GB963338A - Cadmium dialkyl dithiophosphate additives for lubricating oil compositions - Google Patents
Cadmium dialkyl dithiophosphate additives for lubricating oil compositionsInfo
- Publication number
- GB963338A GB963338A GB33984/60A GB3398460A GB963338A GB 963338 A GB963338 A GB 963338A GB 33984/60 A GB33984/60 A GB 33984/60A GB 3398460 A GB3398460 A GB 3398460A GB 963338 A GB963338 A GB 963338A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cadmium
- additives
- dialkyl
- dialkyl dithiophosphate
- reacting
- 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
- 239000000654 additive Substances 0.000 title abstract 5
- 229910052793 cadmium Inorganic materials 0.000 title abstract 5
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 title abstract 5
- 239000000203 mixture Substances 0.000 title abstract 4
- 239000010687 lubricating oil Substances 0.000 title abstract 3
- 239000003112 inhibitor Substances 0.000 abstract 5
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 abstract 4
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 abstract 4
- 238000006386 neutralization reaction Methods 0.000 abstract 4
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 abstract 3
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract 3
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 abstract 2
- 229940065285 cadmium compound Drugs 0.000 abstract 2
- 150000001662 cadmium compounds Chemical class 0.000 abstract 2
- 230000007797 corrosion Effects 0.000 abstract 2
- 238000005260 corrosion Methods 0.000 abstract 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 239000005069 Extreme pressure additive Substances 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001661 cadmium Chemical class 0.000 abstract 1
- 150000001702 camphene derivatives Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- -1 oxo diphenyl phosphate Chemical compound 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 229920002545 silicone oil Polymers 0.000 abstract 1
- 235000011044 succinic acid Nutrition 0.000 abstract 1
- 150000003444 succinic acids Chemical class 0.000 abstract 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
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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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
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- 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
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- 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
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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- 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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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated acids
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- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- 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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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
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- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/11—Complex polyesters
- C10M2209/112—Complex polyesters having dihydric acid centres
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/08—Halogenated waxes
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
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- 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
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- 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
- C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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- 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
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- 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
- C10M2223/042—Metal salts thereof
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- 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
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- C10M2229/02—Unspecified siloxanes; Silicones
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- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Abstract
The invention comprises a cadmium dialkyldithiophosphate prepared by reacting a secondary alkanol having 3 to 20 carbon atoms per molecule with phosphorus pentasulphide having a phosphorus content of from 26.0 to 27.8 weight per cent to form the corresponding dialkyl dithiophosphoric acid and converting this acid into the corresponding cadmium dialkyl dithiophosphate either by (a) neutralising it directly with a basic cadmium compound e.g. cadmium oxide or (b) by converting the acid into an alkali metal dialkyl dithiophosphate and reacting this by double decomposition with an inorganic cadmium salt. The secondary alkanol is preferably one containing 4 to 6 carbon atoms per molecule e.g. a mixture of secondary butanol and methyl isobutyl carbinol, and it is preferred to blow the intermediate dialkyl dithiophosphoric acid free of H2S with an inert gas, e.g. nitrogen, before reacting with the cadmium compound. When the neutralisation is carried out with cadmium oxide it is suitably effected at between 80 and 200 DEG F. Elemental sulphur may be added to the dialkyl dithiophosphoric acid immediately before the neutralisation step. The dialkyl dithiophosphoric acid is suitably prepared by reacting 4 moles of the alkanol with 1 mole of phosphorus pentasulphide at 160 to 200 DEG F. for about 1 to 6 hours and the product is generally filtered before the neutralisation step. Examples are given in which cadmium oxide is used in the neutralisation step, the phosphorus pentasulphide used has a phosphorus content of 27.5% and the secondary alkanols are methyl isobutyl carbinol and a mixture of secondary butanol and methyl isobutyl carbinol. A comparative example is also given in which a mixture of primary isobutyl and primary amyl alcohol is reacted with the P2S5 of 27.5% P content and the product neutralised with CdO to form the cadmium dialkyl dithiophosphate. The products are useful as additives for lubricants (see Division C5). Specification 932,961 is referred to.ALSO:A lubricating oil contains as additive a cadmium dialkyl dithiophosphate prepared in a specific manner (see Division C2). The lubricating oil is preferably a mineral oil, but may also be an animal, vegetable or synthetic oil. Examples of synthetic oils are diesters, complex esters, silicone oils and phosphorus derivatives, e.g. a C8 oxo diphenyl phosphate. Other additives may be present, e.g. corrosion or rust inhibitors, oxidation inhibitors, extreme pressure agents, pour point depressants, viscosity index improvers, detergent additives and antifoamants (e.g. a silicone fluid). Specified corrosion or rust inhibitors are mercaptoacetic acids of the formula R.S.CH2.COOH, wherein R is a branched C9-C17 alkyl group, monoalkenyl substituted succinic acids in which the alkenyl substituent contains 10 to 22 carbon atoms, and dinonyl naphthalene sulphonates. Specified oxidation inhibitors are the conventional phenolic and amine inhibitors and suitable extreme pressure additives are halogen-containing organic compounds, e.g. chlorinated wax and chlorinated camphene. Specification 932,961 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85046259A | 1959-11-02 | 1959-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB963338A true GB963338A (en) | 1964-07-08 |
Family
ID=25308174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33984/60A Expired GB963338A (en) | 1959-11-02 | 1960-10-04 | Cadmium dialkyl dithiophosphate additives for lubricating oil compositions |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1144865B (en) |
| GB (1) | GB963338A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0631389B2 (en) * | 1987-05-30 | 1994-04-27 | コスモ石油株式会社 | Fluid composition for viscous coupling |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2838555A (en) * | 1951-10-12 | 1958-06-10 | Lubrizol Corp | Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids |
| NL80939C (en) * | 1951-11-29 | |||
| NL86209C (en) * | 1952-03-08 | |||
| NL99849C (en) * | 1954-06-21 | |||
| GB804777A (en) * | 1956-06-08 | 1958-11-19 | Exxon Research Engineering Co | Fluorinated organic dithiophosphates and their use as anti-wear agents in lubricating oil compositions |
-
1960
- 1960-10-04 GB GB33984/60A patent/GB963338A/en not_active Expired
- 1960-10-06 DE DEE20009A patent/DE1144865B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1144865B (en) | 1963-03-07 |
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