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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
• • 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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/102—Aliphatic fractions
• • 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
  • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
• • 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
  • C10M2207/08—Aldehydes; Ketones
• • 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
  • C10M2207/28—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
  • 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
  • C10M2207/40—Fatty vegetable or animal oils
• • 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
  • C10M2207/40—Fatty vegetable or animal oils
  • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
• • 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
  • C10N2010/02—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

Definitions

• This invention relates to an improved lubricating oil especially adapted for use in Diesel engines, dealing with mineral lubricating oils containing small quantities of a salt or salts of certain aromatic derivatives of higher fatty acids and metallic or amphoteric polyvalent elements.
• Diesel engines place an extremely heavy burden'on lubricating oils which are circulated through their internal lubricating systems during operation.
• piston rings develop a tendency to stick, possibly due to the accumulation of products of oxidation such as tar, coke, etc., or for other reasons. Stuck piston rings cause blow-by and result in loss of power, waste of fuel, rapid destruction of the lubricating oil and damage to the engine.
• compounds 40 which. are especially suited for inhibiting ring sticking and carbon deposition in Diesel engines comprise salts or salt-like compounds of polyvalent metallic and amphoteric elements, and more particularly the salts of light metals such as calcium, aluminum and especially magnesium of higher fatty acids, which acids have attached to their carbon chain an aromatic'grouping as a side branch through an aliphatic link of one 50 or more carbon atoms.
• Higher fatty acids as herein defined are those which are substantially stable under conditions 7 of lubrication, i. e., which do not polymerizeor oxidize excessively to form resins, and which 55 contain at least 10 carbon atoms, 12 to 22 carbons in straight chains being most desirable.
• the fatty acids may be saturated or mono-olefinic, and may contain substantially neutral substitution radicals'such as OH radicals. Suitable fatty acids are for instance lauric, palmitic, 5
• the aliphatic link which connects the aromatic grouping with the fatty acid carbon chain may be paraflinic or mono-olefinic andshould contain preferably not more than 3 carbon atoms. 10 It may advantageously, but not necessarily, be attached to the fatty acid carbon chain inclose proximity, such as an alphaposition, in regard to the carboxyl radical.
• the aromatic grouping comprises hydrocarbon 15 groups such as phenyl, naphthyl, tetra hydronaphthyl, anthracyl, etc., to which may be attached one or more alkyl, radicals preferably of not more than 3 carbons each.
• M is a polyvalent metallic or amphoteric" element, preferably a light weight metal having a specific gravity below about 4; and R. com.- prises an aliphatic carbon chain containing not more than one double bond and an aromatic hydrocarbon grouping attached thereto as a side branch through an aliphatic link of one or more carbon atoms, preferably in close proximity to the carboxyl radical.
• My compounds may be obtained by reacting a higher fatty acid with an aromatic aldehyde un- 36' der conditions to effect a condensation with simultancous liberation of water. "The general type of reaction involved may be illustrated as follows:
• a typical example of producing one of the acids of my invention is as follows:
• the double bond created by the condensation reaction may be reduced to yield a saturated bond.
• the benzalstearic acid of the above example was dried, dissolved in absolute ethyl alcohol and treated with 100 parts metallic sodium at l30-150 F. for three hours. After this, the benzalstearic acid was completely reduced to the equivalent benzyl compound.
• the amounts of the salts herein described, required successfully to inhibit or retard ring sticking are quite small and usually vary between .5 and 2.5% of the lubricating oil, although smaller or larger amounts may be added.
• ring sticking has been known to occur with a lubricating 011 containing a like amount of the calcium salt near 1000 hours of operation, and a heavier salt such as the barium salt, permitted occasional ring sticking after about 250 hours running of the engine. In the absence of any salt, ring sticking normally. occurred in less than hours under the standardized conditions of the tests.
• the salts of boron and beryllium are less stable and subject to hydrolysis .and for this reason are less desirable under conditions where hydrolysis may occur. Therefore the preferred group of compounds of this invention comprises the salts of the light metals, i. e., metals havingspecific gravities below about 4, and particularly the magnesium salts.
• salts of Zn, Cr, Mn, Cu, Co and Pb are quite effective, their inhibiting powers in general decreasing with increasing atomic numbers of the metals. In some instances mixtures of several salts containing different metals have given very good results. Salts of the remaining metals not enumerated above are of less interest, either because they can be dissolved in mineral lubricating oils with extreme difficulty only, or because their ring sticking inhibiting powers, although positive, are insufficient for most practical purposes.
• salts of my invention may be produced by the interaction of aromatic aldehydes with higher fatty acids or their salts, and the salts so produced may be added to the lubricating oils, ring sticking has also been inhibited successfully by dissolving in the lubricating oil small quantities, preferably in approximate equimolal proportions, of a suitable fatty acid salt and an aromatic aldehyde.
• Suitable aromatic aldehydes are, for instance,'
• benzaldehyde naphthaldehyde, anthracenealdehyde, tetrahydronaphthaldehyde, phenyl acetaldehyde, naphthacetaldehyde, phenyl propionic aldehyde, aldehydes in which the aromatic ring or rings contain alkyl radicals preferably of three or less carbon atoms such as toluyl aldehyde, xylyl aldehyde, prop-yl benzaldehyde, alkyl naphthaldehydes, etc.
• aldehydes I may employ chemically related substances, which upon oxidation are capable of yielding aldehydes; thus I may use the alcohols corresponding to the above aldehydes such as benzyl alcohols, naphthyl alcohols, etc., or esters of these alcohols, preferably with fatty acids, etc.
• I have used a lubricating oil, which normally caused piston rings to stick in less than 100 hours running, for over 1000 hours continuous running by adding thereto sufficient equimolal amounts of magnesium stearate, and benzyl alcohol or benzyl stearate to yield a theoretical quantity of 1.2% magnesium benzyl stearate.
• a lubricating oil containing 1.0% aluminum stearate and .7% benzyl stearate ran satisfactorily for over 1000 hours.
• lubricant which upon reaction under lubricating conditions matic hydrocarbon radical as a side branch through a link of one or more aliphatic carbon yield the salts, may be used in solution of any type of lubricant which is otherwise suitable for lubrication.
• lubricant which is otherwise suitable for lubrication.
• they may be blended with mineral lubricating oils prepared from parafllnic or non-paraiflnic crudes, shale oils, coal tar distillates, etc., by distillation, hydrogenation and/ or solvent extraction, or by polymerizing suitable olefines.
• suitable lubricating oils may be compounded with fatty oils, various oiliness or extreme pressure compounds, corrosion inhibitors, etc.
• a liquid lubricating oil composition com:
• a liquid lubricating oil composition comprising a mineral lubricating oil and a small amount of a salt of a polyvale t light metal and an aromatic higher fatty acid'having not more than one double bond in the aliphatic carbon chain to which the aromatic radical is linked as a side branch to the fatty acid chain through a link of one or more aliphatic carbon atoms said small amount being suiilcient toiinhibit ring sticking when the said composition is used in internal combustion engines.
• a liquid lubricating oil composition comprising a mineral lubricating oil and a small amount of a magnesium salt of a higher fatty acid having not more than one double bond in the carbon chain to which is attached an aromatic hydrocarbon radical as a side branch through a link consisting of one to three aliphatic carbon atoms
• the herein described salts, or compounds said small amount being suflicient to inhibit ring sticking'when the said composition is used in nternal combuston engines.
• a liquid lubricating oil composition vcomsticking when the said composition is usedin internal combustion engines.
• a liquid lubricating oil composition comprising a mineral lubricating oil and a small amount of aluminum alpha benzal stearate said small amount being sufiicient to inhibit ring stickingwhen the said composition is used in internal internal combustion engines ⁇ .
• a liquid lubricating oil forinternal combustion engines capable of retarding piston ring sticking comprising a mineral lubricating oil.
• a liquid lubricatingoil for internal comb sticking comprising a mineral lubricating -oil which contains from .5 to 2.5% of 'a salt of a polyvalent light metal and an aromatic higher tion engines capable of retarding piston ring I 9.
• a liquid 'lubri'catingo'il. composition comprising a mineral lubricating oil containing small:
• composition of claim .9 in which. the aldehyde and the fatty acid salt are contained in the oil in approximate equimolal proportions.
• composition of claim 9 in'which the element is magnesium.
• a liquid lubricating oil composition com prising a mineral lubricating oil and a. small amount of a'salt combining an element selectedfrom the group consisting of polyvalent metallicand amphoteric elements with an aromatic fatty acid produced by condensing a higher fatty acid having not more than one double bond in the aliphatic carbon chain and an aromatic aide-- hyde, said small amount being sufllcient to inhibit ring sticking when said composition isused inan internal combustionengine.

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• 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)

Priority Applications (3)

Applications Claiming Priority (1)

Publications (1)

Family

ID=22595116

Family Applications (1)

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Cited By (4)

Families Citing this family (1)

• 1937
  • 1937-09-18 US US164576A patent/US2186346A/en not_active Expired - Lifetime
• 1938
  • 1938-04-16 FR FR836720D patent/FR836720A/fr not_active Expired
  • 1938-09-09 GB GB26413/38A patent/GB509097A/en not_active Expired

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