GB687417A - Improvements in or relating to lubricating oil compositions - Google Patents
Improvements in or relating to lubricating oil compositionsInfo
- Publication number
- GB687417A GB687417A GB3082/50A GB308250A GB687417A GB 687417 A GB687417 A GB 687417A GB 3082/50 A GB3082/50 A GB 3082/50A GB 308250 A GB308250 A GB 308250A GB 687417 A GB687417 A GB 687417A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrocarbon
- hydrocarbons
- phosphorus
- aromatic
- lubricating oil
- 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
- 239000010687 lubricating oil Substances 0.000 title abstract 10
- 239000000203 mixture Substances 0.000 title abstract 7
- 229930195733 hydrocarbon Natural products 0.000 abstract 23
- 150000002430 hydrocarbons Chemical class 0.000 abstract 23
- 239000004215 Carbon black (E152) Substances 0.000 abstract 14
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 abstract 13
- -1 P2S3 Chemical class 0.000 abstract 11
- 239000000047 product Substances 0.000 abstract 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 8
- 239000002270 dispersing agent Substances 0.000 abstract 8
- 239000003208 petroleum Substances 0.000 abstract 7
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 abstract 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 6
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 abstract 6
- 229920000642 polymer Polymers 0.000 abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 5
- 239000000654 additive Substances 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 abstract 5
- 235000019271 petrolatum Nutrition 0.000 abstract 5
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- 150000001336 alkenes Chemical class 0.000 abstract 4
- 239000007795 chemical reaction product Substances 0.000 abstract 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 abstract 4
- 229910052751 metal Inorganic materials 0.000 abstract 4
- 239000002184 metal Substances 0.000 abstract 4
- 239000003921 oil Substances 0.000 abstract 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 4
- 239000001993 wax Substances 0.000 abstract 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 4
- 229910015900 BF3 Inorganic materials 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 3
- 239000000284 extract Substances 0.000 abstract 3
- 239000012188 paraffin wax Substances 0.000 abstract 3
- 235000019809 paraffin wax Nutrition 0.000 abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract 3
- 239000011574 phosphorus Substances 0.000 abstract 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 abstract 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 abstract 2
- KXYDGGNWZUHESZ-UHFFFAOYSA-N 4-(2,2,4-trimethyl-3h-chromen-4-yl)phenol Chemical compound C12=CC=CC=C2OC(C)(C)CC1(C)C1=CC=C(O)C=C1 KXYDGGNWZUHESZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 2
- 230000000996 additive effect Effects 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract 2
- 239000003963 antioxidant agent Substances 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 2
- 238000007664 blowing Methods 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000006229 carbon black Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 238000007334 copolymerization reaction Methods 0.000 abstract 2
- 238000005553 drilling Methods 0.000 abstract 2
- 238000005108 dry cleaning Methods 0.000 abstract 2
- 239000008396 flotation agent Substances 0.000 abstract 2
- 239000012530 fluid Substances 0.000 abstract 2
- 230000002140 halogenating effect Effects 0.000 abstract 2
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 abstract 2
- 229910001502 inorganic halide Inorganic materials 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 2
- 229910052742 iron Inorganic materials 0.000 abstract 2
- CIPXOBMYVWRNLL-UHFFFAOYSA-N isoterpinolene Chemical compound CC1CCC(=C(C)C)C=C1 CIPXOBMYVWRNLL-UHFFFAOYSA-N 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 235000010755 mineral Nutrition 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 239000012457 nonaqueous media Substances 0.000 abstract 2
- 239000003973 paint Substances 0.000 abstract 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 2
- 238000005554 pickling Methods 0.000 abstract 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 229920000098 polyolefin Polymers 0.000 abstract 2
- 239000001294 propane Substances 0.000 abstract 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 2
- 238000004073 vulcanization Methods 0.000 abstract 2
- 239000011592 zinc chloride Substances 0.000 abstract 2
- 235000005074 zinc chloride Nutrition 0.000 abstract 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 abstract 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 abstract 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003245 coal Substances 0.000 abstract 1
- 238000005336 cracking Methods 0.000 abstract 1
- 239000010779 crude oil Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- 229910001873 dinitrogen Inorganic materials 0.000 abstract 1
- 229940069096 dodecene Drugs 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 230000001050 lubricating effect Effects 0.000 abstract 1
- 239000010688 mineral lubricating oil Substances 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- 150000005673 monoalkenes Chemical class 0.000 abstract 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 abstract 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract 1
- 239000010690 paraffinic oil Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- 229920001083 polybutene Polymers 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 239000005061 synthetic rubber Substances 0.000 abstract 1
- 150000003505 terpenes Chemical class 0.000 abstract 1
- 235000007586 terpenes Nutrition 0.000 abstract 1
- 229940116411 terpineol Drugs 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N1/00—Linoleum, e.g. linoxyn, polymerised or oxidised resin
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5398—Phosphorus bound to sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
-
- C—CHEMISTRY; METALLURGY
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/043—Sulfur; Selenenium; Tellurium
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- 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
-
- 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
-
- 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
- C10M2205/20—Natural rubber; Natural resins
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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Abstract
A phosphorus and sulphur containing compound suitable as a lubricating oil additive (see Group III), is obtained by reacting at elevated temperature one molecular proportion of a phosphorus sulphide with one to ten, preferably two to five molecular proportions of a hydrocarbon and further reacting the acidic product thus formed with 0.1 to 50 per cent of its weight of a hydrocarbon containing at least one olefinic double bond. The preferred phosphorus sulphide is the pentasulphide but other phosphorus sulphides, e.g. P2S3, P4S3 and P4S7 may be used. Mixtures of two or more phosphorus sulphides may also be employed. The hydrocarbons which may be reacted with phosphorus sulphide may be paraffins, olefines, olefine polymers, diolefines, acetylenes, aromatic or alkyl aromatic hydrocarbons, cycloaliphatic hydrocarbons, petroleum fractions, such as lubricating oil fractions, petrolatums, waxes, cracked cycle stocks, condensation products of petroleum fractions, or solvent extracts of petroleum fractions. Essentially paraffinic hydrocarbons such as bright stock residuums and lubricating oil distillates may be employed as well as the products obtained by condensing any of the above paraffinic hydrocarbons, usually through first halogenating the hydrocarbon, with aromatic hydrocarbons in the presence of anhydrous inorganic halides such as aluminium chloride, zinc chloride, or boron fluoride. Several hydrocarbons are specified as starting materials (see Group IV (b)). The olefine polymers which may be used may be mono-olefine polymers of molecular weight ranging from 100 to 50,000 which may be obtained by the polymerization of low molecular weight monolefines such as ethylene, propylene, butylene, isobutylene, normal and isoamylenes, or hexenes, or by the copolymerization of any combination of these olefines. The copolymers of a low molecular weight olefine and a diolefine or a non-aromatic hydrocarbon of the formula CnH2n-x in which x is 2 or a multiple of 2 in the presence of a Friedel-Crafts or peroxide type catalyst may also be used, the low molecular weight olefine being preferably an isoolefine or a tertiary olefine, e.g. isobutylene; 2-methyl-butene-1; 2-ethylbutene-1, secondary and tertiary amylenes and hexylenes. The non-aromatic hydrocarbon may be a conjugated diolefine, e.g. butadiene, isoprene, cyclopentadiene, 2,3-dimethylbutadiene, pentadiene-1,3, and hexadiene-2,4, or a diolefine such as 1,4-hexadiene in which the double bond is not conjugated, as well as the acetylenes. The copolymerization is preferably carried out in the presence of aluminium chloride, boron fluoride or benzoyl peroxide and the copolymer preferably has a molecular weight of 1,000 to 30,000. The phosphorus sulphide reaction product may be further treated by blowing with steam, alcohol, ammonia, or an amine at 200 DEG to 600 DEG F. to improve the odour thereof. The product obtained by reacting the hydrocarbon with a phosphorus sulphide is then further reacted with an unsaturated hydrocarbon which may be any aliphatic, cycloaliphatic, terpenic or aliphatic aromatic hydrocarbon containing at least one double carbon-carbon linkage in a non-aromatic group, e.g. the olefines such as propylene, the isomeric butylenes, diisobutylenes, triisobutylenes, the codimer of isobutylene and n-butylene, cracked gasoline fractions, cracked paraffin wax, viscous olefine polymers such as medium or high molecular weight polybutene; cyclopentene, cyclohexene, butadiene, pentadiene, isoprene, dipentene, a -pinene, b -pinene, terpinolene, D 2,4(8)-p-menthadiene and styrene. The further treatment with the olefinic hydrocarbon may be effected at room temperature or preferably at 150-380 DEG F. An excess of the olefinic hydrocarbon may be employed in which case a quantity of sulphur is then added, preferably with the addition of a vulcanizing accelerator. The additives may be blended with lubricating oils which may be synthetic oils prepared by the polymerization olefines. The additives may also be used in dry cleaning fluids, in mineral spirit and aqueous paints, as flotation agents, as dispersants for insecticides in aqueous and non-aqueous solutions, as additives for synthetic rubber, as carbon black dispersants, as vulcanization accelerators, and as metal dispersants and antioxidants in colloidal iron electromagnetic clutches. They are also useful dispersants in printing ink, asphalts, linoleum, roofing compositions, drilling muds, metal cleaners and pickling solutions.ALSO:A phosphorus and sulphur-containing compound suitable as a lubricating oil additive (see Group III) is obtained by reacting at elevated temperature one molecular proportion of a phosphorus sulphide with one to ten, preferably two to five molecular proportions of a hydrocarbon and further reacting the acidic product thus formed with 0.1 to 50 per cent of its weight of a hydrocarbon containing at least one olefinic double bond. The preferred phosphorus sulphide is the pentasulphide (P2S5) but other phosphorus sulphides, e.g. P2S3, P4S3 and P4S7 may be used. Mixtures of two or more phosphorus sulphides may also be employed. The hydrocarbon which may be reacted with the phosphorus sulphide may be paraffins, olefins, olefine polymers (see Group IV (a)), diolefines, acetylenes, aromatic or alkyl aromatic hydrocarbons, cycloaliphatic hydrocarbons, petroleum fractions, such as lubricating oil fractions, petrolatums, waxes, cracked cycle stocks, condensation products of petroleum fractions, or solvent extracts of petroleum fractions. Essentially paraffinic hydrocarbons such as bright stock residuums and lubricating oil distillates may be employed, as well as products obtained by condensing any of the above paraffinic hydrocarbons usually through first halogenating the hydrocarbon, with aromatic hydrocarbons in the presence of anhydrous inorganic halides, such as aluminium chloride, zinc chloride or boron fluoride. Specified olefines are isobutylene, decene, dodecene, cetene (C16), octadecene, cerotene, melene, olefinic extracts from gasoline or gasoline itself, cracked cycle stocks and polymers thereof, resin oils from crude oil, hydrocarbon coal resins, cracked waxes, dehydrohalogenated chlorinated waxes, and any mixed high molecular weight alkenes obtained by cracking petroleum oils. It is preferred to use olefines having at least 20 carbon atoms per molecule, of which from 12 to 18 carbon atoms are in a long chain, e.g. the olefins obtained by dehydrogenation of paraffin waxes, by the dehydrohalogenation of long-chain alkyl halides, by the synthesis of hydrocarbons from CO and H2, or by dehydration of alcohols. Other suitable olefins are the mono-olefin polymers (see Group IV (a)), and diolefines such as butadiene, isoprene, cyclopentadiene, 2,3-dimethylbutadiene; pentadiene-1,3; hexadiene-2,4; and terpenes. Acetylene and substituted acetylenes may also be employed. Other hydrocarbons which may be used are aromatic hydrocarbons such as benzene, naphthalene, anthracene, toluene, xylene and diphenyl, as well as aromatic hydrocarbons having alkyl substituents and aliphatic hydrocarbons having aryl substituents. A resin-like oil of high molecular weight obtained preferably from a paraffinic oil which has been dewaxed and then treated with a liquefied normally gaseous hydrocarbon, e.g. propane, to precipitate a heavy propane insoluble fraction may also be used. The phosphorus sulphide may be reacted with the hydrocarbon at 200 DEG to 600 DEG F., preferably in a non-oxidizing atmosphere, e.g. of nitrogen. If desired, the reaction product may be further treated by blowing with steam, alcohol, ammonia, or an amine, at 200 DEG to 600 DEG F. to improve the odour thereof. The reaction product is then reacted with the unsaturated hydrocarbon and this may be effected at room temperature or preferably at 150-380 DEG F. An excess of the unsaturated hydrocarbon may be employed in which case a quantity of sulphur is then added, preferably with the addition of a vulcanization accelerator. The unsaturated hydrocarbon which is reacted with the phosphorus sulphide-hydrocarbon reaction product may be any aliphatic, cycloaliphatic, terpenic or aliphatic-aromatic hydrocarbon containing at least one double bond carbon-to-carbon linkage in a non-aromatic group, e.g. the olefines such as propylene, the isomeric butylenes, diisobutylenes, triisobutylenes, the codimer of isobutylene and n-butylene, cracked gasoline fractions, cracked paraffin wax, viscous olefin polymers (see Group IV (a)), cyclopentene, cyclohexene, butadiene, pentadiene, isoprene, dipentene, a -pinene, b -pinene, terpinolene, D 2,4(8)-p.-menthadiene and styrene. In examples: (1) phosphorus pentasulphide is reacted at 350-370 DEG F. and in an atmosphere of nitrogen with a lubricating oil bright stock in the presence of benzoyl peroxide and the product is then heated with diisobutylene, nitrogen gas being bubbled through the reaction mixture; (2) as in (1) except that commercial dipentene (a mixture of terpinolene and a -pinene containing small amounts of a -pinene, a -terpineol, D -2,4(8)-p-menthadiene, and para-cymene) is used instead of diisobutylene. The products in addition to being employed in lubricants may also be used in other mineral oil products and also have practical use in dry cleaning fluids, mineral spirit and aqueous paints, as flotation agents, as dispersants for insecticides in aqueous and non-aqueous solutions, as carbon black dispersants, and as metal dispersants and antioxidants in colloidal iron electromagnetic clutches. They are also useful dispersants in printing ink, asphalts, linoleum, roofing compositions, drilling muds, metal cleaners and pickling solutions.ALSO:A lubricating composition comprises a lubricating oil, preferably a mineral lubricating oil, containing a detergent quantity of a product obtained by reacting
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US129196A US2640053A (en) | 1949-11-23 | 1949-11-23 | Compounded lubricating oil |
Publications (1)
Publication Number | Publication Date |
---|---|
GB687417A true GB687417A (en) | 1953-02-11 |
Family
ID=22438849
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3082/50A Expired GB687417A (en) | 1949-11-23 | 1950-02-07 | Improvements in or relating to lubricating oil compositions |
Country Status (5)
Country | Link |
---|---|
US (1) | US2640053A (en) |
BE (1) | BE512916A (en) |
FR (1) | FR1039565A (en) |
GB (1) | GB687417A (en) |
NL (1) | NL76151C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1038689B (en) * | 1956-08-23 | 1958-09-11 | Exxon Research Engineering Co | Process for the production of phosphorus sulphurized lubricating oil additives |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2712528A (en) * | 1951-11-01 | 1955-07-05 | Exxon Research Engineering Co | Mineral oil composition containing an improved hydrocarbon-phosphorus sulfide reaction product |
US2768999A (en) * | 1952-08-27 | 1956-10-30 | Exxon Research Engineering Co | Phosphosulfurized hydrocarbons and production thereof |
US2768954A (en) * | 1952-12-30 | 1956-10-30 | Standard Oil Co | Lubricant |
US2773037A (en) * | 1953-03-27 | 1956-12-04 | Tidewater Oil Company | Concentrates useful as additives in mineral oil compositions and mineral oil compositions containing same |
US2800467A (en) * | 1953-10-21 | 1957-07-23 | Socony Mobil Oil Co Inc | Phosphorus sesquisulfide-olefin-organic peroxide reaction products and method of preparation thereof |
US2804431A (en) * | 1955-04-18 | 1957-08-27 | Exxon Research Engineering Co | Stabilization of phosphosulfurized hydrocarbons |
US2839471A (en) * | 1955-05-17 | 1958-06-17 | Exxon Research Engineering Co | Extreme pressure lubricants |
US3006850A (en) * | 1956-10-31 | 1961-10-31 | Standard Oil Co | Rust preventive composition |
GB1469622A (en) * | 1974-03-20 | 1977-04-06 | Exxon Research Engineering Co | Olefin sulphide reaction products their derivatives and use thereof as oil and fuel additives |
US4906391A (en) * | 1986-09-15 | 1990-03-06 | Mobil Oil Corporation | Reaction products of olefins, sulfur and phosphorus pentasulfide and lubricant compositions thereof |
US5026493A (en) * | 1989-08-03 | 1991-06-25 | Ethyl Petroleum Additives, Inc. | Reduced ash content lubricants |
CN104383832A (en) * | 2014-11-04 | 2015-03-04 | 无锡市华明化工有限公司 | Additive mother liquor preparation device for lubricating oil production |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2356073A (en) * | 1944-08-15 | Reaction products of aliphatic alco | ||
US2315529A (en) * | 1941-03-24 | 1943-04-06 | Standard Oil Co | Phosphorus sulphide-hydrocarbon reaction product |
US2379312A (en) * | 1944-07-15 | 1945-06-26 | Sinclair Refining Co | Reaction products of alkylated phenols and terpene-phosphorus sulphide |
US2413648A (en) * | 1945-06-28 | 1946-12-31 | Hercules Powder Co Ltd | Terpene reaction product and method of producing |
US2483600A (en) * | 1946-05-16 | 1949-10-04 | Pure Oil Co | Preparation of high-viscosity extreme pressure base by airblowing |
US2507731A (en) * | 1947-10-17 | 1950-05-16 | Standard Oil Co | Process of reacting phosphorus sulfide and olefinic hydrocarbon |
-
0
- BE BE512916D patent/BE512916A/xx unknown
- NL NL76151D patent/NL76151C/xx active
-
1949
- 1949-11-23 US US129196A patent/US2640053A/en not_active Expired - Lifetime
-
1950
- 1950-02-07 GB GB3082/50A patent/GB687417A/en not_active Expired
- 1950-10-24 FR FR1039565D patent/FR1039565A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1038689B (en) * | 1956-08-23 | 1958-09-11 | Exxon Research Engineering Co | Process for the production of phosphorus sulphurized lubricating oil additives |
Also Published As
Publication number | Publication date |
---|---|
BE512916A (en) | |
FR1039565A (en) | 1953-10-08 |
NL76151C (en) | |
US2640053A (en) | 1953-05-26 |
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