Classifications

• • 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
  • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
• • 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
  • C10M105/36—Esters of polycarboxylic 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
  • C10M2207/2825—Esters of (cyclo)aliphatic oolycarboxylic acids 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
  • C10M2207/285—Esters of aromatic polycarboxylic acids
  • C10M2207/2855—Esters of aromatic polycarboxylic acids 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
  • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
  • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
  • C10M2227/061—Esters derived from boron

Definitions

• the invention relates to the use of aliphatic or aromatic polycarboxylic acid esters in fully or partially synthetic lubricants and lubricants which contain these esters.
• Modern lubricants especially low-friction motor oils, can no longer be produced using mineral oil components alone; the addition of synthetic components is necessary.
• lubricating oils for motor vehicle engines are subject to ever increasing demands, since speeds, working pressures and outputs are constantly increasing while at the same time demanding a long service life and reliability in engine construction.
• the HD (Heavy Duty) oils to which additives were added for their additional tasks, such as aging and corrosion protection, high pressure resistance, and as "dirt carriers" - were followed by the multigrade oils with flat viscosity curves and a suitability for summer and winter operation, for longer oil change intervals and already reduced fuel consumption, especially in winter and short-haul operations.
• a flat viscosity curve means a reduced temperature dependence of the lubricating oil.
• the viscosity index (VI) is a measure of the temperature dependence.
• US-A-4 130 494 relates to the use of amine salts of phosphate esters as additives to synthetic lubricating oil compositions. This is intended to reduce unwanted deposits in the engines, especially in turbine engines.
• US-A-4 155 861 relates to a lubricant which comprises a mixture of a monomeric ester of a branched dicarboxylic acid with an aliphatic primary monoalcohol and a complex ester of a dicarboxylic acid and hexanediol or trimethylhexanediol.
• the monomeric diester is always a mixed diester (column 6, lines 1 and 2), with octyl trimethyladipate being mentioned in particular.
• the lubricant combination described should be characterized by universal applicability.
• the known polycarboxylic acid esters are produced, for example, on an industrial scale using oxo alcohols as esterification components.
• Oxo alcohols which are particularly suitable for esters as synthetic lubricants, are made from oligo-olefins.
• Table 1 shows examples of known oligo-olefins and the alcohols which can be prepared therefrom by oxo reaction.
• Polycarboxylic esters have already been produced from these industrially available oxo alcohols, which are also used as synthetic lubricants, cf. R.C. Gunderson and A.W. Hunt, Synthetic Lubricants, Reinhold Publishing Company, 1962, pp. 151ff.
• the invention has for its object to provide polycarboxylic acid esters for use in synthetic lubricants which, compared to the known polycarboxylic acid esters, have improved temperature / viscosity behavior, expressed by a higher viscosity index and improved low-temperature properties, as well as a lower evaporation loss and a higher flash point.
• aliphatic or aromatic polycarboxylic acid esters of the general formula I (RO- ) y -X- -OR (I) in which X represents a straight-chain or branched alkylene radical or an arylene radical, R represents a radical originating from the oxidation of an n-butene oligomer and y represents 1 or 2, individually or as a mixture in fully or partially synthetic lubricants.
• the invention also relates to a lubricant which contains at least one polycarboxylic acid ester of the general formula (I).
• the radical X in the general formula (I) represents an arylene radical of the formulas
• the radical R in the general formula (I) has 9, 13 or 17 carbon atoms, it being particularly preferred if the mixtures are ester mixtures in which the radicals R have the meanings mentioned.
• the radical R in the general formula (I) particularly advantageously stems from the oxidation of a largely linearly oligomerized n-butene oligomer with a degree of oligomerization of 2 to 4.
• the polycarboxylic esters of the general formula (I) are particularly preferably phthalic esters or adipic esters with C9- and / or C13-oxo alcohols.
• the lubricants according to the invention contain at least one compound of the general formula (I).
• the lubricant can also contain other components, for example conventional components, for example base oils based on mineral oil or other synthetic lubricant components, for example poly- ⁇ -olefins.
• esters of the general formula I can be used either individually or as a mixture with one another.
• the polycarboxylic acid esters of the general formula I preferably have the nonyl and tridecyl radical as the monoalcohol component.
• the alcohols R-OH (nonyl or tridecyl alcohol) used in the esterification are mixtures of isomers as are obtained in the oxo synthesis of corresponding butene oligomers, namely octene and dodecene (butene dimer or butene trimer).
• lubricants for the engines of motor vehicles, compressor oils, hydraulic fluids, insulating fluids for electrical devices, electrical contact oils, lubricating greases, chain lubricants, heat transfer fluids, vacuum pump oils, synthetic fiber lubricants, instrument oils, rust protection oils and rolling oils . All applications in lubricants that have a lubricating function are the subject of the invention.
• the polycarboxylic esters according to the invention have a significantly better temperature-viscosity behavior than conventional esters, expressed by a significantly higher viscosity index.
• An essential requirement criterion for lubricating oils is the viscosity at low temperatures, i.e. e.g. at 0 to -30 ° C, as required in the lubricating oil specifications according to SAE J 300 (April 1984).
• DIN 51 377 (ASTM D 2606) serves as the measuring method for the low-temperature viscosity.
• the results from viscosity measurements for the esters according to the invention also show serious application advantages over conventional esters.
• esters according to the invention have a significantly higher flash point than esters which have been prepared from the oxo alcohols previously used.
• the esters are chemically more uniform than, for example, esters from oxo alcohols, based on conventional propylene tetramer (isododecene) .
• the esters according to the invention have lower evaporation losses (DIN 51 581) than conventional esters.
• the evaporation loss measured in accordance with DIN 51 581 is a further essential quality criterion for the suitability as a lubricant component in addition to the other basic technical data.
• olefin oligomers suitable for the oxo reaction are prepared by known processes. So you get e.g. n-butene dimers or n-butene trimers according to the teaching in EP-A-143 703, EP-A-012 685, EP-A-00 24 971 and DE-A-31 17 864.
• a technical mixture of C techn hydrocarbons (raffinate II, containing 60 to 80% n-butenes) is catalytically olgiomerized.
• the yield can be controlled depending on the process conditions.
• a butene oligomer is obtained which consists of 60 to 90% butene dimer (octene), 10 to 30% butene trimer (dodecene) and a corresponding residue of C 12+ oligomers.
• olgiomer fractions which are suitable for the preparation of oxoalcohols for esterification to the esters according to the invention: 1st fraction: boiling point 118-122 ° C (octene fraction) 2nd fraction: boiling point 200-220 ° C (dodecene fraction) Residue: boiling point above 230 ° C.
• the octene fraction is composed as follows: 55 to 60% methylheptene 5 to 7% n-octenes Balance dimethylhexenes.
• the invention is further illustrated by the examples below.
• the lubrication data of conventional esters are compared in each case with the data of the esters refined in the lubricant according to the invention.
• the di-isononyl adipate based on dimerbutene used according to the invention has a comparable flash point and evaporation loss, although it has two CH2 groups less.
• it has a significantly higher viscosity index and a significantly lower low-temperature viscosity than the well-known di-isodecyl adipate.

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)

Priority Applications (1)

Applications Claiming Priority (2)

Publications (3)

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ID=6311976

Family Applications (1)

Country Status (5)

Cited By (3)

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Family Cites Families (6)

• 1986
  • 1986-10-18 DE DE19863635490 patent/DE3635490A1/de not_active Withdrawn
• 1987
  • 1987-10-09 US US07/106,390 patent/US4790957A/en not_active Expired - Fee Related
  • 1987-10-15 CA CA000549377A patent/CA1276649C/fr not_active Expired - Lifetime
  • 1987-10-16 DE DE8787115127T patent/DE3766793D1/de not_active Expired - Lifetime
  • 1987-10-16 AT AT87115127T patent/ATE59202T1/de not_active IP Right Cessation
  • 1987-10-16 EP EP87115127A patent/EP0264842B1/fr not_active Expired - Lifetime

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