Method for purifying fluorinated compound
View Patent ↗A method for purifying a fluorinated carboxylic acid having an etheric oxygen atom and its derivative, with small decomposition and inclusion of impurities. A liquid containing at least one member selected from the group consisting of a fluorinated compound represented by application formulae (1) and (2) is held at a heating temperature of at most 150° C. and distilled. Further, the liquid is a liquid obtained from any of a waste liquid after an aqueous emulsion of a fluoropolymer is coagulated and the fluoropolymer is separated, an aqueous liquid obtained by cleaning an exhaust gas in a step of drying and/or a step of heat treatment of the separated fluoropolymer, and a liquid obtained by cleaning an anion exchange resin which has been brought into contact with the waste liquid or an aqueous dispersion obtained from the aqueous emulsion of the fluoropolymer, with an alkaline aqueous solution.
1. A method for recovering a fluorinated compound, which compound is at least one selected from the group consisting of a fluorinated compound represented by formula (1) and a fluorinated compound represented by formula (2):
R F OR 1 COOH (1)
R F OR 1 COOR 2 (2)
wherein R F is a linear or branched monovalent fluoroorganic group which may have an etheric oxygen atom in its main chain, R I is a linear or branched bivalent organic group, and R 2 is a linear or branched monovalent organic group,
wherein said method comprises distilling:
a waste liquid remaining after an aqueous emulsion of a fluoropolymer is coagulated and the fluoropolymer is separated, or
an aqueous liquid obtained by cleaning an exhaust gas originating from drying and/or heat treating a fluoropolymer, or
a liquid obtained by cleaning an anion exchange resin with an alkaline aqueous solution,
at a heating temperature of at most 150° C., wherein said waste liquid, said aqueous liquid and said liquid obtained by cleaning an anion exchange resin comprise at least one fluorinated compound represented by formula (1) or formula (2).
2. The method for recovering a fluorinated compound according to claim 1 , wherein said waste liquid, said aqueous liquid and said liquid obtained by cleaning an anion exchange resin comprise at least one compound of formula (1), and wherein the fluorinated compound represented by formula (1) was produced in said waste liquid, said aqueous liquid and said liquid by adding an acid to a fluorinated compound represented by the following formula (3):
[R F OR 1 COO − ] m X m+ (3)
wherein R F is a linear or branched monovalent fluoroorganic group which may have an etheric oxygen atom in its main chain, R′ is a linear or branched bivalent organic group, X is a m-valent metal ion, an ammonium ion or an alkyl-substituted ammonium ion, and m is an integer of from 1 to 3.
3. The method for recovering a fluorinated compound according to claim 1 , wherein said waste liquid, said aqueous liquid and said liquid obtained by cleaning an anion exchange resin comprise at least one compound of formula (2), and wherein the fluorinated compound represented by formula (2) was produced in said waste liquid, said aqueous liquid and said liquid obtained by cleaning an anion exchange resin by an esterification reaction of the fluorinated compound represented by formula (1) with an alcohol represented by R 2 OH wherein R 2 is a linear or branched monovalent organic group.
4. The method for recovering a fluorinated compound according to claim 1 , wherein said method comprises distilling:
a waste liquid remaining after an aqueous emulsion of a fluoropolymer is coagulated and the fluoropolymer is separated, or
an aqueous liquid obtained by cleaning an exhaust gas originating from drying and/or heat treating a fluoropolymer, and
wherein the fluoropolymer is a homopolymer or copolymer of tetrafluoroethylene.
5. The method for recovering a fluorinated compound according to claim 1 , wherein the heating temperature is at most 130° C.
6. The method for recovering a fluorinated compound according to claim 1 , wherein the fluorinated compound is a fluorinated compound represented by the following formula (4):
R F2 (O(CF 2 ) p ) n OCF 2 COOH (4)
wherein R F2 is a linear or branched C 1-6 perfluoroalkyl group, p is an integer of from 1 to 5, and n is an integer of from 0 to 5,
and wherein said waste liquid, said aqueous liquid and said liquid obtained by cleaning an anion exchange resin comprise a fluorinated compound represented by formula (4).
7. The method for recovering a fluorinated compound according to claim 1 , wherein the heating temperature is at most 100° C.
8. The method for recovering a fluorinated compound according to claim 1 , wherein the heating temperature is at least 30° C.
9. The method for recovering a fluorinated compound according to claim 1 , wherein the fluorinated compound is a fluorinated compound represented by the following formula:
CF 3 CF 2 OCF 2 CF 2 OCF 2 COOH
and wherein said waste liquid, said aqueous liquid and said liquid obtained by cleaning an anion exchange resin comprise a fluorinated compound represented by said formula.
10. The method for recovering a fluorinated compound according to claim 9 , wherein the fluorinated compound represented by the formula
CF3CF2OCF2CF2OCF2COOH
was produced in said waste liquid, said aqueous liquid and said liquid obtained by cleaning an anion exchange resin by adding an acid to a fluorinated compound represented by the following formula
CF3CF2OCF2CF2OCF2COO—NH4+.