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US1659149A - Lubricating composition - Google Patents

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US1659149A
US1659149A US636639A US63663923A US1659149A US 1659149 A US1659149 A US 1659149A US 636639 A US636639 A US 636639A US 63663923 A US63663923 A US 63663923A US 1659149 A US1659149 A US 1659149A
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oil
stearanilid
aniline
still
water
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US636639A
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Edward A Nill
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FREDERICK C ACKER
JAMES R DALL
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FREDERICK C ACKER
JAMES R DALL
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Priority to US636639A priority Critical patent/US1659149A/en
Priority to US712392A priority patent/US1659150A/en
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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
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/08Amides [having hydrocarbon substituents containing less than thirty 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
    • C10M2215/08Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • C10M2215/082Amides [having hydrocarbon substituents containing less than thirty carbon atoms] 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
    • C10M2215/24Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/28Amides; Imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • the present invention relates to certain new and useful improvements 1n the manufacture of lubricants and similar oil and wax compounds which are adapted to be 5 used for lubricating and analogous purposes.
  • Ser No. 585,527 filed August 31, 1922, which has now matured into Patent No. 1,17,077,
  • Anilids are formed by the union of a fatty acid with aniline oil, accordin to a reaction similar to that given as fol ows which is for the specific combination of stearic acid and aniline oil.
  • GISHSBOZ e s z 24 41 2 .1 have found that it is extremely difficult or practically impossible to efiect the union of stearic acid with aniline oil to form stearanilid in quantitative yields by merely mixing the two substances and heating them, as the aniline oil boils or distills at a temperature much below that to which the acid must be heated for a free chemical union of the substances and under the high temperatures necessary to effect this union one molecule of water is given off for every molecule of stearanilid formed.
  • aniline is of a poisonous nature, so that it is necessary to form the union in a closed vessel, and just merely boiling the stearic 5o acid with the quantitative amount of aniline oil at the boiling point of aniline oil will not sufiice to bring the two substances into chemical union in suflicient quantities for practical yields.
  • formation and condensation of water causes a considerable amount of agitation within the vessel so that the process cannot be controlled without the mass continually boiling over.
  • the numeral 1 designates a wrought iron vertical still in which two hundred and-eighty-four (284 parts of commercial stearic acid are place
  • a second still 2 is also utilized, and one hundred and elghty-six (186) parts of commercial aniline oil are placed in this second still.
  • a vapor pipe 3 leads from the top of dome of the second still 2 to the top of the first still 1, and extends downwardly through the still 1 to a point slightly spaced from the bottom thereof. The discharge end of the vapor pipe 3 thus extends downwardly below the surface of the stearic acid in the still 1.
  • Each of the stills is provided with a thermometer 4, and some means such as a burner 5 is provided for heating each of the stills.
  • the still 2 which contains aniline oil is heated to a temperature of from 182 C. to 189 C., while the still 1 containing the stearic acid is heated to a temperature of about 235 C., the most favorable working range of temperature being from 230 C. to 240 C.
  • the aniline oil in the still 2 is heated to the boiling point, and the vapors pass over into the heated stearic acid in the still 1.
  • the reaction commences as soon as the aniline vapors begin to pass into the melted acid, providing the latter has been heated to the proper temperature, as indicated above.
  • a vapor pipe 6 leads from the still 1 to a condenser 7 and a suitable receptacle 8 is provided to receive the liquid discharged from the condenser.
  • the water of forma- 100 tion along with any unattached aniline passes over through the condenser 7 and is collected in the receptacle 8.
  • the unattached or uncombined aniline oil is thus recovered, s z that it can be used in a subsequent oper- 105 a ion.
  • the speed of the reaction is entirely dependent on the rapidity of distillation of the aniline oil, and at first practically all of the aniline vapors combine with the stcaric acid, although as the operation continues the proportion of aniline oil carried over with the water of formation increases and the quantity of water going over decreases, the distillation being continued until no more Water goes over, when the reaction is complete and all of the stearic acid has been converted into stearanilid.
  • the aniline oil distillation is then discontinued, and the stearic acid still is heated until no more aniline oil appears at the discharge end of the condenser 7. This assures the removal of all excess of aniline oil from the product, and the result is a quantitative yield of stearanihd, which has been found to have a melting point of from C. to 93 0., according to the purity of the products employed.
  • stills 1 and 2 each have an inlet 9 and an outlet 10, which are controlled in the usual manner by valves or cocks, so that they can be opened and closed as desired.
  • the resulting ield of stearanilid can be drawn off from the still 1 through the outlet 10.
  • stearic acid although it will be understood that other fatty acids, such as, palmitic acid and arachidic acid can be employed.
  • the product will be an anilid of the particular fatty acidthat is used, and in my experiments I have found that these fatty anilids are nonsaponifiable.
  • These anilids althou h being derivatives of fatty acids, are entire ly neutral bodies of hydrocarbon characteristics. Being neutral, the anilids .will not have any corrosive action on metal, and can be used in lubricants or other substances coming into contact with metals without any of the objectionable results which are incident to the fatty acids themselves,"the latter acting very readily upon metal surfaces as is well known.
  • the anilids thus have a very decided advantage over fatty substances when used in lubricants, since they do not corrode the metal surfaces.
  • anilids have a high melting point which is above 200 F., and only a small percentage of these anilids is required to solidify oils to the consistency of grease, and lubricating oils of any desired viscositycan be reduced to a semi-fluid or solid consistency.
  • a high melting point which is above 200 F.
  • lubricating oils of any desired viscosity can be reduced to a semi-fluid or solid consistency.
  • the former luricant is suitable for bearings running at high speeds, and under light loads, while the latter grease is more suitable for use in bearings which run at low speeds under heavy loads, or for use in ordinary grease cups or high pressure lubricating systems. It will be understood that I do not limit the use of the anilid base to the percentages given in the foregoing examples, or to combination anilid base canbe produced in any suitable.
  • I preferably bring the anilid and the wax or oil together and heat the mixture to a temperature of about 205 F. All of the anilid is thereby dissolved, after which the mixture is suddenly chilled to a temperature below the solidifying point thereof.
  • This can be accomplished in any suitable manner, although 1 have found that one convenient way of doing this is to use a cooling cylinder similar to those which are commonly employed in chilling lard compounds.
  • a lubricant well adaptable for use in roller and ball bearings can be produced by dissolving a small percentage of stearanilid in petrolatum.
  • a mixture of 5% stearanilid with 95% zero oil that is a mineral oil having a viscosity of 500 seconds Saybolt at F., forms a transparent lubricant of proper consistency for use in ordinary grease cups or a hi h pressure gun.
  • gasoline, kerosene and the like can be used with the stearanilid. While they have little lubricating value in themselves, they may be employed as vehicles to carry the stearanilid and oil mixture to parts which are difficult to reach. For example, a mixture of 25 parts stearanilid'and 75 parts of kerosene forms a paste suitable for use in the lubrication of phonographs.
  • the products of the invention are not restricted to lubricants, since I have found that by mixing stearanilid with parafline wax or a mixture of stearic acid and paraffine wax, a product suitable for molding into candles is produced.
  • the particular ad- IOU vantage of this candle making product is that the stearanilid gives it a comparativel high melting point, so that the candles wi 1 be harder and better adapted to resist the softening influences of a warm atmosphere. Candles manufactured from this compound will maintain their shape under all usual atmospheric and climatic conditions, and will not soften and bend over under the influence of a warm atmosphere. While stearanilid costs slightly more than stearic acid, it serves as a cheaper substitute for the latter in this candle making compound, since a smaller amount is needed to produce parafline candles of proper hardness or stiffness.
  • WVhiCh is substantially free from water and consists of paraffine oil having a neutral stearanilid mixed therewith to stifien the consistency thereof.
  • a lubricant which is free from water and comprises cylinder oil and neutral stearanilid mixed with the cylinder oil to stiffen the consistency thereof.
  • a lubricant which is free from water and comprises approximately ninety-three percent (93%) cylinder oil and approximately seven percent (7%) neutral stearanilid, the stearanilid serving to stiffen the consistency of the cylinder oil.
  • a lubricating composition which is substantially free from water and comprises a mineral oil having dissolved therein a neutral anilid of a fatty acid to stiffen the consistency and raise the melting point of the composition.
  • a lubricating composition which is substantially free from water and comprises a mineral oil having stearanilid dissolved therein to stiffen the consistency thereof.
  • a lubricatin composition which is substantially free from water and comprises cylinder oil having a neutral anilid of a fatty acid dissolved therein to stiffen the consistency and raise the melting point of the composition.

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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)

Description

Feb, M 11928.
E. A. NlLL LUBRICATING COMPOSITION Filed May 4, 1923 Patented Feb. 14, 1928.
UNITED, STATES PATENT OFFIOE.
EDWARD A. NILL, OF CLEVELAND, OHIO, ASSIGNOB OF ONE-THIRD TO rnnnnnrcx c.
AGREE, OF CLEVELAND HEIGHTS, OHIO, AND ONE-THIRD TO JAMES B. DALL, OI
NOBWALK, OHIO.
LUBRICATING COMPOSITION.
Application filed May 4, 1828. Serial No. 636,639.
I The present invention relates to certain new and useful improvements 1n the manufacture of lubricants and similar oil and wax compounds which are adapted to be 5 used for lubricating and analogous purposes. In a copending applicatlon for Letters Patent of the United States, Serial No. 585,527, filed August 31, 1922, which has now matured into Patent No. 1,17,077,
l granted February 8, 1927, I have disclosed a method of producing a solidified oil or grease lubricant without the use of soap, the solidifying agent, however, being of a saponifiable nature. I have now made a 1 further improvement in the lubricating quality of solidified oils by the use of neutral anilids of fatty acids, such as the anilids of palmitic, stearic and arachidic aclds. These anilids, although being derivatives 'of fatty acids, are entirely neutral bodiesof hydrocarbon characteristics, and possess ng in themselves a lubricating value. Aniline oil is a well known example of an aromatic base, and stearanilid is a product which can zb be broadly termed an acidyl derivative of an aromaticbase.
Anilids are formed by the union of a fatty acid with aniline oil, accordin to a reaction similar to that given as fol ows which is for the specific combination of stearic acid and aniline oil.
Stearic acid. Aniline oil. Stearanilid. Water.
GISHSBOZ e s z 24 41 2 .1 have found that it is extremely difficult or practically impossible to efiect the union of stearic acid with aniline oil to form stearanilid in quantitative yields by merely mixing the two substances and heating them, as the aniline oil boils or distills at a temperature much below that to which the acid must be heated for a free chemical union of the substances and under the high temperatures necessary to effect this union one molecule of water is given off for every molecule of stearanilid formed. Furthermore, aniline is of a poisonous nature, so that it is necessary to form the union in a closed vessel, and just merely boiling the stearic 5o acid with the quantitative amount of aniline oil at the boiling point of aniline oil will not sufiice to bring the two substances into chemical union in suflicient quantities for practical yields. Besides the formation and condensation of water causes a considerable amount of agitation within the vessel so that the process cannot be controlled without the mass continually boiling over.
The foregoing difiiculties have been over-. come by a s ecial process which I have discovered, an while any suitable or a propriate form of ap aratus can be employed for carrying on t e process, one possible form of apparatus is shown by the diagrammatic figure on the accompanying drawing.
Referring to the drawing, the numeral 1 designates a wrought iron vertical still in which two hundred and-eighty-four (284 parts of commercial stearic acid are place A second still 2 is also utilized, and one hundred and elghty-six (186) parts of commercial aniline oil are placed in this second still. A vapor pipe 3 leads from the top of dome of the second still 2 to the top of the first still 1, and extends downwardly through the still 1 to a point slightly spaced from the bottom thereof. The discharge end of the vapor pipe 3 thus extends downwardly below the surface of the stearic acid in the still 1. Each of the stills is provided with a thermometer 4, and some means such as a burner 5 is provided for heating each of the stills. The still 2 which contains aniline oil is heated to a temperature of from 182 C. to 189 C., while the still 1 containing the stearic acid is heated to a temperature of about 235 C., the most favorable working range of temperature being from 230 C. to 240 C.
The aniline oil in the still 2 is heated to the boiling point, and the vapors pass over into the heated stearic acid in the still 1. The reaction commences as soon as the aniline vapors begin to pass into the melted acid, providing the latter has been heated to the proper temperature, as indicated above.
A vapor pipe 6 leads from the still 1 to a condenser 7 and a suitable receptacle 8 is provided to receive the liquid discharged from the condenser. The water of forma- 100 tion along with any unattached aniline passes over through the condenser 7 and is collected in the receptacle 8. The unattached or uncombined aniline oil is thus recovered, s z that it can be used in a subsequent oper- 105 a ion.
The speed of the reaction is entirely dependent on the rapidity of distillation of the aniline oil, and at first practically all of the aniline vapors combine with the stcaric acid, although as the operation continues the proportion of aniline oil carried over with the water of formation increases and the quantity of water going over decreases, the distillation being continued until no more Water goes over, when the reaction is complete and all of the stearic acid has been converted into stearanilid. The aniline oil distillation is then discontinued, and the stearic acid still is heated until no more aniline oil appears at the discharge end of the condenser 7. This assures the removal of all excess of aniline oil from the product, and the result is a quantitative yield of stearanihd, which has been found to have a melting point of from C. to 93 0., according to the purity of the products employed. The
stills 1 and 2 each have an inlet 9 and an outlet 10, which are controlled in the usual manner by valves or cocks, so that they can be opened and closed as desired. The resulting ield of stearanilid can be drawn off from the still 1 through the outlet 10.
In the foregoing example I have used stearic acid, although it will be understood that other fatty acids, such as, palmitic acid and arachidic acid can be employed. The product will be an anilid of the particular fatty acidthat is used, and in my experiments I have found that these fatty anilids are nonsaponifiable. These anilids althou h being derivatives of fatty acids, are entire ly neutral bodies of hydrocarbon characteristics. Being neutral, the anilids .will not have any corrosive action on metal, and can be used in lubricants or other substances coming into contact with metals without any of the objectionable results which are incident to the fatty acids themselves,"the latter acting very readily upon metal surfaces as is well known. The anilids thus have a very decided advantage over fatty substances when used in lubricants, since they do not corrode the metal surfaces.
These anilids have a high melting point which is above 200 F., and only a small percentage of these anilids is required to solidify oils to the consistency of grease, and lubricating oils of any desired viscositycan be reduced to a semi-fluid or solid consistency. For example I find that by melting 10% of stearanilid with of 28 B. parafiine oil a light colored transparent lubricant is obtained, and with 7% of stearanilid. and 93% of cylinder oil a transparent eenish lubricant results. The former luricant is suitable for bearings running at high speeds, and under light loads, while the latter grease is more suitable for use in bearings which run at low speeds under heavy loads, or for use in ordinary grease cups or high pressure lubricating systems. It will be understood that I do not limit the use of the anilid base to the percentages given in the foregoing examples, or to combination anilid base canbe produced in any suitable.
manner, being the product of chemical reaction between aniline oil and one of the fatty acids.
In order to produce a finished lubricant oi smooth and uniform texture, I preferably bring the anilid and the wax or oil together and heat the mixture to a temperature of about 205 F. All of the anilid is thereby dissolved, after which the mixture is suddenly chilled to a temperature below the solidifying point thereof. This can be accomplished in any suitable manner, although 1 have found that one convenient way of doing this is to use a cooling cylinder similar to those which are commonly employed in chilling lard compounds.
As another example of the manner in which this invention can be put into practice, I might mention that a lubricant well adaptable for use in roller and ball bearings can be produced by dissolving a small percentage of stearanilid in petrolatum. A mixture of 5% stearanilid with 95% zero oil, that is a mineral oil having a viscosity of 500 seconds Saybolt at F., forms a transparent lubricant of proper consistency for use in ordinary grease cups or a hi h pressure gun. A mixture of 3% stearanihd and 97% zero oil having a viscosity of 2000 seconds Saybolt, at 100 F., forms a suitable lubricant for gears and bearings carrying extremely heavy pressures. Even gasoline, kerosene and the like can be used with the stearanilid. While they have little lubricating value in themselves, they may be employed as vehicles to carry the stearanilid and oil mixture to parts which are difficult to reach. For example, a mixture of 25 parts stearanilid'and 75 parts of kerosene forms a paste suitable for use in the lubrication of phonographs.
The products of the invention are not restricted to lubricants, since I have found that by mixing stearanilid with parafline wax or a mixture of stearic acid and paraffine wax, a product suitable for molding into candles is produced. The particular ad- IOU vantage of this candle making product is that the stearanilid gives it a comparativel high melting point, so that the candles wi 1 be harder and better adapted to resist the softening influences of a warm atmosphere. Candles manufactured from this compound will maintain their shape under all usual atmospheric and climatic conditions, and will not soften and bend over under the influence of a warm atmosphere. While stearanilid costs slightly more than stearic acid, it serves as a cheaper substitute for the latter in this candle making compound, since a smaller amount is needed to produce parafline candles of proper hardness or stiffness.
For illustrative purposes in describing the invention, I have shown a number of specific ways in which the invention can be used to produce commercial products, although I wish it to be understood that I do not restrict myself to the details of the process or to the particular products mentioned, since many other useful products can be obtained by various combinations and mixtures of an anilid with different kinds of oils and waxes, the anilid serving to stiffen the consistency of the oil or raise the melting point of the wax.
A method of producing the lubricating composition of the present invention is disclosed and claimed in my copending application, Serial No. 238,267, filed December 7 1927, which is a continuation in part of this application.
Having thus described my invention what WVhiCh is substantially free from water and consists of paraffine oil having a neutral stearanilid mixed therewith to stifien the consistency thereof.
2. A lubricant which is free from water and comprises cylinder oil and neutral stearanilid mixed with the cylinder oil to stiffen the consistency thereof.
3. A lubricant which is free from water and comprises approximately ninety-three percent (93%) cylinder oil and approximately seven percent (7%) neutral stearanilid, the stearanilid serving to stiffen the consistency of the cylinder oil.
. 4. A lubricating composition which is substantially free from water and comprises a mineral oil having dissolved therein a neutral anilid of a fatty acid to stiffen the consistency and raise the melting point of the composition.
5. A lubricating composition which is substantially free from water and comprises a mineral oil having stearanilid dissolved therein to stiffen the consistency thereof.
6. A lubricatin composition which is substantially free from water and comprises cylinder oil having a neutral anilid of a fatty acid dissolved therein to stiffen the consistency and raise the melting point of the composition.
In testimony whereof I afiix my signature.
EDWARD A. NILL.
US636639A 1923-05-04 1923-05-04 Lubricating composition Expired - Lifetime US1659149A (en)

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US712392A US1659150A (en) 1923-05-04 1924-05-10 Process of making anilides

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2594286A (en) * 1948-07-08 1952-04-29 Swan Finch Oil Corp Grease and grease base
US2597018A (en) * 1948-05-18 1952-05-20 Robert L Merker Lubricant
US2642397A (en) * 1950-12-22 1953-06-16 Standard Oil Dev Co Lubricating grease compositions
US2958665A (en) * 1957-07-24 1960-11-01 Gen Aniline & Film Corp Non-ionic surface-active gel compositions and preparation thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2597018A (en) * 1948-05-18 1952-05-20 Robert L Merker Lubricant
US2594286A (en) * 1948-07-08 1952-04-29 Swan Finch Oil Corp Grease and grease base
US2642397A (en) * 1950-12-22 1953-06-16 Standard Oil Dev Co Lubricating grease compositions
US2958665A (en) * 1957-07-24 1960-11-01 Gen Aniline & Film Corp Non-ionic surface-active gel compositions and preparation thereof

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