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Although the reaction can be performed on an industrial scale with good yields, heavy metal residues from the oxidant must be recovered for environmental reasons, making the process expensive
Method used
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[0069] 24.90 g (75 mmol) of MV-31 were mixed with 76.57 g (0.75 mole) of tert-butyl formate and 3 ml (10.5 mmol) of TAPPI-75-AL. The mixture was stirred at 60°C for 18 hours. The tert-butyl formate was then distilled from the reaction mixture using a 200 mm Vigreaux distillation column, and the primary product was distilled in vacuo to yield 23.90 g (55.05 mmol) of a clear, colorless liquid; bp 94 at 75 mmHg -96°C. Yield 73%.
[0072] 108.37 g (0.33 moles) of MV-31 were mixed with 200 g (1.96 moles) of tert-butyl formate and 13 g (32.6 mmoles) of Perkadox 16S. The mixture was stirred at 52-55°C for 24 hours. Then tert-butyl formate was distilled off from the reaction mixture, and the primary product was distilled in vacuo to yield 131.25 g (0,3 mol) of a clear colorless liquid. Yield 93%.
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Abstract
A method for preparing highly fluorinated carboxylic acids and theirs salts and the precursors thereof comprising subjecting a highly fluorinated olefin of the general formula (I) : Rf(O)n-(CF2)m-CF=CF2 to a derivative of formic acid according to the general formula (II) HCOR in the presence of a radical initiator to form carboxylic acid precursor in the form of an O-ester, S-ester or an amideadduct of the general formula (III) and hydrolysing the adduct of formula (III) Rf-On-(CF2)m-CFH-CF2-COR to form the carboxylic acid or its salt of the general formula (IV) RfOn-(CF2)m-CFH-CF2-COO-M+ wherein in formulae (II) and (III) R represents a residue O-M+, S-M+, OR', SR' or NR'R'' wherein R' and R'' are independent of each other linear or branched or cyclic aliphatic or aromatic residues that contain at least one carbon atom and that do not have an alpha-H-atom and Rf represents H or a perfluorinated or partially fluorinated, linear, branched, aliphatic or aromatic, carbon atoms containing residue or hydrogen, n is 1 or 0, m represents an integer between 0 and 6 and M+ represents a cation including H+.
Description
technical field [0001] The present invention relates to a process for the preparation of highly fluorinated carboxylic acids and their salts. Background technique [0002] Highly fluorinated carboxylic acids are useful emulsifiers in the aqueous emulsionpolymerization of fluorinated monomers. In the past, the general formula CF 3 -(CF 2 ) n -COO - m + Perfluorinated low molecular weight carboxylic acids have been used for this purpose, where M + represents a cation and n represents an integer between 4 and 8. However, other more degradable fluorinated emulsifiers have attracted attention for various reasons. [0003] Fluorinated polyether carboxylic acids and partially fluorinated carboxylic acids have been suggested as alternative emulsifiers. Specifically, the general formula (described in US2007 / 0015937 to Hintzer et al.) is [R f -O-L-COO-] i Xi + The highly fluorinated fluoroalkoxycarboxylic acids of , where L represents an alkylene or aliphatic group, R f R...
Claims
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