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EP0536814B1 - use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine. - Google Patents

use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine. Download PDF

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Publication number
EP0536814B1
EP0536814B1 EP92121965A EP92121965A EP0536814B1 EP 0536814 B1 EP0536814 B1 EP 0536814B1 EP 92121965 A EP92121965 A EP 92121965A EP 92121965 A EP92121965 A EP 92121965A EP 0536814 B1 EP0536814 B1 EP 0536814B1
Authority
EP
European Patent Office
Prior art keywords
acid
hfc
lubricant
refrigerant
ester
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.)
Expired - Lifetime
Application number
EP92121965A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0536814A1 (en
Inventor
Takashi C/O Kyodo Oil Tech. Res. Center Kaimai
Hisashi C/O Kyodo Oil Tech. Res. Center Yano
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
Japan Energy Corp
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Filing date
Publication date
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Application filed by Japan Energy Corp filed Critical Japan Energy Corp
Publication of EP0536814A1 publication Critical patent/EP0536814A1/en
Application granted granted Critical
Publication of EP0536814B1 publication Critical patent/EP0536814B1/en
Anticipated expiration legal-status Critical
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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
    • 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
    • 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
    • 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
    • C10M105/40—Esters containing free hydroxy or carboxyl 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
    • 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
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
    • C10M105/44—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/003—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions used as base material
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    • C10M2207/2805—Esters used as base material
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    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • 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
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    • 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
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    • 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

  • This invention relates to the use of lubrificants for compressors using a hydrofluorocarbon refrigerant containing no chlorine such as HFC-134a (1,1,1,2-tetrafluoroethane), for instance
  • Japanese Patent laid open No. 61-281199 describes a mixture of polyglycol represented by a general formula of R1[O-(R2O) m -R3] n , an alkylbenzene and the like
  • Japanese Patent laid open No. 57-63395 describes an oil obtained by mixing a polyether such as high molecular weight polyoxypropylene monobutyl ether with an epoxycycloalkyl compound
  • Japanese Patent laid open No. 59-117590 describes a high viscosity mixed oil of a polyether compound and a paraffinic or naphthanic mineral oil.
  • the conventional synthetic lubricants as mentioned above can not be a refrigeration lubricant using HFC-134a as a refrigerant from a viewpoint of compatibility and the like.
  • polyoxyalkylene glycol (hereinafter abbreviated as PAG) having hydroxyl groups (-OH) at both terminals is reported as a refrigeration lubricant using HFC-134a. Further, it is described that PAG is dissolved in HFC-134a within a wide temperature range as compared with general PAG containing hydroxyl group and alkyl group at its terminals, whereby the recycle of the lubricant into a compressor is improved in the refrigeration system and the seizuring in the actuation of the compressor at high temperature is prevented. Moreover, the temperature range compatible with HFC-134a is described to be between -40°C and +50°C.
  • HFC-134a is a replacing refrigerant of R-12 and is mainly expected for use in a car air conditioner, a refrigerator and the like.
  • the refrigerator it is required to have a good compatibility between lubricant and refrigerant, and further the lubricant itself is necessary to have an electric insulating property because the motor is substantially existent in the refrigeration system.
  • the conventional compounds examined as a lubricant for HFC-134a refrigerant inclusive of PAG disclosed in US Patent No. 4,755,316 are remarkably poor in the electric insulating property as compared with the conventional refrigeration mineral oil and high in the hygroscopicity.
  • an object of the invention to provide a refrigeration lubricant having an excellent, compatibility with a new refrigerant containing no chlorine, such as HFC-134a, for instance within a wide temperature range, a high electric insulating property and a low hygroscopicity.
  • esters At the present, a part of commercially available esters is used in systems using refrigerants R-12, R-22, for instance, but is incompatible with HFC-134a as a new refrigerant or is very narrow in the compatible range therewith.
  • the inventors have aimed at the fact that the ester has a high electric insulating property, a low hygroscopicity, a good lubricity and a high stability as compared with PAG and made various studies with respect to the molecule design of the ester showing a wide range of compatibility with HFC-134a, and found that only esters having a considerably restricted structure can be used in the HFC-134a refrigeration system, and as a result, the invention has been accomplished.
  • the present invention refers to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine, comprising as a main component an ester(s) obtained by reacting (a) neopentyl glycol with (b) at least one branched-chain monovalent fatty acid having a carbon number of 4-18, wherein said ester has a total acid value of not more than 3 mg KOH/g and a hydroxyl value of not more than 50 mg KOH/g.
  • the hydrofluorocarbon refrigerant is 1,1,1,2-tetrafluoroethane (HFC-134a).
  • the refrigeration lubricant for refrigerant HFC-134a and the like comprises an ester obtained by esterifying neopentyl glycol with at least one branched-chain monovalent fatty acid having a carbon number of 4-18 wherein said ester has a total acid value of not more than 3 mg KOH/g and a hydroxyl value of not more than 50mg KOH/g, as a main component.
  • the monovalent fatty acid mention may be made of isobutanoic acid, isopentanoic acid, isoheptanoic acid, 2-ethyl hexanoic acid, 3,5,5-trimethyl hexanoic acid, and isostearic acid, for instance.
  • At least one of these monovalent fatty acids is properly mixed and esterified with neopentyl glycol to obtain an ester satisfying desirable physical properties required for various refrigerators.
  • the amount of the straight or branched-chain fatty acid used is preferable to be not less than 50 mol% per the total monovalent fatty acid used.
  • At least one polybasic acid having a carbon number of 4-36 may be esterified with neopentyl glycol in an amount of not more than 80 mol% per total fatty acid.
  • the polybasic acids considering the more compatibility with the refrigerant HFC-134a and the like and the physical properties of the resulting ester, a polybasic acid having a carbon number of 4-10 is preferable.
  • the polybasic acid includes succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, maleic acid, and trimellitic acid, for instance.
  • the polybasic acid having a carbon number of not more than 3 is a special product and is difficult to be cheaply available and is poor in the stability of the ester after the synthesis. While, when the carbon number exceeds 36, the compatibility of the resulting ester with HFC-134a and the like is largely lowered.
  • the reason why the amount of the polybasic acid added is limited to not more than 80 mol% per the total fatty acid is due to the fact that when it exceeds 80 mol%, the gelation may be caused and it is difficult to obtain desirable physical properties.
  • the ester compounds used in the present invention can be obtained by the esterification reaction through dehydration reaction between the specified polyvalent alcohol and the specified fatty acid as mentioned above, or the general esterification reaction through an acid anhydride, an acid chloride or the like as a derivative of the fatty acid.
  • the ester according to the invention can be obtained by the above method, the remaining acid value and hydroxyl value are not particularly critical.
  • the acid value exceeds 3
  • the acid value exceeds 50
  • the hydroxyl value exceeds 50
  • the hydroxyl value exceeds 50
  • the hydroxyl value is preferable not more than 50 mg KOH/g.
  • the esters used in the invention exhibit a good compatibility with the refrigerant HFC-134a and the like over a wide range of from low temperature to high temperature as a lubricant for use in a refrigerator using HFC-134a as a refrigerant, whereby the lubricity and thermal stability of the refrigeration lubricant can be considerably improved. Furthermore, they are high in the electric insulating property and small in the hygroscopicity as compared with PAG conventionally examined as a refrigeration lubricant for HFC-134a.
  • the refrigeration lubricants comprising the ester used in the invention as a main component can solve the problems on the compatibility with HFC-134a and the hygroscopicity, which have never been solved in the conventional technique, and can further enhance the electric insulating property, which comes into problem when HFC-134a is used in a compressor for a refrigerator.
  • additives usually used in the lubricant such as antioxidant, anti-wear agent and epoxy compound, for instance may properly be added to the refrigeration lubricant used in the invention.
  • Seizuring load (Falex load-carrying capacity) was measured according to ASTM D-3233-73 under a controlled atmosphere of HFC-134a blown.
  • test lubricant Into a beaker of 100 ml was charged 60 g of the test lubricant, which was left to stand at a temperature of 25°C and a humidity of 70% for 3 hours and then the water concentration was measured.
  • the electric insulating property represented by the dielectric constant is 100,000 times or more and the two-phase separation at a high temperature is not caused. Furthermore, the seizuring load is excellent and the hygroscopicity is low.
  • the thermal stability is equal in case of the HFC-134a system, but is considerably excellent in case of the R-12 system. This is very advantageous in practical use because the mixing of HFC-134a and R-12 is not avoided at a stage of replacing the refrigerant from R-12 to HFC-134a.
  • esters used in the invention are compared with the commercially available esters (C-1 - C-2), the two-phase separation temperature is extremely different and the conventional esters are insoluble in HFC-134a. In this point, the molecule designed esters used in the invention have a great merit.
  • esters used in the invention are fairly excellent in the performances as a lubricant as compared with Comparative Examples.
  • the HFC-134a has been mentioned as a possible replacement for R-12 and is used for car air conditioner, refrigerator and the like. Particularly, in case of the car air conditioner, the compressor is driven in summer season, so that the compatibility between oil and refrigerant at high temperature becomes important. When the two-phase separation between oil and refrigerant is caused in the compressor during the driving, the refrigerant having a larger specific gravity remains in the lower portion of the compressor, resulting in the occurrence of compressor seizuring.
  • the motor is included in the compressor, so that leakage of electricity comes into problem.
  • the esters used in the invention have a dielectric constant higher by 100,000 times or more than that of the conventional PAG and are excellent in the electric insulating property, so that they can be said to be a refrigeration lubricant for the refrigerator.
  • HFC-134a causing substantially no breakage of ozone layer is closed up instead of R-12 widely used as a refrigerant in order to cope with the breakage of ozone layer through chlorofluorocarbon and hydrochlorofluorocarbon being a greatest problem in world-wide scale, but is poor in the compatibility with the conventional refrigeration lubricant, which is a bar for the development of replacement system.
  • the refrigeration lubricants used in the invention have a sufficient compatibility with HFC-134a as a refrigerant and a high electric insulating property and also are excellent in the total performances, so that they have an effect that the conventional systems can be used as they are even when HFC-134a is used instead of the conventional R-12 and R-22 as a refrigerant.

Landscapes

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP92121965A 1989-07-05 1989-10-17 use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine. Expired - Lifetime EP0536814B1 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JP17200189 1989-07-05
JP17200089 1989-07-05
JP172001/89 1989-07-05
JP172002/89 1989-07-05
JP172000/89 1989-07-05
JP17200289 1989-07-05
EP89119265A EP0406479B2 (en) 1989-07-05 1989-10-17 Refrigeration lubricants

Related Parent Applications (2)

Application Number Title Priority Date Filing Date
EP89119265.0 Division 1989-10-17
EP89119265A Division-Into EP0406479B2 (en) 1989-07-05 1989-10-17 Refrigeration lubricants

Publications (2)

Publication Number Publication Date
EP0536814A1 EP0536814A1 (en) 1993-04-14
EP0536814B1 true EP0536814B1 (en) 1996-01-24

Family

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Application Number Title Priority Date Filing Date
EP92121965A Expired - Lifetime EP0536814B1 (en) 1989-07-05 1989-10-17 use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine.
EP91121101A Expired - Lifetime EP0479338B1 (en) 1989-07-05 1989-10-17 Use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine.
EP91121100A Expired - Lifetime EP0480479B2 (en) 1989-07-05 1989-10-17 Use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine
EP89119265A Expired - Lifetime EP0406479B2 (en) 1989-07-05 1989-10-17 Refrigeration lubricants

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Application Number Title Priority Date Filing Date
EP91121101A Expired - Lifetime EP0479338B1 (en) 1989-07-05 1989-10-17 Use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine.
EP91121100A Expired - Lifetime EP0480479B2 (en) 1989-07-05 1989-10-17 Use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine
EP89119265A Expired - Lifetime EP0406479B2 (en) 1989-07-05 1989-10-17 Refrigeration lubricants

Country Status (5)

Country Link
EP (4) EP0536814B1 (ko)
KR (3) KR950005694B1 (ko)
DE (4) DE68928281T2 (ko)
ES (4) ES2082341T3 (ko)
SG (2) SG49157A1 (ko)

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Also Published As

Publication number Publication date
EP0406479B2 (en) 2002-09-04
EP0536814A1 (en) 1993-04-14
EP0480479A3 (en) 1992-06-17
DE68928281D1 (de) 1997-10-02
KR970078832A (ko) 1997-12-12
ES2051340T5 (es) 2003-03-16
ES2099120T3 (es) 1997-05-16
EP0479338A2 (en) 1992-04-08
SG49157A1 (en) 1998-05-18
DE68927916T2 (de) 1997-08-21
EP0480479B1 (en) 1997-03-26
ES2099120T5 (es) 2005-03-16
KR970078831A (ko) 1997-12-12
EP0480479B2 (en) 2004-09-01
EP0479338B1 (en) 1997-08-27
DE68927916D1 (de) 1997-04-30
DE68925537D1 (de) 1996-03-07
SG49165A1 (en) 1998-05-18
ES2051340T3 (es) 1994-06-16
KR950005694B1 (ko) 1995-05-29
DE68925537T2 (de) 1996-07-04
EP0480479A2 (en) 1992-04-15
ES2104650T3 (es) 1997-10-16
EP0479338A3 (en) 1992-05-27
DE68914448T2 (de) 1994-08-25
EP0406479A1 (en) 1991-01-09
DE68914448D1 (de) 1994-05-11
KR0131017B1 (ko) 1998-04-14
ES2082341T3 (es) 1996-03-16
EP0406479B1 (en) 1994-04-06
KR910003077A (ko) 1991-02-26
DE68928281T2 (de) 1998-01-15
DE68914448T3 (de) 2003-03-06
KR0131016B1 (ko) 1998-04-14
DE68927916T3 (de) 2005-03-10

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