4-hydroxymethyl-1,3-dioxolan-2-one

Hydrolysis

Administrative data

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

3 (not reliable)

Rationale for reliability incl. deficiencies:

other: No guideline study. Limited information on methods.

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2003

Report date:

2003

Materials and methods

Test guideline

Qualifier:

no guideline followed

Principles of method if other than guideline:

Based on results from MEC (methylethylenecarbonate)

GLP compliance:

no

Test material

Test material information

Constituent 1

Reference substance name:

methylenecarbonate

IUPAC Name:

methylenecarbonate

Test material form:

not specified

Radiolabelling:

no

Study design

Analytical monitoring:

no

Results and discussion

Dissipation DT50 of parent compound

Dissipation DT50 of parent compound 1

pH:

0.6

Temp.:

52 °C

Hydrolysis rate constant:

0.001 min-1

DT50:

27 h

Type:

second order

Remarks on result:

other: MEC expressed as l/mol/min

Dissipation DT50 of parent compound 2

pH:

8.2

Temp.:

0

Hydrolysis rate constant:

0.001 min-1

DT50:

33 h

Type:

second order

Remarks on result:

other: MEC

Any other information on results incl. tables

Hydrolysis of jeffsol glycerine carbonate leads to CO2 and diol as hydrolysis end products. Hydrolysis rate were reported from MEC. MEC contains a hydroxygroup and this hydroxy group is removed from the site of hydrolysis by at least 3 atoms, making MEC a suitable surrogate for jeffsol GC. The second-order hydrolysis rate contact of MEC is 6.14E-04 L/mol/min, cooresonding to a half life of 17h at 52°C. Based on the general rule of doubling the half-life per decade of temparture decrease, the half-life at 20°C was estimated at 220h. Based on the OECD guideline 111, these surrogate predicts that jeffsol GC would be hydrolytically unstable at acidic pH. This also applies at basic pH, because the rate of hydrolysis of the surrogate is faster a basic pH (33h at 0°, corresponding to 8h at 20°C). No hydrolysis half-life data was found under neutral conditions. However, under initially neutral unbuffered conditions, the hydrolysis of Jeffsol GC would cause the pH become more acidic due to the hydrolysis product CO2. Therefore, given the above hydrolysis half-life of the surrogate MEC under acidic conditions (9 days at 20C°), it is likely that the half-life of jeffsol GC under initially neutral unbuffered conditions would be comparable to the MEC half-life under acidic conditions.

Applicant's summary and conclusion

Conclusions:

Based on the surrogate data, it was concluded that Jeffsol GC would be hydrolytically unstable (OECD, 1993, guideline 111) at acidic and basic pH. Due to the acidity caused by the hydrolysis product CO2, jeffsol GC would likely to be hydrolytically unstable under initially neutral unbuffered conditions.