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WO1994009096A1 - Composition de fluide energetique - Google Patents

Composition de fluide energetique Download PDF

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Publication number
WO1994009096A1
WO1994009096A1 PCT/GB1993/002036 GB9302036W WO9409096A1 WO 1994009096 A1 WO1994009096 A1 WO 1994009096A1 GB 9302036 W GB9302036 W GB 9302036W WO 9409096 A1 WO9409096 A1 WO 9409096A1
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WIPO (PCT)
Prior art keywords
working fluid
fluid composition
base oil
compounds
formula
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.)
Ceased
Application number
PCT/GB1993/002036
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English (en)
Inventor
Stuart Corr
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.)
Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to EP93921031A priority Critical patent/EP0663942A1/fr
Priority to JP6509729A priority patent/JPH08502769A/ja
Publication of WO1994009096A1 publication Critical patent/WO1994009096A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—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
    • 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
    • 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
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
    • 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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/044—Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
    • 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
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • 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
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/286—Esters of polymerised unsaturated acids
    • 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
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy 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
    • 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
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • 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
    • 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
    • C10N2040/32—Wires, ropes or cables lubricants
    • 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
    • C10N2040/34—Lubricating-sealants
    • 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
    • C10N2040/36—Release agents or mold release agents
    • 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
    • C10N2040/38—Conveyors or chain belts
    • 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
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • 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
    • C10N2040/42—Flashing oils or marking oils
    • 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
    • C10N2040/44—Super vacuum or supercritical use
    • 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
    • C10N2040/50—Medical uses

Definitions

  • the present invention relates to working fluid compositions for use in heat transfer devices and is particularly concerned with working fluid compositions for use in heat transfer devices which comprise means for controlling the compressor discharge temperature.
  • Heat transfer devices of the mechanical compression type such as refrigerators, freezers, heat pumps and automobile air conditioning systems are well known.
  • a refrigerant liquid of a suitable boiling point evaporates at low pressure taking heat from a surrounding zone.
  • the resulting vapour is then compressed and passes to a condenser where it condenses and gives off heat to a second zone.
  • the condensate is then returned through an expansion valve to the evaporator so completing the cycle.
  • the mechanical energy required for compressing the vapour and pumping the liquid may be provided by an electric motor or an internal combustion engine.
  • the properties preferred of a refrigerant include low toxicity, non- flammability , non-corrosivity , high stability and freedom from objectionable odour.
  • chlorofluorocarbon refrigerants such as dichlorodifluoromethane (Refrigerant R-12) , chlorodifluoromethane (Refrigerant R-22) , or the azeotropic mixture of chlorodifluoromethane and chloropenta luoroethane (Refrigerant R-115); the azeotrope being Refrigerant R-502.
  • hydrofluoroalkanes i.e. compounds which contain only carbon, hydrogen and fluorine atoms in their structure, in place of the chlorofluorocarbons.
  • the hydrofluoroalkanes of particular interest are those compounds which have comparable boiling points and other thermal properties to the chlorofluorocarbons which they are replacing, but which are also less damaging or benign to the ozone layer. Particular mention may be made of 1 , 1 , 1 , 2-tetrafluoroethane (R-134a ) .
  • the refrigerant forms part of a working fluid composition which also comprises a lubricant.
  • the lubricant circulates around the device along with the refrigerant and provides for continual lubrication of the compressor.
  • the properties desired of a lubricant - include good hydrolytic stability and good thermal stability.
  • the lubricant should be compatible with the refrigerant, which in practice means that the lubricant and refrigerant -- should possess a degree of mutual solubility, i.e. the lubricant and the refrigerant should be at least partially soluble in one another.
  • the present applicants have developed a working fluid composition which comprises a refrigerant having a zero ozone depletion potential and a lubricant which - A -
  • the working fluid composition of the invention can provide a viable replacement for at least some of the working fluid compositions presently in use which comprise a chlorofluorocarbon refrigerant and a mineral oil lubricant .
  • a working fluid composition which comprises:
  • (B) sufficient to provide lubrication of a lubricant comprising an ester base oil which comprises the reaction product of at least one neopentyl polyol and at least one aliphatic carboxylic acid or an esterifiable derivative thereof.
  • Difluoromethane being a small molecule, will tend to result in a high compressor discharge temperature when used for high lift, single stage compression.
  • heat transfer devices which use difluoromethane as the refrigerant will preferably comprise means for controlling the compressor discharge temperature in terms of limiting the maximum discharge temperature which is attained.
  • Heat transfer devices which are able to control the compressor discharge temperature are known in the art. Typically, this temperature control is brought about by injecting a flow of lubricant into the compressor and/or by injecting a flow of liquid refrigerant into the compressor. Both these techniques provide for efficient cooling of the compressor and thus control of the compressor discharge temperature.
  • Heat transfer devices which comprise means for controlling the compressor discharge temperature often employ screw compressors, which may be of single or twin screw construction, although heat transfer devices of the reciprocating compressor type which make use of liquid refrigerant injection for cooling purposes are also known in the art.
  • the heat transfer device should be able to maintain the compressor discharge temperature below 150°C, for example below 130°C.
  • a heat transfer device which comprises means for controlling the compressor discharge temperature and which uses as a working fluid composition a composition comprising:
  • (B) sufficient to provide lubrication of a lubricant comprising an ester base oil which comprises the reaction product of at least one neopentyl polyol and at least one aliphatic carboxylic acid or an esterifiable derivative thereof.
  • the lubricant component of the working fluid composition of the invention comprises an ester base oil.
  • the ester base oil should be capable of dissolving enough of the difluoromethane refrigerant to allow for the transport of the lubricant around the heat transfer system and the return of the lubricant to the compressor. In general, this means that the ester base oil should be capable of dissolving at least 5.0 Z by weight on the weight of the oil of the difluoromethane refrigerant at a pressure of 40 psi (40 lb/in 2 ) and a temperature of 0°C.
  • the lubricant component should have a viscosity at 40°C within the range of from 46 to 220 cSt.
  • the heat transfer device is of a type which uses a liquid refrigerant injection technique to control the compressor discharge temperature
  • the lubricant component will preferably have a viscosity at 40°C in the range of from 46 to 100 cSt, more preferably in the range of from 46 to 85 cSt and especially in the range of from 46 to 68 cSt.
  • the lubricant component when the heat transfer device is of a type which uses the cooling action produced by injecting a flow of lubricant to control the compressor discharge temperature, the lubricant component will preferably have a viscosity at 40°C in the range of from 68 to 220 cSt, more preferably in the range of from 100 to 190 cSt and especially in the range of from 125 to 175 cSt.
  • the viscosity index of the lubricant component which is a measure of how the viscosity changes with temperature, is preferably in the range of from 50 to 200, more preferably in the range of from 60 to 150 and particularly preferably in the range of from 90 to 130.
  • preferred lubricants have a pour point of below -20°C, more preferably below -30°C and particularly preferably below -40°C.
  • Suitable neopentyl polyols for the formation of the ester base oil include pentaerythritol , polypentaerythritols such as di- and tripentaerythritol , trimethylol alkanes such as trimethylol ethane and trimethylol propane, and neopentyl glycol.
  • the esters may be formed with linear and/or branched aliphatic carboxylic acids, such as linear and/or branched alkanoic acids.
  • a minor proportion of an aliphatic polycarboxylic acid, e.g. an aliphatic dicarboxylic acid may also be used in the synthesis of the ester in order to increase the viscosity thereof.
  • an aliphatic polycarboxylic acid when employed in the synthesis, it will preferably constitute no more than 30 mole Z, more preferably no more than 10 mole Z of the carboxylic acids used in the synthesis.
  • the amount of the carboxylic acid(s) which is used in the synthesis will be sufficient to esterify all of the hydroxyl groups contained in the polyol, although residual hydroxyl functionality may be acceptable. It will be appreciated that esterifiable derivatives of carboxylic acids may be used in the synthesis if desired.
  • a preferred lubricant for use in the working fluid composition of the invention is one in which the ester base oil comprises the reaction product of at least one neopentyl polyol selected from pentaerythritol, dipentaerythritol ar * ! tripentaerythritol and at least one aliphatic carboxylic acid selected from the straight chain (linear) aliphatic carboxylic acids and the branched aliphatic carboxylic acids .
  • esterifiable derivatives of the carboxylic acids may also be used in the synthesis, such as the acyl halides, anhydrides and lower alkyl esters thereof, and hereinafter whenever reference is made to the use of carboxylic acids in the synthesis of the ester base oil the use of esterifiable derivatives thereof is not to be excluded.
  • Suitable acyl halides are the acyl chlorides and suitable lower alkyl esters are the methyl esters .
  • the base oil in this preferred lubricant comprises one or more ester compounds of formula:
  • R is the hydrocarbon radical remaining after removing the hydroxyl groups from pentaerythritol, dipentaer thritol or tripentaerythritol ; each ⁇ L - ⁇ is, independently, a straight chain (linear) aliphatic hydrocarbyl group or a branched aliphatic hydrocarbyl group; and n is an integer of 4, 6 or 8.
  • the aliphatic hydrocarbyl groups specified for -- above may be substituted, e.g. by pendant atoms or groups such as chloro, fluoro and bromo , and/or by in chain hetero atoms such as oxygen and nitrogen.
  • such hydrocarbyl groups are unsubstituted and thus contain only carbon and hydrogen atoms .
  • a suitable base oil may comprise a single ester compound of Formula I, i.e. the product which is formed from the reaction of a single pentaerythritol type neopentyl polyol and a single carboxylic acid.
  • a suitable base oil may comprise two or more compounds of Formula I.
  • Such a base oil may be prepared by utilising two or more pentaerythritol type neopentyl polyols and/or two or more carboxylic acids in the synthesis of the ester, or by combining a mixture of different ester compounds each of which is the reaction product of a particular pentaerythritol type neopentyl polyol and a particular carboxylic acid.
  • mixed ester compositions each of which has been prepared by utilising two or more pentaerythritol type neopentyl polyols and/or two or more carboxylic acids in their synthesis, may also be blended together to form the ester base oil .
  • a preferred ester base oil comprises one or more compounds of Formula I in which each R 1 is, independently, a linear alkyl group or a branched alkyl group.
  • Preferred linear alkyl groups for R 1 are the C ⁇ _ linear alkyl groups, and ester compounds containing such alkyl groups can be prepared by using at least one c 5-10 linear alkanoic acid selected from pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid and decanoic acid in the synthesis of the ester base oil.
  • Particularly preferred linear alkyl groups for R 1 are the C _ ⁇ linear alkyl groups, especially the linear C4 and linear Cg alkyl groups which are derived from pentanoic and heptanoic acids respectively.
  • the linear C Q alkyl group is an especially preferred linear alkyl group.
  • Preferred branched alkyl groups for R 1 are the C 6 - 9 branched alkyl groups, and ester compounds containing such alkyl groups can be prepared by using at least one C _IQ branched alkanoic acid in the synthesis of the ester base oil, such as 2-methylhexanoic acid, 3-methylhexanoic acid, 4-methylhexanoic acid, 2,2-dimethylpentanoic acid, 2 , -dimethylpentanoic acid, 2-ethylpentanoic acid, 3-ethylpentanoic acid, 2-ethylhexanoic acid, 3 , 5-dimethylhexanoic acid, 2, 2-dimethylhexanoic acid, 2-methylheptanoic acid, 3-methylheptanoic acid, 4-methylheptanoic acid, 2,2-dimethylheptanoic acid, 3 , 5 , 5-trimethylhexanoic acid, 2-methyloctanoic acid, 3-methyl
  • a particularly preferred ester base oil is obtained when a combination of linear and branched alkanoic acids are used in the synthesis thereof so that the oil comprises one or more compounds of Formula I in which at least a proportion of the K-- groups are linear alkyl groups and at least a proportion of the R-- groups are branched alkyl groups.
  • the ester base oil will preferably comprise one or more ester compounds derived from dipentaerythritol, i.e. compounds of Formula I in which R is the hydrocarbon radical remaining after removing the hydroxyl groups from dipentaerythritol.
  • Such ester oils may also comprise one or more ester compounds of Formula I in which R is the hydrocarbon radical remaining after removing the hydroxyl groups from pentaerythritol and/or tripentaerythritol .
  • Preferably at least 25 weight Z, more preferably at least 50 weight Z and particularly preferably at least 75 weight Z of the ester base oil will be comprised of one or more ester compounds derived from dipentaerythritol.
  • the lubricant will also comprise one or more of the additives which are conventional in the refrigeration lubricants art. Specific mention may be made of antioxidants , deacidifying agents, anti-wear agents and extreme pressure resistance agents. Such additives are well known to those skilled in the art. Where the lubricant comprises such additives, they may be present in the amounts conventional in the art. Preferably, the cumulative weight of all the additives will not be more than 8 Z, e.g. 5 Z, of the total weight of the lubricant.
  • Preferred antioxidants are the compounds containing a hindered phenol in the molecule
  • preferred deacidifying agents are the compounds containing an epoxy group in the molecule
  • the preferred anti-wear and extreme pressure resistance agents are the organophosphorous compounds, particularly the organo phosphates, phosphites and thiophosphates .
  • the following compounds are representative of the preferred antioxidants, deacidifying agents, anti-wear agents and extreme pressure resistance agents.
  • Antioxidants 2, 6-di-t-butyl-4-methylphenol, 2,6-di-t-butyl-4-ethylphenol, 2, 6-di-t-butyl-4-hydroxyphenol,
  • Deacidifying agents Phenyl glycidyl ether, butylglycidyl ether, bisphenol A epichlorohydrin condensate, vinylcyclohexene dioxide,
  • Anti-wear and extreme pressure agents Tricresyl phosphate, trisnonylphenylphosphite , distearyl phosphate, tributylphosphate , trilaurylphosphate , trilaurylphosphite , mono-di-mixed-lauryl phosphite. mono-di-mixed-tridecyl phosphate, mono-2-ethylhexyl- 2-ethylhexylphosphate , di-2-ethylhexyl phosphate and the like .
  • the working fluid compositions of the invention typically comprise from 30 to 99 Z by weight, e.g from 70 to 99 Z by weight, of R-32 and from 1 to 70 Z by weight, e.g. from 1 to 30 Z by weight, of the lubricant .
  • the working fluid compositions may be used to provide cooling by a method involving condensing the refrigerant and thereafter evaporating it in a heat exchange relationship with a body to be cooled. They may also be used to provide heating by a method involving condensing the refrigerant in a heat exchange relationship with a body to be heated and thereafter evaporating it.
  • a refrigeration test rig incorporating a screw compressor was filled with "Emkarate” (TM) RL-150S refrigeration lubricant (see below) and difluoromethane (R-32) refrigerant and the performance of the resulting working fluid composition in the test rig examined over a prolonged period of operation.
  • the test rig was kept running for over 1000 hours and no serious operational problems were encountered, showing that the lubricant provided effective lubrication of the compressor in the presence of the difluoromethane refrigerant.
  • the lubricant comprises an ester base oil which is derived from the reaction of dipentaerythritol, n-heptanoic acid and 3 , 5 , 5-trimethy1 hexanoic acid.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)

Abstract

Composition de fluide énergétique comprenant (A) un réfrigérant qui se compose essentiellement de difluorométhane (R-32), et (B) un lubrifiant comprenant une huile basique à ester qui se compose du produit de la réaction entre au moins un polyol de néopentyle et au moins un acide carboxylique aliphatique ou un dérivé estérifiable de ce dernier. Un dispositif de transfert thermique contenant cette composition de fluide énergétique est également revendiqué.
PCT/GB1993/002036 1992-10-09 1993-09-30 Composition de fluide energetique Ceased WO1994009096A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP93921031A EP0663942A1 (fr) 1992-10-09 1993-09-30 Composition de fluide energetique
JP6509729A JPH08502769A (ja) 1992-10-09 1993-09-30 作動流体組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB929221217A GB9221217D0 (en) 1992-10-09 1992-10-09 Working fluid composition
GB9221217.4 1992-10-09

Publications (1)

Publication Number Publication Date
WO1994009096A1 true WO1994009096A1 (fr) 1994-04-28

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ID=10723185

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PCT/GB1993/002036 Ceased WO1994009096A1 (fr) 1992-10-09 1993-09-30 Composition de fluide energetique

Country Status (4)

Country Link
EP (1) EP0663942A1 (fr)
JP (1) JPH08502769A (fr)
GB (1) GB9221217D0 (fr)
WO (1) WO1994009096A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0653479A4 (fr) * 1993-05-27 1995-11-22 Tonen Corp Huile pour machines frigorifiques.
EP0695797A3 (fr) * 1994-08-02 1996-06-26 Exxon Research Engineering Co Des esters de pentaerythritol technique comme base lubrifiante synthétique
US6228820B1 (en) 1995-09-25 2001-05-08 Kao Corporation Method for using thermally stable esters in a lubricating oil for a refrigerating machine
AU754308B2 (en) * 1998-06-11 2002-11-14 APG Polytech, LLC Polyester resin blends with high-level gas barrier properties
CN105473953A (zh) * 2013-09-05 2016-04-06 东芝开利株式会社 压缩机和制冷循环装置
US10167438B2 (en) 2015-03-19 2019-01-01 Hitachi-Johnson Controls Air Conditioning, Inc. Compressor for refrigeration and air conditioning, and refrigeration and air conditioning device
EP2832833B1 (fr) 2012-03-29 2019-01-16 JX Nippon Oil & Energy Corporation Composition de fluide de travail pour réfrigérateur

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5696237B2 (ja) * 2014-01-17 2015-04-08 Ｊｘ日鉱日石エネルギー株式会社 冷凍機油及び冷凍機用流体組成物
JP5608826B2 (ja) * 2014-01-24 2014-10-15 Ｊｘ日鉱日石エネルギー株式会社 冷凍機油
WO2015140918A1 (fr) * 2014-03-18 2015-09-24 株式会社日立製作所 Dispositif réfrigérant et compresseur pour dispositif réfrigérant
TWI555838B (zh) * 2015-02-10 2016-11-01 百達精密化學股份有限公司 迴轉式螺桿壓縮機的潤滑方法
TWI522456B (zh) * 2015-03-27 2016-02-21 Novel refrigeration oil
JP5919430B2 (ja) * 2015-11-05 2016-05-18 Ｊｘエネルギー株式会社 冷凍機油

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EP0475751A1 (fr) * 1990-09-12 1992-03-18 Kao Corporation Composition de fluide de travail pour machine de réfrigération
EP0480479A2 (fr) * 1989-07-05 1992-04-15 Japan Energy Corporation Lubrifiants pour la refrigeration
EP0485979A2 (fr) * 1990-11-16 1992-05-20 Hitachi, Ltd. Appareil frigorifique et compresseur pour réfrigérant
EP0498152A1 (fr) * 1991-01-17 1992-08-12 Cpi Engineering Services, Inc. Composition lubrifiante pour réfrigerants fluorés
WO1992018580A1 (fr) * 1991-04-19 1992-10-29 Allied-Signal Inc. Compositions de refrigeration contenant un refrigerant hydrofluorocarbure et un lubrifiant
JPH0525484A (ja) * 1991-07-20 1993-02-02 Kao Corp 冷凍機作動流体用組成物

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US4254637A (en) * 1979-10-19 1981-03-10 Vilter Manufacturing Corporation Refrigeration system with refrigerant cooling of compressor and its oil
EP0480479A2 (fr) * 1989-07-05 1992-04-15 Japan Energy Corporation Lubrifiants pour la refrigeration
EP0475751A1 (fr) * 1990-09-12 1992-03-18 Kao Corporation Composition de fluide de travail pour machine de réfrigération
EP0485979A2 (fr) * 1990-11-16 1992-05-20 Hitachi, Ltd. Appareil frigorifique et compresseur pour réfrigérant
EP0498152A1 (fr) * 1991-01-17 1992-08-12 Cpi Engineering Services, Inc. Composition lubrifiante pour réfrigerants fluorés
WO1992018580A1 (fr) * 1991-04-19 1992-10-29 Allied-Signal Inc. Compositions de refrigeration contenant un refrigerant hydrofluorocarbure et un lubrifiant
JPH0525484A (ja) * 1991-07-20 1993-02-02 Kao Corp 冷凍機作動流体用組成物

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DATABASE WPI Week 9310, Derwent World Patents Index; AN 93-080650 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0653479A4 (fr) * 1993-05-27 1995-11-22 Tonen Corp Huile pour machines frigorifiques.
EP0695797A3 (fr) * 1994-08-02 1996-06-26 Exxon Research Engineering Co Des esters de pentaerythritol technique comme base lubrifiante synthétique
US6228820B1 (en) 1995-09-25 2001-05-08 Kao Corporation Method for using thermally stable esters in a lubricating oil for a refrigerating machine
AU754308B2 (en) * 1998-06-11 2002-11-14 APG Polytech, LLC Polyester resin blends with high-level gas barrier properties
EP2832833B1 (fr) 2012-03-29 2019-01-16 JX Nippon Oil & Energy Corporation Composition de fluide de travail pour réfrigérateur
CN105473953A (zh) * 2013-09-05 2016-04-06 东芝开利株式会社 压缩机和制冷循环装置
CN105473953B (zh) * 2013-09-05 2017-09-05 东芝开利株式会社 压缩机和制冷循环装置
US10167438B2 (en) 2015-03-19 2019-01-01 Hitachi-Johnson Controls Air Conditioning, Inc. Compressor for refrigeration and air conditioning, and refrigeration and air conditioning device

Also Published As

Publication number Publication date
GB9221217D0 (en) 1992-11-25
EP0663942A1 (fr) 1995-07-26
JPH08502769A (ja) 1996-03-26

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