3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorodeca-1,9-diene

Hydrolysis

Administrative data

Endpoint:

hydrolysis

Data waiving:

study scientifically not necessary / other information available

Justification for data waiving:

other:

Justification for type of information:

JUSTIFICATION FOR DATA WAIVING

1,6–divinylfluorohexane does not contain any functional group associated with hydrolysis properties.
The molecular structure of 1,6–divinylfluorohexane is characterized by a perfluorinated carbon chain with two vinyl groups at the far ends of the molecule.
The perfluorinated carbon chain is hydrolytically stable due to the presence of the carbon-fluorine bond, which is in fact one of the strongest bonds in organic chemistry (O’Hagan, 2007). Substitution of hydrogen atoms with fluorine results in increased bond strengths for both carbon-fluorine and adjacent carbon-carbon bonds over the corresponding hydrocarbon and it is expected to increase the resistance to hydrolysis.
The terminal vinyl groups are also not expected to undergo to significant (> 10%) hydrolisis in the condition of the preliminary test described in the OECD TG No. 111 (time = 5 days, pH = 4 to 9, Temperature = 50°C). The proximity with electronegative fluorine atoms makes the vinyl ends resistant to hydrolysis both at acid and basic pHs.
Pratical experience in the use of the substance confirms its abiotic stability at pH 4 to 9 and temperature up to 50°C.
Furthermore, there is evidence of its stability in basic condition (pH>9): its synthesis, in fact, involves as the final step the treatment of its precursor in ethanol/potassium ethylate (pH>9) at 70°C: no reaction occurs on just formed 1,6–divinylfluorohexane.
In conclusion, if tested with the standard OECD TG No. 111 method, B1,6–divinylfluorohexane would not show significant hydrolysis (> 10%) in the preliminary test, meaning that conducting the full study is not justified. The substance is therefore considered hydrolytically stable and its half-life at 25°C is estimated to be > 1 year.

Data source

Reference

Reference 1

Reference Type:

publication

Title:

Understanding organofluorine chemistry. An introduction to the C–F bond

Author:

O'Hagan

Year:

2007

Bibliographic source:

Chemical Society Reviews, vol. 37, no. 2, pp. 308-319. https://doi.org/10.1039/b711844a

Reference 2

Reference Type:

publication

Title:

Explorations in fluorocarbon chemistry.

Author:

Lemal DM

Year:

2002

Bibliographic source:

Abstracts of papers - American Chemical Society 2002-- 223():U556-U556