Registration Dossier
Registration Dossier
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EC number: 219-143-7 | CAS number: 2372-21-6
Hydrolysis
Administrative data
Link to relevant study record(s)
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- key study
- Study period:
- Experimental starting date: 20 May 2014 Experimental completion date: 17 June 2015
- 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
- GLP compliance:
- yes (incl. QA statement)
- Specific details on test material used for the study:
- The test substance (project sample code T14012) was supplied by the sponsor in April 2014. Data on the characteristics, handling and purity of the test substance, supplied by the sponsor, are assumed to be correct and were used without further check.
EC name: O,O-tert-butyl isopropyl monoperoxycarbonate
Trade name: Trigonox BPIC-C75
Batch/Lot no.: 1203442069
Purity: 74.6% O,O-tert-butyl isopropyl monoperoxycarbonate 24.5% Isododecane: mixture of isomers <1% Others
Water solubility: 2.2 g/L (AkzoNobel, 2013)
Appearance: Clear liquid
Expiry date: April 1, 2022
Storage: Approx. 5°C - Radiolabelling:
- no
- Analytical monitoring:
- yes
- Remarks:
- HPLC
- Details on sampling:
- Sterile aqueous buffer solutions of different pH values (pH 4, 7 and 9) were spiked with the test substance and incubated at three different temperatures in the dark under controlled laboratory conditions.
Additionally, a sterile aqueous buffer solution pH 1.2 was spiked with the test substance and incubated (37°C) in the dark under controlled laboratory conditions. After appropriate time intervals, buffer solutions were analysed for the amount of test substance still available. - Buffers:
- Sterile test buffer solutions of pH 1.2, 4, 7 and 9 were prepared in glass bottles according to the description in Annex 3 of OECD 111 and purged with nitrogen for at least 5 minutes.
- Details on test conditions:
- Chemicals:
All chemicals used were of reagent grade, unless stated otherwise. Buffer solutions of different pH values were prepared according to the information as described in Annex 3 of OECD 111.
Materials:
All glassware and buffer solutions were sterilised. Test solutions were flushed with nitrogen to minimise oxidation. Test vessels were kept under dark conditions. A temperature-controlled water bath was used; temperature was measured using a calibrated thermometer, pH was measured using a pH meter.
Test procedure:
The hydrolysis study was carried out according to OECD guideline 111. Sterilization of the buffer solutions was performed by autoclaving at 121°C for 20 minutes. Sterilization of glassware was performed by heating at 180°C for at least 30 minutes. - Duration:
- 120 h
- pH:
- 4
- Temp.:
- 50 °C
- Initial conc. measured:
- 338.7 mg/L
- Duration:
- 120 h
- pH:
- 7
- Temp.:
- 50 °C
- Initial conc. measured:
- 336.3 mg/L
- Duration:
- 120 h
- pH:
- 9
- Temp.:
- 50 °C
- Initial conc. measured:
- 334.5 mg/L
- Positive controls:
- not specified
- Negative controls:
- not specified
- Preliminary study:
- The screening hydrolysis study was performed separately for each pH value tested. Results of the different pH values are displayed below.
pH 4
The pH value at the start of the test was measured to be 4.0. The temperature throughout the test was measured to be 50.0°C. It was observed that more than 90% of the test substance was hydrolysed after ±27 hours.
pH 7
The pH value at the start of the test was measured to be 7.1. The temperature throughout the test was measured to be 50.0°C. It was observed that more than 90% of the test substance was hydrolysed after ±27 hours.
pH 9
The pH value at the start of the test was measured to be 9.1. The temperature throughout the test was measured to be 50.0°C. It was observed that more than 90% of the test substance was hydrolysed after ±23 hours.
As more than 10% of hydrolysis was observed in Tier 1 for all pH values also Tier 2 had to be performed for the three tested pH values. - Transformation products:
- not measured
- Key result
- pH:
- 4
- Temp.:
- 10 °C
- Hydrolysis rate constant:
- 0.009 d-1
- DT50:
- 79 d
- Type:
- not specified
- Key result
- pH:
- 4
- Temp.:
- 30 °C
- Hydrolysis rate constant:
- ca. 0.148 d-1
- DT50:
- ca. 5 d
- Type:
- not specified
- Key result
- pH:
- 4
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- ca. 0.08 h-1
- DT50:
- ca. 0.4 d
- Type:
- not specified
- Key result
- pH:
- 7
- Temp.:
- 10 °C
- Hydrolysis rate constant:
- ca. 0.012 d-1
- DT50:
- ca. 63 d
- Type:
- not specified
- Key result
- pH:
- 7
- Temp.:
- 30 °C
- Hydrolysis rate constant:
- ca. 0.173 d-1
- DT50:
- ca. 4 d
- Type:
- not specified
- Key result
- pH:
- 7
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- ca. 0.083 d-1
- DT50:
- ca. 0.3 d
- Type:
- not specified
- Key result
- pH:
- 9
- Temp.:
- 10 °C
- Hydrolysis rate constant:
- ca. 0.058 d-1
- DT50:
- ca. 290 h
- Type:
- not specified
- Key result
- pH:
- 9
- Temp.:
- 30 °C
- Hydrolysis rate constant:
- ca. 0.034 h-1
- DT50:
- ca. 21 h
- Type:
- not specified
- Key result
- pH:
- 9
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- ca. 0.283 h-1
- DT50:
- ca. 2 h
- Type:
- not specified
- Validity criteria fulfilled:
- yes
- Conclusions:
- The purpose of this study was to determine if the test substance would hydrolyze at environmentally relevant pH values, complying with the OECD Guideline No. 111.
The substance is relatively stable at environmentally relevant pH levels and temperatures. - Executive summary:
The purpose of this study was to determine if the test substance would hydrolyze at environmentally relevant pH values, complying with the OECD Guideline No. 111.
An overview of the calculated half-lives for the test substance at the different pH values and tested temperatures are displayed in the table below. Also the interpolated half-lives for the temperature of 25°C are displayed.
pH value
Temperature °C
Replicate
t1/2
days
pH 4
10
I
*
II
79
Mean
79
30
I
5
II
5
Mean
5
50
I
0.4
II
0.3
Mean
0.4
25
interpolated
10
pH 7
10
I
59
II
67
Mean
63
30
I
4
II
4
Mean
4
50
I
0.3
II
0.3
Mean
0.3
25
interpolated
9
t1/2
hr
pH 9
10
I
284
II
295
Mean
290
30
I
20
II
22
Mean
21
50
I
2
II
2
Mean
2
25
interpolated
45
An additional hydrolysis experiment was carried out for pH value 1.2 at 37°C. Hydrolysis results are displayed in the table below.
Time
hours
Concentration (Ct)
mg/L
Hydrolysis
%
0
241.5
0.0
0.5
234.4
3.0
1
212.3
12.1
2
204.9
15.2
4
208.7
13.6
6
196.8
18.5
Reference
Hydrolysis of unstable substances (Tier 2)
Tier 2 of the hydrolysis study was carried out for pH values 4, 7 and 9 at three different temperatures, 10, 30 and 50°C. Results for the different pH values and test temperatures are described below.
pH 4
10 °C
The temperature throughout the test was measured to be 10.0°C. The pH of the buffer solution was checked at the start of the test and was measured to be 4.1. The results of replicate I showed very variable figures for hydrolysis. Measured concentrations at several time points were more than 20% higher than initial concentration. This cannot be caused by the uncertainty of the analytical method and therefore these results were considered to be outliers. Due to these unreliable results it was decided not to use the results of replicate I and to perform calculations with only one series of results. After 30 days about 18% of hydrolysis of the test substance was observed.
Time days |
Replicate I1) |
Replicate II |
||||
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
|
0 |
210.0 |
2.32 |
0.0 |
282.4 |
2.45 |
0.0 |
2 |
309.2 |
2.49 |
-47.3 |
312.5 |
2.49 |
-10.7 |
5 |
306.5 |
2.49 |
-46.0 |
285.7 |
2.46 |
-1.2 |
7 |
302.7 |
2.48 |
-44.2 |
314.0 |
2.50 |
-11.2 |
12 |
201.5 |
2.30 |
4.0 |
251.9 |
2.40 |
10.8 |
20 |
183.8 |
2.26 |
12.5 |
255.1 |
2.41 |
9.7 |
23.1 |
203.4 |
2.31 |
3.1 |
251.6 |
2.40 |
10.9 |
30 |
184.0 |
2.26 |
12.4 |
231.8 |
2.37 |
17.9 |
1)Due to unreliable results, figures of replicate I were not used for further calculations
The results were used to calculate the half-life (t0.5), applying the Arrhenius relationship. The half-life for the test substance was calculated to be 79 days.
30 °C
The temperature during the test varied between 29.9 and 30.0°C. The pH of the buffer solution was checked at the start of the test and was measured to be 4.0. After 11 days between 78 and 80% of hydrolysis of the test substance was observed.
Time days |
Replicate I |
Replicate II |
||||
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
|
0 |
230.4 |
2.36 |
0.0 |
271.9 |
2.43 |
0.0 |
2 |
174.5 |
2.24 |
24.3 |
202.5 |
2.31 |
25.5 |
2.75 |
143.3 |
2.16 |
37.8 |
173.6 |
2.24 |
36.2 |
3 |
172.5 |
2.24 |
25.1 |
174.5 |
2.24 |
35.8 |
3.75 |
153.4 |
2.19 |
33.4 |
155.7 |
2.19 |
42.7 |
4 |
146.3 |
2.17 |
36.5 |
152.6 |
2.18 |
43.9 |
6.8 |
82.3 |
1.92 |
64.3 |
93.5 |
1.97 |
65.6 |
11 |
49.8 |
1.70 |
78.4 |
54.1 |
1.73 |
80.1 |
The results were used to calculate the half-life (t0.5), applying the Arrhenius relationship. The half-life for the test substance was calculated to be 5 days.
50 °C
The temperature during the test varied between 49.8 and 49.9°C. The pH of the buffer solution was checked at the start of the test and was measured to be 4.0. After 24 hours between 86 and 87% of hydrolysis of the test substance was observed.
Time hr. |
Replicate I |
Replicate II |
||||
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
|
0 |
294.0 |
2.47 |
0.0 |
294.1 |
2.47 |
0.0 |
1 |
263.3 |
2.42 |
10.4 |
268.9 |
2.43 |
8.6 |
2 |
231.6 |
2.36 |
21.2 |
229.6 |
2.36 |
21.9 |
3 |
208.8 |
2.32 |
29.0 |
212.3 |
2.33 |
27.8 |
4 |
200.5 |
2.30 |
31.8 |
193.5 |
2.29 |
34.2 |
5.5 |
164.6 |
2.22 |
44.0 |
168.2 |
2.23 |
42.8 |
7 |
128.5 |
2.11 |
56.3 |
152.2 |
2.18 |
48.3 |
24 |
41.6 |
1.62 |
85.9 |
39.0 |
1.59 |
86.7 |
The results were used to calculate the half-life (t0.5), applying the Arrhenius relationship. The half-life for the test substance was calculated to be 9 hours.
Using the determined half-lives at the different test temperatures an interpolation curve was composed. Using the equation of this interpolation curve the half-life at a temperature of 25°C was calculated to be 10 days.
pH value |
Temperature °C |
Replicate |
slope |
Kobs |
t1/2days |
|
pH 4 |
10 |
I |
* |
* |
|
* |
II |
-0.0038 |
0.00875 |
days-1 |
79 |
||
Mean |
79 |
|||||
30 |
I |
-0.0643 |
0.14806 |
days-1 |
5 |
|
II |
-0.0621 |
0.14299 |
days-1 |
5 |
||
Mean |
5 |
|||||
50 |
I |
-0.0348 |
0.08013 |
hr-1 |
0.4 |
|
II |
-0.0359 |
0.08266 |
hr-1 |
0.3 |
||
Mean |
0.4 |
|||||
25 |
interpolated |
10 |
||||
Note: Measuring unit of Kobs and half-life (t½) can be different
* Results of replicate I were unreliable and therefore not used in calculations
pH 7
10 °C
The temperature throughout the test was measured to be 10.0°C. The pH of the buffer solution was checked at the start of the test and was measured to be 7.0. After 31 days about 26% of hydrolysis of the test substance was observed.
Time days |
Replicate I |
Replicate II |
||||
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
|
0 |
294.7 |
2.47 |
0.0 |
293.6 |
2.47 |
0.0 |
3 |
296.0 |
2.47 |
-0.4 |
302.9 |
2.48 |
-3.2 |
5 |
317.6 |
2.50 |
-7.8 |
311.4 |
2.49 |
-6.1 |
10 |
233.1 |
2.37 |
20.9 |
232.5 |
2.37 |
20.8 |
18 |
237.7 |
2.38 |
19.4 |
231.7 |
2.36 |
21.1 |
21.1 |
223.9 |
2.35 |
24.0 |
229.9 |
2.36 |
21.7 |
28 |
218.1 |
2.34 |
26.0 |
236.4 |
2.37 |
19.5 |
31 |
216.8 |
2.34 |
26.4 |
218.6 |
2.34 |
25.5 |
The results were used to calculate the half-life (t0.5), applying the Arrhenius relationship. The half-life for the test substance was calculated to be 63 days.
30 °C
The temperature during the test varied between 29.9 and 30.1°C. The pH of the buffer solution was checked at the start of the test and was measured to be 7.1. After 9 days between 78 and 80% of hydrolysis of the test substance was observed.
Time days |
Replicate I |
Replicate II |
||||
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
|
0 |
352.5 |
2.55 |
0.0 |
398.1 |
2.60 |
0.0 |
0.08 |
367.2 |
2.56 |
-4.2 |
380.6 |
2.58 |
4.4 |
0.17 |
344.5 |
2.54 |
2.3 |
359.6 |
2.56 |
9.7 |
0.25 |
325.3 |
2.51 |
7.7 |
352.0 |
2.55 |
11.6 |
1 |
341.6 |
2.53 |
3.1 |
323.5 |
2.51 |
18.7 |
2 |
305.4 |
2.48 |
13.3 |
334.0 |
2.52 |
16.1 |
3 |
272.4 |
2.44 |
22.7 |
271.7 |
2.43 |
31.8 |
4 |
243.9 |
2.39 |
30.8 |
228.1 |
2.36 |
42.7 |
7.2 |
128.4 |
2.11 |
63.6 |
106.0 |
2.03 |
73.4 |
9 |
77.8 |
1.89 |
77.9 |
80.3 |
1.90 |
79.8 |
The results were used to calculate the half-life (t0.5), applying the Arrhenius relationship. The half-life for the test substance was calculated to be 4 days.
50 °C
The temperature during the test varied between 49.8 and 49.9°C. The pH of the buffer solution was checked at the start of the test and was measured to be 7.1. After 24 hours between 86 and 87% of hydrolysis of the test substance was observed.
Time hr. |
Replicate I |
Replicate II |
||||
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
|
0 |
299.1 |
2.48 |
0.0 |
314.1 |
2.50 |
0.0 |
1 |
272.6 |
2.44 |
8.9 |
293.4 |
2.47 |
6.6 |
2 |
244.5 |
2.39 |
18.2 |
261.0 |
2.42 |
16.9 |
3 |
229.2 |
2.36 |
23.4 |
239.4 |
2.38 |
23.8 |
4 |
209.4 |
2.32 |
30.0 |
216.0 |
2.33 |
31.2 |
5.5 |
185.0 |
2.27 |
38.1 |
193.4 |
2.29 |
38.4 |
7 |
138.8 |
2.14 |
53.6 |
171.1 |
2.23 |
45.5 |
24 |
40.9 |
1.61 |
86.3 |
42.2 |
1.63 |
86.6 |
The results were used to calculate the half-life (t0.5), applying the Arrhenius relationship. The half-life for the test substance was calculated to be 8 hours.
Using the determined half-lives at the different test temperatures an interpolation curve was composed. Using the equation of this interpolation curve the half-life at a temperature of 25°C was calculated to be 9 days.
pH value |
Temperature °C |
Replicate |
slope |
Kobs |
t1/2 days |
|
pH 7 |
10 |
I |
-0.0051 |
0.01174 |
days-1 |
59 |
II |
-0.0045 |
0.01036 |
days-1 |
67 |
||
Mean |
63 |
|||||
30 |
I |
-0.0752 |
0.17315 |
days-1 |
4 |
|
II |
-0.0683 |
0.15727 |
days-1 |
4 |
||
Mean |
4 |
|||||
50 |
I |
-0.0359 |
0.08266 |
days-1 |
0.3 |
|
II |
-0.0362 |
0.08335 |
days-1 |
0.3 |
||
Mean |
0.3 |
|||||
25 |
interpolated |
9 |
||||
Note: Measuring unit of Kobs and half-life (t½) can be different
pH 9
10 °C
The temperature during the test varied between 9.8 and 10.0°C. The pH of the buffer solution was checked at the start of the test and was measured to be 9.1. After 30 days between 79 and 80% of hydrolysis of the test substance was observed.
Time days |
Replicate I |
Replicate II |
||||
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
|
0 |
299.6 |
2.48 |
0.0 |
281.1 |
2.45 |
0.0 |
1.1 |
268.4 |
2.43 |
10.4 |
271.4 |
2.43 |
3.4 |
3 |
249.9 |
2.40 |
16.6 |
257.5 |
2.41 |
8.4 |
8 |
175.8 |
2.24 |
41.3 |
193.0 |
2.29 |
31.3 |
11.1 |
144.7 |
2.16 |
51.7 |
155.2 |
2.19 |
44.8 |
14 |
116.1 |
2.06 |
61.3 |
138.5 |
2.14 |
50.7 |
17 |
100.6 |
2.00 |
66.4 |
119.5 |
2.08 |
57.5 |
21.1 |
89.8 |
1.95 |
70.0 |
86.6 |
1.94 |
69.2 |
24 |
53.4 |
1.73 |
82.2 |
63.8 |
1.80 |
77.3 |
30.1 |
60.8 |
1.78 |
79.7 |
59.1 |
1.77 |
79.0 |
The results were used to calculate the half-life (t0.5), applying the Arrhenius relationship. The half-life for the test substance was calculated to be 12 days.
30 °C
The temperature during the test varied between 29.9 and 30.0°C. The pH of the buffer solution was checked at the start of the test and was measured to be 9.0. After 53 hours between 83 and 84% of hydrolysis of the test substance was observed.
Time hr. |
Replicate I |
Replicate II |
||||
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
|
0 |
297.0 |
2.47 |
0.0 |
309.8 |
2.49 |
0.0 |
2 |
305.0 |
2.48 |
-2.7 |
285.1 |
2.45 |
8.0 |
4 |
284.8 |
2.45 |
4.1 |
281.2 |
2.45 |
9.2 |
23 |
144.5 |
2.16 |
51.3 |
146.5 |
2.17 |
52.7 |
26 |
106.0 |
2.03 |
64.3 |
122.6 |
2.09 |
60.4 |
29 |
102.1 |
2.01 |
65.6 |
118.5 |
2.07 |
61.7 |
47 |
77.0 |
1.89 |
74.1 |
78.0 |
1.89 |
74.8 |
50 |
53.6 |
1.73 |
81.9 |
64.5 |
1.81 |
79.2 |
53 |
46.3 |
1.67 |
84.4 |
51.7 |
1.71 |
83.3 |
The results were used to calculate the half-life (t0.5), applying the Arrhenius relationship. The half-life for the test substance was calculated to be 21 hours.
50 °C
The temperature during the test varied between 49.8 and 50.0°C. The pH of the buffer solution was checked at the start of the test and was measured to be 9.0. After 6 hours about 81% of hydrolysis of the test substance was observed.
Time hr. |
Replicate I |
Replicate II |
||||
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
Concentration (Ct) mg/L |
Log Ct |
Hydrolysis % |
|
0 |
293.0 |
2.47 |
0.0 |
286.5 |
2.46 |
0.0 |
0.5 |
251.4 |
2.40 |
14.2 |
259.2 |
2.41 |
9.5 |
1 |
224.3 |
2.35 |
23.4 |
228.3 |
2.36 |
20.3 |
1.5 |
201.6 |
2.30 |
31.2 |
194.7 |
2.29 |
32.0 |
2 |
178.0 |
2.25 |
39.2 |
173.3 |
2.24 |
39.5 |
3 |
114.2 |
2.06 |
61.0 |
113.6 |
2.06 |
60.3 |
4 |
90.2 |
1.96 |
69.2 |
87.1 |
1.94 |
69.6 |
5 |
71.1 |
1.85 |
75.7 |
68.3 |
1.83 |
76.1 |
6 |
57.0 |
1.76 |
80.5 |
54.0 |
1.73 |
81.2 |
The results were used to calculate the half-life (t0.5), applying the Arrhenius relationship. The half-life for the test substance was calculated to be 2 hours.
Using the determined half-lives at the different test temperatures an interpolation curve was composed. Using the equation of this interpolation curve the half-life at a temperature of 25°C was calculated to be 45 hours.
pH value |
Temperature °C |
Replicate |
slope |
Kobs |
t1/2 days |
|
pH 9 |
10 |
I |
-0.0254 |
0.05849 |
days-1 |
284 |
II |
-0.0245 |
0.05641 |
days-1 |
295 |
||
Mean |
290 |
|||||
30 |
I |
-0.0149 |
0.03431 |
hr-1 |
20 |
|
II |
-0.0138 |
0.03178 |
hr-1 |
22 |
||
Mean |
21 |
|||||
50 |
I |
-0.1228 |
0.28276 |
hr-1 |
2 |
|
II |
-0.1268 |
0.29197 |
hr-1 |
2 |
||
Mean |
2 |
|||||
25 |
interpolated |
45 |
||||
Additional experiment
The additional experiment was carried out for pH value 1.2 at 37°C. Results are described below.
Time hours |
Concentration (Ct) mg/L |
Hydrolysis % |
0 |
241.5 |
0.0 |
0.5 |
234.4 |
3.0 |
1 |
212.3 |
12.1 |
2 |
204.9 |
15.2 |
4 |
208.7 |
13.6 |
6 |
196.8 |
18.5 |
The temperature throughout the test was measured to be 37.0°C. The pH of the buffer solution was checked at the start of the test and was measured to be 1.2.
Description of key information
The purpose of this study was to determine if tert-butylperoxyisopropylcarbonate
would hydrolyze at environmentally and physiologically relevant pH values, complying with the OECD Guideline No. 111. Hydrolysis of tert-pentyl peroxypivalate was observed at pH values 4, 7 and 9.
At pH value 4 the half-life (t0.5) for tert-pentyl peroxypivalate at a temperature of 25°C was calculated to be 10 days.
At pH value 7 the half-life (t0.5) for tert-pentyl peroxypivalate at a temperature of 25°C was calculated to be 9 days.
At pH value 9 the half-life (t0.5) for tert-pentyl peroxypivalate at a temperature of 25°C was calculated to be 45 hours.
No hydrolysis products were identified during the study, because hydrolysis was not fast enough to take this into account.
Key value for chemical safety assessment
- Half-life for hydrolysis:
- 9 d
- at the temperature of:
- 25 °C
Additional information
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