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  • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
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  • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa

Definitions

• the present disclosure relates to a method for producing a perfluoroalkadiene compound.
• Perfluoroalkadiene compounds are compounds useful as various refrigerants, foaming agents, heat transfer media, etc. in addition to dry etching gases for semiconductors, and have two double bonds between carbon and carbon.
• hexafluorobutadiene having 4 carbon atoms and having double bonds at both ends is used in various applications.
• an organic metal compound such as Mg, Zn, Cd, Li or the like is used as a reactant at a desired temperature in the presence of an organic solvent, and ICF 2 CF 2 CF 2 CF 2 I A method by de-IFging such a compound is known (see, for example, Patent Document 1).
• a method for producing a perfluoroalkadiene compound it is also known that de-IF of a compound such as ICF 2 CF 2 CF 2 CF 2 I is performed in the presence of metallic zinc and a nitrogen-containing compound (for example, patents) Reference 2).
• the present disclosure aims to provide a method capable of obtaining a perfluoroalkadiene compound in a high yield while reducing the amount of impurities that are difficult to separate.
• the present disclosure includes the following configurations.
• X 1 , X 2 and X 3 are the same or different, X 1 and X 2 represent a halogen atom, and X 3 represents a chlorine atom, a bromine atom or an iodine atom. However, both X 1 and X 2 are not fluorine atoms.
• a reaction step of reacting a compound represented by The said reaction process is a manufacturing method including the mixing process of mixing sequentially the solution containing zinc or a zinc alloy, and an organic solvent, a nitrogen-containing compound, and the compound represented by the said General formula (2).
• the mixing step includes a step of mixing a solution containing zinc or a zinc alloy and an organic solvent with a nitrogen-containing compound, Item 2.
• the mixing step is a step of mixing a solution containing the zinc or zinc alloy and an organic solvent and the compound represented by the general formula (2), and then mixing the obtained mixed solution and the nitrogen-containing compound.
• the method according to Item 1 or 2 wherein Item 4.
• the solution containing the zinc or zinc alloy and the organic solvent and the nitrogen-containing compound are mixed, and then the obtained mixed solution and the compound represented by the general formula (2) are mixed.
• Item 3. The method according to Item 1 or 2.
• the compound represented by the general formula (2) is added to 1 mol of the zinc or zinc alloy with respect to the mixed solution of the zinc or zinc alloy and a solution containing an organic solvent and the nitrogen-containing compound.
• Item 5. The method according to Item 4, wherein the addition is performed at an addition rate of 0.05 to 30 mol / hour.
• Item 6. Item 6.
• Item 7. Item 7.
• Item 8. Item 8.
• X 1 and X 2 are the same or different and each represents a halogen atom. However, both X 1 and X 2 are not fluorine atoms.
• X 2 represents a halogen atom.
• X 1 and X 2 are the same or different and each represents a halogen atom.
• the said reaction process includes the mixing process which mixes a nitrogen-containing compound with respect to the solution containing zinc or a zinc alloy and an organic solvent.
• the yield is higher than the methods of Patent Documents 1 and 2, and 1,1,1,2,4,4,4-heptafluoro-2-butene and the like are separated from those of Patent Document 2. Impurities that are difficult to suppress can be suppressed, and the target product can be obtained.
• the CF 2 X 3 group and the adjacent group are CF 2 , so ClCF 2 CFClCF 2 CF 2 H, ICF 2 CF 2 CF 2 CF 2 H, BrCF 2 Impurities such as CF 2 CF 2 CF 2 H (compound represented by the general formula (5) described later) are produced in the liquid phase of the collection cylinder and hardly exist in the gas phase. For this reason, although it is an impurity which does not become a problem when extract
• a solution containing zinc or a zinc alloy and an organic solvent is mixed with a nitrogen-containing compound (particularly, a nitrogen-containing compound is added to a solution containing zinc or a zinc alloy and an organic solvent).
• a nitrogen-containing compound is added to a solution containing zinc or a zinc alloy and an organic solvent.
• n is an integer of 4 to 20, more preferably an integer of 4 to 10.
• X 1 and X 2 are halogen atoms, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• X 3 is a chlorine atom, a bromine atom or an iodine atom.
• X 1 , X 2 and X 3 may be the same or different. However, when both X 1 and X 2 are fluorine atoms, the reaction does not proceed and a perfluoroalkadiene compound cannot be obtained, so that both X 1 and X 2 do not become fluorine atoms.
• X 1 may be a chlorine atom, a bromine atom, an iodine atom, etc. (especially a chlorine atom)
• X 2 is preferably fluorine atom, chlorine atom, bromine atom, etc. (especially fluorine atom, chlorine atom, etc.)
• X 3 is chlorine atom, bromine atom, iodine atom, etc. (especially bromine atom).
• Iodine atom, etc. are preferable.
• Examples of the compound represented by the general formula (2) satisfying such conditions include ClCF 2 -CFCl-CF 2 -CF 2 I, ClCF 2 -CFCl-CF 2 -CF 2 -CF 2 I, ClCF 2 -CFCl-CF 2 -CF 2 -CF 2 I, ICF 2 -CF 2 -CF 2 I, ICF 2 -CF 2 -CF 2 -CF 2 -CF 2 I, ICF 2 -CF 2 -CF 2 -CF 2 -CF 2 I, BrCF 2 -CF 2 -CF 2 -CF 2 Br, BrCF 2 -CF 2 -CF 2 -CF 2 -CF 2 Br, BrCF 2 -CF 2 -CF 2 -CF 2 -CF 2 Br, BrCF 2 -CF 2 -CF 2 -CF 2 -CF 2 Br, BrCF 2 -CF 2 -CF 2 -CF 2 -CF 2 -CF 2 Br and the like.
• ClCF 2 -CFCl -CF 2 -CF 2 I ClCF 2 -CFCl-CF 2 -CF 2 -CF 2 I, ClCF 2 -CFCl-CF 2 -CF 2 -CF 2 I, BrCF 2 -CF 2 -CF 2- CF 2 Br, BrCF 2 -CF 2 -CF 2 -CF 2 -CF 2 Br, BrCF 2 -CF 2 -CF 2 -CF 2 -CF 2 -CF 2 Br, etc.
• ClCF 2 -CFCl-CF 2- CF 2 I ClCF 2 —CFCl—CF 2 —CF 2 —CF 2 I
• ClCF 2 —CFCl—CF 2 —CF 2 —CF 2 I ClCF 2 —CFCl—CF 2 —CF 2 —CF 2 I, and the like are more preferable.
• the amount of the compound represented by the general formula (2) is used from the viewpoint of obtaining a perfluoroalkadiene compound in a higher yield while reducing the amount of impurities that are difficult to separate, and zinc or a zinc alloy described later.
• 0.05 to 30 mol is preferable with respect to 1 mol, more preferably 0.1 to 10 mol, and still more preferably 0.2 to 5 mol.
• Examples of elements that can be contained in zinc or a zinc alloy when using a zinc alloy include lead, cadmium, and iron.
• Commercially available zinc may contain impurities such as lead, cadmium, and iron. The present disclosure includes those containing these impurities.
• a nonpolar organic solvent is particularly preferable from the viewpoint of dissolving the compound represented by the general formula (2).
• This organic solvent preferably has a boiling point equal to or lower than the boiling point of the nitrogen-containing compound from the viewpoint of suppressing the volatilization of the nitrogen-containing compound from the reaction system and particularly improving the yield of the perfluoroalkadiene compound.
• organic solvent include aromatic hydrocarbon compounds such as heptane, hexane, benzene, toluene, and xylene; ether compounds such as tetrahydrofuran and diethyl ether.
• the amount of the organic solvent used is not particularly limited as long as it is a solvent amount, and is preferably 0.01 to 10 mol, more preferably 0.1 to 5 mol, per 1 mol of zinc or zinc alloy.
• the nitrogen-containing compound is not particularly limited as long as it is a compound containing a nitrogen atom.
• amide compounds N, N-dimethylformamide, N, N-diisopropylformamide, etc.
• amine compounds triethylamine, etc.
• pyridine compounds Pyridine, methylpyridine, N-methyl-2-pyrrolidone, etc.
• quinoline compounds quinoline, methylquinoline, etc.
• These nitrogen-containing compounds can be used alone or in combination of two or more.
• amide compounds are preferred, and N, N-dimethylformamide is more preferred from the viewpoint of obtaining a perfluoroalkadiene compound in a higher yield while reducing the amount of impurities that are difficult to separate.
• This nitrogen-containing compound includes compounds that are liquid at room temperature, but from the viewpoint of obtaining a perfluoroalkadiene compound in a higher yield while reducing the amount of impurities that are difficult to separate, an additive rather than a solvent. It is preferable to use (use a small amount).
• the amount of the nitrogen-containing compound used is preferably 0.25 to 4 moles, more preferably 0.5 to 2 moles per mole of zinc or zinc alloy.
• the mixing step described above includes zinc or a zinc alloy and an organic solvent. It is preferable to sequentially mix the solution, the nitrogen-containing compound, and the compound represented by the general formula (2).
• a mixing step for example, a solution containing zinc or a zinc alloy and an organic solvent and a nitrogen-containing compound are mixed.
• a nitrogen-containing compound is added to a solution containing zinc or a zinc alloy and an organic solvent. can do.
• the content of each component is preferably adjusted so as to satisfy the content ratio of each component described above.
• the amount of the compound represented by the general formula (2) to be mixed (especially added) is taken into consideration. It is preferable to adjust the content of each component.
• the zinc or the zinc alloy and the organic solvent are mixed. It is preferable to mix the solution containing the nitrogen-containing compound at a temperature of preferably 50 to 200 ° C., more preferably 100 to 150 ° C. In particular, it is preferable to add the nitrogen-containing compound while heating a solution containing zinc or a zinc alloy and an organic solvent to the above temperature.
• the solvent is lower than the reaction temperature, so that it volatilizes when it reaches the reaction temperature, and it is cooled and returned to the reactor. be able to.
• the nitrogen-containing compound is added while refluxing the solution containing zinc or the zinc alloy and the organic solvent, it is most preferable to heat the solution containing zinc or the zinc alloy and the organic solvent at the reflux temperature.
• the boiling point of the organic solvent is equal to or lower than the boiling point of the nitrogen-containing compound, since the solution containing zinc or a zinc alloy and the organic solvent is heated and then mixed easily when the solution and the nitrogen-containing compound are mixed.
• a solution containing zinc or a zinc alloy and an organic solvent and a nitrogen-containing compound are mixed.
• adding a nitrogen-containing compound to a solution containing zinc or a zinc alloy and an organic solvent is zinc or 0.1 to 600 mol / hour is preferable and 0.33 to 60 mol / hour is more preferable with respect to 1 mol of the zinc alloy.
• the addition time is preferably set to such an extent that the reaction proceeds sufficiently, and particularly preferably adjusted so that the total amount of the nitrogen-containing compound added is in the above-described range. Specifically, the addition time is preferably 0.002 to 10 hours, more preferably 0.02 to 3 hours.
• a solution containing zinc or a zinc alloy and an organic solvent and a nitrogen-containing compound are mixed (particularly, a nitrogen-containing compound is added to a solution containing zinc or a zinc alloy and an organic solvent).
• the compound represented by the general formula (2) as a substrate may be mixed with a nitrogen-containing compound and a mixed solution obtained after mixing with a solution containing zinc or a zinc alloy and an organic solvent (hereinafter, (Sometimes referred to as “pre-substrate addition”), and a solution containing zinc or a zinc alloy and an organic solvent and a nitrogen-containing compound are mixed (particularly, a nitrogen-containing compound is added to a solution containing zinc or a zinc alloy and an organic solvent) After that, the mixed solution thus obtained and the substrate are mixed with the compound represented by the general formula (2) (particularly, the mixed solution obtained in this way is a general formula which is a substrate).
• a compound represented by the general formula (2) which is a substrate, is added to the mixed solution thus obtained after adding a nitrogen-containing compound to a solution containing zinc or a zinc alloy and an organic solvent.
• the addition rate (dropping rate) of the compound represented by the general formula (2) in the case of adding a perfluoroalkadiene compound represented by the general formula (1) while reducing the amount of impurities that are difficult to separate Is more preferably 0.05 to 30 mol / hour, more preferably 0.17 to 6 mol / hour with respect to 1 mol of zinc or zinc alloy.
• the addition time is preferably adjusted so that the reaction proceeds sufficiently, and in particular, it is preferably adjusted so that the total amount of the compound represented by the general formula (2) is within the above-mentioned range. Specifically, the addition time is preferably 0.02 to 10 hours, and more preferably 0.08 to 3 hours.
• an iodine-containing inorganic material can be used in the reaction.
• the perfluoroalkadiene compound represented by the general formula (1) can be obtained in a higher yield while reducing the amount of impurities that are difficult to separate.
• the inorganic material containing iodine is not particularly limited as long as it is an inorganic material containing an iodine atom.
• iodine typical metal iodide (sodium iodide, potassium iodide, magnesium iodide, calcium iodide, etc.), transition Examples thereof include metal iodides such as metal iodide (such as zinc iodide).
• zinc halide a mixture of zinc fluoride, zinc chloride, and zinc iodide
• zinc halide a mixture of zinc fluoride, zinc chloride, and zinc iodide
• Zinc halide as an impurity contained in the product can be used as an iodine-containing inorganic material and reused in the production method of the present disclosure.
• These iodine-containing inorganic materials can be used alone or in combination of two or more.
• Zinc halide, etc. are preferable, and iodine is more preferable.
• the amount of the iodine-containing inorganic compound used is 0.0005 mol or more with respect to 1 mol of zinc or zinc alloy from the viewpoint of obtaining a higher yield of perfluoroalkadiene compound while reducing the amount of impurities that are difficult to separate.
• the solubility is preferably not more than the solubility of the organic solvent, and more preferably 0.001 to 0.1 mol with respect to 1 mol of zinc or zinc alloy.
• the iodine-containing inorganic material is used in the present disclosure, whether the pre-substrate addition or the post-substrate addition is employed, the par.
• the iodine-containing inorganic material is preferably contained in a solution containing zinc or a zinc alloy and an organic solvent. In this case, it is preferable to adjust so that the content of the iodine-containing inorganic material contained in the solution containing zinc or the zinc alloy and the organic solvent satisfies the content ratio of each component described above.
• reaction atmosphere is preferably an inert gas atmosphere (nitrogen gas atmosphere, argon gas atmosphere, etc.), and the reaction time (maintenance time at the highest temperature reached) is sufficient for the reaction. It can be a degree of progress.
• purification can be performed according to a conventional method to obtain a perfluoroalkadiene compound represented by the general formula (1).
• the yield of the perfluoroalkadiene compound represented by the general formula (1) is increased while reducing the amount of impurities that are difficult to separate.
• the perfluoroalkadiene compound represented by the general formula (1) can be efficiently obtained while reducing the effort for isolating difficult impurities.
• the impurities that are difficult to separate are, for example, 1,1,1,2,4,4,4-hepta when trying to obtain hexafluorobutadiene as a perfluoroalkadiene compound represented by the general formula (1).
• fluoro-2-butene CF 3 CF ⁇ CHCF 3 ).
• the perfluoroalkadiene compound represented by the general formula (1) thus obtained includes an etching gas for forming a state-of-the-art microstructure such as a semiconductor and a liquid crystal, a refrigerant, a heat transfer medium, a foam It can be effectively used for various uses such as an agent and a resin monomer.
• a perfluoroalkadiene compound represented by the general formula (1) can be obtained.
• the perfluoroalkadiene compound represented by the general formula (1) and the general formula (3): CF 2 CF- (CF 2 ) n-4 -CF 2 -CF 2 H (3) [Wherein n is the same as defined above. ]
• a compound represented by the general formula (4A): CF 2 X 1 -CFX 2- (CF 2 ) n-4 -CF CF 2 (4A) [Wherein n is the same as defined above.
• X 1 and X 2 are the same or different and each represents a halogen atom. However, both X 1 and X 2 are not fluorine atoms.
• X 1 and X 2 are halogen atoms, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• X 1 and X 2 may be the same or different. However, as in the general formula (2), neither X 1 nor X 2 is a fluorine atom.
• X 1 is preferably a chlorine atom, bromine atom, iodine atom or the like (particularly chlorine atom, bromine atom, etc.), and X 2 is a fluorine atom, chlorine atom, bromine atom or the like (particularly fluorine). Atoms, chlorine atoms, etc.) are preferred.
• X 2 is a halogen atom, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• X 2 is preferably a fluorine atom, a chlorine atom, a bromine atom or the like (particularly a fluorine atom or a chlorine atom).
• Examples of the compound represented by the general formula (4B) satisfying such conditions include HCF 2 -CFCl-CF 2 -CF 2 H, HCF 2 -CFCl-CF 2 -CF 2 -CF 2 H, and HCF 2 -CFCl-CF 2 -CF 2 -CF 2 H, HCF 2 -CF 2 -CF 2 -CF 2 H, HCF 2 -CF 2 -CF 2 -CF 2 H, HCF 2 -CF 2 -CF 2 -CF 2 -CF 2 H and the like, and for the same reason as the general formula (2), HCF 2 -CFCl-CF 2 -CF 2 H, HCF 2 -CFCl-CF 2 -CF 2 -CF 2 H, HCF 2 -CFCl -CF 2 -CF 2 -CF 2 -CF 2 H and the like are preferable.
• X 1 and X 2 are halogen atoms, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• X 1 and X 2 may be the same or different. However, as in the general formula (2), neither X 1 nor X 2 is a fluorine atom.
• X 1 is preferably a chlorine atom, bromine atom, iodine atom or the like (particularly chlorine atom, bromine atom, etc.), and X 2 is a fluorine atom, chlorine atom, bromine atom or the like (particularly fluorine). Atoms, chlorine atoms, etc.) are preferred.
• the compound represented by the general formula (5) is a compound produced because the CF 2 X 3 group adjacent to the CF 2 X 3 group in the compound represented by the general formula (2) as a substrate is CF 2. Since it occurs in the liquid phase and hardly exists in the gas phase, it is not detected when only the gas phase of the collection cylinder is analyzed.
• the perfluoroalkadiene composition of the present disclosure is composed of impurities present in both the gas phase and the liquid phase of the collection cylinder. The disclosed perfluoroalkadiene composition is not obtained.
• Examples of the compound represented by the general formula (5) satisfying such conditions include ClCF 2 -CFCl-CF 2 -CF 2 H, ClCF 2 -CFCl-CF 2 -CF 2 -CF 2 H, ClCF 2 -CFCl-CF 2 -CF 2 -CF 2 H, ICF 2 -CF 2 -CF 2 H, ICF 2 -CF 2 -CF 2 -CF 2 -CF 2 H, ICF 2 -CF 2 -CF 2 -CF 2 -CF 2 H, BrCF 2 -CF 2 -CF 2 -CF 2 H, BrCF 2 -CF 2 -CF 2 -CF 2 -CF 2 H, BrCF 2 -CF 2 -CF 2 -CF 2 -CF 2 H, BrCF 2 -CF 2 -CF 2 -CF 2 -CF 2 -CF 2 H and the like, and for the same reason as in general formula (2), ClCF 2 -CFCl-CF 2 -CF 2 H, ClCF 2 -CFCl-CF
• the total amount of the perfluoroalkadiene composition of the present disclosure is 100 mol%, and the content of the perfluoroalkadiene compound represented by the general formula (1) is 30 to 99.8. Mol% (especially 50 to 99 mol%) is preferable, and the content of the compound represented by the general formula (3) is preferably 0.1 to 30 mol% (especially 2 to 25 mol%).
• the total content of the compound represented by (4B) is preferably 0.01 to 5 mol% (particularly 0.02 to 3 mol%), and the content of the compound represented by the general formula (5) is 0.05 to 35 mol% ( In particular, 0.1 to 5 mol% is preferable.
• the content of components other than the above (other components) is preferably 0 to 30 mol% (particularly 0.01 to 10 mol%).
• the product compound represented by the general formula (5) in order group adjacent the CF 2 X 3 group in the compound represented by a substrate general formula (2) is CF 2 is in the liquid phase
• the amount of the compound represented by the general formula (5) produced can be reduced.
• Such a perfluoroalkadiene composition of the present disclosure includes, as in the case of the above-mentioned perfluoroalkadiene compound alone, a coolant including an etching gas for forming a state-of-the-art microstructure such as a semiconductor and a liquid crystal. It can be effectively used for various applications such as heat transfer media, foaming agents and resin monomers.
• Example 1 ClCF 2 —CFCl —CF 2 —CF 2 I; pre-added; no iodine-containing inorganic material 200 g (0.53 mol) xylene and 34.93 g in a condenser eggplant flask connected to a trap cooled to ⁇ 78 ° C. (0.53 mol) of zinc was added, and 92 g (0.24 mol) of a raw material (ClCF 2 CFClCF 2 CF 2 I) was further added, and the mixture was heated with stirring until the internal temperature reached 140 ° C.
• N, N-dimethylformamide (DMF) is added dropwise at a dropping rate of 0.53 mol / hour (1 mol / hour with respect to 1 mol of zinc) for 1 hour while refluxing, and 3 hours with stirring. Heating at reflux was continued.
• Example 2 ClCF 2 -CFCl -CF 2 -CF 2 I; post-addition; no iodine-containing inorganic material 200 g (0.53 mol) xylene, 34.93 g in a condenser eggplant flask connected to a trap cooled to -78 ° C (0.53 mol) of zinc was added and heated with stirring until the internal temperature reached 140 ° C. After the internal temperature became constant, N, N-dimethylformamide (DMF) was added dropwise at a dropping rate of 0.52 mol / hour (1.04 mol / hour with respect to 1 mol of zinc) while refluxing, and the mixture was stirred for 0.5 hour. Heating at reflux was continued for an hour.
• DMF N-dimethylformamide
• Example 3 ClCF 2 —CFCl —CF 2 —CF 2 I; post-addition; ZnI 2 0.18 mol%
• the treatment was performed in the same manner as in Example 2 except that 0.30 g (0.001 mol; 0.18 mol% with respect to zinc) ZnI 2 was contained in the solution of xylene containing zinc.
• Example 4 ClCF 2 —CFCl —CF 2 —CF 2 I; post-addition; ZnI 2 0.6 mol% The treatment was performed in the same manner as in Example 2 except that 0.95 g (0.003 mol; 0.56 mol% with respect to zinc) ZnI 2 was contained in the xylene solution containing zinc.
• Example 5 ClCF 2 —CFCl —CF 2 —CF 2 I; post-added; ZnI 2 1.6 mol%
• the treatment was performed in the same manner as in Example 2 except that 2.70 g (0.53 mol; 1.6 mol% with respect to zinc) ZnI 2 was contained in the solution of xylene containing zinc.
• Example 6 ClCF 2 —CFCl —CF 2 —CF 2 I; post addition; I 2 1.6 mol%
• the treatment was performed in the same manner as in Example 2 except that 2.20 g (0.009 mol; 1.6 mol% with respect to zinc) I 2 was contained in the xylene solution containing zinc.
• Example 7 ClCF 2 —CFCl —CF 2 —CF 2 I; post addition; NaI 1.6 mol%
• the treatment was performed in the same manner as in Example 2 except that 1.27 g (0.0085 mol; 1.6 mol% with respect to zinc) NaI was contained in the solution of xylene containing zinc.
• Example 8 ClCF 2 -CFCl-CF 2 -CF 2 I; post-addition; NaI 3.2 mol%
• the treatment was performed in the same manner as in Example 2 except that 2.54 g (0.017 mol; 3.2 mol% with respect to zinc) NaI was contained in the solution of xylene containing zinc.
• Example 9 ICF 2 -CF2-CF 2 -CF 2 I; prior to addition; instead ClCF 2 -CFCl-CF 2 -CF 2 I as no iodine containing inorganic material substrate ICF 2 -CF2-CF 2 -CF 2 I The treatment was performed in the same manner as in Example 1 except that was used.
• Example 10 ICF 2 -CF2-CF 2 -CF 2 I; post-addition; instead ClCF 2 -CFCl-CF 2 -CF 2 I as no iodine containing inorganic material substrate ICF 2 -CF2-CF 2 -CF 2 I
• the treatment was performed in the same manner as in Example 2 except that was used.
• Example 11 ICF 2 -CF2-CF 2 -CF 2 I; post-addition; ZnI 2 1.6 mol% As substrate using the ClCF 2 -CFCl-CF 2 -CF 2 I rather ICF 2 -CF2-CF 2 -CF 2 I, in a solution of xylene containing zinc, 2.70 g (0.53 mol; with respect to zinc 1.6 mol%) ZnI 2 was included, and the same treatment as in Example 2 was performed.
• Example 12 BrCF 2 -CF2-CF 2 -CF 2 Br; pre-added; no iodine-containing inorganic material as substrate Substrate ClCF 2 -CFCl-CF 2 -CF 2 I but not BrCF 2 -CF2-CF 2 -CF 2 Br The treatment was performed in the same manner as in Example 1 except that was used.
• Example 13 BrCF 2 -CF2-CF 2 -CF 2 Br; post-addition; instead ClCF 2 -CFCl-CF 2 -CF 2 I as no iodine containing inorganic material substrate BrCF 2 -CF2-CF 2 -CF 2 Br The treatment was performed in the same manner as in Example 2 except that was used.
• Example 14 BrCF 2 -CF2-CF 2 -CF 2 Br; post-addition; ZnI 2 1.6 mol% As substrate using the ClCF 2 -CFCl-CF 2 -CF 2 I rather BrCF 2 -CF2-CF 2 -CF 2 Br, in a solution of xylene containing zinc, 2.70 g (0.53 mol; with respect to zinc 1.6 mol%) ZnI 2 was included, and the same treatment as in Example 2 was performed.

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