US3122559A - Metal soaps of alkyl trimellitic-imide - Google Patents

Metal soaps of alkyl trimellitic-imide Download PDF

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Publication number
US3122559A
US3122559A US20550A US2055060A US3122559A US 3122559 A US3122559 A US 3122559A US 20550 A US20550 A US 20550A US 2055060 A US2055060 A US 2055060A US 3122559 A US3122559 A US 3122559A
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United States
Prior art keywords
imide
soap
metal soaps
alkyl
grease
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
US20550A
Inventor
Benjamin A Bolton
Kenneth E Kolb
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Standard Oil Co
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Standard Oil Co
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Filing date
Publication date
Application filed by Standard Oil Co filed Critical Standard Oil Co
Priority to US20550A priority Critical patent/US3122559A/en
Priority to US115905A priority patent/US3117086A/en
Application granted granted Critical
Publication of US3122559A publication Critical patent/US3122559A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • 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
    • C10M115/00—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof
    • C10M115/08—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof containing nitrogen
    • 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
    • C10M2215/086—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
    • 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • 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
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • R is an alkyl group containing from 4 to about 30 carbon atoms
  • M is selected from the class consisting of alkali metals, alkaline earth metals, zinc and aluminum
  • X is an integer from 1 to 3 corresponding to the valance of M.
  • This soap former is hereinafter spoken of as an alkyl trimellit-imide.
  • the imide is prepared by the reaction of trimellitic anhydride and a primary amine containing from 4 to about 30 carbon atoms under conditions such that the imide is formed.
  • the free carboxyl group present in the imide is then reacted with an alkali metal, an alkaline earth metal, zinc or aluminum to produce the soap.
  • Illustrative of the primary amines which afford the alkyl group portion of the imide are: n-butylamine, tertbutylamine, Isoamylamine, n-hexylamine, n-octylamine, n-dodecylamine, n-tetradecylamine, cetylamine, n-octadecylamine, and triacontylamine.
  • Amines containing from 6 to 20 carbon atoms are particularly suitable.
  • the metal soap contains an alkali metal such as lithium or sodium, an alkaline earth metal such as calcium or barium, zinc, or aluminum. Lithium, zinc, and barium are particularly good soap producing metals.
  • the soap of the invention is an excellent thickener for the hydrocarbon lubricating oils to produce grease type lubricants.
  • the hydrocarbon oil portion of the grease may be any one of those now utilized in the manufacture of grease with conventional soaps and thickeners. While hydrocarbon lubricating oils having S.A.E. grade numbers from through 70 may be utilized, excellent greases are obtained by the use of the viscous hydrocarbon lubricating oils having an S.A.E. number of 40 and upwards.
  • An amount of the soap is introduced into the hydrocarbon lubricating oil to produce the desired amount of thickening; the particular amount needed is dependent upon the type of oil and the particular soap.
  • the grease will contain a major portion of the hydrocarbon lubricating oil and a relatively small amount of the soap.
  • the soap of the imide can then be prepared by dissolving or emulsifying the imide in dilute lithium or sodium-hydroxide.
  • the calcium soap may be prepared by adding C-aCl to dispersions of the sodium or lithium soaps. Both the sodium and lithium soaps of octadecyl trimellit-imide are water insoluble.
  • R is an alkyl group having from 4 to 30 carbon atoms
  • M is selected from the class consisting of alkali metals, alkaline earth metals, zinc and aluminum
  • X is an integer from 1 to 3 corresponding to the valence of M.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Description

United States Patent 3,122,559 METAL STPAPS SF ALKYL TRTMELLITlC-EMTDE Bengamin A. Bolton, Gary, ind, and Kenneth E. Kath, tlorning, N.Y., assignors to Standard Oil fiompany, Chieago, EL, a corp-oration of Endiana No Drawing. Filed Apr. '7, i960, Ser. No. 20,550 4 (Hahn-s. (Cl. 26tl326) This invention relates to metal soaps of alkyl trimellitimide and particularly to greases incorporating said soap.
A new soap has been discovered which has the structure Where R is an alkyl group containing from 4 to about 30 carbon atoms, M is selected from the class consisting of alkali metals, alkaline earth metals, zinc and aluminum, and X is an integer from 1 to 3 corresponding to the valance of M. This soap former is hereinafter spoken of as an alkyl trimellit-imide.
The imide is prepared by the reaction of trimellitic anhydride and a primary amine containing from 4 to about 30 carbon atoms under conditions such that the imide is formed. The free carboxyl group present in the imide is then reacted with an alkali metal, an alkaline earth metal, zinc or aluminum to produce the soap.
Illustrative of the primary amines which afford the alkyl group portion of the imide are: n-butylamine, tertbutylamine, Isoamylamine, n-hexylamine, n-octylamine, n-dodecylamine, n-tetradecylamine, cetylamine, n-octadecylamine, and triacontylamine. Amines containing from 6 to 20 carbon atoms are particularly suitable.
The metal soap contains an alkali metal such as lithium or sodium, an alkaline earth metal such as calcium or barium, zinc, or aluminum. Lithium, zinc, and barium are particularly good soap producing metals.
The soap of the invention is an excellent thickener for the hydrocarbon lubricating oils to produce grease type lubricants. The hydrocarbon oil portion of the grease may be any one of those now utilized in the manufacture of grease with conventional soaps and thickeners. While hydrocarbon lubricating oils having S.A.E. grade numbers from through 70 may be utilized, excellent greases are obtained by the use of the viscous hydrocarbon lubricating oils having an S.A.E. number of 40 and upwards.
An amount of the soap is introduced into the hydrocarbon lubricating oil to produce the desired amount of thickening; the particular amount needed is dependent upon the type of oil and the particular soap. In general, the grease will contain a major portion of the hydrocarbon lubricating oil and a relatively small amount of the soap.
These greases not only possess good appearance and good lubricating qualities but also possess stability at higher temperatures.
Imz'de A mixture of 19.2 g. (0.1 mole) of trimellitic anhydride and 26.9 g. (0.1 mole equivalent) of C /C (/30) primary amine in 415 g. of Xylene was heated and refluxed for 2 hours. 1.8 ml. of water (theoretical) was removed. Components are soluble in xylene at reflux. On cooling overnight a large ppt. formed which was easily removed by filtering. Essentially yield was obtained. Product had an acid number of 122 compared to a theoretical of 127.
Soap
The soap of the imide can then be prepared by dissolving or emulsifying the imide in dilute lithium or sodium-hydroxide. The calcium soap may be prepared by adding C-aCl to dispersions of the sodium or lithium soaps. Both the sodium and lithium soaps of octadecyl trimellit-imide are water insoluble.
Grease In actual grease preparation it is desirable to prepare the soap in situ in the grease base oil. 45 g. of No. 40 base oil and 5 g. of mono octadecyl trimellitimide were stirred at F. The imide dispersed readily. =An aqueous solution of lithium hydroxide was added and heating continued to 350 F. The soap was well dispersed. Milling on a 3-roll mill gave a grease product. (The use of higher soap concentrations gives a higher consistency.) These greases were homogeneous, fairly opaque, and a light tan color.
Thus, having described the invention, what is claimed is:
1. A compound of the formula where R is an alkyl group having from 4 to 30 carbon atoms, M is selected from the class consisting of alkali metals, alkaline earth metals, zinc and aluminum, and X is an integer from 1 to 3 corresponding to the valence of M.
2. The compound of claim 1 wherein R is octadecyl, M is iithium and X is 1.
3. The compound of claim 1 wherein R is octyl, M is sodium and X is 1.
4. The compound of claim 1 wherein R is octadecyl, M is calcium and X is 2.
References (Iited in the file of this patent UNITED STATES PATENTS 2,508,418 Strain et al. May 23, 1950 2,744,119 Walton May 1, 1956 2,882,230 Bartlett et al. Apr. 14, 1959 2,892,778 Carter et al. June 30, 1959

Claims (1)

1. A COMPOUND OF THE FORMULA
US20550A 1960-04-07 1960-04-07 Metal soaps of alkyl trimellitic-imide Expired - Lifetime US3122559A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US20550A US3122559A (en) 1960-04-07 1960-04-07 Metal soaps of alkyl trimellitic-imide
US115905A US3117086A (en) 1960-04-07 1961-06-09 Grease

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US3122559A true US3122559A (en) 1964-02-25

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3217014A (en) * 1963-06-25 1965-11-09 Standard Oil Co N-(carboxyphenyl) trimellitimide derivatives
US3311641A (en) * 1963-06-22 1967-03-28 Sankyo Co Hydrohalides of novel cyclohepta[b]-pyrrole derivatives and a process for preparing the same as well as intermediates and process for their preparations
US3377321A (en) * 1967-04-07 1968-04-09 Standard Oil Co Polyester-imide polymers and a process for preparing polyester-imide polymers from aromatic carboxylic acids

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2508418A (en) * 1947-12-04 1950-05-23 Lilly Co Eli Nu-substituted poly-iodo phthalimides
US2744119A (en) * 1953-01-06 1956-05-01 Merck & Co Inc Phthalyl-alanyl-mercaptoethyl amides and preparation thereof
US2882230A (en) * 1953-09-30 1959-04-14 Exxon Research Engineering Co Lubricating greases containing alkylbeta-amino propionates
US2892778A (en) * 1954-10-25 1959-06-30 California Research Corp Low temperature method for preparing high temperature greases

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2508418A (en) * 1947-12-04 1950-05-23 Lilly Co Eli Nu-substituted poly-iodo phthalimides
US2744119A (en) * 1953-01-06 1956-05-01 Merck & Co Inc Phthalyl-alanyl-mercaptoethyl amides and preparation thereof
US2882230A (en) * 1953-09-30 1959-04-14 Exxon Research Engineering Co Lubricating greases containing alkylbeta-amino propionates
US2892778A (en) * 1954-10-25 1959-06-30 California Research Corp Low temperature method for preparing high temperature greases

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3311641A (en) * 1963-06-22 1967-03-28 Sankyo Co Hydrohalides of novel cyclohepta[b]-pyrrole derivatives and a process for preparing the same as well as intermediates and process for their preparations
US3217014A (en) * 1963-06-25 1965-11-09 Standard Oil Co N-(carboxyphenyl) trimellitimide derivatives
US3377321A (en) * 1967-04-07 1968-04-09 Standard Oil Co Polyester-imide polymers and a process for preparing polyester-imide polymers from aromatic carboxylic acids

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