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Environmental fate & pathways

Hydrolysis

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Endpoint:
hydrolysis
Type of information:
experimental study
Adequacy of study:
key study
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
other: The study was conducted according to the OECD Guideline no 111 and in compliance to GLP
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:
Details on properties of test surrogate or analogue material (migrated information):
NA
Radiolabelling:
no
Analytical monitoring:
yes
Details on sampling:
At each sampling time, two samples were removed from the bath and an aliquot (1 ml) of each was diluted to volume (10 ml) with mobile phase for analysis by high performance liquid chromatography (HPLC).
Buffers:
Buffer solutions were prepared as follows:
pH 4: 0.2M aqueous potassium dihydrogen orthophosphate (550 ml) was mixed with
0.07M aqueous disodium hydrogen orthophosphate dodecahydrate (1250 ml) and purified water (3200 ml). The pH was adjusted to 4.0 +/- 0.05 with orthophosphoric acid.

pH 7: 0.2M aqueous potassium dihydrogen orthophosphate (1250 ml) was mixed with
1M sodium hydroxide (150 ml) and purified water (3600 ml). The pH was adjusted to
7.0 +/- 0.05 with 1M sodium hydroxide.

pH 9: 0.1M boric acid in 0.1M aqueous potassium chloride (2000 ml) was mixed with
1M sodium hydroxide (84 ml) and purified water (1920 ml). The pH was measured as
9.0 +/-0.05.
Duration:
120 h
pH:
9
Temp.:
50
Duration:
120 h
pH:
7
Temp.:
50
Duration:
120 h
pH:
4
Temp.:
50
Number of replicates:
Na
Positive controls:
not specified
Negative controls:
not specified
Statistical methods:
Na
Preliminary study:
The study was a preliminary study
Test performance:
NA
Transformation products:
not specified
Details on hydrolysis and appearance of transformation product(s):
na
pH:
4
Temp.:
25 °C
DT50:
>= 1 yr
pH:
7
Temp.:
25 °C
DT50:
ca. 1 yr
Remarks on result:
other: half life less than 1 year
pH:
9
Temp.:
25 °C
DT50:
ca. 1 yr
Remarks on result:
other: half life less than 1 year
Other kinetic parameters:
NA
Details on results:
Preliminary test results
Ct (mg/l)

pH t = 0h t = 2.4h t = 72h t = 120h
Measured Mean Measured Mean Measured Mean Measured Mean

4 209, 206 208 204, 206 205 208, 212 210 196, 201 199

7 203, 209 206 202, 203 202 163, 163 163 142, 139 140

9 197, 211 204 127, 133 130 - , - - - , - -

During the study there were no significant changes in pH and temperature with time.

Linearity:
Using the conditions described, the calibration of MIRAMER M140 was found to be linear over the concentration range 0 to 40 mg/l, with a regression coefficient of 1.0000.
It was considered that the analytical method was sufficiently sensitive to quantify test substance concentrations down to 10% or less of the initial concentration.

Preliminary test:
The preliminary study showed that at pH 4 and 50 +/- 0.5ºC, less than 10% hydrolysis had occurred after 5 days, equivalent to a half-life of greater than 1 year under environmental conditions (25°C).
At each of pH 7 and 9 and 50 +/- 0.5ºC, more than 10% hydrolysis had occurred after 5 days, equivalent to a half-life of less than 1 year under environmental conditions (25°C).


NA

Validity criteria fulfilled:
not specified
Conclusions:
A study was performed to determine the rate of hydrolysis of MIRAMER M140 as a function of pH. The test was conducted in accordance with the preliminary test as described in Commission Regulation (EC) No. 440/2008 (Method C.7) and the OECD Guidelines for Testing of Chemicals (Method 111). MIRAMER M140 was determined to be hydrolytically stable under acidic conditions, but unstable under neutral and basic conditions.
Executive summary:

A study was performed to determine the rate of hydrolysis of 2-phenoxyethyl acrylate as a function of pH. The test was conducted in accordance with the preliminary test as described in Commission Regulation (EC) No. 440/2008 (Method C.7) and the OECD Guidelines for Testing of Chemicals (Method 111).

The preliminary study showed that at pH 4 and 50 +/- 0.5ºC, less than 10% hydrolysis had occurred after 5 days, equivalent to a half-life of greater than 1 year under environmental conditions (25°C).

At each of pH 7 and 9 and 50 +/- 0.5ºC, more than 10% hydrolysis had occurred after 5 days, equivalent to a half-life of less than 1 year under environmental conditions (25°C). 2-phenoxyethyl acrylate was determined to be hydrolytically stable under acidic conditions, but unstable under neutral and basic conditions.

Endpoint:
hydrolysis
Type of information:
read-across from supporting substance (structural analogue or surrogate)
Adequacy of study:
key study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Read-across to study with reliability (1) + QSAR analysis
Justification for type of information:
Read-across from a hydrolysis study on one closely structural and physicochemical related substance: 2-Phenoxyethyl acrylate (M140).
For further read-across justification se document attached in section 13.
Reason / purpose for cross-reference:
read-across source
Reason / purpose for cross-reference:
read-across source
Transformation products:
not specified
pH:
4
Temp.:
25 °C
DT50:
>= 1 yr
pH:
7
Temp.:
25 °C
DT50:
ca. 1 yr
Remarks on result:
other: Half-life less than 1 year
pH:
9
Temp.:
25 °C
DT50:
ca. 4 d
Type:
(pseudo-)first order (= half-life)
Remarks on result:
other: half-life less than 1 year
Validity criteria fulfilled:
not applicable
Conclusions:
No data is available for Biphenyl-2-ol, ethoxylated, esters with acrylic acid (M1142) (T).

The rate of hydrolysis of 2-phenoxyethyl acrylate was evaluated as a function of pH. And conducted in accordance with the preliminary test as described in Commission Regulation (EC) No. 440/2008 (Method C.7) and the OECD Guidelines for Testing of Chemicals (Method 111).
At each of pH 7 and 9 and 50 +/- 0.5ºC, more than 10% hydrolysis had occurred after 5 days, equivalent to a half-life of less than 1 year under environmental conditions (25°C). 2-phenoxyethyl acrylate was determined to be hydrolytically stable under acidic conditions, but unstable under neutral and basic conditions.
 
Based on to structural and pysico-chemical similarity to Biphenyl-2-ol, ethoxylated, esters with acrylic acid and QSAR calculations, a half-life of about one year at 25°C can be concluded for Biphenyl-2-ol, ethoxylated, esters with acrylic acid as well.
Executive summary:

No data is available for Biphenyl-2-ol, ethoxylated, esters with acrylic acid (M1142) (T).

The rate of hydrolysis of 2-phenoxyethyl acrylate was evaluated as a function of pH. And conducted in accordance with the preliminary test as described in Commission Regulation (EC) No. 440/2008 (Method C.7) and the OECD Guidelines for Testing of Chemicals (Method 111).

At each of pH 7 and 9 and 50 +/- 0.5ºC, more than 10% hydrolysis had occurred after 5 days, equivalent to a half-life of less than 1 year under environmental conditions (25°C). 2-phenoxyethyl acrylate was determined to be hydrolytically stable under acidic conditions, but unstable under neutral and basic conditions.

 

Based on to structural and pysico-chemical similarity to Biphenyl-2-ol, ethoxylated, esters with acrylic acid and QSAR calculations, a half-life of about one year at 25°C can be concluded for Biphenyl-2-ol, ethoxylated, esters with acrylic acid as well.

See justification for read-across attached in section 13.

Endpoint:
hydrolysis
Type of information:
(Q)SAR
Adequacy of study:
supporting study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Estimate by SPARC using SMILES notation for the substance. Result in compliance with screening study (hydrolytic half-life < 1 year at pH=7).
Justification for type of information:
QSAR prediction
Reason / purpose for cross-reference:
reference to same study
Qualifier:
no guideline followed
GLP compliance:
no
Analytical monitoring:
no
Transformation products:
not measured
No.:
#1
No.:
#2

Description of key information

A study was performed to determine the rate of hydrolysis of MIRAMER M140 as a function of pH. The test was conducted in accordance with the preliminary test as described in Commission Regulation (EC) No. 440/2008 (Method C.7) and the OECD Guidelines for Testing of Chemicals (Method 111).. The study was conducted in compliance with GLP.

Key value for chemical safety assessment

Half-life for hydrolysis:
1 yr
at the temperature of:
25 °C

Additional information

A preliminary study showed that at pH 4 and 50 +/- 0.5ºC, less than 10% hydrolysis had occurred after 5 days, equivalent to a half-life of greater than 1 year under environmental conditions (25°C).

At each of pH 7 and 9 and 50 +/- 0.5ºC, more than 10% hydrolysis had occurred after 5 days, equivalent to a half-life of less than 1 year under environmental conditions (25°C). MIRAMER M140 was determined to be hydrolytically stable under acidic conditions, but unstable under neutral and basic conditions. Estimation by SPARC using SMILES notation for the substance gave a hydrolytic half-life =150 d at pH=7, which is is in compliance with screening study (hydrolytic half-life < 1 year at pH=7).

No data is available for Biphenyl-2-ol, ethoxylated, esters with acrylic acid (M1142) (T).

Based on to structural and pysico-chemical similarity to Biphenyl-2-ol, ethoxylated, esters with acrylic acid and QSAR calculations, a half-life of about one year at 25°C at pH=7 can be concluded for Biphenyl-2-ol, ethoxylated, esters with acrylic acid as well.