US3192164A - Silicon-containing lubricant additives - Google Patents
Silicon-containing lubricant additives Download PDFInfo
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- US3192164A US3192164A US167220A US16722062A US3192164A US 3192164 A US3192164 A US 3192164A US 167220 A US167220 A US 167220A US 16722062 A US16722062 A US 16722062A US 3192164 A US3192164 A US 3192164A
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- Prior art keywords
- wear
- silver
- ketone
- silicon
- ketones
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003879 lubricant additive Substances 0.000 title description 2
- 229910052710 silicon Inorganic materials 0.000 title description 2
- 239000010703 silicon Substances 0.000 title description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title 1
- 229910052709 silver Inorganic materials 0.000 claims description 21
- 239000004332 silver Substances 0.000 claims description 21
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 20
- 150000002576 ketones Chemical class 0.000 claims description 16
- 239000000314 lubricant Substances 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- KHDSWONFYIAAPE-UHFFFAOYSA-N silicon sulfide Chemical compound S=[Si]=S KHDSWONFYIAAPE-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 19
- 239000000654 additive Substances 0.000 description 16
- 239000003921 oil Substances 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 229910000464 lead oxide Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- -1 methyl isopropylene ketone Chemical class 0.000 description 3
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 3
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 2
- 238000006388 chemical passivation reaction Methods 0.000 description 2
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- GARHHHWGJIXLDK-UHFFFAOYSA-N icosan-2-one Chemical compound CCCCCCCCCCCCCCCCCCC(C)=O GARHHHWGJIXLDK-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- POQLVOYRGNFGRM-UHFFFAOYSA-N 2-Tetradecanone Chemical compound CCCCCCCCCCCCC(C)=O POQLVOYRGNFGRM-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- ZMRQTIAUOLVKOX-UHFFFAOYSA-L calcium;diphenoxide Chemical compound [Ca+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZMRQTIAUOLVKOX-UHFFFAOYSA-L 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
- 229930193351 phorone Natural products 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
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- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/025—Silicon compounds without C-silicon linkages
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/024—Propene
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- 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
- 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
- C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
-
- 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
- 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
-
- 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
- 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
-
- 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
- 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
-
- 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
- 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
- C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2223/02—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
-
- 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
- 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
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
Definitions
- This invention relates to certain ketones for inhibiting the tendency of hydrocarbon lubricant oils to cause excessive wear of silver and silver-containing bearings.
- hydrocarbon lubricant oils contain sulfur compounds as oxidation or corrosion inhibitors. These sulfur compounds however promote excessive wear in silver and silver-containing bearings and bushings.
- reaction product of a ketone with silicon disulfide is an outstanding anti-silver wear additive when incorporated into hydrocarbon oils tending to cause excessive wear.
- the present additives may be prepared simply by reacting the corresponding ketone, which is preferably a dialkyl ketone having from 1 to 20 carbon atoms in each alkyl group, with silicon disulfide under anhydrous conditions, and preferably at a temperature of about, say, 8-0-150 C., for sufficient time until hydrogen sulfide evolution ceases.
- the structural formula of the resultant product is not presently known, nor is it readily ascert'ainable. However, it has been definitely established that a reaction product having characteristics different from either reactant is obtained.
- the preparation of the herein-described additives follows the technique of Fremy, Ann. Chim. Phys. (3), 38, 314 (1852), notwithstanding the statement by Malatesta, Gazz. Chim. Ital., 78, 753-63 (1948); Chemical Abstracts, 43, 4630 (1949), to the effect that SiS (does not) react with esters or ketones contrary to Fremy.
- the present additives are outstanding with respect to imparting oxidation inhibition to lubricants containing them.
- the silver wear-inhibiting properties of the present additives to reduce the wear promotion of sulfur-containing oxidation inhibitors, but the amount of such oxidation inhibitors may likewise be reduced inasmuch as the present additives are themselves inhibitors against oxidation.
- dialkyl ketones in which each alkyl group has from 1 to '20 carbon atoms, offering advantages With respect to ease of preparation, solubility, and effectiveness in inhibiting silver wear and oxidation.
- suitable dialkyl ketones include acetone, methyl n-propyl ketone, methyl isopropylene ketone, diethyl ketone, hexanone-Z, hexanone-3, methyl n-octyl ketone, etc.
- -Polyketones including acetylacetone and acetonylacetone; unsaturated ketones such as mesityl oxide and phorone; halogenated ketones such as bromoacetone and chloroacetone; cyclic ketones such as diphenyl ketone and dinaphthyl ketones, may also be used, either alone or in admixture with each other.
- Lubricant compositions which advantageously may be incorporated with the present additive are the hydrocarbon oils of suitable viscosity range, and which may contain various additives for different purposes.
- the hydrocarbon base may be either a natural or synthetic (e.g., propylene or isobutylene polymer) oil, suitably having a viscosity from about 20 S.S.U. at 100 to about 3,000 S.S.U. at 210.
- Additives commonly employed include detergents such as the metal sulfonates or metal phenyl sulfides; oxidation and bearing corrosion inhibitors such as the metal dithiophosphates or the phosphorus pentasulfide pentene reaction products or the sulf-urized hydrocarbons; viscosity index improvers such as the polysiobutylenes; and pour point depressants of various types.
- silver Wear is fostered by the presence of sulfur compounds, generally from an organic compound, as exemplified by any of the foregoing sulfur-containing compounds, -or by various other materials such as octyl polysulfide, sulfochlorinated olefins, or sulfurized sperm or tall oils, etc.
- sulfur compounds generally from an organic compound, as exemplified by any of the foregoing sulfur-containing compounds, -or by various other materials such as octyl polysulfide, sulfochlorinated olefins, or sulfurized sperm or tall oils, etc.
- inclusion of the present silver wear inhibitors in amounts ranging from as little as 0.05 percent to about 3 percent or even more, depending upon the intrinsic wear tendencies of the lubricant and on the degree of improvement desired, will ordinarily suffice to provide sufficient inhibition against undue silver wear.
- the present additives may be prepared simply be reacting silicon disulfide with a ketone under anhydrous conditions.
- the temperature is advantageously around C., plus or minus about 50 C. and the reaction is advantageously conducted for sulficient time to permit substantially all of the hydrogen sulfide evolution to cease.
- an inert solvent that is, a normally liquid material which is inert with respect to the reactants and which does not deleteriously affect product quality.
- Example 1 This example illustrates the preparation of the reaction product of silicon disulfide with methyl-n-heptyl ketone.
- the hot mixture is filtered and the filtrate evaporated under vacuum to remove unreacted starting material.
- the resultant product is liquid at room temperature, and contains 0.10 weight percent silicon.
- the additive is also tested for oxidation inhibition under the conditions of the Stirring Sand Corrosion Test (S.S. C.T.).
- S.S. C.T. Stirring Sand Corrosion Test
- a copper-lead test specimen is likely abraded with steel wool, washed with naphtha, dried and weighed to the nearest milligram.
- the cleaned copperlead test specimen is suspended in a steel beaker, cleaned with a hot tri-sodium phosphate solution, rinsed with Water, acetone, and dried, and 250 grams of the oil to be tested, together with 0.625 gram lead oxide and 50 grams of a 30-35 mesh sand charged to the beaker.
- the beaker is then placed on a bath or heating block and heated to a temperature of 300 F.
- test specimen is then replaced in the beaker and an additional 0.375 gram of lead oxide added to the test oil.
- test specimen is again removed, rinsed and dried as before, and weighed.
- the test specimen is again placed in the beaker together with an additional 0.250 gram of lead oxide and the test continued for another 24 hours (72 hours total).
- the loss in weight of the test specimen is recorded after each weighing. A weight loss of 200 mg. or less in 48 hours, and 500 mg. or less in 72 hours in allowable.
- Example 2 Example 1 is repeated except that equal molar quantities of diphenyl ketone are employed. Again, excellent performance under the silver Falex test and in the S.S.C.T. are observed.
- Example 3 Example 1 is repeated, but with an equivalent quantity of methyl dodecyl ketone, and with methyl octadecyl ketone. In each instance excellent results are observed under the silver Falex test and the S.S.C.T.
- Example 4 hydrocarbon group attached to the carbonyl group. While the di'alkyl ketones are to be preferred, it is evident that the aryl, alkaryl, and even unsaturated ketones may likewise be employed, provided only that the additive has sufiicient solubility in the lubricant oil in question so as to afford adequate silver Wear inhibition.
- a hydrocarbon lubricant composition normally tending to cause excessive silver Wear and containing, in a minor amount sufficient to inhibit such wear, the oil soluble reaction product of silicon disulfide with a dialkyl ketone wherein each alkyl group contains from 1 to about 20 carbon atoms said reaction being carried out under anhydrous conditions at a temperature in the range of about to about C.
- composition of claim 1 wherein said ketone is methyl-n-heptyl ketone.
Description
United States Patent Oifice 3,192,164 Patented June 29, 1965 3,192,164 SILICON-CONTAINING LUBRICANT ADDITIVES Edwin L. De Young, Milwaukee, Wis., and Roger W.
Watson, Highland, Ind., assignors to Standard Oil Company, Chicago, ill., a corporation of Indiana No Drawing. Filed Jan. 16, 1962, Ser. No. 167,220 2 Claims. (Cl. 252.49.6)
This invention relates to certain ketones for inhibiting the tendency of hydrocarbon lubricant oils to cause excessive wear of silver and silver-containing bearings.
Many hydrocarbon lubricant oils contain sulfur compounds as oxidation or corrosion inhibitors. These sulfur compounds however promote excessive wear in silver and silver-containing bearings and bushings.
It is an object of the present invention to provide an additive for use in such lubricant compositions which tends to substantially inhibit excessive silver wear.
Briefly, in accordance with the invention, it has now been discovered that the reaction product of a ketone with silicon disulfide is an outstanding anti-silver wear additive when incorporated into hydrocarbon oils tending to cause excessive wear.
The present additives may be prepared simply by reacting the corresponding ketone, which is preferably a dialkyl ketone having from 1 to 20 carbon atoms in each alkyl group, with silicon disulfide under anhydrous conditions, and preferably at a temperature of about, say, 8-0-150 C., for sufficient time until hydrogen sulfide evolution ceases. The structural formula of the resultant product is not presently known, nor is it readily ascert'ainable. However, it has been definitely established that a reaction product having characteristics different from either reactant is obtained. Thus the preparation of the herein-described additives follows the technique of Fremy, Ann. Chim. Phys. (3), 38, 314 (1852), notwithstanding the statement by Malatesta, Gazz. Chim. Ital., 78, 753-63 (1948); Chemical Abstracts, 43, 4630 (1949), to the effect that SiS (does not) react with esters or ketones contrary to Fremy.
It has been discovered, in further accordance with the invention, that the present additives are outstanding with respect to imparting oxidation inhibition to lubricants containing them. Thus, not only is it possible to utilize the silver wear-inhibiting properties of the present additives to reduce the wear promotion of sulfur-containing oxidation inhibitors, but the amount of such oxidation inhibitors may likewise be reduced inasmuch as the present additives are themselves inhibitors against oxidation.
It appears that a wide variety of ketones may be employed herewith, although the dialkyl ketones, in which each alkyl group has from 1 to '20 carbon atoms, offering advantages With respect to ease of preparation, solubility, and effectiveness in inhibiting silver wear and oxidation. Examples of suitable dialkyl ketones include acetone, methyl n-propyl ketone, methyl isopropylene ketone, diethyl ketone, hexanone-Z, hexanone-3, methyl n-octyl ketone, etc. -Polyketones, including acetylacetone and acetonylacetone; unsaturated ketones such as mesityl oxide and phorone; halogenated ketones such as bromoacetone and chloroacetone; cyclic ketones such as diphenyl ketone and dinaphthyl ketones, may also be used, either alone or in admixture with each other.
Lubricant compositions which advantageously may be incorporated with the present additive are the hydrocarbon oils of suitable viscosity range, and which may contain various additives for different purposes. The hydrocarbon base may be either a natural or synthetic (e.g., propylene or isobutylene polymer) oil, suitably having a viscosity from about 20 S.S.U. at 100 to about 3,000 S.S.U. at 210. Additives commonly employed include detergents such as the metal sulfonates or metal phenyl sulfides; oxidation and bearing corrosion inhibitors such as the metal dithiophosphates or the phosphorus pentasulfide pentene reaction products or the sulf-urized hydrocarbons; viscosity index improvers such as the polysiobutylenes; and pour point depressants of various types. Ordinarily, silver Wear is fostered by the presence of sulfur compounds, generally from an organic compound, as exemplified by any of the foregoing sulfur-containing compounds, -or by various other materials such as octyl polysulfide, sulfochlorinated olefins, or sulfurized sperm or tall oils, etc. With these formulations, inclusion of the present silver wear inhibitors in amounts ranging from as little as 0.05 percent to about 3 percent or even more, depending upon the intrinsic wear tendencies of the lubricant and on the degree of improvement desired, will ordinarily suffice to provide sufficient inhibition against undue silver wear.
As indicated earlier, the present additives may be prepared simply be reacting silicon disulfide with a ketone under anhydrous conditions. The temperature is advantageously around C., plus or minus about 50 C. and the reaction is advantageously conducted for sulficient time to permit substantially all of the hydrogen sulfide evolution to cease. Under some circumstances it is advisable to conduct the reaction in the presence of an inert solvent, that is, a normally liquid material which is inert with respect to the reactants and which does not deleteriously affect product quality.
To illustrate and exemplify the present invention, the following examples are submitted. It is to be recognized that they are illustrative only, and are not to be considered wholly definitive with respect to scope or conditions.
Example 1 This example illustrates the preparation of the reaction product of silicon disulfide with methyl-n-heptyl ketone.
To a glass flask containing 14.2 grams (0.1 mol) of methyl-n-heptyl ketone is added 9.2 grams (0.1 mol) of finely powdered silicon disulfide. The mixture is heated with stirring at 100-110" C. for five hours until hydrogen sulfide is no longer evolved.
The hot mixture is filtered and the filtrate evaporated under vacuum to remove unreacted starting material. The resultant product is liquid at room temperature, and contains 0.10 weight percent silicon.
To test its efficacy for inhibiting excessive silver bearing wear, tests are conducted with the Falex tester (J our. Inst. Pet., 3-2, April 1946), utilizing a silver ball on steel wear surfaces. The control consists of a 73 viscosity index mineral lubricant base, containing 2.8 percent detergent (barium neutralized and hydrolyzed reaction product of phosphorus pentasulfide and a hydrocarbon), 1.0 weight percent calcium phenate and 0.2 percent sulfurized terpene. Under the conditions of the Falex test, the silver ball exhibits a weight loss of 275 milligrams.
By contrast, when the same lubricant composition is inhibited with only 0.5 weight percent of the above-described additive, the weight loss strikingly drops to 72.1 and 77.1 milligrams in duplicate tests.
The additive is also tested for oxidation inhibition under the conditions of the Stirring Sand Corrosion Test (S.S. C.T.). For this test, a copper-lead test specimen is likely abraded with steel wool, washed with naphtha, dried and weighed to the nearest milligram. The cleaned copperlead test specimen is suspended in a steel beaker, cleaned with a hot tri-sodium phosphate solution, rinsed with Water, acetone, and dried, and 250 grams of the oil to be tested, together with 0.625 gram lead oxide and 50 grams of a 30-35 mesh sand charged to the beaker. The beaker is then placed on a bath or heating block and heated to a temperature of 300 F. (plus or minus 2 F.) while the contents are stirred by means of a stirrer rotating at 750 rpm. The contents of the beaker are maintained at this 3 temperature for 24 hours, after which the copper-lead test specimen is removed, rinsed with naphtha, dried and weighed.
The test specimen is then replaced in the beaker and an additional 0.375 gram of lead oxide added to the test oil. At the end of an additional 24 hours of test operation the test specimen is again removed, rinsed and dried as before, and weighed. The test specimen is again placed in the beaker together with an additional 0.250 gram of lead oxide and the test continued for another 24 hours (72 hours total).
The loss in weight of the test specimen is recorded after each weighing. A weight loss of 200 mg. or less in 48 hours, and 500 mg. or less in 72 hours in allowable.
Utilizing a commercial heavy-duty S.A.E. 30 motor oil base and testing at 48 and at 72 hours, the respective weight losses when only 0.5 weight percent of the abovedescribed additive is employed, are 260.9 and 271.6.
Example 2 Example 1 is repeated except that equal molar quantities of diphenyl ketone are employed. Again, excellent performance under the silver Falex test and in the S.S.C.T. are observed.
Example 3 Example 1 is repeated, but with an equivalent quantity of methyl dodecyl ketone, and with methyl octadecyl ketone. In each instance excellent results are observed under the silver Falex test and the S.S.C.T.
Example 4 hydrocarbon group attached to the carbonyl group. While the di'alkyl ketones are to be preferred, it is evident that the aryl, alkaryl, and even unsaturated ketones may likewise be employed, provided only that the additive has sufiicient solubility in the lubricant oil in question so as to afford adequate silver Wear inhibition.
From the foregoing description it is manifest that there has been provided in accordance with the invention an outstanding additive for reducing, or inhibiting excessive silver wear characteristics of hydrocarbon lubricant oils normally tending to demonstrate excessive silver wear. While the invention has been described in conjunction with certain specific embodiments thereof, it will be appreciated that these are by way of illustration only, and that numerous alternatives, modifications, and variations will be evident to those skilled in the art in light of the foregoing description. Accordingly, it is intended to embrace all such alternatives, modifications, and variations as fall Within the spirit and broad scope of the appended claims.
We claim:
1. A hydrocarbon lubricant composition normally tending to cause excessive silver Wear and containing, in a minor amount sufficient to inhibit such wear, the oil soluble reaction product of silicon disulfide with a dialkyl ketone wherein each alkyl group contains from 1 to about 20 carbon atoms said reaction being carried out under anhydrous conditions at a temperature in the range of about to about C.
2. Composition of claim 1 wherein said ketone is methyl-n-heptyl ketone.
References Cited by the Examiner UNITED STATES PATENTS 2,588,083 3/52 Burkhard et a1 260448.2
DANIEL E. WYMAN, Primary Examiner.
ALPHONSO D. SULLIVAN, Examiner.
Claims (1)
1. A HYDROCARBON LUBRICANT COMPOSITION NORMALLY TENDING TO CAUSE EXCESSIVE SILVER WEAR AND CONTAINING, IN A MINOR AMOUNT SUFFICIENT TO INHIBIT SUCH WEAR, THE OIL SOLUBLE REACTION PRODUCT OF SILICON DISULFIDE WITH A DIALKYL KETONE WHEREIN EACH ALKYL GROUP CONTAINS FROM 1 TO ABOUT 20 CARBON ATOMS SAID REACTION BEING CARRIED OUT UNDER ANHYDROUS CONDITIONS AT A TEMPERATURE IN THE RANGE OF ABOUT 50 TO ABOUT 150*C.
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