GB727573A - Improvements in or relating to phospho-sulphurisation of organic materials - Google Patents
Improvements in or relating to phospho-sulphurisation of organic materialsInfo
- Publication number
- GB727573A GB727573A GB1799851A GB1799851A GB727573A GB 727573 A GB727573 A GB 727573A GB 1799851 A GB1799851 A GB 1799851A GB 1799851 A GB1799851 A GB 1799851A GB 727573 A GB727573 A GB 727573A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorus
- reaction
- oils
- oil
- mixture
- 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
- 239000011368 organic material Substances 0.000 title abstract 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 8
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 abstract 7
- -1 diolefines Chemical class 0.000 abstract 6
- 229930195733 hydrocarbon Natural products 0.000 abstract 6
- 150000002430 hydrocarbons Chemical class 0.000 abstract 6
- 239000000463 material Substances 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 6
- 239000000047 product Substances 0.000 abstract 6
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
- 238000000034 method Methods 0.000 abstract 4
- 239000003921 oil Substances 0.000 abstract 4
- 235000019198 oils Nutrition 0.000 abstract 4
- 239000011574 phosphorus Substances 0.000 abstract 4
- 229910052698 phosphorus Inorganic materials 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 3
- 239000010687 lubricating oil Substances 0.000 abstract 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 3
- 239000007787 solid Substances 0.000 abstract 3
- 235000013311 vegetables Nutrition 0.000 abstract 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 abstract 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 abstract 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract 2
- 239000000654 additive Substances 0.000 abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 2
- IXWIAFSBWGYQOE-UHFFFAOYSA-M aluminum;magnesium;oxygen(2-);silicon(4+);hydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Mg+2].[Al+3].[Si+4].[Si+4].[Si+4].[Si+4] IXWIAFSBWGYQOE-UHFFFAOYSA-M 0.000 abstract 2
- 229910052639 augite Inorganic materials 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 239000011449 brick Substances 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000005336 cracking Methods 0.000 abstract 2
- 238000000354 decomposition reaction Methods 0.000 abstract 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 abstract 2
- 229960005215 dichloroacetic acid Drugs 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 239000000428 dust Substances 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 239000010685 fatty oil Substances 0.000 abstract 2
- 150000008282 halocarbons Chemical class 0.000 abstract 2
- 239000011261 inert gas Substances 0.000 abstract 2
- 239000000787 lecithin Substances 0.000 abstract 2
- 229940067606 lecithin Drugs 0.000 abstract 2
- 235000010445 lecithin Nutrition 0.000 abstract 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000000395 magnesium oxide Substances 0.000 abstract 2
- 239000010445 mica Substances 0.000 abstract 2
- 229910052618 mica group Inorganic materials 0.000 abstract 2
- 239000010688 mineral lubricating oil Substances 0.000 abstract 2
- 239000002480 mineral oil Substances 0.000 abstract 2
- 239000012184 mineral wax Substances 0.000 abstract 2
- 239000012188 paraffin wax Substances 0.000 abstract 2
- 239000003208 petroleum Substances 0.000 abstract 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 2
- 150000003097 polyterpenes Chemical class 0.000 abstract 2
- 239000008262 pumice Substances 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 239000011435 rock Substances 0.000 abstract 2
- 239000004576 sand Substances 0.000 abstract 2
- 239000000741 silica gel Substances 0.000 abstract 2
- 229910002027 silica gel Inorganic materials 0.000 abstract 2
- 150000003505 terpenes Chemical class 0.000 abstract 2
- 235000007586 terpenes Nutrition 0.000 abstract 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 abstract 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 2
- 239000012178 vegetable wax Substances 0.000 abstract 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 abstract 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 abstract 1
- 244000180278 Copernicia prunifera Species 0.000 abstract 1
- 235000010919 Copernicia prunifera Nutrition 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000010699 lard oil Substances 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- 235000021388 linseed oil Nutrition 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- 229910052901 montmorillonite Inorganic materials 0.000 abstract 1
- 239000004006 olive oil Substances 0.000 abstract 1
- 235000008390 olive oil Nutrition 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 239000012169 petroleum derived wax Substances 0.000 abstract 1
- 235000019381 petroleum wax Nutrition 0.000 abstract 1
- 229920000098 polyolefin Polymers 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000011819 refractory material Substances 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 229940084106 spermaceti Drugs 0.000 abstract 1
- 239000012177 spermaceti Substances 0.000 abstract 1
- 239000001993 wax Substances 0.000 abstract 1
Classifications
-
- 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
- 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
- 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
- C10M2207/28—Esters
-
- 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
- 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
- C10M2225/041—Hydrocarbon polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- 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
In a process for reacting a phosphorus sulphide, or a mixture of phosphorus sulphides, or a mixture of phosphorus and sulphur with organic materials known to react therewith, the process is carried out in the presence of a finely divided, inert, refractory, dispersed solid. The refractory materials used as dispersed solids are those which do not react with the reactants or reaction products and include sand, silica gel, clays such as attapulgus clay or moutmorillonite, brick dust, powdered silicate rocks, e.g. felspar, augite and mica; pumice, kieselguhr and cracking catalyst (synthetic silica-magnesia or silica-alumina). The organic materials that may be used are preferably predominantly hydrocarbon materials such as paraffins, olefins or olefin polymers, diolefines, acetylenes, aromatics, alkyl aromatics, cyclic aliphatics, liquid hydrocarbons derived from mineral oil such as naphthas, gas oils or lubricating oils, petroleum waxes, cracked cycle stocks, condensation products of petroleum fractions, bright stock residuum, lubricating oil distillates, and Friedel-Crafts condensates of halogenated hydrocarbons and aromatics and particularly mineral lubricating oil bright stocks which may be untreated petroleum fractions or residue, or oils refined by any conventional treatment such as dewaxing, solvent extractions and deasphalting. Other compounds which may be used include fatty bodies such as fatty oils-animal, vegetable and marine such as sperm oil, lard oil, linseed oil, and olive oil, fatty acids, sulphurized fatty oils, halogenated hydrocarbons, terpenes, such as alpha pinene and dipentene, polyterpenes, rosin, vegetable and mineral waxes such as spermaceti, carnauba and candellila waxes, ceresine, lanoline, lecithin and paraffin wax. The inert material should preferably have a particle size between 100 and 20 mesh and is preferably used in an amount of between 1 and 5 per cent by weight. The phosphosulphurization may be effected by heating the components at 200 DEG to 600 DEG F., preferably 300 DEG to 550 DEG F. using about 1 to 10 parts by weight of organic material to one of the phosphosulphurization reagent. The products may be further reacted with a predominantly hydrocarbon material containing at least one olefinic double bond, e.g. as disclosed in Specifications 687,417 and 713,337 respectively. Any or all of the steps disclosed in Specification 717,675 may also be included in the present process. These steps involve heating the phosphorus sulphide or mixture of elemental phosphorus and sulphur to a temperature between 212 DEG F. and the boiling or decomposition temperature thereof prior to the phosphosulphurization, passing a stream of inert gas through the reaction mixture during the phosphosulphurization and maintaining the phosphosulphurized product at between 212 DEG F. and 400 DEG F. prior to reaction with the unsaturated hydrocarbon containing at least one olefinic double bond. Specified phosphorus sulphides are the pentasulphide, trisulphide, sesquisulphide, disulphide and heptasulphide. A table is given to show that the reaction time is reduced when phosphorus pentasulphide is reacted with a mid-Continent bright stock in the presence of 3 per cent by weight of powdered fuller's earth as compared with reaction in the absence of the earth.ALSO:In the production of additives for use in lubricating oils by reacting a phosphorus sulphide or a mixture of phosphorus sulphides, or a mixture of phosphorus and sulphur, with organic materials known to react therewith, the reaction is carried out in the presence of a finely divided, inert, refractory, dispersed solid, e.g. sand, silica gel, clays such as attapulgus clay or montmorillonite, brick dust, powdered silicate rocks, e.g. felspar, augite and mica; pumice, kieselguhr and cracking catalyst (i.e. synthetic silica magnesia or synthetic silica-alumina). The preferred organic material is a predominantly hydrocarbon material such as a mineral lubricating oil bright stock, but several other materials may be used, including hydrocarbons, fatty oils, fatty acids, terpenes, polyterpenes, rosin, vegetable and mineral waxes, ceresine, lanoline, lecithin and paraffin wax (see Group IV (b)). When the products are to be dissolved in mineral oils the reactants should be chosen so as to give a product soluble in the oil base or which can be brought into solution with the aid of solubilizing agents such as esters or alcohols of high molecular weight. The products may be further reacted with a predominantly hydrocarbon material containing at least one olefinic double bond,e.g. as disclosed in Specifications 687,417 and 713,337. A table is given to show the properties of the additive obtained by reacting a mid-Continent bright stock with phosphorus pentasulphide in the presence of 3 per cent. by weight of Fuller's earth. Specification 717,675 is also referred to and it is stated that any of the steps disclosed in the latter may be included in the present process. These steps involve heating the phosphorus sulphide or mixture of phosphorus and sulphur to a temperature between 212 DEG F. and the boiling or decomposition temperature thereof, prior to the phosphosulphurization reaction, passing a stream of inert gas through the reaction mixture during the phosphosulphurization, and maintaining the phosphosulphurized product at between 212 DEG F. and 400 DEG F. prior to reaction with the unsaturated hydrocarbon containing at least one olefinic double bond.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1799851A GB727573A (en) | 1951-07-30 | 1951-07-30 | Improvements in or relating to phospho-sulphurisation of organic materials |
FR1061000D FR1061000A (en) | 1951-07-30 | 1952-07-24 | Lubricating oil additions |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1799851A GB727573A (en) | 1951-07-30 | 1951-07-30 | Improvements in or relating to phospho-sulphurisation of organic materials |
Publications (1)
Publication Number | Publication Date |
---|---|
GB727573A true GB727573A (en) | 1955-04-06 |
Family
ID=10104857
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1799851A Expired GB727573A (en) | 1951-07-30 | 1951-07-30 | Improvements in or relating to phospho-sulphurisation of organic materials |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR1061000A (en) |
GB (1) | GB727573A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995026357A1 (en) * | 1994-03-29 | 1995-10-05 | Monsanto Company | Thionation process using elemental phosphorus and sulfur |
-
1951
- 1951-07-30 GB GB1799851A patent/GB727573A/en not_active Expired
-
1952
- 1952-07-24 FR FR1061000D patent/FR1061000A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995026357A1 (en) * | 1994-03-29 | 1995-10-05 | Monsanto Company | Thionation process using elemental phosphorus and sulfur |
Also Published As
Publication number | Publication date |
---|---|
FR1061000A (en) | 1954-04-07 |
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