Composition comprising a C7F14 acyclic perfluoroolefin and alcohol
A composition of acyclic perfluoroolefins and alcohols enables effective removal of impurities from PFH by phase separation, maintaining PFH's stability and enhancing safety and ease of handling methoxyperfluoroheptene synthesis.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- CHEMOURS MITSUI FLUOROPRODUCTS CO LTD
- Filing Date
- 2024-12-26
- Publication Date
- 2026-07-08
AI Technical Summary
Existing methods struggle to effectively remove side-chain-containing isomers and hydrogen-containing compounds from acyclic perfluoroolefins like perfluoroheptene (PFH), as distillation separation is ineffective due to similar boiling points and hydrogen-containing compounds persist post-distillation, affecting PFH's properties.
A composition comprising acyclic perfluoroolefins and alcohols, such as undecafluoro(trifluoromethyl)hexene and nonafluoro(pentafluoroethyl)pentene, is used for phase separation at specific temperatures, aided by alcohols like methanol or isopropyl alcohol, to remove these impurities without distillation, with optional alumina addition to suppress hydrolysis.
This method efficiently removes side-chain isomers and hydrogen-containing compounds with reduced heat load, ensuring PFH's stability and safety, avoiding hazardous chemicals and facilitating easy separation of methoxyperfluoroheptene synthesis.
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Figure 2026114136000001_ABST
Abstract
Description
[Technical Field]
[0001] This invention relates to the compositional formula C7F 14 This invention relates to a perfluoroheptene purification composition comprising an acyclic perfluoroolefin and an alcohol, and a method for removing side-chain-containing isomers and hydrogen-containing compounds derived from the perfluoroolefin using the composition. [Background technology]
[0002] Conventionally, compositions of hydrochlorofluorocarbon (e.g., HCFC-225) mixed with various surfactants have been used to remove residual water after cleaning precision metal parts, electronic parts, plastic parts, glass parts, etc., with water-soluble cleaning agents (Patent Documents 1 and 2). Hydrochlorofluorocarbons require the use of surfactants and are characterized by their ability to not damage the object being cleaned, their excellent properties such as low toxicity, non-flammability, and low corrosiveness, and their boiling point being suitable for the removal of the adhering water and the solvent itself. However, compounds containing chlorine atoms in their structure, such as hydrochlorofluorocarbons, have an ozone depletion potential (ODP), and their use has been restricted in recent years.
[0003] Therefore, perfluoroheptene (PFH), a type of acyclic perfluoroolefin, is expected to be a next-generation solvent due to its environmental characteristics, including an ozone depletion potential (ODP) of 0 and a global warming potential (GWP) of less than 5. PFH is used in a variety of applications, including various cleaning processes, heat transfer fluids, and dilution / dispersion solvents. It is also known to be used as one of the components of a polymer-based gas separation membrane (Patent Document 3) or as one of the components of an elastomer (Patent Document 4). However, PFH contains trace amounts of various isomers, perfluorocyclobutane, and hydrogen-containing compounds produced during its synthesis.
[0004] Examples of isomers (side-chain-containing isomers) of PFH include undecafluoro(trifluoromethyl)hexene and nonafluoro(pentafluoroethyl)pentene. These compounds readily hydrolyze to produce corresponding carboxylic acids, ketones, etc., affecting the properties of PFH. Another example of a by-product is perfluorocyclobutane (perfluoro(3-ethyl-4-methyl-cyclobutane)), and examples of hydrogen-containing compounds include chloroform (CHCl3). Perfluorocyclobutane significantly affects the electrical properties of PFH, and therefore its presence in PFH is undesirable. Therefore, in order to maintain the properties of PFH stably, it is necessary to minimize the amount of these side-chain isomers, perfluorocyclobutane, and hydrogen-containing compounds. Generally, distillation separation is used as a method to remove unintended compounds, but in the case of side-chain isomers and hydrogen-containing compounds in PFH, the side-chain isomers have boiling points close to those of PFH, making distillation separation impossible. Furthermore, hydrogen-containing compounds are still present in PFH even after repeated distillation purification, making it difficult to separate side-chain isomers and hydrogen-containing compounds from PFH by distillation alone. [Prior art documents] [Patent Documents]
[0005] [Patent Document 1] Japanese Patent Publication No. 2-204468 [Patent Document 2] Japanese Patent Application Publication No. 7-197091 [Patent Document 3] Japanese Patent Application Publication No. 60-099326 [Patent Document 4] Japanese Patent Application Publication No. 1-266119 [Overview of the project] [Problems that the invention aims to solve]
[0006] The present invention relates to the removal of side-chain-containing isomers and hydrogen-containing compounds contained in acyclic perfluoroolefins in order to stably maintain the properties of the acyclic perfluoroolefins. Specifically, the invention aims to provide a PFH purification composition comprising acyclic perfluoroolefin and an alcohol, and a method for removing side-chain-containing isomers and hydrogen-containing compounds using the composition. [Means for solving the problem]
[0007] The inventors diligently studied to solve the above problem and found that the composition formula C7F 14 We discovered that by using a composition containing acyclic perfluoroolefins and alcohols, it is possible to remove side-chain-containing isomers and hydrogen-containing compounds without distillation separation, thus completing the present invention.
[0008] In other words, the present invention is characterized by the following: [1] Composition formula C7F 14 A composition for purifying perfluoroheptene, comprising an acyclic perfluoroolefin and an alcohol. [2] Composition formula C7F 14 The composition according to [1], wherein the acyclic perfluoroolefin is at least one selected from undecafluoro(trifluoromethyl)hexene and nonafluoro(pentafluoroethyl)pentene. [3] Composition formula C7F 14 The composition according to [2], wherein the acyclic perfluoroolefin further comprises at least one selected from 1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluoro-3-heptene, 1,1,1,2,3,4,4,5,5,6,6,7,7,7-tetradecafluoro-2-heptene and their isomers. [4] The composition according to [3], wherein 1,1,1,2,2,3,4,5,5,6,6,7,7,7 - tetradecafluoro - 3 - heptene is cis - 1,1,1,2,2,3,4,5,5,6,6,7,7,7 - tetradecafluoro - 3 - heptene and / or trans - 1,1,1,2,2,3,4,5,5,6,6,7,7,7 - tetradecafluoro - 3 - heptene. [5] The composition according to [3], wherein 1,1,1,2,3,4,4,5,5,6,6,7,7,7 - tetradecafluoro - 2 - heptene is cis - 1,1,1,2,3,4,4,5,5,6,6,7,7,7 - tetradecafluoro - 2 - heptene and / or trans - 1,1,1,2,3,4,4,5,5,6,6,7,7,7 - tetradecafluoro - 2 - heptene. [6] The composition according to [1] or [2], wherein the alcohol is at least one alcohol selected from methanol, ethanol, and isopropyl alcohol. [7] The composition according to [1], comprising an acyclic perfluoroolefin of compositional formula C7F 14 in an amount of 80% by weight or more and less than 100% by weight, and an alcohol in an amount of 20% by weight or less, further comprising a hydrogen - containing compound. [8] The composition according to [1], further comprising aluminum oxide. [9] A method for removing undecafluoro(trifluoromethyl)hexene, nonafluoro(pentafluoroethyl)pentene, and / or a hydrogen - containing compound in an acyclic perfluoroolefin phase of compositional formula C7F 14 which comprises allowing the composition according to [1] or [7] to stand for phase separation and separating the acyclic perfluoroolefin phase of compositional formula C7F. 14
[10] The removal method according to [9], wherein the hydrogen - containing compound is chloroform.
[11] The removal method according to [9], which comprises allowing to stand at - 30 to 20 °C and selectively removing chloroform.
[12] The removal method according to [9], which comprises allowing to stand at 35 to 100 °C and selectively removing isomers of 1,1,1,2,3,4,4,5,5,5 - decafluoropentene and / or hydrogen - containing substances.
Advantages of the Invention
[0009] The composition for purifying PFH containing acyclic perfluoroolefin and alcohol of the general formula C7F 14 (hereinafter sometimes simply referred to as the composition) can be suitably used for removing side chain-containing isomers and hydrogen-containing compounds contained in the acyclic perfluoroolefin of the general formula C7F 14 . Furthermore, according to the removal method of the present invention, the side chain-containing isomers and hydrogen-containing compounds can be removed in a mode with less heat load on the acyclic perfluoroolefin of the general formula C7F 14 .
Brief Description of the Drawings
[0010] [Figure 1] As an example of an embodiment of the present invention, it is a graph showing the results of an experiment on the removal of CHCl3 from PFH using PFH / CHCl3 / IPA = 9 / 1 / 1 (weight ratio). [Figure 2] As an example of an embodiment of the present invention, it is a graph showing the results of an experiment on the removal of CHCl3 from PFH using PFH / CHCl3 / IPA = 9 / 1 / 10 (weight ratio). [Figure 3] As a comparative example of the present invention, it is a graph showing the influence of temperature on the removal of CHCl3 from PFH using PFH / CHCl3 = 9 / 1 (weight ratio). [Figure 4] It is a graph showing the results regarding the content of CHCl3 in the IPA phase related to the experiment of FIG. 1. [Figure 5] It is a graph showing the results regarding the content of CHCl3 in the IPA phase related to the experiment of FIG. 2.
Modes for Carrying Out the Invention
[0011] Hereinafter, the composition containing acyclic perfluoroolefin and alcohol of the general formula C7F 14 of the present invention, and the general formula C7F 14Composition formula C7F using a composition containing acyclic perfluoroolefins and alcohols 14 A detailed explanation will be given regarding the removal method for side-chain-containing isomers and hydrogen-containing compounds.
[0012] The composition of the present invention is of compositional formula C7F 14 The composition is characterized by comprising an acyclic perfluoroolefin and an alcohol.
[0013] The compositional formula of this invention C7F 14 The acyclic perfluoroolefin preferably contains PFH as its main component and has a boiling point of less than 100°C. Furthermore, the boiling point of the compound is preferably 50°C or higher, more preferably 60°C or higher, and even more preferably 70°C or higher. A boiling point of 50°C or higher allows for more effective purification.
[0014] The compositional formula of this invention C7F 14 Examples of acyclic perfluoroolefins other than PFH include undecafluoro(trifluoromethyl)hexene and nonafluoro(pentafluoroethyl)pentene. These compounds can be used individually with PFH, or as a mixture of several of these compounds with PFH.
[0015] Undecafluoro(trifluoromethyl)hexene and nonafluoro(pentafluoroethyl)pentene are called side-chain-containing isomers of PFH, which will be described later. The compositional formula of the present invention is C7F 14 The content of side-chain-containing isomers, namely undecafluoro(trifluoromethyl)hexene and / or nonafluoro(pentafluoroethyl)pentene, in the composition comprising the acyclic perfluoroolefin and alcohol is preferably less than 1% by weight.
[0016] There are no particular restrictions on the structural or stereoisomers of PFH; it may be a single isomer or a mixture of those isomers. Preferred examples of PFH include 1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluoro-3-heptene (perfluoro-3-heptene), 1,1,1,2,3,4,4,5,5,6,6,7,7,7-tetradecafluoro-2-heptene (perfluoro-2-heptene), and at least one selected from their isomers. More preferably, it is cis-perfluoro-3-heptene, trans-perfluoro-3-heptene, or a mixture containing them. In particular, a mixture mainly composed of trans-perfluoro-3-heptene is desirable.
[0017] The compositional formula of this invention C7F 14 Preferably, the perfluoroheptene content in the composition containing the acyclic perfluoroolefin and alcohol is 80% by weight or more and less than 100% by weight. More preferably, the perfluoro-3-heptene content is 80% by weight or more and less than 100% by weight, and the perfluoro-2-heptene content is less than 5% by weight. More preferably, the trans-perfluoro-3-heptene content is 80% by weight or more and less than 100% by weight, and the cis-perfluoro-3-heptene content is less than 5%.
[0018] In this invention, "alcohol" means alcohol that is soluble in water and liquid at room temperature. Specific examples of alcohols as used in this invention include, for example, lower alcohols such as methanol, ethanol, propanol, and butanol, and polyols such as ethylene glycol. Preferably, methanol, ethanol, and isopropyl alcohol (IPA) are used, and more preferably IPA. The compositional formula of this invention C7F 14 The alcohol content in the composition containing the acyclic perfluoroolefin and the alcohol is preferably 20% by weight or less.
[0019] The compositional formula of this invention C7F14 A composition containing an acyclic perfluoroolefin and an alcohol can be used to remove side-chain-containing isomers or hydrogen-containing compounds from the composition. The specific method is the composition formula C7F of the present invention 14 A composition containing an acyclic perfluoroolefin and an alcohol is allowed to stand to separate the phases, and then the composition formula C7F 14 The process consists of separating the acyclic perfluoroolefin phase and washing with water as necessary.
[0020] More specifically, the composition formula C7F 14 When removing the side-chain isomers in the acyclic perfluoroolefin, namely undecafluoro(trifluoromethyl)hexene and / or nonafluoro(pentafluoroethyl)pentene, the composition is allowed to stand at a high temperature above room temperature, preferably 35-100°C, more preferably 50-90°C, and particularly preferably 70°C, to separate the phases, and then the compositional formula C7F 14 The acyclic perfluoroolefin phase is separated to remove the side-chain-containing isomers. Specifically, by allowing the composition to stand at a temperature above room temperature, the side-chain-containing isomers react with the alcohol to synthesize methoxyperfluoroheptene, thereby resulting in a compound with formula C7F 14 The number of side-chain-containing isomers in the acyclic perfluoroolefin phase decreases.
[0021] Methoxyperfluoroheptene is a type of hydrofluoroolefin ether that possesses environmental characteristics such as an ozone depletion potential (ODP) of 0 and a global warming potential (GWP) of less than 10. For this reason, methoxyperfluoroheptene is also expected to be a next-generation solvent. The synthesis of methoxyperfluoroheptene typically involves using a solution of methanol dissolved in potassium hydroxide solution with PFH and a surfactant as catalysts. However, it is a highly toxic substance. Because it uses potassium hydroxide solution, a highly hazardous alkaline solution, and a highly viscous surfactant that is difficult to handle, its synthesis is highly dangerous in terms of handling and safety. In addition, the use of a highly viscous surfactant results in poor separation of perfluoromethoxyheptene from water after synthesis, making the isolation of perfluoromethoxyheptene time-consuming. Furthermore, there is a problem of contamination of the synthesized perfluoromethoxyheptene with the highly viscous surfactant and water. On the other hand, since the method for removing side-chain-containing isomers according to the present invention does not require the use of highly hazardous alkaline solutions and high-viscosity surfactants, the separation of methoxyperfluoroheptene is easy. For this reason, the removal method of the present invention can also be used as a synthesis method for methoxyperfluoroheptene, which is easy to handle and highly safe.
[0022] Composition formula C7F 14 To remove hydrogen-containing compounds (such as chloroform) from acyclic perfluoroolefins, the composition of the present invention is allowed to stand at a low temperature below room temperature, preferably -30 to 20°C, more preferably -20 to 2°C, and particularly preferably -15°C to separate the phases, and the composition formula C7F 14 The acyclic perfluoroolefin phase is separated to remove hydrogen-containing compounds. If necessary, washing with water may be performed after separation.
[0023] In both cases, when removing side-chain-containing isomers and when removing hydrogen-containing compounds, the composition formula C7F 14 It is preferable to add alumina to the composition containing acyclic perfluoroolefins and alcohols. Hydrolysis of side-chain-containing isomers generates fluoride ions, but these fluoride ions accelerate hydrolysis and produce carboxylic acids, triggering a hydrolysis chain and generating significant acidity, which is undesirable. Furthermore, fluoride ions are also found in compounds with the composition formula C7F other than side-chain-containing isomers. 14 This is undesirable because it also decomposes acyclic perfluoroolefins. Therefore, in some cases, it may be necessary to remove the carboxylic acid component. In the presence of alumina, contact between an alcohol and an acyclic perfluoroolefin reduces fluoride ions in the initial stages of hydrolysis of side-chain-containing isomers. This suppresses the generation of fluoride ions, which are essential for the hydrolysis chain of side-chain-containing isomers, and thus reduces the generation of carboxylic acid components. As a result, removal of carboxylic acid components becomes unnecessary, making it possible to efficiently remove side-chain-containing isomers and hydrogen-containing compounds.
[0024] The compositional formula of this invention C7F 14 The composition containing acyclic perfluoroolefins and alcohols can be used in a variety of applications, including as a heat transfer medium and a diluent / dispersant solvent. [Examples]
[0025] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.
[0026] <Raw material compound> The compounds used in the examples and comparative examples are as follows: PFH: Gas chromatography (manufactured by Shimadzu Corporation) confirmed that the mixture contained a total of 1.0% by weight of undecafluoro(trifluoromethyl)hexene and nonafluoro(pentafluoroethyl)pentene (side-chain isomers), and 0.3% by weight of perfluorocyclobutane. Chloroform was detected below the detection limit (boiling point 71.5°C). • Methanol: Reagent grade (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) • Ethanol: Reagent grade (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) • IPA: Reagent grade (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) • Chloroform: Reagent grade (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) • Aluminum oxide: Sumitomo Chemical Co., Ltd., KHD-24
[0027] <Analytical conditions for gas chromatography> Column: Restek Corporation, GC capillary column RTX-1, 105m Temperature: 60℃, Split ratio: 20
[0028] (Examples 1-6) 10 g of PFH (0.3 mol), alcohol, and aluminum oxide were sealed in a 100 ml glass bottle in the mixing ratios shown in Table 1. To compare the alcohols, i.e., to match the number of functional groups (-OH groups), the mixing ratio of PFH to alcohol was measured in molars. The glass bottle was left to stand in a 70°C oven for 7 days. Afterward, the glass bottle was cooled to room temperature, and the solution in the glass bottle was analyzed quantitatively using gas chromatography (Shimadzu GC-201A) under the above analytical conditions. The results are shown in Table 1. Here, "removal rate of side-chain-containing isomers" refers to the removal rate (by weight) of side-chain-containing isomers (undecafluoro(trifluoromethyl)hexene and nonafluoro(pentafluoroethyl)pentene) that were present in the PFH before treatment, and "perfluoroalkoxyheptene selectivity" refers to the ratio (by weight) of the generated perfluoroalkoxyheptene to the removed side-chain-containing isomers (undecafluoro(trifluoromethyl)hexene and nonafluoro(pentafluoroethyl)pentene). Furthermore, the weight of the generated perfluoroalkoxyheptene is the sum of the weights of methoxyheptene, ethoxyheptene, and isopropoxyheptene.
[0029] [Table 1]
[0030] In conventional purification methods using distillation separation, the composition formula C7F 14 It was not possible to remove the side-chain-containing isomers in the acyclic perfluoroolefin (for example, the PFH used in Examples 1 to 6 contained approximately 1% by weight). In contrast, the composition formula C7F 14By using a composition containing acyclic perfluoroolefins and alcohols, composition formula C7F 14 We were able to efficiently remove side-chain-containing isomers (undecafluoro(trifluoromethyl)hexene and nonafluoro(pentafluoroethyl)pentene) from acyclic perfluoroolefins.
[0031] (Example 7) The solution obtained first in Example 1 (0.3 mol of PFH and PFH:mol of alcohol) A mixture containing methanol in a 10:1 ratio and 10 g of aluminum oxide was mixed with an arbitrary amount of pure water. The resulting fluoride ions were extracted with the pure water, and the pure water was analyzed by ion chromatography. The results are shown in Table 2.
[0032] (Example 8) The solution obtained in the same manner as in Example 7, except that 10 g of aluminum oxide was not enclosed, was mixed with an arbitrary amount of pure water, and the generated fluoride ions were extracted with the pure water. The pure water was then analyzed by ion chromatography. The results are shown in Table 2.
[0033] [Table 2]
[0034] It was confirmed that the use of aluminum oxide in combination further reduces fluoride ions, which not only promote the hydrolysis of side-chain-containing isomers but also decompose acyclic perfluoroolefins other than side-chain-containing isomers.
[0035] (Example 9) A mixed solution of PFH, IPA, and chloroform (CHCl3) with a weight ratio of PFH / CHCl3 / IPA = 9 / 1 / 1 was sealed in a 100 ml glass bottle and allowed to stand after vigorous shaking at room temperature. Once the mixed solution separated into two phases and became clear, the upper phase (IPA-rich phase) and lower phase (PFH-rich phase) were quantitatively analyzed by gas chromatography (GC-201A, Shimadzu Corporation). The analytical conditions were as follows. After the analysis, the lower phase mixed solution (PFH-rich phase) was left to stand overnight in a freezer at -15°C. Upon standing, it separated into two phases again. The mixed solution was removed from the freezer, the lower phase (PFH-rich phase) was separated, and the lower phase was quantitatively analyzed by gas chromatography under the same analytical conditions. The results, along with the quantitative analysis of components obtained by storing the sample at room temperature instead of in a -15°C freezer, are shown in Figure 1. Similarly, the analysis results for the initial upper phase (IPA-rich phase) stored at room temperature / -15°C are shown in Figure 4. <Analysis conditions> Column: Restek Corporation, GC capillary column RTX-1, 105m Temperature: 60℃, Split ratio: 20
[0036] (Example 10) The same procedure as in Example 9 was followed, except that a mixed solution of PFH, IPA, and chloroform (CHCl3) was prepared with a weight ratio of PFH / CHCl3 / IPA = 9 / 1 / 10 (by weight). The component quantification analysis was performed by gas chromatography. The results, along with the component quantification analysis for samples stored at room temperature instead of in a -15°C freezer, are shown in Figure 2. Similarly, the analysis results for the IPA-rich phase, stored at room temperature and -15°C, are shown in Figure 5.
[0037] In both Example 9 and Example 10, it was confirmed that storing the samples at low temperatures reduced the chloroform (CHCl3) content in the PFH-rich phase (and increased the CHCl3 content in the IPA-rich phase).
[0038] (Comparative Example 1) A mixed solution of PFH and chloroform (CHCl3) with a weight ratio of PFH / CHCl3 = 9 / 1 was sealed in a 100 ml glass bottle. After vigorously shaking at room temperature and allowing it to stand, the components were quantitatively analyzed by gas chromatography, as in Examples 9 and 10. The analytical conditions were the same as in Example 9. After the analysis was completed, the lower phase mixed solution (PFH-rich phase) was left to stand overnight in a freezer at room temperature (20°C), 2°C, -20°C, and -30°C. The mixed solution was then removed from the freezer and the components were quantitatively analyzed by gas chromatography under the same analytical conditions. The results are shown in Figure 3. Unlike Examples 9 and 10 (where the solution contained alcohol), this comparative example, which did not contain alcohol, showed a high amount of chloroform (CHCl3) in the PFH-rich layer, confirming the importance of the alcohol component in the solution used for purification.
Claims
1. Compositional formula C 7 F 14 A composition for purifying perfluoroheptene, comprising an acyclic perfluoroolefin and an alcohol.
2. Compositional formula C 7 F 14 The composition according to claim 1, wherein the acyclic perfluoroolefin is at least one selected from undecafluoro(trifluoromethyl)hexene and nonafluoro(pentafluoroethyl)pentene.
3. Compositional formula C 7 F 14 The composition according to claim 2, wherein the acyclic perfluoroolefin further comprises at least one selected from 1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluoro-3-heptene, 1,1,1,2,3,4,4,5,5,6,6,7,7,7-tetradecafluoro-2-heptene and their isomers.
4. The composition according to claim 3, wherein 1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluoro-3-heptene is cis-1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluoro-3-heptene and / or trans-1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluoro-3-heptene.
5. The composition according to claim 3, wherein 1,1,1,2,3,4,4,5,5,6,6,7,7,7-tetradecafluoro-2-heptene is cis-1,1,1,2,3,4,4,5,5,6,6,7,7,7-tetradecafluoro-2-heptene and / or trans-1,1,1,2,3,4,4,5,5,6,6,7,7,7-tetradecafluoro-2-heptene.
6. The composition according to claim 1 or 2, wherein the alcohol is at least one alcohol selected from methanol, ethanol, and isopropyl alcohol.
7. Composition formula C: 80% or more by weight, and less than 100% by weight 7 F 14 The composition according to claim 1, comprising an acyclic perfluoroolefin and 20% by weight or less of an alcohol, and further comprising a hydrogen-containing compound.
8. The composition according to claim 1, further comprising aluminum oxide.
9. Allow the composition according to claim 1 or 7 to stand to separate the phases, Composition C 7 F 14 A method for removing undecafluoro(trifluoromethyl)hexene, nonafluoro(pentafluoroethyl)pentene, and / or hydrogen-containing compounds in the acyclic perfluoroolefin phase of Composition C, which comprises liquid separation of the acyclic perfluoroolefin phase of 7 F 14 .
10. The removal method according to claim 9, wherein the hydrogen-containing compound is chloroform.
11. The removal method according to claim 9, wherein the chloroform is selectively removed by standing at -30 to 20°C.
12. The removal method according to claim 9, comprising standing at 35 to 100°C to selectively remove isomers and / or hydrogen-containing substances of 1,1,1,2,3,4,4,5,5,5-decafluoropentene.