US2264999A - Manufacture of lubricants - Google Patents
Manufacture of lubricants Download PDFInfo
- Publication number
- US2264999A US2264999A US284714A US28471439A US2264999A US 2264999 A US2264999 A US 2264999A US 284714 A US284714 A US 284714A US 28471439 A US28471439 A US 28471439A US 2264999 A US2264999 A US 2264999A
- Authority
- US
- United States
- Prior art keywords
- naphthenate
- lubricating
- lubricants
- oil
- manufacture
- 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
- 239000000314 lubricant Substances 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 9
- 230000001050 lubricating effect Effects 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 5
- 239000004312 hexamethylene tetramine Substances 0.000 description 5
- 229960004011 methenamine Drugs 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- -1 amine compound Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- XTYNGPJDSYLRIN-UHFFFAOYSA-N n-cyclohexylcyclohexanamine;octadecanoic acid Chemical compound C1CCCCC1[NH2+]C1CCCCC1.CCCCCCCCCCCCCCCCCC([O-])=O XTYNGPJDSYLRIN-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- ZUFLFMJCIRSDSD-UHFFFAOYSA-N diphenylazanium dodecanoate Chemical compound C(CCCCCCCCCCC)(=O)O.C1(=CC=CC=C1)NC1=CC=CC=C1 ZUFLFMJCIRSDSD-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- AMWHMJHLMLCUIF-UHFFFAOYSA-N octadecanoic acid N-phenylaniline Chemical compound N(c1ccccc1)c1ccccc1.CCCCCCCCCCCCCCCCCC(O)=O AMWHMJHLMLCUIF-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
-
- 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
- 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
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
- C10M2215/222—Triazines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
Definitions
- an oil as a desired base as, for instance a mineral oil the viscosity of which may be as desired, I incorporate therewith one or more compounds of detail more particularly referred to hereinafter.
- a petroleum stock-for example of viscosity of 4'7 to 200 Saybolt Universal at 210 F. may be employed, and with this incorporated a small amount of a ring-containing amine compound of a carboxylic acid which is of at least ten carbon atoms or a naphthenic acid.
- amines are dicyclohexylamine, diphonylamine, hexamethylene tetramine, and the acids are such acids as stearic, palmitic, lauric, naphthenic, etc.
- Such compounds are dicyclohexylamine stearate, dicyclohexylamine naphthenate, diphenylamine naphthenate, diphenylamine stearate, diphenylamine laurate, hexamethylene tete ramine naphthena'te, hexamethylene tetramine laurate. hexamethylene tetramine stearate, etc.
- These compounds are made by reacting the acid and base at moderate temperatures, as for instance 200 F., in a solvent or alone, and it is desirable to employ molecular proportions, variations therefrom resulting in corresponding dilution. The said compounds are applied in quite minor proportion in the composition with the oil,
- reaction products of the amines with these acids are soluble in mineral oil,.and being of generally rather high boiling points are capable of maintaining stable mixtures.
- a lubricant comprising a mineral oil with lubricating viscosity and a small amount of a salt of a ring-containing amine compound from the group consisting of di'cyclohexylamine, diphenylamine and hexamethylene tetramine and a carboxylic acid from the group consisting of fatty acids of at least ten carbon atoms and naphthenic acid.
- a lubricant comprising lubricating viscosity and a small amount of dicyclohexylamine stearate.
- a lubricant comprising a mineral oil with lubricating viscosity'and a small amount of diphenylamine naphthenate.
- a lubricant comprising a mineral oil with lubricating viscosity and a small amount of hexamethylene tetramine naphthenate.
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)
Description
Patented Dec. {2, 1941 zeta STATES PATET FEECE to The Standard Oil Company,
Cleveland,
Ohio, a corporation of Ohio No Drawing. Application July 15, 1939, Serial No. 284,714
4 Claims.
It has been proposed already to improve the resistance of mineral lubricating oils against deterioration, by adding certain amines. While in the main productive of advantageous results, a difiiculty arises in that under some circumstances of usage which is quite drastic, particularly by high temperature exposure, such products do not last as long as is desirable. I have found however that particularly durable lubricants may be prepared, capable of standing up under various drastic usage conditions, and being particularly effective in inhibiting ring-sticking or inhibiting stcklng of piston rings and accessory oil in internal combustion engines.
To the accomplishment of the foregoing and related ends, the invention, then comprises the features hereinafter fully described, and particularly pointed out in the claims, the following description setting forth in detail certain illustrative embodiments of the invention, these being indicative however, of but a few of the various ways in which the principle of the invention may be employed.
Taking an oil as a desired base, as, for instance a mineral oil the viscosity of which may be as desired, I incorporate therewith one or more compounds of detail more particularly referred to hereinafter. Thus, a petroleum stock-for example of viscosity of 4'7 to 200 Saybolt Universal at 210 F. may be employed, and with this incorporated a small amount of a ring-containing amine compound of a carboxylic acid which is of at least ten carbon atoms or a naphthenic acid. Illustrative of such amines are dicyclohexylamine, diphonylamine, hexamethylene tetramine, and the acids are such acids as stearic, palmitic, lauric, naphthenic, etc. Representative of such compounds are dicyclohexylamine stearate, dicyclohexylamine naphthenate, diphenylamine naphthenate, diphenylamine stearate, diphenylamine laurate, hexamethylene tete ramine naphthena'te, hexamethylene tetramine laurate. hexamethylene tetramine stearate, etc. These compounds are made by reacting the acid and base at moderate temperatures, as for instance 200 F., in a solvent or alone, and it is desirable to employ molecular proportions, variations therefrom resulting in corresponding dilution. The said compounds are applied in quite minor proportion in the composition with the oil,
in general it being unnecessary to exceed one per cent thereof in the total composition, and proportions as low as 0.01 per cent may be employed, depending somewhat upon the oil and the partic ular use in View. The reaction products of the amines with these acids are soluble in mineral oil,.and being of generally rather high boiling points are capable of maintaining stable mixtures.
As an example: With a Midcontinent lubricating stock having a viscosity of 300 Saybolt Universal at F., there is incorporated 0.25 per cent of dicycl'ohexylamine stearate.
As another example: With a similar lubricating stock there is incorporated 0.25 per cent of dicyclohexylamine naphthenate.
As another example: With a similar lubricating: stock there is incorporated 0.25 per cent of di-\ phenylamine naphthenate.
As another example: With a similar lubricating stock there is incorporated 0.25 per cent of hexametihylene tetramine naphthenate.
This application is a continuation, in part and to as to common subject matter, of my application Ser. No. 105,747, filed Oct. 15, 1936.
Other modes of applying the principle of the invention may be employed, change being made as regards the details described, provided the features stated in any of the following claims, or the equivalent of such, be employed.
I therefore particularly point out and distinctly claim as my invention:
1. A lubricant comprising a mineral oil with lubricating viscosity and a small amount of a salt of a ring-containing amine compound from the group consisting of di'cyclohexylamine, diphenylamine and hexamethylene tetramine and a carboxylic acid from the group consisting of fatty acids of at least ten carbon atoms and naphthenic acid.
2. A lubricant comprising lubricating viscosity and a small amount of dicyclohexylamine stearate.
3. A lubricant comprising a mineral oil with lubricating viscosity'and a small amount of diphenylamine naphthenate.
4. A lubricant comprising a mineral oil with lubricating viscosity and a small amount of hexamethylene tetramine naphthenate.
' JOHN M. MUSSELMAN.
a mineral oil with
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US284714A US2264999A (en) | 1939-07-15 | 1939-07-15 | Manufacture of lubricants |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US284714A US2264999A (en) | 1939-07-15 | 1939-07-15 | Manufacture of lubricants |
Publications (1)
Publication Number | Publication Date |
---|---|
US2264999A true US2264999A (en) | 1941-12-02 |
Family
ID=23091244
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US284714A Expired - Lifetime US2264999A (en) | 1939-07-15 | 1939-07-15 | Manufacture of lubricants |
Country Status (1)
Country | Link |
---|---|
US (1) | US2264999A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2622018A (en) * | 1949-10-19 | 1952-12-16 | Socony Vacuum Oil Co Inc | Motor fuel |
FR2547484A1 (en) * | 1983-06-20 | 1984-12-21 | Buckman Labor Inc | PROCESS FOR INHIBITING THE DEVELOPMENT AND PROLIFERATION OF MICROORGANISMS IN AQUEOUS MEDIA |
US4834892A (en) * | 1985-10-03 | 1989-05-30 | Elf France | Additives for lubricating oils, their process of preparation and lubricating compositions containing them |
-
1939
- 1939-07-15 US US284714A patent/US2264999A/en not_active Expired - Lifetime
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2622018A (en) * | 1949-10-19 | 1952-12-16 | Socony Vacuum Oil Co Inc | Motor fuel |
FR2547484A1 (en) * | 1983-06-20 | 1984-12-21 | Buckman Labor Inc | PROCESS FOR INHIBITING THE DEVELOPMENT AND PROLIFERATION OF MICROORGANISMS IN AQUEOUS MEDIA |
US4505831A (en) * | 1983-06-20 | 1985-03-19 | Buckman Laboratories, Inc. | Method of preservation of aqueous systems by addition to said systems of quaternary ammonium salts of hexamethylenetetramine |
US4834892A (en) * | 1985-10-03 | 1989-05-30 | Elf France | Additives for lubricating oils, their process of preparation and lubricating compositions containing them |
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