WO2019230844A1 - （ｚ）－１－クロロ－２，３，３，４，４，５，５－ヘプタフルオロ－１－ペンテンの製造方法 - Google Patents

（ｚ）－１－クロロ－２，３，３，４，４，５，５－ヘプタフルオロ－１－ペンテンの製造方法 Download PDF

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WO2019230844A1
WO2019230844A1 PCT/JP2019/021403 JP2019021403W WO2019230844A1 WO 2019230844 A1 WO2019230844 A1 WO 2019230844A1 JP 2019021403 W JP2019021403 W JP 2019021403W WO 2019230844 A1 WO2019230844 A1 WO 2019230844A1
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dycc
composition
distillation
water
chloro
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PCT/JP2019/021403
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English (en)
French (fr)
Japanese (ja)
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卓也 岩瀬
聡史 河口
高木　洋一
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Ａｇｃ株式会社
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Priority to JP2020522271A priority Critical patent/JP7310807B2/ja
Priority to CN201980036731.2A priority patent/CN112218843B/zh
Publication of WO2019230844A1 publication Critical patent/WO2019230844A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine

Definitions

  • the present invention relates to a method for producing (Z) -1-chloro-2,3,3,4,4,5,5-heptafluoro-1-pentene.
  • Hydrochlorofluorocarbons have a negative impact on the ozone layer and are therefore expected to be regulated.
  • HCFC 3,3-dichloro-1,1,1,2,2-pentafluoropropane (CF 3 -CF 2 -CHCl 2 , HCFC-225ca), 1,3-dichloro-1,1,2, 2,3-pentafluoropropane (CClF 2 —CF 2 —CHFCl, HCFC-225cb) and the like can be given.
  • HCFC regulations development of alternative compounds is desired.
  • HCFC 1-chloro-2,3,3,4,4,5,5-heptafluoro-1-pentene
  • CHCl CF—CF 2 —CF 2 —CF 2 H, HCFO-1437 dycc
  • 1437 dycc has a low global warming potential (GWP), and is expected as a compound suitable for applications such as cleaning agents, solvents, refrigerants, foaming agents, and aerosols.
  • GWP global warming potential
  • Non-Patent Document 1 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (hereinafter referred to as “OFPO”) is reacted with dichlorotriphenylphosphorane.
  • -Chloro-1,1,2,2,3,3,4,4-octafluoropentane (HCFC-448 occc; hereinafter referred to as "448 occc" is obtained, and then 448 occc is reacted with sodium methoxide.
  • a method of dehydrating 448 occc to obtain 1437 dycc is disclosed.
  • the reaction product obtained by the above conventional method includes (Z) -1-chloro-2,3,3,4,4,5,5-heptafluoro-1-pentene (hereinafter referred to as “1437 dycc (Z)”). And (E) -1-chloro-2,3,3,4,4,5,5-heptafluoro-1-pentene (hereinafter referred to as “1437 dycc (E)”). .
  • 1437 dycc (Z) or 1437 dycc (E) may be used alone, or 1437 dycc (Z) and 1437 dycc (E) may be mixed and used in a desired ratio.
  • 1437 dycc (E) and 1437 dycc (Z) may be mixed and used in a desired ratio.
  • the difference between the boiling points of 1437 dycc (E) and 1437 dycc (Z) is small (the boiling point of 1437 dycc (E) is about 93 ° C. and the boiling point of 1437 dycc (Z)) is about 89 ° C.)
  • the present invention has been made to solve the above-mentioned problems, and can efficiently remove 1437 dycc (E) from a composition containing 1437 dycc (E) and 1437 dycc (Z). It is an object of the present invention to provide a method for producing 1437 dycc (Z) which has a high recovery rate and increases the purity of 1437 dycc (Z).
  • the present invention provides a method for producing 1437 dycc (Z) having the following configuration.
  • 1437 dycc (E) can be efficiently removed from a composition containing 1437 dycc (Z) and 1437 dycc (E). Therefore, the recovery rate of 1437 dycc (Z) can be increased, and the purity of 1437 dycc (Z) can be increased.
  • Embodiments of the present invention will be described below.
  • the composition for distillation containing 1437 dycc (Z), 1437 dycc (E) and water is removed.
  • 1437 dycc (Z) is refine
  • 1437 dycc (E) and water in the composition for distillation may be partially removed, or all may be removed.
  • 1437 dycc (E) and water in the distillation composition are removed from the distillation composition by forming an azeotrope or azeotrope-like composition upon distillation of the distillation composition. It is preferable.
  • an azeotropic composition is a mixture of two or more compounds, in which the composition of the gas phase generated by vaporization of the liquid phase is the same as the composition of the liquid phase or by liquefaction of the gas phase.
  • the composition of the liquid phase produced is the same as the composition of the gas phase.
  • An azeotropic composition can be suitably used for distillation and reflux because the composition does not change due to evaporation or condensation. Note that the composition of the azeotropic composition varies depending on the pressure condition.
  • the azeotrope-like composition behaves similarly to the azeotrope composition. That is, in the azeotrope-like composition, the composition of the gas phase generated by vaporization of the liquid phase is substantially the same as the composition of the liquid phase, or the composition of the liquid phase generated by liquefaction of the gas phase is the gas phase.
  • the composition is substantially the same. Since an azeotrope-like composition hardly changes in composition due to evaporation and condensation, it can be suitably used for distillation and reflux as in the case of an azeotrope composition.
  • the present inventors have found that 1437 dycc (E) and water form an azeotropic composition or an azeotrope-like composition. Furthermore, it has been found that an azeotrope or azeotrope-like composition comprising 1437 dycc (E) and water is formed in preference to an azeotrope or azeotrope-like composition comprising 1437 dycc (Z) and water. It was.
  • the azeotropic composition or azeotrope-like composition consisting of 1437 dycc (E) and water has a lower boiling point than 1437 dycc (Z). That is, the boiling point of 1437 dycc (Z) is about 89 ° C., whereas the boiling point of an azeotropic or azeotrope-like composition comprising 1437 dycc (E) and water is about 80 to 88 ° C.
  • the boiling point is a boiling point under atmospheric pressure. The atmospheric pressure is 101.325 kPa.
  • 1437 dycc (E) and water from a distillation composition comprising 1437 dycc (Z), 1437 dycc (E) and water Can be separated.
  • 1437 dycc (E) and water can be efficiently removed from the composition for distillation, the recovery rate of 1437 dycc (Z) can be increased, and the purity of 1437 dycc (Z) can be increased.
  • the azeotropic composition comprising 1437 dycc (E) and water has a relative volatility of 1.00 to 1437 dycc (E) represented by the following formula (1) at atmospheric pressure, and 1437 dycc (E) and water.
  • the relative volatility represented by the following formula (1) is a value in the range of 1.00 ⁇ 0.20.
  • the azeotrope-like composition can obtain substantially the same effect as the azeotrope composition as long as the relative volatility is within the above range.
  • the composition range in which the desired relative volatility can be obtained can be obtained as follows. First, the composition of the mixture of 1437 dycc (E) and water is gradually changed, and the composition of the liquid phase and the gas phase is measured by a Karl Fischer moisture meter or a gas chromatograph. Using this liquid phase and gas phase composition, the relative volatility is determined from the above formula (1). Thereby, the correlation with a composition and a relative volatility is calculated
  • the ratio of the amount of 1437 dycc (E) to the total amount of 1437 dycc (E) and water is 0.01 to 90% by mass. preferable. If the ratio is within the above range, the relative volatility tends to be within the range of 1.00 ⁇ 0.20, and the boiling point tends to be about 80 to 88 ° C. From the viewpoint of reducing the boiling point by bringing the relative volatility closer to 1.00, the above ratio is more preferably 0.03 to 70% by mass, further preferably 0.05 to 50% by mass, and It is particularly preferably 1 to 30% by mass.
  • composition for distillation contains 1437 dycc (Z), 1437 dycc (E) and water.
  • the composition for distillation will not be specifically limited if it is a composition containing 1437 dycc (Z), 1437 dycc (E), and water.
  • the composition for distillation may contain components other than 1437 dycc (Z), 1437 dycc (E), and water.
  • the composition for distillation may be liquid or gas.
  • the distillation composition can be prepared using a reaction composition containing 1437 dycc (Z) and 1437 dycc (E), which is generated when 1437 dycc (Z) is obtained by a method described later. That is, when 1437 dycc (Z) and 1437 dycc (E) are contained in the reaction product produced when obtaining 1437 dycc (Z), water is added to this to prepare a distillation composition. it can. Moreover, when 1437 dycc (Z), 1437 dycc (E), and water are contained in the reaction product produced
  • composition after the reaction product is washed with water or alkali to remove acidic substances such as hydrogen fluoride and hydrogen chloride contained in the reaction product is usually added to 1437 dycc (Z) and 1437 dycc (E). Since it contains water, it can be used as a composition for distillation.
  • “preparing” a composition includes the case where the above-described reaction composition or the like is used as it is.
  • the dehydrofluorination reaction can be performed by either a liquid phase reaction or a gas phase reaction.
  • the dehydrofluorination reaction in a liquid phase reaction refers to the dehydrofluorination reaction of 448 occc in a liquid state.
  • the dehydrofluorination reaction in a gas phase reaction means the dehydrofluorination reaction of 448 occc in a gaseous state.
  • the 448 occc dehydrofluorination reaction is preferably performed by a liquid phase reaction in terms of reaction efficiency.
  • the base may be any base that can perform the dehydrofluorination reaction, and examples thereof include metal hydroxides, metal oxides, metal carbonates, and metal alkoxides.
  • a base may be used individually by 1 type and may use 2 or more types together.
  • metal hydroxides include alkali metal hydroxides and alkaline earth metal hydroxides.
  • alkali metal hydroxide include lithium hydroxide, sodium hydroxide, and potassium hydroxide.
  • alkaline earth metal hydroxide include magnesium hydroxide, calcium hydroxide, strontium hydroxide, and barium hydroxide.
  • metal oxides include alkali metal oxides and alkaline earth metal oxides.
  • alkali metal oxide include sodium oxide.
  • alkaline earth metal oxide include calcium oxide.
  • metal carbonates include alkali metal carbonates and alkaline earth metal carbonates.
  • alkali metal carbonate include lithium, sodium or potassium carbonate.
  • Alkaline earth metal carbonates include beryllium, magnesium, calcium, strontium or barium carbonate.
  • Examples of the metal alkoxide include alkali metal alkoxides.
  • Examples of the alkali metal alkoxide include sodium methoxide, sodium ethoxide, potassium methoxide, and potassium ethoxide.
  • metal hydroxides are preferable and potassium hydroxide and sodium hydroxide are more preferable because they are easy to handle and have high reactivity.
  • the above metal hydroxide is preferably used because of its high solubility in water.
  • the dehydrofluorination reaction is performed by a liquid phase reaction, it is preferably performed in the presence of a phase transfer catalyst in order to increase the reaction rate.
  • phase transfer catalyst examples include quaternary ammonium salts, quaternary phosphonium salts, quaternary arsonium salts, sulfonium salts, crown ethers, quaternary ammonium salts, quaternary phosphonium salts, fourth compounds.
  • a quaternary arsonium salt and a sulfonium salt are preferable, and a quaternary ammonium salt is more preferable.
  • quaternary ammonium salt examples include tetra-n-butylammonium chloride (TBAC), tetra-n-butylammonium bromide (TBAB), and methyltri-n-octylammonium chloride (TOMAC).
  • TBAC tetra-n-butylammonium chloride
  • TBAB tetra-n-butylammonium bromide
  • TOMAC methyltri-n-octylammonium chloride
  • quaternary phosphonium salt examples include tetraethylphosphonium ion, tetra-n-butylphosphonium ion, ethyltri-n-octylphosphonium ion, cetyltriethylphosphonium ion, cetyltri-n-butylphosphonium ion, n-butyltriphenylphosphonium.
  • quaternary arsonium salt examples include triphenylmethylarsonium fluoride, tetraphenylarsonium fluoride, triphenylmethylarsonium chloride, tetraphenylarsonium chloride, and tetraphenylarsonium bromide.
  • the sulfonium salt include di-n-butylmethylsulfonium iodide, tri-n-butylsulfonium tetrafluoroborate, dihexylmethylsulfonium iodide, dicyclohexylmethylsulfonium iodide, dodecylmethylethylsulfonium chloride, tris (diethylamino) Examples include sulfonium difluorotrimethyl silicate.
  • crown ether examples include 18-crown-6, dibenzo-18-crown-6, and dicyclohexyl-18-crown-6.
  • phase transfer catalysts TBAC, TBAB, and TOMAC are preferred from the viewpoint of industrial availability, price, ease of handling, and reactivity.
  • the 448 occc dehydrofluorination reaction when carried out by a gas phase reaction, it can be carried out in the presence of activated carbon or a metal catalyst.
  • the specific surface area of the activated carbon used in the gas phase reaction from the viewpoint of improving the reaction conversion rate and the by-product suppression, preferably 10 ⁇ 3000m 2 / g, more preferably 20 ⁇ 2500m 2 / g, 50 ⁇ 2000m 2 / g is more preferable.
  • the specific surface area of the activated carbon is measured by a method based on the BET method.
  • activated carbon examples include activated carbon prepared from charcoal, coal, coconut shells, and the like. More specifically, there are formed coal having a length of about 2 to 5 mm, crushed coal having a length of about 4 to 50 mesh, granular coal, and powdered coal.
  • the amount of water in the activated carbon is preferably 10% by mass or less, more preferably 5% by mass or less, and more preferably 1% by mass when the total amount of activated carbon and moisture is 100% by mass from the viewpoint of improving reactivity and selectivity. The following is more preferable.
  • metal catalysts include zero-valent iron, zero-valent cobalt, zero-valent nickel, zero-valent palladium, chromium oxide (chromia), aluminum oxide (alumina), zinc oxide, tin oxide, magnesium oxide, and oxidation.
  • metal catalysts include zero-valent iron, zero-valent cobalt, zero-valent nickel, zero-valent palladium, chromium oxide (chromia), aluminum oxide (alumina), zinc oxide, tin oxide, magnesium oxide, and oxidation.
  • examples include lanthanum, nickel oxide, aluminum fluoride oxide, chromium fluoride oxide, magnesium fluoride oxide, lanthanum oxide fluoride, chromium hydroxide, alkali metal halide, and alkaline earth metal halide.
  • activated carbon or alkaline earth metal fluoride from the viewpoint of improving the reactivity and selectivity. More preferably, BaF 2 , SrF 2 , and CaF 2 are used.
  • the reaction product obtained by the 448 occc dehydrofluorination reaction usually contains water in addition to 1437 dycc. That is, a reaction composition containing 1437 dycc (Z), 1437 dycc (E) and water is obtained by the dehydrofluorination reaction of 448 occc.
  • the reaction composition obtained by the above method may be used as it is as a composition for distillation, or prepared by appropriately adding water according to the content of water and 1437 dycc (E) contained in the reaction composition. You may use what was done as a composition for distillation.
  • the reaction composition contains 1437 dycc (Z) and 1437 dycc (E), and does not contain water (first reaction composition), 1437 dycc (Z), and 1437 dycc (E) and water.
  • Reaction composition (second reaction composition).
  • the distillation composition can be obtained by adding water to the first reaction composition, that is, the reaction composition containing 1437 dycc (Z) and 1437 dycc (E) and not containing water.
  • the second reaction composition that is, a composition containing 1437 dycc (Z), water, and 1437 dycc (E) can be used as a composition for distillation as it is. Note that water can be added to the second reaction composition depending on the content of water and 1437 dycc (E).
  • the content of 1437 dycc (Z) in the distillation composition used in the present embodiment is preferably 50% by mass or more, more preferably 80% by mass or more, based on the total amount of the distillation composition. 90 mass% or more is more preferable. If the content of 1437 dycc (Z) is not less than the above lower limit, 1437 dycc (E) and water can be efficiently removed.
  • water and 1437 dycc (E) in the distillation composition are not necessarily limited.
  • an azeotropic composition or an azeotrope-like composition comprising water and 1437 dycc (E) can be formed.
  • the ratio of the content of 1437 dycc (E) to the total of the content of 1437 dycc (E) and the content of water in the composition for distillation is preferably 0.01 to 90% by mass.
  • the content is more preferably 03 to 70% by mass, further preferably 0.05 to 50% by mass, and particularly preferably 0.1 to 30% by mass.
  • the proportion of water in the composition for distillation can be prepared by adding water.
  • the ratio of water can be increased by adding water.
  • the composition for distillation may contain components other than 1437 dycc (Z), 1437 dycc (E) and water.
  • Components other than 1437 dycc (Z), 1437 dycc (E) and water are generated in addition to 1437 dycc (Z) and 1437 dycc (E) in the raw material for generating 1437 dycc (Z) and in the dehydrofluorination reaction of 448 occc. And by-products.
  • Specific examples of components other than 1437 dycc (Z), 1437 dycc (E) and water that can be included in the distillation composition include 448 occc, 1-chloro-3,3,4,4,5,5-hexafluoro.
  • Components other than 1437 dycc (Z), 1437 dycc (E) and water are preferably 30% by mass or less based on the total amount of the composition for distillation from the viewpoint of increasing the recovery rate of 1437 dycc (Z). More preferably, it is% or less.
  • alcohols such as OFPO and methanol may inhibit the formation of an azeotropic composition of 1437 dycc (E) and water, so when these compounds are included, the total amount of the composition for distillation is It is preferably 5% by mass or less, and more preferably 1% by mass or less.
  • the composition for distillation containing 1437 dycc (Z), 1437 dycc (E) and water is distilled.
  • an azeotropic composition or an azeotrope-like composition comprising 1437 dycc (E) and water can be formed.
  • distillation is performed by distilling the distillation composition. At least a part of the azeotropic composition or azeotrope-like composition comprising 1437 dycc (E) and water can be removed from the composition. As a result, a composition having a reduced content of 1437 dycc (E) and water, that is, a composition having an increased purity of 1437 dycc (Z) is obtained.
  • the distillation apparatus only needs to remove at least a part of the azeotropic composition or azeotrope-like composition composed of 1437 dycc (E) and water from the distillation composition, and a known distillation apparatus can be used.
  • FIG. 1 shows an example of a distillation apparatus.
  • the distillation apparatus 10 includes, for example, a distillation column 11.
  • the distillation column 11 includes a pipe 12 for supplying a distillation composition, a pipe 13 for taking a distillate from the top of the distillation tower 11, and a distillation tower. 11 is connected to a piping 14 for taking out the bottoms from the tower bottom.
  • the distillation apparatus 10 may be either a batch type or a continuous type.
  • the distillation column 11 may be either a hollow type or a multistage type.
  • a distillate containing an azeotropic composition comprising 1437 dycc (E) and water or an azeotrope-like composition
  • a distillate containing 1437 dycc (E) and water or an azeotrope-like composition can be obtained from the top of the column.
  • the bottoms containing 1437 dycc (Z) can be obtained from the tower bottom.
  • composition for distillation contains an excess of 1437 dycc (E) or water exceeding the composition range of the azeotropic composition or azeotrope-like composition comprising 1437 dycc (E) and water
  • Excess 1437 dycc (E) or water may be contained in, for example, bottoms from the bottom.
  • the composition for distillation is usually supplied to the middle stage of the multistage distillation column 10.
  • a distillate containing an azeotropic composition or an azeotrope-like composition composed of 1437 dycc (E) and water can be obtained from a stage above the stage where the distillation composition is supplied.
  • the bottoms containing 1437 dycc (Z) can be obtained from the stage below the stage to which the composition for distillation is supplied.
  • the pressure during distillation is preferably 30 to 760 mmHg in absolute pressure, more preferably 100 to 500 mmHg, and further preferably 200 to 400 mmHg.
  • the top temperature of the distillation column is preferably 10 to 95 ° C.
  • the top temperature of the distillation column is the recovered amount of distillate containing 1437 dycc (E) and water containing an azeotrope or azeotrope-like composition.
  • the top temperature of the distillation column is the recovered amount of distillate containing 1437 dycc (E) and water containing an azeotrope or azeotrope-like composition.
  • 45 ° C. or higher is preferable, 47 ° C. or higher is more preferable, and 49 ° C. or higher is even more preferable.
  • 57 degrees C or less is preferable, 55 degrees C or less is more preferable, and 53 degrees C or less is further more preferable.
  • Distillation can be performed again using the bottoms containing 1437 dycc (Z) as the composition for distillation.
  • 1437 dycc (E) and water are contained in the bottom product, 1437 dycc (E) and water can be separated by distillation, and the bottom product having an increased purity of 1437 dycc (Z) is obtained. Can be obtained.
  • the recovery rate of bottoms can be made into 85% or more by distilling, for example.
  • the recovery rate of the bottoms is preferably 90% or more, more preferably 95% or more.
  • the recovery rate of 1437 dycc (Z) in a bottom product can be made 90% or more by distilling, for example.
  • the recovery rate of 1437 dycc (Z) in the bottom product is preferably 93% or more, and more preferably 95% or more.
  • the recovery rate [%] of the bottoms can be obtained by the following formula from the amount of 1437 dycc (Z) in the composition for distillation and the amount of 1437 dycc (Z) in the bottoms.
  • the ratio of the content of 1437 dycc (Z) to the sum of the contents of 1437 dycc (Z), 1437 dycc (E) and water in the bottoms (purity of 1437 dycc (Z)) can be 85 mass% or more.
  • the proportion is preferably 90% by mass or more, more preferably 95% by mass or more, further preferably 98% by mass or more, and most preferably 99% by mass or more.
  • the content of 1437 dycc (E) in the bottom is preferably 2% by mass or less based on the total content of 1437 dycc (Z), 1437 dycc (E) and water.
  • the water content in the bottoms can be reduced.
  • the water content in the bottoms after contact with the solid adsorbent is preferably 200 ppm or less with respect to the sum of the contents of 1437 dycc (Z), 1437 dycc (E) and water.
  • Example 1 448 occc and tetra-n-butylammonium bromide (TBAB) were put into a reactor, and a 34 mass% potassium hydroxide (KOH) aqueous solution was added dropwise to carry out a 448 occc dehydrofluorination reaction at 30 ° C. After reacting for 8 hours, the organic layer was recovered to obtain a composition for distillation. As a distillation column, a multistage distillation column having 50 theoretical plates was prepared. The composition for distillation was supplied at a supply rate of 1.0 kg / h from the 20th stage from the top of this distillation column.
  • KOH potassium hydroxide
  • the composition for distillation contains 0.9490 kg / h of 1437 dycc (Z), 0.0500 kg / h of water, and 0.0010 kg / h of 1437 dycc (E). Thereafter, continuous distillation was performed at an operating pressure of 240 mmHg and a tower top temperature of 52.0 ⁇ 0.5 ° C.
  • the distillate was extracted from the top of the column and the bottom was extracted from the bottom. And about the distillate and the bottom thing, while calculating
  • Table 1 shows the supply amount of the composition for distillation, and also shows the recovery amount and recovery rate of the distillate and the bottom product.
  • Table 2 shows the composition of the distillation composition, distillate and bottom product.
  • composition of the composition for distillation is calculated
  • composition of the distillate and the bottom product is determined from the recovered amount of each component.
  • the recovery rate of the bottoms can be 93% by mass or more.
  • the proportion of the content of 1437 dycc (Z) in the bottoms can be 99% by mass or more.
  • Example 2 As shown in Table 3, the amount of each component in the composition for distillation was changed, and distillation and measurement were performed in the same manner as in Example 1.
  • Table 3 shows the recovery amount and recovery rate of the distillate and the bottom product, respectively.
  • Table 4 shows the composition of the distillation composition, the distillate, and the bottom product, respectively.
  • the recovery rate of bottoms can be 93% by mass or more.
  • the proportion of the content of 1437 dycc (Z) in the bottoms can be 99% by mass or more.
  • 1437 dycc (E) can be efficiently removed from a composition containing 1437 dycc, the recovery of 1437 dycc (Z) can be increased, and the purity of 1437 dycc (Z) can be increased. For this reason, it can be effectively used in a wide range of fields such as a cleaning agent, a solvent, and a refrigerant using 1437 dycc (Z). It should be noted that the entire contents of the specification, claims, abstract and drawings of Japanese Patent Application No. 2018-103780 filed on May 30, 2018 are cited herein as disclosure of the specification of the present invention. Incorporated.

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/JP2019/021403 2018-05-30 2019-05-29 （ｚ）－１－クロロ－２，３，３，４，４，５，５－ヘプタフルオロ－１－ペンテンの製造方法 WO2019230844A1 (ja)

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CN201980036731.2A CN112218843B (zh) 2018-05-30 2019-05-29 (z)-1-氯-2,3,3,4,4,5,5-七氟-1-戊烯的制造方法

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Citations (3)

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