US2205172A - Preparation of lubricants - Google Patents
Preparation of lubricants Download PDFInfo
- Publication number
- US2205172A US2205172A US176664A US17666437A US2205172A US 2205172 A US2205172 A US 2205172A US 176664 A US176664 A US 176664A US 17666437 A US17666437 A US 17666437A US 2205172 A US2205172 A US 2205172A
- Authority
- US
- United States
- Prior art keywords
- aminophenol
- benzyl
- butyl
- oil
- lubricant
- 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
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
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
Definitions
- a mineral oil is employed as a base, and with it in composition a small amount of a salt of an N-substituted p-aminophenol (as for instance p-butyl aminophenol, p-benzyl aminophenol, and the like) with an organic carboxylic acid of at least six carbon atoms, (such acid being for instance a fatty acid of at least six carbon atoms, a naphthenic acid, or a halo-carboxylic acid, fatty acid or naphthenic) as p-butyl aminophenol stearate, p-butyl aminophenol laurate, p-butyl aminophenol palmitate, p-butyl aminophenol oleate, p-benzyl aminophenol laurate, p-benzyl amino
- the compounds such as pointed out above may be prepared in suitable manner, as for instance by heating together equimolar quantities of the N-substituted p-aminophenol and the acids to be employed, in a suitable solvent, as for instance isopropyl alcohol about ten parts. Heating in a Ill) steam bath for about 5 minutes or slightly more, is in general suflicient for the reaction. The isopropyl alcohol or other solvent is then removed by evaporation, and the formed compound is ready for incorporation with the petroleum.
- a suitable solvent as for instance isopropyl alcohol about ten parts. Heating in a Ill) steam bath for about 5 minutes or slightly more, is in general suflicient for the reaction.
- the isopropyl alcohol or other solvent is then removed by evaporation, and the formed compound is ready for incorporation with the petroleum.
- a Mid-Continent S. A. E. 30 oil is compounded with 0.1 per cent of monobenzyl p-aminophenol dichlorostearate.
- This product when operated as an internal combustion engine lubricant, under severe engine operating conditions, viz. head temperature 500 F., and jacket temperature 212 F., after fifty hours of continuous operation showed only 0.30 per cent sludge operation, whereas the oil with mono-benzyl p-aminophenol per se showed 0.40 per cent sludge, and the oil with dichlorostearic acid per se showed 4.00 per cent sludge.
- rings in the engine stuck while in the lubricant with the 'mono-benzyl p-aminophenol dichlorostearate no piston rings stuck, but the engine continued to be highly satisfactorily lubricated.
- a lubricant comprising a mineral lubricating oil and a small amount of a salt of an N-substituted p-aminophenol and an organic carboxylic acid of at least six carbon atoms.
- a lubricant comprising a mineral lubricating oil and a small amount of a salt of an N-substituted p-aminophenol and a fatty acid of at least six carbon atoms.
- a lubricant comprising a mineral lubricating oil and a small amount of a salt of an N-substituted p-aminophenol and naphthenic acid.
- Alubricant comprising a mineral lubricating oil and a small amount of a salt of an N-substituted p-aminophenol and an organic halo-carboxylic acid of at least six 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)
Description
Patented June 18, 1940 UNITED STATES PREPARATION OF LUBRICANTS John M. Musselman and Herman P. Lankelma, Cleveland, Ohio, assignors to The Standard Oil Company, Cleveland,
Ohio
Ohio, a corporation of No Drawing. Application November 26, 1937, Serial No. 176,664
4 Claims.
We have found that if a lubricant be made up with certain compounds, the result is a remarkably durable product, which is all the more surprising inasmuch as the constituents do not indicate such result-possibility. A mineral oil is employed as a base, and with it in composition a small amount of a salt of an N-substituted p-aminophenol (as for instance p-butyl aminophenol, p-benzyl aminophenol, and the like) with an organic carboxylic acid of at least six carbon atoms, (such acid being for instance a fatty acid of at least six carbon atoms, a naphthenic acid, or a halo-carboxylic acid, fatty acid or naphthenic) as p-butyl aminophenol stearate, p-butyl aminophenol laurate, p-butyl aminophenol palmitate, p-butyl aminophenol oleate, p-benzyl aminophenol laurate, p-benzyl aminophenol stearate, p-benzyl aminophenol palmitate, p-benzyl aminophenol oleate, p-butyl aminophenol naphthenate, p-benzyl aminophenol naphthenate, p-butyl aminophenol chlorostearate, p-butyl aminophenol dichlorostearate, p-benzyl aminophenol dichlorostearate, p-benzyl aminophenol chlorostearate, p-benzyl aminophenol chloronaphthenate, p-butyl aminophenol chloronaphthenate, etc. The amount of the salt employed need not generally exceed one per cent, based on the oil, and may usually be one-tenth to one per cent.
The compounds such as pointed out above may be prepared in suitable manner, as for instance by heating together equimolar quantities of the N-substituted p-aminophenol and the acids to be employed, in a suitable solvent, as for instance isopropyl alcohol about ten parts. Heating in a Ill) steam bath for about 5 minutes or slightly more, is in general suflicient for the reaction. The isopropyl alcohol or other solvent is then removed by evaporation, and the formed compound is ready for incorporation with the petroleum.
As an example: A Mid-Continent S. A. E. 30 oil is compounded with 0.1 per cent of monobenzyl p-aminophenol dichlorostearate. This product when operated as an internal combustion engine lubricant, under severe engine operating conditions, viz. head temperature 500 F., and jacket temperature 212 F., after fifty hours of continuous operation showed only 0.30 per cent sludge operation, whereas the oil with mono-benzyl p-aminophenol per se showed 0.40 per cent sludge, and the oil with dichlorostearic acid per se showed 4.00 per cent sludge. Furthermore, in the last two instances rings in the engine stuck, while in the lubricant with the 'mono-benzyl p-aminophenol dichlorostearate no piston rings stuck, but the engine continued to be highly satisfactorily lubricated.
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.
We therefore particularly point out and dis-- tinctly claim as our invention:
l. A lubricant comprising a mineral lubricating oil and a small amount of a salt of an N-substituted p-aminophenol and an organic carboxylic acid of at least six carbon atoms.
2. A lubricant comprising a mineral lubricating oil and a small amount of a salt of an N-substituted p-aminophenol and a fatty acid of at least six carbon atoms.
3. A lubricant comprising a mineral lubricating oil and a small amount of a salt of an N-substituted p-aminophenol and naphthenic acid.
4. Alubricant comprising a mineral lubricating oil and a small amount of a salt of an N-substituted p-aminophenol and an organic halo-carboxylic acid of at least six carbon atoms.
JOHN M. MUSSELMAN. HERMAN P. LANKELMA.
CERTIFICATE OF CORRECTION.
Patent No. 2,20 ,172. June 1 191p.
JOHN M. MUSSEIMAN, ET AL.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Second column, line 111., for the word "operation" read -fomation; and that the said Letters Patent shou ld be read with this correction therein that the same may conform to the record of the case in the Patent Office.
Signed and sealed this 25rd day of July, A. D. 19140.
Henry Van Arsdale,
(Seal) Acting Commissioner of Patents.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US176664A US2205172A (en) | 1937-11-26 | 1937-11-26 | Preparation of lubricants |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US176664A US2205172A (en) | 1937-11-26 | 1937-11-26 | Preparation of lubricants |
Publications (1)
Publication Number | Publication Date |
---|---|
US2205172A true US2205172A (en) | 1940-06-18 |
Family
ID=22645317
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US176664A Expired - Lifetime US2205172A (en) | 1937-11-26 | 1937-11-26 | Preparation of lubricants |
Country Status (1)
Country | Link |
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US (1) | US2205172A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3476686A (en) * | 1968-06-04 | 1969-11-04 | Sinclair Research Inc | Ashless lubricating oil detergents |
US9936706B2 (en) | 2013-06-27 | 2018-04-10 | Middleby Marshall Holding Llc | Forced moisture evacuation for rapid baking |
-
1937
- 1937-11-26 US US176664A patent/US2205172A/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3476686A (en) * | 1968-06-04 | 1969-11-04 | Sinclair Research Inc | Ashless lubricating oil detergents |
US9936706B2 (en) | 2013-06-27 | 2018-04-10 | Middleby Marshall Holding Llc | Forced moisture evacuation for rapid baking |
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