01 | |
215 | 47.1 | 75 | 9.02 | |
20 °C | Control buffer | - | - | 9.00 |
Start | 214 | - | 9.03 | |
7 | 192 | 10 | 8.99 | |
21 | 128 | 40 | 9.03 | |
31 | 106 | 50 | 9.01 | |
48 | 73.0 | 66 | 8.99 | |
56 | 63.2 | 70 | 9.00 | |
72 | 44.1 | 79 | 9.01 | |
30 °C | Control buffer | - | - | 8.98 |
Start | 233 | - | 9.00 | |
1.5 | 202 | 14 | 9.01 | |
3 | 171 | 26 | 9.02 | |
4.5 | 160 | 31 | 8.98 | |
6 | 150 | 36 | 9.03 | |
7.5 | 130 | 44 | 9.01 | |
11.5 | 103 | 56 | 9.01 | |
22 | 50.6 | 78 | 9.02 | |
27 | 34.2 | 85 | 8.99 |
Rate constants and half-lives based on the measured data | |||||
pH | Temperature | Slope | kobs, 1/h | t1/2 | Regression Coefficient |
4 | 40 °C | -0.00109 | 0.00109 | 639 h | 0.984 |
50 °C | -0.00251 | 0.00251 | 276 h | 0.992 | |
60 °C | -0.00946 | 0.00946 | 73.3 h | 0.996 | |
7 | 30 °C | -0.00251 | 0.00251 | 276 h | 0.992 |
40 °C | -0.00718 | 0.00718 | 96.6 h | 0.991 | |
50 °C | -0.01723 | 0.01723 | 40.2 h | 0.999 | |
9 | 10 °C | -0.00624 | 0.00624 | 111 h | 0.997 |
20 °C | -0.02206 | 0.02206 | 31.4 h | 0.997 | |
30 °C | -0.06860 | 0.06860 | 10.1 h | 0.998 | |
Estimation of the half lives of the reaction at 20 °C | ||||||||||
Temperature | 1/T | pH 4 | pH 7 | pH 9 | ||||||
°C | (1/K) | kobs | ln k- | t1/2, h | kobs | ln k | t1/2, h | kobs | ln k | t1/2, h |
10 | 0.00353 | - | - | - | - | - | - | 0.0062 | -5.08 | 111 |
20 | 0.00341 | - | - | - | - | - | - | 0.0221 | -3.81 | 31.4 |
30 | 0.00330 | - | - | - | 0.0025 | -5.99 | 276 | 0.0686 | -2.68 | 10.1 |
40 | 0.00319 | 0.0011 | -6.83 | 639 | 0.0072 | -4.94 | 96.6 | - | - | - |
50 | 0.00309 | 0.0025 | -5.99 | 276 | 0.0172 | -4.06 | 40.2 | - | - | - |
60 | 0.00300 | 0.0095 | -4.66 | 73.3 | - | - | - | - | - | - |
20 (calculated) |
| 8.5E-5 | -9.37 | 8122 | 0.00088 | -7.03 | 784 | 0.0217 | -3.83 | 32 |
Constant | 29.1 | 25.2 | 31.3 | |||||||
X coefficient | -11263 | -9438 | -10294 | |||||||
R Squared | 0.979 | 0.999 | 1.000 | |||||||
Description of key information
The rate constant k and half-life were determined at 20 °C for pH 4 = 8.5E-5 h-1 and 8122 h respectively, for pH 7 = 8.8E-4 h-1 and 784 h, respectively and for pH 9 = 0.0217 h-1 and 32 h, respectively.
Key value for chemical safety assessment
- Half-life for hydrolysis:
- 784 h
- at the temperature of:
- 20 °C
Additional information
Key study
A study was conducted according to Regulation (EC) No 440/2008 Part C.7 and OECD test guideline 111 to determine the hydrolysis of the test substance as a function of pH. The tier 1 test according to guideline was conducted and revealed that the test item is hydrolytically not stable at pH 4, 7 and 9. Thus, the subsequent Tier 2 test for the determination of the hydrolysis half-life was conducted. Hydrolysis was examined at three different pH values 4, 7 and 9 at three different temperatures: pH 4: 40, 50 and 60 ± 0.5 °C; pH 7: 30, 40 and 50 ± 0.5 °C; pH 9: 10, 20 and 30 ± 0.5 °C . The hydrolysis reaction was carried out using a dark thermostat to avoid photolytic effects. Three samples were analysed at the start of the experiments. Two separate tubes were analysed at each analytical occasion of hydrolysis test. One sample was taken from the control vessels. Samples are diluted or concentrated on SPE cartridges and then analysed by a GC – FID method in the presence of benzonitrile internal standard. The pseudo-first order rate constant (kobs) for each test temperature was determined from the plots of the natural logarithm of the concentration versus time. Applying the Arrhenius equation the rate constant k and half-life were calculated at 20 °C for pH 4 = 8.5E-5 h-1 and 8122 h, respectively, for pH 7 = 8.8E-4 h-1 and 784 h, respectively and for pH 9 = 0.0217 h-1 and 32 h, respectively.
Supporting study
The hydrolysis of the test item was assessed in accordance with the OECD guideline 111 and the EU method C.7 in a preliminary test. The hydrolysis of the test item in different aqueous buffer solutions (pH = 4, 7 and 9) at 50 °C was investigated using GC. The content of test item in the different pH buffer samples was determined at the beginning and the end of the test periods. Six samples were analysed at the start of the study. Based on the measured concentration the hydrolysis of the test item was determined to be 32 % at pH = 4; 89 % at pH = 7 and >99 % at pH = 9. Based on the results obtained, test item can be considered as hydrolytically unstable at pH 4, pH 7 and pH 9 under the conditions investigated. No observations were made which case doubt on the validity of the study results.
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