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Environmental fate & pathways

Hydrolysis

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Reference
Endpoint:
hydrolysis
Type of information:
experimental study
Adequacy of study:
key study
Study period:
2016-01-19
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
comparable to guideline study
Qualifier:
equivalent or similar to guideline
Guideline:
OECD Guideline 111 (Hydrolysis as a Function of pH)
Principles of method if other than guideline:
- Principle of test:
The test item was dissolved in organic solvent and added to buffer solutions (pH 4, 7 and 9). The solutions were agitated for 0, 1, 2, 3 and 6 days. Samples were taken at each time point and the area of the parent compound and the hydrolysis products were investigated by LC-MS analysis.

In addition a seperate trial with the hydrolysis product using the same condition was performed.

- Parameters analysed / observed: change of the % Area of the parent compound and the hydrolysis products in the LC MS chromatogram at different time points and identification of the hydrolysis products.


GLP compliance:
no
Remarks:
The study was conducted under supervision of a quality assurance unit which had ensured e.g instrumentation validation, reagent/materials certification, analyst certification and providing standard operating procedures.
Radiolabelling:
no
Analytical monitoring:
yes
Details on sampling:
- Sampling method:
For FIMS method : Approx. 100 mg of the test item were added to 5 mL ACN. 25 μL of the test item solution were added to 5 mL of buffer solution. At a constant carrier flow of 400 μL/min (solvent: ACN) the sample solutions (100 μg/mL) were injected by a 500 μL syringe (10 μL/min) directly into the mass spectrometer (atmospheric pressure chemical ionization source).

For LC-MS method the test item (334 mg) was dissolved in 10 mL ACN. Then 150 μL of the test item solution were added to 10 mL of buffer solution (pH 4, 7 and 9).
Buffers:
- pH: 4, 7, 9
- Composition of buffer:
pH 4: 5.7 g ammonium formate and 1.885 mL (0.1 M) of formic acid were dissolved and diluted to 500 mL with ultra-pure water. The pH value was adjusted with formic acid to pH 4.03 (degassed with argon).
pH 7: ultra-pure water, measured after degassing with argon pH: 6.8.
pH 9: 3.2 g ammonium formate (0.1 M) and 2.0 mL ammonia solution (25 %) were dissolved and diluted to 500 mL with ultra-pure water. The pH value was adjusted with formic acid to pH 9.04 (degassed with argon).

The pH of each buffer solution was checked with a calibrated pH meter.
Details on test conditions:
TEST SYSTEM
- Type, material and volume of test flasks, other equipment used:
The qualitative FIMS measurements were performed at different times to observe the progress of the hydrolysis: after 2 minutes (initial measurement) up to 6 days after the test item / hydrolysis products were exposed to the aqueous buffer solutions.

The semi-quantitative LC-MS measurements were performed at different times to observe the progress of the hydrolysis: after approx. 1 hour (initial measurement); then 1, 2, 3 and 6 days after the test item / hydrolysis product were exposed to the aqueous buffer solutions.

Duration:
144 h
pH:
4
Temp.:
22 °C
Remarks:
no initial concentration was measured, the change of area % over time was investigated
Duration:
144 h
pH:
7
Temp.:
22 °C
Remarks:
no initial concentration was measured, the change of area % over time was investigated
Duration:
144 h
pH:
9
Temp.:
22 °C
Remarks:
no initial concentration was measured, the change of area % over time was investigated
Number of replicates:
1
Positive controls:
no
Negative controls:
no
Test performance:
For FIMS method : Approx. 100 mg of the test item were added to 5 mL ACN. 25 μL of the test item solution were added to 5 mL of buffer solution. At a constant carrier flow of 400 μL/min (solvent: ACN) the sample solutions (100 μg/mL) were injected by a 500 μL syringe (10 μL/min) directly into the mass spectrometer (atmospheric pressure chemical ionization source).

For LC-MS method The test item (334 mg) was dissolved in 10 mL ACN. Then 150 μL of the test item solution were added to 10 mL of buffer solution (pH 4, 7 and 9). The test item solution were agitated for 1 h, 1, 2 3 and 6 days.
Transformation products:
yes
No.:
#1
No.:
#2
% Recovery:
0
pH:
4
Temp.:
22 °C
Duration:
24 h
% Recovery:
62
pH:
7
Temp.:
22 °C
Duration:
24 h
% Recovery:
61
pH:
7
Temp.:
22 °C
Duration:
48 h
% Recovery:
54
pH:
7
Temp.:
22 °C
Duration:
72 h
% Recovery:
42
pH:
7
Temp.:
22 °C
Duration:
144 h
% Recovery:
29
pH:
9
Temp.:
22 °C
Duration:
24 h
% Recovery:
0
pH:
9
Temp.:
22 °C
Duration:
48 h
Key result
pH:
4
Temp.:
22 °C
Remarks on result:
not measured/tested
Key result
pH:
7
Temp.:
22 °C
Remarks on result:
not measured/tested
Key result
pH:
9
Temp.:
22 °C
Remarks on result:
not measured/tested
Details on results:
TEST CONDITIONS
- pH, sterility, temperature, and other experimental conditions maintained throughout the study: Yes

MAJOR TRANSFORMATION PRODUCTS
At pH4, 7 and 9:
2,2-Dimethyl-3-lauroyloxy-propanal and p-phenylenediamine.

MINOR TRANSFORMATION PRODUCTS
Maximum concentrations in % of the applied amount
- at pH4, 7 and 9:
Hydrolysed and mono amidated test item, mono hydrolysied and amidated test item.

INDICATION OF UNSTABLE TRANSFORMATION PRODUCTS:
The transformation products 2,2-Dimethyl-3-lauroyloxy-propanal and p-phenylenediamine were determined to be unstable during the test period and undergoes further transformation.

PATHWAYS OF HYDROLYSIS
- Description of pathway (in general): Protonation of the imine nitrogen results in the formation of the iminium ion, which undergoes 1,2-addition by water. Transfer of a proton followed by 1,2 elimination of ammonia lead to an oxonium ion, which is then deprotonated to give the neutral aldehyde.

- Figures of chemical structures attached: Yes

Please refer to the attached background material for detailed structural information.

According to the FIMS results the test item hydrolyzes within a few hours at pH 4. The semi-quantitative LC-MS measurements compare the integrated peaks relative to the initial measurement (rel. changes in area-%):

 

Component

1(area-%)

2(area-%)

3(area-%)

4(area-%)

5(area-%)

6(area-%)

After 1 day

+4

-44

-41

-41

-100

-100

After 2 days

+13

+28

+36

+19

-100

-100

After 3 days

-13

+25

+7

+27

-100

-100

After 6 days

-12

-57

-75

-46

-100

-100

 

According to FIMS and LC-MS results the test item hydrolyzes very slowly at pH 7. The table below

compares the integrated peaks relative to the initial measurement (relative area-%) for the hydrolysis at pH 7:

 

Component

1(area-%)

2(area-%)

3(area-%)

4(area-%)

5(area-%)

6(area-%)

After 1 day

+101

+30

-35

-16

-15

-38

After 2 days

+93

+4

-40

-29

-19

-39

After 3 days

+93

+31

-45

-16

-26

-46

After 6 days

+63

+20

-58

-7

-37

-58

 

According to FIMS and LC-MS results the Sika Hardener LPP hydrolyzes slowly at pH 9. The table below compares

the integrated peaks relative to the initial measurement (relative area-%) for the hydrolysis at pH 9

 

Component

1(area-%)

2(area-%)

3(area-%)

4(area-%)

5(area-%)

6(area-%)

After 1 day

+74

+209

-47

+3

-64

-71

After 2 days

+20

-9

-98

-33

-100

-100

After 3 days

+24

+76

-97

-3

-100

-100

After 6 days

-23

+12

-99

-36

-100

-100

 

Please refer to the attached background material for structural information of the components.

In order to detect the degradation of the 2,2-Dimethyl-3-lauroyloxy-propanal and its degradation products a LC-MS run set in the positive ion mode was performed to detect the positively charged components as [MH]+-adducts. According to LC-MS results the 2,2-Dimethyl-3-lauroyloxy-propanal hydrolyzes slowly at pH 4 and 9. At pH 7 no significant hydrolysis was observed. The table below compares the integrated peaks relative to the initial measurement (relative area-%) for the hydrolysis at pH 4, 7 and 9:

 

Component

pH 4

pH 7

pH 9

After 1 day

+64

+37

-13

After 2 days

+14

+163

-32

After 3 days

-68

+68

(+16)

After 6 days

-78

+32

-64

 

Validity criteria fulfilled:
not applicable
Conclusions:
The hydrolysis of the test item in different aqueous buffer solutions (pH = 4, 7 and 9) at 22±2 °C was investigated using FIMS-MS and LC-MS. Measurements revealed a fast hydrolysis of the test item at pH = 4 and 9 and 22 °C and slow hydrolysis at pH 7. The degradation products of the hydrolysis of the test item (2,2-Dimethyl-3-lauroyloxy-propanal and 2,2-dimethyl-3-oxopropyl dodecanoate) were identified qualitatively using FIMS-MS and LC-MS, respectively.
Executive summary:

The hydrolysis of the test item and the identification of the decomposition products were assessed in a study similar to the OECD guideline 111 and the EU method C.7. The hydrolysis of the test item in different aqueous buffer solutions (pH = 4, 7 and 9) at 22 ± 2°C was investigated using FIMS-MS and LC-MS. Measurements revealed a fast hydrolysis of the test item at pH = 4 and 9 and 22 °C and slow hydrolysis at pH 7. The degradation products of the hydrolysis of the test item (2,2-Dimethyl-3-lauroyloxy-propanal and 2,2-dimethyl-3-oxopropyl dodecanoate) were identified qualitatively using FIMS-MS and LC-MS, respectively. In addition the hydrolysis of the degradation product of the test item 2,2-dimethyl-3-oxopropyl dodecanoate was investigated. It was shown that 2,2-dimethyl-3-oxopropyl dodecanoate hydrolyzes slowly at pH 4 and 9. At pH 7 no significant hydrolysis was observed. It could be shown that the hydrolysis of the test item was dependent from the pH.

It was concluded that the similar key results will be obtained when conducting the study at 50 °C (as prescribed by the OECD guideline) as higher temperatures accelerate hydrolysis. Thus, this deviation was considered to have no impact on the outcome of the study.

Description of key information

The hydrolysis of the test item in different aqueous buffer solutions (pH = 4, 7 and 9) at 22±2 °C was investigated using FIMS-MS and LC-MS. Measurements revealed a fast hydrolysis of the test item at pH = 4 and 9 and 22 °C and slow hydrolysis at pH 7. The degradation products of the hydrolysis of the test item (2,2-Dimethyl-3-lauroyloxy-propanal and 2,2-dimethyl-3-oxopropyl dodecanoate) were identified qualitatively using FIMS-MS and LC-MS, respectively.

Key value for chemical safety assessment

Additional information

The hydrolysis of the test item and the identification of the decomposition products were assessed in a study similar to the OECD guideline 111 and the EU method C.7. The hydrolysis of the test item in different aqueous buffer solutions (pH = 4, 7 and 9) at 22 ± 2°C was investigated using FIMS-MS and LC-MS. Measurements revealed a fast hydrolysis of the test item at pH = 4 and 9 and 22 °C and slow hydrolysis at pH 7. The degradation products of the hydrolysis of the test item (2,2-Dimethyl-3-lauroyloxy-propanal and 2,2-dimethyl-3-oxopropyl dodecanoate) were identified qualitatively using FIMS-MS and LC-MS, respectively. In addition the hydrolysis of the degradation product of the test item 2,2-dimethyl-3-oxopropyl dodecanoate was investigated. It was shown that 2,2-dimethyl-3-oxopropyl dodecanoate hydrolyzes slowly at pH 4 and 9. At pH 7 no significant hydrolysis was observed. It could be shown that the hydrolysis of the test item was dependent from the pH.

It was concluded that the similar key results will be obtained when conducting the study at 50 °C (as prescribed by the OECD guideline) as higher temperatures accelerate hydrolysis. Thus, this deviation was considered to have no impact on the outcome of the study.