1,1-Bis(acryloyloxymethyl)ethyl isocyanate

Hydrolysis

Administrative data

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

key study

Study period:

30 Sep 2015

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

guideline study with acceptable restrictions

Data source

Reference

Reference 1

Reference Type:

study report

Title:

Unnamed

Year:

2016

Report date:

2016

Reference 2

Title:

Unnamed

Year:

2017

Report date:

2017

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:

no

Remarks:

Preliminary test

Test material

Test material information

Constituent 1

Reference substance name:

2-isocyanato-2-methyl-3-(prop-2-enoyloxy)propyl prop-2-enoate

Cas Number:

886577-76-0

Molecular formula:

C11H13NO5

IUPAC Name:

2-isocyanato-2-methyl-3-(prop-2-enoyloxy)propyl prop-2-enoate

Radiolabelling:

no

Study design

Analytical monitoring:

yes

Details on sampling:

- Sampling method: Aliquots (100 μL) of a stock solution of the test item in acetonitrile (10 g/l) were added to vials containing buffer solution (10 mL), which had been purged with nitrogen and pre-equilibrated at test temperature (50 °C) in a water bath. This produced test solutions of nominal concentration 100 mg/L. One pair of samples was processed for analysis immediately, whilst another pair was returned to the water bath for 10 minutes prior to processing. On both occasions, the entire volume of each sample was extracted with chloroform (10 mL) and the extract analysed directly by gas chromatography (GC).

Buffers:

pH 4.0 : Potassium dihydrogen orthophosphate (3.00 g) and disodium hydrogen orthophosphate dodecahydrate (6.40 g) were dissolved in purified water (950 ml) and the pH was adjusted to 4.0 ± 0.05 with orthophosphoric acid. The volume was then adjusted to 1000 ml with purified water.pH 7.0 : Potassium dihydrogen orthophosphate (6.80 g) was dissolved in purified water (950 ml), 1M sodium hydroxide (30 ml) was added and the pH was adjusted to 7.0 ± 0.05 with 1M hydrochloric acid. The volume was then adjusted to 1000 ml with purified water.pH 9.0 : Disodium tetraborate decahydrate (16.6 g) and potassium dihydrogen orthophosphate (1.80 g) were dissolved in purified water (950 ml) and the pH was adjusted to 9.0 ± 0.05 with 1M hydrochloric acid.. The volume was then adjusted to 1000 ml with purified water.

Duration of test

Duration of test 1

Duration:

10 min

pH:

4

Temp.:

50 °C

Initial conc. measured:

88.7 mg/L

Duration of test 2

Duration:

10 min

pH:

7

Temp.:

50 °C

Initial conc. measured:

92.1 mg/L

Duration of test 3

Duration:

10 min

pH:

9

Temp.:

50 °C

Initial conc. measured:

82.4 mg/L

Number of replicates:

2 replicates

Positive controls:

no

Negative controls:

no

Results and discussion

Preliminary study:

Preliminary investigationThe preliminary study showed that at pH 4, 7 and 9 and 50 ± 0.5 °C, greater than 50% hydrolysis had occurred after 10 minutes, indicating a half-life of significantly less than 1 day under environmental conditions (25 °C).Degradation productDegrdation product was detected by GC Analysis after the extraction treatment of the test solution. The chemical structure of this product is not determined. pH of test solutionsThe pH values showed that there was no significant change in pH of the buffer solutions after addition of the test substance, indicating that the test systems were close to nominal pH.

Transformation products:

not measured

Remarks:

expert statement (Javier CUESTA-PÉREZ, 2017)

Identity of transformation products

No.:

#1

Reference

Reference substance name:

Unnamed

IUPAC name:

Carbonylbis(azanediyl-2-methylpropane-2,1,3-triyl) tetraprop-2-enoate

CAS number:

n.a

Identifier:

common name

Identity:

N,N’-Di(1,1-bis(acryloyloxymethyl)ethyl)urea

Molecular formula:

C21H28N2O9

Molecular weight:

452.455

SMILES notation:

O=C(C=C)OCC(C)(COC(=O)C=C)NC(=O)NC(C)(COC(=O)C=C)COC(=O)C=C

InChl:

InChI=1S/C21H28N2O9/c1-7-15(24)29-11-20(5,12-30-16(25)8-2)22-19(28)23-21(6,13-31-17(26)9-3)14-32-18(27)10-4/h7-10H,1-4,11-14H2,5-6H3,(H2,22,23,28)

Dissipation DT50 of parent compound

Dissipation DT50 of parent compound 1

pH:

4

Temp.:

25 °C

DT50:

< 1 d

Type:

not specified

Dissipation DT50 of parent compound 2

pH:

7

Temp.:

25 °C

DT50:

< 1 d

Type:

not specified

Dissipation DT50 of parent compound 3

pH:

9

Temp.:

25 °C

DT50:

< 1 d

Type:

not specified

Any other information on results incl. tables

CONCLUSION

The test item was determined to be hydrolytically unstable under acidic, neutral and basic conditions.

Table 1: Preliminary investigation results for hydrolysis of the test item

pH	Ct (mg/l)
	t0min		t10min
	Measured	Mean	Measured	Mean
4	85.3, 92.0	88.7	17.9, 18.1	18.0
7	94.7, 89.5	92.1	5.1, 6.2	5.7
9	77.5, 87.2	82.4	2.1, 2.8	2.4

 

Applicant's summary and conclusion

Conclusions:

The test item was determined to be hydrolytically unstable under acidic, neutral and basic conditions. The most probable outcome of the hydrolysis of the test item is the stable urea derivate, Carbonylbis(azanediyl-2-methylpropane-2,1,3-triyl) tetraprop-2-enoate (CUESTA-PÉREZ, J., 2017).