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  • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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  • C10M2207/28—Esters
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
  • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/064—Di- and triaryl amines
  • C10M2215/065—Phenyl-Naphthyl amines
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
  • C10M2219/108—Phenothiazine
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  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
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  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/042—Metal salts thereof
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  • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
  • C10M2229/02—Unspecified siloxanes; Silicones
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  • C10M2229/04—Siloxanes with specific structure
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  • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
  • C10N2020/01—Physico-chemical properties
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  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
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  • C10N2040/00—Specified use or application for which the lubricating composition is intended
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  • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
  • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

• This invention relates to alcohol esters of aromatic polycarboxylic acids and to lubricating oil compositions containing said esters. Particularly, it relates to synthethic esters prepared from mono or dihydric alcohols and aromatic acids having 3 to 4 carboxylic groups per molecule, which esters are useful as synthetic lubricating oils and as oil additive materials.
• the load-carrying ability of the aliphatic ester oils is not particularly high. Because of the increasing severity of the conditions prevailing in the lubricaton of aviation gas-turbine systems, it is highly desirable to form synthetic ester lubricating compositions having higher load-carrying ability than is now generally available, and yet at the same time being noncorrosive. It has now been found that aromatic triand tetra-carboxylic acids, when fully esterified with aliphatic hydroxy materials, form esters which have extremely high load-carrying ability and also tend to inhibit corrosion of lead-containing bearings frequently used in aircraft engines. In addition, these aromatic esters have many of the properties which have made the aliphatic esters (e.g.
• the tetraesters of the invention particularly when branched, have low pour points, good viscositytemperature relationship, high flash points, and are unusually thermally stable. Furthermore, these esters have much lower coking values than many of the aliphatic esters used as lubricants and often have much lower evaporation losses and generally speaking are useful as lubricants per se. It has been further found that when the tetraesters of the invention are used in mineral oil crankcase lubricants that they have a marked tendency to reduce engine deposits.
• the partial esters of the invention have many of the properties of the tetraesters, particularly With regard to inhibiting lead corrosion and imparting load-carrying ability. However, since the parital esters generally have rather high pour points, they are best used blended with other oils.
• esters of the invention include mono-, di-, t-ri-, and tetraesters having the general formula:
• R represents an aromatic nucleus having 6 carbon atoms in the ring
• R is an alkyl radical containing about 3 to about 20, e.g. 5 to 13, carbon atoms
• n is a number of l to 4
• aromatic polycarboxylic acids used in preparing the above type of esters include the following:
• Esters may also be prepared from the corresponding cycloheXane polycarboxylic acids that result when the aromatic acid is catalytic hydrogenated to saturate the ring.
• the esters of the invention are preferably prepared from pyromellitic acid or its anhydride since it is readily available in commercial quantities and undergoes esterification very readily.
• Preferred alcohols for forming the ester are those alkanols of about 3 to about 20, e.g. 5 to 10 carbon atoms. These alcohols may be either straight chain or branched chain alcohols. Primary alcohols are particularly preferred. Secondary and tertiary alcohols, while operable, are less preferred for the purposes of this invention, since esters prepared from such alcohols generally have poorer thermal stability than the corresponding esters prepared from primary alcohols.
• n-decyl alcohol n-octyl alcohol
• n-heptyl alcohol n-hexyl alcohol
• n-amyl alcohol n-butyl alcohol
• Fischer- Tropsch synthesis alcohols Operable branched chain primary alcohols include 2-ethylhexyl alcohol, 2-ethylbutyl alcohol, and the Oxo alcohols. These Oxo alcohols are Well known in the art. They are prepared in a two 3 stage reaction.
• the first stage involves reacting olefins, such as polymers and copolymers of C and C monoolefins, with carbon monoxide and hydrogen at temperatures about 300 F. to 400 F. and pressures of about 30 to 400 atmospheres, in the presence of a suitable catalyst, ordinarily a heavy metal carbonyl, such as cobalt carbOnyl, to form a mixture of aldehydes having one carbon atom more than the olefin.
• a suitable catalyst ordinarily a heavy metal carbonyl, such as cobalt carbOnyl
• the aldehyde mixture is hydrogenated, to form an isomeric mixture of highly branched chain primary alcohols which is recovered by distillation.
• the process is Well known and has been described in various US. Patents, e.g. US. 2,327,066 and US. 2,593,428.
• the aromatic acid esters of the invention are prepared by conventional esterification techniques.
• the esterification is carried out by reacting l to 4 molar proportions of an alcohol (depending upon whether a full or partial ester is desired) per one molarproportion of the aromatic acid, under reflux conditions.
• a water-entraining agent e.g. heptane, toluene, etc.
• Esterification catalysts may be used, e.g.
• reaction may be carried out without a catalyst.
• the remaining reaction product may be filtered and washed, if a catalyst was used, and distilled under vacuum in order to remove the entraining agent and any un'reacted alcohol.
• the resulting ester product may be used as a lubricant per se or it can be advantageously blended in any proportions with other lubricating oils.
• such blends may contain for example, about 0.25 to 90, preferably 0.25 to 70, weight percent of the aromatic acid ester and about 99.5 to 10, preferably 99.5 to 30 weight percent of another lubricating oil.
• the lubricating oil used with the aromatic acid esters may be a mineral lubricating oil, a syn thetic lubricating oil, or any mixtures thereof.
• Particularly preferred synthetic oils for blending with the aromatic acid ester materials are the saturated aliphatic diesters represented by the formula:
• R is a straight or branched chain hydrocarbon radical of a C to C alkandioic acid, while R represents an alkyl radical of a C to C branched or straight chain alkanol, and the total number of carbon atoms in the molecule being twenty or more.
• diesters include di(2-ethylhexyl)sebacate, C Oxo alcohol ester of C Oxo acid, di(C Oxo)adipate, etc.
• Other synthetic oils which may be used will include esters of monobasic acids (e.g. C OX alcohol ester of C Oxo acid), esters of glycols (e.g. C Oxo acid diester of tetraethylene glycol), complex esters, esters of phosphoric acid, halocarbon oils, sulfite esters, silicone oils, carbonates, formals, polyglycol-type synthetic oils, etc.
• additives may also be added to the lubricating compositions of the invention in amounts of about 0.1 to 10.0 weight percent, based on the total weight of the composition.
• detergents such as calcium petroleum sulfonate; oxidation inhibitors such as phenylalpha-napthylamine or phenolthiazine; corrosion inhibitors such as sorbitan monooleate; pour point depressants; dyes; grease thickeners; load-carrying agents and the like may be added.
• the piston underside demerit in the Homelite test is a measure of this; demerits of 2.0 or greater indicating the oil would give copious intake valve deposits while demerits of 1.0 or less are obtained with oils that would give satisfactory car performance in this respect.
• the test also gives a general indication of the detergency of the oil (i.e. its ability to prevent ring sticking and heavy varnish formation).
• EXAMPLE II OX) adipate and a di-(C Oxo) adipate containing 1 weight percent of phenothiazine as an oxidation inhibitor. Since synthetic oils are frequently used to lubricate lead-containing bearings, the resulting blends were tested for lead corrosion. This test was carried out by rapidly rotating a bimetallic strip consisting of a lead strip and a copper strip bound together, in an oil sample maintained at 325 F. while air is bubbled through the sample. The weight loss of the lead strip is then determined, and reported in terms of mg. wt. loss per square inch of lead surface. Lubricants possessing very low lead corrosion are desired for aircraft engine lubrication. The blends were also tested for load-carrying ability in the Ryder Gear Test in accordance with MIL-7808C specification procedures.
• adipate base oil consisted of 1 weight percent of phenothiazine and 99 weight percent of a 50/50 (by volume) blend of 08 0x0 adipate and C 0x0 adipate.
• the Oxo portion of the adipates were derived from Oxo alcohols prepared from a C -C olefin feed.
• the 0X0 adipate-PMDA half ester-phenothiazine blends were further tested for corrosiveness to copper, magnesium, iron, aluminum and silver and for changes in viscosity and acidity. These tests were carried out in accordance with MILL-7808C specification procedure, i.e., by immersing weighed strips of the metal to be tested in 100 cc. of the sample maintained at 347 F. for 72 hours while bubbling 0.5 liter per hour of air through the sample. The metal strip is then reweighed to determine the weight change as mg./cm. and the change in viscosity and neutralization number of the composition is determined. The results of these tests are summarized in Table III which follows:
• a series of tetra esters of pyromellitic anhydride were prepared in the general manner of Example I. These esters were prepared from amyl alcohol, C Oxo alcohol (prepared from copolymer of propylene and butylene), C OX0 alcohol (prepared from tripropylene), and C Oxo alcohol (prepared from tetrapropylene).
• the amyl alcohol was prepared using para-toluene sulfonic acid as the catalyst, while the 0x0 alcohol esters were prepared using sodium hydrogen sulfate as the catalyst. After completion of the reaction, the catalysts were removed by filtration.
• a composition consisting of 100 parts by weight of tetra-C OX0 pyromellitate and 1 part by weight of phenothiazine as oxidation inhibitor was tested in a Bearing Ring Test under conditions similar to those encountered in the lubrication of the bearings supporting the rotor shaft of a Pratt and Whitney J-57 turbo-jet engine.
• -a 100 mm. dia. aircraft steel roller bearing rotating at 10,000 rpm. is maintained at a temperature of 350 F., while being sprayed with a jet of the oil composition heated to 250 F., at the rate of 500 cc. of oil per minute.
• EXAMPLE IV 25 wt. percent of amyl tetra pyromellitate was mixed with 75 wt. percent of a paraflinic mineral lubricating oil having a viscosity of 10 cs. at 210 R, and a viscosity index of 106. The blend was then tested for load-carrying ability in the Ryder gear test. The results of these tests are summarized in the following table along with similar data on the pyromellitate alone and the mineral oil alone:
• EXAMPLE V A quarter, or monoester was prepared by reacting 1 molar amount C Oxo alcohol with 1 molar amount of pyromellitic dianhydride. This ester was prepared in the general manner of Example I, but no catalyst was Load-carrying ability:
• This diester base lubricant in turn, consisted of 97.0 parts by Weight of di(C Oxo)azelate; 3 parts by Weight of a complex ester prepared by simultaneously reacting 1 mole of polyethylene glycol of 200 mol. wt., 2 moles of C OX alcohol and 2 moles of adipic acid; 4 parts by weight of a dimethyl silicone oil having 10 cs.
• the invention relates to lubricating oil compositions comprising alkyl esters of polycarboxylic aromatic acids having 3 to 4 carboxy groups per molecule and wherein the alkyl radicals each contain 3 to 20, preferably to 13 carbon atoms. Esters of pyromellitic acid are preferred and may be prepared either from the acid or its anhydride.
• the normally liquid tetraesters of pyromellitic acid are suitable as lubricating oils per se, or can be blended in any proportion with other lubricating oils.
• the partial esters of pyromellitic acid are frequently solids or near solids at room temperature, as are certain of the straight chain higher alkyl tetraesters, tag. the straight chain tetra octyl pyromellitate which melts at about 90 F. Such materials are best used in minor ,amounts as additives for lubricating oils to impart El.
• a lubricating oil composition suitable for lubrication of aircraft engines comprising a major amount of a synthetic aliphatic ester lubricating oil and about 0.25 to 10% by weight of a partial ester selected from the group consisting or" monoalkyl pyromellitate and dialkyl pyromellitate, wherein said alkyl groups are alkyl groups of C to C alcohols.
• a lubricating oil composition comprising a major amount of a saturated diester of a C to C alkandioic acid and a C to C alkanol, said diester being normally corrosive to lead, and a lead corrosion inhibiting amount, within the range of about 0.25 to 10.0 wt. percent, of dialkyl pyromellitate, wherein said alkyl group contains 5 to 10 carbon atoms.
• a lubricating oil composition comprising a major amount of saturated diester of a C to C alkandioic acid and a C to C alkanol, said diester being normally corrosive to lead, and a lead corrosion inhibiting amount, within the range of about 0.25 to 10.0 wt. percent, of monoalkyl pyromellitate, wherein said alkyl group contains 5 to 10 carbon atoms.

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• Oil, Petroleum & Natural Gas (AREA)
• Organic Chemistry (AREA)
• Lubricants (AREA)

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