Trifluoromethanesulphonic anhydride

Hydrolysis

Link to relevant study record(s)

Reference

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

key study

Study period:

21/05/2014

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

study well documented, meets generally accepted scientific principles, acceptable for assessment

Qualifier:

no guideline followed

Principles of method if other than guideline:

Trifluoromethanesulfonic anhydride is known to be unstable in water due to its chemical structure. This study has the objective to confirm this property by the analytical determination of the disappearance of trifluoromethanesulfonic anhydride in water and the formation of its degradation product, i.e. trifluoromethanesulfonic acid.

GLP compliance:

no

Remarks:

The objective of this study was to confirm analyticaly the chemical reaction of the substance in water which can be easily deduced from its chemical structure. Therefore, GLP conditions were not considered as mandatory.

Radiolabelling:

no

Analytical monitoring:

yes

Details on test conditions:

The study of triflic anhydride hydrolysis is performed by Fluorine NMR. 20 mg of triflic anhydride are added to 1 ml of D2O. This substance is not soluble in water but after a manual stirring during 2 min, the solution is homogeneous. The solution is analyzed by fluorine NMR.

Test performance:

Only the presence of triflic acid (-78.8ppm) was observed and no trace of triflic anhydride (-74.3ppm, neat with DMSO d6 capillary). The visual observation supports the absence of triflic anhydride because this substance is not soluble in water and would generate droplets in D2O.
Therefore, in these testing conditions, the hydrolysis of triflic anhydride is quick and complete

Transformation products:

yes

No.:

#1

Key result

Temp.:

20 °C

DT50:

<= 2 min

Type:

not specified

Validity criteria fulfilled:

not applicable

Conclusions:

The hydrolysis of trifluoromethanesulfonic anhydride is quick and complete. The degradation product is trifluoromethanesulfonic acid.

Description of key information

Trifluoromethanesulfonic anhydride is known to be unstable in water due to its chemical structure. To confirm this hydrolysis, a solution at 20mg/mL was prepared in D2O and analysed by Fluorine NMR after 2 min of stirring. Only the presence of trifluoromethanesulfonic acid was observed and there was no trace of trifluoromethanesulfonic anhydride.

Therefore, in these testing conditions, the hydrolysis of trifluoromethanesulfonic anhydride is quick and complete. The degradation product is trifluoromethanesulfonic acid.

Key value for chemical safety assessment

Half-life for hydrolysis:

2 min

at the temperature of:

20 °C