m-bis(2,3-epoxypropoxy)benzene

Hydrolysis

Administrative data

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

key study

Study period:

25 January 2018 - 24 March 2018

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2018

Report date:

2018

Materials and methods

Test guideline

Test guideline 1

Qualifier:

according to guideline

Guideline:

EU Method C.7 (Degradation: Abiotic Degradation: Hydrolysis as a Function of pH)

Deviations:

no

Test guideline 2

Qualifier:

according to guideline

Guideline:

OECD Guideline 111 (Hydrolysis as a Function of pH)

Deviations:

no

GLP compliance:

yes (incl. QA statement)

Test material

Test material information

Constituent 1

Reference substance name:

m-bis(2,3-epoxypropoxy)benzene

EC Number:

202-987-5

EC Name:

m-bis(2,3-epoxypropoxy)benzene

Cas Number:

101-90-6

Molecular formula:

C12H14O4

IUPAC Name:

2-({3-[(oxiran-2-yl)methoxy]phenoxy}methyl)oxirane

Test material form:

liquid: viscous

Details on test material:

Identification: m-bis(2,3-epoxypropoxy)benzene
EC Number: 202-987-5
Physical state/Appearance: colorless slightly viscous liquid
Batch: 53715080
Purity: not provided
Expiry Date: 05 Aug 2019
Storage Conditions: room temperature in the dark

Specific details on test material used for the study:

- Source and lot/batch No.of test material: 53715080
- Storage condition of test material: Room temperature in the dark

Radiolabelling:

no

Study design

Analytical monitoring:

yes

Details on sampling:

Duplicate sample solutions were taken initially and from the water bath at various time points. The pH of each solution recorded. The concentration of test item in the sample solutions was determined by HPLC.

Buffers:

- pH: 4
Citric acid 12mmol dm-3, Sodium chloride 8mmol dm-3, Sodium hydroxide 14mmol dm-3

- pH: 7
Disodium hydrogen orthophosphate (anhydrous) 6 mmol dm-3, Potassium dihydrogen orthophosphate 4 mmol dm-3, Potassium dihydrogen orthophosphate 4mmol dm-3

- pH: 9
Disodium tetraborate 2mmol dm-3,Sodium chloride 4 mmol dm-3,

Details on test conditions:

Stock solutions of test item were prepared at nominally 10 g/L in purified water. After preparation, the solutions were shaken (200 rpm) at 30.0 ± 1.0 °C for 18 hours followed by static equilibration at 20.0 ± 0.5 °C for 24¾ hours. After equilibration, the solutions were clear, colorless solutions containing much undissolved test item. The solutions were then filtered under vacuum through 0.2 μm membrane filters. After filtration, the solutions were clear, colorless solutions free from undissolved test item. The stock solutions were then diluted by a factor of 2 with the relevant pH buffer solution. The working solutions were then split into individual glass vessels, sealed with minimal headspace, for each data point. These sample solutions were shielded from light whilst maintained at the test temperature.

Duration of test

Duration of test 1

Duration:

24 h

pH:

4

Temp.:

50 °C

Initial conc. measured:

ca. 10 g/L

Remarks:

pH 4, 7, and 9 measured in this preliminary test/tier 1

Duration of test 2

Duration:

7 h

pH:

4

Temp.:

50 °C

Initial conc. measured:

ca. 10 g/L

Remarks:

pH 4, 7, and 9 measured in this test/tier 2

Duration of test 3

Duration:

4 h

pH:

4

Temp.:

60 °C

Initial conc. measured:

ca. 10 g/L

Remarks:

Results from the Preliminary test/Tier 1 showed it was necessary to undertake further testing at pH 4, pH 7 and pH 9. Solutions were maintained at 50.0 ± 0.5 °C for a period of 7 hours, and 60.0 ± 0.5 °C and 70.0 ± 0.5 °C for a period of 4 hours.

Positive controls:

no

Negative controls:

no

Results and discussion

Preliminary study:

pH 4 at 50 ºC result: t1/2 = 8.02 hours
pH 7 at 50 ºC result: t1/2 = 9.20 hours
pH 9 at 50 ºC result: t1/2 = 9.69 hours
The extent of hydrolysis after 24 hours indicated that a further test (Tier 2) was required to estimate the rate constant and half-life at 25 °C.

Transformation products:

not measured

Details on hydrolysis and appearance of transformation product(s):

As the test item contains two epoxy ring groups, the hydrolysis products were considered to
be the intermediate mono-glycol hydrolysis product and the di-glycol hydrolysis product

Dissipation DT50 of parent compound

Dissipation DT50 of parent compound 1

Key result

pH:

4

Temp.:

25 °C

Hydrolysis rate constant:

ca. 0.009 h-1

DT50:

ca. 77.4 h

Type:

(pseudo-)first order (= half-life)

Dissipation DT50 of parent compound 2

Key result

pH:

7

Temp.:

25 °C

Hydrolysis rate constant:

ca. 0.006 h-1

DT50:

ca. 117 h

Type:

(pseudo-)first order (= half-life)

Dissipation DT50 of parent compound 3

Key result

pH:

9

Temp.:

25 °C

Hydrolysis rate constant:

ca. 0.006 h-1

DT50:

ca. 119 h

Type:

(pseudo-)first order (= half-life)

Details on results:

TEST CONDITIONS
- pH, sterility, temperature, and other experimental conditions maintained throughout the study: Yes

MAJOR TRANSFORMATION PRODUCTS: As the test item contains two epoxy ring groups, the hydrolysis products were considered to be the intermediate mono-glycol hydrolysis product and the di-glycol hydrolysis product

Applicant's summary and conclusion

Validity criteria fulfilled:

not specified

Conclusions:

No significant peaks were observed at the approximate retention time of the test item on analysis of any matrix blank solutions.
The rate of hydrolysis was greater in acidic media (pH 4) than in neutral or alkaline media. The rate of hydrolysis was observed to be similar in neutral and alkaline media.