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
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
  • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
  • C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
  • C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/188—Carboxylic acids; metal salts thereof
  • C10L1/189—Carboxylic acids; metal salts thereof having at least one carboxyl group bound to an aromatic carbon atom
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/188—Carboxylic acids; metal salts thereof
  • C10L1/189—Carboxylic acids; metal salts thereof having at least one carboxyl group bound to an aromatic carbon atom
  • C10L1/1895—Carboxylic acids; metal salts thereof having at least one carboxyl group bound to an aromatic carbon atom polycarboxylic acid
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
  • C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
  • C10L1/2418—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides containing a carboxylic substituted; derivatives thereof, e.g. 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
  • C10M2207/10—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
  • C10M2207/142—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
  • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
• • 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
  • C10N2050/10—Semi-solids; greasy

Definitions

• Additives of the first group usually contain metal atoms and they are quickly depleted and therefore must be applied in rather high concentrations. Particularly when these additives are incorporated in lubricant oils that are used as motor oils in internal combustion engines. The high concentration and metal content are disadvantageous because they form ash. Additives of the second group, which are less readily depleted, can
• each R may be hydrogen or a hydrocarbyl group having less than 24 carbon atoms.
• These acids have good solubility in hydrocarbon oils, are excellent rust inhibitors and show only a slight copper-lead corrosion.
• the liquid hydrocarbons,'such as fuels or lubricating oil compositions, contain a minor proportion of one or more of the aromatic dicarboxylic acids of the above formula.
• the present compounds maybe utilized as anti-rust additives for mineral and synthetic lubricating oils which are employed as motor oils in internal combustion engines. Mineral oils that are generally paraffinic and/or naphthenic are preferred, although they may. contain substantial proportions of aromatic hydrocarbons, a single neutral base or a mixture or blend of base stocks or a bright stock may be used as the base stock.
• any suitable high-viscosity index or middle viscosity index base stock or mixtures thereof can be used.
• a suitable viscosity index (VI) improver oils of somewhat lower VI as for example 65 or less may also be used.
• the compounds according to the invention may also be utilized as anti-rust additives in distillate or residual hydrocarbon fuels and have been found especially effective when used in gasolines.
• the additives of this invention are useful in leaded or unleaded gasoline compositions.
• X is preferably a hydroxyl group.
• suitable additives are 2- hydroxybenzene-l,3-dicarboxylic acids in which both of the R, substituents are hydrogen atoms.
• R is preferably an aliphatic hydrocarbon group having more than 12 carbon atoms.
• a preferred additive is 2-hydroxy-5-cetyl-benzene-l,3-dicarboxylic acid, 2-hydroxyl-5-lauryl-benzenel -3-dicarboxylic acid, 2-hydroxy-5-stearyl-benzene, l-3-dicarboxylic acid, 2-hydroxy-5-cetyl-benzenel ,3-dicarboxylic acid.
• 2-hydroxybenzene-l,3-dicarboxylic acids having an aliphatic hydrocarbon substituent attached to the benzene nucleus in para position relative to the hydroxyl group may be prepared by alkylation of phenol followed by phenation, carboxylation and hydrolysis.
• the presence of a hydrocarbon substituent. attached to the benzene nucleus in para position relative to the hydroxyl group is an essential feature of the present invention, and the alkylation is therefore carried out with an alkylation agent for phenol that attacks the benzene nucleus preferentially in a position para to the hydroxyl group.
• Such agents are monoolefins, which are branched at one or both of the carbon atoms adjacent to the double bond, such as tetra-isobutene and higher polyisobutenes, or precursors of these olefins, such as monohydroxy alkanes in which the hydroxyl group is attached to a tertiary carbon atom or to a carbon atom that is in an alpha-position relative to a tertiary carbon atom in the molecule.
• suitable alkylation agents are l-methylcyclohexene and the product obtained by alkylation of ortho-cresol with cetene-l followed by hydrogenation of the alkylate.
• aromatic dicarboxylic acids according to the invention When used as anti-rust additives in lubricants or fuels, their concentrations can vary within wide limits.
• the additives are preferably added in an amount from about 0.01 to about 5.0 percent w, especially from 0.05 to 1.0 percent w.
• the lubricating oil emulsion is prepared by emulsifying an SAE oil containing 7.5 percent w of commercial viscosity index (VI) improver, 0.75 percent w of a commercial anti-oxidant and l percent w of a commercial anti-scuffing agent with 5 percent w of a synthetic water phase.
• the synthetic water phase which is representative of the water phase in an engine contains 0.6 N HCl, 0.3 N Al(NO and 0.1 N (NH.,)2SO?
• the test conditions of this laboratory corrosion test closely resemble but are much more severe than those prevailing in an ordinary engine.
• EXAMPLE III Since only compounds I, B and C were adequate as rust inhibitors in Example II. These compounds were tested to determine their corrosivity toward lead and copper, two common bearing materials. In the test 0.1 percent w of the indicated compound was added to the same reference oil under identical conditions and the corrosivity of each composition was measured as loss of weight of the copper and lead specimens immersed in the oil. The reference oil alone was of course substantially non-corrosive, but it was otherwise unsuitable because it was not rust inhibited.
• composition B proved too corrosive toward lead it was unsuitable and compositions I and C were further tested.
• composition C is an ashforrning composition that has the above-men- HOOC GOOH wherein X is OH, R is an alkyl group of between more than 12 and 24 carbon atoms, and each R is hydrogen.
• composition of claim 1 wherein the lubricating oil is a mineral oil.
• composition of claim 2 wherein the dicarboxylic acid is 2-hydroxy-5-cetylbenzene-l,3-dicarboxylic acid.
• composition of claim 1 containing from about 0.01 to 5 percent w of the dicarboxylic acid.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Lubricants (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Anti-Oxidant Or Stabilizer Compositions (AREA)

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Citations (4)

• 1970
  • 1970-08-28 US US00068039A patent/US3730485A/en not_active Expired - Lifetime
  • 1970-09-08 JP JP45078258A patent/JPS5020562B1/ja active Pending
  • 1970-09-08 DE DE2044480A patent/DE2044480C3/de not_active Expired
  • 1970-09-08 FR FR7032575A patent/FR2061100A5/fr not_active Expired
  • 1970-09-08 NL NL7013231A patent/NL7013231A/xx unknown
  • 1970-09-08 SE SE12172/70A patent/SE367817B/xx unknown
  • 1970-09-10 GB GB4463369A patent/GB1324162A/en not_active Expired

Patent Citations (4)

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