GB882529A - Phosphorus-and sulphur-containing lubricant additives and their preparation - Google Patents
Phosphorus-and sulphur-containing lubricant additives and their preparationInfo
- Publication number
- GB882529A GB882529A GB7819/59A GB781959A GB882529A GB 882529 A GB882529 A GB 882529A GB 7819/59 A GB7819/59 A GB 7819/59A GB 781959 A GB781959 A GB 781959A GB 882529 A GB882529 A GB 882529A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alcohol
- terpene
- phosphorus
- mixture
- product
- Prior art date
- 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.)
- Expired
Links
- 239000003879 lubricant additive Substances 0.000 title abstract 3
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 10
- 229930195733 hydrocarbon Natural products 0.000 abstract 8
- 239000000203 mixture Substances 0.000 abstract 7
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 7
- 239000000047 product Substances 0.000 abstract 7
- 239000004215 Carbon black (E152) Substances 0.000 abstract 6
- 150000002430 hydrocarbons Chemical class 0.000 abstract 6
- 235000007586 terpenes Nutrition 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 4
- 230000002378 acidificating effect Effects 0.000 abstract 4
- 150000001298 alcohols Chemical class 0.000 abstract 4
- 229910052728 basic metal Inorganic materials 0.000 abstract 4
- 150000003818 basic metals Chemical class 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 239000000314 lubricant Substances 0.000 abstract 4
- 229910052751 metal Inorganic materials 0.000 abstract 4
- 239000002184 metal Substances 0.000 abstract 4
- 238000006386 neutralization reaction Methods 0.000 abstract 4
- 150000003505 terpenes Chemical class 0.000 abstract 4
- 229910052725 zinc Inorganic materials 0.000 abstract 4
- 239000011701 zinc Substances 0.000 abstract 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 3
- 239000007795 chemical reaction product Substances 0.000 abstract 3
- 239000002480 mineral oil Substances 0.000 abstract 3
- 239000011574 phosphorus Substances 0.000 abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 2
- 239000000654 additive Substances 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 239000004411 aluminium Substances 0.000 abstract 2
- 229910052782 aluminium Inorganic materials 0.000 abstract 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052788 barium Inorganic materials 0.000 abstract 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052790 beryllium Inorganic materials 0.000 abstract 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052793 cadmium Inorganic materials 0.000 abstract 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052791 calcium Inorganic materials 0.000 abstract 2
- 239000011575 calcium Substances 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 239000011651 chromium Substances 0.000 abstract 2
- 229910052804 chromium Inorganic materials 0.000 abstract 2
- 229910017052 cobalt Inorganic materials 0.000 abstract 2
- 239000010941 cobalt Substances 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- 238000000354 decomposition reaction Methods 0.000 abstract 2
- 239000011874 heated mixture Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000003112 inhibitor Substances 0.000 abstract 2
- 150000002484 inorganic compounds Chemical class 0.000 abstract 2
- 229910010272 inorganic material Inorganic materials 0.000 abstract 2
- 229910052742 iron Inorganic materials 0.000 abstract 2
- 239000011133 lead Substances 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 2
- 230000003472 neutralizing effect Effects 0.000 abstract 2
- 229910052759 nickel Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 229910052701 rubidium Inorganic materials 0.000 abstract 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000002002 slurry Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 229910052712 strontium Inorganic materials 0.000 abstract 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract 2
- -1 terpene hydrocarbon Chemical class 0.000 abstract 2
- 239000011135 tin Substances 0.000 abstract 2
- 229910052718 tin Inorganic materials 0.000 abstract 2
- 230000000996 additive effect Effects 0.000 abstract 1
- 239000002518 antifoaming agent Substances 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
Classifications
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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
- 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
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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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/04—Reaction products of phosphorus sulfur compounds with hydrocarbons
-
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- 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
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- C10N2010/02—Groups 1 or 11
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- C10N2010/00—Metal present as such or in compounds
- 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
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- C10N2010/08—Groups 4 or 14
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- C10N2010/14—Group 7
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- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/135—Steam engines or turbines
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/32—Wires, ropes or cables lubricants
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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
- C10N2040/34—Lubricating-sealants
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/36—Release agents or mold release agents
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/38—Conveyors or chain belts
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/40—Generators or electric motors in oil or gas winning field
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/42—Flashing oils or marking oils
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/44—Super vacuum or supercritical use
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- C10N2040/50—Medical uses
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- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
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- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
Abstract
Lubricant compositions comprise an additive prepared by heating a mixture of (1) a terpene hydrocarbon, (2) a monohydric saturated aliphatic or cycloaliphatic alcohol containing up to 18 carbon atoms and having at least one hydrogen on the carbon atom to which the hydroxyl group is attached, or a mixture of such alcohols, and (3) phosphorus pentasulphide (or elemental phosphorus and sulphur in the corresponding proportions), there being used a total of 1 to 2,5 moles of hydrocarbon and 1 to 3 moles of alcohol or alcohols per mole of sulphide, to a temperature in the range of about 70 DEG to about 150 DEG C., at which an acidic reaction product is formed; and then heating said product to a temperature in the range of about 60 DEG to about 150 DEG C. with an amount of a basic inorganic compound of a metal above hydrogen in the electromotive series sufficient to neutralize said product. The neutralizing agent may be an oxide, hydroxide, carbonate, bicarbonate or sulphide of lithium, rubidium, potassium, barium, strontium, calcium, sodium, magnesium, beryllium, aluminium, manganese, zinc, chromium, iron, cadmium, cobalt, nickel, tin or lead. Zinc is preferred. Compounds of the less basic metals may be made by double decomposition between a salt of such metal and a compound according to the invention with a more basic metal. The phosphorus pentasulphide may be added to the heated mixture of terpene and alcohol in portions. In a preferred embodiment, the terpene and alcohol are concurrently introduced into a slurry of phosphorus pentasulphide in an inert organic medium at about 90 DEG -150 DEG C. Suitable media include the less reactive hydrocarbons stripped from previous terpene-P2S5-alcohol reactions, hydrocarbon solvents, mineral oils and synthetic lubricants. After the reaction an additional 0,1 to about 0,8 mole per mole of P2S5 used of the same or a different alcohol may be introduced and the mixture heated further prior to neutralization. The intermediate acidic product may be treated with elemental sulphur prior to neutralization. The additives may be added to mineral oils or synthetic ester lubricants, generally in amount to give about 0,01 to about 0,5% by weight of phosphorus. A 4, 41-methylenebis-(2, 6-dialkylphenol) may be included. Thickeners, other inhibitors, detergent-dispersants, pour point depressants, viscosity index improvers, antifoam agents, rust inhibitors, oiliness or film strength agents or dyes may also be present.ALSO:Phosphorus pentasulphide reaction products useful as lubricant additives are prepared by heating a mixture of (1) a terpene hydrocarbon, (2) a monohydric saturated aliphatic or cycloaliphatic alcohol containing up to 18 carbon atoms and having at least one hydrogen on the carbon atom to which the hydroxyl group is attached, or a mixture of such alcohols, and (3) phosphorus pentasulphide (or elemental phosphorus and sulphur in the corresponding proportions), there being used a total of 1 to 2.5 moles of hydrocarbon and 1 to 3 moles of alcohol or alcohols per mole of sulphide, to a temperature in the range of about 70 DEG C. to about 150 DEG C., at which an acidic reaction product is formed; and then heating said product to a temperature in the range of about 60 DEG C. to about 150 DEG C. with an amount of a basic inorganic compound of a metal above hydrogen in the electromotive series sufficient to neutralise said product. The neutralising agent may be an oxide, hydroxide, carbonate, bicarbonate or sulphide of lithium, rubidium, potassium, barium, strontium, calcium, sodium, magnesium, beryllium, aluminium, manganese, zinc, chromium, iron, cadmium, cobalt, nickel, tin or lead. Zinc is preferred. Compounds of the less basic metals may be made by double decomposition between a salt of such metal and a compound according to the invention with a more basic metal. The phosphorus pentasulphide may be added to the heated mixture of terpene and alcohol in portions. In a preferred embodiment, the terpene and alcohol are concurrently introduced into a slurry of phosphorus pentasulphide in an inert organic medium at about 90 DEG C.-150 DEG C. Suitable media include the less reactive hydrocarbons stripped from previous terpene-P2S5-alcohol reactions, hydrocarbon solvents, mineral oils and synthetic lubricants. After the reaction an additional 0.1 to about 0.8 mole per mole of P2S5 used of the same or a different alcohol may be introduced and the mixture heated further prior to neutralisation. The intermediate acidic product may be treated with elemental sulphur prior to neutralisation. The products are used as lubricant additives (see Group III).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US882529XA | 1958-03-25 | 1958-03-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB882529A true GB882529A (en) | 1961-11-15 |
Family
ID=22210280
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7819/59A Expired GB882529A (en) | 1958-03-25 | 1959-03-06 | Phosphorus-and sulphur-containing lubricant additives and their preparation |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB882529A (en) |
-
1959
- 1959-03-06 GB GB7819/59A patent/GB882529A/en not_active Expired
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