US2363001A - Nonvolatile hydrocarbon products - Google Patents

Nonvolatile hydrocarbon products Download PDF

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US2363001A
US2363001A US509899A US50989943A US2363001A US 2363001 A US2363001 A US 2363001A US 509899 A US509899 A US 509899A US 50989943 A US50989943 A US 50989943A US 2363001 A US2363001 A US 2363001A
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hydrocarbon products
nonvolatile hydrocarbon
per cent
phosphorus
inhibitor
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US509899A
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Everett C Hughes
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Standard Oil Co
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Standard Oil Co
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06Metal compounds
    • C10M2201/065Sulfides; Selenides; Tellurides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/067Polyaryl amine alkanes
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08Amides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08Amides
    • C10M2215/082Amides containing hydroxyl groups; Alkoxylated derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/20Containing nitrogen-to-oxygen bonds
    • C10M2215/202Containing nitrogen-to-oxygen bonds containing nitro groups
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/221Six-membered rings containing nitrogen and carbon only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226Morpholines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26Amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28Amides; Imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/30Heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/10Phosphatides, e.g. lecithin, cephalin

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 bein indicative however, of but a few of the varimay be employed.
  • the hydrocarbon product such as an oil, asphalt, etc.
  • a soluble sulphide of phosphorus having a lower sulphur content than P255, in a small amount.
  • Sulphides of this character are P482, Pass, P386, P453, P483 being particularly desirable.
  • the amount of such phosphorus sub sulphide may be 0.001-2%, and Where the mineral oil is of lubricating character, lubricating viscosities may be as desired, or for instance 45-200 sec. Saybolt Universal at 210 F.
  • Such additional inhibitor may be for instance an amino diphenyl methane derivative, as diamino diphenyl methane, tetramethyl diamino diphemri methane, Michlers hydrol or pp (CH3.CH3.N) 2(CeI-I5) zCHOH, tetramethylene pentamine, diphenylamine, alpha naphthylamine, beta naphthylamine, quinoline, brucine, aceto acetanilide, lecithin, nitrobenzene, nitrotoluene, and such nitrogen containing organic compounds.
  • an amino diphenyl methane derivative as diamino diphenyl methane, tetramethyl diamino diphemri methane, Michlers hydrol or pp (CH3.CH3.N) 2(CeI-I5) zCHOH, tetramethylene pentamine, diphenylamine, alpha naphthylamine, beta naphthy
  • containing the phosphorus sulphides as noted, with or without another inhibitor also have excellent extreme pressure lubricating action.
  • the amount of said additional nitrogen containing inhibitor preferred for use in connection with the above defined sulphide of phosphorus is within the range of 0.1 to 1.0%. However, amounts as low at 0.001% givesubstantial improvements and amounts this low therefore may be used. In general it is not economic to use more than 5%.
  • a normally non-volatile hydrocarbon product containing P48 in effective amount up to 2 per cent to stabilize against oxidation, and including 0.13 per cent of Michlers hydrol.
  • a normally non-volatile hydrocarbon prod- 6 A normally non-volatile hydiocai'bon prodnot containing a sulphide of phosphorus having a lower sulphur content than Pass in eflective amount up to 2 per cent to stabilize against oxi-- dation. and includin 0.001% to 5% of a nitrogen I containing oxidation inhibitor.

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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)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Description

ous ways in which the principle of the invention usually 0.01-0.05%.
Patented Nov. 21, 1944 NONVOLATILE HYDROCABBON PRODUCTS Everett 0. Hughes, Cleveland Heights, Ohio, assignor to The Standard Oil Company, Cleveland, Ohio, a corporation of Ohio No Drawing.
6 Claims.
It has become a custom in the industry to designate as anti-oxidants" or oxidation in hibitors agents which exert an efl'ect of preventing deterioration in hydrocarbon products. Irrespective of any questions of accuracy of such designation, the convenience of the term has led to a quite general acceptance, and the practical effect of such agents is quite generally recognized. In accordance with the present invention, certain improvements along such lines are now made possible, and involving materials which are available without undue cost.
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 bein indicative however, of but a few of the varimay be employed.
The hydrocarbon product, such as an oil, asphalt, etc., is, in accordance with the invention, subjected to the action, in service, of a soluble sulphide of phosphorus having a lower sulphur content than P255, in a small amount. Sulphides of this character are P482, Pass, P386, P453, P483 being particularly desirable. The amount of such phosphorus sub sulphide may be 0.001-2%, and Where the mineral oil is of lubricating character, lubricating viscosities may be as desired, or for instance 45-200 sec. Saybolt Universal at 210 F. Peculiarly, I have found that by adding also another agent which is an oxidation inhibitor, the total sheet of the combination is out of proportion to the additive action merely of the phosphorus sulphide and the other inhibitor, and presents unique advantages; and besides, there is a. lessened tendency to metal corrosion, a matter which is desirable in some usages.
Such additional inhibitor may be for instance an amino diphenyl methane derivative, as diamino diphenyl methane, tetramethyl diamino diphemri methane, Michlers hydrol or pp (CH3.CH3.N) 2(CeI-I5) zCHOH, tetramethylene pentamine, diphenylamine, alpha naphthylamine, beta naphthylamine, quinoline, brucine, aceto acetanilide, lecithin, nitrobenzene, nitrotoluene, and such nitrogen containing organic compounds. Where treating a normally solid hydrocarbon product such as asphalt to prevent its deterioration or so-called oxidation change in service, the addition agents are introduced with the asphalt in molten condition. Mineral oils mumionstv emto 11, 1943, Serial No. 509,899
containing the phosphorus sulphides as noted, with or without another inhibitor, also have excellent extreme pressure lubricating action. The amount of said additional nitrogen containing inhibitor preferred for use in connection with the above defined sulphide of phosphorus is within the range of 0.1 to 1.0%. However, amounts as low at 0.001% givesubstantial improvements and amounts this low therefore may be used. In general it is not economic to use more than 5%.
As an example: To a 20 SA. E. lubricating stock of Mid-Continent origin there is added 0.05% of P4S3 and 0.25% of tetramethyldiaminodiphenylmethane. This lubricant, as tested by subjection to the bubbling through of air at the rate of 30 liters of air per hour for hours at 300 F.. showed a viscosity increase at F. of 20, naphtha, insolubles 0.8%, lacquer formation 6.8, and appearance rating B. In contrast,
the same oil without the addition agents, simi- 0.6% of naphtha insolubles, lacquerformation' 6.0, and appearance rating 13+,
This application is a continuation-in-part of my application Serial Number 332,617, filed April I claim:
1. A normally non-volatile hydrocarbon product containing P483 in effective amount up to 2 per cent to stabilize against oxidation, and including also 0.25 per cent of an amino diphenyl methane derivative.
2. A normally non-volatile hydrocarbon product containing P453 in effective amount up to 2 per cent to stabilize against oxidation, and including also'0.25 per cent of diaminodiphenylmethane.
3. A normally non-volatile hydrocarbon product containing P48: in effective amount up to 2 per cent to stabilize against oxidation, and including 0.13 per cent of Michlers hydrol.
4. A normally non-volatile hydrocarbon prod- 6. A normally non-volatile hydiocai'bon prodnot containing a sulphide of phosphorus having a lower sulphur content than Pass in eflective amount up to 2 per cent to stabilize against oxi-- dation. and includin 0.001% to 5% of a nitrogen I containing oxidation inhibitor.
EVERE'I'I C. HUG;
US509899A 1943-11-11 1943-11-11 Nonvolatile hydrocarbon products Expired - Lifetime US2363001A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3205040A (en) * 1963-02-18 1965-09-07 Hooker Chemical Corp Preparation of stabilized sulfur dichloride

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3205040A (en) * 1963-02-18 1965-09-07 Hooker Chemical Corp Preparation of stabilized sulfur dichloride

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