US2631130A - Mineral oil additive - Google Patents

Mineral oil additive Download PDF

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Publication number
US2631130A
US2631130A US124256A US12425649A US2631130A US 2631130 A US2631130 A US 2631130A US 124256 A US124256 A US 124256A US 12425649 A US12425649 A US 12425649A US 2631130 A US2631130 A US 2631130A
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Prior art keywords
oil
phosphorus
sulfur
product
gms
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US124256A
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Inventor
Jeffrey H Bartlett
Jr Thomas Cross
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Standard Oil Development Co
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Standard Oil Development Co
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Priority to NL75561D priority Critical patent/NL75561C/xx
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Priority to US124256A priority patent/US2631130A/en
Priority to GB19545/50A priority patent/GB687512A/en
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    • 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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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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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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/20—Natural rubber; Natural resins
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/02—Hydroxy compounds
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    • C10M2207/027—Neutral 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
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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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
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/40—Fatty vegetable or animal oils
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    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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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
    • C10M2209/082—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 monocarboxylic
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10—Amides of carbonic or haloformic acids
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
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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
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
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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
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
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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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    • 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
    • C10M2223/045—Metal containing thio derivatives
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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Definitions

  • oils but are also useful, when added to lubricants, for the purpose of protecting exposed metallic surfaces of such engines against rusting when the same are e air.
  • the additives are alsoq-usefuh generally -as anti-o idants.-; in
  • the alcohols which maybe employed in the formation of the new additives may be defined in their broadest scope by the formula containing 1 to 3 -carbon atoms,;-B,' is am ethyl or e yl ro p .-.a d m an n are mb one or more of the of'the formula r f! Ilia ()o11'-o 1ori in'whi'ch R1 'and'Rz each represent hydrogen .or a methyl'group, at least one being'hydroge'n, and
  • venient to prepare "iconvenientl y prepared by reacting the phos-. phorusand sulfur reaction product with metallic radicals are alike or in which they are different, 7
  • esters in which at least one of the esterifying; acid radicals contains a double bond.
  • suitable acids include laurl'c, myrist'ic. palmitic, stearic, arachidic, behenic, oleic; eruci liholeic,
  • undecylenic and homologous acids also naturally occurrin fatty acids and mixtures of fatty acids.
  • esters derived from the alcohols and: acids described above are reacted with. acombination It is preferable toemploy a sulfide. of phosphorus, such as PzSz; PiS's, P iSa; or P101, or mixtures thereof; but mixtures of elemental sulfur and elemental phosphorus may likewise be employed, in: which case it is preferable toemploy powdered sulfur and white phosphorus; Likewise, a mixture of one or more sulfides of phosphorus and elemental sulfur and/or elemental phosphorusmay be employed.
  • the amounts of sulfur and phosphorus which are advantageously employed depend upon the number of doublebonds present the ester indouble-bondedhydrocarbon groups, and it is preferred, to react from :1 to 1 atom of phosphorusand 0.1 to 3 atoms of sulfur for each such double-bond on the ester molecule. In general, the higher proportions of phosphorus and sulfur or sulfide of phosphorus may be employed when the ester molecule contains saturated oil-solubilizing hydrocarbon groups. In general, the tempearture at which the reaction blithea sulfide of phosphorus or mixture of sulfur and?
  • phosphorus with the ester is carried out is; mm 200 to 500 FL, and the time required ts-substantially complete the reaction is generaliy'from 1' to hours.
  • a solvent for the ester in which case the solvent should be relatively inert to phosphorus and sulfur.
  • solvents include, for example, benzene, o-dichlorbenzene, mineral oils; and the like.
  • reaction products preas: described may be employed as such or in the: form of their metal salts.
  • the metals employed arepreferably group II metals and the calcium. salts: are: particularly desirable and com
  • Such metal salts may be oxides or hydroxides.
  • Such metallic compounds may be added to the reaction mixture in which 4 the phosphorus and. sulfur reaction products are formed, and the mixture heated to a temperature of the range of 50-400 F.
  • the additives of the present invention are preferably added to mineral oils in proportions ranging from 0.01% to the proportion being preferably about 1.0 to 5.0% when employed as corrosion inhibitors and detergents in mineral lubricating oils.
  • the proportions giving the best results will vary somewhat according to the nature. of the additive-and the: specific quality characteristics of the oil to be improved by the use of the additive.
  • Example 2 product had a neutralization number of 29.07.
  • Ch 200 gms. (0.1 7 mol) of the aboveester was placed in a small 3-necked flask equipped with a sane. Nitrogen was bubbled in 1dw1y"aha the contents heated to 248 F.. after which 186 gms. (0.084 mol) of P285 was added over a period of 1 hour. The temperature was then raised to 302 F. and held at. this point for 3 hours. A filter-- aid was added and the product filtered hot.
  • Example 3 (a) 2225 gms. (7.88 mols) of oleic acid wa placed in a -liter 3-necked flask and heated to 302 F. while bubbling nitrogen through the mixture. '23:; gms. (1.75 mols) of pentaerythritol was then added over a period of minutes, after which the temperature was raised gradually over a period of 1 hour to a temperature of 446 F. and
  • Example 4 A 2-liter 3-necked flask equipped as in Example 3(b) was charged with 200 gms. (0.168 mol) pentaerythritol tetraoleate (prepared as describedin Example 3(a) and 344 gms. of solvent extracted Swiss-316.
  • pentaerythritol tetraoleate prepared as describedin Example 3(a) and 344 gms. of solvent extracted
  • Example 6 h (a) 229 gms. (0.9'mol) dipentaerythritol, 1654 gms. (5.9 mols) oleic acid, 10 cc. xylene, and 1 gm. calcium hydroxide were charged into a 3-liter 3-necked flask equipped with stirrer, water trap,
  • Example 7 Dipentaerythritol hexaoleate (prepared as described in Example 6 (0)) was reacted with sulfur and P285 in the proportions of 3 mols of sulfur and 0.75 mol of P285 for each mol of the ester, the conditions of the preparations being the same as in Example 4, in which 200 gms. dipentaerythritol hexaoleate, 342 gms. of oil solvent, 10.3 gms. sulfur, and 17.9 gms. P2S5 were used. The product contained about 40% active ingredient.
  • Example 8 100 gms. (0x18411101) 'ofpentaerythritol tetrav linoleate (a commercial product) ,-9.4 gms.- 0.042
  • Example 9 gms. (0.073 mol) of the tetraoleate of pentaerythritol hydroxy ethyl ether (commercial product), 8.1 gms. (0.037 mol) of Pass, and 162 gms. of the solvent employed in Example 3(b) were reacted under the conditions of Example 3(b), the product containing about 40% active ingredient.
  • Example 11 The calcium salt of the product of Example 3 "(-b')- was prepared in the manner described in Example 10, using 200 g ms. of: the. reactionprod- I *uctand gm's. of calcium hydroxide.
  • Example 12 The calcium salt. of. the product of Example 4 was preparedinthe manner described in Example.
  • Example 15 The calcium saltof the product of Example 7 was similarly prepared.
  • Example 17.-Carbon black dispersion test In this test which is used to measure' the'dispersive power of the lubricating oils, 500 cc; of 2.21%? blend of theactive ingredient in a-solvent extracted Mid-Continent paraflinic oil of 52 seconds viscosity (Saybolt) at 210 F. is agitatedwith 6 by Weight of carbon black and. allowed tosettle for 24 hours at 200 F. Foncomparison a similar amount of unblended base-0111's simi- To thiswas: added ucts of- Example- 1;( b) and. Example 16- Since these products-are 40% oil concentrates,.2.5'% by weight ot each was. employed in preparing the blendsfor the test.. The results are shown in Table I,
  • Exampleir-Labomtory bearing corrosion test Blends were made of the products (40% concentrates in oil). of' Examples 1 to 15, inclusive, in a. lubricating oil base consisting of a, well refined; solvent extracted paraffinic mineral lubricating oil of S. A. E.-20 viscosity grade in such proportions that in. each. case a blend was prepared containing 0.25% of the active ingredient; These blends and a sample of the unblended base oil were submitted to a corrosion testdesigned to test the. eiiectiveness of. the additive in inhibiting, corrosion of a typical copperlead bearing.
  • Example 20 -Copper strip test
  • a lubricating oil base consisting of a solvent extracted Mid-Continent neutral distillate of 44.1 seconds viscosity (Saybolt) at 210 F., in an amount suificient to form a blend containing 0.75% of active ingredient.
  • These blends and a sample of the unblended base oil were submitted to a copper strip corrosion test which 10 cracking coil tar fractions and coal tar or shale oil distillates may also be used.
  • animal, vegetable or fish oils or their hydrogenated or voltolized products may be employed in admixtures with mineral oils.
  • base stock chosen should normally be an oil which with the new additive present gives the optimum performance in the service contemplated.
  • one advantage of the additives is that their use also makes feasible the employment of less satisfactory mineral oils, no strict rule can be laid down for the choice of the base stock.
  • the additives are normally sufficiently soluble in the base stock, but
  • auxiliary solvent agents may be This method comprises immersing a polished used.
  • the lubricating oils will usually range metallic copper strip in the oil blend to be tested from about 40 to 150 seconds (Saybolt) viscosity for periods of and 3 hours at 212 F. and notat 210 F.
  • the viscosity index may range from ing the extent of staining. Numerical ratings to 100 or even higher. from 1 to 10 denote discoloration ranging from 20 Other agents than those which have been no staining to a black surface film, respectively.
  • Example 10 Pentaerythritol Oleate-Stearate. l: .5 22
  • Example 11 Pentaerythritolletraoleate 1: .5 17 3 3
  • Example 12 i0 l: .5 1:2 14 2 2
  • Example 13 0 l: .75 32 3 4
  • Example 14 Dipentaerythritol Hexaoleate 1: .75 13 4 7
  • Example 16 Pentaerythritol O1eate-Stearate.-.. 1: .5 34
  • the products of the present invention may be dispersers, anti-oxidants, thickeners, viscosity inemployed not only in ordinary hydrocarbon lubricating oils but also in the heavy duty type of lubricating oils which have been compounded with such detergent type additives as metal soaps, metal petroleum sulfonates, metal phenates, metal alcoholates, metal alkyl phenol sulfides, metal organo phosphates, phosphites, thiophosphates and thiophosphites, guanidine salts, metal xanthates and thioxanthates, metal thiocarbamates, and the like.
  • Other types of additives, such as phenols and phenol sulfides, may also be present.
  • the lubricating oil base stocks used in the compositions of this invention may be straight mineral lubricating oils or distillates derived from parafiinic, naphthenic, asphaltic or mixed base crudes, or, if desired, various blended oils may be employed as well as residuals, particularly those from which asphaltic constituents have been carefully removed.
  • the oils may be refined by conventional methods using acid, alkali and/or clay or other agents such as aluminum chloride, or they may be extracted oils produced by. solvent extraction with solvents such as phenol, sulfur dioxide, etc.
  • Hydrogenated oils or white oils may be employed as well as synthetic oils prepared, for example, by the polymerization of olefins or by the reaction of oxides of carbon with hydrogen or by the hydrogenation of coal or its products.
  • R is a member of the group consisting of methylol radicals and alkyl radicals containing 1 to 3 carbon atoms
  • R. is a member of the group consisting of methyl and methylol radicals
  • m and n are numbers from 0 to 2
  • said ester being derived from said alcohol by substituting all of the free hydroxyl groups thereof with radicals of monobasic carboxylic acids containin 8 to 30 carbon atoms per molecule
  • B salts of said products and a metal selected from groups I and II of the periodic table; the re-.
  • actants beingemployed in such proportions that from 0.2 to 0.4 atom of phosphorus and 0.5 to 1 atom of sulfur are present for each acid radical present in the ester, and the reaction being conducted at a temperature in the range of about 200 to about 300 F.
  • composition according to claim 1 in which the. mineral oil is a lubricating oil fraction.
  • composition according to claim 3 in which the mineral oil is a lubricating oil fraction.
  • composition according to claim 3 in which the alcohol from which the ester is derived is pentaerythritol.
  • composition according to claim 5 in which the ester is pentaerythritol tetraoleate.
  • composition according to claim 11 in which the metal is calcium.
  • a mineral lubricating oil containing dissolved therein 0.01 to 15% of the. calcium salt of the product obtained by reacting one molecular proportion of pentaerythritol tetraoleate with 0.75 molecular proportion of phosphorus pentasulfide at a temperature of about 250 to 300 F.
  • a composition consisting essentially of a mineral lubricating oil and an additiveas defined.
  • the amount of said additive in the. composition being 25 to 50 by weight.
  • composition consisting essentially of a mineral lubricating oil and an additive as defined in claim 14, the amount of said additive in the: composition being 25 to 50 by Weight.
  • composition of matter a. member of the class consisting of: (A) the products obtained by reacting a combination of the elements sulfur and phosphorus with an ester of an alcohol selected from the group consisting of alcoholsof the formula in which R is a member of the group consisting of methylol radicals and alkyl radicals containing 1 to 3 carbon atoms, R is a member of the group consisting of.
  • ester being; derived from said alcohol by substituting all ofthe free hydroxyl groups thereof with radicals of: monobasic carboxylic acids containing 8 to 30 carbon atoms per molecule; and (B) salts of said" products and a metal selected from groups I and II of the periodic table; the reactants being employed in such proportions that from 0.2 to 0.4 atom of phosphorus and from 0.5 to 1 atom of sulfur are present for each acid radical in the ester molecule, and the reaction being conducted at a temperature in the range of about 200 to about 300 F.

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  • General Chemical & Material Sciences (AREA)
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  • Organic Chemistry (AREA)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2830023A (en) * 1952-09-03 1958-04-08 Exxon Research Engineering Co Complex ester-phosphorus sulfide reaction products and lubricants containing them
US3214423A (en) * 1961-04-21 1965-10-26 Atlas Chem Ind Thiophosphates of polyoxyethylene compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2441587A (en) * 1944-07-25 1948-05-18 Standard Oil Co Method of preparing composition of matter suitable for use as a lubricant and as an addition agent to lubricants
US2483600A (en) * 1946-05-16 1949-10-04 Pure Oil Co Preparation of high-viscosity extreme pressure base by airblowing
US2542161A (en) * 1946-03-09 1951-02-20 Pure Oil Co Mineral oil lubricant containing phosphorized and sulfurized glyceryl trioleate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2441587A (en) * 1944-07-25 1948-05-18 Standard Oil Co Method of preparing composition of matter suitable for use as a lubricant and as an addition agent to lubricants
US2542161A (en) * 1946-03-09 1951-02-20 Pure Oil Co Mineral oil lubricant containing phosphorized and sulfurized glyceryl trioleate
US2483600A (en) * 1946-05-16 1949-10-04 Pure Oil Co Preparation of high-viscosity extreme pressure base by airblowing

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2830023A (en) * 1952-09-03 1958-04-08 Exxon Research Engineering Co Complex ester-phosphorus sulfide reaction products and lubricants containing them
US3214423A (en) * 1961-04-21 1965-10-26 Atlas Chem Ind Thiophosphates of polyoxyethylene compounds

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