Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
  • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
• • 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
  • 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
• • 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
  • 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
  • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
• • 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/06—Perfluorinated compounds
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/08—Halogenated waxes
• • 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
  • 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
• • 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
  • 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
  • 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
  • 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
• • 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
  • 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

• the present invention melatesto improvements in sulfurized additives for lubricating, compositions, to a method otpreparingsuch additives and to compositions containing them.
• the invention relates -to' additive compo sitionsprepared by treating monocyclic terpenio hydrocarbons and related materials 'liavinga' s-i-milar-unsaturated Snon-ammatic ringstructure, to incorporate sulfur, phosphorus and; chlorine-"or other halogen therein; thereby convert such 10 compositions intdextremepressure agents or oxidation or corrosion inhibitors for'lubricating oils and g ieafifist As is well known in theart, ordinary hydrocarbon oils, e.
• lubricatingoils' derivedfirom pe troleum are good lubricants iorfimanypurposesi but are deficient in strength 0f'lub1i'cating"fi m' when subjectedatoahighunit pressures.v
• the same iss-tr-uexof .the synthetic oils, .i: e, estersgoihihasio:
• gears are subject tosliding contact as well as, -or as" distinguished trom, true-rolling contact,--and; hen'ce, they are particularly sub-- Jectttosevere and intolerable wearunless pro-- tected by an adequate-lubricant.
• ne e dis-r ov rt tha e r lat v l mexn ns a nd ieh1y -.erre tiv -,e reme pre sur dit ve ay: en n ed it-fir tttea nae mo qc i te r e e. h a l m n na pe ten t rDi Qlinamma terpinene, and the like, with a sulfur chloridend t en w th i whose.. s u su fide o nc rpoat all 1 h e r ell elit lfu c l rin and phase.
• an -inex-- pensive lubricating oil additive is prepared pref erably by first partially reacting the monocyolic' In general, these.
• terpene diolefin
• sulfur chloride is preferably added in such quantities and reacted under such conditions that approximately one of the double bonds of the terpene, on the average, is saturated thereby.
• the phosphorus sulfide is then introduced and it reacts largely with the second double bond giving a single compound containing all three of the elements, phosphorus, sulfur and chlorine.
• the quantity of phosphorus sulfide used is considerably less than that required to saturate the second double bond of all the terpene molecules. Apparently, some polymerization takes place. In general, only a small amount of phosphorus sulfide is used where the product is intended as an extreme pressure additive. Larger proportions may be used where the product is to be used in very small quantities as an oxidation or corrosion inhibitor.
• Example I 797 g. (475 c. c.) of sulfur monochloride was added to 1 liter (841 g.) of special commercial dipentene (from Hercules Powder Co.).
• This special dipentene had the following composition: 6% a-pinene, 7% a-terpineol, 10% para cymene. 31% dipentene, 39% terpinolene, 132.4(8) para menthadiene, 2% residue.
• the para cymene appears to be the only non-reactive component. Therefore, only about 90% of the special dipentene takes partin the reaction.
• the sulfur monochloride was introduced into the terpene at a rate of 15-20 0. e. per minute at 75-100 C. with constant stirring. After all the S2012 was added, the product was heated at 75-100 C. for to 1 hour.
• the SzClz-treated "dipentene (mixture) gave an analysis of 17.4% chlorine and 23.7% sulfur.
• 150 g. of the S2Cl2-treated dipentene was diluted with 150 g. of a naphthenic lube distillate of grade SAE 30. g. of P483 was added and heated with stirring for one hour at '125-150 C. HCl was liberated. After one hour of heating, there were added 25 g. Lorol B alcohol, which is a well known commercial mixture of C10 to C18 primary alcoholsypredominantly about C12, prepared from coconut oil, and heating was continued for minutes more. The product was blown with nitrogen gas and filtered through a commercial filter aid known as Hyfio. The final product contained 3.74% chlorine 13.65% sulfur 1.68% phosphorus The following blend of the above product was made:
• the product had the following analysis:
• Timken'machine test Pass 33 lbs.
• SAE machine test Pass 280 lbs.
• Copper strip test Pass case of the dichloride S012, the mol ratio of SCI:
• the reaction temperature when employing S2Cl2 can be between 60 and 125 C., preferably from 75 to 100 C.
• the dichloride When the dichloride is employed, it should be added at a lower temperature, such as 30 to 60 C. to avoid a violent reaction, and thereafter the reaction can be completed at a higher temperature such as 75 to 100 or 125 C.
• the addition reaction is substantially complete in from to 1 /2 or 2 hours.
• the phosphorus sulfide is then added, preferably in an amount which will give a product containing from about 0.04 to about 4.0 weight per cent of phosphorus on the 100% undiluted basis.
• This range corresponds to reacting from about 0.000875 to about 0.0875 mols P483 (containing 0.0035 to 0.35 atoms of phosphorus) per mol of S2Cl2-treated terpene.
• the reaction is conducted at a temperature of 100 to 175 C., preferably from 125 to C., until the reaction is substantially completed, requiring a time of from about A; to 2 hours.
• the molar proportions of phosphorus sulfide will runbetween about 0.001 and 0.1.
• the finished lubricant preferably contains '2 quantity of a conventional chlorinated hydro-N long chain aliphatic structure;Thehalogenated hydrocarbon is, combined with a smaller quantity of thedipentene orother treated terpene.
• a preferred composition range is from aboutv 80- 95%. of the, oil or other lubricant, 4 to 15% ofthemalogenated hydrocarbon; and 1 to of the: treated 'jterpene.
• the preferred proportions are about 90% of;the:lubricant, preferably mineral lubricating oil, with about 7.5% of the halogenated hydrocarbon and about 2.5% of the treated terpene.
• auxiliary additive such as the chlorinated hydrocarbon referred to above.
• the terpene treated first with a sulfur chloride and subsequently with a phosphorus sulfide is quite adequate by itself.
• the single additive preferably comprises from 2 to 20% of the weight of the total composition. More specifically, proportions of about 5 to 12% will ordinarily be used.
• the present invention comprehends both the treated dipentene as a new product per se together with process for its treatment, and also the lubricating composition containing the treated dipentene or other terpene as an additive.
• the additive itself may be used in straight mineral oils or in blends with synthetic oils and also in lubricating greases and lubricating compositions of widely varying consistencies.
• An extreme pressure additive composition for lubricants consisting essentially of the reaction product or about 1 molar proportion of a monocyclic terpene with about 1 to 2 molar proportions of a sulfur chloride, the quantity of said sulfur chloride being substantially sufficient to saturate one double bond in said terpene, said reaction product being further reacted with about 0.001 to 0.1 molar proportion of phosphorus sulfide at a temperature of 100 to 175 C.
• composition according to claim 1 wherein the sulfur chloride is S2012.
• a lubricating composition consisting essentially of 80 to 95% by weight of mineral base lubricating oil, 1 to 5% of the reaction product of one molar proportion of a monocyclic terpene treated first with about 1 to 2 molar proportions of a sulfur chloride and reacted thereafter with about 0.001 to about 0.1 molar proportions of a phosphorus sulfide at a temperature of 100 to 175 C., and 4 to 15% of a halogenated long chain aliphatic. hydrocarbon; said sulfur chloride being. effective to. substantially 's'aturate an average/of about. one: double bond per terpene molecule'. and said phosphorussulfide being effective:
• a lubricating composition consisting essentially of about by weight of mineral base lubricating oil, 7.5% of chlorinated wax, and 2.5% of a reaction product of a monocyclic terpene, treated first with about 1 to 2 mols per mol of said terpene of a sulfur chloride and treated thereafter with about 0.001 to 0.1 mols of a phosphorus sulfide at a temperature of to 175 C.
• composition according to claim 1 wherein the terpene is dipentene.
• composition according to claim 4 wherein the terpene is dipentene.
• composition according to claim 7 wherein the terpene is dipentene.
• a method of preparing an extreme pressure additive for lubricants and the like which consists in first reacting 1 molar proportion of a monocyclic terpene with about 1 to 2 molar proportions of sulfur chloride at a temperature between about 60 and C., the quantity of sulfur chloride being approximately that required to saturate one double bond of the terpene, and thereafter reacting the treated dipentene with about 0.001-to about 0.1 molar proportions of phosphorus sulfide at a temperature between about 125 and C. for a period of A to 2 hours to partially saturate a second double bond of said terpene.
• a method of preparing a sulfur and phosphorus-containing organic compound which comprises treating a non-aromatic mono-cyclic terpenic C10 material having a six-membered unsaturated ring with approximately one to two molar equivalents of a sulfur chloride at a temperature of 60 to 125 C. for about to 2 hours, and subsequently treating the sulfur chloridetreated product with about 0.001 to 0.1 molar proportions of phosphorus sulfide at a temperature of 100 to C. for about to 2 hours.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Biochemistry (AREA)
• General Health & Medical Sciences (AREA)
• Molecular Biology (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Lubricants (AREA)

Priority Applications (4)

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Citations (4)

• 0
  • NL NL76406D patent/NL76406C/xx active
• 1949
  • 1949-08-19 US US111343A patent/US2613183A/en not_active Expired - Lifetime
• 1950
  • 1950-05-31 GB GB13602/50A patent/GB686074A/en not_active Expired
  • 1950-06-13 FR FR1020115D patent/FR1020115A/fr not_active Expired

Patent Citations (4)

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