reaction products of 2-Propenoic acid (2 moles) and Neopentylglycol hydroxypivalate (1 mole)

Hydrolysis

Link to relevant study record(s)

Reference

Endpoint:

hydrolysis

Type of information:

(Q)SAR

Adequacy of study:

key study

Study period:

2018

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

A QSAR calculation of hydrolysis of the test item with HYDROWIN 2.00 (US-EPA, 2010) was applied as a screening tool.

Given the result obtained (half-life > 1 year at pH 8 for the major hydrolysable constituents), it was considered that it would not be useful to investigate this degradation process more precisely by running an experiment based on the OECD TG 111, as abiotic degradation is not considered a significant degradation pathway for the test item.

Principles of method if other than guideline:

The Aqueous Hydrolysis Rate Program (HYDROWIN v2.00) estimates aqueous hydrolysis rate constants for the following chemical classes: esters, carbamates, epoxides, halomethanes, selected alkyl halides and phosphorus esters. HYDROWIN estimates acid- and base-catalyzed rate constants.

GLP compliance:

not specified

Radiolabelling:

no

Analytical monitoring:

no

Positive controls:

no

Negative controls:

no

Transformation products:

not specified

Key result

pH:

8

Temp.:

25 °C

DT50:

>= 1.098 - <= 1.361 yr

Type:

not specified

Key result

pH:

7

Temp.:

25 °C

DT50:

>= 10.978 - <= 13.607 yr

Type:

not specified

The results reports with the calculation of hydrolysis rates for the relevant constituents are detailed below:

 

Constituent 1: Neopentyl glycol diacrylate

SMILES : C=CC(=O)OCC(C)(C)COC(=O)C=C

CHEM :

MOL FOR: C11 H16 O4

MOL WT : 212.25

--------------------------- HYDROWIN v2.00 Results ---------------------------

 

NOTE: Fragment(s) on this compound are NOT available from the fragment

library. Substitute(s) have been used!!! Substitute R1, R2, R3,

or R4 fragments are marked with double astericks "**".

 

ESTER: R1-C(=O)-O-R2 R1: -CH=CH2

** R2: -CH2-(t-Bu)

Kb hydrolysis at atom # 3: 8.070E-003 L/mol-sec

 

ESTER: R1-C(=O)-O-R2 R1: -CH=CH2

** R2: -CH2-(t-Bu)

Kb hydrolysis at atom # 12: 8.070E-003 L/mol-sec

 

Total Kb for pH > 8 at 25 deg C : 1.614E-002 L/mol-sec

Kb Half-Life at pH 8: 1.361 years

Kb Half-Life at pH 7: 13.607 years

 

Constituent 2: 3-{[3-(acryloyloxy)-2,2-dimethylpropanoyl]oxy}-2,2-dimethylpropyl acrylate

SMILES : C=CC(=O)OCC(C)(C)C(=O)OCC(C)(C)COC(=O)C=C

CHEM :

MOL FOR: C16 H24 O6

MOL WT : 312.37

--------------------------- HYDROWIN v2.00 Results ---------------------------

NOTE: Fragment(s) on this compound are NOT available from the fragment

library. Substitute(s) have been used!!! Substitute R1, R2, R3,

or R4 fragments are marked with double astericks "**".

 

ESTER: R1-C(=O)-O-R2 R1: -CH=CH2

** R2: -CH2-(t-Bu)

Kb hydrolysis at atom # 3: 8.070E-003 L/mol-sec

 

ESTER: R1-C(=O)-O-R2 ** R1: tert-Butyl-

** R2: -CH2-(t-Bu)

Kb hydrolysis at atom # 10: 1.932E-003 L/mol-sec

 

ESTER: R1-C(=O)-O-R2 R1: -CH=CH2

** R2: -CH2-(t-Bu)

Kb hydrolysis at atom # 19: 8.070E-003 L/mol-sec

 

Total Kb for pH > 8 at 25 deg C : 1.807E-002 L/mol-sec

Kb Half-Life at pH 8: 1.215 years

Kb Half-Life at pH 7: 12.152 years

 

Constituent 3: 3-{[3-(acryloyloxy)-di(2,2-dimethylpropanoyl)oxy]-2,2-dimethylpropyl acrylate

SMILES : C=CC(=O)OCC(C)(C)C(=O)OCC(C)(C)COC(=O)C(C)(C)COC(=O)C=C

CHEM :

MOL FOR: C21 H32 O8

MOL WT : 412.48

--------------------------- HYDROWIN v2.00 Results ---------------------------

 

NOTE: Fragment(s) on this compound are NOT available from the fragment

library. Substitute(s) have been used!!! Substitute R1, R2, R3,

or R4 fragments are marked with double astericks "**".

 

ESTER: R1-C(=O)-O-R2 R1: -CH=CH2

** R2: -CH2-(t-Bu)

Kb hydrolysis at atom # 3: 8.070E-003 L/mol-sec

 

ESTER: R1-C(=O)-O-R2 ** R1: tert-Butyl-

** R2: -CH2-(t-Bu)

Kb hydrolysis at atom # 10: 1.932E-003 L/mol-sec

 

ESTER: R1-C(=O)-O-R2 ** R1: tert-Butyl-

** R2: -CH2-(t-Bu)

Kb hydrolysis at atom # 19: 1.932E-003 L/mol-sec

 

ESTER: R1-C(=O)-O-R2 R1: -CH=CH2

** R2: -CH2-(t-Bu)

Kb hydrolysis at atom # 26: 8.070E-003 L/mol-sec

Total Kb for pH > 8 at 25 deg C : 2.001E-002 L/mol-sec

 

Kb Half-Life at pH 8: 1.098 years

Kb Half-Life at pH 7: 10.978 years

Validity criteria fulfilled:

not applicable

Conclusions:

The QSAR hydrolysis calculation for the test item with the program HYDROWIN resulted in half-lives > 1 year for major relevant constituents at pH 8 and at 25°C and up to 13.607 years at pH 7. Therefore, it is not expected that hydrolysis is a significant degradation pathway for this test substance and no further investigation is deemed necessary.

Executive summary:

As a screening tool, a QSAR hydrolysis calculation for the test item with HYDROWIN 2.00 (US-EPA, 2010) was applied. This resulted in half-lives > 1 year for major relevant constituents at pH 8 and at 25°C and up to 13.607 years at pH 7. Therefore, it is not expected that hydrolysis is a significant degradation pathway for this test substance and no further investigation is deemed necessary.

Description of key information

As a screening tool, a QSAR hydrolysis calculation for the test item with HYDROWIN 2.00 (US-EPA, 2010) was applied.

This resulted in half-lives > 1 year for major relevant constituents at pH 8 and at 25°C and up to 13.607 years at pH 7. Therefore, it is not expected that hydrolysis is a significant degradation pathway for this test substance and no further investigation is deemed necessary.

Key value for chemical safety assessment

Half-life for hydrolysis:

1.361 yr

at the temperature of:

25 °C

Additional information

As a conservative approach, the worst-case half-life of 1.361 years at pH 8 and 25 °C was selected for chemical safety assessment.