US3367869A - Alkaline lubricating oil - Google Patents
Alkaline lubricating oil Download PDFInfo
- Publication number
- US3367869A US3367869A US554700A US55470066A US3367869A US 3367869 A US3367869 A US 3367869A US 554700 A US554700 A US 554700A US 55470066 A US55470066 A US 55470066A US 3367869 A US3367869 A US 3367869A
- Authority
- US
- United States
- Prior art keywords
- compound
- lubricating oil
- composition
- carbon atoms
- water
- 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 - Lifetime
Links
- 239000010687 lubricating oil Substances 0.000 title claims description 9
- 239000000203 mixture Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
- 239000011787 zinc oxide Substances 0.000 claims description 7
- 230000001050 lubricating effect Effects 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000002199 base oil Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910007541 Zn O Inorganic materials 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 150000003752 zinc compounds Chemical class 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000010763 heavy fuel oil Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- -1 2-ethyl Chemical group 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000010724 circulating oil Substances 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 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
- 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
-
- 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
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
-
- 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
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
-
- 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
-
- 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
-
- 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
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
-
- 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
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
-
- 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
- C10M2207/16—Naphthenic 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/24—Epoxidised acids; Ester derivatives thereof
-
- 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
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
-
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/015—Dispersions of solid lubricants
- C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
Definitions
- the cleansing operation comprises a water-Wash which has the effect of coagulating insoluble materials (e.g., carbon) which are then more easily removed by subsequent centrifuging. It is customary to rely on this washing operation to reduce mineral acidity in the oil but this is not always very satisfactory.
- crankcase oil In most large marine diesel engines the crankcase oil is also used for piston cooling where it may be subjected to piston temperatures in the region of 180 to 200 C. On many ships the same oil is also used for the total lubrication of auxiliary trunk-piston medium speed diesel engines. For both these applications an improvement in oxidation stability would be an advantage.
- a lubricating composition comprising a lubricating base oil, which may be mineral or synthetic, having blended therein from 0.01 to 20% wt., preferably 0.l-5% wt., of the composition, of a compound having the empirical formula (RCOO) Zn O where R is an alkyl, cycloalkyl, aryl, aralkyl or alkaryl group preferably having not more than 24 carbon atoms, the compound having a tetrahedral structure with the four zinc atoms at the corners, the oxygen atom in the centre and the six carboxylate groups arranged along the sides. Most suitably R is an alkyl group having up to 18 carbon atoms.
- Compounds of this type may be prepared, according to another aspect of the invention, by reacting one molar proportion of zinc oxide with one and a half molar proportions of an acid of the formula RCOOH, where R is as specified above, and removing all of the water formed during the reaction.
- the reaction is preferably carried out by refluxing with an azeotroping agent such as benzene or toluene. Excess zinc oxide may be used in the reaction but if the water formed is removed this excess does not react and it has to be filtered off from the product.
- the reaction may be represented as follows:
- the base oil used in the compositions according to the invention is usually a refined lubricating oil obtained from petroleum, e.g., one having a viscosity in the range 3-50 centistokes at 210 F. and a viscosity index in the range -110.
- the amount of the additive should preferably be such as to give the composition a total base number of 0.05- 100, preferably 0.5100, mg. KOH/ g.
- the lubricating composition may contain more than one of the zinc compounds and that more than one carboxylic acid may be used in the preparation of the compounds with the result that a given molecule of the product may contain more than one type of carboxylic group.
- the number of carbon atoms present in the carboxylic acids employed in the reaction ranges from 4 carbon atoms, as represented by crotonic acid, up to 18 carbon atoms, as represented by oleic acid.
- TBN of all the compounds prepared according to the invention was found to be very close to the theoretical value calculated from the empirical formula given above.
- a number of lubricating compositions according to the invention Were prepared using Compounds A and B in refined petroleum base oils.
- the compositions are shown in Table 2 which gives percentages by Weight of the ingredients and also the 210 F. viscosity (centistokes) and viscosity index of the base oils.
- Composition P had a total base number (TBN) of 2.0 mg. KOH/ g. It did not form stable emulsions with Water and after two washings with 20% distilled water at 60 C. its TBN was 1.7 mg. KOH/ g. which is considered to be very satisfactory.
- Composition R had a TBN of 1.38. It was given a much more severe water wash using ten times its volume of distilled water at 70 C. After one Wash the TBN was 1.14 and after two washes it was 0.96, i.e., 83% and 70% respectively of the original TBN.
- a commercially available water-Washable oil for marine engines gave figures of 44% and 13% when subjected to the same test.
- a lubricating base oil comprising a major amount of a lubricating base oil and from 0.01 to 20% by weight of the composition of a compound having the empirical formula (RCOO) Zn O, where R is selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl and alkaryl groups having up to 24 carbon atoms, the compound having a tetrahedral structure with the four zinc atoms at the corners, the oxygen atom in the center and the six carboxylate groups arranged along the sides.
- R is selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl and alkaryl groups having up to 24 carbon atoms, the compound having a tetrahedral structure with the four zinc atoms at the corners, the oxygen atom in the center and the six carboxylate groups arranged along the sides.
- composition according to claim 1 in which the proportion of the said compound in the composition is from 0.1 to 5% wt.
- composition according to claim 1 in which the proportion of the said compound in the composition is" such that the composition has a total base number of from 0.05 to mg. KOH/g.
- composition according to claim 1 in which the proportion of the said compound in the composition is such that the composition has a total base number of from 0.5 to 100 mg. KOH/g.
- R is an alkyl group having 4 to 18 carbon atoms.
- a method of preparing a compound suitable for use as a lubricating oil additive and having the empirical formula (RCOO) Zn O, wherein R is selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl and alkaryl groups having up to 24 carbon atoms which comprises reacting one molar proportion of zinc oxide with one and a half molar proportions of an acid of the formula RCOOH, refluxing the reactants with an azeotroping agent, and removing all of the water formed during the reaction.
- R is an alkyl group having 4 to 18 carbon atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Woven Fabrics (AREA)
- Belt Conveyors (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25847/65A GB1142195A (en) | 1965-06-18 | 1965-06-18 | Alkaline lubricating oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3367869A true US3367869A (en) | 1968-02-06 |
Family
ID=10234313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US554700A Expired - Lifetime US3367869A (en) | 1965-06-18 | 1966-06-02 | Alkaline lubricating oil |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3367869A (enrdf_load_stackoverflow) |
| AT (1) | AT270033B (enrdf_load_stackoverflow) |
| BE (1) | BE682705A (enrdf_load_stackoverflow) |
| CH (1) | CH481209A (enrdf_load_stackoverflow) |
| DE (1) | DE1594355A1 (enrdf_load_stackoverflow) |
| ES (1) | ES328225A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1142195A (enrdf_load_stackoverflow) |
| NL (1) | NL6608326A (enrdf_load_stackoverflow) |
| NO (1) | NO120154B (enrdf_load_stackoverflow) |
| SE (1) | SE339967B (enrdf_load_stackoverflow) |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3539513A (en) * | 1967-05-16 | 1970-11-10 | Britannic Petroleum Co Ltd The | Lubricant additive |
| US3544609A (en) * | 1966-11-10 | 1970-12-01 | British Petroleum Co | Zinc complexes |
| US4407818A (en) * | 1980-12-17 | 1983-10-04 | Bio-Systems Research, Inc. | Anti viral, anti bacterial and/or anti fungal composition containing metal oxyalkylate |
| US4497663A (en) * | 1979-06-26 | 1985-02-05 | The British Petroleum Company Limited | Method of encapsulating a polluting liquid |
| US4812242A (en) * | 1984-05-31 | 1989-03-14 | The British Petroleum Company P.L.C. | Method of encapsulating organic material |
| US5110488A (en) * | 1986-11-24 | 1992-05-05 | The Lubrizol Corporation | Lubricating compositions containing reduced levels of phosphorus |
| US5274144A (en) * | 1990-06-15 | 1993-12-28 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of metal soaps |
| US20080132432A1 (en) * | 2006-12-01 | 2008-06-05 | Mathur Naresh C | Additives and lubricant formulations for providing friction modification |
| WO2010096325A1 (en) | 2009-02-18 | 2010-08-26 | The Lubrizol Corporation | Amine derivatives as friction modifiers in lubricants |
| WO2012154708A1 (en) | 2011-05-12 | 2012-11-15 | The Lubrizol Corporation | Aromatic imides and esters as lubricant additives |
| WO2013013026A1 (en) | 2011-07-21 | 2013-01-24 | The Lubrizol Corporation | Carboxylic pyrrolidinones and methods of use thereof |
| WO2015200592A1 (en) | 2014-06-27 | 2015-12-30 | The Lubrizol Corporation | Mixtures of friction modifiers to provide good friction performance to transmission fluids |
| US9353026B2 (en) | 2013-07-19 | 2016-05-31 | Baker Hughes Incorporated | Oil soluble hydrogen sulfide scavenger |
| WO2016144639A1 (en) | 2015-03-10 | 2016-09-15 | The Lubrizol Corporation | Lubricating compositions comprising an anti-wear/friction modifying agent |
| WO2016164345A1 (en) | 2015-04-09 | 2016-10-13 | The Lubrizol Corporation | Lubricants containing quaternary ammonium compounds |
| US9480946B2 (en) | 2013-04-15 | 2016-11-01 | Baker Hughes Incorporated | Metal carboxylate salts as H2S scavengers in mixed production or dry gas or wet gas systems |
| WO2017205270A1 (en) | 2016-05-24 | 2017-11-30 | The Lubrizol Corporation | Seal swell agents for lubricating compositions |
| WO2017205271A1 (en) | 2016-05-24 | 2017-11-30 | The Lubrizol Corporation | Seal swell agents for lubricating compositions |
| WO2017205274A1 (en) | 2016-05-24 | 2017-11-30 | The Lubrizol Corporation | Seal swell agents for lubricating compositions |
| WO2018057675A1 (en) | 2016-09-21 | 2018-03-29 | The Lubrizol Corporation | Polyacrylate antifoam components with improved thermal stability |
| WO2018057678A1 (en) | 2016-09-21 | 2018-03-29 | The Lubrizol Corporation | Fluorinated polyacrylate antifoam components for lubricating compositions |
| WO2018112135A1 (en) | 2016-12-16 | 2018-06-21 | The Lubrizol Corporation | Lubrication of an automatic transmission with reduced wear on a needle bearing |
| WO2018118163A1 (en) | 2016-12-22 | 2018-06-28 | The Lubrizol Corporation | Fluorinated polyacrylate antifoam components for lubricating compositions |
| WO2019183365A1 (en) | 2018-03-21 | 2019-09-26 | The Lubrizol Corporation | NOVEL FLUORINATED POLYACRYLATES ANTIFOAMS IN ULTRA-LOW VISCOSITY (<5 CST) finished fluids |
| WO2023196116A1 (en) | 2022-04-06 | 2023-10-12 | The Lubrizol Corporation | Method to minimize conductive deposits |
| WO2025136852A1 (en) | 2023-12-22 | 2025-06-26 | The Lubrizol Corporation | Synergistic polyacrylate antifoam systems for use in industrial gear lubricants |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3831883C1 (enrdf_load_stackoverflow) * | 1988-09-20 | 1989-09-21 | Schill & Seilacher (Gmbh & Co), 2000 Hamburg, De | |
| GB9524642D0 (en) | 1995-12-01 | 1996-01-31 | Ethyl Petroleum Additives Ltd | Hydraulic fluids |
| DE19904139A1 (de) | 1999-02-03 | 2000-08-10 | Cognis Deutschland Gmbh | Verfahren zur Herstellung überbasischer Zinkseifen |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1767076A (en) * | 1927-02-07 | 1930-06-24 | Lindsay Mcmillan Company | Lubricant and method of producing the same |
| US2362233A (en) * | 1942-12-29 | 1944-11-07 | Standard Oil Dev Co | Lubricants |
| US2384551A (en) * | 1944-03-24 | 1945-09-11 | Carbide & Carbon Chem Corp | Lubricant |
| US2501127A (en) * | 1945-11-29 | 1950-03-21 | Nat Lead Co | Basic zinc salicylate |
| US3017361A (en) * | 1956-09-05 | 1962-01-16 | Texaco Inc | Non-squawking automatic transmission fluid |
| GB891858A (en) * | 1958-07-17 | 1962-03-21 | Ghent Sa | Improvements in or relating to oil-soluble soaps of polyvalent metals |
-
1965
- 1965-06-18 GB GB25847/65A patent/GB1142195A/en not_active Expired
-
1966
- 1966-06-02 US US554700A patent/US3367869A/en not_active Expired - Lifetime
- 1966-06-10 ES ES0328225A patent/ES328225A1/es not_active Expired
- 1966-06-14 NO NO163442A patent/NO120154B/no unknown
- 1966-06-15 NL NL6608326A patent/NL6608326A/xx unknown
- 1966-06-17 SE SE08291/66A patent/SE339967B/xx unknown
- 1966-06-17 BE BE682705A patent/BE682705A/xx unknown
- 1966-06-17 CH CH879366A patent/CH481209A/de not_active IP Right Cessation
- 1966-06-17 AT AT580666A patent/AT270033B/de active
- 1966-06-18 DE DE1966B0087601 patent/DE1594355A1/de active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1767076A (en) * | 1927-02-07 | 1930-06-24 | Lindsay Mcmillan Company | Lubricant and method of producing the same |
| US2362233A (en) * | 1942-12-29 | 1944-11-07 | Standard Oil Dev Co | Lubricants |
| US2384551A (en) * | 1944-03-24 | 1945-09-11 | Carbide & Carbon Chem Corp | Lubricant |
| US2501127A (en) * | 1945-11-29 | 1950-03-21 | Nat Lead Co | Basic zinc salicylate |
| US3017361A (en) * | 1956-09-05 | 1962-01-16 | Texaco Inc | Non-squawking automatic transmission fluid |
| GB891858A (en) * | 1958-07-17 | 1962-03-21 | Ghent Sa | Improvements in or relating to oil-soluble soaps of polyvalent metals |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3544609A (en) * | 1966-11-10 | 1970-12-01 | British Petroleum Co | Zinc complexes |
| US3539513A (en) * | 1967-05-16 | 1970-11-10 | Britannic Petroleum Co Ltd The | Lubricant additive |
| US4497663A (en) * | 1979-06-26 | 1985-02-05 | The British Petroleum Company Limited | Method of encapsulating a polluting liquid |
| US4407818A (en) * | 1980-12-17 | 1983-10-04 | Bio-Systems Research, Inc. | Anti viral, anti bacterial and/or anti fungal composition containing metal oxyalkylate |
| US4812242A (en) * | 1984-05-31 | 1989-03-14 | The British Petroleum Company P.L.C. | Method of encapsulating organic material |
| US5110488A (en) * | 1986-11-24 | 1992-05-05 | The Lubrizol Corporation | Lubricating compositions containing reduced levels of phosphorus |
| US5274144A (en) * | 1990-06-15 | 1993-12-28 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of metal soaps |
| US20080132432A1 (en) * | 2006-12-01 | 2008-06-05 | Mathur Naresh C | Additives and lubricant formulations for providing friction modification |
| WO2010096325A1 (en) | 2009-02-18 | 2010-08-26 | The Lubrizol Corporation | Amine derivatives as friction modifiers in lubricants |
| WO2012154708A1 (en) | 2011-05-12 | 2012-11-15 | The Lubrizol Corporation | Aromatic imides and esters as lubricant additives |
| WO2013013026A1 (en) | 2011-07-21 | 2013-01-24 | The Lubrizol Corporation | Carboxylic pyrrolidinones and methods of use thereof |
| US9480946B2 (en) | 2013-04-15 | 2016-11-01 | Baker Hughes Incorporated | Metal carboxylate salts as H2S scavengers in mixed production or dry gas or wet gas systems |
| US9353026B2 (en) | 2013-07-19 | 2016-05-31 | Baker Hughes Incorporated | Oil soluble hydrogen sulfide scavenger |
| WO2015200592A1 (en) | 2014-06-27 | 2015-12-30 | The Lubrizol Corporation | Mixtures of friction modifiers to provide good friction performance to transmission fluids |
| WO2016144639A1 (en) | 2015-03-10 | 2016-09-15 | The Lubrizol Corporation | Lubricating compositions comprising an anti-wear/friction modifying agent |
| WO2016164345A1 (en) | 2015-04-09 | 2016-10-13 | The Lubrizol Corporation | Lubricants containing quaternary ammonium compounds |
| WO2017205270A1 (en) | 2016-05-24 | 2017-11-30 | The Lubrizol Corporation | Seal swell agents for lubricating compositions |
| WO2017205271A1 (en) | 2016-05-24 | 2017-11-30 | The Lubrizol Corporation | Seal swell agents for lubricating compositions |
| WO2017205274A1 (en) | 2016-05-24 | 2017-11-30 | The Lubrizol Corporation | Seal swell agents for lubricating compositions |
| WO2018057675A1 (en) | 2016-09-21 | 2018-03-29 | The Lubrizol Corporation | Polyacrylate antifoam components with improved thermal stability |
| WO2018057678A1 (en) | 2016-09-21 | 2018-03-29 | The Lubrizol Corporation | Fluorinated polyacrylate antifoam components for lubricating compositions |
| WO2018112135A1 (en) | 2016-12-16 | 2018-06-21 | The Lubrizol Corporation | Lubrication of an automatic transmission with reduced wear on a needle bearing |
| WO2018118163A1 (en) | 2016-12-22 | 2018-06-28 | The Lubrizol Corporation | Fluorinated polyacrylate antifoam components for lubricating compositions |
| WO2019183365A1 (en) | 2018-03-21 | 2019-09-26 | The Lubrizol Corporation | NOVEL FLUORINATED POLYACRYLATES ANTIFOAMS IN ULTRA-LOW VISCOSITY (<5 CST) finished fluids |
| WO2023196116A1 (en) | 2022-04-06 | 2023-10-12 | The Lubrizol Corporation | Method to minimize conductive deposits |
| WO2025136852A1 (en) | 2023-12-22 | 2025-06-26 | The Lubrizol Corporation | Synergistic polyacrylate antifoam systems for use in industrial gear lubricants |
Also Published As
| Publication number | Publication date |
|---|---|
| CH481209A (de) | 1969-11-15 |
| BE682705A (enrdf_load_stackoverflow) | 1966-12-19 |
| AT270033B (de) | 1969-04-10 |
| ES328225A1 (es) | 1967-04-01 |
| NO120154B (enrdf_load_stackoverflow) | 1970-09-07 |
| GB1142195A (en) | 1969-02-05 |
| NL6608326A (enrdf_load_stackoverflow) | 1966-12-19 |
| SE339967B (enrdf_load_stackoverflow) | 1971-11-01 |
| DE1594355A1 (de) | 1969-08-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3367869A (en) | Alkaline lubricating oil | |
| US3036971A (en) | Lubricating oils containing carbonated basic sulfurized calcium phenates | |
| US2805203A (en) | Addition agent for oil compositions and the like | |
| US2360302A (en) | Compounded hydrocarbon oil | |
| US2406564A (en) | Compounded lubricating oil | |
| US2680094A (en) | Rust preventive oil composition | |
| US2432095A (en) | Lubricating composition | |
| US2628942A (en) | Lubricating oils containing metal derivatives of cyclic imides | |
| US3844964A (en) | Extreme pressure lubricating oil additive | |
| US2409726A (en) | Lubricant composition | |
| US3182020A (en) | Stabilized calcium acetate oil dispersions | |
| JP2598489B2 (ja) | 過塩基マグネシウムスルホン酸塩組成物 | |
| US2905639A (en) | Lubricating oil compositions | |
| US3235494A (en) | Two-cycle engine lubricating composition | |
| US3340191A (en) | Fuel and lubricant compositions | |
| US2952636A (en) | Associates of inorganic metal compounds with copolymers containing a plurality of hydroxy groups | |
| US2956870A (en) | Process for suppressing deposit formation in an internal combustion engine | |
| US2790766A (en) | Complex metal salts of phosphoric acid esters and mineral oil compositions containing the same | |
| US3320163A (en) | Phenolic corrosion inhibitors | |
| US2480664A (en) | Lubricating oil composition | |
| US2879230A (en) | Motor lubricating oil composition | |
| US2944022A (en) | Marine diesel lubricant | |
| US2226543A (en) | Lubricating oil | |
| US2512784A (en) | Lubricant | |
| US3164580A (en) | Phosphosulfurized esters of amino acids |