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Environmental fate & pathways

Biodegradation in water: screening tests

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Description of key information

Moderately biodegradable (not readily biodegradable according to OECD criteria).

Key value for chemical safety assessment

Additional information

QSAR-disclaimer

 In Article 13 of Regulation (EC) No 1907/2006, it is laid down that information on intrinsic properties of substances may be generated by means other than tests, provided that the conditions set out in Annex XI (of the same Regulation) are met.

According to Annex XI of Regulation (EC) No 1907/2006 (Q)SAR results can be used if (1) the scientific validity of the (Q)SAR model has been established, (2) the substance falls within the applicability domain of the (Q)SAR model, (3) the results are adequate for the purpose of classification and labeling and/or risk assessment and (4) adequate and reliable documentation of the applied method is provided.

The criteria listed in Annex XI of Regulation (EC) No 1907/2006 are considered to be adequately fulfilled and, therefore, the endpoint(s) sufficiently covered and suitable for risk assessment.

Assessment:

In a CO2 evolution test according to OECD guideline 301B the biodegradation of TPGDA was investigated [Cray Valley, 1997]. After 28 days 48 % degradation of TPGDA was determined. Therefore TPGDA is partly biodegradable but not readily biodegradable according to OECD criteria.

The structural related substance DPGDA is readily biodegradable. In a DOC-Die-Away test according to OECD guideline 301A the biodegradation of DPGDA was investigated [BASF AG, 2001]. After 28 days > 90 % degradation of DPGDA was determined. Since DPGDA differs from TPGDA only in a slightly shorter chain length, it can be expected that TPGDA is ultimately biodegradable under environmental conditions.

TPGDA is an UVCB substance. The following four main constituents which concentrations at or above 0.1 % (w/w) were analytically determined:

1.    Constituent 1 (2-{2-[2-(acryloyloxy)-1-methylethoxy]-1-methylethoxy}-1-methylethyl acrylate), ca. 85% (w/w)

2.    Constituent 2 (2-Propenoic acid, 2-[2-(2-hydroxymethylethoxy)methylethoxy]methylethyl ester), ca. 4% (w/w)

3.    Constituent 3 (2-Propenoic acid (1 or 2), (4 or 5), (7 or 8)-trimethyl-10,14-dioxo-3,6,9,13-tetraoxahexadec-15-en-1-yl ester), ca. 3% (w/)

4.    Constituent 4 ((1 or 2)-methyl-2-{(1 or 2)-methyl-2-[(1 or 2)-methyl-2-(2-propenoyloxy)ethoxy]ethoxy}ethyl (5 or 6), (8 or 9), (11 or 12)-trimethyl-14-oxo-4,7,10,13-tetraoxahexadec-15-en-1-oate), ca. 2% (w/w)

In accordance with Annex IX, Section 9.3.2 and Section 9.2.1.2 the assessment of bioaccumulation or bioconcentration and biodegradation of each constituent and impurity present in concentrations at or above 0.1% (w/w) must be performed. Therefore, in order to assess the biodegradation potential of TPGDA (CAS 42978-66-5) a weight-of-evidence approach with four main constituents was performed. Due to the lack of the experimental data for the constituents, the assessment of biodegradation is based on two QSAR models of CATALOGIC, one QSAR model of BIOWIN and one QSAR model of VEGA.The criteria listed in Annex XI of Regulation (EC) No 1907/2006 are considered to be adequately fulfilled and therefore the endpoint(s) sufficiently covered and suitable for risk assessment.

The table below lists the applied (Q)SAR models, the estimated biodegradation rates and basic information on the applicability domain (AD) for the compound. Detailed information on the model’s results and the AD are given in the endpoint study records of IUCLID Chapter 5.2.1. The selected models comply with the OECD principles for (Q)SAR models.

The following table provides results for the constituents of the substance (impurities or additives are not present in concentrations at or above 0.1 % (w/w)): (AD = Applicability Domain)

Model

Constituent 1

Constituent 2

Constituent 3

Constituent 4

AD

Ready Biodegradability v1.0.9 (VEGA v1.1.3)

 

Readily

Readily

Readily

Readily (not in AD)

Yes

BIOWIN v4.10 (EPI Suite v4.11)

Readily

Readily

Readily

Readily

Yes

Kinetic (301F) v11.15 (OASIS Catalogic v5.13.156)

42% BOD

56% BOD

50% BOD

37% BOD

No

28 Days MITI (301C) v13.16 (OASIS Catalogic v5.13.156)

66% BOD

80% BOD

78% BOD

76% BOD

No

 

Considering all models applied constituents of the registration item are estimated to be readily biodegradable, except the Kinetik (301F) model. The substances are within the applicability domain of the BIOWIN v4.10 and VEGA (v1.1.3) with the only exception of Constituent 4.

The remaining “non-specified constituents” sum up to a typical concentration of approximately 6.0 % (w/w). According to GC analytics, more than 45 peaks contribute to this part of the composition of the registration item. Though it is virtually not possible to identify each single peak and assess the respective substance(s) individually, a generic assessment of the environmentally relevant properties of these ingredients may be applied. Multifunctional acrylates are synthesized from alcohols and acrylic acid. As a consequence, the resulting products – including the “non-specified constituents” – are made of the same, similar chemistry. As shown by the evidence provided above, this chemistry basically is subject to ultimate biotic degradation: in none of the four main constituents, a potential metabolite that may be generated from the degradation of these compounds was identified. Therefore, from a scientific perspective, it is extremely likely that also the degradation of the chemically similar “non-specified constituents” of the registration item will not lead to the formation of a persistent metabolite. The raw materials used as well as the conditions of the reaction chosen during manufacture are targeted to produce 2-{2-[2-(acryloyloxy)-1-methylethoxy]-1-methylethoxy}-1-methylethyl acrylate. Side-products beyond the main constituents discussed above are expected to slightly vary in chain lengths and/or branching, but are not anticipated to significantly differ in terms of structural elements – if at all. Therefore, also these structures are deemed degradable by the same metabolic pathways. Consequently, there is no concern that (part of) the UVCB may persist in the environment.

Metabolites:

CATALOGIC 301C v11.15 (OASIS Catalogic v5.13.1) predicted for the constituents 212 metabolites, identifying 133 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of ≥ 0.1% (for details see ‘Attached background material’ of the respective Endpoint Study Record).

From the 133 relevant metabolites 17 metabolites was identified for the constituent 1, 12 for the constituent 2, 18 for the constituent 3 and 31 for the constituent 4.

Thirty of the relevant metabolites were calculated to be readily biodegradable (≥ 60% after 28 days, based on BOD). The other relevant metabolites were estimated to be not readily biodegradable (0 to 56% after 28 days, based on BOD). In conclusion, the majority of the predicted metabolites present in a concentration of ≥ 0.1% (equivalent to >=0.001 mol/mol parent) are estimated to be not readily biodegradable. The degradation products of TPGDA (CAS-42978-66-5) which are predicted to be not readily biodegradable should be considered as potentially P/vP from a precautionary point of view, until further data become available. However, all metabolites have a log Kow ≤ 3. The log Kow of the relevant metabolites ranges from -2.5 to 2.3, thereby not fulfilling the screening criteria for bioaccumulation (B/vB) as laid down in Section 3.1 of REACH Annex XIII. In conclusion, all (relevant) predicted metabolites are not expected to significantly accumulate.

Table 1. The predicted metabolites from the CATALOGIC 301C v11.15 estimation model with an estimated quantity of ≥ 0.1%.

#

Smiles

Quantity [mol/mol parent]

log Kow

 BOD%

 

Constituent 1

 

 

 

1

CC(COC(C)COC(C)COC(=O)C=C)OC(=O)C=C

0.1138

1.8182

42

2

CC(O)COC(C)COC(C)COC(=O)C=C

0.134

0.4581

48

3

CC(COC(C)COC(=O)C=C)OCOC(C)=O

0.03356

0.5548

58

4

CC(O)COC(C)COC(=O)C=C

0.08252

0.3149

55

5

CC(COC(=O)C=C)OCOC(C)=O

0.02067

0.4116

66

6

CC(O)COC(=O)C=C

0.05084

0.1717

61

7

CC(=O)OCOC(=O)C=C

0.04302

0.2684

49

8

CC(=O)OCO

0.03591

-1.0917

50

9

CC(COC(C)COC(C)C(O)=O)OC(=O)C=C

0.1399

0.6861

50

10

CCOCC(C)OCC(C)OC(=O)C=C

0.1111

1.5053

56

11

CC(O)C(O)=O

0.06854

-0.649

68

12

CCOCOC(C)=O

0.01028

0.0987

89

13

CC(O)COC(C)C(O)=O

0.01422

-0.8172

75

14

CC(C(O)=O)OCOC(C)=O

0.003561

-0.7205

84

15

CC(COC(C)COC(C)COC(=O)C=C)OC(=O)C(O)CO

0.006802

0.5579

44

16

OC(C(O)=O)C(O)=O

0.01121

-2.4723

90

17

CC(COC(C)COC(C)COC(=O)C1CO1)OC(=O)C=C

0.006802

1.5121

51

 

Constituent 2

 

 

 

1

CC(COCC(C)OCC(C)O)OC(=O)C=C

0.1036

0.4581

56

2

CC(COCC(C)OCOC(C)=O)OC(=O)C=C

0.04861

0.5548

52

3

CC(COCC(C)O)OC(=O)C=C

0.1196

0.3149

45

4

CC(COCOC(C)=O)OC(=O)C=C

0.02995

0.4116

74

5

CC(CO)OC(=O)C=C

0.08994

0.1717

57

6

CC(O)C(O)=O

0.28

-0.649

68

7

CC(O)COCC(C)O

0.08987

-0.6388

0

8

CC(O)COC(C)C(O)=O

0.05544

-0.8172

75

9

CC(C(O)=O)OCOC(C)=O

0.01389

-0.7205

84

10

CC(O)COCOC(C)=O

0.02004

-0.9485

80

11

CC(COCC(C)OCC(C)O)OC(=O)C(O)CO

0.007037

-0.8022

55

12

OC(C(O)=O)C(O)=O

0.005799

-2.4723

90

 

Constituent 3

 

 

 

1

CC(COCC(C)OCC(C)OC(=O)CCOC(=O)C=C)OC(=O)C=C

0.01263

1.8499

50

2

CC(COCC(C)OCC(C)OC(=O)C=C)OC(=O)C=C

0.05805

1.8182

43

3

CC(COCC(C)O)OCC(C)OC(=O)C=C

0.1367

0.4581

56

4

CC(COCOC(C)=O)OCC(C)OC(=O)C=C

0.03425

0.5548

62

5

CC(COC(C)C(O)=O)OC(=O)C=C

0.08799

0.5429

57

6

CCOCC(C)OC(=O)C=C

0.06987

1.3621

60

7

CC(O)C(O)=O

0.06865

-0.649

68

8

CC(COCC(C)OCC(C)O)OC(=O)C=C

0.1265

0.4581

56

9

CC(COCC(C)OCOC(C)=O)OC(=O)C=C

0.03168

0.5548

52

10

CC(COCC(C)O)OC(=O)C=C

0.0779

0.3149

45

11

CC(COCOC(C)=O)OC(=O)C=C

0.01951

0.4116

74

12

CC(CO)OC(=O)C=C

0.05861

0.1717

57

13

CC(COCC(C)O)OCC(C)OC(=O)CCOC(=O)C=C

0.02928

0.4898

55

14

CC(COCC(C)OCC(C)OC(=O)CC(O)=O)OC(=O)C=C

0.02928

0.7178

51

15

CC(COCC(C)OCC(C)OC(=O)CCOC(=O)C=C)OC

(=O)C(O)CO

0.004699

0.5896

52

16

CC(COCC(C)OCC(C)OC(=O)C=C)OC(=O)C(O)CO

0.004177

0.5579

50

17

OC(C(O)=O)C(O)=O

0.007314

-2.4723

90

18

CC(COCC(C)OCC(C)OC(=O)CCOC(=O)C1CO1)

OC(=O)C=C

0.004699

1.5438

47

 

Constituent 4

 

 

 

1

CC(COCC(C)OCC(C)OCCC(=O)OC(C)COC(C)COCC

(C)OC(=O)C=C)OC(=O)C=C

0.01263

2.2795

37

2

CC(COCC(C)OCC(C)OCCC(O)=O)OC(=O)C=C

0.2082

0.9028

38

3

CCOC(C)COC(C)COCC(C)OC(=O)C=C

0.1653

1.6485

38

4

CCOC(C)COC(C)C(O)=O

0.05354

0.3732

45

5

CCOCC(C)OCC

0.001786

1.1924

66

6

CCOCC(C)OC(C)O

0.001005

-0.3459

91

7

CC(O)C(O)=O

0.2925

-0.649

68

8

CC=O

0.00517

-0.1659

100

9

CCOC(C)COC(C)O

0.001005

-0.3459

42

10

CCOC(C)C(O)=O

0.06995

0.23

8

11

CCOCC

0.1376

1.0492

7

12

CCOCCO

0.01054

-0.4156

92

13

CC(O)COCOC(C)=O

0.02417

-0.9485

80

14

CC(O)COCC(C)O

0.1084

-0.6388

0

15

CC(O)COC(C)C(O)=O

0.03866

-0.8172

75

16

CC(C(O)=O)OCOC(C)=O

0.009684

-0.7205

84

17

CC(O)COCC(C)(O)OCC(C)O

0.001119

-1.2933

79

18

CC(COCC(C)OCC(C)O)OC(=O)C=C

0.1993

0.4581

56

19

CC(COCC(C)OCOC(C)=O)OC(=O)C=C

0.04993

0.5548

52

20

CC(COCC(C)O)OC(=O)C=C

0.1228

0.3149

45

21

CC(COCOC(C)=O)OC(=O)C=C

0.03076

0.4116

74

22

CC(CO)OC(=O)C=C

0.09238

0.1717

57

23

CC(COCC(C)O)OCC(C)OCCC(=O)

OC(C)COC(C)COCC(C)OC(=O)C=C

0.0316

0.9194

44

24

CC(COCC(C)O)OCC(C)OCCC(O)=O

0.08341

-0.4573

47

25

CC(COCOC(C)=O)OCC(C)OCCC(O)=O

0.02089

-0.3606

56

26

CC(COC(C)C(O)=O)OCCC(O)=O

0.01722

-0.959

42

27

CCOCC(C)OCCC(O)=O

0.02408

0.4467

46

28

CC(COCC(C)O)OCC(C)OC(=O)

CCOC(C)COC(C)COCC(C)OC(=O)C=C

0.0316

0.9194

43

29

OC(C(O)=O)C(O)=O

0.008126

-2.4723

90

30

CC(COCC(C)OCC(C)OCCC(O)=O)OC(=O)C(O)CO

0.00232

-0.3575

44

31

CC(COCC(C)OCC(C)O)OC(=O)C(O)CO

0.00232

-0.8022

55

 

 

CATALOGIC 301F v13.16 (OASIS Catalogic v5.13.1) predicted for the constituents 119 metabolites, identifying 24 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of ≥ 0.1% (for details see ‘Attached background material’ of the respective Endpoint Study Record).

From the 24 relevant metabolites 4 metabolites was identified for the constituent 1, 5 for the constituent 2, 6 for the constituent 3 and 9 for the constituent 4.

All of the relevant metabolites were calculated to be readily biodegradable (≥ 60% after 28 days, based on BOD). Therefore, the degradation products of TPGDA (CAS-42978-66-5) should not be considered as potentially P/vP. Moreover, all metabolites have a log Kow ≤ 3, thereby not fulfilling the screening criteria for bioaccumulation (B/vB) as laid down in Section 3.1 of REACH Annex XIII. In conclusion, all (relevant) predicted metabolites are not expected to significantly accumulate.

Table 2. The predicted metabolites from the CATALOGIC 301F v13.16 estimation model with an estimated quantity of ≥ 0.1%.

#

Smiles

Quantity [mol/mol parent]

log Kow

BOD (%)

Constituent 1

>=0,001

>4,5

1

CC(COC(C)COC(C)C(O)=O)OC(=O)C=C

0.173

0.6861

60

2

CC(O)COC(C)COC(C)C(O)=O

0.09475

-0.674

72

3

CC(O)COC(C)C(O)=O

0.08389

-0.8172

77

4

CC(O)=O

1.06

0.0868

73

 

Constituent 2

 

 

 

1

CC(COCC(C)OCC(O)=O)OC(=O)C=C

0.09455

0.2685

73

2

CC(O)COCC(C)=O

0.001575

-1.0566

89

3

OC(=O)C(O)=O

0.3008

-1.7365

81

4

CC(O)=O

0.5445

0.0868

73

5

CC(C(O)=O)OCC(C)=O

0.02588

-0.8286

85

 

Constituent 3

 

 

 

1

CC(COCC(C)OCC(C)O)OC(=O)C=C

0.001904

0.4581

80

2

CC(COCC(C)OCC(O)=O)OC(=O)C=C

0.1698

0.2685

73

3

CC(O)COCC(C)=O

0.001886

-1.0566

89

4

OC(=O)C(O)=O

0.3087

-1.7365

81

5

CC(O)=O

0.9953

0.0868

73

6

CC(COCC(C)OCC(O)C(O)=O)OC(=O)C=C

0.01641

-0.4673

78

 

Constituent 4

 

 

 

1

CC(COCC(C)OCC(C)OCCC(O)=O)OC(=O)C=C

0.1267

0.9028

70

2

CC(O)COCC(C)=O

0.002698

-1.0566

89

3

OC(=O)C(O)=O

0.5498

-1.7365

81

4

CC(O)=O

1.311

0.0868

73

5

CC(C(O)=O)OCC(C)=O

0.06505

-0.8286

85

6

CC(COCC(C)=O)OCC(C)O

0.001942

-0.9134

84

7

CC(COCC(C)OCC(C)O)OC(=O)C=C

0.00137

0.4581

80

8

CC(COCC(C)OCC(O)=O)OC(=O)C=C

0.1242

0.2685

73

9

CC(COCC(C)OCC(O)C(O)=O)OC(=O)C=C

0.01294

-0.4673

78

 

Based on modeled data relevant degradation products present in concentration of ≥ 0.1% (equivalent to quantity setting in OASIS CATALOGIC: ≥0.001 [mol/mol parent]) do neither fulfill the PBT criteria (not PBT) nor the vPvB criteria (not vPvB).

 

Hence, based on the available experimental data on the TPGDA and calculated data from the weight-of-evidence approach with four main constituents along with the modeled data for the relevant degradation products, it is considered that TPGDA (CAS 42978-66-5) is moderately biodegradable.