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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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  • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
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  • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
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  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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  • C10M2205/026—Butene
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  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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  • C10M2207/02—Hydroxy compounds
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  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/028—Overbased salts thereof
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
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  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/084—Acrylate; Methacrylate
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  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
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  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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  • C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
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  • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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  • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
  • C10M2215/28—Amides; Imides
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  • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
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  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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  • 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
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  • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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Definitions

• oils containing certain of the esters, particular bis-alkylene esters, and certain of the dithiacyclopentylidene benzenes and mixtures thereof demonstrate superior extreme pressure lubricating properties.
• This invention relates to compounds useful as additives for lubricating oil compositions, to intermediates for such compounds, to processes for preparing these compounds, and to lubricating oil compositions containing such compounds.
• Lubricating oils are employed in a host of environments. Under most conditions of use, the oil comes into contact with air, often at elevated temperatures and in the presence of metals or chemical compounds which act as oxidation catalysts. Lubricating oils, whether natural or synthetic, when exposed to such conditions, undergo a series of oxidation reactions. The deleterious efiects of such oxidation includes an increase in viscosity, formation of carbonaceous matter and the production of various oxygen-containing contaminants.
• the contaminants have been found to include lactones, ketones, aldehydes, esters, alcohols, hydroxy acids, anhydrides, and peroxides.
• the acidic and peroxidic contaminants attack metals, corrode bearings, and promote rust and wear.
• Acidic contaminants are also a major source of the oil insolubles that cause ring sticking and sludging, and impede oil flow.
• Antioxidants are incorporated in lubricating oils to retard such oxidation of the oil.
• phenols known as hindered phenols are said to inhibit oxidational changes in petroleum hydrocarbon products, when incorporated therein in small amounts.
• Humphreys et al. US. Pat. 2,073,841, issued Mar. 16, 1937, describes extreme pressure lubricating compositions containing esters and anhydrides of organic thio acids. Useful compounds are said to include s-ethyl thiobenzoate and benyl thiobenzoate.
• organic compositions such as lubricating oils and fuel oils containing secondary trialkyl phenols in which the secondary alkyl groups contain from 6 to 9 carbon atoms.
• the phenols are described as antioxidants for the organic compositions.
• the compounds of this invention comprise esters of 4-hydroxy and 4-thiol benzoic acids, dithio; 1,4dihydrol-oxo-4-dithiomethylenebenzenes and 1,4-dihydro-l-oxo- 4-(1,3-dithiacyclopent-Z-ylidene)benzenes having nuclear alkyl substituents in both positions ortho to the hydroxy, thiol, and oxo groups which sterically hinder these groups.
• These compounds are useful as additives for lubricating oil compositions.
• the presence of these additives provides antioxidation protection for the oil and, in many cases, additionally confers extreme pressure lubricating properties to the oil.
• esters and substituted benzenes of this invention are derived from 4-hydroxy and 4-thiol benzoic acids, dithio.
• the benzoic acid moiety is substituted in both positions ortho to the hydroxy and thiol groups with alkyl substituents which sterically hinder the hydroxy and thiol groups.
• alkyl substituents have four or more carbon atoms and are generally branched rather than straight chain, e.g., t-butyl, t-amyl and the like.
• Preferred compounds of the invention include esters of 4-hydroxy and 4-thiol benzoic acids, dithio having the following formulae:
• R and R each represent an alkyl group, which sterically hinders the adjacent hydroxy, thiol, or x0 group, containing four or more carbon atoms, desirably four to nine carbon atoms in a branched chain, such as t-butyl, t-amyl, s-hexyl, s-heptyl, s-octyl, s-nonyl and the like;
• R R and R each represent alkyl containing from 1 to 20 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, tert-amyl, hexyl, heptyl, octyl, nonyl, dccyl, dodecyl, pentadecyl, eicosyl and the like; hydroxyalkyl, e.g., --R-OH, hydroxyalkyloxyalkyl, e.g.,
• alkylene moieties represented by R contain 2 to 5 carbon atoms and can be straight or branched chain such as ethylene, 1,2-propylene, 1,2-butylene, 1,2-pentylene and the like and n represent 2 to 6; aralkyl such as benzyl, p-xylyl, and the like; or aryl such as phenyl, 4-tolyl and the like;
• R represents an alkylene group containing from 1 to 8 carbon atoms such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, and the like;
• Each R represents hydrogen, alkyl such as defined above for R or aryl such as phenyl, tolyl, xylyl and the like, and preferably R represents hydrogen;
• X represents oxygen or sulfur and preferably oxygen
• Y represents hydrogen or a metallic cation such as those derived from alkali metal such as sodium and potassium and those derived from alkali earth metals such as calcium and barium; preferably Y represents hydrogen.
• esters of benzoic acid, dithio contemplated by the invention are the following typical compounds:
• Preferred intermediates of this invention include 4-thiol and 4-hydroxybenzoic acids having the following formula:
• processes are provided for preparing the above-described 4-thiol and 4-hydroxybenzoic acid, dithio, intermediates which comprise combining about one equivalent of a phenol or thiophenol having nuclear alkyl substituents in both positions ortho to the hydroxy or thiol group which sterically hinder the hydroxy or thiol group with about two ventiom r equivalents of a strong proton acceptor to obtain a first reaction product.
• This first product is then combined with about one equivalent of carbon disulfide to yield the intermediate as a dithiobenzoic acid radical.
• This acid radical is probably in the form of the double salt of the cation of the proton acceptor.
• the dithiobenzoic acid can be recovered, if desired, by acidifying the reaction mixture with at least two equivalents of a proton donor such as a mineral acid to yield the dithiobenzoic acid in free acid form.
• a proton donor such as a mineral acid
• the term strong proton acceptor refers to a moiety capable of extracting a proton from the para position of the sterically hindered phenols and thiophenols used to prepare the intermediates described above and shown in Formula V.
• Such proton acceptors include alkali metal hydroxides such as sodium and potassium hydroxide, alkali metal alkoxides such as sodium and po' tassium methoxide and ethoxide and alkali metal amides such as sodium and potassium amide.
• the above process is preferably carried out in a solvent medium under an inert atmosphere.
• the solvent can be any inert solvent which does not interfere with the desired reactions.
• the solvents can be polar as well as non-polar. Generally, mixtures of polar and non-polar solvents are used in order to obtain at least partial miscibility of the various reactants. For example, a mixture of water, dimethyl sulfoxide and pentane, hexane or heptane is conveniently used.
• the inert atmosphere can be any atmosphere which does not interfere with the reaction. It is most conveniently nitrogen.
• the reactions are carried out at low to moderate temperatures, e.g., from about 0 C. to about 50 C. and preferably from about 10 C. to about 40 C.
• processes are provided for preparing the esters of dithiobenzoic acid and the substituted benzenes described above and exemplified in Formulas I-IV. These processes comprise combining the dithiobenzoic acid intermediate described above in its radical form with zero to one equivalent of a proton donor to obtain a third reaction product. This third reaction product is then combined with a two to one-half equivalents of a precursor of the desired thio substituent.
• the quantity of proton donor with which the intermediate radical is combined is determined by the product desired. If the product desired is of the diester type represented by Formula III above or the cyclopentylidenebenzene of Formula IV above, the intermediate is not reacted with the proton donor. This double salt is thereby free to react with two equivalents of the precursor of the thio substituents. The precursor has only one reactive site or one equivalent if it has two reactive sites. If the. product is of the mono ester of the type represented byFormulas I and 11 above, then the intermediate is combined with one equivalent of the proton donor.
• This product is then free to react with one equivalent of thio substituent precursor if such precursor has one reactive site or one-half equivalent if the precursor has two reactive sites as in the case of the dihaloalkanes from which the. compounds of Formula II are prepared.
• thio substituent precursor if such precursor has one reactive site or one-half equivalent if the precursor has two reactive sites as in the case of the dihaloalkanes from which the. compounds of Formula II are prepared.
• the precursor is a dihaloalkane wherein the halo substituents are on adjacent carbon atoms.
• proton donor refers to a moiety capable of donating a proton to the thiobenzoic acid radical.
• These proton donors are conveniently strong mineral acids such as hydrochloric acid, sulfuric acid and nitric acid.
• the precursors of the thio substituent are alkanes, hydroxyalkanes, hydroxyalkyloxyalkanes, hydroxyalkyl poly (oxalkyl) oxyalkanes and aralkanes substituted with at least one moiety which causes them to be reactive toward the dithiobenzoic acid radical.
• these substituents are halogen and preferably chlorine.
• the precursors are substituted with one halo group except for those precursors used to prepare the esters of Formula II and the dithiacyclopent-Z-ylidenebenzenes.
• the precursors for these two types of compounds contain two halo substituents.
• the process of adding the proton donor to the dithiobenzoic acid radical can be carried out at varying temperatures; however, room temperature is quite convenient.
• the process of esterifying the dithiobenzoic acid radical with the thio substituent precursor can also be carried 7 out over a wide temperature range suitably ranging from about room temperature up to about 100 C. or greater.
• the reaction is carried out by combining the dithiobenzoic acid radical and the thio substituent precursor at about room temperature and heating the reaction mixture with stirring to about 50 to about C.
• the time required for the reaction to proceed to completion can vary widely depending upon temperatures, concentrations, etc. Typically, the reaction will proceed to completion within about one to five hours when carried out in preferred temperature range.
• lubricating oil compositions comprising a major amount of an oil of lubricating viscosity and an effective amount of a compound selected from the class consisting of esters of 4-hydroxybenzoic acids, dithio; esters of 4-thiolbenzoic acids, dithio; 1,4-dihydro-1-oxo 4 dithiomethylenebenzenes and 1,4- dihydrol-oxo-4 (1,3-dithiacyclopent-2 y1idene)benzenes in which the esters and benzenes have nuclear alkyl substituents in both positions ortho to the hydroxy, thiol, or x0 groups which sterically hinder such groups.
• the lubricating oil compositions of this invention comprise a major amount of an oil of lubricating viscosity and an effective amount of one or more of the compounds of Formulas IIV.
• esters and benzenes are present in the lubricating oil composition in an amount effective to impart the desired antioxidation and extreme pressure lubrication properties. This amount can range from about 0.1 percent weight to about percent weight of the total oil composition and generally from about 0.5 percent weight to about 3 percent weight of the total oil composition.
• solutions of the esters and benzenes in oil are more readily obtained when the groups represented by R R and R in the above formulae are oleophilic in nature, e.g., have medium length or longer alkyl chains such as octyl, decyl, dodecyl eicosyl, and the like or have a higher number of oxyalkyl units in the hydroxalkyl poly(oxyalkyl) chain.
• these compounds may be diflicult to dissolve in the oil and occasionally may crystallize out of the oil.
• crystallinity problems generally are readily overcome by using a mixture of hydroxyalkyls having a varying number oxyalkyl units in the chain such as a mixture of esters having about one-half each of a hydroxyalkyloxyalkyl and a hydroxyalkyl-di-oxyalkyl substituent.
• esters and benzenes can be added to the oil singly or in mixtures.
• a mixture of two or more esters can be used.
• a mixture of two or more benzenes or a mixture of esters and benzenes can be used.
• the benzenes are, in a sense, a double esterification product obtained from the synthesis of the ester. Often varying quantities of esters of benzenes are produced as impurities during the synthesis of the other type of compound. It is generally most convenient to simply use the mixture obtained without attempting a separation of the compounds.
• the other additives can be present in varying amounts. Usually, for oils to be used in an engine, the total amount of these additives will range from about 0.1 to 15 weight percent and more usually from about 0.5 to 10 weight percent. The individual additives may vary in amount from about 0.01 to 10 percent weight of the total composition.
• additives include ashless dispersants such as succinimides, hydrocarbyl alkylene polyamines, etc., corrosion inhibitors such as metal dithiophosphates, etc., detergents such as the sulfonates, phosphonates, phenates, etc., viscosity index improvers such as the polyisobutylenes, polyacrylates, etc., pour point depressants such as the polymethacrylates, polyacrylamides, etc., extreme pressure additives, and other additives designed to accomplish specific objectives.
• ashless dispersants such as succinimides, hydrocarbyl alkylene polyamines, etc.
• corrosion inhibitors such as metal dithiophosphates, etc.
• detergents such as the sulfonates, phosphonates, phenates, etc.
• viscosity index improvers such as the polyisobutylenes, polyacrylates, etc.
• pour point depressants such as the polymethacrylates, polyacrylamides, etc.,
• oils which find use in this invention are oils of lubricating viscosity derived from petroleum or synthetic sources.
• the oils can be paraffinic, esters, naphthenic, halo-substituted hydrocarbons, asphaltic or combinations thereof.
• Oils of lubricating viscosity normally have viscosities in the range of 35 to 50,000 Saybolt Universal Seconds (SUS) at 100 F. and more usually from about 50 to 10,000 SUS at 100 F.
• the viscosity of the oil is measured at the start of the test and at the end of the l0-hour period. The increase is reported as a percentage of the original value.
• Table I reports the values obtained from subjecting a variety of oil compositions to the Oxidator B test. The amount of each additive used is expressed as percent weight of the total composition.
• the oil used in these tests is a solvent refined neutral hydrocarbon oil having a viscosity of 480 Saybolt Universals Seconds at F. (38 C.).
• A 2,2-bls(l-hydroxy-i-polypropylenephenyl)disulflde 75 percent weight in oil.
• B air-bis(l-hydroxy-c-methyl-4-polypropyienepheny0disuifide, 76 percent weight in o
• C A polyisobutenylsucclnimide produced by reacting a succinic anhydrlde of a polybutene (PIBSA 950) having a number average molecular weight of about 950 with tetraethylenepentamine (TEPA) at a mole ratio of TEPA to PIBSA of 0.87, approximately 44 percent weight active additive in oil solution.
• PIBSA 950 polyisobutenylsucclnimide produced by reacting a succinic anhydrlde of a polybutene (PIBSA 950) having a number average molecular weight of about 950 with tetraethylenepentamine (TEPA) at a mole ratio of TEPA to
• E 99.3 percent weight of a pol sobutenylsuccinimide similar to that of Compound 0 except that succinic anhy ride oi a polybutene (PIBSA 640) having a number average molecular weight oi. about 640 is used to reduce the mole ratio oi TEPA to total PIB SA to 0.50, and 0.7 Eercent weight of terephthalic acid.
• PIBSA 640 polybutene having a number average molecular weight oi. about 640 is used to reduce the mole ratio oi TEPA to total PIB SA to 0.50, and 0.7 Eercent weight of terephthalic acid.
• F Bis(3,5-di-t-butyl-4-hydroxyp enyDmethylene-au antioxidant currently in commercial use and used as a reference in the above tests.
• V-block and pin test specimens are immersed in a vessel of test lubricant at a preselected temperature.
• the machine is Q2%? 6 $ ⁇ :f g figg ifgg lggggggfifs figgfggg i fi g 3 352 3 operated at 290 r.p.m. and the specimens are broken in usedln these tests. Seizure did not occur under maximum loading.
• Additives are expressed as percent weight of the total oil composition.
• Additive F Same as E except does not contain terephthalic acid.
• EXAMPLE III-BEARING CORROSION TEST In addition to conferring beneficial properties to lubrieating oils, additives must not cause certain harmful effects.
• One harmful effect to be avoided is corrosion of engine parts, particularly the nonferrous parts which come in contact with the oil. Corrosion of this nature caused by a particular additive is measured by immersing separate strips of lead and copper in the oil composition to be tested and maintaining the 'oil at a temperature of 295 F. (146 C.) for 20 hours. Both strips are weighed to determine weight loss.
• the copper strip is washed with potassium cyanide solution to remove copper compound deposits and re-weighed.
• Table HI The results of testing several additive combinations of the invention are shown below in Table HI.
• the base oil used is the same 480 SUS neutral oil used in the above examples.
• the solid product obtained is dissolved in a mixed hexanes solvent to produce a saturated solution.
• the solution is chilled in a refrigerator overnight.
• the mother liquor is decantered from the crystals obtained and the crystals are taken up in 750 m1. of mixed hexanes.
• the volume of the second solultion is reduced to about half and cooled to obtain crystallization.
• the crystals thus obtained are suitable for use as a lubricating oil additive.
• reaction mixture is placed in a separatory funnel and the organic phase is removed. Distilled water (500 ml.) is added to the remaining aqueous phase, which is then extracted three times with Chevron Thinner 250* (600 ml.). The combined organic phases are washed three times with water (700 ml.) and are dried over anhydrous sodium sulphate. The organic phase is filtered and the volatiles are removed under vacuum on a rotary evaporator to yield 73.4 g. of product suitable for use without further purification.
• Distilled water 500 ml.
• Chevron Thinner 250* 600 ml.
• the combined organic phases are washed three times with water (700 ml.) and are dried over anhydrous sodium sulphate.
• the organic phase is filtered and the volatiles are removed under vacuum on a rotary evaporator to yield 73.4 g. of product suitable for use without further purification.
• a lubricating oil composition comprising:
• R and R each represent an alkyl group which sterically hinders the adjacent hydroxy, thiol or 0x0 group;
• R R and R each represent alkyl, hydroxyalkyl, hydroxyalkyloxyalkyl, hydroxyalkylpoly- (oxyalkyl), aralkyl or aryl;
• R represents an alkylene group
• each R represents hydrogen, alkyl or aryl
• X represents oxygen or sulfur
• Y represents hydrogen or a metallic cation selected from alkali metal and alkaline earth metal cations.
• a lubricating oil composition of claim 1 wherein:
• R and R each represent a branched alkyl containing from 4 to 10 carbon atoms
• R R and R each represent alkyl containing from 1 to 20 carbon atoms, a hydroxyalkyl containing from 2 to 5 carbon atoms, a hydroxyalkyloxyalkyl containing from 4 to 10 carbon atoms, a hydroxyalkylpoly(oxyalkyl) containing 2 to 5 carbon atoms in each alkyl moiety and from 2 to 5 oxyalkyl units, aralkyl containing 7 to 8 carbon atoms or aryl containing 6 to 7 carbon atoms;
• R represents an alkylene group containing from 1 to 8 carbon atoms
• each R7 represents hydrogen; and said oil contains from 0.1 to 5 percent weight of said compound.
• a lubricating oil composition comprising:
• Steps (1) and (2) are conducted at a temperature of from 0 C. to 50 C.
• said dihaloalkane is a dichloroalkane containing from 2 to 8 carbon atoms and said oil contains from 0.1 to 5 percent of said fourth reaction product.

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• 1971
  • 1971-11-15 US US00199034A patent/US3778370A/en not_active Expired - Lifetime
• 1972
  • 1972-10-24 DE DE2252076A patent/DE2252076A1/de not_active Ceased
  • 1972-11-07 GB GB5137372A patent/GB1367012A/en not_active Expired
  • 1972-11-08 FR FR7239561A patent/FR2165867B1/fr not_active Expired
  • 1972-11-13 IT IT31588/72A patent/IT970442B/it active
  • 1972-11-14 JP JP11355572A patent/JPS5347123B2/ja not_active Expired

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