Method for producing fluorine-containing compound having iodine atom content reduced
The purpose of the present invention is to obtain a fluorine-containing compound which is easily stabilized without irradiation of ultraviolet light, by efficiently converting a C—I bond in an iodine-containing compound having a group represented by —CFRf—I (wherein Rf is a fluorine atom or a perfluoroalkyl group) to a C—H bond. A method for producing a fluorine-containing compound having an iodine atom content reduced than the following iodine-containing compound, which comprises subjecting an iodine-containing compound having a group represented by —CFRf—I (wherein Rf is a fluorine atom or a perfluoroalkyl group) to deiodinating treatment in the presence of an organic peroxide and a hydrogen-containing compound having a group represented by —CHR 1 —CHR 2 —CHR 3 — (wherein R 1 , R 2 and R 3 are each independently a hydrogen atom or an alkyl group).
1. A method for producing a fluorine-containing compound having an iodine atom content reduced than the following iodine-containing compound, which comprises subjecting an iodine-containing compound having a group represented by the following formula (1i) or a group represented by the following formula (2i), to deiodinating treatment in the presence of an organic peroxide and a hydrogen-containing compound having a group represented by the following formula (3):
in the formula (1i), Rf is a fluorine atom or a perfluoroalkyl group;
in the formula (2i), the ring containing Rf is a 5- or 6-membered ring, Rf is a perfluoroalkylene group having a linear or branched structure, which may have an etheric oxygen atom, and R a and R b are each independently a fluorine atom, a C 1-5 perfluoroalkyl group or a C 1-5 perfluoroalkoxy group, and
in the formula (3), R 1 , R 2 and R 3 are each independently a hydrogen atom or an alkyl group,
wherein the fluorine-containing compound has a group represented by the following formula (1h) or a group represented by the following formula (2h):
Rf in the formula (1h) and Rf′, R a and R b in the formula (2h) are as defined above.
2. The method according to claim 1 , wherein the iodine-containing compound is a compound represented by the following formula (4), or a compound represented by the following formula (5):
Q 1 -CFRf-I Formula (4)
Q 2 -(CFRf-I) 2 Formula (5)
in the formula (4), Rf is a fluorine atom or a perfluoroalkyl group, and Q 1 is a fluorine atom or a polyfluoroalkyl group which may have an etheric oxygen atom, and in the formula (5), Rf are each independently a fluorine atom or a perfluoroalkyl group, and Q 2 is a polyfluoroalkylene group which may have an etheric oxygen atom.
3. The method according to claim 1 , wherein the iodine-containing compound is a polymer compound which has at least one C—I bond, wherein all of hydrogen atoms bonded to carbon atoms are substituted by fluorine atoms.
4. The method according to claim 1 , wherein the organic peroxide has a 10 hour half-life temperature of from 10° C. to 150° C.
5. The method according to claim 4 , wherein the hydrogen-containing compound is an alkane.
6. The method according to claim 1 , wherein the total number of moles of the organic peroxide is from 0.0005 to 5 times to the total number of moles of iodine atoms in the iodine-containing compound.
7. The method according to claim 1 , wherein the total number of moles of the hydrogen-containing compound is from 5 to 500 times to the total number of moles of iodine atoms in the iodine-containing compound.
8. The method according to claim 1 , wherein the iodine-containing compound is treated in a fluorine-containing solvent.
9. The method according to claim 1 , wherein the iodine-containing compound is from 0.1 to 50 mass % of a reaction liquid for said deiodinating treatment.
10. The method according to claim 1 , wherein the hydrogen-containing compound is from 0.1 to 30 mass % of a reaction liquid for said deiodinating treatment.
11. The method according to claim 1 , wherein said deiodinating treatment is at a temperature between T° C. and T+80° C., where T° C. is the 10-hour half-life temperature of the organic peroxide.
12. The method according to claim 1 , wherein the iodine atom content in the fluorine-containing compound is at most 10% of the iodine atom content in the iodine-containing compound.