Process for the manufacture of fluorosurfactants

US9416085B2 · kind B2 · utility

Assignee

• SOLVAY SPECIALTY POLYMERS ITALY S.P.A. · IT

Inventors

• Giuseppe Marchionni · Milano, IT
• Vito Tortelli · Milano, IT

Key dates

• Filing date: Jul 7, 2009
• Grant date: Aug 16, 2016
• Expiry date: Dec 10, 2031

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C51/58
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the manufacture of a perfluorooxycarboxylate of formula (I): RfO—CF2CF2—O—CF2—COOXa (I), wherein Rf is a perfluoro(oxy)alkyl group, and Xa is H, a monovalent metal or an ammonium group of formula NRN4, with RN, equal or different at each occurrence, being H or a C1-6 hydrocarbon group, said process comprising: (A) reacting a perfluorovinylether of formula Rf—O—CF═CF2 with an ethylene glycol derivative selected among ethylene glycol (HO—CH2CH2—OH), glycolic acid (HO—CH2—COOH), glycolaldehyde (HO—CH2—CHO) and protected derivatives thereof, so as to yield the corresponding addition product of formula Rf—O—CFH—CF2—O—CH2-E, and E being selected among —CH2OH, —COOH and —CHO; (B) optionally protecting functional group E with suitable chemistry; (C) fluorinating the (protected) addition product to yield the corresponding perfluorinated addition product; (D) optionally deprotecting the perfluorinated addition product to yield corresponding acyl fluoride of formula Rf—O—CF2—CF2—O—CF2—C(O)F; and (E) hydrolyzing and, optionally, neutralizing, the acyl fluoride for yielding the perfluorooxycarboxylate of formula (I).