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Hydrolysis

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Endpoint:
hydrolysis
Type of information:
experimental study
Adequacy of study:
weight of evidence
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Acceptable, well documented study report which meets basic scientific principles
Qualifier:
no guideline followed
Principles of method if other than guideline:
The hydrolysis of alkenyl succinic anhydride (ASA) under physiological conditions (pH 7.4, temperature 37°C) has been investigated by using liquid chromatography -mass spectrometry for analysis of ASA and ASAcid before and after hydrolysis.
GLP compliance:
no
Remarks:
Acceptable, well documented study report which meets basic scientific principles
Radiolabelling:
no
Analytical monitoring:
yes
Details on sampling:
- Sampling intervals for the parent/transformation products: 0 and 14 h
- Sampling method: Aliquots were shaken vigorously for about one minute on a shaker.Thereafter the formed two phases were separated by centrifugation at 1200 rpm for 5 minutes.
Buffers:
- pH: 7.4
- Type and final molarity of buffer: phosphate buffer
- Composition of buffer: Potassiumdihydrogenphosphate(1.18 g), disodiumhydrogenphosphate,dihydrate(4.43 g), Ultrapure water(1 L)
Details on test conditions:
TEST MEDIUM
- Preparation of test medium: To each of three Erlenmeyer flasks was weighed 0.8 g ASA and about 80 g phosphate buffer. Homogeneous emulsions were formed using a high speed mixer, run at highest speed for hal fa minute. Aliquots were taken for measurement of initial levels of ASA and ASAcid (t=0).
Duration:
14 h
pH:
7.4
Temp.:
37 °C
Initial conc. measured:
197.2 mg/L
Number of replicates:
3
Positive controls:
no
Negative controls:
no
Transformation products:
yes
No.:
#1
Details on hydrolysis and appearance of transformation product(s):
- Pathways for transformation: hydrolysis
% Recovery:
ca. 3
pH:
7.4
Temp.:
37 °C
Duration:
14 h
pH:
7.4
Temp.:
37 °C
DT50:
< 14 h
Type:
other: not determined
Remarks on result:
other: 97% hydrolysis after 14 h
Validity criteria fulfilled:
not applicable
Conclusions:
The test item shows hydrolytic degradation under physiological conditions (pH 7.4, temperature 37°C). Within 14 hours, 97 % of the initial ASA amount has hydrolyzed into alkenyl succinic acid.
Executive summary:

The hydrolysis of alkenyl succinic anhydride (ASA) under physiological conditions (pH 7.4, temperature 37°C) was investigated by using liquid chromatography-mass spectrometry for analysis of ASA and ASAcid before and after hydrolysis. Within 14 hours, 97 % of the initial ASA amount has hydrolysed into alkenyl succinic acid (ASAcid).

Endpoint:
hydrolysis
Type of information:
experimental study
Adequacy of study:
weight of evidence
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
other: GLP-guideline study with analytical monitoring
Qualifier:
according to guideline
Guideline:
OECD Guideline 111 (Hydrolysis as a Function of pH)
Deviations:
yes
Remarks:
Low water solubility, but easily emulsifiable in water. Therefore, preparations of test item emulsified in water and in the prescribed buffer solutions were made.
GLP compliance:
yes (incl. QA statement)
Remarks:
Competence Center Analytics, BASF SE, D-67056 Ludwigshafen
Radiolabelling:
no
Analytical monitoring:
yes
Buffers:
- Buffer pH 4.00 (Bernd Kraft: citric acid, sodium chloride, sodium hydroxide);
- Buffer pH 7.00 (Bernd Kraft: phosphate mixture);
- Buffer pH 9.00 (Bernd Kraft: boric acid, potassium chloride, sodium hydroxide);
Details on test conditions:
TEST MEDIUM
- Preparation of test medium: 660.68 – 665.20 mg of the test item exactly weighed were dispersed by permanent stirring in 200 mL of demineralized water or buffer pH 4, 7 or 9. As the averaged molecular weight of the test item was given as 333.2 g/mol, the concentrations of test item in the resulting emulsions were 0.01 mol/L.
Preliminary study:
The test item shows hydrolytic degradation as soon as it is encountered with water at 20°C.
demineralized water, 20°C: no first order kinetic
pH 4, 20°C: no first order kinetic
pH 7, 20°C: not measurable due to extremely formati on of foam
pH 9, 20°C: not measurable due to extremely format ion of foam
Transformation products:
yes
No.:
#1
Key result
pH:
4
Temp.:
20 °C
Type:
other: not possible to determine
Remarks on result:
not determinable
pH:
7
Temp.:
20 °C
Type:
other: not possible to determine
Remarks on result:
not determinable
pH:
9
Temp.:
20 °C
Type:
other: not possible to determine
Remarks on result:
not determinable
Details on results:
TEST CONDITIONS
- pH, sterility, temperature, and other experimental conditions maintained throughout the study: Yes
- Anomalies or problems encountered: The degradation reactions measured in demin. water and in buffer pH 4 at 20°C are not first order or pseudo-first order. Due to this kobs half lives cannot be calculated.
At an elevated stirring rate and pH 7 and pH 9 the IR measurement is disturbed by foam, hence a record of ASA hydrolysis failed at pH 7 and pH 9. The measurement in demin. water with elevated stirring rate was possible but the result cannot be compared directly with the measurement at 8000 rpm (without foam). In general the hydrolysis of organic anhydrides is accelerated at neutral and alkaline pH and ends up (by using of buffer salts) in the corresponding acid salt. In case of the test item the final hydrolysis product is an alkenyl succinic acid salt (alkenyl succinate), a chemical structure with surfactant properties, which gives rise to foam formation. The extremely formation of foam at pH 7 and pH 9 suggests a rapid hydrolysis under these conditions.
Validity criteria fulfilled:
not applicable
Remarks:
only pre-test conducted
Conclusions:
The test item shows hydrolytic degradation as soon as it is encountered with water at 20°C. The extremely formation of foam at pH 7 and pH 9 suggests a rapid hydrolysis under these conditions.
Executive summary:

In a pre-test for a OECD 111 study, the substance showed hydrolysis in water at pH7, but no kinetic could be derived. At pH 7 and 9 foam formation was apparent preventing the determination of the hydrolysisi rate. However, foam builing is regarded as a consequence of the hydrolysis product alkenyl succinic acid salt, which is a generarl reaction of organic anhydrides at neutral and alkaline pH.

Description of key information

Hydrolysis: 97% in 14 h at pH 7.4 and 37°C
2,5-Furandione, dihydro-, mono-C15-20-alkenyl derivs. appears to hydrolyze very rapidly at 20°C at pH 4, 7 and 9 as soon as it comes to contact with water.
The half-life at 70°C was 27 min in pure water and 80 min in water-THF, respectively.

Key value for chemical safety assessment

Half-life for hydrolysis:
27 min
at the temperature of:
70 °C

Additional information

In a pre-test for a OECD 111 study, 2,5-Furandione, dihydro-, mono-C15-20-alkenyl derivs. showed hydrolysis with water at pH 7, but no kinetic could be derived. At pH 7 and 9 foam formation was apparent preventing the determination of the hydrolysis rate. However, foam building is regarded as a consequence of the hydrolysis product alkenyl succinic acid salt, which is a general reaction of organic anhydrides at neutral and alkaline pH.

The hydrolysis of the substance under physiological conditions (pH 7.4, temperature 37°C) was investigated by using liquid chromatography-mass spectrometry for analysis of the substance and its hydrolysis product ASAcid before and after hydrolysis. Within 14 hours, 97 % of the initial substance amount has hydrolyzed into alkenyl succinic acid (ASAcid).

The hydrolysis of was evaluated by dissolving the substance in pure water or in water together with tetrahydrofuran. The test solutions were mixed constantly and kept at 70 °C. Samples were taken, processed and analysed by HLC. The result showed a approximated zero-order hydrolysis rate and the half-life of 27 min in pure water and a pseudo-first order kinetic with a half-life time of 86 min in water-THF, respectively.