The present invention relates to a process for the preparation of fluorinated compounds, to novel compounds containing fluorinated end groups, to the use thereof and to compositions comprising novel compounds containing fluorinated end groups.

Disclosed herein is an efficient, environment friendly and commercially viable process for preparation of chloromethylated compound of formula I in substantially pure form and high yield, from the compound of formula II. The process includes contacting the compound of formula II with a chloromethylating agent generated in-situ by reaction of a formaldehyde precursor and hydrogen chloride, in a suitable solvent/contacting medium and in the presence of a catalytic amount of a short chain/low molecular weight carboxylic acid of formula III. I II III wherein, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the description.

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Disclosed herein is an efficient, environment friendly and commercially viable process for preparation of chloromethylated compound of formula I in substantially pure form and high yield, from the compound of formula II. The process includes contacting the compound of formula II with a chloromethylating agent generated in-situ by reaction of a formaldehyde precursor and hydrogen chloride, in a suitable solvent/contacting medium and in the presence of a catalytic amount of a short chain/low molecular weight carboxylic acid of formula III. I II III wherein, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the description.

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A method includes combining first components including at least one of CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl or CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO.sub.2Cl).sub.3 and hexafluoropropylene to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl. Another method includes combining second components including M(OSO.sub.2CF.sub.3).sub.3 and hexafluoropropylene at a temperature above 0° C. to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, wherein M is Al or B. The compound CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl is also provided.

A method includes combining first components including at least one of CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl or CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO.sub.2Cl).sub.3 and hexafluoropropylene to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl. Another method includes combining second components including M(OSO.sub.2CF.sub.3).sub.3 and hexafluoropropylene at a temperature above 0° C. to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, wherein M is Al or B. The compound CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl is also provided.

A method includes combining first components including at least one of CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl or CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO.sub.2Cl).sub.3 and hexafluoropropylene to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl. Another method includes combining second components including M(OSO.sub.2CF.sub.3).sub.3 and hexafluoropropylene at a temperature above 0° C. to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, wherein M is Al or B. The compound CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl is also provided.

A method includes combining first components including at least one of CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl or CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO.sub.2Cl).sub.3 and hexafluoropropylene to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl. Another method includes combining second components including M(OSO.sub.2CF.sub.3).sub.3 and hexafluoropropylene at a temperature above 0° C. to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, wherein M is Al or B. The compound CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl is also provided.

A method includes combining first components including at least one of CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl or CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO.sub.2Cl).sub.3 and hexafluoropropylene to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl. Another method includes combining second components including M(OSO.sub.2CF.sub.3).sub.3 and hexafluoropropylene at a temperature above 0° C. to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, wherein M is Al or B. The compound CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl is also provided.

A method includes combining first components including at least one of CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl or CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO.sub.2Cl).sub.3 and hexafluoropropylene to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl. Another method includes combining second components including M(OSO.sub.2CF.sub.3).sub.3 and hexafluoropropylene at a temperature above 0° C. to provide CF.sub.2═CF—CF.sub.2—OSO.sub.2CF.sub.3, wherein M is Al or B. The compound CF.sub.2═CF—CF.sub.2—OSO.sub.2Cl is also provided.

Methods for manufacturing phenoxyethanol from a reaction of a phenolate with a monohalohydrin. The phenolate is reacted with the monohalohydrin at a reaction temperature that is less than or equal to a boiling point of a reaction mixture to produce products that include the phenoxyethanol.