US2258591A - Lubricating oil composition - Google Patents

Lubricating oil composition Download PDF

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US2258591A
US2258591A US306330A US30633039A US2258591A US 2258591 A US2258591 A US 2258591A US 306330 A US306330 A US 306330A US 30633039 A US30633039 A US 30633039A US 2258591 A US2258591 A US 2258591A
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lubricating oil
salts
acids
oil composition
acid
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Moser Franz Rudolf
Dijksman Albert Johannes
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Shell Development Co
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Shell Development Co
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    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/54—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/50—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring 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
    • C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
    • C10M131/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
    • C10M131/12—Acids; Salts or esters 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic 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
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy 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
    • 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
    • C10M2207/146—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent 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
    • C10M2207/26—Overbased carboxylic acid salts
    • C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
    • 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
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated 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
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters 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
    • 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
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13
    • 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
    • C10N2010/08—Groups 4 or 14
    • 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
    • C10N2010/14—Group 7
    • 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
    • C10N2010/16—Groups 8, 9, or 10
    • 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

Definitions

  • the salts of the aromatic acids employed may i be those of mononuclear aromatic acids, such as benzoic acid, or polynuclear, such as naphthoic or anthracene carboxylic acid. These acids are all thermally very stable.
  • 'polyvalent' metal salts of the aromatic monocarboxylic acids and of these magnesium, calcium, strontium, barium, zinc, nickel, manganese, lead, copper, cobalt, and aluminum appear to be the most active.
  • the salts should be soluble in the lubricating oil.
  • alkyl radicals having preferably not more than six carbon atoms. Longer alkyl chains, though suitable from the point of view of enhancing solubility, tend to be thermally unstable. ing action of alkyl radicals are the following: Calcium naphthoate is practically insoluble in mineral lubricating oils, while the calcium salt of diamyl naphthoic acid is readily soluble.
  • Zinc benzoate dissolves in a furfural-reflned Venezuelan distillate to the extent of about .03%. Methyl benzoate of zinc dissolves to about 1%. The solubility of the zinc salt of para-tertiary butyl benzoic acid is about 1.5% and that of ditertiary butyl benzoic acid 2%.
  • the aromatic acids may also conta' polar substitution radicals, i. e. radicals containing elements other than C and H, such as hydroxy, alkoxy, aroxy, hydrosulfide, amino, imino, halogen, etc., radicals. While, in general, these polar radicals raise the solubility to a' lesser extent than alkyl radicals, and often depress, rather than enhance it, they frequently are. advantageous in further reducing corrosiveness. The effect .of' halogen on solubility is illustrated by para-chlorbenzoic acid or para-brombenzoic acid, the zinc salts of which are soluble to the extent of about .5%.
  • polar substitution radicals i. e. radicals containing elements other than C and H, such as hydroxy, alkoxy, aroxy, hydrosulfide, amino, imino, halogen, etc.
  • Very useful and comparatively easily prepared aromatic carboxylic acids are those prepared from alkyl phenols by the addition of CO2 (Kolbe reaction).
  • Alkyl phenols are obtainable by extraction of coal tar distillates or cracked petroleum distillates with aqueous alkali and acidification of the aqueous extract.
  • An example of a salt of an acid of this type is the zinc salt of thymotinic acid which is quite soluble even in V. I. lubricating oil and displays excellent anti-ring stickingproperties.
  • solubiliz- Although we prefer to use about .5 to 1.5% of the salts in our lubricating oil, suitable amounts may be varied from approximately 2% to 2.5%. Amounts in excess-of this limit tend to cause undue increase in viscosity as well as jelling of the oil.
  • Crankcase lubricating oils containing salts of monocarboxylic aromatic acids may also have 'present other compounding ingredients, such as oxidation inhibitors, pour-point depressors, blooming agents and extreme pressure agents, preferably those containing at least one of the elements phosphorus, sulfur or chlorine.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented- Oct. 14, 1941 UNITED STAT LUBRICATING on. coMrosi'rIoN Franz Rudolf Moser man, Amsterdam,
and Albert Johannes Dijks- Netherlands, assignors to Shell Development Company,
San Francisco,
Calif.,' a corporation of Delaware No. Drawing.
Application November 27, 1939,
Serial No. 306,330. In the Netherlands December 5, 1938 1' Claim. .(Cl; 2525-35) tion engines,- such as high speedDiesel engines,
aviation gasoline engines, etc., which due to their high power output, operate at relatively high temperatures, piston rings have a tendency to become stuck in the grooves. Lacquer and/or carbon formation appear to be the principal reasons for this occurrence. The addition of small amounts of certain oil-soluble carboxylic acid salts, such as polyvalent metal salts of fatty acids and n'aphthenic acids, is known to reduce the ring sticking tendencies. The addition of small amounts of the foregoing salts or soaps, however, has one or more of the following disadvantages: The newer type bearings containing cadmium .are corroded especially by the soaps of naphthenic and aliphatic acids. The soaps break down under the high temperatures obtained in lubricationand, thereupon, the oil loses its effectiveness. Certain of the above salts cause gelatinization in the lubricants, while others settle out of the lubricating oil during use.
Now, in accordance with our invention, we have found that polyvalent metal salts of aromatic monocarboxylic acids in which the carboxylic acid radical is directly attached to the ring and,
more particularly, the basic salts of these acids when added to mineral oils in suitable quantities produce effective anti-ring sticking lubricants which are'relatively free from the above disadvantages. I
The salts of the aromatic acids employed may i be those of mononuclear aromatic acids, such as benzoic acid, or polynuclear, such as naphthoic or anthracene carboxylic acid. These acids are all thermally very stable.
Especially valuable are 'polyvalent' metal salts of the aromatic monocarboxylic acids and of these magnesium, calcium, strontium, barium, zinc, nickel, manganese, lead, copper, cobalt, and aluminum appear to be the most active. To be, effective as ring sticking inhibitors the salts should be soluble in the lubricating oil.
While many of the salts of these simple aromatic carboxylic acids are little soluble in mineral oils, similar salts of the corresponding alkylated acids are usually much more soluble. Thus, preferred acids contains one or several alkyl radicals, having preferably not more than six carbon atoms. Longer alkyl chains, though suitable from the point of view of enhancing solubility, tend to be thermally unstable. ing action of alkyl radicals are the following: Calcium naphthoate is practically insoluble in mineral lubricating oils, while the calcium salt of diamyl naphthoic acid is readily soluble.
Zinc benzoate dissolves in a furfural-reflned Venezuelan distillate to the extent of about .03%. Methyl benzoate of zinc dissolves to about 1%. The solubility of the zinc salt of para-tertiary butyl benzoic acid is about 1.5% and that of ditertiary butyl benzoic acid 2%. A
If desired, the aromatic acids may also conta' polar substitution radicals, i. e. radicals containing elements other than C and H, such as hydroxy, alkoxy, aroxy, hydrosulfide, amino, imino, halogen, etc., radicals. While, in general, these polar radicals raise the solubility to a' lesser extent than alkyl radicals, and often depress, rather than enhance it, they frequently are. advantageous in further reducing corrosiveness. The effect .of' halogen on solubility is illustrated by para-chlorbenzoic acid or para-brombenzoic acid, the zinc salts of which are soluble to the extent of about .5%. Very useful and comparatively easily prepared aromatic carboxylic acids are those prepared from alkyl phenols by the addition of CO2 (Kolbe reaction). Alkyl phenols are obtainable by extraction of coal tar distillates or cracked petroleum distillates with aqueous alkali and acidification of the aqueous extract. An example of a salt of an acid of this type is the zinc salt of thymotinic acid which is quite soluble even in V. I. lubricating oil and displays excellent anti-ring stickingproperties.
, Further, as an aid to solubility, we have found that if the salts are added to the lubricating oil at an elevated temperature in the range of 250 C. to 350 0., the dissolution of the' salt in the oil is rendered much easier. Once they have been dissolved at elevated temperature, the solutions thus obtained tend to remain substantially stable also at normal temperature. The addition of high boiling oxygenated solvents, such as high boiling alcohols, esters, for example, butyl stearate, amyl rlcinoleate, etc., may be added further to improve solubility and stability of folutifins of the salts of this invention in lubricatng o s. v
Examples of the solubiliz- Although we prefer to use about .5 to 1.5% of the salts in our lubricating oil, suitable amounts may be varied from approximately 2% to 2.5%. Amounts in excess-of this limit tend to cause undue increase in viscosity as well as jelling of the oil.
Crankcase lubricating oils containing salts of monocarboxylic aromatic acids may also have 'present other compounding ingredients, such as oxidation inhibitors, pour-point depressors, blooming agents and extreme pressure agents, preferably those containing at least one of the elements phosphorus, sulfur or chlorine.
The following examples further illustrate our invention:
About .8% by weight of the zinc salt of paratertiary butyl'benzoic acid was dissolved in a furfural-refined Venezuelan lubricating oil distillate at about 280 C. The resulting lubricating oil composition was found to be suitable for internal lubrication of Diesel engines, materially retarding ring sticking and to have the advantage of being very little corrosive to bearing metals containing cadmium.
About 1%.by weight of the zinc salt of diiscpropyl salicyclic acid was dissolved in a highly refined mineral lubricating oil at a temperature of about 200 C. When using the lubricating oil composition thus prepared in Diesel engines or aviation gasoline engines, piston ring sticking did not occur, whilst corrosion of bearing metals
US306330A 1938-12-05 1939-11-27 Lubricating oil composition Expired - Lifetime US2258591A (en)

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DE (1) DE723649C (en)
FR (2) FR862110A (en)
GB (2) GB536827A (en)
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2477913A (en) * 1945-04-12 1949-08-02 Shell Dev Mineral lubricating oil
US2483859A (en) * 1945-07-31 1949-10-04 Shell Dev Antiring sticking lubricating composition
US2944970A (en) * 1954-07-12 1960-07-12 Shell Oil Co High temperature grease compositions containing salicylic acid derivatives
US2958662A (en) * 1955-09-26 1960-11-01 Shell Oil Co Detergent and wear inhibiting mineral oil compositions
US3656886A (en) * 1970-01-12 1972-04-18 Shell Oil Co Corrosion inhibitors
US10072359B2 (en) 2011-06-06 2018-09-11 Mitsubishi Chemical Corporation Oil agent for carbon fiber precursor acrylic fiber, oil composition for carbon fiber precursor acrylic fiber, processed-oil solution for carbon-fiber precursor acrylic fiber, and method for producing carbon-fiber precursor acrylic fiber bundle, and carbon-fiber bundle using carbon-fiber precursor acrylic fiber bundle

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2447234A (en) * 1942-03-31 1948-08-17 American Cyanamid Co Recovery of nicotinic acid from dilute solutions
US2436589A (en) * 1945-12-14 1948-02-24 Standard Oil Dev Co Compounded lubricated oil
US2744069A (en) * 1952-04-29 1956-05-01 Shell Dev Compounded lubricating compositions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2477913A (en) * 1945-04-12 1949-08-02 Shell Dev Mineral lubricating oil
US2483859A (en) * 1945-07-31 1949-10-04 Shell Dev Antiring sticking lubricating composition
US2944970A (en) * 1954-07-12 1960-07-12 Shell Oil Co High temperature grease compositions containing salicylic acid derivatives
US2958662A (en) * 1955-09-26 1960-11-01 Shell Oil Co Detergent and wear inhibiting mineral oil compositions
US3656886A (en) * 1970-01-12 1972-04-18 Shell Oil Co Corrosion inhibitors
US10072359B2 (en) 2011-06-06 2018-09-11 Mitsubishi Chemical Corporation Oil agent for carbon fiber precursor acrylic fiber, oil composition for carbon fiber precursor acrylic fiber, processed-oil solution for carbon-fiber precursor acrylic fiber, and method for producing carbon-fiber precursor acrylic fiber bundle, and carbon-fiber bundle using carbon-fiber precursor acrylic fiber bundle

Also Published As

Publication number Publication date
NL50248C (en) 1941-04-15
US2293419A (en) 1942-08-18
FR862110A (en) 1941-03-10
GB586461A (en) 1947-03-19
DE723649C (en) 1942-08-07
FR925799A (en) 1947-09-12
GB536827A (en) 1941-05-28

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