difluoro(fluorosulphonyl)acetyl fluoride and 3,3,4,4-tetrafluoro-1,2-oxathietane 2,2-dioxide

Skin irritation / corrosion

Administrative data

Endpoint:

skin irritation / corrosion, other

Remarks:

Effects predicted from reaction with water or moisture

Type of information:

experimental study

Remarks:

hydrolysis in the presence of water

Adequacy of study:

other information

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Not an experimental test result for skin irritation but chemical reactivity indicates potential hydrolysis to corrosive substances

Cross-reference

Cross-reference 1

Reason / purpose for cross-reference:

read-across: supporting information

Reference

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

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

Principles of method if other than guideline:

- Principle of test: reaction of the isomer Difluoro(fluorosulfonyl)acetyl Fluoride with water was studied
- Short description of test conditions: water was added slowly to the isomer, with stirring and cooling on ice, followed by fractionations to isolate the resulting product
- Parameters analysed / observed: the reaction products were analysed by chromatography

GLP compliance:

no

Remarks:

prior to GLP Standards

Transformation products:

yes

No.:

#1

No.:

#2

% Recovery:

86

Remarks on result:

other: difluoro(fluorosulfonyl)acetic acid obtained from reaction of difluoro(fluorosulfonyl)acetic acid with water

Remarks:

Addition of water done with cooling on ice, then dry nitrogen for one hour (to minimize exothermic reaction)

Remarks on result:

not measured/tested

Details on results:

TEST CONDITIONS
-Temperature conditions maintained throughout the study: Yes

- Description of hydrolysis reaction and structures: see attachment
- the hydrolysis of the sultone isomer was not reported in the publication but the sultone isomer was indicated to behave similarly to the linear isomer in the presence of nucleophilic reagents.

Conclusions:

Both isomers, tetrafluoro-2-hydroxyethanesulfonic β-sultone and difluoro(fluorosulfonyl)acetyl fluoride were reported to react similarly with water to produce difluoro(fluorosulfonyl)acetic acid and hydrogen fluoride.

Cross-reference 2

Reason / purpose for cross-reference:

read-across: supporting information

Reference

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

weight of evidence

Study period:

No details

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

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

Principles of method if other than guideline:

- Principle of test: The reaction of the isomers with water was evaluated
- Short description of test conditions: each isomer was placed in petroleum ether (solvent used to control the exothermic reaction), stirred an cooled to to -10°C. Water was added drop by drop. After separation from the petroleum ether layer, the reaction product (lower layer) was obtained by distillation and charaterized by NMR.

GLP compliance:

no

Specific details on test material used for the study:

Both forms were tested: Fluorosulfonyldifluoroacetyl fluoride and β-hydroxytetrafluoroethanesulfonic acid sultone

Transformation products:

yes

No.:

#1

% Recovery:

75

Temp.:

-10 °C

Remarks on result:

other: Obtained from reaction of Fluorosulfonyl difluoroacetyl fluoride with water

% Recovery:

62

Temp.:

-10 °C

Remarks on result:

other: obtained from reaction of β-hydroxytetrafluoroethanesulfonic acid sultone with water

Remarks on result:

not measured/tested

Other kinetic parameters:

No information on kinetics of transformation

Details on results:

TEST CONDITIONS
- the temperature was maintained at -10°C throughout the study to moderate the exothermic reaction.

With both isomers, the reaction product formed in the presence of water was fluorosulfonyldifluoroacetic acid (boiling point 88-90°C) at 45 mmHg.

Fluorine and hydrogen NMR spectra were consistent with this structure.

The further reaction of fluorosulfonyldifluoroacetic acid with water in the presence of 0.3 mol sodium hydroxide during 18 hours at room temperature produced carboxydifluoromethanesulfonic acid (characterized by NMR and IR spectra).

Conclusions:

The β-hydroxytetrafluoroethanesulfonic acid sultone is reported to react with water to form the fluorosulfonyldifluoroacetic Acid most likely at the acid fluoride group, more reactive than the sulfonyl fluoride group.
Fluorosulfonyl difluoroacetyl fluoride can also reacts with water to form the fluorosulfonyldifluoroacetic Acid.

Materials and methods

Principles of method if other than guideline:

- Principle of test: the reaction of either isomer with water was investigated
- Short description of test conditions: the isomers were place in the presence of water under temperature controlled conditions and the reaction products were identified.
- Parameters analysed / observed: the reaction products were identified by NMR.

GLP compliance:

no

Applicant's summary and conclusion

Interpretation of results:

Category 1 (corrosive) based on GHS criteria

Conclusions:

Information provided by chemical reactivity of the isomers with water and identification of the hydrolysis products as a carboxylic acid and hydrogen fluoride support the conclusion of potential corrosion properties of the reaction mass in contact with the skin.