US2367264A - Beneficiating lubricants, etc. - Google Patents

Beneficiating lubricants, etc. Download PDF

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Publication number
US2367264A
US2367264A US359095A US35909540A US2367264A US 2367264 A US2367264 A US 2367264A US 359095 A US359095 A US 359095A US 35909540 A US35909540 A US 35909540A US 2367264 A US2367264 A US 2367264A
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Prior art keywords
michlers
lubricants
beneficiating
per cent
oil
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Expired - Lifetime
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US359095A
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Robert E Burk
Everett C Hughes
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Standard Oil Co
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Standard Oil Co
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Publication date
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Publication of US2367264A publication Critical patent/US2367264A/en
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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
    • 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
    • C10M2215/066—Arylene diamines
    • 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
    • C10M2215/067—Polyaryl amine alkanes
    • 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
    • C10M2215/08—Amides
    • 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
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
    • 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
    • C10M2215/28—Amides; Imides
    • 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
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double 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
    • 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
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061—Metal salts
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
    • C10M2227/081—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds with a metal carbon bond belonging to a ring, e.g. ferocene
    • 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
    • C10N2010/10—Groups 5 or 15

Definitions

  • the invention comprises the features hereinafter fully described, and particularly pointed out in the claims, the following description setting forth in detail certain illustrative embodiments of the invention, these being indicative however, of but a few of the various ways in which the principle of the invention may be employed.
  • a lubricating-stock for instance which it is desired to protect against deterioration, as in drastic usage in 'an internal combustion engine, is, in accordance with the present invention, provided with a, small amount of a substituted phenylmethane compound, among which the phenyl group may have substituents, or the methane carbon atom may be replaced by substituents, or substituents may occur in both.
  • R is hydrogen, hydrocarbon radical or substituted derivatives of such group, or acyl residue
  • X is carbon, nitrogen, sulphur, S-S, oxy s n, phosphorus, aluminum, boron, arsenic, antimony, OP-O, or OAl-O, and optionally with one or two side groups which 'may be hydrogen, hydrocarbon radical or derivative or substitution product, oxygen-, su1phur-, or nitrogen-derivatives, or halogen except as side group from sulphur or nitrogen.
  • Illustrative of such compounds are Michlers hydrol or tetramethyldiaminobenzhydrol, Michlers thiohydrol, Michlers ketone,
  • thioketone tetramethyldiaminodiphenyl mono or 'dichloromethane, 4,4'-dimethylaminobenzophenonimide, aluminum tri-Michlers hydrolate, Michlers hydrolxanthate, tetramethyldiaminodiphenylamine, tetramethyldiaminodiphenyldisulphide, tetramethyldiaminodiphenylphosphine, p-diaminodiphenyldisulphide, etc.
  • These agents are applied in amount of 0.05 to 5.0 per cent, depending .upon the stock and the particular duty in view. In general, less than 2 per cent is sufiicient.
  • the agent is readily dissolved and disseminated in th oil.
  • the lubricating stock may be of source and character as desired, and for instance 45 to 200 sec. Saybolt Universal at 210 F.
  • agent may be introduced into other petroleum products, such as asphalt, etc., solid products conveniently being molten to permit thorough dissemination of the agent.
  • a composition consisting of a normally nonvolatile hydrocarbon product and a small amount of a substituted aminodiphenylmethane compound having bonded to its central carbon atom an atom of group VI of the periodic system of atomic weight not exceeding that of sulphur.
  • a normally non-volatile hydrocarbon prodnot containing a small amount of Michlers thiohydrol.

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

, Michlers Patented Jan. 16, 1945 2,367 ,264 BENEFICIATIN G LUBRICANTS, ETC.
Robert E. Burk and Everett C. Hughes, Cleveland Heights, Ohio, assignors to The Standard Oil Company, Cleveland, Ohio, a corporation of Ohio No Drawing. Application September 30, 1940, Serial N0. 359,095
2 Claims.
Various agents have been proposed for incorporation in lubricating oils and the like for restraining deterioration, some having more or less utility in such direction. We have now found that a peculiar group of organic compounds of quite complex. character is of outstanding action and utility in petroleum products particularly of low volatile character.
To the accomplishment of the foregoing and related ends, the invention, then, comprises the features hereinafter fully described, and particularly pointed out in the claims, the following description setting forth in detail certain illustrative embodiments of the invention, these being indicative however, of but a few of the various ways in which the principle of the invention may be employed.
A lubricating-stock for instance, which it is desired to protect against deterioration, as in drastic usage in 'an internal combustion engine, is, in accordance with the present invention, provided with a, small amount of a substituted phenylmethane compound, among which the phenyl group may have substituents, or the methane carbon atom may be replaced by substituents, or substituents may occur in both. Compounds are desirable which are of the general formula in which R is hydrogen, hydrocarbon radical or substituted derivatives of such group, or acyl residue, X is carbon, nitrogen, sulphur, S-S, oxy s n, phosphorus, aluminum, boron, arsenic, antimony, OP-O, or OAl-O, and optionally with one or two side groups which 'may be hydrogen, hydrocarbon radical or derivative or substitution product, oxygen-, su1phur-, or nitrogen-derivatives, or halogen except as side group from sulphur or nitrogen. Illustrative of such compounds are Michlers hydrol or tetramethyldiaminobenzhydrol, Michlers thiohydrol, Michlers ketone,
thioketone, tetramethyldiaminodiphenyl mono or 'dichloromethane, 4,4'-dimethylaminobenzophenonimide, aluminum tri-Michlers hydrolate, Michlers hydrolxanthate, tetramethyldiaminodiphenylamine, tetramethyldiaminodiphenyldisulphide, tetramethyldiaminodiphenylphosphine, p-diaminodiphenyldisulphide, etc. These agents are applied in amount of 0.05 to 5.0 per cent, depending .upon the stock and the particular duty in view. In general, less than 2 per cent is sufiicient. The agent is readily dissolved and disseminated in th oil. The lubricating stock may be of source and character as desired, and for instance 45 to 200 sec. Saybolt Universal at 210 F.
Similarly such agent may be introduced into other petroleum products, such as asphalt, etc., solid products conveniently being molten to permit thorough dissemination of the agent.
As an example: With a 20 S. A. E. lubricating stock of Mid-Continent source, there is incorporated 0.25 per cent of MichlerTs thiohydrol. This lubricant, when tested by the common quick test, viz. subjection to a temperature of 300 F. in full exposure to air bubbled through at the rate of thirty liters per hour, for 65 hours, showed a viscosity increase of 57, naphtha insolubles 2.6 per cent, lacquer formation 14.0 percent, and ap pearance rating B minus. In contrast, the oil without the Michlers thiohydrol, similarly tested, showed a viscosity increase of 236, naphtha insolubles 7.7, lacquer formation 43.3, and appearance rating D.
As another example: With a similar oil there aminobenzhydrol. This lubricant, tested as foregoing, showed a viscosity increase of 33, naphtha insoluble 0.3, lacquer formation 4.2, and appearance rating B minus.
As another example: With a similar oil there is incorporated 0.25 per cent of 4,4-dimethylaminobenzophenonimide.
As another example: With a similar oil there is incorporated 0.25 per cent of diaminodiphenyldisulphide.
Particularly advantageous are the compounds of the, above general formula in which X is as stated, except carbon and nitrogen.
Other modes of applying the principle of the invention may be employed, change being'made as regards the details described, provided the fea-- tures stated in any of the following claims, or the equivalent of such, be employed.
We therefore particularly point out and distinctly claim as our invention:
' 1. A composition consisting of a normally nonvolatile hydrocarbon product and a small amount of a substituted aminodiphenylmethane compound having bonded to its central carbon atom an atom of group VI of the periodic system of atomic weight not exceeding that of sulphur.
2. A normally non-volatile hydrocarbon prodnot containing a small amount of Michlers thiohydrol.
ROBERT E. BURK. EVERETT C. HUGHES.
US359095A 1940-09-30 1940-09-30 Beneficiating lubricants, etc. Expired - Lifetime US2367264A (en)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2440530A (en) * 1944-11-04 1948-04-27 Shell Dev Stabilized organic compositions
US2882472A (en) * 1955-11-02 1959-04-14 Sprague Electric Co Electrical capacitors
US2910437A (en) * 1956-03-09 1959-10-27 Universal Oil Prod Co Stabilization of lubricants
US2982729A (en) * 1958-04-02 1961-05-02 Universal Oil Prod Co High temperature lubricating grease containing a p, p'-diaminodiphenylether
US3093586A (en) * 1960-08-11 1963-06-11 Universal Oil Prod Co Stabilization of lubricants
US3156728A (en) * 1960-06-28 1964-11-10 Ethyl Corp Thiobis (2, 6-dialkylaniline) compounds
US3217038A (en) * 1961-12-27 1965-11-09 Universal Oil Prod Co Stabilization of organic substances
US3224972A (en) * 1960-06-28 1965-12-21 Ethyl Corp Stabilization with a 4,4'-thiobis (2,6-dialkylaniline)
US3240703A (en) * 1961-12-27 1966-03-15 Universal Oil Prod Co Stabilization of organic substances
US3259583A (en) * 1962-12-18 1966-07-05 Shell Oil Co Hydraulic fluid

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2440530A (en) * 1944-11-04 1948-04-27 Shell Dev Stabilized organic compositions
US2882472A (en) * 1955-11-02 1959-04-14 Sprague Electric Co Electrical capacitors
US2910437A (en) * 1956-03-09 1959-10-27 Universal Oil Prod Co Stabilization of lubricants
US2982729A (en) * 1958-04-02 1961-05-02 Universal Oil Prod Co High temperature lubricating grease containing a p, p'-diaminodiphenylether
US3156728A (en) * 1960-06-28 1964-11-10 Ethyl Corp Thiobis (2, 6-dialkylaniline) compounds
US3224972A (en) * 1960-06-28 1965-12-21 Ethyl Corp Stabilization with a 4,4'-thiobis (2,6-dialkylaniline)
US3093586A (en) * 1960-08-11 1963-06-11 Universal Oil Prod Co Stabilization of lubricants
US3217038A (en) * 1961-12-27 1965-11-09 Universal Oil Prod Co Stabilization of organic substances
US3240703A (en) * 1961-12-27 1966-03-15 Universal Oil Prod Co Stabilization of organic substances
US3259583A (en) * 1962-12-18 1966-07-05 Shell Oil Co Hydraulic fluid

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