Method for producing iodine-containing compound, and iodine-containing compound
A method for producing an iodine-containing compound includes reacting a halogen-containing organic iodine compound and a compound containing a reactive carbon-carbon double bond in the presence of a compound of Formula (21) or Formula (22). Each of R 21 , R 23 and R 24 represents a hydrogen atom, an iodine atom, or an organic group having from 1 to 20 carbon atoms; R 22 represents a hydrogen atom, an iodine atom, an organic group having from 1 to 20 carbon atoms, or a boron-containing group; R 25 represents a hydrogen atom, an iodine atom, an organic group having from 1 to 20 carbon atoms, or a silicon-containing group; and each of A 1 and A 2 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom.
1 . A method for producing an iodine-containing compound, the method comprising reacting Compound (10) having a substructure represented by the following Formula (1) and a compound represented by the following Formula (3) in the presence of at least one selected from the group consisting of a compound represented by the following Formula (21) and a compound represented by the following Formula (22):
wherein, in Formula (1), * represents a binding site bonded to an organic group; X represents a fluorine atom or a chlorine atom; X 1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or —CX 5 X 6 X 7 ; and each of X 5 to X′ independently represents a hydrogen atom, a fluorine atom, or a chlorine atom;
wherein, in Formula (21), R 21 represents a hydrogen atom, an iodine atom, or a substituted or unsubstituted organic group having from 1 to 20 carbon atoms; R 22 represents a hydrogen atom, an iodine atom, a substituted or unsubstituted organic group having from 1 to 20 carbon atoms, or a boron-containing group, wherein a boron atom in the boron-containing group is bonded to the boron atom in Formula (21); R 21 and R 22 may be linked to form a ring structure; A 1 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom; and the boron atom in Formula (21) may be further coordinated with a ligand;
wherein, in Formula (22), each of R 23 and R 24 independently represents a hydrogen atom, an iodine atom, or a substituted or unsubstituted organic group having from 1 to 20 carbon atoms, and R 25 represents a hydrogen atom, an iodine atom, a substituted or unsubstituted organic group having from 1 to 20 carbon atoms, or a silicon-containing group, wherein a silicon atom in the silicon-containing group is bonded to the silicon atom in Formula (22), with the proviso that not all of R 23 to R 25 are hydrogen atoms; two or more of R 23 , R 24 , and R 25 may be linked to form a ring structure; and A 2 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom; and
wherein, in Formula (3), each of R 1 to R 4 independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a substituted or unsubstituted organic group having from 1 to 40 carbon atoms; and R 1 and R 4 , or R 2 and R 3 may be linked to form a ring structure.
2 . The method according to claim 1 ,
wherein, in Formula (3), each of R 1 to R 4 independently represents a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, or a substituted or unsubstituted organic group having from 1 to 40 carbon atoms and having at least one reactive carbon-carbon double bond, and R 1 and R 4 , or R 2 and R 3 may be linked to form a ring structure, and
wherein Formula (3) has at least two reactive carbon-carbon double bonds.
3 . The method according to claim 1 , wherein the compound represented by Formula (3) comprises a compound represented by the following Formula (5):
wherein, in the formula, X represents a fluorine atom or a chlorine atom; each of X 2 to X 4 independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or —CX 5 X 6 X 7 ; and each of X 5 to X′ independently represents a hydrogen atom, a fluorine atom, or a chlorine atom.
4 . The method according to claim 3 , wherein the iodine-containing compound obtained is a copolymer formed by copolymerization of a first compound represented by Formula (5) and a compound represented by Formula (3) that is different from the first compound.
5 . The method according to claim 4 , wherein the copolymerization is block copolymerization.
6 . The method according to claim 4 , wherein the copolymerization is random copolymerization or alternating copolymerization.
7 . The method according to claim 4 , wherein the compound represented by Formula (3) that is different from the first compound is at least one selected from the group consisting of ethylene, propylene, isobutylene, alkyl vinyl ether, hexafluoropropylene, perfluoro(alkyl vinyl ether), triallyl isocyanurate, 1,4-divinyl octafluorobutane, 1,6-divinyl dodecafluorohexane, vinyl acetate, styrene, butyl acrylate, and divinylbenzene.
8 . The method according to claim 3 , wherein the compound represented by Formula (5) is at least one selected from the group consisting of vinyl fluoride, vinylidene fluoride, trifluoroethylene, chlorotrifluoroethylene, bromotrifluoroethylene, iodotrifluoroethylene, tetrafluoroethylene, hexafluoropropylene, 1,3,3,3-tetrafluoropropylene, 2,3,3,3-tetrafluoropropylene, 1-chloro-1-fluoroethylene, 1-bromo-1-fluoroethylene, 1-iodo-1-fluoroethylene, 1,1-dibromo-2,2-difluoroethylene, 1,1-difluoro-2,2-diiodoethylene, 1,2-dichloro-1,2-difluoroethylene, 1,2-dibromo-1,2-difluoroethylene, 1,2-difluoro-1,2-diiodoethylene, vinyl chloride, and vinylidene chloride.
9 . The method according to claim 1 , wherein the Compound (10) is a compound represented by the following Formula (11) or a compound represented by the following Formula (12):
wherein, in the formulas, R 11 represents a perfluoroalkyl group having from 1 to 4 carbon atoms; R 12 represents a perfluoroalkylene group having from 1 to 4 carbon atoms; each X independently represents a fluorine atom or a chlorine atom; each of X 21 to X 23 independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or —CX 24 X 25 X 26 ; and each of X 24 to X 26 independently represents a hydrogen atom, a fluorine atom, or a chlorine atom.
10 . The method according to claim 1 , wherein the Compound (10) is a compound containing a plurality of units represented by the following Formula (4):
wherein, in the formula, each of X 31 to X 34 independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or —CX 35 X 36 X 37 ; and each of X 35 to X 37 independently represents a hydrogen atom, a fluorine atom, or a chlorine atom.
11 . The method according to claim 10 , wherein a fluorine content of the Compound (10) is 50% by mass or more.
12 . The method according to claim 1 ,
wherein the iodine-containing compound obtained is a polymer, and
wherein polydispersity of the polymer is 2.0 or less.
13 . The method according to claim 1 , wherein, in Formula (21), A 1 is a hydrogen atom and the boron atom has a ligand, or A 1 is an iodine atom.
14 . The method according to claim 1 , wherein, in Formula (22), at least one selected from the group consisting of R 23 , R 24 , and R 25 contains an aromatic ring.