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
  • 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
  • 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
  • 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
  • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
• • 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
  • C10N2040/135—Steam engines or turbines
• • 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
  • C10N2040/25—Internal-combustion engines
• • 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
  • C10N2040/25—Internal-combustion engines
  • C10N2040/251—Alcohol fueled engines
• • 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
  • C10N2040/25—Internal-combustion engines
  • C10N2040/255—Gasoline engines
• • 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
  • C10N2040/25—Internal-combustion engines
  • C10N2040/255—Gasoline engines
  • C10N2040/28—Rotary engines
• • 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

• This invention relates to a synthetic ester base stock and, in particular, to a synthetic ester base stock formed from an acid mixture having a high content of branched chain acid, and a lubricant from the base stock having increased viscosity at elevated temperatures and a decreased tendency to form deposits in high temperature uses.
• Synthetic ester base stocks for use as chain oils and lubricants for gas turbine engines are well known.
• the base stocks are combined with standard lubricant additive packages to form the lubricant.
• the base stock In order for the lubricant to have properties suitable for such high temperature use, the base stock must have certain physical properties. For example, it is a requirement that the lubricant for turbine oils meet the specifications set forth in military specification MIL-L-23699D.
• Chain oils should have low deposition properties at high temperatures, a viscosity of at least about 7.0 centistockes (cSt) and a reasonably low pour point below its ambient storage temperature.
• esters In general, synthetic high temperature lubricants use esters as a base stock.
• the esters are formed by reacting a polyol, such as pentaerythritol, either monopentaerythritol (MPE) and/or dipentaerythritol (DPE) or trimethylolpropane (TMP) with various acids, both straight chain and branched.
• MPE monopentaerythritol
• DPE dipentaerythritol
• TMP trimethylolpropane
• Japanese patent applications No. JP 55-105644 and No. 55-157537 disclose a neopentyl polyol ester of iso-C9 acid and a straight chain saturated acid having from 4 to 18 and 2-24 carbon atoms, respectively, preferably 6 to 14 carbon atoms for air compressor oils.
• U.S. Patent No. 3,694,382 issued to Kleiman, et al. on September 26, 1972, discloses an ester blend for use as a synthetic lubricant.
• the ester blend includes esters of trimethylolpropane and dipentaerythritol formed from a mixture of aliphatic monocarboxylic acids.
• a jet engine oil consisting of an ester of a C4-C12 monocarboxylic acid, a polyol selected from pentaerythritol, dipentaerythritol, tripentaerythritol, trimethylolpropane, trimethylolmethane, trimethylolbutane, neopentylglycol and mixtures thereof and a soluble methyl phen
• U.S. Patent No. 3,360,465 issued to Warman on December 26, 1967, discloses synthetic ester lubricant compositions of pentaerythritol mixed esters.
• the pentaerythritol utilized includes at least 1.5 weight percent dipentaerythritol.
• the acid includes a mixture of from two to six monocarboxylic alkanoic acids having from five to nine carbon atoms with some of the lower acids being branched chain.
• Every lubricant has a characteristic tendency to form deposits when used in high temperature applications such as an engine or on industrial oven chains. If the deposits are excessive they will detract from the operating efficiency of the device and create other problems such as filter plugging in engines or track jumping of chains.
• an improved synthetic ester base stock is prepared by reacting at least one neopentyl polyol, with a monocarboxylic acid mixture including at least one C5-C10 normal alkanoic acid and between about 60 and 90 weight percent of C7-C10 branched chain acid, based on the total weight of the acid charged.
• the polyol may be a commercially available mono- or di-pentaerythritol, trimethylolpropane or neopentyl glycol.
• the straight chain monocarboxylic acids include those having between 5 and 10 carbon atoms, such as valeric acid (pentanoic acid), caproic acid (hexanoic acid), oenanthic acid (heptanoic acid), caprylic acid (octanoic acid), pelargonic acid (nonanoic acid), capric acid (decanoic acid) and mixtures thereof.
• the branched chain acid is preferably iso-C9 acid, iso-nonanoic acid.
• Another object of the invention is to provide an improved synthetic ester base stock having a decreased tendency to form deposits when used in a high temperature environment.
• a further object of the invention is to provide an improved synthetic ester base stock for high temperature applications and with a suitably higher viscosity.
• Yet another is to provide a synthetic ester base stock with higher oxidative stability.
• Still another object of the invention is to provide a synthetic ester base stock which when combined with a standard lubricant additive package provides a lubricant with a viscosity at 210° F. of at least about 7.0 centistokes and a pour point of less than at least about -10° F.
• the invention accordingly comprises a composition of matter possessing the characteristics, properties and the relation of components which will be exemplified in the composition hereinafter described, and the scope of the invention will be indicated in the claims.
• the synthetic lubricant base stock prepared in accordance with the invention is to be used with standard lubricant additive packages.
• the lubricant base stock is the reaction product of a neopentyl polyol and a monocarboxylic acid mixture having a high branched chain acid content, preferably between about 60-90 weight percent of a branched chain acid, based on the total acid charge.
• the lubricant has a viscosity at 210° F. of at least about 7.0 centistokes and a pour point of less than about -10° F.
• the acid component is monocarboxylic and includes at least one straight chain acid having 5 to 10 carbon atoms and a branched chain acid having from 7 to 10 carbon atoms.
• the branched chain acid preferably has nine carbon atoms, namely, iso-nonanoic acid.
• Suitable straight chain acids include, but are not limited to, valeric acid, oneanthic acid, caprylic acid, pelargonic acid and capric acid.
• the straight chain acid component is valeric (C5) or is a mixture of heptanoic (C7) and caprylic-capric (C8-C10).
• the caprylic-capric acid is identified as having between 8 and 10 carbon atoms, but actually includes C6 to C12 acids and is substantially free of C12 acid (less than 1%).
• the amount of the preferred heptanoic and caprilic-capric mixture straight chain acid component suitable for use in preparing esters in accordance with the invention may vary widely.
• the mixture may be from about 30 to 70 weight percent heptanoic acid and the balance the caprylic-capric mixture.
• the normal acid mixture is about 40-60 parts by weight of heptanoic acid and the balance caprylic-capric acids.
• the branched chain acid may be iso-C7 acid, iso-C8 acid, iso-C9 acid or iso-C10 acid.
• iso-C9 or iso-nonanoic acid is 3,5,5-trimethylhexanoic acid and has the formula: Addition of the iso-nonanoic acid provides the necessary viscosity characteristics and improves the pour point characteristics of the base stock and improves the oxidative stability and deposition tendency.
• the iso-acids other than iso-nonanoic can be used to provide base stocks which are suitable for turbine engine or chain lubricant applications.
• iso-C7, iso-C8 and iso-C10 acids are available, but these acids contain a complex mixture of isomers, unlike iso-C9 acid which is mainly 3,5,5-trimethylhexanoic acid.
• the physical properties of an acid that is a complex mixture of isomers can change if the relative ratios of the isomeric components change and this affects the properties of an ester produced from the acid. Therefore, to produce a consistent ester product, it is preferable to use raw materials that consist of a single, high purity component, namely, iso-C9 or iso-nonanoic acid.
• the acid mixture is present in the reaction in an excess of about 5 to 10 weight percent for the amount of the polyol mixture used.
• the excess acid is used to force the reaction to completion.
• the excess acid is not critical to carrying out the reaction except that the smaller the excess, the longer the reaction time.
• the excess acid is removed by stripping and refining.
• the esterification reaction is carried out in the presence of conventional catalysts.
• a tin or titanium based catalyst of such a catalyst may be used. Tin oxalate is an example.
• Lubricants including ester base stocks prepared in accordance with the invention are prepared by mixing a conventional additive package to the base stocks in conventional concentrations.
• Typical additive packages are described in U.S. Patent Nos. 4,124,513, 4,141,845 and 4,440,657.
• the two former patents describe additive packages based on an alkylphenyl or alkarylphenyl naphthylamine, a dialkyldiphenylamine, a polyhydroxy anthraquinone, a hydrocarbyl phosphate ester with an S-alkyl-2-mercaptobenzotriazole or an N-(alkyl)-benzothiazole-2-thione.
• the third patent describes additives of a selected tertiarybutylphenyl substitute phosphate and a selected alkyl amine.
• ester base stocks were prepared.
• the raw materials identified in the Table and a tin oxalate catalyst were charged to a stirred reactor capable of attaining 460°-490° F. and a vacuum of at least 29 inches of mercury.
• the reactor was provided with a nitrogen sparge or blanket.
• the charge was heated to a reaction temperature between about 440° and 450° F. and the water of reaction was collected in a trap while the acids were returned to the reactor.
• vacuum was applied in order to maintain a reasonable reflux rate.
• the hydroxyl value was reduced to a sufficiently low level (a maximum of 5.0 mg KOH/gm)
• the bulk of the excess acid was removed by distillation at the reaction temperature and maximum vacuum.
• the residual acidity was removed by treatment with lime and water.
• the resulting ester base stock was dried and filtered.
• the viscosity at 210° F. was determined in accordance with ASTM D-445 for each sample base stock together with the pour point in accordance with ASTM D-97.
• Lubricants prepared in accordance with the invention have a decreased tendency to form deposits when used in high temperature applications. This reduced tendency was demonstrated by mixing base stock with an additive package as follows: This additive package was selected as the standard package for comparing base stocks in the panel test.
• a stainless steel panel is electrically heated by means of two heaters which are inserted into holes in the panel. The temperature is monitored by means of a thermocouple. The panel is placed on a slight incline and heated to 540° F. The lubricant to be tested is dropped onto the heated panel and the characteristics are observed. The lubricant contacts the panel near the top of the incline and is observed as a central dark band. The lubricant then tends to thin out as it travels towards the lower end of the heated panel. It is along the oil-air-metal interface that the degradation of the lubricant is best observed.
• compositions prepared in accordance with the composition of Run 1-4 of the Example showed little degradation along the oil-air-metal interface.
• These lubricants are an ester mixture formed by reacting technical grade pentaerythritol or dipentaerythritol with an acid mixture including valeric or heptanoic and capric-caprilic as the normal acid and iso-nonanoic acids.
• Runs 5-7 were lubricants formed from base stocks prepared by reacting technical grade PE or MPE and dodecanoic acid consistent with Runs 5 and 6 of Example 1 in JP 55-105644.
• the panel test results for a lubricant made from these esters formed from decanoic acid showed significantly increased carbonization along the oil-air-metal interface compared to Runs 1-4.
• ester lubricants having improved properties may be obtained.
• the lubricants have improved oxidation stability with lower depositing tendency at high temperatures, a viscosity at 210°F of at least about 7.0 cSt and improved pour points.
• the iso-acid is iso-C9 acid and is present from 60 to 90 weight percent of the total acid charge.
• the straight chain acid will be present from 10 to 40 weight percent of the acid charge which maintains good pour point characteristics and an improved viscosity index.
• linear acids above C10 are used, the resulting esters tend to crystallize at ambient temperatures. When linear acids having less than five carbon atoms are used, odor and corrosion problems arise.
• ingredients or compounds recited in the singular are intended to include compatible mixtures of such ingredients wherever the sense permits.

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Chemistry (AREA)
• Lubricants (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (8)

• 1992
  • 1992-06-05 EP EP92305169A patent/EP0518567B1/de not_active Expired - Lifetime
  • 1992-06-05 DE DE69231433T patent/DE69231433T2/de not_active Expired - Lifetime
  • 1992-06-08 JP JP4173790A patent/JPH0665587A/ja active Pending

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