US2654711A - Monocyclic terpene-sulfur-phosphorus sulfide reaction product and lubricating oil containing the same - Google Patents

Monocyclic terpene-sulfur-phosphorus sulfide reaction product and lubricating oil containing the same Download PDF

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Publication number
US2654711A
US2654711A US105066A US10506649A US2654711A US 2654711 A US2654711 A US 2654711A US 105066 A US105066 A US 105066A US 10506649 A US10506649 A US 10506649A US 2654711 A US2654711 A US 2654711A
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Prior art keywords
sulfur
phosphorus
oil
sulfide
lubricating oil
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US105066A
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Abraham D Kirshenbaum
Harry W Rudel
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Standard Oil Development Co
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Standard Oil Development Co
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Priority to NL78997D priority Critical patent/NL78997C/xx
Application filed by Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to US105066A priority patent/US2654711A/en
Priority to GB15305/50A priority patent/GB679296A/en
Priority to FR1021015D priority patent/FR1021015A/fr
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    • C10M159/12—Reaction products
    • C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic 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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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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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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    • 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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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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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
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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
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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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    • 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
    • C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
    • C—CHEMISTRY; METALLURGY
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    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
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    • C10N2010/04—Groups 2 or 12
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13
    • 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
    • C10N2040/02—Bearings
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    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • C—CHEMISTRY; METALLURGY
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • the present invention relates to a new composition of matter .which improves the properties of mineral oil lubricants when added thereto in small amounts.
  • the new additive of the present invention is a monocyclic terpene which has been modified by combining therewith both sulfur and phosphorus.
  • the product has the property of inhibiting oxidation in mineral oils and in imparting to such oils improved load bearing char acteristics.
  • terpenes by the process of sulfurization
  • a cutting oil composition comprising a mineral oil to which is added a sulfurized terpene such as sulfurized pine oil, turpentine, pinene, and the like.
  • a sulfurized terpene such as sulfurized pine oil, turpentine, pinene, and the like.
  • Terpinol which contains a hydroxyl group, is also mentioned.
  • the terpene is cooked with sulfur at rather high temperatures, e. g., about 200 to 210 C., for a period of half an hour or more.
  • the sulfur is rather loosely attached, at least in part, to other sulfur atoms which have been incorporated in the terpene molecule structure, so that it is over-active and hence corrosive to metals.
  • the sulfurized terpenes such as those described by Kobbe have been found to be strongly corrosive to metals, especially those containing copper.
  • the new composition may be added to mineral base lubricants to improve their load bearing properties.
  • mineral base lubricants is meant the usual crankcase oils, gear oils, greases, etc., which contain major proportions of mineral lubricating oil fractions as the basic lubricant.
  • one molecular proportion of the monocyclic terpene will absorb about two atomic proportions of elemental sulfur in this reaction, and this proportion of sulfur is accordingly a preferred maximum proportion to use in the reaction.
  • Somewhat lesser proportions of sulfur i. e., down to 1.5 atomic proportions to one molecular proportion of terpene, can be used in order to ensure more or less complete reaction of the sulfur, but the final product will contain less sulfur and be somewhat less potent. If greater proportions of sulfur are used, the
  • product may contain unreacted sulfur in solution which has the disadvantages that it is corrosive and tends to crystallize out of solution on standing.
  • the use of a small excess of sulfur will not be harmful, since a small amount of sulfur is lost in the form of hydrogen sulfide during the reaction.
  • the reaction is preferably conducted in the presence of a liquid medium, and since the additive is preferably to be employed in a mineral lubricating oil base, such an oil serves conveniently as the medium of the reaction.
  • the temperature at which the reaction is carried out should be at least about 120 C., the melting point of sulfur, and generally should be of the order of 140 to 200 C., more preferably from 150 to 170 C.
  • the reaction is continued at least until the tendency of the reaction mixture to stain copper, as measured by a modified C. R. C. copper strip test (see Example 3), has been substantially reduced. Normally, it is preferred to conduct the reaction to substantial completion which requires a period of one-half to 20 hours, depending on the temperature of thereaction and more usually for a period of 2 to hours. No catalyst is required.
  • a plasticizer for the reaction such as an aliphatic alcohol containing at least eight carbon atoms per molecule.
  • the amount of the sulfide of phosphorus is low, i. e., of the order of 0.02
  • the sulfur may be employed in the form of ordinary flowers of sulfur.
  • the phosphorus sulfide may be any phosphorus sulfide, phosphorus trisulfide (P483) being somewhat preferable because of its high phosphorus content. It is ordinarily convenient to mix the sulfur and sulfide of phosphorus and heat the same to the reaction temperature, after which the dipentene or other monocyclic terpene is gradually added, preferably in admixture with a diluent such as a lubricating oil fraction. Heating is then continued until the reaction is complete, and the product is then pref erably blown with nitrogen or other inert gas to remove any hydrogen sulfide present.
  • thiophosphoric acid prepared by reacting a sulfide of phosphorus with an alcohol or phenol.
  • Typical of such compounds are di-n-butyl dithiophosphoric acid, di-(ethylhexyl) dithiophosphoric acid, di-
  • the essence of the present invention is the production and use of terpene derivatives made by reacting a monocyclic terpene simultaneously with sulfur and a phosphorus sulfide, such derivatives being useful either alone or in combination with other additives as addition agents for mineral lubricating oils and greases.
  • the invention is preferably and specifically applicable to dipentene and its isomers, e. g., terpinolene, but it also has application to the substituted terpenes, such as terpineol, diterpinyl ethylene ether, and similar compounds.
  • the alcohol and aldehyde derivatives of dipentene and terpinolene are useful for some purposes, but their resistance to oxidation and their tendency to inhibit corrosion are not as satisfactory as the products derived from the hydrocarbons.
  • the sulfurized and phosphorus sulfide treated terpenes may also be used as extreme pressure additives.
  • they may be used alone or they may be used in combination with other extreme pressure additives, especially in combination with the sulfurized and/or chlorinated long chain hydrocarbons, fatty materials, and aliphatic esters such as chlorinated wax, sulfurized and phosphorus sulfide treated fatty acids and fatty oils of 12 to 22 carbon atoms, sulfurized and/or phosphorus sulfide treated abietic acid and its lower alkyl esters, and the like.
  • the latter materials are well known extreme pressure additives of the prior art.
  • the proportions of the additives of the present invention which are useful for preventing oxidation and corrosion are of the order of about 0.05 to 2.0%, proportions of 0.1 to 0.4% being especially preferred.
  • proportions of the order of 1% to 15% When the treated terpenes are used alone. They may be used in smaller proportions for this purpose when combined with other conventional extreme pressure additives such as those previously mentioned.
  • These concentrated solutions may be produced by using a lubricating oil as the diluent in the process of preparation of the additives, in an amount suflicient to produce these concentrations. It is only necessary to dilute these concentrated solutions with a base oil to produce a lubricant containing the desired amount of additive. Hence, the proportions used in the mineral base lubricant may vary from as little as 0.05% to as much as 50% of the weight of the total composition, depending upon the purpose.
  • the product was then blown with nitrogen gas for 1 to 1 hours at 120 to 140 C. to remove the unreacted hydrocarbon and dissolved Has.
  • the final product which was an oil concentrate containing about 50% active ingredient, gave the following analysis: sulfur 12.72%, phosphorus 2.54%.
  • EXAMPLE 2 A mixture of 96 grams (3 mols) of sulfur and 6.95 grams (0.032 mol) of P483 was heated to about 150 C., after which a mixture of 252 grams (1.85 mols) of Special Dipentene and 300 grams of the lubricating oil diluent employed in Example 1 was slowly added. The mixture was then heated for 3 hours at 150-170 C. and the product blown at room temperature (25 C.) with nitrogen gas for hour. The product, which was an oil concentrate containing about 50% active ingredient, gave the following analysis: sulfur 12.71%, phosphorus 0.56%.
  • EXAMPLE 3 Each of the products of Examples 1 and 2 (each containing about 50% of active ingredient) was blended in 1% (by weight) concentration in a lubricating oil base consisting of a well refined, solvent extracted paraflinic type mineral lubricating oil of SAE 20 viscosity grade and the solutions thus formed were submitted to a copper strip corrosive test which was a modification of OR.
  • C. method LAG-445 This method comprises essentially immersing a polished metallic copper strip in the oil blend to be tested for 3 hours a 212 F. and noting the extent of staining. Numerical ratings from 1 to 10 denote discolorations from no staining to a black surface film, respectively.
  • the products of the present invention may be employed 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, thiophosphates, phosphites and thiophosphites, metal salicylates, metal xanthates and thioxanthates, metal thiocarbamates, amines and amine derivatives, reaction products of metal phenates and sulfur, reaction products of metal phenates and phosphorus sulfides, metal phenol sulfonates, and the like.
  • detergent type additives as metal soaps, metal petroleum sulfonates, metal phenates, metal alcoholates, metal alkyl phenol sulfides, metal organo phosphates, thiophosphates, phosphites and thi
  • additives of the present invention may be used in lubricating oils containing such other addition agents as barium tert. octylphenol sulfide, calcium tert.-amylphenol sulfide, cadmium oleate, nickel oleate, barium octadeoylate, calcium phenyl stearate, zinc diisopropyl salicylate, aluminum naphthenate, calcium cetyl phosphate, barium di-tert.-amylphenol sulfide, calcium petroleum sulfonate, zinc methylcyclohexyl thiophosphate, calcium dichlorostearate, etc.
  • Other types of additives, such as phenols and phenol sulfides, may be employed.
  • the lubricating oil base stocks used in the compositions of this invention may be straight mineral lubricating oils or distillates derived from paraiiinic, naphthenic, asphaltic, or mixed base crude, 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, for example, by solvent extraction with solvents such as phenol, sulfur dioxide, furfural, dichlorodiethyl ether, nitrobenzene, crotonaldehyde, 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.
  • 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 admixture with mineral oils.
  • the base stock chosen should normally be an oil which without the new additive present gives the optimum performance in the service contemplated. However, since one.
  • the oil must possess the viscosity and volatility characteristics known to be required for the service contemplated.
  • the oil must be a satisfactory solvent for the additive, although in some cases auxiliary solvent agents may be used.
  • the lubricating oils may have been produced, may vary considerably in viscosity and other properties depending upon the particular use for which they are desired, but they usually range from about 40 to 150 seconds (Saybolt) viscosity at 210 F.
  • oils of higher viscosity index are often preferred, for example, up to '75 to 100, or even higher, viscosity index.
  • agents may also be used such as dyes, pour point depressants, heat thickened fatty oils, sulfurized fatty oils, organo-metallic compounds, metallic or other soaps, sludge dispersers, antioxidants, thickeners, viscosity index improvers, oiliness ogents, resins, rubber, olefin polymers, voltolized fats, voltolized mineral oils, and/or voltolized waxes and colloidal solids such as graphite or zinc oxide, etc.
  • Solvents and assisting agents such as esters, ketones, alcohols, aldehydes, halogenated or nitrated compounds, and the like may also be employed.
  • Assisting agents which are particularly desirable as plasticizers and defoamers are the higher alcohols having preferably 8 to 20 carbon atoms, e. g., octyl alcohol, lauryl alcohol, stearyl alcohol, and the like.
  • a mineral lubricating oil composition containing 0.05 to 50% by weight of a product obtained by simultaneously reacting one molecular proportion of a monocyclic terpene with about 1.5 to about 2 atomic proportions of sulfur and with about 0.01 to about 0.25 molecular proportions of a sulfide of phosphorus at a temperature of at least C. and up to a temperature of about 200 C.
  • composition according to claim 1 in which the sulfide of phosphorus is P483.
  • a mineral lubricating oil composition co taining about 40% to about 50% by weight of a product obtained by simultaneously reacting one molecular proportion of a monocyclic terpene with about 2 atomic proportions of sulfur and With about 0.01 to 0.25 molecular proportions of a sulfide of phosphorus at a temperature of at least 120 C. and up to a temperature of about 200 C.
  • a mineral lubricating oil composition containing about 40% to about 50% by weight of a product obtained by simultaneously reacting one molecular proportion of a monocyclic terpene with about 2 atomic proportions of sulfur and about 0.01 to about 0.25 molecular proportions of P433 at a temperature of 1&0" to 200 C.
  • a process which comprises heating a mixture of about one molecular proportion of a monocyclic terpene consisting essentially of a mixture of dipentene and terpinolene, about 2 atomic proportions of sulfur and about 0.02 molecular proportions of P483 in the presence of a mineral lubricating oil diluent at a temperature of about 150170 C. for a period of about 3 hours.

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  • Organic Chemistry (AREA)
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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
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  • Lubricants (AREA)
US105066A 1949-07-15 1949-07-15 Monocyclic terpene-sulfur-phosphorus sulfide reaction product and lubricating oil containing the same Expired - Lifetime US2654711A (en)

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NL78997D NL78997C (fr) 1949-07-15
US105066A US2654711A (en) 1949-07-15 1949-07-15 Monocyclic terpene-sulfur-phosphorus sulfide reaction product and lubricating oil containing the same
GB15305/50A GB679296A (en) 1949-07-15 1950-06-19 Improvements in or relating to compounds for use as additives to lubricants and lubricants containing such additives
FR1021015D FR1021015A (fr) 1949-07-15 1950-06-27 Compositions d'addition aux lubrifiants et nouveaux lubrifiants contenant ces compositions

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2721862A (en) * 1949-12-30 1955-10-25 Pure Oil Co Sulfurized terpenes and three step process for making same utilizing sulfurization promoters
US2738340A (en) * 1952-05-20 1956-03-13 Sinclair Refining Co Urea-pinene-sulfide reaction product
US2993856A (en) * 1957-11-18 1961-07-25 Texaco Inc Lubricant containing a sulfurized terpene and sulfurized sperm oil
US3455844A (en) * 1963-08-08 1969-07-15 Sinclair Research Inc Sulphurized and phosphorized extreme pressure agents
US20120108675A1 (en) * 2009-07-07 2012-05-03 Upm-Kymmene Corporation Process and apparatus for producing hydrocarbons by hydrogenating a terpene feed

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2413648A (en) * 1945-06-28 1946-12-31 Hercules Powder Co Ltd Terpene reaction product and method of producing
US2422585A (en) * 1944-05-08 1947-06-17 Standard Oil Co Lubricant
US2515222A (en) * 1947-07-18 1950-07-18 Sinclair Refining Co Sulfurized condensate of alphapinene and phosphorus pentasulfide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2422585A (en) * 1944-05-08 1947-06-17 Standard Oil Co Lubricant
US2413648A (en) * 1945-06-28 1946-12-31 Hercules Powder Co Ltd Terpene reaction product and method of producing
US2515222A (en) * 1947-07-18 1950-07-18 Sinclair Refining Co Sulfurized condensate of alphapinene and phosphorus pentasulfide

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2721862A (en) * 1949-12-30 1955-10-25 Pure Oil Co Sulfurized terpenes and three step process for making same utilizing sulfurization promoters
US2738340A (en) * 1952-05-20 1956-03-13 Sinclair Refining Co Urea-pinene-sulfide reaction product
US2993856A (en) * 1957-11-18 1961-07-25 Texaco Inc Lubricant containing a sulfurized terpene and sulfurized sperm oil
US3455844A (en) * 1963-08-08 1969-07-15 Sinclair Research Inc Sulphurized and phosphorized extreme pressure agents
US20120108675A1 (en) * 2009-07-07 2012-05-03 Upm-Kymmene Corporation Process and apparatus for producing hydrocarbons by hydrogenating a terpene feed
US9677011B2 (en) * 2009-07-07 2017-06-13 Upm-Kymmene Corporation Process and apparatus for producing hydrocarbons by hydrogenating a terpene feed

Also Published As

Publication number Publication date
NL78997C (fr)
GB679296A (en) 1952-09-17
FR1021015A (fr) 1953-02-13

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