Dodecyl acrylate

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

supporting study

Justification for type of information:

REPORTING FORMAT FOR THE ANALOGUE APPROACH

1. HYPOTHESIS FOR THE ANALOGUE APPROACH
This read-across justification is based on the hypothesis that Dodecyl acrylate and the source chemicals 2-ethylhexyl acrylate, 2-propylheptyl acrylate, 2-Propenoic acid, C12-14-alkyl esters, 2-Propenoic acid, C16-18-alkyl esters and 2-Propenoic acid, C18-22-alkyl esters have similar properties because they are long-chain esters containing lengths of C7 - C22 alkyl chains or mixtures thereof, share a common ester-structure and are all acrylates derived from acrylic acid. Additionally, the common hydrolysis product of target and source substances is acrylic acid and the corresponding alcohol of different chain length.

2. SOURCE AND TARGET CHEMICAL(S) (INCLUDING INFORMATION ON PURITY AND IMPURITIES)
- Purity of the target substance: > 99.9 % ≤ 100 %
- Purity of 2-ethylhexyl acrylate: ≥ 99.6 % < 99.9 %
- Purity of 2-propylheptyl acrylate: > 87.0 % < 96.0 %
- Purity of 2-Propenoic acid, C12-14-alkyl esters: 93.9 %
- Purity of 2-Propenoic acid, C16-18-alkyl esters: ≥ 95.1 % > 98 %
- Purity of 2-Propenoic acid, C18-22-alkyl esters: 93.7 %

3. ANALOGUE APPROACH JUSTIFICATION
Read-across to the source substances is considered to be applicable for Dodecyl acrylate, because target and source substances share a common ester-structure and are all acrylates derived from acrylic acid. The results of the investigated endpoints are in accordance. Sufficient data are available to characterize properties and trends for the source substances. As a rule, melting point, boiling point and octanol / water partition coefficient increase, and vapour pressure and water solubility decrease, with increasing molecular weight / volume (i.e. alkyl ester group) within the series. With respect to structural similarity between target and source substances as well as between the results of investigations in the studies, the source substances are considered to be suitable for read-across.

4. DATA MATRIX
Please refer to section 13.

Reason / purpose for cross-reference:

read-across source

Parameter:

% degradation (CO2 evolution)

Value:

70 - 80

Sampling time:

15 d

Reference 2

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

supporting study

Justification for type of information:

REPORTING FORMAT FOR THE ANALOGUE APPROACH

1. HYPOTHESIS FOR THE ANALOGUE APPROACH
This read-across justification is based on the hypothesis that Dodecyl acrylate and the source chemicals 2-ethylhexyl acrylate, 2-propylheptyl acrylate, 2-Propenoic acid, C12-14-alkyl esters, 2-Propenoic acid, C16-18-alkyl esters and 2-Propenoic acid, C18-22-alkyl esters have similar properties because they are long-chain esters containing lengths of C7 - C22 alkyl chains or mixtures thereof, share a common ester-structure and are all acrylates derived from acrylic acid. Additionally, the common hydrolysis product of target and source substances is acrylic acid and the corresponding alcohol of different chain length.

2. SOURCE AND TARGET CHEMICAL(S) (INCLUDING INFORMATION ON PURITY AND IMPURITIES)
- Purity of the target substance: > 99.9 % ≤ 100 %
- Purity of 2-ethylhexyl acrylate: ≥ 99.6 % < 99.9 %
- Purity of 2-propylheptyl acrylate: > 87.0 % < 96.0 %
- Purity of 2-Propenoic acid, C12-14-alkyl esters: 93.9 %
- Purity of 2-Propenoic acid, C16-18-alkyl esters: ≥ 95.1 % > 98 %
- Purity of 2-Propenoic acid, C18-22-alkyl esters: 93.7 %

3. ANALOGUE APPROACH JUSTIFICATION
Read-across to the source substances is considered to be applicable for Dodecyl acrylate, because target and source substances share a common ester-structure and are all acrylates derived from acrylic acid. The results of the investigated endpoints are in accordance. Sufficient data are available to characterize properties and trends for the source substances. As a rule, melting point, boiling point and octanol / water partition coefficient increase, and vapour pressure and water solubility decrease, with increasing molecular weight / volume (i.e. alkyl ester group) within the series. With respect to structural similarity between target and source substances as well as between the results of investigations in the studies, the source substances are considered to be suitable for read-across.

4. DATA MATRIX
Please refer to section 13.

Reason / purpose for cross-reference:

read-across source

Parameter:

% degradation (CO2 evolution)

Value:

60 - <= 70

Sampling time:

28 d

Reference 3

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

weight of evidence

Justification for type of information:

REPORTING FORMAT FOR THE ANALOGUE APPROACH

1. HYPOTHESIS FOR THE ANALOGUE APPROACH
This read-across justification is based on the hypothesis that Dodecyl acrylate and the source chemicals 2-ethylhexyl acrylate, 2-propylheptyl acrylate, 2-Propenoic acid, C12-14-alkyl esters, 2-Propenoic acid, C16-18-alkyl esters and 2-Propenoic acid, C18-22-alkyl esters have similar properties because they are long-chain esters containing lengths of C7 - C22 alkyl chains or mixtures thereof, share a common ester-structure and are all acrylates derived from acrylic acid. Additionally, the common hydrolysis product of target and source substances is acrylic acid and the corresponding alcohol of different chain length.

2. SOURCE AND TARGET CHEMICAL(S) (INCLUDING INFORMATION ON PURITY AND IMPURITIES)
- Purity of the target substance: > 99.9 % ≤ 100 %
- Purity of 2-ethylhexyl acrylate: ≥ 99.6 % < 99.9 %
- Purity of 2-propylheptyl acrylate: > 87.0 % < 96.0 %
- Purity of 2-Propenoic acid, C12-14-alkyl esters: 93.9 %
- Purity of 2-Propenoic acid, C16-18-alkyl esters: ≥ 95.1 % > 98 %
- Purity of 2-Propenoic acid, C18-22-alkyl esters: 93.7 %

3. ANALOGUE APPROACH JUSTIFICATION
Read-across to the source substances is considered to be applicable for Dodecyl acrylate, because target and source substances share a common ester-structure and are all acrylates derived from acrylic acid. The results of the investigated endpoints are in accordance. Sufficient data are available to characterize properties and trends for the source substances. As a rule, melting point, boiling point and octanol / water partition coefficient increase, and vapour pressure and water solubility decrease, with increasing molecular weight / volume (i.e. alkyl ester group) within the series. With respect to structural similarity between target and source substances as well as between the results of investigations in the studies, the source substances are considered to be suitable for read-across.

4. DATA MATRIX
Please refer to section 13.

Reason / purpose for cross-reference:

read-across source

Parameter:

% degradation (CO2 evolution)

Value:

> 60 - <= 70

Sampling time:

60 d

Reference 4

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

weight of evidence

Justification for type of information:

REPORTING FORMAT FOR THE ANALOGUE APPROACH

1. HYPOTHESIS FOR THE ANALOGUE APPROACH
This read-across justification is based on the hypothesis that Dodecyl acrylate and the source chemicals 2-ethylhexyl acrylate, 2-propylheptyl acrylate, 2-Propenoic acid, C12-14-alkyl esters, 2-Propenoic acid, C16-18-alkyl esters and 2-Propenoic acid, C18-22-alkyl esters have similar properties because they are long-chain esters containing lengths of C7 - C22 alkyl chains or mixtures thereof, share a common ester-structure and are all acrylates derived from acrylic acid. Additionally, the common hydrolysis product of target and source substances is acrylic acid and the corresponding alcohol of different chain length.

2. SOURCE AND TARGET CHEMICAL(S) (INCLUDING INFORMATION ON PURITY AND IMPURITIES)
- Purity of the target substance: > 99.9 % ≤ 100 %
- Purity of 2-ethylhexyl acrylate: ≥ 99.6 % < 99.9 %
- Purity of 2-propylheptyl acrylate: > 87.0 % < 96.0 %
- Purity of 2-Propenoic acid, C12-14-alkyl esters: 93.9 %
- Purity of 2-Propenoic acid, C16-18-alkyl esters: ≥ 95.1 % > 98 %
- Purity of 2-Propenoic acid, C18-22-alkyl esters: 93.7 %

3. ANALOGUE APPROACH JUSTIFICATION
Read-across to the source substances is considered to be applicable for Dodecyl acrylate, because target and source substances share a common ester-structure and are all acrylates derived from acrylic acid. The results of the investigated endpoints are in accordance. Sufficient data are available to characterize properties and trends for the source substances. As a rule, melting point, boiling point and octanol / water partition coefficient increase, and vapour pressure and water solubility decrease, with increasing molecular weight / volume (i.e. alkyl ester group) within the series. With respect to structural similarity between target and source substances as well as between the results of investigations in the studies, the source substances are considered to be suitable for read-across.

4. DATA MATRIX
Please refer to section 13.

Reason / purpose for cross-reference:

read-across source

Parameter:

% degradation (CO2 evolution)

Value:

> 80 - <= 90

Sampling time:

28 d

Reference 5

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

weight of evidence

Justification for type of information:

REPORTING FORMAT FOR THE ANALOGUE APPROACH

1. HYPOTHESIS FOR THE ANALOGUE APPROACH
This read-across justification is based on the hypothesis that Dodecyl acrylate and the source chemicals 2-ethylhexyl acrylate, 2-propylheptyl acrylate, 2-Propenoic acid, C12-14-alkyl esters, 2-Propenoic acid, C16-18-alkyl esters and 2-Propenoic acid, C18-22-alkyl esters have similar properties because they are long-chain esters containing lengths of C7 - C22 alkyl chains or mixtures thereof, share a common ester-structure and are all acrylates derived from acrylic acid. Additionally, the common hydrolysis product of target and source substances is acrylic acid and the corresponding alcohol of different chain length.

2. SOURCE AND TARGET CHEMICAL(S) (INCLUDING INFORMATION ON PURITY AND IMPURITIES)
- Purity of the target substance: > 99.9 % ≤ 100 %
- Purity of 2-ethylhexyl acrylate: ≥ 99.6 % < 99.9 %
- Purity of 2-propylheptyl acrylate: > 87.0 % < 96.0 %
- Purity of 2-Propenoic acid, C12-14-alkyl esters: 93.9 %
- Purity of 2-Propenoic acid, C16-18-alkyl esters: ≥ 95.1 % > 98 %
- Purity of 2-Propenoic acid, C18-22-alkyl esters: 93.7 %

3. ANALOGUE APPROACH JUSTIFICATION
Read-across to the source substances is considered to be applicable for Dodecyl acrylate, because target and source substances share a common ester-structure and are all acrylates derived from acrylic acid. The results of the investigated endpoints are in accordance. Sufficient data are available to characterize properties and trends for the source substances. As a rule, melting point, boiling point and octanol / water partition coefficient increase, and vapour pressure and water solubility decrease, with increasing molecular weight / volume (i.e. alkyl ester group) within the series. With respect to structural similarity between target and source substances as well as between the results of investigations in the studies, the source substances are considered to be suitable for read-across.

4. DATA MATRIX
Please refer to section 13.

Reason / purpose for cross-reference:

read-across source

Parameter:

% degradation (CO2 evolution)

Value:

> 50 - <= 60

Sampling time:

28 d

Description of key information

Biodegradation
Biodegradation in water: screening test (Weight of Evidence approach)

2 -Propenoic aict C12 -14 -alkyl esters
The degree of biodegradation of the test substance was 80-90 %CO2/ThCO2 after an exposure period of 28 days.The test substance is readily biodegradable under the conditions of this test.

2-Propenoic acid, C16-18-alkyl esters
In the Ready Biodegradability (CO2-Evolution) Test the degree of biodegradation of the test substance at the end of exposure was determined to be 50-60 % CO2/ThCO2.
2 -Propenoic acid . C18 -26 -alkyl esters
The degree of biodegradation of the test substance was 60-70 %CO2/ThCO2 after an exposure period of 60 days.The test item was biodegradable under the enhanced test conditions of this test.

2 -Propylheptyl acrylate is considered to be readily biodegradable (60 -70%).

2 -ethylhexyl acrylate is readily biodegradable according to OECD criteria (70 -80%).

Conclusion
Considering the results of the biodegradation studies with Dodecyl acrylate/ Laurylacrylate (C12), 2-Propenoic acid, C16-18-alkyl esters and Icosyl acrylate/ Behenylacrylate (C20) a Weight of Evidence approach was made.
Taking all data together, 2-Propenoic acid, octadecyl ester is considered to be readily biodegradable but failing the 10 - day window.

Key value for chemical safety assessment

Biodegradation in water:

readily biodegradable

Additional information

A Weight of Evidence approach was done with other long-chain acrylates to assess the biodegradation potential of the test substance.

2-Propenoic acid, C16-18-alkyl esters

The Ready Biodegradability (CO2-Evolution) Test to the test substance 2-Propenoic acid, C16-18-alkyl esters was conducted according to the OECD guideline 301B.

The selected test concentration of 20 mg TOC/L corresponds to approximately 26 mg/L test substance. The duration of exposure to the activated sludge was 28 days.Aniline was taken as reference substance.

The test substance was not readily biodegradable in this carbon dioxide evolution test based on the quantitative determination of the formed carbon dioxide in the test substance assays in comparison to the calculated maximal theoretical carbon dioxide production. The required pass level for ready biodegradability was not reached. Because the test substance is a mixture of structure similar compounds the criterion of the ten days window was not applied. Such test substances are multi-component substrates and are typically characterized by different kinetic degradation steps. The degree of biodegradation after an exposure period of 28 days was 50-60 % CO2/ThCO2 in this test. The results in this study are consistent with all validity criteria and the test is valid according to the test guideline of this study. No deviations from the test guidelines or other incidents occurred during the course of the reported test, which may have influenced the results.

 

2 -Propenoic acid, C12 -14-alkyl esters

A biodegradability test of the test substance (2 -Propenoic acid, C12 -14 -alkyl esters) was performed which allows the biodegradability to be measured in an aerobic aqueous medium. The biodegradability was determined in the determination of the biodegradability in the CO2 -Evolution Test performed according to OECD guideline no. 301B. The initial test concentration was 20 mg/L TOC, equivalent to approx. 26 mg/L test substance. The duration of the exposure was 28 days and the test system (inoculum) was activated sludge from the municipal sewage plant Mannheim, Germany. The degree of biodegradation of the test substance was 80 -90 % CO2/ThCO2 after an exposure period of 28 days. That means that the test substance was readily biodegradable under the conditions of this test.

 

2 -Propenoic acid, C18 -26.alkyl esters

A biodegradability test of test substance was performed which allows the biodegradability to be measured in an aerobic aqueous medium. The biodegradability was determined in the determination of the biodegradability in the CO2 -Evolution Test performed according to OECD guideline no. 301B. The initial test concentration was 10 mg/L TOC, equivalent to approx. 13 mg/L test substance. The duration of the exposure was 60 days and the test system (inoculum) was activated sludge from the municipal sewage plant Mannheim, Germany.

The degree of biodegradation of the test substance was 60-70 % CO2/ThCO2 after an exposure period of 60 days. That means that the test substance was biodegradable under the enhanced test conditions of this test.

2 -Propylheptyl acrylate

To assess the potential of the test substance to biodegrade, results of a GLP study carried out with non-adapted domestic sludge were available. The test procedures followed OECD guideline 301 B. In this test a degradation rate of 60 - 70% after 28 days was reported, but the 10 -day window was failed [BASF 2008].

The test substance is a mixture composed of the two isomers 2-propylheptylacrylate and 4 -methyl-2 -propylhexylacrylate. In such a case, the 10-day window should not be applied to interpret the results, since it is anticipated, that depending on structural properties the isomers have different biodegradation kinetics. Therefore 2 -propylheptylacrylate is considered to be readily biodegradable irrespective of the 10 -day window criterion was not being fulfilled for the mixture.

2 -Ethylhexyl acrylate

In a manometric respirometry test conducted according to EU Directive 79/831/EEC Annex V, part C (comparable to OECD guideline 301 F) biodegradation (BOD/ThOD) of 2-ethylhexyl acrylate of 70 - 80 % after 15 days was found (BASF AG 1988). The 10-day window criterion was fulfilled. As inoculum domestic activated sludge was used. Thus, under the conditions of the test, 2 -Ethylhexyl acrylate was readily biodegradable.

Conclusion

Considering the results of the biodegradation studies to Dodecyl acrylate/ Laurylacrylate (C12), 2-Propenoic acid, C16-18-alkyl esters and Icosyl acrylate/ Behenylacrylate (C20) a weight of evidence approach was made.

Data with the read across substance 2-Propenoic acid, C16-18-alkyl esters revealed biodegradation. Nevertheless, the strict criteria for ready biodegradation were not fulfilled. As the test substance consists of different constituents the 10-day window is not applicable.

To be able to finally conclude on this endpoint additional data form another long chain acrylates were considered. A mixture of C12/C14 acrylates was shown to be clearly readily biodegradable. Acrylates with longer C-chaines (e.g. C20 acrylates ) shown that the test substance is nearly completely degraded after 60 days and can thus be judged to be ready biodegradable, but failing the 10- day window. Such a prolonged test is not available for C16/C18 acrylates, but similar results are expected, as the longer C-chained acrylates represent a worst case in this sense.

Taking all data together, 2-Propenoic acid, octadecyl alkyl ester is considered to be readily biodegradable but failing the 10 - day window.