US2264999A - Manufacture of lubricants - Google Patents

Manufacture of lubricants Download PDF

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Publication number
US2264999A
US2264999A US284714A US28471439A US2264999A US 2264999 A US2264999 A US 2264999A US 284714 A US284714 A US 284714A US 28471439 A US28471439 A US 28471439A US 2264999 A US2264999 A US 2264999A
Authority
US
United States
Prior art keywords
naphthenate
lubricating
lubricants
oil
manufacture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US284714A
Inventor
John M Musselman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Standard Oil Co
Original Assignee
Standard Oil Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Standard Oil Co filed Critical Standard Oil Co
Priority to US284714A priority Critical patent/US2264999A/en
Application granted granted Critical
Publication of US2264999A publication Critical patent/US2264999A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • 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
    • C10M2215/044Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
    • 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
    • C10M2215/22Heterocyclic 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
    • C10M2215/221Six-membered rings containing nitrogen and carbon only
    • C10M2215/222Triazines
    • 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
    • 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
    • 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
    • C10M2215/30Heterocyclic compounds

Definitions

  • an oil as a desired base as, for instance a mineral oil the viscosity of which may be as desired, I incorporate therewith one or more compounds of detail more particularly referred to hereinafter.
  • a petroleum stock-for example of viscosity of 4'7 to 200 Saybolt Universal at 210 F. may be employed, and with this incorporated a small amount of a ring-containing amine compound of a carboxylic acid which is of at least ten carbon atoms or a naphthenic acid.
  • amines are dicyclohexylamine, diphonylamine, hexamethylene tetramine, and the acids are such acids as stearic, palmitic, lauric, naphthenic, etc.
  • Such compounds are dicyclohexylamine stearate, dicyclohexylamine naphthenate, diphenylamine naphthenate, diphenylamine stearate, diphenylamine laurate, hexamethylene tete ramine naphthena'te, hexamethylene tetramine laurate. hexamethylene tetramine stearate, etc.
  • These compounds are made by reacting the acid and base at moderate temperatures, as for instance 200 F., in a solvent or alone, and it is desirable to employ molecular proportions, variations therefrom resulting in corresponding dilution. The said compounds are applied in quite minor proportion in the composition with the oil,
  • reaction products of the amines with these acids are soluble in mineral oil,.and being of generally rather high boiling points are capable of maintaining stable mixtures.
  • a lubricant comprising a mineral oil with lubricating viscosity and a small amount of a salt of a ring-containing amine compound from the group consisting of di'cyclohexylamine, diphenylamine and hexamethylene tetramine and a carboxylic acid from the group consisting of fatty acids of at least ten carbon atoms and naphthenic acid.
  • a lubricant comprising lubricating viscosity and a small amount of dicyclohexylamine stearate.
  • a lubricant comprising a mineral oil with lubricating viscosity'and a small amount of diphenylamine naphthenate.
  • a lubricant comprising a mineral oil with lubricating viscosity and a small amount of hexamethylene tetramine naphthenate.

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

Patented Dec. {2, 1941 zeta STATES PATET FEECE to The Standard Oil Company,
Cleveland,
Ohio, a corporation of Ohio No Drawing. Application July 15, 1939, Serial No. 284,714
4 Claims.
It has been proposed already to improve the resistance of mineral lubricating oils against deterioration, by adding certain amines. While in the main productive of advantageous results, a difiiculty arises in that under some circumstances of usage which is quite drastic, particularly by high temperature exposure, such products do not last as long as is desirable. I have found however that particularly durable lubricants may be prepared, capable of standing up under various drastic usage conditions, and being particularly effective in inhibiting ring-sticking or inhibiting stcklng of piston rings and accessory oil in internal combustion engines.
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.
Taking an oil as a desired base, as, for instance a mineral oil the viscosity of which may be as desired, I incorporate therewith one or more compounds of detail more particularly referred to hereinafter. Thus, a petroleum stock-for example of viscosity of 4'7 to 200 Saybolt Universal at 210 F. may be employed, and with this incorporated a small amount of a ring-containing amine compound of a carboxylic acid which is of at least ten carbon atoms or a naphthenic acid. Illustrative of such amines are dicyclohexylamine, diphonylamine, hexamethylene tetramine, and the acids are such acids as stearic, palmitic, lauric, naphthenic, etc. Representative of such compounds are dicyclohexylamine stearate, dicyclohexylamine naphthenate, diphenylamine naphthenate, diphenylamine stearate, diphenylamine laurate, hexamethylene tete ramine naphthena'te, hexamethylene tetramine laurate. hexamethylene tetramine stearate, etc. These compounds are made by reacting the acid and base at moderate temperatures, as for instance 200 F., in a solvent or alone, and it is desirable to employ molecular proportions, variations therefrom resulting in corresponding dilution. The said compounds are applied in quite minor proportion in the composition with the oil,
in general it being unnecessary to exceed one per cent thereof in the total composition, and proportions as low as 0.01 per cent may be employed, depending somewhat upon the oil and the partic ular use in View. The reaction products of the amines with these acids are soluble in mineral oil,.and being of generally rather high boiling points are capable of maintaining stable mixtures.
As an example: With a Midcontinent lubricating stock having a viscosity of 300 Saybolt Universal at F., there is incorporated 0.25 per cent of dicycl'ohexylamine stearate.
As another example: With a similar lubricating stock there is incorporated 0.25 per cent of dicyclohexylamine naphthenate.
As another example: With a similar lubricating: stock there is incorporated 0.25 per cent of di-\ phenylamine naphthenate.
As another example: With a similar lubricating stock there is incorporated 0.25 per cent of hexametihylene tetramine naphthenate.
This application is a continuation, in part and to as to common subject matter, of my application Ser. No. 105,747, filed Oct. 15, 1936.
Other modes of applying the principle of the invention may be employed, change being made as regards the details described, provided the features stated in any of the following claims, or the equivalent of such, be employed.
I therefore particularly point out and distinctly claim as my invention:
1. A lubricant comprising a mineral oil with lubricating viscosity and a small amount of a salt of a ring-containing amine compound from the group consisting of di'cyclohexylamine, diphenylamine and hexamethylene tetramine and a carboxylic acid from the group consisting of fatty acids of at least ten carbon atoms and naphthenic acid.
2. A lubricant comprising lubricating viscosity and a small amount of dicyclohexylamine stearate.
3. A lubricant comprising a mineral oil with lubricating viscosity'and a small amount of diphenylamine naphthenate.
4. A lubricant comprising a mineral oil with lubricating viscosity and a small amount of hexamethylene tetramine naphthenate.
' JOHN M. MUSSELMAN.
a mineral oil with
US284714A 1939-07-15 1939-07-15 Manufacture of lubricants Expired - Lifetime US2264999A (en)

Priority Applications (1)

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US284714A US2264999A (en) 1939-07-15 1939-07-15 Manufacture of lubricants

Applications Claiming Priority (1)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2622018A (en) * 1949-10-19 1952-12-16 Socony Vacuum Oil Co Inc Motor fuel
FR2547484A1 (en) * 1983-06-20 1984-12-21 Buckman Labor Inc PROCESS FOR INHIBITING THE DEVELOPMENT AND PROLIFERATION OF MICROORGANISMS IN AQUEOUS MEDIA
US4834892A (en) * 1985-10-03 1989-05-30 Elf France Additives for lubricating oils, their process of preparation and lubricating compositions containing them

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2622018A (en) * 1949-10-19 1952-12-16 Socony Vacuum Oil Co Inc Motor fuel
FR2547484A1 (en) * 1983-06-20 1984-12-21 Buckman Labor Inc PROCESS FOR INHIBITING THE DEVELOPMENT AND PROLIFERATION OF MICROORGANISMS IN AQUEOUS MEDIA
US4505831A (en) * 1983-06-20 1985-03-19 Buckman Laboratories, Inc. Method of preservation of aqueous systems by addition to said systems of quaternary ammonium salts of hexamethylenetetramine
US4834892A (en) * 1985-10-03 1989-05-30 Elf France Additives for lubricating oils, their process of preparation and lubricating compositions containing them

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