N,N-bis(2,3-epoxypropyl)aniline

Hydrolysis

Administrative data

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

other: Experimental test run under GLP and according to OECD and European Community guidelines.

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2011

Materials and methods

Test guideline

Test guideline 1

Qualifier:

according to guideline

Guideline:

OECD Guideline 111 (Hydrolysis as a Function of pH)

Test guideline 2

Qualifier:

according to guideline

Guideline:

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

GLP compliance:

yes (incl. QA statement)

Test material

Test material information

Constituent 1

Reference substance name:

p-(2,3-epoxypropoxy)-N,N-bis(2,3-epoxypropyl)aniline

EC Number:

225-716-2

EC Name:

p-(2,3-epoxypropoxy)-N,N-bis(2,3-epoxypropyl)aniline

Cas Number:

5026-74-4

Molecular formula:

C15H19NO4

IUPAC Name:

4-(oxiran-2-ylmethoxy)-N,N-bis(oxiran-2-ylmethyl)aniline

Test material form:

liquid: viscous

Details on test material:

- Substance type: organic
- Physical state: liquid
- Storage condition of test material: In refrigerator (2-8°C) in the dark

Radiolabelling:

no

Study design

Analytical monitoring:

not specified

Buffers:

Acetate buffer pH 4, 0.1 M : solution of 16.6% 0.1 M sodium acetate and 83.4% 0.1 M acetic acid. The buffer contains 0.0009% (w/v) sodium azide.

Phosphate buffer pH 7, 0.1 M : solution of 0.1 M potassium dihydrogenphosphate adjusted to pH 7 using 10 N sodium hydroxide. The buffer contains
0.0009% (w/v) sodium azide.

Borate buffer pH 9, 0.1 M : solution of 0.1 M boric acid and 0.1 M potassium chloride adjusted to pH 9 using 10 N sodium hydroxide. The buffer contains 0.0009% (w/v) sodium azide.

Number of replicates:

2

Positive controls:

no

Negative controls:

yes

Results and discussion

Preliminary study:

At pH 4, pH 7 and pH 9 a degree of hydrolysis of ≥ 10% after 5 days was observed :
- No test substance was detected in the blank buffer solutions pH 4 and pH 7.
- In the blank buffer solutions of pH9 a small response was observed at the test substance retention time, the contribution base on area to the samples at t=0 was 0.09%, this was negligible.
The mean recoveries of the buffer solutions fell within the criterion range of 70-110%. It demonstrated that the analytical method was adequate to support the hydrolysis study on the test substance.

Test performance:

No test substance was detected in the blank buffer solutions at pH4, 7 and 9.
The mean recoveries of the buffer solutions relative to the stock solution fell within the criterion range of 90-110%. It demonstrated that the analytical method was adequate to support the hydrolysis study on the test substance.

Transformation products:

not measured

Dissipation DT50 of parent compound

Dissipation DT50 of parent compound 1

pH:

7

Temp.:

20 °C

Hydrolysis rate constant:

0.007 h-1

DT50:

4.1 d

Type:

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

Dissipation DT50 of parent compound 2

pH:

7

Temp.:

40 °C

Hydrolysis rate constant:

0.068 h-1

DT50:

10 h

Type:

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

Dissipation DT50 of parent compound 3

pH:

7

Temp.:

50 °C

Hydrolysis rate constant:

0.163 h-1

DT50:

4.3 h

Type:

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

Dissipation DT50 of parent compound 4

pH:

4

Temp.:

25 °C

Hydrolysis rate constant:

0.013 h-1

DT50:

2.2 d

Type:

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

Remarks on result:

other: estimated based on Arrhenius equation

Dissipation DT50 of parent compound 5

pH:

7

Temp.:

25 °C

Hydrolysis rate constant:

0.013 h-1

DT50:

2.3 d

Type:

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

Remarks on result:

other: estimated based on Arrhenius equation

Dissipation DT50 of parent compound 6

pH:

9

Temp.:

25 °C

Hydrolysis rate constant:

0.011 h-1

DT50:

2.6 d

Type:

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

Remarks on result:

other: estimated based on Arrhenius equation

Any other information on results incl. tables

pH 4		pH 7		pH 9
Temperature [°C]	t½	Temperature [°C]	t½	Temperature [°C]	t½
20	3.9 d	20	4.1 d	20	4.6 d
25	2.2 d	25	2.3 d	25	2.6 d
40	10 h	40	10 h	40	12 h
50	3.9 h	50	4.3 h	50	5.7 h

Applicant's summary and conclusion

Validity criteria fulfilled:

yes

Conclusions:

The preliminary test (Tier 1) and main study (Tier 2) were performed for the determination of the rate of hydrolysis of p-(2,3-epoxypropoxy)-N,N-bis(2,3-epoxypropyl)aniline at pH values normally found in the environment (pH 4-9). The test item was dissolved in aqueous solutions buffered at pH 4, 7 and 9. The solutions were incubated at 20 °C, 40 °C or 50 °C. The concentration of the test item was determined after different incubation times. A HPLC method was used for determination of the test item.

Summary of Results
rate half
temperature constant life
pH [°C] [h-1]

pH 4 20 0.007 3.9 d
pH 4 40 0.069 10 d
pH 4 50 0.176 3.9 h

pH 7 20 0.007 4.1 d
pH 7 40 0.068 10 h
pH 7 50 0.163 4.3 h

pH 9 20 0.006 4.6 d
pH 9 40 0.056 12 h
pH 9 50 0.122 5.7 h

Executive summary:

Hydrolysis of p-(2,3-epoxypropoxy)-N,N-bis(2,3-epoxypropyl)aniline was studied at 20, 40 and 50 ºC in sterile aqueous buffered solutions at pH 4, pH 7 and pH 9.  The hydrolysis at 25^oC was estimated based on the Arrhenius equation.

The experiment was conducted in accordance with the EEC directive 440/2008, Guideline C.7 “Degradation - Abiotic Degradation: Hydrolysis as a Function of pH”,“ and the OECD Guideline 111 "Hydrolysis as a Function of pH”, adopted in April 2004 and in compliance with the GLP standards.

 

Samples were analysed by HPLC. 

pH 4		pH 7		pH 9
Temperature [°C]	t½	Temperature [°C]	t½	Temperature [°C]	t½
20	3.9 d	20	4.1 d	20	4.6 d
25	2.2 d	25	2.3 d	25	2.6 d
40	10 h	40	10 h	40	12 h
50	3.9 h	50	4.3 h	50	5.7 h

This study is classified acceptable and satisfies the guideline requirement for hydrolysis study.