WO2021085134A1 - Composition comprenant du 1-chloro-2,3,3-trifluoro-1-propène et de l'eau et procédé de stockage de cette composition - Google Patents

Composition comprenant du 1-chloro-2,3,3-trifluoro-1-propène et de l'eau et procédé de stockage de cette composition Download PDF

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WO2021085134A1
WO2021085134A1 PCT/JP2020/038751 JP2020038751W WO2021085134A1 WO 2021085134 A1 WO2021085134 A1 WO 2021085134A1 JP 2020038751 W JP2020038751 W JP 2020038751W WO 2021085134 A1 WO2021085134 A1 WO 2021085134A1
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water
hexene
composition
chloro
propene
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PCT/JP2020/038751
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English (en)
Japanese (ja)
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崇勝 北元
翔太 河野
覚 岡本
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セントラル硝子株式会社
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Priority to JP2021554321A priority Critical patent/JPWO2021085134A1/ja
Publication of WO2021085134A1 publication Critical patent/WO2021085134A1/fr

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    • 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
    • C07C17/42—Use of additives, e.g. for stabilisation
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/30—Materials not provided for elsewhere for aerosols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/24—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/28—Organic compounds containing halogen
    • C11D7/30—Halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents

Definitions

  • One of the embodiments of the present invention relates to a composition containing 1-chloro-2,3,3-trifluoro-1-propene and water, and a method for storing the composition.
  • One of the problems of one of the embodiments of the present invention is to provide a method for stably preserving a composition containing 1-chloro-2,3,3-trifluoro-1-propene.
  • one of the embodiments of the present invention is to provide a composition containing 1-chloro-2,3,3-trifluoro-1-propene that can be stored for a long period of time.
  • One of the embodiments of the present invention is a composition containing 1-chloro-2,3,3-trifluoro-1-propene, an additive, and water.
  • One of the embodiments of the present invention is a method for preserving a composition, which comprises adding water and an additive to 1-chloro-2,3,3-trifluoro-1-propene.
  • One of the embodiments of the present invention is a composition containing 1-chloro-2,3,3-trifluoro-1-propene and water.
  • the composition containing 1-chloro-2,3,3-trifluoro-1-propene can be stably stored for a long period of time. Further, it is possible to provide a composition containing 1-chloro-2,3,3-trifluoro-1-propene, which can be stably stored for a long period of time.
  • composition containing 1-chloro-2,3,3-trifluoro-1-propene (hereinafter referred to as 1233yd) according to one of the embodiments of the present invention, and this composition are stably stored. The method of doing this will be described.
  • composition contains 1233 yd represented by the following formula and water.
  • the composition may further include additives.
  • 1-1.1233yd 1233yd which is a kind of chlorofluorocarbon, may be E-form (1233yd (E)), Z-form (1233yd (Z)), or a mixture thereof.
  • the ratio of E-form to Z-form can also be arbitrarily selected.
  • the ratio of E-form to the total amount of E-form and Z-form may be 1% or more and 99% or less, 1% or more and 50% or less, or 1% or more and 20% or less.
  • the ratio of E-form to Z-form may be calculated by nuclear magnetic resonance spectroscopy (NMR), or may be obtained from the area ratio of chromatograms of gas chromatography or liquid chromatography. When NMR is used, any of 1 H-NMR, 19 F-NMR, and 13 C-NMR may be used, but it is preferable to use 1 H-NMR or 19 F-NMR having high quantification.
  • This composition is due to its high dissolving power of 1233 yd to various solutes, nonflammability, large heat of vaporization, low boiling point, etc., and can be used as a solvent (solvent for lubricant coating liquid) used when applying a lubricant, or as a solvent for a lubricant coating liquid. It can be used for various purposes such as a heat medium, a refrigerant, a foaming agent, a solvent, a cleaning agent, a propellant, and a fire extinguishing agent.
  • this composition is also characterized in that it is less likely to cause global warming than conventional compositions mainly containing hydrofluorocarbons and hydrochlorofluorocarbons.
  • Bases used for defluorinated hydrogen include alkali metals such as sodium, potassium and lithium, or hydroxides of Group 2 elements such as magnesium, calcium, strontium and barium, carbonates, oxides, alkoxides and amides. Can be mentioned.
  • the base reacts with 244ca in a molar ratio of 1: 1 it may be used in an equimolar amount of 244ca or in an excess amount of 244ca.
  • the base is 1.0 equivalent or more and 3.0 equivalent or less, 1.0 equivalent or more and 2.0 equivalent or less, 1.0 equivalent or more and 1.5 equivalent or less, or 1.0 equivalent or more with respect to 244ca.
  • 1.2 Equivalent or less is appropriately selected.
  • the base is dissolved in water, an alcohol having 1 to 4 carbon atoms such as methanol, ethanol, isopropanol and 1-butanol, or an ether such as tetrahydrofuran and dioxane, and this base solution is added dropwise to a bulk solution of 1233 yd or 1233 yd.
  • Defluorinated hydrogen can be carried out at.
  • the solvent constituting the solution of 1233 yd is not limited, and examples thereof include the above-mentioned alcohols and ethers having 1 to 4 carbon atoms, and aromatic hydrocarbons such as toluene and xylene.
  • phase transfer catalyst For defluorinated hydrogen, a phase transfer catalyst may be used.
  • the phase transfer catalyst include quaternary ammonium salts, quaternary phosphonium salts, quaternary sulfonium salts, pyridine salts, crown ethers and the like.
  • the counter anions include chloride ion, bromide ion, iodide ion, hydroxide ion, phosphate ion, and p. -Toluene sulfonate ion and the like can be mentioned.
  • defluorinated hydrogen there is no restriction on the temperature of defluorinated hydrogen, and for example, it is appropriately selected from -40 ° C or higher and + 80 ° C or lower, -20 ° C or higher and + 60 ° C or lower, or 0 ° C or higher and + 40 ° C or lower.
  • a stabilizer may be added to the reaction system.
  • Stabilizers include alkenes (olefins) such as hexene, heptene, octene, pentadiene, cyclopentene and cyclohexene, aliphatic nitro compounds such as nitromethane, nitroethane and nitropropane, aromatic nitro compounds such as nitrobenzene, nitrotoluene and nitroaniline.
  • Ethers such as dimethoxymethane, 1,2-dimethoxyethane, 1,4-dioxane, 1,3,5-trioxane, tetrahydrofuran, glycidol, methylglycidyl ether, allylglycidyl ether, 1,2-butylene oxide, phenylglycidyl ether, Epoxy compounds such as cyclohexene oxide and epichlorohydrin, allyl alcohols such as phenol, olefinic alcohols such as 1-buten-3-ol; 3-methyl-1-butin-3-ol, 3-methyl-1-pentin-3-3 Examples thereof include acetylene-based alcohols such as oars, and acrylic acid esters such as methyl acrylate, ethyl acrylate, and butyl acrylate.
  • alkene such as octene
  • isomers may be present in alkenes, one isolated isomer may be used, or a mixture of two or more isomers may be used.
  • octene is used as a stabilizer, 1-octene, 2-octene, 3-octene, 4-octene, 2-methyl-1-hepten, 2-methyl-2-hepten, 2-methyl-3.
  • the organic layer is extracted, washed with an aqueous solution of a base such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, etc., and then washed with water.
  • a base such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, etc.
  • the organic layer may be further washed with saturated saline.
  • a crude product of 1233 yd can be obtained by simply dehydrating with a dehydrating agent such as magnesium sulfate or sodium sulfate.
  • the composition may be prepared without purifying the crude product, or the composition may be prepared using 1233 yd isolated by distillation purification.
  • the composition can be stably stored for a long period of time by adding water or water and an additive without performing the oxygen scavenging treatment of 1233 yd.
  • the amount of water contained in the water composition is 1233 yd obtained by distillation purification, or water is added to the crude product containing 1233 yd obtained by simple dehydration by any method, or dehydration treatment is performed. It can be adjusted by.
  • the distilled 1233 yd or the simply dehydrated 1233 yd crude product may be weighed and water may be dropped using a micropipette or a microsyringe.
  • an appropriate amount (for example, 5% by weight) of a dehydrating agent such as molecular sieves may be added and filtered.
  • the amount of water constituting the composition is higher than 200 ppm by weight and 1600 ppm by weight or less, higher than 200 wt ppm and 1400 wt ppm or less, higher than 200 wt ppm and 1200 wt ppm or less, 200 wt ppm or less with respect to 1233 yd. It is selected from a range higher than 1000 ppm by weight or greater than 200 ppm by weight and less than 500 ppm by weight.
  • the amount of water constituting the composition is 260 wt ppm or more and 1600 wt ppm or less, 260 wt ppm or more and 1400 wt ppm or less, 260 wt ppm or more and 1200 wt ppm or less, 260 wt ppm or more and 1000 wt ppm or less. It may be selected from the following range, or a range of 260 ppm by weight or more and 500 wt ppm or less.
  • the amount of water in the composition can be determined using, for example, a coulometric titration method. Water is preferably added to 1233 yd after being distilled, filtered, extracted, treated with an ion exchange resin or activated carbon.
  • Additives When the composition contains additives, the amount is 2 wt ppm or more and 5 wt% or less, 10 wt ppm or more and 2 wt% or less, 10 wt ppm or more and 1 wt% or less, or 10 wt ppm with respect to 1233 yd. Additives are added so as to be in the range of 0.5% by weight or less. Additives may be added in the same manner as when water is added. When the additive and the stabilizer used for defluorinated hydrogen are the same, the stabilizer remaining in the crude product may be used as the additive without adding the additive separately.
  • additives examples include nitro compounds, epoxy compounds, phenol derivatives, ethers, alcohols, imidazole derivatives, amines, unsaturated hydrocarbons and the like. Further, these may be used alone or in combination of two or more kinds of additives.
  • nitro compounds include aliphatic or aromatic nitro compounds.
  • the aliphatic nitro compound include nitromethane, nitroethane, 1-nitropropane, 2-nitropropane and the like.
  • Aromatic nitro compounds include, for example, nitrobenzene, o-, m-, or p-dinitrobenzene, trinitrobenzene, o-, m-, or p-nitrotoluene, o-, m-, or p-ethylnitrobenzene, 2 , 3-, 2,4-, 2,5-, 2,6-, 3,4-, or 3,5-dimethylnitrobenzene, o-, m-, or p-nitroacetophenone, o-, m-, Alternatively, p-nitrophenol, o-, m-, p-nitroanisole and the like can be mentioned.
  • epoxy compound examples include allyl glycidyl ethers such as ethylene oxide, 1,2-butylene oxide, propylene oxide, styrene oxide, cyclohexene oxide, glycidol, epichlorohydrin, glycidyl methacrylate and phenylglycidyl ether, methyl glycidyl ether, butyl glycidyl ether and 2-.
  • allyl glycidyl ethers such as ethylene oxide, 1,2-butylene oxide, propylene oxide, styrene oxide, cyclohexene oxide, glycidol, epichlorohydrin, glycidyl methacrylate and phenylglycidyl ether, methyl glycidyl ether, butyl glycidyl ether and 2-.
  • ethylhexyl glycidyl ether In addition to monoepoxy compounds exemplified by ethylhexyl glycidyl ether and the like, many such as diepoxybutane, vinylcyclohexendioxide, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, glycerin polyglycidyl ether, trimethylol propanthrglycidyl ether and the like. Examples include functional epoxy compounds.
  • phenol derivatives include an unsubstituted phenol and a compound having various substituents such as an alkyl group, an alkenyl group, an alkoxy group, a carboxyl group, a carbonyl group and a halogen together with a phenolic hydroxyl group on the aromatic ring.
  • substituents such as an alkyl group, an alkenyl group, an alkoxy group, a carboxyl group, a carbonyl group and a halogen together with a phenolic hydroxyl group on the aromatic ring.
  • examples of such phenol derivatives include 2,6-di-t-butyl-p-cresol, o-cresol, m-cresol, p-cresol, timol, pt-butylphenol, o-methoxyphenol, m.
  • phenol derivatives such as methoxyphenol, p-methoxyphenol, eugenol, isoeugenol, butylhydroxyanisole, xylenol, t-butylcatechol, 2,5-di-t-aminohydroquinone, 2,5-di
  • divalent phenol derivatives such as -t-butylhydroquinone.
  • ethers include dimethyl ether, diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, dipentyl ether, diisopentyl ether, ethyl methyl ether, ethyl propyl ether, ethyl isopropyl ether, ethyl isobutyl ether, ethyl isopentyl ether and ethyl vinyl ether.
  • Alcohols include methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol, 1-pentanol, 2-pentanol, 1- Ethyl-1-propanol, 2-methyl-1-butanol, 3-methyl-1-butanol, 3-methyl-2-butanol, neopentyl alcohol, 1-hexanol, 2-methyl-1-pentanol, 4-methyl -2-Pentanol, 2-Ethyl-1-butanol, 1-Heptanol, 2-Heptanol, 3-Heptanol, 1-Octanol, 2-Octanol, 2-Ethyl-1-Hexanol, 1-Nonanol, 3,5 5-trimethyl-1-hexanol, 1-decanol, 1-undecanol, 1-dodecanol, benzyl alcohol, cyclo
  • imidazole derivative examples include unsubstituted imidazole, 1-methylimidazole having an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group, or an aryl group as a substituent on nitrogen, 1-n-butylimidazole, and the like.
  • amines examples include pentylamine, hexylamine, diisopropylamine, diisobutylamine, di-n-propylamine, triethylamine, morpholine, N-methylmorpholine, benzylamine, dibenzylamine, ⁇ -methylbenzylamine, methylamine, and dimethylamine. , Trimethylamine, ethylamine, diethylamine, propylamine, isopropylamine, dipropylamine, butylamine, isobutylamine, dibutylamine, tributylamine, dipentylamine, trypentylamine, 2-ethylhexylamine, etc.
  • aromatic amines such as aniline, N-methylaniline, N, N-dimethylaniline, N, N-diethylaniline, diphenylamine and triphenylamine, and nitrogen-containing heteroaromatic compounds such as pyridine.
  • aromatic amines such as aniline, N-methylaniline, N, N-dimethylaniline, N, N-diethylaniline, diphenylamine and triphenylamine
  • nitrogen-containing heteroaromatic compounds such as pyridine.
  • it may be a polyfunctional amine such as ethylenediamine, propylenediamine, diethylenetriamine or tetraethylenepentamine, or it may be a herooxylamine such as diethylhydroxylamine.
  • unsaturated hydrocarbons include penten isomers such as 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, and 2-methyl-2-butene, 1-hexene, and 2-. Hexene, 3-hexene, 2-methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2-ethyl-1-butene, 3-ethyl-1-butene, 3-ethyl- Hexene isomers such as 2-butene, 2-methyl-2-pentene, 3-methyl-2-pentene, 4-methyl-2-pentene, 2,3-dimethyl-2-butene, 1-heptene, 2-heptene , 3-Hexene, 4-Hexene, Hexene isomers such as 3-ethyl-2-pentene, 1-octene, 2-octene, 3-octene, 4-octene, 2-methyl-1-hepten, 2- To Methyl
  • 1233yd is unstable to water and has been considered to be easily decomposed by water.
  • the decomposition of 1233 yd is effectively suppressed, and as a result, the composition containing 1233 yd can be stably stored for a long period of time. ..
  • the additive when the additive is contained in the composition, the amount of water added in the composition can be reduced.
  • the stability of 1233 yd is significantly improved even if the amount of water and the additive is several hundred ppm by weight with respect to 1233 yd, and the decomposition thereof. Can be effectively suppressed.
  • the stabilizer when synthesizing 1233 yd in the presence of a stabilizer, the stabilizer may not be completely removed from the generated 1233 yd.
  • the stabilizer can function as an additive for the composition containing 1233 yd, but the residual stabilizer alone cannot necessarily suppress the decomposition of 1233 yd.
  • the composition containing 1233 yd can be stabilized and stored for a long period of time.
  • composition containing 1233 yd and water, and the composition containing 1233 yd, water, and additives include, for example, polyethylene, polytetrafluoroethylene, tetrafluoroethylene / perfluoroalkoxyethylene copolymer, stainless steel, iron, and the like. It can be stored by sealing it in a container containing the metal, glass, or the like as a material. The inside of the container does not have to be coated, and the composition may come into contact with the above-mentioned material inside the container. Alternatively, a container made of a metal such as stainless steel or iron and having a glass-coated inner surface may be used.
  • an inert gas such as nitrogen or argon may be filled.
  • the container When glass is selected as the material, the container may be covered with a light-shielding film for shielding ultraviolet rays or visible light, or a glass container using glass containing iron oxide as the material may be used.
  • a glass ampoule When storing a small amount (for example, several mL to several hundred mL) of the composition, use a glass ampoule as a container, inject the composition into the ampoule, and then melt and seal a part of the composition. May be good.
  • the composition may be deoxidized before being sealed in the container. Thereby, the decomposition of 1233 yd by oxygen can be further suppressed.
  • the composition is solidified in a container using, for example, liquid nitrogen or dry ice, then the inside of the container is depressurized (for example, 10 Pa or more and 300 Pa), sealed, and allowed to stand until the temperature returns to the external environmental temperature. This operation may be repeated several times (for example, 2 to 5 times).
  • the composition may be deoxidized by bubbling an inert gas such as nitrogen or argon.
  • the decomposition of 1233yd is suppressed by adding water to 1233yd. Therefore, by constructing the composition so as to contain water, the composition can function as a solvent for a lubricant coating liquid, a heat medium, a refrigerant, a foaming agent, a solvent, a cleaning agent, a propellant, or a fire extinguisher for a long period of time. Not only can it be maintained, but it can also prevent corrosion, deterioration, and damage to the equipment that uses the composition.
  • 1233yd obtained by defluorinated hydrogen of 244ca was used as sample A
  • 1233yd obtained by precision distillation of sample A was used as sample B.
  • No deoxidizing treatment such as degassing treatment was performed on 1233yd.
  • the analysis of the organic components of the samples A and B was performed using gas chromatography equipped with a FID detector (manufactured by Agilent, model number 7890B), and the component ratio was determined based on the area ratio of each organic component in the chromatogram. ..
  • Table 1 shows the compositions of samples A and B.
  • Sample A contained octene added at the time of hydrogen fluoride as an additive, and the total amount of octene in sample A was 2.0% by weight.
  • concentration of octene in Sample B was low, 3.2 ppm by weight.
  • octene contains at least four kinds of isomers, and as shown in Table 1, these isomers were detected as Octene-1 to Octene-4. No individual octenes detected as Octene-4 from Octene-1 were identified.
  • samples A and B were subjected to water addition treatment and dehydration treatment, respectively.
  • the water addition treatment was performed by adding water to 30 g of sample A or B with a microsyringe.
  • the dehydration treatment was performed on sample A or B using a molecular sieve as a dehydrating agent.
  • samples A1 and A2 the samples obtained by adding water and dehydrating the sample A
  • samples B1 and B2 the samples obtained by adding water and dehydrating the sample B
  • the amount of water contained in these samples A1, A2, B1 and B2 was measured using a Karl Fischer titer.
  • Example 1 In this example, the results of a storage test in which samples A1, A2, B1 and B2 are sealed in a glass container will be described.
  • samples A1, A2, B1 and B2 were each injected into a glass vial (inner diameter of about 3.5 mm and length of about 6.5 cm), and the enclosed sample was allowed to stand at a temperature of 55 ° C. for 6 days under shading. .. The glass vial was then opened and the sample analyzed by ion chromatography. The analysis results are shown in Table 2.
  • the additive octene is contained at a concentration of 0.001% by weight to 0.1% by weight (that is, 10ppm to 1000ppm), which is the optimum concentration of the stabilizer disclosed in Patent Document 2. Nevertheless, the concentration of ions has increased significantly. Further, as disclosed in Patent Document 1, 1233yd is unstable with respect to water, and the water content is required to be less than 1000 ppm, preferably less than 100 ppm. However, in sample B1, although the water concentration satisfies this range, a significant increase in the ion concentration is observed. Therefore, this result is obtained under the conditions disclosed in Patent Documents 1 and 2. This means that the decomposition of 1233 yd cannot always be suppressed.
  • Japanese Patent Application Laid-Open No. 2016-216477 (hereinafter, reference) describes hydrofluorocarbons 2,3,3,3-tetrafluoropropene (hereinafter, 1234yf) and 1,3,3,3-tetrafluoropropene (hereinafter, reference). , 1234ze), the effect of adding water on stability in the presence of high oxygen concentrations is described. According to the description in this document, since the purification of 1234yf and 1234ze is performed by distillation, the deoxidizing treatment is not performed.
  • 1234yf and 1234ze contain a trace amount of oxygen, but 1234yf and 1234ze containing a trace amount of oxygen are stable, and the ionic component remains even if the mixture is allowed to stand at 150 ° C. for one week regardless of the addition of water. It is understood from this reference that it is not detected. This suggests that this reference teaches that water has no effect on the stability of hydrofluorocarbons and fluorochlorocarbons, which contain trace amounts of oxygen.
  • the results of this example are taken into consideration again, it is considered that the samples A1 to B2 contain a small amount of oxygen because none of the samples have been degassed or deoxidized such as nitrogen bubbling. Therefore, the result of this example means that when the oxygen concentration is low, the decomposition of 1233 yd can be suppressed by adding water. Considering the finding that 1233 yd rapidly decomposes in the presence of water, it is considered that the addition of water improves the stability of the composition containing 1233 yd, which is an unpredictable effect.
  • Example 2 As described above, it was confirmed that the addition of water suppressed the decomposition of 1233 yd.
  • octene is used as an additive, and the result of detailed examination of the concentration effect of the additive in the presence of water will be described.
  • Example 3 In this example, the result of storing the composition containing 1233 yd in a container containing stainless steel as a material will be described.

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Abstract

Un des modes de réalisation de la présente invention vise à fournir un procédé de stockage stable d'une composition contenant du 1-chloro-2,3,3-trifluoro-1-propène de façon stable, ou à fournir une composition qui contient du 1-chloro-2,3,3-trifluoro-1-propène et peut être stockée pendant une longue période. La composition comprend du 1-chloro-2,3,3-trifluoro-1-propène, un additif et de l'eau. La quantité d'eau peut être choisie dans une plage supérieure à 200 ppm en poids et inférieure ou égale à 1600 ppm en poids par rapport à la quantité de 1-chloro-2,3,3-trifluoro-1-propène. L'additif peut être un alcène non substitué.
PCT/JP2020/038751 2019-10-31 2020-10-14 Composition comprenant du 1-chloro-2,3,3-trifluoro-1-propène et de l'eau et procédé de stockage de cette composition WO2021085134A1 (fr)

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JP2019198987 2019-10-31
JP2019-198987 2019-10-31

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WO2021085134A1 true WO2021085134A1 (fr) 2021-05-06

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WO2022080073A1 (fr) * 2020-10-13 2022-04-21 株式会社モナテック Liquide de refroidissement de caloduc et caloduc plat de type plaque
CN114560750A (zh) * 2022-01-28 2022-05-31 浙江巨化技术中心有限公司 一种1-氯-2,3,3-三氟丙烯的制备方法

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WO2017018412A1 (fr) * 2015-07-27 2017-02-02 旭硝子株式会社 Procédé de production de 1-chloro-2,3,3-trifluoropropène
WO2017122801A1 (fr) * 2016-01-15 2017-07-20 旭硝子株式会社 Composition de solvant, procédé de nettoyage, procédé de formation d'un film de revêtement, milieu de transfert de chaleur et système de cycle thermique
WO2018092780A1 (fr) * 2016-11-15 2018-05-24 旭硝子株式会社 Procédé de fabrication de １－chloro－２，３，３－trifluoropropène

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JP2016216477A (ja) * 2014-09-26 2016-12-22 ダイキン工業株式会社 ハロオレフィン類の安定化方法
WO2017018412A1 (fr) * 2015-07-27 2017-02-02 旭硝子株式会社 Procédé de production de 1-chloro-2,3,3-trifluoropropène
WO2017122801A1 (fr) * 2016-01-15 2017-07-20 旭硝子株式会社 Composition de solvant, procédé de nettoyage, procédé de formation d'un film de revêtement, milieu de transfert de chaleur et système de cycle thermique
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Publication number Priority date Publication date Assignee Title
WO2022080073A1 (fr) * 2020-10-13 2022-04-21 株式会社モナテック Liquide de refroidissement de caloduc et caloduc plat de type plaque
CN114560750A (zh) * 2022-01-28 2022-05-31 浙江巨化技术中心有限公司 一种1-氯-2,3,3-三氟丙烯的制备方法

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