GB874747A - Zinc salts of mixed dialkyl dithiophosphoric acids and lubricating compositions containing them - Google Patents
Zinc salts of mixed dialkyl dithiophosphoric acids and lubricating compositions containing themInfo
- Publication number
- GB874747A GB874747A GB10394/58A GB1039458A GB874747A GB 874747 A GB874747 A GB 874747A GB 10394/58 A GB10394/58 A GB 10394/58A GB 1039458 A GB1039458 A GB 1039458A GB 874747 A GB874747 A GB 874747A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mixture
- alcohol
- heated
- ester
- dialkyl dithiophosphoric
- 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
- 239000000203 mixture Substances 0.000 title abstract 20
- 239000002253 acid Substances 0.000 title abstract 7
- 150000007513 acids Chemical class 0.000 title abstract 7
- 230000001050 lubricating effect Effects 0.000 title abstract 3
- 150000003751 zinc Chemical class 0.000 title abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 5
- 150000001298 alcohols Chemical class 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- 238000010438 heat treatment Methods 0.000 abstract 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 4
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 abstract 4
- 150000003752 zinc compounds Chemical class 0.000 abstract 4
- 239000011787 zinc oxide Substances 0.000 abstract 4
- 238000005292 vacuum distillation Methods 0.000 abstract 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000654 additive Substances 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 230000000052 comparative effect Effects 0.000 abstract 2
- SZXCCXFNQHQRGF-UHFFFAOYSA-N di(propan-2-yloxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)OP(S)(=S)OC(C)C SZXCCXFNQHQRGF-UHFFFAOYSA-N 0.000 abstract 2
- -1 di-methyl isobutyl Chemical group 0.000 abstract 2
- 239000010687 lubricating oil Substances 0.000 abstract 2
- 230000003472 neutralizing effect Effects 0.000 abstract 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 2
- 239000011701 zinc Substances 0.000 abstract 2
- 229910052725 zinc Inorganic materials 0.000 abstract 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 238000013019 agitation Methods 0.000 abstract 1
- 229910052788 barium Inorganic materials 0.000 abstract 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- GQCQJECYDYZWHI-UHFFFAOYSA-N didecoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCCCCCCOP(S)(=S)OCCCCCCCCCC GQCQJECYDYZWHI-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000003879 lubricant additive Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 1
- 239000003039 volatile agent Substances 0.000 abstract 1
- 229940007718 zinc hydroxide Drugs 0.000 abstract 1
- 229910021511 zinc hydroxide Inorganic materials 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2040/02—Bearings
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Lubricants (AREA)
Abstract
A zinc mixed dialkyl dithiophosphate useful as an additive for lubricating oils (see Group III) is obtained by heating a mixture of at least two separately prepared different simple or homogeneous dialkyl dithiophosphoric acids with a saturated aliphatic alcohol, neutralising the resulting product with a reactive zinc compound and then stripping off any uncombined alcohol by vacuum distillation. The preferred dialkyl dithiophosphoric acid mixture is one in which one ester contains two identical alkyl radicals of 1 to 6 carbon atoms and the other ester is a different bis-ester containing two identical alkyl radicals of 3 to 10 carbon atoms. The alcohol with which the mixture is heated is preferably a C1-6 alcohol and this alcohol may be the same as or different from either of the alcohols used in preparing the mixture of the dialkyl dithiophosphoric acids and is preferably the same as the alcohol used in preparing the bis ester of low molecular weight. It is preferred to add a C1C6 saturated aliphatic alcohol in an amount ranging from 1% to about 15% based on the weight of the mixture of dialkyl dithiophosphoric acids and the resulting mixture is then heated usually for about 0.5 to 3 hours at a temperature depending on the boiling point of the added alcohol, e.g. in the case of isopropanol a suitable heating temperature is between about 65.6 DEG C. and the boiling point of isopropanol. After the heat treatment the mixture is preferably cooled and a reactive zinc compound, e.g. zinc oxide or hydroxide, in added with agitation and the mixture heated until neutralisation is complete. An excess of the zinc compound is preferably employed. The mixture is finally stripped free from uncombined alcohols and other volatiles by vacuum distillation and is then filtered free from solids and cooled. In typical examples di-methyl isobutyl carbinyl dithiophosphoric acid (or di-n-decyl dithiophosphoric acid) and di-isopropyl dithiophosphoric acid are prepared separately by heating the corresponding alcohol with phosphorus pentasulphide and are then mixed together, the mixture heated with isopropanol at 76.7 DEG C. and then reacted with zinc oxide at elevated temperature, the mixture being finally vacuum stripped and then filtered. Examples are also given in which n-butyl alcohol and ethanol respectively are heated with a mixture of di-isobutyl carbinyl- and diisopropyl-dithiophosphoric acid and the mixture neutralised with zinc oxide. A comparative example is also given in which a mixture of isobutylcarbinol and isopropyl alcohol is heated with P2S5 and the mixed dialkyldithiophosphoric acids neutralised with zinc oxide.ALSO:A lubricating composition comprises a hydrocarbon oil of lubricating viscosity having dissolved therein a zinc mixed dialkyl dithiophosphate obtained by heating a mixture of simple or homogeneous dialkyl dithiophosphoric acids with a saturated aliphatic alcohol, neutralising the resulting product with a reactive zinc compound and then stripping off any uncombined alcohol by vacuum distillation (see Group IV(b)). The preferred dialkyl dithiophosphoric acid mixture is one in which one ester contains two identical C1-C6 alkyl radicals (e.g. isopropyl) and the other ester is a different bis-ester containing two identical C3-C10 alkyl radicals (e.g. isobutylcarbinyl or n-decyl). The alcohol with which the mixture is heated is preferably a C1-C6 aliphatic alcohol, e.g. ethanol, isopropanol or n-butanol and this alcohol may be the same as or different from either of the alcohols corresponding to the alkyl radicals in the mixed dialkyl dithiophosphoric acids. Other lubricating oil additives may be present, e.g. calcium or barium petroleum sulphonates. Reference is also made for comparative purposes to the use as lubricant additive of the zinc salt derived from a mixed dialkyl dithiophosphoric acid obtained by reacting a mixture of methyl isobutyl carbinol and isopropanol with phosphorus pentasulphide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US874747XA | 1957-04-18 | 1957-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB874747A true GB874747A (en) | 1961-08-10 |
Family
ID=22205403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10394/58A Expired GB874747A (en) | 1957-04-18 | 1958-04-01 | Zinc salts of mixed dialkyl dithiophosphoric acids and lubricating compositions containing them |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE566824A (en) |
| DE (1) | DE1112067B (en) |
| GB (1) | GB874747A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4438611A1 (en) * | 2023-03-31 | 2024-10-02 | Afton Chemical Corporation | Thiophosphoric acid products for antiwear additives |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL269607A (en) * | 1960-09-30 | |||
| NL271182A (en) * | 1960-11-17 | |||
| NL136076C (en) * | 1962-09-07 | |||
| US4116871A (en) * | 1977-06-29 | 1978-09-26 | Chevron Research Company | Preparation of phosphorus-containing acids and salts |
| US12110468B1 (en) * | 2023-03-22 | 2024-10-08 | Afton Chemical Corporation | Antiwear systems for improved wear in medium and/or heavy duty diesel engines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL85589C (en) * | 1951-03-29 |
-
0
- BE BE566824D patent/BE566824A/xx unknown
-
1958
- 1958-04-01 GB GB10394/58A patent/GB874747A/en not_active Expired
- 1958-04-16 DE DEA29270A patent/DE1112067B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4438611A1 (en) * | 2023-03-31 | 2024-10-02 | Afton Chemical Corporation | Thiophosphoric acid products for antiwear additives |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1112067B (en) | 1961-08-03 |
| BE566824A (en) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE847897C (en) | Process for the preparation of dithiophosphoric acid triesters | |
| US2680123A (en) | Zinc salt of mixed ester thiophosphates | |
| US3770854A (en) | Process for preparing phosphor disulphides | |
| US2586655A (en) | S-alkoxymethyl-o, o'-dialkyldithiophosphates | |
| GB1055429A (en) | Organic polymeric salts and lubricating oil compostitions containing such salts | |
| US3290347A (en) | Preparation of polyvalent metal salts of diorgano dithiophosphoric acids | |
| DE2513965A1 (en) | METAL PHOSPHORUS ACID MONOESTER COMPOUNDS | |
| GB959115A (en) | Zinc carboxylate-coordinated zinc dithiophosphates and lubricating oil compositions containing them | |
| GB874747A (en) | Zinc salts of mixed dialkyl dithiophosphoric acids and lubricating compositions containing them | |
| US3691220A (en) | Process for preparing overbased zinc phosphorodithioates | |
| US2373811A (en) | Complex dithiophosphoric acid esters | |
| US2973323A (en) | Lubricating oil composition containing heterocyclic polyamine salts of partial ester of phosphorodithioic acid as antiwear agent | |
| GB716978A (en) | Improvements in or relating to dialkyl monoaryl esters of ortho-phosphoric acid and methods of preparing the same | |
| GB823235A (en) | Preparation of a zinc dialkyl dithiophosphate product | |
| US2964477A (en) | Phosphate ester compositions | |
| US4116871A (en) | Preparation of phosphorus-containing acids and salts | |
| GB928702A (en) | Lubricant compositions and additives therefor | |
| GB743254A (en) | Lubricating oil compositions | |
| US2343213A (en) | Preparation of barium salts of dithiophosphoric acid esters | |
| US2948682A (en) | Formyl triesters of dithiophosphoric acid and lubricating oil compositions containing same | |
| US3047607A (en) | Boron containing phosphorus esters and process for preparation | |
| US2650935A (en) | Monoalkyl dinaphthyl phosphate esters | |
| US3284548A (en) | Process for making neutral hydroxy substituted triesters of phosphorodithioic acid | |
| GB955357A (en) | Organophosphorus-substituted dimethyl disulphides, and lubricant and fuel compositions containing the same | |
| US2476037A (en) | Wax-substituted diaryl dithiophosphoric acids and salts thereof |