Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
  • C10L1/2443—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds
  • C10L1/2456—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds sulfur with oxygen and/or nitrogen in the ring, e.g. thiazoles
• • 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
  • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
  • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
• • 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
  • 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
• • 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
  • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
• • 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
  • C10M2215/22—Heterocyclic nitrogen compounds
• • 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
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
• • 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
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/223—Five-membered rings containing nitrogen and carbon only
• • 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
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
• • 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
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
  • C10M2215/226—Morpholines
• • 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
  • C10M2215/30—Heterocyclic compounds
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
  • C10M2219/106—Thiadiazoles
• • 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
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
• • 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
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
  • C10M2223/061—Metal salts
• • 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
  • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
  • C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
• • 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
  • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
  • C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
  • C10M2227/081—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds with a metal carbon bond belonging to a ring, e.g. ferocene
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/14—Electric or magnetic purposes
  • C10N2040/16—Dielectric; Insulating oil or insulators
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/14—Electric or magnetic purposes
  • C10N2040/17—Electric or magnetic purposes for electric contacts
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/252—Diesel engines
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/252—Diesel engines
  • C10N2040/253—Small diesel engines

Definitions

• hydrocarbon oils such as motor fuels boiling within the gasoline boiling range, i.e., gasoline produced from the cracking of petroleum
• gasoline produced from the cracking of petroleum have an undesirable tendency to undergo deterioration on storage, with loss in such valuable properties as light color, low gum content and antiknock values.
• blends of these unstable gasoline compositions with more stable gasolines, such as straight run gasoline frequently also show a tendency to deteriorate upon storage.
• This oxidative deterioration of hydrocarbon oils is considerably ac celerated by traces of polyvalent metals nearly always present in these materials. Copper in particular has a great accelerating effect on oxidative deterioration of most hydrocarbon oils during storage.
• the acid number and sludge content of transformer oil may increase to such an extent that the oil has to be renewed, whereas in gasoline the gummy products formed by this catalyzed deterioration often later cause fouling of engine carburetor and fuel lines.
• hydrocarbon oil compositions with improved stability. It is a further object of the invention to increase the oxidative stability of certain gasoline compositions without affecting the detonation resistance of the gasoline and without increasing either the toxicity of the fuel composition or its tendency to lay down combustion chamber deposits. A still further object of the invention is to provide improved hydrocarbon oil compositions containing metal deactivator compounds which are effective in the presence of alkali.
• each R can be a hydrogen atom, an alkyl radical, an aryl radical, an aralkyl radical or an alkaryl radical or the two Rs together with the wherein each R can be an imino radical or an alkylene radical containing from 1 to 3 carbon atoms and each X is a nitrogen-containing heterocyclic radical containing from 3 to 9 carbon atoms bonded to R in the 2-position such as Z-thiazolyl, 2-pyridyl, 2-quinolyl and 2-isopyrrolyl radicals.
• disubstituted diphenyl pyrroline compounds are used as the complexing agent. These materials have the structural formula:
• each R can be an amino radical or an alkylene radical containing from 1 to 3 carbon atoms and each X is a nitrogen-containi-ng heterocyclic radical containing from 3 to 9 carbon atoms bonded to R in the 2-position such as Z-thiazoly-l, 2-pyridyl, 2-quinolyl, and 2-isopyrrolyl radicals.
• diasubstituted isoindol-ine compounds are capable of complexing various polyvalent metals which act as oxidative catalysts even when these metals are in hydrocarbon oils containing 1-(2'-quino1y1imin0) 3-(2'-isopyrr0lylimin0) isoindoline, l.e.,
• the various 1,3 substituents of the isoindoline compounds and 2,5 substituents of the pyrroline compounds above are preferably limited to nitrogen containing heterocyclic radicals which are bound to the isoindoline or pyrroline compound in the 2-position. 7
• the complexing agents of the invention such as the di-substituted isoindoline compounds of the invention improve the oxidative stability of hydrocarbon compositions containing alkali and certain polyvalent metal, that is when the materials of Formula I are added to gasoline compositions in concentrations sufficient to deactivate the oxidation catalyzing metals contained therein, these metal deactivating compounds did not become water soluble upon extraction of the gasoline with alkali, whereas, conventional deactivators became water soluble and were readily extracted from gasoline with water and/or aqueous sodium hydroxide, when similarly treated.
• 1,3-di(2'-pyridylimino)-isoindoline, 2,5- di-(2-pyridylimino)3,4-diphenylpyrroline and 1,3-di(2'- thiazolylimino)-isoindoline were dissolved in a gasoline.
• 1,3-di(2-pyridylimino)-isoindoline was prepared by the method desired by I. A. Elvidge and R. P. Linstead, I.
• 1,3 di(2' thiazolylimino) isind0line 20 parts by weight of Z-amino-thiazole and 14.5 parts by weight of 1,3-di-imino-isoindoline were dissolved in 400 parts by weight of isobutanol. The solution was boiled under reflux for 8 hours. Evolution of ammonia took place. After cooling 20 parts by weight of green-colored crystals was obtained. After crystallizing in 6400 parts by weight of isobutanol the yield was 18 parts by weight of 1,3-di(2- thiazolylimino)-isoindoline in the form of green-yellow needles. The melting point was 277 C.
• Compound A 2,5-di(2'-pyridylimino)3,4-diphesnyl-pyrroline as Compound B and l,3-di(2-thiazolylimino) isoindoline as Compound C.
• Compound A, Compound B and Compound C each were dissolved in a catalytically cracked gasoline having a boiling range of from about 40 to 200 C., in a concentration of 2.5 p.p.m., 5 p.p.rn. and 6.7 p.p.m., respectively.
• the induction period of the gasoline in fresh conditions and after it had been stored for one week was determined by ASTM Method D525.
• the copper content of is evident from the data set forth above that the copper chelate formed by the 1,3-di(2-pyridylimino)- isoindoline is not catalytically active, so that there is no catalyzed oxidative deterioration of the gasoline.
• the induction period of a catalytically cracked gasoline having a boiling range of from about 40 to about C. was determined by ASTM Method D525. Copper napththenate was then dissolved in the gasoline and the induction period determined. The induction period of similar gasolines containing Compounds A, B and C and copper naphthenate were also determined. The results are set forth in Table III below.
• a catalytically cracked gasoline having a boiling range of from about 40 to about 190 C. was treated with 10% by volume of a 1% by weight caustic soda solution. Cop per naphthenate was then dissolved in the treated gasoline.
• a similar gasoline was treated with caustic soda in the same way and copper napthenate and Compound A were then dissolved in the treated gasoline.
• Similar gasolines containing the Compounds A, Band C were treated with caustic soda as'described above and copper naphthenate was then dissolved in the treated gasoline.
• the induction periods of the gasolines were determined by ASTM Method D525. The results are set forth in Table IV.
• the stability of a mineral oil fraction containing 1,3- di(2' pyridylimino) isoindoline was examined in the S.E.V. test (Publication No. 124, leveraging fiir Isolieriil, by the Schweizeriseher Elektrotechnischer ver, January 1, 1936).
• the mineral oil fraction was a naphthenic spindle oil extracted with sulphur dioxide and having a viscosity of approximately 80 SUS at 100 F. This oil was tested as such and after the addition of 0.01% and 0.02% by weight respectively of 1,3-di(2'-pyridylimino)- isoindoline and disalicylal ethylenediamine.
• the oil was heated to 110 C. in a copper beaker for seven days, a
• the metal deaetivators of Formula I can also be used .in specialty products such as mineral spirits, paint solvents and the like. Particularly beneficial results are generally achieved in the case of liquid hydrocarbon products and especially hydrocarbon distillates.
• the improvement in the oxidative stability of various hydrocarbons by the use of the compounds of Formula I may be obtained over a wide range of concentrations, that is, the concentration of these materials may be as low as 0.1 p.p.m. and as high as 150 p.p.m. depending upon the particular material in which it is incorporated, the severity of the conditions to which the hydrocarbon is to be subjected and the length of time the hydrocarbon base must be protected against deterioration. For example, in most gasolines, jet fuels and other hydrocarbon distillates, the lower concentrations are ordinarily sufficient, that is, up to about 15 p.p.m. and particularly about 1 to about 10 p.p.m. are preferred.
• the metal deactivator of Formula I is'used in gasoline fuels.
• the stabilized gasoline fuel compositions of this invention include thermally or catalytically cracked, thermally or catalytically reformed gasolines or products of sulphuric acid or hydrochloric acid alkylation of lower molecular weight olefins and isoparaffins, e.g., of butylene and isobutane and mixtures thereof.
• Automotive gasoline fuel compositions having a boiling range from about the boiling points of C to C hydrocarbons to about 450 F., are suitable as the hydrocarbon base of the invention. These fuels will preferably have an ASTM Method D-86 distillation range of from about to F. to about 357 to 425 F.
• the stabilized gasoline fuel compositions of the invention will preferably contain an octane-improving amount of an organo-lead antiknock agent, i.e., a lead antidetonant, such as tetralower-alkyl lead compound, for example tetraethyllead, tetramethyllead, diethyl .dimethyl .lead, ethyl trimethyl lead, methyl triethyl lead and mixtures thereof.
• concentration of the lead antiknock agent is generally at least 0.5 cc. per gallon and up to 6 cc. per gallon, more especially at least 1 cc. per gallon and no more than 4 cc.
• a halohydrocarbon scavenger such as ethylene dibromide or a mixture of ethylene dibromide and ethylene dichloride will usually be addedin conjunction therewith, especially in an amount-of from about 1.0 to about 1.5 or 1.6 theories, 1.0 theory being the amount necessary to provide two atoms of halogen per atom of lead in the lead antiknock agent present.
• the gasoline compositions of the invention can also contain other antiknock agents such as iron-pentacarbonyl, dieyclopentadienyl iron, xylindene, N-methylaniline, and the organo-manganese compounds such as described in Brown et al., US. 2,818,417, December 31, 1957, especially methylcyclopentadienyl manganese tricarbonyl, or bis(cyclopentadienyl) manganese.
• additives which may be added to the gasoline compositions of the invention include the various antiicing agents such as the mono-N-alkyl substituted propylenediamines; combustion chamber deposit modifiers such as esters of boric acid, for example, isopropyl 2- methyl-2,4-pentanediol borate, 2-methyl-2,4-pentanediol monoacid borate, bis(1,1,3-trimethyl trimethyleneoxy) boric acid, and the like; corrosion inhibitors such as polymerized linoleic acids and N,C-disubstituted imidazolines; metal deactivators such as N,N-disalicylal-1,2- propanediamine; and dyes, silicone oils, and the like.
• combustion chamber deposit modifiers such as esters of boric acid, for example, isopropyl 2- methyl-2,4-pentanediol borate, 2-methyl-2,4-pentanediol monoacid borate, bis(1,1,
• the lubricating oils to which the compounds of Formula I are added are preferably mineral oils. They can be parafiin base, naphthene base or mixed paratfin-naphthene base distillate or residual oils. Lubricating oils having an SUS viscosity of 100 F. between about 50 and 1,000 may be used. These lubricating oils will usually contain other additives such as detergents and dispersants.
• a preferred lubricating oil for use in the invention is a non-ash forming mineral oil within the SAE -30W range.
• compositions suitable for use according to the invention are listed below.
• Example I Transformer oil containing p.p.m. of 1,3-di(2'- pyridylethylene) -isoind oline.
• Example III Gasoline containing 5 p.p.m. of 1-(2'-thiazolylimino)- 3- (2-pyridy1imino -iso-indoline.
• Example IV Gasoline containing 1 p.p.m. of 1,3-di(2'-pyridylimino)- isoindoline.
• Example V Gas oil containing 50 p.p.m. of 1,3-di(2-isopyrrolylimino) -isoindoline.
• Example VI Mineral lube oil having a viscosity of 320 SUS at 100 F. containing 5 ppm. of 1-(2'-isopyrrolylimino)-3-(2- quinolyl-methylene) -isoindoline.
• Example VII Kerosene containing 20 p.p.m. of a complexing agent having the structural formula:
• Example VIII A gasoline composition contain 10 p.p.m. of a complexing agent having the structural formula:
• Example IX A lubricating oil containing 5 p.p.m. of a complexing agent having the structural formula:
• Example X A gasoline composition containing 10 p;p.m. of a complexing agent of the formula:
• R is selected from the group consisting of hydrogen, alkyl, aryl, aralkyl and alkaryl, with the proviso that the carbon atoms within the R groups which are in the beta position relative to N can be members of a nonacetylenically-unsaturated S-membered hetenocyclic ring in which N is the hetero atom, R is selected from the '1 1 group consisting of imino and alkylene having from 1 to 3 carbon atoms, and X is a heterocyclic nitrogencontaining radical, bonded to R in the 2-position, selected from! the group consisting of Z-thiazolyl, 2-pyridyl, 2- quinolyl, and 2-isopyrroly1.
• composition according to claim 1 wherein the hydrocarbon i1 is a gasoline fuel.
• composition according to claim 1 wherein the hydrocarbon oil is kerosene.
• composition according to claim 1 wherein the hy- 10 drocarbon oil is a crankcase lubricating oil having an SUS viscosity at 100 F. of between 50 and 1000.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
• Lubricants (AREA)
• Pyridine Compounds (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=19752502

Family Applications (1)

Country Status (8)

Cited By (4)

Families Citing this family (1)

Citations (4)

• 0
  • BE BE606624D patent/BE606624A/xx unknown
  • NL NL104899D patent/NL104899C/xx active
  • NL NL254361D patent/NL254361A/xx unknown
• 1961
  • 1961-06-28 US US120178A patent/US3190835A/en not_active Expired - Lifetime
  • 1961-07-27 DE DE19611470630 patent/DE1470630A1/de active Pending
  • 1961-07-27 CH CH882661A patent/CH408256A/de unknown
  • 1961-07-27 DK DK308561AA patent/DK104384C/da active
  • 1961-07-27 GB GB27294/61A patent/GB931436A/en not_active Expired
• 1964
  • 1964-12-31 MY MY196447A patent/MY6400047A/xx unknown

Patent Citations (4)

Also Published As

Similar Documents