WO2017074236A1 - Lubrifiant frigorifique - Google Patents

Lubrifiant frigorifique Download PDF

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Publication number
WO2017074236A1
WO2017074236A1 PCT/SE2016/000060 SE2016000060W WO2017074236A1 WO 2017074236 A1 WO2017074236 A1 WO 2017074236A1 SE 2016000060 W SE2016000060 W SE 2016000060W WO 2017074236 A1 WO2017074236 A1 WO 2017074236A1
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WO
WIPO (PCT)
Prior art keywords
acid
lubricant
dioxane
refrigerant
refrigeration
Prior art date
Application number
PCT/SE2016/000060
Other languages
English (en)
Inventor
Par JORGENSEN
David James
Eric Appelman
Pia WENNERBERG
Original Assignee
Perstorp Ab
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Perstorp Ab filed Critical Perstorp Ab
Publication of WO2017074236A1 publication Critical patent/WO2017074236A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M105/34—Esters of 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
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/12—Hydrocarbons
    • C09K2205/126—Unsaturated fluorinated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2207/2895—Partial esters containing free hydroxy groups used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/069—Linear chain compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/071—Branched chain compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/09—Characteristics associated with water
    • C10N2020/097—Refrigerants
    • C10N2020/099—Containing Chlorofluorocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/09—Characteristics associated with water
    • C10N2020/097—Refrigerants
    • C10N2020/101—Containing Hydrofluorocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/74—Noack Volatility
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants

Definitions

  • the present invention refers to a refrigeration lubricant comprising at least one monoester or diester of at least one 1,3-dioxane having at least one hydroxy or hydroxyalkyl group and at least one monocarboxylic acid having 2 to 12 carbon atoms and optionally one or more additives.
  • the present invention further refers to a refrigeration working fluid comprising at least one lubricant according to the invention and at least one halocarbon and/or halo-olefin refrigerant.
  • Esters and polyesters used as lubricants are well-known in the art and used in a wide range of applications including automotive and aviation oils, metal working fluids, gear oils, turbo oils, hydraulic fluids and refrigeration lubricants.
  • Refrigeration systems like refrigerators, freezers, air conditioners, heat pumps normally include a circulating and heat transferring refrigerant.
  • a refrigeration compression circuit typically comprises a compressor, a condenser, expansion device(s) and an evaporator.
  • the refrigerant and compressor lubricant in most cases circulate throughout the system without phase separation. A potential phase separation may include inadequate lubrication of the compressor and reduced heat exchange efficiency.
  • Lubricants for refrigeration systems must thus be compatible and miscible within a wide range of temperatures with said refrigerant in order for the resulting refrigeration working fluids to work properly and lubricate moving parts in the system.
  • halocarbon refrigerants are well-known and those containing chlorine are presently, due to their negative environmental effect, being replaced by chlorine free compounds such as fluorocarbons. Retrofitting of compressor refrigeration systems with newer refrigerants that exhibit no ozone depletion and low global warming potential has become important. The changes made in moving from chlorinated fluorocarbons (CFCs) to hydro fluorinated olefins (HFOs) have impacted the type of lubricant basestock that can be used with the refrigerant. The original lubricants used with CFCs and hydrochlorofluorocarbons (HCFCs) were based on refined naphthenic base oils.
  • alkylated benzenes were used.
  • alkylated benzene-based compressor oils are not compatible with chlorine-free hydroflurocarbon (HFC) refrigerants.
  • polyol esters which are compatible with these refrigerants, replaced alkylated benzenes.
  • the CFCs and HCFCs used mineral oils. All the new options use synthetic lubricants like polyalkylene glycols and esters. The synthetic oils are more hydrophilic than mineral oils and therefore need to be handled more carefully.
  • Polyalkylene glycols and polyol esters are polar basestocks that have significantly better HFC and HFO miscibility and excellent low-temperature characteristics compared with mineral oils and alkylated benzenes.
  • Polyol esters are the most commonly used lubricants for stationary refrigeration applications.
  • Polyalkylene glycols are used in most automotive air conditioning applications.
  • Alkylated benzenes and polyvinyl ethers are used in some applications.
  • a refrigeration lubricant The missions of a refrigeration lubricant are to lubricate internal parts, remove heat generated during compression, clean the system, act as a fluid seal and reduce energy requirements. Compressor design and operating conditions are important parameters when selecting a lubricant. When a gas is compressed, the lubricant in the compression zone picks up some of the heat of compression, which is subsequently dissipated elsewhere in the system. The lubricant also assists in keeping the refrigeration compressor clean. A filter is usually present and the lubricant helps transport various solid contaminants to the filter for removal. Refrigeration systems also have a variety of 'non-contact' surfaces that require sealing (e.g., cylinder/piston walls). The lubricant seals these surfaces and prevents the refrigerant gas from passing through. Other functions of the lubricant are to control foam and reduce noise generated by moving parts of the compressor.
  • the lubricant may travel with the refrigerant as it escapes from the compressor, a concept called "entrapment" in the system.
  • Lubricant entrapped by refrigerant can be in quantities up to 5% or more. This entrapment can lead to poor oil return resulting in oil starvation, if not managed properly by making sure of sufficient refrigerant miscibility or by making hardware accommodations (such as an oil separator). This entrapment can also coat the inner surfaces of the system devices responsible for evaporating and condensing the refrigerant. This phenomenon can lead to a decrease in the effectiveness of the heat exchange, which reduces the performance of the refrigeration system.
  • lubricant esters can be modified by the use of different polyols and by the use of carboxylic acids that have either branched or linear chains.
  • Esters based on linear chain acids in general have good lubricity but often suffer from limited miscibility with hydrofluorocarbon refrigerants.
  • esters based on branched chain acids exhibit good miscibility but poorer viscosity.
  • a mix of acids is used to formulate a polyester blend with specific properties required by the refrigeration system. Polyester lubricants that are based on lower molecular weight alcohols tend to be more miscible than those based on higher molecular weight alcohols.
  • Polyester lubricants based on linear acids are often less miscible when manufactured in higher viscosity grades due to the use of higher molecular weight acids. Thus in order for the lubricant to be compatible with the refrigerant, linear chained acids and low molecular weight are essential.
  • the present invention refers to a lubricant that has quite unique properties that are highly suitable for refrigeration systems.
  • the problem of obtaining both satisficing viscosity and miscibility with the refrigerant is overcome by using the lubricant of the present invention.
  • Said lubricant comprises an ester that has shown to have a high viscosity, which is requested for good lubricity.
  • the lubricant ester of the present invention has furthermore a low molecular weight and a polar characteristic similar to hydrofluorocarbons and hydro fluorinated olefins, resulting in good mutual solubility. High polarity is often required for newer refrigerants.
  • the lubricant ester of the present invention has shown to exhibit surprisingly high viscosity in relation to molecular weight.
  • Another advantageous property of the lubricant ester of the invention is low volatility.
  • a low volatility contributes to low oil consumption.
  • Most refrigeration systems are hermetic, i.e. closed systems, but there are also semi-hermetic refrigeration systems, in which a low volatility of the lubricant is of essence.
  • service intervals can be extended, and then the need to add more surfactant oil to the refrigeration system is decreased.
  • the low weight loss indicates that the lubricant ester of the present invention has a high thermal stability and oxidation resistance. These are properties that help minimise deposit formation and also contributes to extended service intervals. Lower volatility also means a lower fire risk which makes the handling of the lubricant oil a lot safer.
  • lubricating ester of the present invention primarily is intended to be used in refrigeration system, its polarity and high viscosity in relation to molecular weight also makes it suitable as lubricant in for instance hydraulic oils, transmission fluids, automotive 4-stroke oils and rotary vane compressors.
  • the present invention accordingly refers to a refrigeration lubricant comprising at least one monoester or diester of at least one 1,3-dioxane having at least one hydroxy or hydroxyalkyl group and at least one monocarboxylic acid having 2 to 12 carbon atoms and optionally one or more additives.
  • Said 1,3-dioxane preferably has at least two hydroxy or hydroxyalkyl groups, which suitably are vicinal hydroxy and/or hydroxyalkyl groups.
  • the 1,3-dioxane is preferably 5,5-dihydroxyalkyl- 1,3-dioxane, where the alkyl is C 1-C3 and most preferably the 1 ,3-dioxane is 5,5-dihydroxymethyl-l ,3-dioxane.
  • Said monocarboxylic acid is valeric acid, isovaleric acid, hexanoic acid isohexanoic acid, 2-methylhexanoic acid, 2-ethylhexanoic acid, 2,2-dimethylhexanoid acid, 3,5,5-trimethylhexanoic acid, heptanoic acid, isoheptanoic acid, octanoic acid, isooctanoic acid, nonanoic acid, isononanoic acid and/or 2-propylheptanoic acid.
  • the present invention further refers to a refrigeration working fluid comprising at least one lubricant according to the present invention and at least one halocarbon and/or halo-olefin refrigerant, said refrigerant preferably being a fluorocarbon or a hydrofluorocarbon. More preferably said refrigerant is a difluoroethane, a trifluoroethane, a tetrafluoroethane and/or a pentafluoroethane.
  • said refrigerant is 1,1 -difluoroethane, 1,1,1- trifluoroethane, 1 , 1 , 1 ,2-tetrafluoroethane, 2,3,3,3-tetrafluoro prop-l-ene and/or trans- 1,3, 3,3 - tetrafluoroprop-l-ene.
  • Example 2 Preparation of a lubricant ester of 5,5-dihydroxymethyl- 1,3-dioxane and valeric acid.
  • Example 3 Preparation of a lubricant ester of 5,5-dihydroxymethyl- 1,3-dioxane and 2-ethyl hexanoic acid.
  • Example 4 Preparation of a comparative lubricant ester of neopenthylglycol and valeric acid.
  • Example 7 Evaluation of viscosity and volatility of the esters of examples 2-6.
  • Example 1 Evaluation of viscosity and volatility of the esters of examples 2-6.
  • the volatility was measured by using the Noack test.
  • the Noack volatility of an oil is defined as the weight loss of the oil when it is held under isothermal conditions at 250 °C for a period of 1 hour under a constant flow of air.
  • Thermos-gravimetric analysis (TGA) was used to determine the Noack evaporation loss. This is also valid for Examples 3-6 below.

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

Abstract

La présente invention concerne un lubrifiant frigorifique comprenant au moins un monoester ou un diester d'au moins un 1,3-dioxane comportant au moins un groupe hydroxy ou hydroxyalkyle, et au moins un acide monocarboxylique doté de 2 à 12 atomes de carbone, et éventuellement un ou plusieurs additifs. Le lubrifiant frigorifique de la présente invention comprend un ester polaire qui présente un faible poids moléculaire mais une viscosité élevée, qui rend ledit ester particulièrement approprié comme lubrifiant dans des systèmes frigorifiques. Dans un autre aspect, la présente invention concerne un fluide de travail frigorifique comprenant au moins un lubrifiant selon l'invention et au moins un fluide frigorigène halocarboné et/ou d'oléfine halogénée.
PCT/SE2016/000060 2015-10-27 2016-10-21 Lubrifiant frigorifique WO2017074236A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE1500431-0 2015-10-27
SE1500431 2015-10-27

Publications (1)

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WO2017074236A1 true WO2017074236A1 (fr) 2017-05-04

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112143547A (zh) * 2020-09-22 2020-12-29 上海桉欣新能源科技有限公司 一种制冷压缩机用润滑油及其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB579179A (en) * 1942-11-20 1946-07-25 British Celanese Esters of pentaerythritol acetals and ketols
US4792411A (en) * 1986-12-29 1988-12-20 The Lubrizol Corporation Dioxolanes and thio analogs, derivatives thereof and lubricants and fuels containing same
US5575944A (en) * 1992-08-11 1996-11-19 Kao Corporation Acetal-containing working fluid composition for refrigerating machine
US6096692A (en) * 1994-08-29 2000-08-01 Kao Corporation Synthetic lubricating oil
EP1983040A1 (fr) * 2007-03-29 2008-10-22 NOF Corporation Composition de lubrifiant de réfrigération et composition de fluide de travail réfrigérant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB579179A (en) * 1942-11-20 1946-07-25 British Celanese Esters of pentaerythritol acetals and ketols
US4792411A (en) * 1986-12-29 1988-12-20 The Lubrizol Corporation Dioxolanes and thio analogs, derivatives thereof and lubricants and fuels containing same
US5575944A (en) * 1992-08-11 1996-11-19 Kao Corporation Acetal-containing working fluid composition for refrigerating machine
US6096692A (en) * 1994-08-29 2000-08-01 Kao Corporation Synthetic lubricating oil
EP1983040A1 (fr) * 2007-03-29 2008-10-22 NOF Corporation Composition de lubrifiant de réfrigération et composition de fluide de travail réfrigérant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CONRAD, W. E. ET AL.: "Acetal Esters of Polyols as Lubricants", J. CHEM. ENG. DATA, vol. 8, no. 2, April 1963 (1963-04-01), pages 242 - 243, XP055380102 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112143547A (zh) * 2020-09-22 2020-12-29 上海桉欣新能源科技有限公司 一种制冷压缩机用润滑油及其制备方法
CN112143547B (zh) * 2020-09-22 2022-07-15 上海桉欣新能源科技有限公司 一种制冷压缩机用润滑油及其制备方法

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