WO2023189301A1 - Huile de réfrigérateur et composition de fluide de travail - Google Patents

Huile de réfrigérateur et composition de fluide de travail Download PDF

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Publication number
WO2023189301A1
WO2023189301A1 PCT/JP2023/008669 JP2023008669W WO2023189301A1 WO 2023189301 A1 WO2023189301 A1 WO 2023189301A1 JP 2023008669 W JP2023008669 W JP 2023008669W WO 2023189301 A1 WO2023189301 A1 WO 2023189301A1
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Prior art keywords
acid
mass
ester
less
value
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PCT/JP2023/008669
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English (en)
Japanese (ja)
Inventor
祐也 水谷
由真 関
素也 岡崎
英俊 尾形
昌輝 川口
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Ｅｎｅｏｓ株式会社
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Publication of WO2023189301A1 publication Critical patent/WO2023189301A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • 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
    • 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
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic 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
    • 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

Definitions

  • the present invention relates to refrigeration oil and working fluid compositions.
  • Refrigerating machines such as refrigerators, car air conditioners, room air conditioners, and vending machines are equipped with a compressor to circulate refrigerant within the refrigeration cycle.
  • the compressor is then filled with refrigerating machine oil for lubricating the sliding members.
  • Refrigeration oils generally contain base oils and additives selected depending on the desired properties.
  • Patent Document 1 discloses a refrigerating machine oil whose base oil is an ester of a specific polyhydric alcohol, a carboxylic acid, and an ester having a peroxide value of 1 meq/kg or less.
  • antioxidants are one of the additives commonly used with base oil in refrigeration oil, but according to the study of the present inventors, when a specific ester is used as the base oil, the ester's It has been found that antioxidants may be easily consumed depending on the properties. If the antioxidant is easily consumed, the amount of antioxidant remaining in the refrigerating machine oil decreases, and there is a risk that the originally expected antioxidant function will not be fully exhibited. In addition, especially when a phenolic antioxidant is used as the antioxidant, quinone compounds are generated as the antioxidant is consumed, which may cause coloration.
  • one aspect of the present invention is to provide a refrigerating machine oil that can suppress consumption of antioxidants.
  • One aspect of the present invention is a refrigerated oil containing, as a base oil, an ester of a trihydric alcohol and a fatty acid having 14 to 20 carbon atoms, and an antioxidant, and the peroxide value of the ester is 5 mg/kg or more. It's machine oil.
  • the value of peroxide value (mg/kg) x acid value (mgKOH/g) of the ester may be 100 or less.
  • the value of peroxide value (mg/kg) x acid value (mgKOH/g) of the ester may be 5 or more.
  • Fatty acids having 14 to 20 carbon atoms may include oleic acid.
  • the antioxidant is 2,6-di-tert. -butyl-4-methylphenol.
  • Another aspect of the present invention is a working fluid composition containing the above-mentioned refrigeration oil and a refrigerant.
  • the refrigerant may include hydrocarbons.
  • One embodiment of the present invention is a refrigerating machine oil containing, as a base oil, an ester of a trihydric alcohol and a fatty acid having 14 to 20 carbon atoms, and an antioxidant.
  • a trihydric alcohol is an alcohol that has three hydroxyl groups.
  • the trihydric alcohol may be an aliphatic alcohol.
  • Examples of trihydric alcohols include trimethylolethane, trimethylolpropane, trimethylolbutane, glycerin, and 1,3,5-pentanetriol.
  • the trihydric alcohol is preferably trimethylolpropane.
  • the fatty acid having 14 to 20 carbon atoms may be a saturated fatty acid or an unsaturated fatty acid.
  • the C14 to C20 fatty acids preferably include unsaturated fatty acids, more preferably unsaturated fatty acids having 18 carbon atoms (C18 unsaturated fatty acids), and even more preferably oleic acid.
  • the content of unsaturated fatty acids is 70% by mass or more, 75% by mass or more, 80% by mass or more, or 85% by mass or more, based on the total amount of C14 to C20 fatty acids. It may be 95% by mass or less, 93% by mass or less, or 90% by mass or less.
  • the C14-C20 fatty acid further includes a saturated fatty acid having 14-20 carbon atoms (hereinafter also referred to as "C14-C20 saturated fatty acid”) in addition to oleic acid.
  • C14-C20 saturated fatty acids include tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptahexadecanoic acid, octadecanoic acid, nonadecanoic acid and eicosanoic acid. These C14 to C20 saturated fatty acids may be linear or branched.
  • the C14-C20 saturated fatty acid preferably includes at least one selected from the group consisting of linear C14-C20 saturated fatty acids, and more preferably linear tetradecanoic acid (myristic acid) and linear hexadecanoic acid. (palmitic acid), and linear octadecanoic acid (stearic acid), and more preferably linear tetradecanoic acid (myristic acid), linear hexadecanoic acid (palmitic acid), acid), and linear octadecanoic acid (stearic acid).
  • linear tetradecanoic acid myristic acid
  • linear hexadecanoic acid palmitic acid
  • acid linear octadecanoic acid
  • the C14-C20 fatty acid further contains, in addition to oleic acid, an unsaturated fatty acid having 14-20 carbon atoms other than oleic acid (hereinafter also referred to as "C14-C20 unsaturated fatty acid").
  • C14-C20 unsaturated fatty acids other than oleic acid may have, for example, 1 to 4, 1 to 3, 1 to 2, or 1 carbon-carbon unsaturated bonds.
  • C14-C20 unsaturated fatty acids other than oleic acid examples include physeteric acid, myristoleic acid, palmitoleic acid, heptadecenylenic acid, petroselaidic acid, elaidic acid, vaccenic acid, linoleic acid, linoleraidic acid, hyragonic acid, and linolenic acid. , and arachidonic acid.
  • the C14 to C20 unsaturated fatty acids other than oleic acid preferably include at least one selected from the group consisting of unsaturated fatty acids having 16 to 18 carbon atoms, and more preferably include palmitoleic acid.
  • the C14-C20 fatty acids in addition to oleic acid, further include both C14-C20 saturated fatty acids and C14-C20 unsaturated fatty acids other than oleic acid.
  • the C14 to C20 saturated fatty acids preferably include at least one selected from the group consisting of linear C14 to C20 saturated fatty acids and at least one selected from the group consisting of unsaturated fatty acids having 16 to 18 carbon atoms, More preferably, it contains at least one selected from the group consisting of myristic acid, palmitic acid, and stearic acid, and palmitoleic acid, and even more preferably, it contains myristic acid, palmitic acid, stearic acid, and palmitoleic acid.
  • the content of C14-C20 saturated fatty acids may be 1% by mass or more, 3% by mass or more, or 5% by mass or more, and 15% by mass or less, 12% by mass or less, based on the total amount of C14-C20 fatty acids. , or 10% by mass or less.
  • the content of C14-C20 unsaturated fatty acids other than oleic acid may be 1% by mass or more, 3% by mass or more, or 4% by mass or more, and 10% by mass or less, based on the total amount of C14-C20 fatty acids. , 8% by mass or less, or 6% by mass or less.
  • each fatty acid mentioned above is measured by the following procedure.
  • the ester is dissolved in ethanol and subjected to alkaline hydrolysis, followed by trimethylsilyl (TMS) derivatization using N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA).
  • TMS trimethylsilyl
  • BSTFA N,O-bis(trimethylsilyl)trifluoroacetamide
  • BSTFA N,O-bis(trimethylsilyl)trifluoroacetamide
  • the type of fatty acid constituting the ester is confirmed as a TMS derivatized product by GC/MS analysis of the obtained TMS derivatized fatty acid.
  • each fatty acid is quantified by GC analysis under the following GC conditions.
  • GC conditions ⁇ Column: DB-5, 50°C ⁇ 320°C (15°C/min) ⁇ Injection: 300°C, 1 ⁇ L, split ratio 50:1 ⁇ Detector: FID, 320°C - Standard sample for calibration curve: Palmitic acid (reagent) is used for C14 fatty acids and C16 fatty acids, and stearic acid (reagent) is used for C18 fatty acids. Note that fatty acid ethylation may be generated during the TMS derivatization process, and the amount of fatty acid is calculated by adding up the amount of fatty acid TMS derivatization and the amount of fatty acid ethylation.
  • the peroxide value of the ester of trihydric alcohol and C14 to C20 fatty acid is 5 mg/kg or more, preferably 10 mg/kg or more, 15 mg/kg or more, 20 mg/kg or more, from the viewpoint of suppressing antioxidant consumption. kg or more, or 25 mg/kg or more.
  • the peroxide value of the ester may be 400 mg/kg or less, 350 mg/kg or less, or 320 mg/kg or less.
  • the peroxide value in this specification means the peroxide value measured in accordance with JPI-5S-72.
  • the peroxide value of the ester is within the above range and the acid value of the ester is also within an appropriate range.
  • the value of peroxide value (mg/kg) x acid value (mgKOH/g) of the ester is preferably 1 or more, more preferably 3, from the viewpoint of further suppressing consumption of the antioxidant. above, more preferably 5 or more, 6 or more, 7 or more, or 8 or more, preferably 150 or less, more preferably 130 or less, even more preferably 100 or less, 90 or less, 80 or less, 70 or less, It may be 60 or less, or 50 or less.
  • the acid value of the ester is preferably 1 mgKOH/g or less, more preferably 0.6 mgKOH/g or less, still more preferably 0.5 mgKOH/g or less, from the viewpoint of suppressing consumption of the antioxidant more preferably. It may be 4 mgKOH/g or less, or 0.35 mgKOH/g or less, preferably 0.03 mgKOH/g or more, more preferably 0.05 mgKOH/g or more, still more preferably 0.08 mgKOH/g or more, 0.1 mgKOH /g or more, or 0.12 mgKOH/g or more.
  • the acid value in this specification means the acid value measured in accordance with JIS K2501:2003.
  • the C14 to C20 fatty acid constituting the ester is a C14 to C20 fatty acid with a biomass degree of 50% or more, preferably a biomass degree of 50% or more.
  • An example of this method is to perform ester synthesis using a C14 to C20 unsaturated fatty acid so as to obtain a desired acid value, and then to contact it with air for a certain period of time so as to obtain a desired peroxide value.
  • the peroxide value of the ester can be changed to the peroxide value of the ester synthesized by the usual method. tends to be higher than that.
  • the treatment can be carried out under the necessary conditions. You can do this as appropriate.
  • the biomass degree in this specification conceptually indicates the ratio (%) of the amount of carbon derived from biomass resources (or renewable resources) to the total amount of organic carbon in a sample.
  • the biomass degree is 100% when the base material is 100% derived from biomass resources, and 0% when the base material is 100% derived from petroleum resources. In the case of mixtures of base materials, values are expected depending on the proportion of carbon derived from biomass resources.
  • pMC is the % Modern Carbon value calculated as 14Aspl/14Astd x 100
  • REF (pMC) is the pMC value according to the year of production
  • 14Aspl is the 14C / 12C ratio of the sample
  • 14Astd is the 14C /12C ratio of the standard material. 12 C ratio, and if the calculated value of biomass degree exceeds 100%, it is considered as 100% (see the above test method etc. for details).
  • the biomass degree of the ester or the refrigerating machine oil containing the same may preferably be 50% or more, 70% or more, 80% or more, 85% or more, or 100%, and from the economic point of view, preferably 95% or more. % or less or 92% or less.
  • the content of the ester of trihydric alcohol and C14 to C20 fatty acid is 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more, based on the total amount of refrigerating machine oil. It may be % by mass or more.
  • the refrigeration oil may further contain other base oils than the ester of trihydric alcohol and C14 to C20 fatty acid.
  • Other base oils may be, for example, hydrocarbon oils or oxygenated oils.
  • the hydrocarbon oil include mineral oil, olefin polymers, naphthalene compounds, alkylbenzenes, and the like.
  • oxygen-containing oils include monoesters (esters of monoalcohols), polyol esters other than esters of trihydric alcohols and C14 to C20 fatty acids (esters of polyols having two or more hydroxyl groups), esters such as complex esters, and polyesters such as complex esters.
  • Examples include ethers such as alkylene glycol, polyvinyl ether, polyphenyl ether, and perfluoroether.
  • antioxidants contained in the refrigerating machine oil include phenolic antioxidants and amine antioxidants.
  • examples of the phenolic antioxidant include 2,6-di-tert. -butyl-p-cresol, 2,6-di-tert. -butyl-phenol, and 4,4'-methylenebis(2,6-di-tert.-butyl-phenol).
  • examples of the amine antioxidant include alkyldiphenylamine, naphthylamine, and the like.
  • the antioxidant preferably includes a phenolic antioxidant, more preferably 2,6-di-tert. - Contains butyl-4-methylphenol.
  • the content of the antioxidant may be 0.01% by mass or more, 0.05% by mass or more, or 0.1% by mass or more, and 3% by mass or less, 2% by mass, based on the total amount of refrigerating machine oil. or less, or 1% by mass or less.
  • the refrigeration oil may further contain additives other than antioxidants.
  • additives other than antioxidants include acid scavengers, antiwear agents, oil agents, antifoaming agents, metal deactivators, and viscosity index improvers.
  • the total content of additives other than antioxidants is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and 5% by mass or less or 2% by mass, based on the total amount of refrigerating machine oil. It may be less than % by mass.
  • the refrigeration oil preferably further contains an acid scavenger, more preferably an epoxy acid scavenger.
  • an acid scavenger examples include glycidyl ester compounds, glycidyl ether compounds, and alicyclic epoxy compounds.
  • the content of the acid scavenger may be 0.1% by mass or more and 3% by mass or less based on the total amount of refrigerating machine oil.
  • the refrigeration oil preferably further contains an anti-wear agent, more preferably a phosphorus-based anti-wear agent.
  • the phosphorus-based wear inhibitor include orthophosphoric acid ester compounds, phosphorous acid ester compounds, and thiophosphoric acid ester compounds.
  • the phosphorus anti-wear agent is preferably an orthophosphoric acid ester compound, more preferably at least one selected from tricresyl phosphate, triphenyl phosphate, trialkyl phosphate, and tri(alkylphenyl) phosphate.
  • the content of the anti-wear agent may be 0.1% by mass or more and 3% by mass or less based on the total amount of refrigerating machine oil.
  • the kinematic viscosity of the refrigerating machine oil at 40° C. may be 10 mm 2 /s or more, 20 mm 2 /s or more, 30 mm 2 /s or more, or 40 mm 2 /s or more, and 400 mm 2 /s or less, and 300 mm 2 /s or more. s or less, 200 mm 2 /s or less, 100 mm 2 /s or less, or 60 mm 2 /s or less.
  • the kinematic viscosity of the refrigerating machine oil at 100° C. is 4 mm 2 /s or more, and may be 6 mm 2 /s or more, 8 mm 2 /s or more, or 9 mm 2 /s or more, and 40 mm 2 /s or less, 25 mm 2 /s or more. s or less, 15 mm 2 /s or less, 12 mm 2 /s or less, or 10 mm 2 /s or less.
  • the viscosity index of the refrigerating machine oil may be 110 or more, 140 or more, 150 or more, 160 or more, or 170 or more, and may be 300 or less, 250 or less, or 220 or less.
  • kinematic viscosity and viscosity index refer to kinematic viscosity and viscosity index measured in accordance with JIS K2283:2000.
  • Refrigerating machine oil is used together with a refrigerant. That is, another embodiment of the present invention is a working fluid composition containing refrigerating machine oil and a refrigerant.
  • the refrigerant preferably contains hydrocarbons.
  • the hydrocarbon is preferably a hydrocarbon having 2 to 4 carbon atoms.
  • the hydrocarbon is, for example, at least one selected from the group consisting of ethylene, ethane, propane (R290), propylene, cyclopropane, normal butane, isobutane (R600a), cyclobutane, and methylcyclopropane, preferably propane ( R290) or isobutane (R600a), more preferably propane (R290).
  • the refrigerant may consist only of hydrocarbons, or may further contain other refrigerants in addition to hydrocarbons.
  • the content of hydrocarbons may be 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more, based on the total amount of the refrigerant.
  • the other refrigerants include saturated fluorinated hydrocarbons (HFC) such as R32, R134a, R125, R143a, and R152a, unsaturated fluorinated hydrocarbons (HFO) such as R1234yf and R1234ze, and perfluoroether.
  • HFC saturated fluorinated hydrocarbons
  • HFO unsaturated fluorinated hydrocarbons
  • R1234yf and R1234ze such as R1234yf and R1234ze
  • perfluoroether examples include fluorine ether, bis(trifluoromethyl)sulfide, trifluoroiodide me
  • the content of refrigerating machine oil in the working fluid composition may be 1 part by mass or more or 2 parts by mass or more, and 500 parts by mass or less or 400 parts by mass or less, based on 100 parts by mass of the refrigerant.
  • Trimethylolpropane and a mixture of C14-20 fatty acids with 100% biomass obtained from animal and vegetable oils C14 saturated fatty acids (myristic acid): about 0.2-2% by mass, C16 unsaturated fatty acids (palmitoleic acid)) : about 0.1 to 6% by mass, C16 saturated fatty acid (palmitic acid): about 4 to 6% by mass, C18 unsaturated fatty acid (oleic acid): about 87 to 93% by mass, C18 saturated fatty acid (stearic acid): 1 ⁇ 2% by mass)) (biomass degree approximately 90%) was synthesized to have an acid value of 0 to 0.5mgKOH/g, and the peroxide value was changed by changing the contact time with air, etc.
  • esters Five types were prepared and these esters were used as base oils 1 to 5. Peroxide value (measured according to JPI-5S-72), acid value (measured according to JIS K2501:2003), and peroxide value (mg/kg) x acid value (mgKOH/g) of each ester ) are shown in Table 1.
  • each refrigerating machine oil (30 g) whose water content was adjusted to 1000 ppm was weighed into an autoclave, and a catalyst (iron, copper, and aluminum wire, each with an outer diameter of 1.6 mm and a length of 50 mm) was added to the autoclave.
  • a stability test was conducted by enclosing R290 (30 g) as a refrigerant and then heating it at 175° C. for 168 hours.
  • the antioxidant content (mass) C0 in each refrigeration oil before the stability test and the antioxidant content (mass) C1 in each refrigeration oil after the stability test were determined using HPLC or GC.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Physics & Mathematics (AREA)
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  • Combustion & Propulsion (AREA)
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Abstract

L'invention concerne une huile de réfrigérateur comprenant : un ester d'un alcool trivalent et d'un acide gras en C14 à C20, en tant qu'huile de base ; et un inhibiteur d'oxydation, la valeur de peroxyde de l'ester étant d'au moins 5 mg/kg.
PCT/JP2023/008669 2022-03-31 2023-03-07 Huile de réfrigérateur et composition de fluide de travail WO2023189301A1 (fr)

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JP2022058609A JP2023149832A (ja) 2022-03-31 2022-03-31 冷凍機油及び作動流体組成物
JP2022-058609 2022-03-31

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0625683A (ja) * 1992-07-09 1994-02-01 Kao Corp 冷凍機作動流体用組成物
WO2000068345A1 (fr) * 1999-05-10 2000-11-16 New Japan Chemical Co., Ltd. Huile de lubrification pour refrigerateur, composition de fluide hydraulique pour refrigerateur et procede de lubrification de refrigerateur
WO2013062058A1 (fr) * 2011-10-26 2013-05-02 Ｊｘ日鉱日石エネルギー株式会社 Composition de fluide de travail pour machine de réfrigération et huile de réfrigération
CN104355994A (zh) * 2014-09-12 2015-02-18 大连东方创新科技有限公司 一种芳基烷基多元醇酯及其制备方法和应用
WO2021193443A1 (fr) * 2020-03-27 2021-09-30 出光興産株式会社 Composition d'huile lubrifiante

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0625683A (ja) * 1992-07-09 1994-02-01 Kao Corp 冷凍機作動流体用組成物
WO2000068345A1 (fr) * 1999-05-10 2000-11-16 New Japan Chemical Co., Ltd. Huile de lubrification pour refrigerateur, composition de fluide hydraulique pour refrigerateur et procede de lubrification de refrigerateur
WO2013062058A1 (fr) * 2011-10-26 2013-05-02 Ｊｘ日鉱日石エネルギー株式会社 Composition de fluide de travail pour machine de réfrigération et huile de réfrigération
CN104355994A (zh) * 2014-09-12 2015-02-18 大连东方创新科技有限公司 一种芳基烷基多元醇酯及其制备方法和应用
WO2021193443A1 (fr) * 2020-03-27 2021-09-30 出光興産株式会社 Composition d'huile lubrifiante

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