WO2010029704A1 - Huile pour réfrigérateur pour un réfrigérant 2,3,3,3-tétrafluoro-1-propène - Google Patents

Huile pour réfrigérateur pour un réfrigérant 2,3,3,3-tétrafluoro-1-propène Download PDF

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WO2010029704A1
WO2010029704A1 PCT/JP2009/004287 JP2009004287W WO2010029704A1 WO 2010029704 A1 WO2010029704 A1 WO 2010029704A1 JP 2009004287 W JP2009004287 W JP 2009004287W WO 2010029704 A1 WO2010029704 A1 WO 2010029704A1
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refrigerant
acid
ester
tetrafluoro
propene
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PCT/JP2009/004287
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English (en)
Japanese (ja)
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開米貴
高橋仁
松本朋也
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株式会社ジャパンエナジー
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Priority to JP2010528611A priority Critical patent/JP5597539B2/ja
Publication of WO2010029704A1 publication Critical patent/WO2010029704A1/fr

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    • 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
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/008—Lubricant compositions compatible with refrigerants
    • 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
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/12—Hydrocarbons
    • C09K2205/126—Unsaturated fluorinated hydrocarbons
    • 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
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/24—Only one single fluoro component present
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/042—Epoxides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C10M2209/1045—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C10M2209/1055—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086—Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/013—Iodine value
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/09—Characteristics associated with water
    • C10N2020/097—Refrigerants
    • C10N2020/101—Containing Hydrofluorocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants

Definitions

  • the present invention relates to a refrigerating machine oil using 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf, CH 2 ⁇ CF—CF 3 ) having a low global warming potential as a refrigerant.
  • chlorofluorocarbon containing fluorine and chlorine as constituent elements, such as R-11 (trichloromonofluoromethane), R-12 (dichlorodifluoromethane), hydrochlorofluorocarbon R-22 (monochlorodifluoromethane), which is (HCFC)
  • R-11 trichloromonofluoromethane
  • R-12 diichlorodifluoromethane
  • hydrochlorofluorocarbon R-22 monoochlorodifluoromethane
  • HFC hydrofluorocarbon
  • HFO-1234yf 2,3,3,3-tetrafluoro-1-propene
  • This HFO-1234yf is used as a refrigerant in refrigeration systems with high cooling efficiency, such as car air conditioners, room air conditioners, industrial refrigerators, etc., cultivated with the above-mentioned CFC refrigerants. Therefore, the selection of refrigerating machine oil compatible with this refrigerant has been an issue.
  • Patent Documents 1 and 2 disclose polyol esters, polyalkylene glycols, and esterified polyalkylene glycols that are usually used for hydrofluorocarbon (HFC) refrigerants even when fluorinated alkenes (fluorinated olefins) are used as refrigerants. It is disclosed that lubricants such as the like can be used. However, compatibility, solubility, lubricity in the mixed refrigerant state, etc., which are essential performances for refrigerating machine oil, vary depending on the type of refrigerant, so just because it was good with an HFC refrigerant that is a fluorinated alkane, as it is.
  • HFC hydrofluorocarbon
  • the fluorinated alkene HFO-1234yf can be used favorably.
  • the refrigerant is an olefin having a double bond
  • the stability of the mixed fluid of the refrigerant and the lubricant becomes a problem. That is, the lubricant suitable for the refrigerant HFO-1234yf can be understood by evaluating the performance as described above, and it has not been done yet, and an appropriate refrigerating machine oil has not been proposed yet.
  • the present invention solves the above-mentioned problems, has moderate compatibility and solubility with respect to the refrigerant HFO-1234yf, can maintain a viscosity that does not impair lubricity, and can reduce the amount of refrigerant charged. At the same time, it is to provide a refrigerating machine oil having excellent stability and lubricity.
  • the limited ester has moderate compatibility and solubility in the refrigerant HFO-1234yf, as well as high stability and low hygroscopicity. It has been found that it has good lubricity and is excellent as a refrigerating machine oil for the refrigerant HFO-1234yf.
  • the refrigerating machine oil for refrigerant HFO-1234yf of the present invention is one or more selected from neopentyl glycol, trimethylolpropane, pentaerythritol, or dipentaerythritol neopentyl polyol and linear or branched having 7 to 9 carbon atoms.
  • the monovalent fatty acid is 2-ethylhexanoic acid and / or 3,5,5-trimethylhexanoic acid
  • the neopentyl polyol is pentaerythritol and / or dipentaerythritol. is there.
  • the refrigerating machine oil for refrigerant HFO-1234yf of the present invention is preferably added with 0.05 to 3% by weight of one or more of hindered phenol compounds, amine compounds, epoxy compounds and carbodiimides, More preferably, an epoxy compound and a carbodiimide are added as essential components and added in an amount of 0.05 to 3% by weight.
  • the refrigerating machine oil of the present invention has moderate compatibility and solubility with respect to the refrigerant HFO-1234yf, and also has high electrical insulation, low moisture absorption, good lubricity, and high thermal oxidation stability. Excellent overall performance as refrigeration oil.
  • At least one neopentyl polyol selected from neopentyl glycol, trimethylolpropane, pentaerythritol, or dipentaerythritol is used.
  • Neopentyl polyol having more than 10 carbon atoms has an excessively large hydrocarbon portion, and the ester synthesized therefrom has low compatibility and solubility with the refrigerant HFO-1234yf and cannot achieve the object of the present invention. .
  • neopentyl polyol having compatibility with the refrigerant HFO-1234yf and capable of synthesizing a highly viscous ester
  • pentaerythritol and dipentaerythritol are particularly preferable.
  • n-heptanoic acid, n-octanoic acid, or n-nonanoic acid is used as the linear monovalent fatty acid having 7 to 9 carbon atoms
  • the straight chain monovalent fatty acid is used as the branched monovalent fatty acid.
  • All structural isomers of chain acids are included, but in order to obtain moderate compatibility, solubility and optimum lubricity, branched monovalent fatty acids and saturated monovalent fatty acids, especially 2 It is preferred to use ethylhexanoic acid, 3,5,5-trimethylhexanoic acid or mixtures thereof.
  • Fatty acids having 6 or less carbon atoms or 10 or more carbon atoms may be contained, but the proportion of all monovalent fatty acids is preferably 10 mol% or less, particularly preferably 5 mol% or less. Although a linear fatty acid may be included, the proportion of the monovalent fatty acid in the whole monovalent fatty acid is preferably 20 mol% or less, particularly preferably 10 mol% or less.
  • esters one obtained by esterifying one kind of the above neopentyl polyol and one kind of linear or branched monovalent fatty acid (ester compound) is used as it is or by mixing a plurality of different kinds of esters (ester mixture).
  • the ester used in the present invention is an esterification reaction by dehydration reaction between the specific neopentyl polyol and the specific fatty acid, or a general esterification reaction via an acid anhydride, acid chloride or the like which is a derivative of a fatty acid. Or by transesterification of each derivative.
  • coolant HFO-1234yf of this invention has a low global warming potential, since there exists a double bond in a molecule
  • degree of unsaturation of the ester may as low iodine value of the refrigerating machine oil to be the index is less 10gI 2 / 100g.
  • the ester obtained by the above method does not particularly limit the unreacted remaining acid and hydroxyl group, but preferably no carboxyl group or hydroxyl group remains. If the residual amount of carboxyl groups is large, undesired phenomena such as the formation of metal soap and precipitation due to the reaction with the metal used in the refrigerator occur, so the acid value of the refrigerator oil is 0.1 mgKOH / g or less. Further, if the residual amount of hydroxyl group is large, the ester becomes cloudy at a low temperature and undesired phenomena such as blocking of the capillary device of the refrigeration cycle occur. The following are more preferable.
  • the refrigerating machine oil of the present invention has a kinematic viscosity at 40 ° C. of 5 to 300 mm 2 / s in order to properly operate the refrigerating machine and ensure high efficiency.
  • This kinematic viscosity is preferably 7 to 250 mm 2 / s, more preferably 32 to 200 mm 2 / s.
  • the refrigerating machine oil of the present invention containing the above ester as a main component is a refrigerating machine oil for refrigerant HFO-1234yf, and exhibits appropriate compatibility and solubility in a wide range from low temperature to high temperature. Stability can be greatly improved. Furthermore, compared with polyalkylene glycol (PAG) and the like used as a substitute refrigeration oil for CFCs, the compatibility range with HFO-1234yf is much wider, the electrical insulation is high, and the hygroscopicity is low.
  • PAG polyalkylene glycol
  • the proportion of the ester as the main component in the refrigerating machine oil is preferably 50% by weight or more, particularly preferably 80% by weight or more, and more preferably 90% by weight or more.
  • the refrigerating machine oil according to the present invention includes a refrigerating machine oil. As long as the above function is satisfied, other types of esters, ethers such as PAG and PVE, or hydrocarbons such as alkylbenzene and mineral oil can be mixed as appropriate.
  • HFO-1234yf which is a refrigerant with a low global warming potential, has a double bond, so it is easily decomposed and its stability is not so high. Therefore, in order to increase the stability of the fluid mixture of the refrigerant and the refrigerating machine oil, a stability improving additive may be added.
  • the stability improving additive one or more of hindered phenol compounds, aromatic amine compounds, epoxy compounds, or carbodiimides may be added, and more preferably, the epoxy compound and carbodiimide are added together. It is sufficient to add a total of 0.05 to 3% by weight of these stability improvers to the refrigerating machine oil. In particular, it is preferable to blend both an epoxy compound and a carbodiimide.
  • hindered phenol compounds examples include 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-P-cresol, 4,4-methylene-bis- (2,6-di-tert-butyl- A tertiary alkyl-substituted phenolic compound such as P-cresol) is typically used.
  • the aromatic amine compound examples include ⁇ -naphthylamine, p, p′-di-octyl-diphenylamine, and the like. These compounds may be used alone or in combination of two or more, and are preferably contained in an amount of 0.05 to 2% by weight, particularly 0.1 to 1% by weight.
  • the epoxy compound is a compound having an epoxy group and preferably has 4 to 60 carbon atoms, particularly 5 to 25 carbon atoms.
  • the epoxy compound may be used alone or in combination of two or more, and is preferably contained in an amount of 0.01 to 2% by weight, particularly 0.02 to 1% by weight.
  • glycidyl ethers such as butyl glycidyl ether, 2-ethylhexyl glycidyl ether, trimethylolpropane polyglycidyl ether, neopentyl glycol diglycidyl ether, t-butylphenyl glycidyl ether, adipic acid glycidyl ester, 2-ethylhexane
  • glycidyl esters such as acid glycidyl ester, isononanoic acid glycidyl ester, and neodecanoic acid glycidyl ester, epoxidized fatty acid monoesters such as epoxidized methyl stearate, and epoxidized vegetable oils such as epoxidized soybean oil.
  • Preferable epoxy compounds are glycidyl ethers represented by the following general formulas 1 and 2 or glycidyl esters represented by
  • R 1 represents a hydrogen atom, a linear or branched alkyl group having 1 to 24 carbon atoms, or an alkylphenyl group having 1 to 24 carbon atoms.
  • R 2 represents a linear or branched alkylene group having 1 to 18 carbon atoms.
  • R 3 represents a linear or branched alkyl group having 1 to 24 carbon atoms or an alkylphenyl group having 1 to 24 carbon atoms.
  • the carbodiimide is represented by a general formula of R′—N ⁇ C ⁇ N—R ′′.
  • R ′ and R ′′ are hydrocarbon groups or hydrocarbon groups containing nitrogen and oxygen, which may be the same or different. May be. These hydrocarbon groups preferably contain a benzene ring, and diphenylcarbodiimide, di (alkylphenyl) carbodiimide or bis (alkylphenyl) carbodiimide is preferably used.
  • the carbodiimide may be used alone or in combination of two or more kinds, and is preferably contained in an amount of 0.01 to 1% by weight, particularly 0.05 to 0.5% by weight.
  • bis (alkylphenyl) carbodiimides include ditolylcarbodiimide, bis (isopropylphenyl) carbodiimide, bis (diisopropylphenyl) carbodiimide, bis (triisopropylphenyl) carbodiimide, bis (butylphenyl) carbodiimide, bis (dibutylphenyl) Examples thereof include carbodiimide and bis (nonylphenyl) carbodiimide.
  • anti-foaming agents such as phosphate esters and organic sulfur compounds used in refrigerating machine oils, oily agents such as alcohols and higher fatty acids, metal deactivators such as benzotriazole derivatives, and silicone oils. Additives such as agents can be added as appropriate.
  • Test oil of Example Sample oil of Example 1: ester of neopentyl glycol (NPG) and 2-ethylhexanoic acid (2EH) (2) Sample oil of Example 2: Trimethylolpropane (TMP) and 3,5,5 -Ester with trimethylhexanoic acid (3,5,5TH) (3) Test oil of Example 3: Ester of pentaerythritol (PE) and 2-ethylhexanoic acid (4) Test oil of Example 4: Di-tert.-butyl-, which is a hindered phenol compound as an additive to esters of pentaerythritol and 2-ethylhexanoic acid / 3,5,5-trimethylhexanoic acid with a mixed acid having a molar ratio of 1/1.
  • Test oil of Example 5 ester of pentaerythritol and 3,5,5-trimethylhexanoic acid, aromatic amine compound as additive is there Oil containing 0.3% by weight of dioctyl-diphenylamine (DODA) and 0.5% by weight of 2-ethylhexyl glycidyl ether (2-EHGE) as an epoxy compound (6)
  • Test oil of Example 6 pentaerythritol / Oil obtained by adding 0.1% by weight of diphenylcarbodiimide (DPCI) as an additive to an ester of a mixed alcohol having a molar ratio of dipentaerythritol (D-PE) of 1/1 and 3,5,5-trimethylhexanoic acid (7)
  • Test oil of Example 7 an ester of dipentaerythritol and 2-ethylhexanoic acid / 3,5,5-trimethylhexanoic acid mixed
  • Sample oil of Comparative Example 1 ester of trimethylolpropane and oleic acid (OA)
  • Sample oil of Comparative Example 2 ester of pentaerythritol and oleic acid, di-tert Oil containing 0.3% by weight of butyl-p-cresol, 0.5% by weight of 2-ethylhexyl glycidyl ether and 0.1% by weight of diphenylcarbodiimide (11)
  • Test oil of Comparative Example 3 Pentaerythritol And an ester of i-pentanoic acid / n-pentanoic acid / n-heptanoic acid / n-octylic acid with a mixed acid having a molar ratio of 1/3/2/4
  • Test oil of Comparative Example 4 Polyalkylene Glycol (PAG, terminal is butyl group and hydroxyl group, skeleton is oxypropylene, average molecular weight is
  • the properties of each sample oil are shown in Table 1.
  • the kinematic viscosity was measured according to JIS K2283, the iodine value was measured according to JIS K0070, and the total acid value and hydroxyl value were measured according to JIS K2501.
  • the volume resistivity at 80 ° C. was determined based on JIS C2101. (Hygroscopic) A 100 ml beaker was charged with 60 g of sample oil and allowed to stand for 3 hours in an open atmosphere at a temperature of 25 ° C. and a humidity of 70%, and the moisture concentration was measured by the Karl Fischer method.
  • the ester according to the present invention is compatible with the refrigerant HFO-1234yf in a wide temperature range, and has good characteristics as a refrigerating machine oil including thermal stability.
  • Examples 4 to 8 in which additives were added had little increase in the total acid value after the thermal stability test, and in Examples 7 and 8 in which both the epoxy compound and carbodiimide were added, there was no increase in the total acid value. It was.
  • the esters of Comparative Examples 1 and 2 if the carbon number of the acid is too large, it will not be compatible with HFO-1234yf, and if the iodine value is high, the thermal stability will be extremely poor, and there will be a significant improvement due to the additive.
  • the refrigerating machine oil of the present invention is used as a lubricating oil for a refrigerating machine that uses HFO-1234yf as a refrigerant, and in particular, a compressor, a condenser, a throttle device (a refrigerant flow control unit such as an expansion valve or a capillary tube), an evaporator.
  • a compressor a condenser
  • a throttle device a refrigerant flow control unit such as an expansion valve or a capillary tube
  • evaporator evaporator
  • Etc., and refrigeration systems with high cooling efficiency that circulate refrigerant between them especially in refrigerators having compressors such as swash plate type, reciprocating type, rotary type, scroll type compressor, etc. It can be used as oil and can be suitably used for car air conditioners, room air conditioners, industrial refrigerators and the like.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
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  • General Chemical & Material Sciences (AREA)
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  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Lubricants (AREA)

Abstract

La présente invention concerne une huile pour réfrigérateur qui a une compatibilité propre avec un réfrigérant 2,3,3,3-tétrafluoro-1-propène et une solubilité propre dans le réfrigérant 2,3,3,3-tétrafluoro-1-propène, qui peut garder sa viscosité à un niveau tel que la lubrification n’est pas détériorée, qui permet la diminution de la quantité d’un réfrigérant à charger dans un réfrigérateur et présente d’excellentes propriétés de stabilité, pouvoir lubrifiant et équivalents. L’invention concerne spécifiquement une huile pour réfrigérateur pour un réfrigérant 2,3,3,3-tétrafluoro-1-propène, qui comprend un ester d’au moins un composant choisi parmi le néopentyl glycol, le triméthylol propane, le pentaérythritol et le dipentaérythritol et au moins un composant choisi parmi des acides gras monovalents ayant chacun 7 à 9 atomes de carbone comme ingrédient principal, et a une viscosité cinématique de 5 à 300 mm2/s à 40 ˚C, un indice d’iode inférieur ou égal à 10 g d’I2/100 g et un indice d’acidité totale inférieur ou égal à 0,1 mg de KOH/g.
PCT/JP2009/004287 2008-09-09 2009-09-01 Huile pour réfrigérateur pour un réfrigérant 2,3,3,3-tétrafluoro-1-propène WO2010029704A1 (fr)

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JP2011052032A (ja) * 2009-08-31 2011-03-17 Hitachi Appliances Inc ２，３，３，３−テトラフルオロプロペンを用いた冷凍空調装置
JP2011094039A (ja) * 2009-10-30 2011-05-12 Hitachi Appliances Inc 冷媒圧縮機，冷凍サイクル装置
FR2962130A1 (fr) * 2010-06-30 2012-01-06 Arkema France Composition a base de 2,3,3,3-tetrafluoropropene
US20120132848A1 (en) * 2010-11-30 2012-05-31 Jx Nippon Oil & Energy Corporation Working fluid composition for refrigerator machine and refrigerating machine oil
WO2013115296A1 (fr) * 2012-02-01 2013-08-08 Ｋｈネオケム株式会社 Ester mixte
WO2015050120A1 (fr) * 2013-10-02 2015-04-09 Ｊｘ日鉱日石エネルギー株式会社 Composition d'huile pour machine frigorifique et machine frigorifique
JPWO2013115160A1 (ja) * 2012-02-01 2015-05-11 Ｋｈネオケム株式会社 混合多価アルコールとカルボン酸との混合エステル
JP2015140391A (ja) * 2014-01-28 2015-08-03 Ｊｘ日鉱日石エネルギー株式会社 冷凍機用作動流体組成物及び冷凍機油
JPWO2013141008A1 (ja) * 2012-03-23 2015-08-03 Ｋｈネオケム株式会社 混合エステル
WO2015125883A1 (fr) * 2014-02-20 2015-08-27 旭硝子株式会社 Composition pour système à cycle thermodynamique, et système à cycle thermodynamique
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JP2011094039A (ja) * 2009-10-30 2011-05-12 Hitachi Appliances Inc 冷媒圧縮機，冷凍サイクル装置
EP3202870A1 (fr) * 2010-06-30 2017-08-09 Arkema France Utilisation d'une composition a base de 2,3,3,3-tetrafluoropropene
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