EP0989179A1 - Huile pour machine réfrigérante - Google Patents

Huile pour machine réfrigérante Download PDF

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Publication number
EP0989179A1
EP0989179A1 EP99850137A EP99850137A EP0989179A1 EP 0989179 A1 EP0989179 A1 EP 0989179A1 EP 99850137 A EP99850137 A EP 99850137A EP 99850137 A EP99850137 A EP 99850137A EP 0989179 A1 EP0989179 A1 EP 0989179A1
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EP
European Patent Office
Prior art keywords
refrigerating machine
oil
mass
isomers
hfc
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99850137A
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German (de)
English (en)
Inventor
Hiroyuki c/o Nippon Mitsubishi Oil Corp. Hirano
Yuji c/o Nippon Mitsubishi Oil Corp. Shimomura
Satoshi c/o Nippon Mitsubishi Oil Corp. Suda
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eneos Corp
Original Assignee
Nippon Mitsubishi Oil Corp
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Filing date
Publication date
Application filed by Nippon Mitsubishi Oil Corp filed Critical Nippon Mitsubishi Oil Corp
Publication of EP0989179A1 publication Critical patent/EP0989179A1/fr
Withdrawn legal-status Critical Current

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    • 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
    • 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
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02—Petroleum fractions
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02—Well-defined hydrocarbons
    • C10M105/06—Well-defined hydrocarbons aromatic
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/10—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing aliphatic monomer having more than 4 carbon atoms
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/16—Ethers
    • C10M129/18—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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/08—Ammonium or amine salts
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    • 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
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    • C10M2203/06—Well-defined aromatic compounds
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    • C10M2203/065—Well-defined aromatic compounds used as base material
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    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • C10M2203/1045—Aromatic fractions used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • C10M2203/1065—Naphthenic fractions used as base material
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    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C10M2203/1085—Residual fractions, e.g. bright stocks used as base material
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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    • 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
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    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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    • C10M2207/042—Epoxides
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    • C10M2223/04—Phosphate esters
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    • C10M2223/041—Triaryl phosphates
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    • C10N2040/30—Refrigerators lubricants or compressors lubricants
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    • C10N2040/42—Flashing oils or marking oils
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    • C10N2040/50—Medical uses

Definitions

  • This invention relates to refrigerating machine oils, and more particularly to refrigerating machine oils for refrigerating machines using dimethyl ether (DME) as a refrigerant.
  • DME dimethyl ether
  • an object of the present invention is to provide a refrigerating machine oil which can be used with a DME refrigerant and has excellent lubricity, miscibility with the refrigerant and safety.
  • a refrigerating machine oil containing a hydrocarbon oil for a refrigerating machine using a DME refrigerant.
  • Eligible hydrocarbon oils for the inventive refrigerating machine oil may be naphthenic- or paraffinic mineral oils, olefin polymers, naphthalene compounds, alkylbenzene oils and mixtures thereof.
  • mineral oils are paraffinic- or naphthenic-mineral oils produced by subjecting the refrigerating machine oil fraction resulting from the atmospheric or vacuum distillation of a paraffinic- or naphthenic- crude oil or an intermediate base crude oil to one or more than two of refining processes such as solvent deasphalting, solvent extraction, hydrocracking, solvent dewaxing, catalytic dewaxing, hydrofinishing, sulfuric acid washing or clay treatment.
  • the highly refined mineral oils used for the present invention preferably contain unsaturates (degree of unsaturation) in non-aromatics of less than 10 percent. Unsaturates greater than 10 percent would cause the formation of sludge and the clogging of capillaries. Therefore, in the present invention, the unsaturation degree should be preferably less than 5 percent, more preferably less than 1 percent and most preferably 0.1 percent.
  • Such highly refined mineral oils are refined oils obtained by refining the distillate resulting from the atmospheric distillation of a paraffinic- or naphthenic- crude oil or an intermediate base crude oil or the distillate resulting from the vacuum distillation of the residue obtained by this atmospheric distillation, in accordance with a conventional manner; deep-dewaxed oils obtained by further deep-dewaxing the refined oils; and hydrogenated oils obtained by further hydrogenating the refined oils. No particular limitation is imposed on the refining process upon the production of these mineral oils.
  • the refining process may be conducted as follows:
  • Preferred highly refined minerals obtained by the above processes are naphthenic mineral oils and mineral oils obtained by the deep-dewaxing process because of fluidity at low temperatures and no wax precipitation at low temperatures.
  • the deep-dewaxing process may be conducted by solvent dewaxing under sever conditions or by catalytic dewaxing using a zeolite catalyst.
  • the olefin polymers may be those obtained by polymerizing an olefin having 2 to 12 carbon atoms, and the products obtained by hydrogenating the polymerized olefin.
  • Specific examples of such olefin polymers are polybutene, polyisobutene, the oligomers of ⁇ -olefin (poly- ⁇ -olefin) having 5 to 12 carbon atoms, ethylene-propylene copolymer, and the hydrogenates thereof.
  • the olefin polymers can be produced by any suitable conventional methods.
  • a poly- ⁇ -olefin may be produced by employing the conventional polymerization processes such as a Ziegler catalysis process, a radical polymerization process, an aluminum chloride process and a boron fluoride process wherein an ⁇ -olefin derived from ethylene is used as a raw material.
  • naphthalene compounds No particular limitation is imposed on the naphthalene compounds as long as they have naphthalene skeleton, but preferred are compounds represented by the following formula because of their excellent miscibility with a DME refrigerant; wherein R 1 , R 2 , R 3 and R 4 may be the same or different and are each independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, provided that the total number of carbon atoms of R 1 through R 4 is within a range of 1 to 10.
  • R 1 , R 2 , R 3 and R 4 may be the same or different and are each independently a hydrogen atom or a hydrocarbon group having 1 to 10, preferably 1 to 8 carbon atoms.
  • the hydrocarbon group may be an alkyl, alkenyl, aryl, alkylaryl or aralkyl group.
  • Preferred hydrocarbon groups for R 1 , R 2 , R 3 and R 4 include a C 1 - C 8 alkyl group such as methyl, ethyl, n-propyl, isopropyl, straight or branched butyl, straight or branched pentyl, straight or branched hexyl, straight or branched heptyl and straight or branched octyl; a C 2 - C 8 alkenyl group such as ethenyl (vinyl), 1-propenyl, 2-propenyl (allyl), 1-methylethenyl (isopropenyl), straight or branched butenyl, straight or branched pentenyl, straight or branched hexenyl, straight or branched heptenyl and straight or branched octenyl; a C 6 - C 8 aryl or alkylaryl group such as phenyl, tolyl, xylyl
  • a total number of carbon atoms of R 1 , R 2 , R 3 and R 4 in Formula (1) should be in the range of 1 to 10, preferably 1 to 8. If the total number of carbon atoms is within this range, then R 1 , R 2 , R 3 and R 4 may be the same or different. In other words, all of R 1 , R 2 , R 3 and R 4 may be a hydrocarbon group, or at least one of R 1 , R 2 , R 3 and R 4 may be a hydrocarbon group while the rest thereof may be a hydrogen atom.
  • R 1 , R 2 , R 3 and R 4 are a hydrocarbon group while the rest thereof are a hydrogen atom and that the total number of carbon atoms of R 1 , R 2 , R 3 and R 4 is within the range of 3 to 8.
  • R 1 , R 2 , R 3 and R 4 are each a hydrocarbon group
  • the combination thereof is not particularly restricted.
  • a pair of hydrocarbon groups may be attached to the same condensed ring (a benzene ring) as in the case where R 1 and R 2 are each hydrocarbon groups.
  • a single hydrocarbon group may be attached to each of different condensed rings (benzene rings) as in the case where R 1 and R 3 are each hydrocarbon groups.
  • Preferred naphthalene compounds of Formula (1) include (n-propyl) naphthalene, isopropylnaphthalene, (n-butyl) naphthalene, isobutylnaphthalene, (sec-butyl) naphthalene, (tert-butyl) naphthalene, (sec-pentyl) naphthalene, (1-ethylpropyl) naphthalene, (tart-pentyl) naphthalene, (1-methylpentyl) naphthalene, (1-ethylbutyl) naphthalene, (1,1-dimethylbutyl) naphthalene, (1-ethyl-1-methylpropyl) naphthalene, (1-methylhexyl) naphthalene, (1-ethylpentyl) naphthalene, (1-propylbutyl) n
  • the naphthalene compounds may be compounds having a single structure or may be a mixture of compounds having different structures as long as these compounds are each represented by Formula (1).
  • naphthalene compounds No particular limitation is imposed on the production method of the naphthalene compounds and thus any of suitable conventional methods can be used. For instance, they can be obtained by attaching (or addition of reacting) compounds selected from the group consisting of halides of hydrocarbon compounds having 1 to 10 carbon atoms, olefins having 2 to 10 carbon atoms and styrenes having 8 to 10 carbon atoms to naphthalene in the presence of a mineral acid such as sulfuric acid, phosphoric acid, silicotungstic acid or hydrofluoric acid; a solid acidic substance such as acid clay or activated clay; or a Friedel-Crafts catalyst which is a metal halide such as aluminum chloride or zinc chloride.
  • a mineral acid such as sulfuric acid, phosphoric acid, silicotungstic acid or hydrofluoric acid
  • a solid acidic substance such as acid clay or activated clay
  • a Friedel-Crafts catalyst which is a metal hal
  • alkylbenzene oils are eligible for the purpose of the present invention, but it is preferred to use the alkylbenzene oils containing more than 60 mass percent, preferably more than 65 mass percent, more preferably more than 70 mass percent, further more preferably more than 80 mass percent, most preferably 100 mass percent of alkylbenzene components having a molecular weight of 200 to 350 in view of little possibility of the occurrence of seizure of a refrigerating compressor during a long period of its operation.
  • the alkylbenzene oils may desirably contain preferably more than 30 mass percent, more preferably more than 35 mass percent, most preferably more than 40 mass percent of alkylbenzene components having a molecular weight of 200 to 300.
  • alkylbenzene oil (hereinafter referred to as an alkylbenzene oil (A)) composed of alkylbenzenes having 1 to 4 alkyl groups each having 1 to 19 carbon atoms, the total number of carbon atoms of these alkyl groups being 9 to 19. It is more preferred to use alkylbenzenes having 1 to 4 alkyl groups having each 1 to 15 carbon atoms, the total number of carbon atoms in the alkyl groups being 9 to 15
  • alkyl groups having 1 to 19 carbon atoms are methyl, ethyl, propyl (including all isomers), butyl (including all isomers), pentyl (including all isomers), hexyl (including all isomers), heptyl (including all isomers), octyl (including all isomers), nonyl (including all isomers), decyl (including all isomers), undecyl (induding al isomers), dodecyl (including all isomers), tridecyl (including all isomers), tetradecyl (including all isomers), pentadecyl (including all isomers), hexadecyl (induding all isomers), heptadecyl (including all isomers), octadecyl (induding all isomers) and nonadecyl (induding all isomers).
  • alkyl groups may be of straight chain or branched chain. However, in view of the stability and viscosity characteristics, branched alkyl groups are preferred. Furthermore, in view of availability, more preferred are branched alkyl groups derived from oligomers of olefins such as propylene, butene and isobutylene.
  • alkylbenzene oils (A) The number of alkyl groups in the alkylbenzene oils (A) is confined to 1 to 4. However, in view of the stability and availability, it is the most preferred to use alkylbenzenes having one or two alkyl groups, such as a monoalkylbenzene, a dialkylbenzene or a mixture thereof.
  • the alkylbenzenes (A) may be not only those having the same molecular structure, but also a mixture of those having different molecular structures as long as they satisfy the conditions that they contain 1 to 4 alkyl groups each having 1 to 19 carbon atoms, the total number thereof being 9 to 19.
  • the alkylbenzene oils used for the present invention may preferably contain less than 40 mass percent, preferably less than 35 mass percent, more preferably less than 30 mass percent, of the alkylbenzenes having a molecular weight of less than 200 or more than 350.
  • the molecular weight of such alkylbenzenes be confined to a range of more than 350 to 450, preferably 350 to 430.
  • alkylbenzenes having a molecular weight of less than 200 or more than 350 as long as their molecular weight falls within this range.
  • preferred alkylbenzenes are those having 1 to 4 alkyl groups having each 1 to 40 carbon atoms, the total number of carbon atoms in the alkyl groups being 20 to 40 (hereinafter referred to as alkylbenzenes (B)), and more preferred are those having 1 to 4 alkyl groups having each 1 to 30 carbon atoms, the total number of thereof being 20 to 30.
  • alkyl groups having 1 to 40 carbon atoms are methyl, ethyl, propyl (including all isomers), butyl (including all isomers), pentyl (including all isomers), hexyl (including all isomers), heptyl (induding all isomers),octyl (including all isomers), nonyl (including all isomers), decyl (including all isomers), undecyl (including al isomers), dodecyl (including all isomers), tridecyl (including all isomers), tetradecyl (including all isomers), pentadecyl (induding all isomers), hexadecyl (including all isomers), heptadecyl (including all isomers), octadecyl (including all isomers), nonadecyl (induding all isomers), icosyl (including all isomers), hene
  • alkyl groups may be of straight chain or branched chain. However, in view of the stability and viscosity characteristics, branched alkyl groups are preferred. Furthermore, in view of availability, more preferred are branched alkyl groups derived from oligomers of olefins such as propylene, butene and isobutylene.
  • alkylbenzene oils (B) The number of alkyl groups in the alkylbenzene oils (B) is confined to 1 to 4. However, in view of the stability and availability, it is the most preferred to use alkylbenzenes having one or two alkyl groups, such as a monoalkylbenzene, a dialkylbenzene or a mixture thereof.
  • the alkylbenzenes (B) may be not only those having the same molecular structure, but also a mixture of those having different molecular structures as long as they satisfy the conditions that they contain 1 to 4 alkyl groups each having 1 to 40 carbon atoms, the total number thereof being 20 to 40.
  • alkylbenzenes can be produced by any suitable method such as the following synthesizing method.
  • Eligible aromatic compounds as a raw material include benzene, toluene, xylene, ethylbenzene, methylethylbenzene, diethylbenzene and a mixture thereof.
  • Eligible alkylating agents include a straight or branched olefin obtained by polymerizing a lower-olefin having 6 to 40 carbon atoms, such as ethylene, propylene, butene and isobutylene, among which propylene is preferred or obtained by thermally decomposing wax, heavy oils, a petroleum fraction, polyethylene and polypropylene; a straight olefin having 9 to 40 carbon atoms obtained by separating n-paraffin from a petroleum fraction such as kerosene or gas oil and then catalytically transforming the n-paraffin into an olefin; and a mixture thereof.
  • An alkylating catalyst used for the alkylation may be a conventional catalyst exemplified by a Friedel-Crafts catalyst such as aluminum chloride and zinc chloride; and an acidic catalyst such as sulfuric acid, phosphoric acid, silicotungstic acid, hydrofluoric acid or activated clay.
  • a Friedel-Crafts catalyst such as aluminum chloride and zinc chloride
  • an acidic catalyst such as sulfuric acid, phosphoric acid, silicotungstic acid, hydrofluoric acid or activated clay.
  • the alkylbenzene oil may be obtained by mixing separately prepared alkylbenzenes having a molecular weight of 200 to 350 with alkylbenzenes having a molecular weight of less than 200 or more than 350 within a ratio as defined by the present invention.
  • inventive refrigerating machine oil may contain the hydrocarbon oil in an amount of preferably more than 50 mass percent, more preferably more than 70 mass percent, further more preferably more than 80 mass percent, most preferably more than 90 mass percent, based on the total mass of the refrigerating machine oil.
  • the refrigerating machine oil according to the present invention contains the above-mentioned hydrocarbon oil but in addition to this, may further contain an oxygen-containing synthetic oil such as an ester, polyglycol, polyvinyl ether, ketone, polyphenyl ether, silicone, polysiloxane and perfluoro ether.
  • an oxygen-containing synthetic oil such as an ester, polyglycol, polyvinyl ether, ketone, polyphenyl ether, silicone, polysiloxane and perfluoro ether.
  • oxygen-containing synthetic oils preferred are an ester, polyglycol, ketone, polyvinyl ether and a mixture thereof.
  • the refrigerating machine oil according to the present invention may contain the hydrocarbon oil alternatively with the oxygen-containing synthetic oil as a base oil.
  • the refrigerating machine oil of the present invention can be put in use without being incorporated with an additive.
  • the refrigerating machine oil may contain any of various additives as required.
  • the inventive refrigerating machine oil may be blended with at least one phosphorus compound selected from the group consisting of phosphoric esters, acidic phosphoric esters, amine salts of acidic phosphoric esters, chlorinated phosphoric esters and phosphorous esters.
  • phosphorus compounds are esters obtained by a reaction between phosphoric acid or phosphorous acid and an alkanol or polyether type alcohol, and are also derivatives of these esters.
  • phosphoric esters are tributyl phosphate, tripentyl phosphate, trihexyl phosphate, triheptyl phosphate, trioctyl phosphate, trinonyl phosphate, tridecyl phosphate, triundecyl phosphate, tridodecyl phosphate, tritridecyl phosphate, tritetradecyl phosphate, tripentradecyl phosphate, trihexadecyl phosphate, triheptadecyl phosphite, trioctadecyl phosphate, trioleyl phosphate, triphenyl phosphate, tricresyl phosphate, trixylyl phosphate, cresyldiphenyi phosphate and xylyldiphenyl phosphate.
  • acidic phosphoric esters are monobutyl acid phosphate, monopentyl acid phosphate, monohexyl acid phosphate, monoheptyl acid phosphate, monooctyl acid phosphate, monononyl acid phosphate, monodecyl acid phosphate, monoundecyl acid phosphate, monododecyl acid phosphate, monotridecyl acid phosphate, monotetradecyl acid phosphate, monopentadecyl acid phosphate, monohexadecyl acid phosphate, monoheptadecyl acid phosphate, monooctadecyl acid phospahte, monooleyl acid phosphate, dibutyl acid phosphate, dipentyl acid phospahte, dihexyl acid phospahte, diheptyl acid phospahte, dioctyl acid phosphate, dinonyl acid
  • amine salts of acidic phosphoric esters are methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, trimethylamine, triethylamine, tripropylamine, tributylamine, tripentylamine, trihexylamine, triheptylamine and trioctylamine of the acidic phosphoric ester.
  • chlorinated phosphoric esters are tris-dichloropropyl phosphate, tris-chloroethyl phosphate, tris-chlorophenyl phosphate and polyoxyalkylene bis[di(chloroalkyl)] phosphate.
  • phosphorous esters are dibutyl phosphite, dipentyl phosphite, dihexyl phosphite, diheptyl phosphite, dioctyl phosphite, dinonyl phosphite, didecyl phosphite, diundecyl phosphite, didodecyl phosphite, dioleyl phosphite, diphenyl phosphite, dicresyl phosphite, tributyl phosphite, tripentyl phosphite, trihexyl phosphite, triheptyl phosphite, trioctyl phophite, trinonyl phosphite, tridecyl phosphite, triundecyl phosphite, tridodecyl
  • these phosphorus compounds may be blended with the inventive refrigerating machine oil in any suitable ratio, their content may be within the range of 0.01 to 5.0 mass percent, preferably 0.02 to 3.0 mass percent, based on the total mass of the refrigerating machine oil (based on the total mass of the base oil and the Whole additives).
  • an epoxy compound selected from the group consisting of: (1) phenylglycidyl ether type epoxy compounds, (2) alkylglycidyl ether type compounds, (3) glycidyl ester type epoxy compounds, (4) aryl oxirane compounds, (5) alkyl oxirane compounds, (6) alicyclic epoxy compounds, (7) epoxidized fatty monoesters and (8) epoxidized vegetable oils.
  • phenylglycidyl ether type epoxy compounds (1) are phenylglycidyl ether and alkylphenylglycidyl ether.
  • the alkylphenylglycidyl ether may be those having 1 to 3 alkyl groups each having 1 to 13 carbon atoms, preferably those having one alky group having 4 to 10 carbon atoms.
  • alkylphenylglycidyl ethers are n-butylphenylglyddyl ether, i-butylphenylglycidyl ether, sec-butyl phenylglycidyl ether, tert-butyl phenylglycidyl ether, pentylphenylglycidyl ehter, hexylphenylglycidyl ether, heptylphenylglycidyl ehter, octylphenylglycidyl ether, nonylphenylglycidyl ehter and decylphenylglycidyl ehter.
  • alkylglycidyl ether type compounds (2) are decylglycidyl ether, undecylglycidyl ether, dodecylglycidyl ether, tridecylglycidyl ether, tetradecylglycidyl ether, 2-ethylhexylglycidyl ether, neopentylglycoldiglycidyl ether, trimethylolpropane triglycidyl ehter, pentaerythritol tetraglycidyl ether, 1,6-hexanediol diglycidyl ether, sorbitol polyglycidyl ether, polyalkyleneglycol monoglycidyl ether and polyalkyleneglycol diglycidyl ether.
  • glycidyl ester type epoxy compounds (3) are phenylglycidyl ester, alkylglycidyl ester and alkenylglycidyl ester. Preferred are glycidyl-2,2-dimethyloctanoate, glycidyl benzoate, glycidyl acrylate and glycidyl methacrylate.
  • aryl oxirane compounds (4) are 1,2-epoxystyrene and alkyl-1 ,2-epoxystyrene.
  • alkyl oxirane compounds (5) are 1,2-epoxybutane, 1,2-epoxypentane, 1,2-epoxyhexane, 1,2-epoxyheptane, 1,2-epoxyoctane, 1,2-epoxynonane, 1,2-epoxydecane, 1,2-epoxyundecane, 1,2-epoxydodecane, 1,2-epoxytridecane, 1,2-epoxytetradecane, 1,2-epoxypentadecane, 1,2-epoxyhexadecane, 1,2-epoxyheptadecane, 1,2-epoxyoctadecane, 1,2-epoxynonadecane and 1,2-epoxyeicosane.
  • alicydic epoxy compounds (6) are 1,2-epoxycyclohexane7 1,2-epoxycyclopentane, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, bis(3,4-epoxycyclohexylmetyl) adipate, exo-2,3-epoxynorbornane, bis(3,4-epoxy-6-methycyclohexylmetyl) adipate, 2-(7-oxabicyclo[4.1.0]hept-3-yl)-spiro(1,3-dioxane-5,3'-[7]oxabicyclo[4.1.0]) heptane, 4-(1'-metylepoxyethyl)-1,2-epoxy-2-methylcyclohexane and 4-epoxyethyl-1,2-epoxycyclohexane.
  • epoxidized fatty monoesters (7) are an ester formed by reacting an epoxidized fatty acid having 12 to 20 carbon atoms with an alcohol having 1 to 8 carbon atoms, phenol or alkylphenol.
  • Particularly preferred are epoxystearates such as butyl, hexyl, benzyl, cyclohexyl, methoxyethyl, phenyl and butylphenyl esters of epoxystearic acid.
  • epoxidized vegetable oils (8) epoxy compounds of vegetable oils such as soybean oil, linseed oil and cottonseed oil.
  • epoxy compounds preferred are phenylglycidyl ether type epoxy compounds, glycidyl ester type epoxy compounds, alicyclic epoxy compounds and epoxidized fatty monoesters. More preferred are phenylglycidyl ether type epoxy compounds and glycidyl ester type epoxy compounds. Particularly preferred are phenylglycidyl ether, butylphenylglycidyl ether, alkylglycidyl ester and mixtures thereof.
  • the inventive refrigerating machine oil may be blended with these epoxy compounds in any suitable blending ratio.
  • the epoxy compound is generally blended in an amount of 0.1 to 5.0 mass percent, preferably 0.2 to 2.0 mass percent, based on the total mass of the refrigerating machine oil (based on the total mass of the base oil and the whole additives).
  • each of the phosphorus compounds and the epoxy compounds may be used in combination.
  • the suitable additives may be anti-oxidants of a phenol type such as di-tett-butyl-p-cresol and bisphenol A or of an amide type such as phenyl- ⁇ -naphthyl amine and N,N-di(2-naphthyl)-p-phenylenediamine; anti-wear additives such as zinc dithiophosphate; extreme pressure agents such as chlorinated paraffin and sulfur compounds; oiliness improvers such as fatty acid; silicone-type antiforming agents; metal inactivators such as benzotriazole; viscosity index improvers; pour point depressants; and detergent-dispersants.
  • These additives may be added in an amount of less than 10 mass percent, preferably less than 5 mass percent, based on the total mass of the refrigerating machine oil (based on the total mass of the base oil and
  • the kinematic viscosity of the refrigerating machine oil of the present invention preferably has a kinematic viscosity at 40 °C of preferably 3 to 100 mm 2 /s, more preferably 4 to 50 mm 2 /s, most preferably 5 to 40 mm 2 /s and a kinematic viscosity at 100 °C of preferably 1 to 20 mm 2 /s, more preferably 2 to 10 mm 2 /s.
  • the refrigerating machine oil of the present invention preferably has a volume resistivity of greater than 1.0 x 10 12 ⁇ ⁇ cm, preferably greater than 1.0 x 10 13 ⁇ ⁇ cm, more preferably greater than 1.0 x 10 14 ⁇ ⁇ cm.
  • volume resistivity designates a value measured at a temperature of 40 °C in accordance with JIS C 2101 "Testing methods of electrical insulating oils".
  • the water content of the refrigerating machine oil of the present invention is not particularly restricted, but may be present within the range of preferably less than 200 ppm, more preferably less than 100 ppm, most preferably less than 50 ppm.
  • refrigerating machine oils are used in a sealed type refrigerating machine, less water contents are preferred in view of the stability and electric insulation of the oils.
  • the total acid value of the refrigerating machine oil of the present invention is not particularly restricted, but may be preferably less than 0.1 mgKOH/g, more preferably 0.05 mgKOH/g in order to prevent the corrosion of metals used in a refrigerating machine or pipes thereof.
  • the total acid value used herein designates a total acid value measured in accordance with JIS K 2501 "Petroleum products and lubricants-Determination of neutralization number".
  • the ash content of the refrigerating machine oil of the present invention is not particularly restricted, but may be preferably less than 100 ppm, more preferably 50 ppm.
  • the ash content used herein designates a value of ash content measured in accordance with JIS K 2272 "Testing Methods for Ash and Sulfated Ash of Crude Oil and Petroleum Products".
  • the refrigerant used in a refrigerating machine together with the refrigerating machine oil is dimethyl ether (DME) or alternatively a mixture of DME and other refrigerants such as hydrofluorocarbon, hydrocarbon, carbon dioxide and ammonia.
  • DME dimethyl ether
  • other refrigerants such as hydrofluorocarbon, hydrocarbon, carbon dioxide and ammonia.
  • the hydrofluorocarbon refrigerants may be hydrofluorocarbon having 1 to 3 carbon atoms, preferably 1 to 2 carbon atoms.
  • Specific examples of the hydrofluorocarbon refrigerants are difluoromethane (HFC-32), trifluoromethane (HFC-23), pentafluoroethane (HFC-125), 1,1,2,2-tetrafluoroethane (HFC-134), 1,1,1,2-tetrafluoroethane (HFC-134a), 1,1,1-trifluoroethane (HFC-143a), 1,1-difluoroethane (HFC-152a) and a mixture of at least two kinds of thereof.
  • refrigerants are HFC-32 alone; HFC-23 alone; HFC-134a alone; HFC-125 alone; a mixture of HFC-134a / HFC-32 in a ratio of 60-80 mass % / 40-20 mass %; a mixture of HFC-32 / HFC-125 in a ratio of 40-70 mass % / 60-30 mass %; a mixture of HFC-125 / HFC-143a in a ratio of 40-60 mass % / 60-40 mass %; a mixture of HFC-134a / HFC-32 / HFC-125 in a ratio of 60 mass % / 30 mass % / 10 mass %; a mixture of HFC-134a / HFC-32 / HFC-125 in a ratio of 40-70 mass % / 15-35 mass % / 5-40 mass % and a mixture of HFC-125 / HFC
  • the HFC refrigerant mixtures include a mixture of HFC-134a / HFC-32 in a ratio of 70 mass % / 30 mass %; a mixture of HFC-32 / HFC-125 in a ratio of 60 mass % / 40 mass %; a mixture of HFC-32 / HFC-125 in a ratio of 50 mass % / 50 mass % (R410A); a mixture of HFC-32 / HFC-125 in a ratio of 45 mass % / 55 mass % (R410B) ; a mixture of HFC-125 / HFC-143a in a ratio of 50 mass % / 50 mass % (R507C); a mixture of HFC-32 / HFC-125 / HFC-134a in a ratio of 30 mass % / 10 mass % 60 mass %; a mixture of HFC-32 / HFC-125 / HFC-134a in a ratio of 23 mass %/ 25 mass
  • the hydrocarbon refrigerants may be those which are gaseous at 25 °C and one atmospheric pressure.
  • Specific examples of the hydrocarbon refrigerants are alkanes, cycloalkanes and alkenes each having 1 to 5 carbon atoms, preferably 1 to 4 carbon atoms, such as methane, ethylene, ethane, propylene, propane, cyclopropane, butane, isobutane, cyclobutane, methylcyclopropane and a mixture of at least two kinds thereof.
  • the blending ratio of DME to hydrofluorocarbon and/or hydrocarbon refrigerants is not particularly restricted.
  • the total amount of hydrofluorocarbon and/or hydrocarbon may be within the range of preferably 1 to 200 parts by weight, more preferably 10 to 100 parts by weight per 100 parts by weight of DME.
  • the refrigerating machine oil according to the present invention is generally present in the form of a fluid composition admixed with DME alone or with other refrigerants in a refrigerating machine.
  • the mixing ratio of the inventive refrigerating machine oil to the refrigerants are not particularly restricted, but the refrigerating machine oil may be present in a ratio of 1 to 500 parts by weight, more preferably 2 to 400 parts by weight per 100 parts by weight of the refrigerant.
  • the refrigerating machine oil according to the present invention can be used as a refrigerating machine oil for the refrigerant compressors of any types of refrigerating machine.
  • Refrigerating machines to which the inventive refrigerating machine oil is applicable are room air conditioners, packaged air conditioning systems, refrigerators, automobile air conditioners, dehumidifiers, freezers, refrigerating chambers, vending machines, show-cases and cooling systems for chemical plants.
  • the inventive refrigerating machine oil is preferably used in refrigerating machines having sealed compressors.
  • the inventive refrigerating machine oil is also eligible for use in a reciprocating, rotary, or centrifugal type compressor.
  • a sample oil of each of Examples 1 to 14 was prepared by blending the following base oils and additives in accordance with the formulations indicated in Tables 1 - 3.
  • Tables 1 - 3 shows the properties (kinematic viscosity at 40 °C and 100 °C and total acid value) of each sample oils.
  • each of the sample oils was subjected to a friction test in which a test machine was run under a load of 250 lb for two hours after being warmed up at an oil temperature of 100 °C under a load of 150 lb for a period of one minute.
  • the level of abrasion of the test journal (pin) was measured. The results are shown in Tables 1 - 3.
  • Example 1 Example 2 Example 3 Example 4 Example 5 Base oil A B C D E (mass %) 100 100 100 100 100 100 100 100 Additive - - - - - - (mass %) Kinematic (40°C(mm 2 /s) 21.6 68.6 29.5 55.2 16.9 Viscosity 100°C(mm 2 /s) 4.09 8.60 4.35 5 90 3.91 Total acid value (mgKOH/g) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 Miscibility Miscible Miscible Miscible Miscible Volume resistivity ( ⁇ cm) 6.7 ⁇ 10 15 4.1 ⁇ 10 15 5.3 ⁇ 10 15 2.3 ⁇ 10 15 2.1 ⁇ 10 15 Thermal stability test Sample oil appearance Not changed Not changed Not changed Not changed Not changed Not changed Catalyst appearance Not changed Not changed Not changed Not changed Not changed Not changed Not changed Not changed Volume resistivity ( ⁇ ⁇ cm) 1.1 ⁇ 10 15 9.2 ⁇ 10 14 4.6
  • the sample oils of Examples 1 to 14 according to the present invention had an excellent lubricity, miscibility with refrigerants, electric isolation, resistance to hydrolysis and kinematic viscosities, all of which were well-balanced when used in combination with a dimethyl ether refrigerant.

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WO2007020937A1 (fr) 2005-08-17 2007-02-22 Japan Petroleum Exploration Co., Ltd. Composition réfrigérante
WO2007026646A1 (fr) 2005-08-31 2007-03-08 Idemitsu Kosan Co., Ltd. Composition d’huile de réfrigération
WO2007037073A1 (fr) 2005-09-27 2007-04-05 Japan Petroleum Exploration Co., Ltd. Composition refrigerante
US20180327689A1 (en) * 2015-11-13 2018-11-15 Idemitsu Kosan Co., Ltd. Lubricant composition and lubricating method
EP3722396A4 (fr) * 2017-12-08 2021-09-08 JXTG Nippon Oil & Energy Corporation Huile de réfrigérateur et composition de fluide hydraulique pour réfrigérateurs
TWI746786B (zh) * 2017-02-03 2021-11-21 日商Ｊｘｔｇ能源股份有限公司 冷凍機油
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JP2007145922A (ja) * 2005-11-25 2007-06-14 Japan Petroleum Exploration Co Ltd 冷媒組成物
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DE4313584A1 (de) * 1993-04-26 1994-10-27 Leuna Werke Gmbh Kältemittelgemisch
WO1994026835A1 (fr) * 1993-05-14 1994-11-24 Engels Bernardina C M Dispositif de refroidissement
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Publication number Priority date Publication date Assignee Title
EP0384724A1 (fr) * 1989-02-22 1990-08-29 Nippon Oil Co. Ltd. Procédé de lubrification d'appareils réfrigérants
DE4313584A1 (de) * 1993-04-26 1994-10-27 Leuna Werke Gmbh Kältemittelgemisch
WO1994026835A1 (fr) * 1993-05-14 1994-11-24 Engels Bernardina C M Dispositif de refroidissement
EP0724003A2 (fr) * 1995-01-25 1996-07-31 Oho, Suk Jae Composition réfrigérante

Cited By (12)

* Cited by examiner, † Cited by third party
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WO2007020937A1 (fr) 2005-08-17 2007-02-22 Japan Petroleum Exploration Co., Ltd. Composition réfrigérante
WO2007026646A1 (fr) 2005-08-31 2007-03-08 Idemitsu Kosan Co., Ltd. Composition d’huile de réfrigération
EP1921126A1 (fr) * 2005-08-31 2008-05-14 Idemitsu Kosan Co., Ltd. Composition d'huile de réfrigération
EP1921126A4 (fr) * 2005-08-31 2009-01-21 Idemitsu Kosan Co Composition d'huile de réfrigération
US8070978B2 (en) 2005-08-31 2011-12-06 Idemitsu Kosan Co., Ltd. Refrigerator oil composition
KR101316983B1 (ko) * 2005-08-31 2013-10-11 이데미쓰 고산 가부시키가이샤 냉동기유 조성물
WO2007037073A1 (fr) 2005-09-27 2007-04-05 Japan Petroleum Exploration Co., Ltd. Composition refrigerante
US20180327689A1 (en) * 2015-11-13 2018-11-15 Idemitsu Kosan Co., Ltd. Lubricant composition and lubricating method
TWI746786B (zh) * 2017-02-03 2021-11-21 日商Ｊｘｔｇ能源股份有限公司 冷凍機油
US11377619B2 (en) 2017-02-03 2022-07-05 Eneos Corporation Refrigerating machine oil
EP3722396A4 (fr) * 2017-12-08 2021-09-08 JXTG Nippon Oil & Energy Corporation Huile de réfrigérateur et composition de fluide hydraulique pour réfrigérateurs
US11365368B2 (en) 2017-12-08 2022-06-21 Eneos Corporation Refrigerator oil and hydraulic fluid composition for refrigerators

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