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
  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives 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
  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
• • 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
  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/043—Mannich bases
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

• This invention relates to the preparation of a novel oil composition which flows at lower temperatures than the base stock from which it is prepared. More particularly, the invention relates to the preparation of a lubricating oil composition containing two diflerent additives which cooperate to give the lubricant an unexpectedly low stable pour point.
• pour depressors for waxy mineral lubricating oils can be made by a Friedel-Crafts condensation of long chain aliphatic compounds such as chlorinated paraflin wax with aromatic compounds such as naphthalene.
• Small amounts, e. g. 0.1% to 2.0%, of such pour depressors may lower the A. S. T. M. pour point of a waxy mineral lubricating oil, for example, from +30 F. down to a temperature ranging from F. to as low as 35 F. or lower, depending upon the particular type of oil used, the nature and method of preparation of the pour depressor, and the concentration in which the lat ter is used.
• the blend may still have a 40 or 50 higher stable pour point, of the order of or F., as determined by the Test "12" pour stability test, described in Oil and Gas Journal, vol. 42, No. '7, pp. 103-106 (June 24, 1943) In this test the samples of oil are subjected to a series of temperature cycles rangin from F. to higher levels to simulate the rise and fall of temperature during a winter season.
• pour depressor Another type of pour depressor which is known to the art is a polymeric material obtained by the pyrolysis of fatty acid halides and the like at a temperature of 400 to 750 F. Such materials and their effect in lowering the pour point of waxy lubricating oils are described in E. Liebers U. S. Patent 2,251,550, issued August 5, 1941. Products of this type have been found to lower the pour point to as low as --30 F. However, as in the case of the alkyl-aromatic condensation products described above, these pyroliz ed acyl halides exhibit instability in pour point under fluctuations of temperature, as determined by applying Test V, as described above.
• the alkyl-aromatic condensation product which is used as one of the additives in accordance with the present invention may be more strictly defined as a high molecular weight condensation product of a long. chain aliphatic compound with an aromatic compound selected from the class consisting of aromatic hydrocarbons and hydroxy and amino derivatives thereof.
• the polymeric acyl halide derivative. as employed in the present invention may be defined as a polymeric compound prepared by pyrolyzing,
• a compound of the formula RCOX where R is an alkyl or aromatic-alkyl radical having at least 10 carbon atoms in an aliphatic chain, and X is a halogen.
• R is an alkyl or aromatic-alkyl radical having at least 10 carbon atoms in an aliphatic chain
• X is a halogen.
• compounds suitable for forming such a polymeric product are stearyl chloride, phenylstearyl chloride, behenyl chloride, palmityl chloride, and the like.
• the alkyl-aromatic type pour depressor may be prepared by any of the large number of methods known to the art, one of the earliest of which was disclosed in U. S. Patent 1,815,022.
• the aromatic compound to be used may be either an aromatic hydrocarbon such as naphthalene, diphenyl, benzene, toluene, amyl-benzene, anthracene, etc., or various hydroxy and amino derivatives of aromatic hydrocarbons, such as phenol, naphthol, cresol, aniline, xylidine, etc.
• the long chain aliphatic compound is preferably a material such as parafiin wax which is chlorinated to a chlorine content of about 10% to about 20%.
• chlorinated wax or equivalent material may be dehydrochlorinated to produce correspondin olefins and the olefins may be condensed with the aromatic compound.
• Other long chain aliphatic compounds may be used, preferably having more than 10 aliphatic carbon atoms, such as stearic acid, stearyl chloride, octadecyl alcohol, cetyl alcohol, etc.
• condensation products are preferably made by the use of a Friedel-Crafts type catalyst such as aluminum chloride, zinc chloride, anhydrous hydrogen fluoride, etc., preferably in the presence 01 an inert solvent such as 1 to 5 volumes of a highly refined kerosene or heavy naphtha or tetrachlorethane, per volume of mixed reactant, followed by hydrolysis and removal of the catalyst and distillation of the reaction product under reduced pressure at a temperature up to about 500 or second additive in accordance with the present invention may be prepared by pyrolyzing an acyl halide or similar compound containing at least carbon atoms in an alkyl group attached to the acyl or COX group, where X is a. halogen.
• a Friedel-Crafts type catalyst such as aluminum chloride, zinc chloride, anhydrous hydrogen fluoride, etc.
• an inert solvent such as 1 to 5 volumes of a highly refined kerosene or heavy naphtha or tetrachlor
• Such acyl halides may be prepared from fatty acids and the like by known processes, for example, by reacting the acid with phosphorus trichloride.
• Suitable acids are the naturally occurring fatty acids, such as stearlc, palmitic, behenic and the like, or the mixtures of wax acids obtained by the oxidation of parafiin wax.
• the acyl halide preferably an acyl chloride, is pyrolized by gently heating at a temperature of about 400 to 750 F. until the evolution of hydrogen chloride has substantially ceased, after which the product is preferably diluted with a suitable solvent and washed free from acid, following which the solvent is removed by distillation at a pressure of 1 to 50 mm. to a temperature of about 500 F.
• the distillation residue which is the desired product, is a viscous, gummy material freely soluble in mineral oils. Further details of the preparation of these products may be found in the aforementioned U. S. Patent 2,251,550.
• the oil base stocks into which the two pri- 'mary additives described above are incorporated are preferably waxy mineral lubricating oils such as a paraflinic lubricating oil base stock or a mixed base, which may have been subjected to any one or more of the commonly used refining .steps, such as distillation, solvent extraction, acid treating, clay treating, etc., as well as partial dewaxing.
• Such oil base stock may either be one which is within the known lubricating oil viscosity range, or it may be an oil of much lower viscosity, such as one which is used in the preparation of hydraulic oils, etc., and which may have a viscosity as low as 40 seconds Saybolt at 100 F.
• the aliphatic-aromatic type additive in proportion of about 0.1 to 2.0%, based on the lubricating oil base stock, and about 0.01 to about 1.5% of the acyl halide polymer, and it is also desirable to adjust the relative proportions of the two additives so that from 1 to 60 parts of the aliphatic-aromatic additive, more preferably 2 to 20 parts of the same, are used for one part of the polymeric acyl halide material.
• EXAMPLE 1 This example illustrates the preparation of a product by the pyrolysis of stearyl chloride and the determination of the A. S. T. M. pour point of blends of various proportions of this product alone in a lubricating oil.
• pour point determinations on a base lubricating oil consisting of a solvent extracted Mid-Continent oil fraction having a Saybolt viscosity at 100 F. of 148 and a viscosity at 210 F. of 42.7 and on blends of this oil with the polymer.
• the "pour stability properties of a lubricating oil containing the abovedescribed polymer and an aliphatic-aromatic pour depressor were tested according to the above-described Test V procedure.
• the aliphatic-aromatic pour depressor was made by condensing about 100 parts by weight of chlorinated paraflin wax having a chlorine content of about 14% with about 15 parts by weight of naphthalene, in the presence of about 40 volumes of refined kerosene solvent per volume of mixed reactant, and in the presence of about 2% parts by weight of aluminum chloride as catalyst, followed by th hydrolysis removal of the catalyst and distillation of the reaction mixture by fire and steam up to about 600 F.
• the distillation residue was blended to a standardized potency and used as a pour depressor concentrate.
• the base oil employed in the test was a solvent extracted Mid-Continent lubricating oil fraction containing 3 /2% of a Pennsylvania bright stock and having a Saybolt viscosity at 100 F. of 148 I and a. viscosity at 210 F. of 42.7, and an A. S. T. M. pour point of +25'F.
• a lubricating composition comprising a major proportion of a waxy mineral lubricating 011, about 0.1% to about 2.0% of a high molecular weight condensation product of chlorinated parafiin wax and naphthalene, and about 0.01% to about 1.5% of a polymeric compound prepared by pyrolyzing a high molecular weight fatty acid chloride at about 400 to about 750 F.
• a lubricating composition comprising a large proportion of a waxy mineral lubricating oil, about 0.1% to about 2.0% of a high molecular weight condensation product of a chlorinated parafiin wax with a, naphthalene and about 0.01% to about 1.5% of a polymeric compound obtained by pyrolyzing stearyl chloride at about 400 to about 750 F.
• a lubricating composition comprising a major proportion of a waxy mineral lubricating oil, about 1% to about 1.25% of a high molecular weight condensation product of chlorinated paramn wax and naphthalene, and about 0.5% to about 0.75% of a polymeric product obtained by pyrolyzing stearyl chloride at about 400 to
• a waxy mineral lubricating oil about 1% to about 1.25% of a high molecular weight condensation product of chlorinated paramn wax and naphthalene, and about 0.5% to about 0.75% of a polymeric product obtained by pyrolyzing stearyl chloride at about 400

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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)

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Applications Claiming Priority (1)

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Citations (3)

• 1946
  • 1946-05-22 US US671662A patent/US2468501A/en not_active Expired - Lifetime
  • 1946-12-06 FR FR937808D patent/FR937808A/fr not_active Expired

Patent Citations (3)

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