US3849320A - Organic compositions containing alkali metal arylcarbamates - Google Patents

Organic compositions containing alkali metal arylcarbamates Download PDF

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Publication number
US3849320A
US3849320A US00310752A US31075272A US3849320A US 3849320 A US3849320 A US 3849320A US 00310752 A US00310752 A US 00310752A US 31075272 A US31075272 A US 31075272A US 3849320 A US3849320 A US 3849320A
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United States
Prior art keywords
composition
antioxidant
oils
lubricating
arylcarbamates
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Expired - Lifetime
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US00310752A
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English (en)
Inventor
R Bridger
E Heiba
S Stournas
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Mobil Oil AS
ExxonMobil Oil Corp
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Mobil Oil AS
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Priority to US00310752A priority Critical patent/US3849320A/en
Priority to JP48129815A priority patent/JPS5052105A/ja
Priority to DE2358432A priority patent/DE2358432A1/de
Priority to FR7342236A priority patent/FR2208969B3/fr
Priority to IT31779/73A priority patent/IT1002008B/it
Priority to NL7316381A priority patent/NL7316381A/xx
Priority to US05/479,739 priority patent/US3997597A/en
Application granted granted Critical
Publication of US3849320A publication Critical patent/US3849320A/en
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/40—Six-membered ring containing nitrogen and carbon only
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • C10M133/18—Amides; Imides of carbonic or haloformic acids
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
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    • C10M2205/024—Propene
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
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    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic 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
    • C10M2215/30—Heterocyclic compounds
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    • C10M2227/02—Esters of silicic acids
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    • C10M2229/02—Unspecified siloxanes; Silicones
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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    • 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
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    • 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—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • antioxidant agents for use in organic compositions, particularly lubricants in the form of lubricating oils and greases have heretofore been suggested.
  • antioxidants e.g., amines or phenolic compounds
  • such antioxidants do not exhibit a sufficiently effective degree of inhibiting oxidation. In general, therefore, these antioxidant additives have not proved to be sufficiently attractive to warrant any extensive industrial application.
  • new and improved lubricant compositions in the form of lubricating oils and greases are provided, containing, as antioxidant agents, certain alkali metal arylcarbamates. More specifically, these carbamates comprise alkali metal arylcarbamates, diarylcarbamates and alkarylcarbamates having the structure:
  • RR NCO M in which R and R are phenyl, naphthyl, alkyl, aryl or hydrogen; at least one of R and R is aryl; and M is selected from the group consisting of Li, Na, K, Rb, Cs or tetraalkyl ammonium.
  • carbamates When the above-described carbamates are incorporated in organic media such as lubricant compositions, in the form of lubricating coils and greases, it is found that they impart a relatively high degree of improve-. ment in alkalinity and are highly effective in inhibiting oxidation of the media into which they are incorporated.
  • the carbamates are employed in minor amounts. In most instances, the carbamates are effectively employed in amounts from about 0.001 to about 5%, and, preferably, from about 0.1 to about 2%, by weight, ofthe total weight of the lubricant composition.
  • the carbamate antioxidant may be effective incorporated in any oil of lubricating viscosity or in a grease composition in which the oil of lubricating viscosity is the vehicle in combination with a suitable thickening agent.
  • the lubricating oils which are improved with the antioxidants of the present invention may include mineral oils and synthetic oils of lubricating viscosities. Of particular significance is the improvement of petroleum distillate lubricating oils having boiling points as high as 650F. or above and also mixtures of such oils.
  • distillate oils is not intended to be restricted to straight-run distillate fractions. These distillate oils can be straight-run distillate oils, catalytically or thermally cracked (including hydro-cracked) distillate oils, or mixtures of straightrun distillate oils, naphthas and the like, with cracked distillate stocks and may be of varying viscosities and pour points.
  • such oils can be treated in ac-' cordance with well-known commercial methods, such as acid or caustic treatment, hydrogenation, solventrefining, clay treatment and the like.
  • the aforementioned antioxidants may also be incorporated in grease compositions.
  • Such greases may comprise a combination of a wide variety of lubricating vehicles and thickening or gelling agents.
  • greases in which the aforementioned carbamates are particularly effective may com prise any of the conventional hydrocarbon oils of lubricating viscosity, as the oil vehicle, and may include mineral oils or mineral oils in combination with synthetic lubricating oils, aliphatic phosphates, esters and di-esters, silicates, siloxanes and oxalkyl ethers and esters.
  • Mineral lubricating oils, preferably employed as the lubricating vehicle may be of any suitable lubricating viscosity range from about 45 S.U.S.
  • oils may have viscosity indexes Varyingfrom below 0 to about 100 or higher. Viscosity indexes from to about are preferred. The average molecular weights of these oils may range from about 250 to about 800.
  • the lubricating oil is employed in the grease composition in an amount sufficient to constitute the balance of the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
  • oil vehicles employed in the novel grease formulations may also comprise mineral oils or combinations of mineral oils with synthetic oils of lubricating viscosity.
  • mineral oils having a viscosity of at least 40 S.U.S. at F., and particularly those falling within the range from about 60 S.U.S. to about 6,000 S.U.S. at 100F. may be employed.
  • synthetic vehicles are employed in addition to mineral oils, as the lubricating vehicle, various compounds of this type may be successfully utilized.
  • Typical synthetic vehicles include: polypropylene, polypropylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di-(2-ethyl hexyl) sebacate, di-(2-ethyl hexyl) adipate, di-butyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphoruscontaining acids, liquid ureas, ferrocene derivatives, hydrogenated mineral oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituted diphenyl ethers typified by a butyl-substituted bis (pphenoxy phenyl) ether, phenoxy phenyl ethers, etc.
  • the lubricating vehicles of the aforementioned improved greases containing the above-described antioxidant carbamates are combined with a grease-forming quantity ofa thickening agent.
  • thickening or gelling agents may include any of the conventional metal salts or soaps; which are dispersed in the lubricating vehicle in grease-forming quantities, in such degree as to impart to the resulting grease composition, the desired consistency.
  • Other thickening agents that may be employed in the grease formation may comprise the nonsoap thickeners, such as surface-modified clays and silicas, aryl ureas, calcium complexes and similar materials. In general, grease thickeners may be employed which do not melt and dissolve when used at the required temperature within a particular environment;
  • any materials which are normally employed for thickening or gelling hydrocarbon fluids for forming greases can be used in preparing the aforementioned improved greases in accordance with the present invention.
  • the alkali metal arylcarbamates of the present invention may be prepared, in general, by reacting an arylamine, diarylamine or alkarylamine having the structure R R NI-I with a derivative of an alkali metal having the structure MX at a temperature from about C. to about 150C., and preferably from about 25C. to about 60C., to produce a product having the structure R R NM; and reacting the product thus produced with carbon dioxide at a temperature from about 0C. to about 60C., and preferably from about C.
  • R and R are phenyl, naphthyl, alkyl, aryl or hydrogen; at least one of R and R is aryl; M is selected from the group consisting of Li, Na, K, Rb, Cs or tetraalkyl ammonium; and X is selected from the group consisting of -I-I, -NH N(CH C I-I phenyl, -OI-I,
  • Example 1 N-Phenyl-l-naphthylamine (29.2 grams, 0.133 mole) was added to an ice-cooled solution of butyl lithium (12 grams, 0.187 mole) in 100 ml of tetrahydrofuran over a period of 30 minutes while the solution was stirred under an argon atmosphere. The rate of addition was determined chiefly by the heat evolved during the reaction. Stirring was continued for 30 minutes and the solution was allowed to warm to room temperature. Dry carbon dioxide was pressed through the solution for 1 hour, and solvent was removed by evaporation in a vacuum.
  • the product so obtained (39.6 grams), melting point 290292C., was shown not to contain N-phenyll -naphthyl-amine by thin layer chromatography, and had minor impurities of lithium pentanoate and solvent.
  • the N-H absorption was absent from the infrared spectrum which exhibited a carbonyl absorption at 6.2 microns.
  • the compound, thus produced had the following structure:
  • Example 2 The procedure described in Example 1 was repeated, except that 34.1 grams of N-[p-(2,4,4-trimethyl-2- pentyl)phenyl]-l-naphthylamine and 7.5 grams of butyl lithium was employed. The resulting compound had the following structure:
  • Example 4 The procedure described in Example 1 was repeated, except that 7.5 grams of butyl lithium and 16.9 grams of diphenylamine was employed. The resulting compound had the structure:
  • Example 2 The procedure described in Example 1 was repeated, except that 7.5 grams of butyl lithium and 39.3 grams of di ⁇ p-(2,4,4-trimethyl-2-pentyl)phenyl]amine was employed.
  • the resulting compound had the following structure:
  • Example 8 The procedure described in Example 1 was repeated, except that 6.8 grams of butyl lithium and 26.1 grams of dodecylaniline was employed. The resulting compound had the following structure:
  • Example 9 The procedure described in Example 1 was repeated, except that 17.3 grams of 2,2,4-trimethyldihydroquinoline and 7.5 grams of butyl lithium was employed. The resulting compound had the following structure:
  • Example 10 A solution of di [p-(2,4,4-trimethyl-2-pentyl)- phenyl]amine (l9.65g., 0.05 mol) and potassium-tertbutoxide (5.6lg., 0.05 mol) in 100 ml tetrahydrofuran was refluxed under on argon atmosphere for 22 hours. The resulting potassium salt precipitated from tetrahydrofuran. The tetrahydrofuran was replaced by adding 1,4-dioxane (200 ml) as the tetrahydrofuran was removed by distillation; A vigorous stream of carbon dioxide was passed through the solution for 1 hour. Upon evaporation of the solvent a yield of 26.9g. of product was obtained. The resulting product had the following structure:
  • Example 1 To a solution of 4g. of the potassium carbamate of Example 10 in 75 ml acetonitrile was added'2.0g. of tetraethylammonium tetrafluoroborate. The solution was stirred 0.5 hours and filtered. To the filtrate was added 35 ml diethyl ether and the solution was filtered again. Evaporation of the solvent yielded 3.15g. of product. The resulting product had the following structure:
  • the alkali metal arylcarbamates of the present invention are outstandingly effective as anti-oxida'nts in organic media such as lubricating oils, and greases in which these lubricating oils are employed as vehicles. It will also be noted that other additives may also be included in the above-described organic compositions which can provide a variety of additional desirable characteristics such as extreme pressure agents, detergents, pour point depressants, stability improvers and viscosity controlagents.
  • composition of claim 1 wherein said composi- I tion comprises an oil of lubricating viscosity. 002111 3.
  • composition of claim 1 wherein said composi- I tion comprises a grease.
  • composition of claim 1 containing from about 0.001 to about 5%, by weight, of said antioxidant.
  • composition of claim 1 containing from about 0.1 to about 2%, by weight, of said antioxidant.
  • composition of claim 1 wherein said antioxidant has the structure: 7 dant has the structure:
  • composition of claim 1 wherein said antioxidant has the structure:

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US00310752A 1972-11-30 1972-11-30 Organic compositions containing alkali metal arylcarbamates Expired - Lifetime US3849320A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US00310752A US3849320A (en) 1972-11-30 1972-11-30 Organic compositions containing alkali metal arylcarbamates
JP48129815A JPS5052105A (OSRAM) 1972-11-30 1973-11-20
DE2358432A DE2358432A1 (de) 1972-11-30 1973-11-23 Alkaliarylcarbamate, -diarylcarbamate und -alkarylcarbamate, deren herstellung, sowie diese enthaltende schmiermittelzusammensetzungen
FR7342236A FR2208969B3 (OSRAM) 1972-11-30 1973-11-27
IT31779/73A IT1002008B (it) 1972-11-30 1973-11-28 Composizione organica contenente arilcarbammati di metalli alca lini
NL7316381A NL7316381A (OSRAM) 1972-11-30 1973-11-29
US05/479,739 US3997597A (en) 1972-11-30 1974-06-17 Alkali metal or tetraalkylammonium arylcarbamates

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5126063A (en) * 1990-09-27 1992-06-30 Mobil Oil Corporation Borated hydroxyalkyl esters of dithiocarbamic acids as multifunctional additives for lubricant compositions
US5698498A (en) * 1993-06-28 1997-12-16 The Lubrizol Corporation Hydroxyalkyl dithiocarbamates, their borated esters and lubricants, functional fluids, greases and aqueous compositions containing the same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1026906B (it) * 1974-12-10 1978-10-20 Snam Progetti Procedimento per la preparazione di sali dell acido carbammico n sostituito

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5126063A (en) * 1990-09-27 1992-06-30 Mobil Oil Corporation Borated hydroxyalkyl esters of dithiocarbamic acids as multifunctional additives for lubricant compositions
US5698498A (en) * 1993-06-28 1997-12-16 The Lubrizol Corporation Hydroxyalkyl dithiocarbamates, their borated esters and lubricants, functional fluids, greases and aqueous compositions containing the same

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IT1002008B (it) 1976-05-20
FR2208969B3 (OSRAM) 1976-10-08
FR2208969A1 (OSRAM) 1974-06-28
JPS5052105A (OSRAM) 1975-05-09
NL7316381A (OSRAM) 1974-06-04

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