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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.
• X 1 , X 2 , X 3 and X 4 are the same or different and each represents a halogen atom.
• both X 1 and X 2 are not fluorine atoms, and both X 3 and X 4 are not fluorine atoms.
• Item 2. Item 2. The production method according to Item 1, wherein the amount of the iodine-containing inorganic material used is 0.0005 mol or more with respect to 1 mol of the zinc or zinc alloy and less than or equal to the solubility of the organic solvent.
• Item 3. Item 3.
• the production method according to Item 1 or 2 wherein the iodine-containing inorganic material is iodine and / or metal iodide.
• Item 4. Item 4.
• the reaction step includes a first mixing step of mixing the nitrogen-containing compound with a solution containing the iodine-containing inorganic material, the zinc or zinc alloy, and the organic solvent.
• the nitrogen-containing compound is added to the solution containing zinc or zinc alloy at an addition rate of 0.1 to 600 mol / hour with respect to 1 mol of zinc or zinc alloy.
• Item 6. Item 6.
• the second mixing step 0.05 to 30 mol / hour of the compound represented by the general formula (2) with respect to 1 mol of the zinc or the zinc alloy with respect to the mixed solution obtained in the first mixing step.
• Item 7. The method according to Item 6, which is added at an addition rate of Item 8.
• the first mixing step is a temperature of 50 to 200 ° C. when the nitrogen-containing compound and the solution containing the iodine-containing inorganic material, zinc or zinc alloy, and the organic solvent are mixed.
• the production method according to any one of the above.
• Item 9. Item 9.
• Item 10. Item 10.
• a compound represented by 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. ] And / or general formula (4B): CF 2 H-CFX 2- (CF 2 ) n-4 -CFX 3 -CF 2 H (4B) [Wherein n is the same as defined above. X 2 and X 3 are the same or different and each represents a halogen atom.
• n is the same as defined above.
• X 1 , X 2 and X 3 are the same or different and represent a halogen atom. However, both X 1 and X 2 are not fluorine atoms.
• Item 13 Item 13.
• Item 14. Item 14. An etching gas, a refrigerant, a heat transfer medium, a foaming agent, or a resin monomer comprising the perfluoroalkadiene composition according to any one of Items 11 to 13.
• X 1 , X 2 , X 3 and X 4 are the same or different and each represents a halogen atom. However, both X 1 and X 2 are not fluorine atoms, and both X 3 and X 4 are not fluorine atoms. ] The reaction process is made to react.
• 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.
• n is an integer of 4 to 20, more preferably an integer of 4 to 10.
• X 1 , X 2 , X 3 and X 4 are halogen atoms, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
• X 1 , X 2 , X 3 and X 4 may be the same or different. However, if both of X 1 and X 2 is fluorine atom, since no perfluoroalkadienes compound obtained without reaction proceeds when both X 3 and X 4 is fluorine atom, X 1 And X 2 is not a fluorine atom, and both X 3 and X 4 are not a fluorine atom.
• X 1 may be a chlorine atom, a bromine atom, an iodine atom, etc. (especially a chlorine atom)
• X 2 is preferably a fluorine atom, a chlorine atom, a bromine atom, etc. (especially a fluorine atom, a chlorine atom, etc.)
• X 3 is preferably a fluorine atom, a chlorine atom, etc. (especially a fluorine atom).
• X 4 is preferably a chlorine atom, a bromine atom, an iodine atom or the like (particularly a bromine atom or an iodine atom).
• 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.
• 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 Br, BrCF 2 -CF 2 -CF 2 -CF 2 -CF 2 Br 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.
• 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 mol, more preferably 0.5 to 2 mol, per 1 mol of zinc or zinc alloy described later.
• 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.
• 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.
• organic solvent a nonpolar organic solvent is particularly preferable from the viewpoint of dissolving the compound represented by the general formula (1), the iodine-containing inorganic material, and the like.
• This organic solvent preferably has a boiling point equal to or lower than that of the nitrogen-containing 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 compound represented by the general formula (2) is reacted in an organic solvent in the presence of a nitrogen-containing compound, an iodine-containing inorganic material, and zinc or a zinc alloy.
• the order of addition is not particularly limited, and can be added simultaneously or sequentially.
• a solution containing an iodine-containing inorganic material, the zinc or zinc alloy, and an organic solvent it is preferable to mix a nitrogen-containing compound (in particular, a nitrogen-containing compound is added to a solution containing an iodine-containing inorganic material, the zinc or zinc alloy, and an organic solvent).
• 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.
• a solution containing an iodine-containing inorganic material, the zinc or zinc alloy, and an organic solvent is mixed with a nitrogen-containing compound (the nitrogen-containing compound is added to the solution containing the iodine-containing inorganic material, the zinc or zinc alloy, and the organic solvent).
• a solution containing the iodine-containing inorganic material, the zinc or zinc alloy, and the organic solvent is preferably mixed with the nitrogen-containing compound at a temperature of 50 to 200 ° C., more preferably 100 to 150 ° C.
• a nitrogen-containing compound is preferably added to a solution containing an iodine-containing inorganic material, the zinc or zinc alloy, and an organic solvent, preferably at a temperature of 50 to 200 ° C, more preferably 100 to 150 ° C.
• the solvent is lower than the reaction temperature, so that it volatilizes when the reaction temperature is reached. It can also be returned to the reactor.
• the nitrogen-containing compound is added while refluxing a solution containing an iodine-containing inorganic material, zinc or a zinc alloy, and an organic solvent, it is most preferable to heat the solution at the reflux temperature.
• a solution containing the iodine-containing inorganic material, the zinc or zinc alloy and the organic solvent, and the nitrogen-containing compound are mixed.
• the addition rate reduces the amount of impurities that are difficult to separate.
• it is preferably 0.1 to 600 mol / hour, more preferably 0.33 to 60 mol / hour, with respect to 1 mole of the zinc or 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 an iodine-containing inorganic material, the zinc or zinc alloy, and an organic solvent and a nitrogen-containing compound are mixed (particularly, the iodine-containing inorganic material, the zinc or zinc alloy, and an organic solvent).
• the compound represented by the general formula (2) as a substrate is contained in a solution containing an iodine-containing inorganic material and the zinc or zinc alloy and an organic solvent.
• pre-substrate addition a solution containing the iodine-containing inorganic material, the zinc or zinc alloy, and the organic solvent, and the nitrogen-containing compound are mixed (in particular, After adding a nitrogen-containing compound to a solution containing the iodine-containing inorganic material, the zinc or zinc alloy, and the organic solvent), the solution and the substrate thus obtained are represented by the general formula (2) Mixed (in particular, thus adding a compound represented by the general formula (2) is a substrate to the resulting solution) may be (hereinafter also referred to as "additive after substrate”).
• the compound represented by the general formula (2) reacts with the nitrogen-containing compound to generate an impurity that is difficult to separate.
• post-substrate addition is particularly preferred.
• the content of the compound represented by the general formula (2) contained in the solution containing the iodine-containing inorganic material, the zinc or zinc alloy, and the organic solvent is the content of each component described above. It is preferable to adjust so that a ratio may be satisfy
• a nitrogen-containing compound is added to a solution containing an iodine-containing inorganic material and the zinc or zinc alloy and an organic solvent, and then the general formula (2
• the addition rate (dropping rate) of the compound represented by the general formula (2) when the compound represented by (1) is added is represented by the general formula (1) while reducing the amount of impurities that are difficult to separate.
• 0.05 to 30 mol / hour is preferable and 0.17 to 6 mol / hour is more preferable 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.
• 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 -CFX 3 -CF 2 H (3) [Wherein n is the same as defined above. X 3 represents a halogen atom. ]
• 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.
• X 3 is a halogen atom, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• X 3 is preferably a fluorine atom, a chlorine atom or the like (particularly a fluorine atom).
• 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 and X 3 are halogen atoms, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• X 2 and X 3 may be the same or different.
• X 2 is preferably a fluorine atom, chlorine atom, bromine atom or the like (especially fluorine atom or chlorine atom)
• X 3 is fluorine atom, chlorine atom or the like (especially fluorine atom). preferable.
• 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 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 in general formula (2), HCF 2 -CF 2 -CF 2 -CF 2 H, HCF 2 -CF 2 -CF 2 -CF 2 -CF 2 H, HCF 2 -CF 2 -CF 2 -CF 2 -CF 2 -CF 2 H and the like are preferable.
• X 1 , X 2 and X 3 are halogen atoms, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
• X 1 , X 2 and X 3 may be the same or different.
• 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.)
• X 2 is a fluorine atom, chlorine atom, bromine atom or the like (particularly fluorine).
• X 3 is preferably a fluorine atom, chlorine atom, etc. (particularly a fluorine atom).
• X 3 is a fluorine atom
• the compound represented by the general formula (5) is generated in the liquid phase and hardly exists in the gas phase, so only the gas phase of the collection cylinder is analyzed. If it does, it will not be detected. That is, 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.
• 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 80 to 99.8.
• the content of the compound represented by the general formula (3) is preferably 0.1 to 12 mol% (particularly 0.5 to 10 mol%), and the general formula (4A) and / or Alternatively, the total content of the compound represented by (4B) is preferably 0.01 to 0.6 mol% (particularly 0.02 to 0.5 mol%), and the content of the compound represented by the general formula (5) is 0.05 to 1 mol% ( Particularly preferred is 0.1 to 0.5 mol%).
• the content of components other than the above (other components) is preferably 0 to 5 mol% (particularly 0.01 to 4 mol%).
• 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; ZnI 2 0.18 mol% 200g (0.53mol) xylene, 34.93g (0.53mol) zinc, 0.30g (0.001mol; 0.18mol% with respect to zinc) ZnI 2 in a condenser eggplant flask connected to a trap cooled to -78 ° C The mixture was 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 2 ClCF 2 —CFCl —CF 2 —CF 2 I; ZnI 2 0.6 mol% The treatment was performed in the same manner as in Example 1 except that the amount of ZnI 2 used was 0.95 g (0.003 mol; 0.56 mol% based on zinc).
• Example 3 ClCF 2 —CFCl —CF 2 —CF 2 I; ZnI 2 1.6 mol% The treatment was performed in the same manner as in Example 1 except that the amount of ZnI 2 used was 2.70 g (0.53 mol; 1.6 mol% based on zinc).
• Example 4 ClCF 2 -CFCl-CF 2 -CF 2 I; I 2 1.6 mol% Treatment as in Example 1 except that 2.20 g (0.009 mol; 1.6 mol% with respect to zinc) I 2 was used instead of 0.30 g (0.001 mol; 0.18 mol% with respect to zinc) ZnI 2 Went.
• Example 5 ClCF 2 —CFCl —CF 2 —CF 2 I; NaI 1.6 mol% Treatment as in Example 1 except that 1.27 g (0.0085 mol; 1.6 mol% relative to zinc) NaI was used instead of 0.30 g (0.001 mol; 0.18 mol% relative to zinc) ZnI 2 went.
• Example 6 ClCF 2 -CFCl-CF 2 -CF 2 I; NaI 3.2 mol% The same treatment as in Example 1, except that 0.34 g (0.001 mol; 0.18 mol% relative to zinc) ZnI 2 was used instead of 2.54 g (0.017 mol; 3.2 mol% relative to zinc) NaI. went.
• Example 7 ICF 2 -CF2-CF 2 -CF 2 I; ZnI 2 1.6 mol% Using the ClCF 2 -CFCl-CF 2 In -CF 2 I without ICF 2 -CF2-CF 2 -CF 2 I as substrate, 2.70 g usage ZnI 2 (0.53mol; 1.6mol% relative to the zinc) The treatment was performed in the same manner as in Example 1 except that.
• Example 8 BrCF 2 -CF2-CF 2 -CF 2 Br; ZnI 2 1.6 mol% But using ClCF 2 -CFCl-CF 2 In -CF 2 I without BrCF 2 -CF2-CF 2 -CF 2 Br as a substrate was treated in the same manner as in Example 1.
• Reference Example 3 BrCF 2 -CF2-CF 2 -CF 2 Br; BrCF 2 -CF2-CF 2 -CF 2 Br was used instead of ClCF 2 -CFCl-CF 2 -CF 2 I as the substrate without iodine-containing inorganic material.
• the treatment was performed in the same manner as in Example 1 except that ZnI 2 was not used.

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