US3192910A - Two-cycle internal combustion engine fuel - Google Patents

Two-cycle internal combustion engine fuel Download PDF

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Publication number
US3192910A
US3192910A US152678A US15267861A US3192910A US 3192910 A US3192910 A US 3192910A US 152678 A US152678 A US 152678A US 15267861 A US15267861 A US 15267861A US 3192910 A US3192910 A US 3192910A
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Prior art keywords
oil
fuel
methylenebis
carbon atoms
percent
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US152678A
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Thomas H Coffield
Allen H Filbey
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Ethyl Corp
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Ethyl Corp
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Priority to NL285469D priority Critical patent/NL285469A/xx
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • 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
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    • 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
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    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
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    • C10M2223/10—Phosphatides, e.g. lecithin, cephalin
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    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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    • C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
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    • C10M2227/082—Pb compounds
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    • C10M2227/083—Sn compounds
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/26—Two-strokes or two-cycle engines

Definitions

  • Spark ignition engines of the two-cycle type which have no lubricant reservoir, are generally lubricated by including oil in the fuel which lubricates the engine and is eventually burned in the cylinders.
  • oil When insuflicient oil is employed in the fuel-lubricant mixture, excessive engine wear results.
  • fuel/ oil ratios sufficiently low to prolong engine life in terms of wear usually lead to excessive deposition and clogging of the intake and exhaust ports of the engine. In overcoming this problem by increasing the fuel/oil ratio, the operation in turn leads to excessive engine wear.
  • an object of this invention to provide a method for operating a two-cycle internal combustion engine using a fuel/oil ratio low enough to keep engine Wear at an acceptable level and at the same time reduce clogging of the intake and exhaust ports of the engine.
  • a further object of thisiinvention is to provide compositions useful in operating two-cycle spark-ignition internal combustion engines.
  • an embodiment of this invention is the method of operating a two-cycle spark ignitioninternal combustion engine which comprises introducing into the combustion chamber a fuel/oil mixture, the weight ratio of said fuel to said oil being at least about 15/1, said mixture containing as an additive therefor a compound having the formula R R V I no- CHz-QOH I I R1 R1 wherein R is an alkyl group of 1-8 carbon atoms and R is an alpha-branched alkyl group of 3-8 carbon atoms,
  • compositions used in the above method namely a fuel/oil mixture especially adapted for use in two-cycle engines, said fuel comprising leaded hydrocarbon fuel of the gasoline boiling range .and said oil comprising hydrocarbon mineral oil, the weight ratio of said fuel to said oil being at least about 15/ 1, said composition containing a compound having the formula I I R1 R1 wherein R is an alkyl group having 1-8 carbon atoms and 3,192,910 Patented July 6,1955
  • R is an alpha-branched alkyl group having 3-8 carbon atoms, also comprisesan aspect of this invention.
  • certain oil-additive combinations, described below make up part 'of thisinvention.
  • Another embodiment of this invention is as a new compotion containing as an additive therefora compound hav-'- ing the formula 1 R r R I v R1 ii wherein R is an alkyl group havingl-Kcarbon atoms and R is an alpha-branched alkyl grouphaving 3-8 carbon atoms.
  • leaded fuel we mean fuel containing from .about 0.5 to about 6.0 grams of lead per gallon as an 'alkyllead antiknock compound, such at tetraethyllead, tetramethyl lead, mixtures of tetramethyllead and tetraethyllead, the equilibrium mixtures of tetramethyllead, trimethylethyllead, dimethyldiethyllead, methyltriethyllead and tetrar ethyllead produced by chemcial redistribution of tetraethyllead-tetramethyllead mixtures, such as the 50 mol percent50 mol percent mixture, the 25 molpercent-75 mol percent mixture, the 75 mol percent-25 mol percent mixture, and so forth.
  • Aryllead compounds such at tetraphenyllead, can also be used.
  • the concentration of the additive in the finished fuel can be rniniscule and still permit the realization of the benefits of this invention.
  • the additive compounds of this inveni oil over an extended period of time.
  • they effectively reduce intake and exhaust port clogging.
  • they help maintain cleanliness tion serve a purpose entirely unrelated to their recognized use as antioxidants.
  • Antioxidants function to inhibit 'deterioration of the oil while in storage. In doing so they react with and destroy peroxides slowly formed in the vention, however, the additive compounds performian additional and entirely different function.
  • the additives of this invention are added to the oil even just The lead-containing products formed a of the piston skirt, piston underhead and cylinder bore. Such utility is completely unrelated to any antioxidant properties the additive may have.
  • phenolic additive compounds of this invention are: 4,4-methylenebis(Z-tert-butyl 6 methylphenol) 4,4-methylenebis(2-isopropyl-G-methylphenol) 4,4'-methylenebis(2 sec-butyl 6 methylphenol), 4,4- methylenebis(2,6-di-tert-butylphenol) 4,4 methylenebis (2,6-diisopropylphenol), 4,4 methylenebis(2-methyl-6- tert-octylphenol, 4,4 methylenebis[2-ethyl-6 (2-hexyl) phenol], 4,4 methylenebis[2-n-butyl 6 (3' heptyl) phenol], 4,4 niethylenebis(2-n-amyl-6-tert-amylphenol) 4,4 methylenebis(2 isoamyl 6-n-propylphenol), 4,4- methylenebis(2tert-butyl-6-n-l1exylphenol) 4,4
  • compositions of this invention can be prepared by dissolving the phenolic compound of this invention in the oil composition and adding it to fuel, by dissolving the compound in the fuel composition and adding it to oil; or by forming an oil/fuel composition and adding the compound to it.
  • the alkyl lead compound can be added to the fuel, to the oil, or to the fuel-oil combination. It is most preferably to add the compound to hydrocarbon mineral oil, in concentrations of about 0.05 to about 10 weight percent, and to add this oil composition to leaded fuel.
  • the lubricating oil employed in the compositions of this invention is generally a mineral lubricating oil of the type usually employed for the crankcase lubrication of a spark ignition internal combustion engine.
  • a mineral lubricating oil of the type usually employed for the crankcase lubrication of a spark ignition internal combustion engine.
  • the oil may contain other additives and may be blended with other types of oils including vegetable-derived oils such as rapeseed oil and castor oil and synthetic oils such as polymerized olefins and organic polyesters including dioctyl sebacate and trihexyl phosphate.
  • the fuel employed in the compositionsof this invention is primarily a petroleum-derived liquid hydrocarbon of the gasoline boiling range. However, it may, and often does, contain minor proportions of various other ingredients including non-hydrocarbon fuel constituents. Furthermore, the fuel may contain from'0.5 to about 6.5 grams of lead per gallon as an alkyllead antiknock agent to improve the octane quality of the fuel.
  • the compositions of this invention, especially those containing an alkyllead antiknock may also contain-one or more organic halide scavengers.
  • an organic halide scavenger is to convert the lead present in the combustion chamber, after combustion, to lead halide, which is more volatile and more easily exhausted from the engine than lead oxides, which are the normal combustion products when scavengers are not used.
  • the amount of scavenger employed is such as to provide from about 0.75 to 2.5 or more theories of halogen based on the amount of lead present.
  • a theory of halogen is that amount which is required to quantitatively convert the lead present to lead dihalide.
  • a common example, which is widely used in two-cycle service, is Motor Mix, which is a tetraethyllead fluid containing 1.0 theory of chlorine as ethylene dichloride and 0.5 theory of bromine as ethylene dibromide.
  • an aspect of this invention comprises mineral lubricating oil containing 0.05 to 10.0 weight percent of a phenolic compound of the type described ancl an organic halide scavenger in amount sufficient to substantially reduce combustion chamber deposit formation and increase spark plug life in the two-cycle engine.
  • This amount of organic halide scavenger will usually range from about 0.25 to about 7.5 percent, preferably 0.25 to 2.5 percent, by weight of the oil.
  • Another embodiment of this invention includes fuel compositions containing oil with the above amounts of phenolic compound and organic halide scavenger, wherein the fuel/ oil ratio is at least about 15/1.
  • Suitable organic halide scavengers for use in this invention include ethylene dichloride, propylene dichloride, chlorinated benzenes, brominated benzenes and toluenes, brominated propanes, butanes and ethanes.
  • Further scavengers include carbon tetrachloride; propylene dibromide; 2-chloro-2,3-dibromobutane; 1,2,3- tribromopropane; hexachloropropylene; mixed bromoxylenes; 1,4-dibromobutane; 1,4-dichloropentane; B,fi'-dibromodiisopropyl ether; trichlorobenzene; dibromotoluenes; tert-butyl bromide; 2-methyl-2-bromobutane; 2,3,3 trimethyl-Z-brornobutane; t-ert-butyl chloride; 2,3-dimethyl- 2,3-dibromobutane; 2,3-dirnethyl-2,S-dibromohexane; 2- methyl-2,3-dibromobutane; 2-methyl-2,3-dichloroheptane; 2-
  • bromohydrocarbons to the chlorohydrocarbons because the former are less corrosive to the aluminum parts which are widely used in two cycle engines.
  • the most preferred compound is ethylene dibromide and we prefer to use this material in concentrations of 0.25 to 2.0 percent in the oil or 0.75 to 2.5 theories in the finished fuel/ oil composition.
  • the fuel and oil compositions contain, in addition to the phenolic compound of this invention, a detergent additive.
  • a detergent additive any hydrocarbon-soluble detergent can be used. This includes both the ash-forming type and the ashless type. Ordinarily, the ashless detergents, including surfactants, are preferred.
  • suitable detergents include the heavy metal salts of carboxylic or sulfonic acids and the metal alcoholates or phenolates, in all of which the anionic constituent has a large hydrocarbon-soluble radical.
  • the metal constituent is usually an alkaline earth metal, most commonly calcium or barium.
  • the aluminum, zinc and cobalt salts are also used.
  • Other detergents include the metallic salts of the mahogany sulfonic acids, the alkyl phosphoric acids, the alkyl phenols, phtha-lic monoesters, alkylaryl phosphoroamides, long-chain phenolic ether alcohols, naphthenic acids, amino substituted fatty acids, chlorinated fatty acids and acids containing thioether groups.
  • Suitable detergents are the lecithins and various long-chain esters of polyhydric alcohols.
  • reaction products of P 8 Detergent additives which cooperate in an outstanding way with the phenolic additives of this invention include derivatives of carboxylic acids wherein an amide or imidazoline linkage exists.
  • amides made from carboxylic acids of about 6 to about 10 carbon atoms with secondary amines of about the same number of carbon atoms.
  • Such amides have the general formula 0 R1 R-iiN where R is an unsaturated or, more preferably, a saturated aliphatic radical of 5 to 9 carbon atoms and R and R are preferably saturated aliphatic or cycloaliphatic radicals of 6'l0 carbon atoms'.
  • Such compounds wherein R and R are secondary aliphatic radicals are especially preferred.
  • an aspect of this invention comprises mineral lubricating oil containing 0.05 to 10.0 weight percent of a phenolic compound of the type described and a hydrocarbon-soluble detergent in amount sufiicient to substantially reduce sludge formation in the Lambretta motor scooter engine equipped with induction system and four-speed transmission was mounted on a steel frame in the same relative position as on :a motor scooter.
  • the load was absorbed by a 5 horsepower induction motor belted to the exhaust shaft of the transmission. Idle conditions were achieved by allowing the electric motor to free wheel. Engine specifications are shown in Table I.
  • test procedure consisted of operating at full throttle at 4500 r.p.m. for 55minutes followed by a fivern-inute idle period. This cycle was repeated to accumulate a total of test hours after which the cylinder barrel was removed and-the piston and ports were rated for depositbuild-up.
  • Piston skirt 6. 3. 5 3. 5 3.0 4. 0 Piston underhead 3. 0 3. 0 3. 0 3. 0 2. 0 3. 5 Intake ports 8. 0 10. 0 8. 0 8. 0 7. 0 7. 8 C5 linder bore S. 0 8. 0 6. 5 6. 5 5. 0 7. 0 Exhaust ports 2. 3 5. 2 7. D 8. 0 4. 8 6. 2
  • compositionsof this invention are illustrated by the following examples, in which all parts and percentages are by weight unless otherwise designated.
  • T he oils and fuels in preparing the compositions are identified in Tables V and VI as follows:
  • EXAMPLE 4 The procedure of Example 3 is followed except that the phenolic compound is 4,4'-methylenebis(2,6-diisopropylphenol) and the detergent is a copolymer of lauryl inethacrylate and N,N-dimethylaminoethyl methacrylate.
  • This composition is blended with Fuel C in fuel/ oil ratio of 18/ 1.
  • Mixture equilibrium mixture of tetramethyllead, trimethylethyllead, dimethyldiethyllead, trimethylethyllead, and tetraethyllead, iormed by chemical redistribution of a mixture of mol percent tetramethyllead and 50 mol percent tetraethyllead.
  • EXAMPLE 8 To the oil of Example 7 is added 1.0 percent by weight of ethylene dibromide. This composition is blended with Fuel E in fuel/ oil ratio of 20/1.
  • EXAMPLE 9 The oil of Example 8 is blended with Fuel G in the fuel/ oil ratio of 30/1.
  • a fuel/ oil mixture especially adapted for use in two-cycle engines comprising a major proportion of a hydrocarbon fuel of the gasoline boiling range and a minor proportion of a lubricating hydrocarbon mineral oil, the weight ratio of said fuel to said oil being at least above /1, said composition containing as an additive therefor from 0.05 to 10.0 weight percent, based on the oil, of a compound having the formula wherein R is an alkyl group of l-8 carbon atoms and R is an alpha-branched alkyl group of 3-8 carbon atoms.
  • composition of claim 1 wherein R and R are alpha-branched alkyl groups containing 3-8 carbon atoms.
  • said compound is 4,4-methylenebis (2,6-di-tert-butylphenol) 4.
  • a fuel/oil mixture especially adapted for use in two-cycle engines comprising a major proportion of a leaded hydrocarbon fuel of the gasoline boiling range and a minor proportion of a lubricating hydrocarbon mineral oil, the weight ratio of said fuel to said oil being at least about 15/1, said composition containing as an additive therefor from 0.05 to 10.0 weight percent, based on the oil, of a compound having the formula i. in
  • composition especially adapted for blending with two-cycle engine fuel, said composition comprising a major proportion of a lubricating hydrocarbon mineral oil containing 0.05 to 10.0 weight percent of a compound having the formula i R1 7 I!!!
  • R is an alkyl group of 1-8 carbon atoms and R is an alpha-branched alkyl group of 3-8 carbon atoms and additionally containing 0.5 to 5 weight percent of an amide having the formula n) '/R& RFC-N wherein R is an alphatic hydrocarbon radical of 5-9 carbon atoms and R and R are aliphatic hydrocarbon radicals of 6-10 carbon atoms.
  • a composition especially adapted for blending with two-cycle engine fuel comprising a major proportion of a lubricating hydrocarbon mineral oil containing 0.05 to 10.0 weight percent of a compound having the formula I I R1 R1 wherein R is an alkyl group of 1-8 carbon atoms and R is an alpha-branched alkyl group of 3-8 carbon atoms, 0.5 to 5 percent of an amide having the formula internal combustion engine which comprises as the fuel supplying step introducing into the combustion chamber a fuel/oil mixture, the'weight ratio ofsaid fuel to said oil being at least about 15/1, said mixture containing as an additive therefor a compound having the formula wherein R is an alkyl group of 1-8 carbon atoms and R is an alpha-branched alkyl group of 3-8. carbon atoms, igniting said fuel/ oil mixture in said combustion cham ber, thereby producing gaseous combustion products, and causing said combustion products to act on a piston, thereby producing a driving force.

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3310492A (en) * 1964-09-08 1967-03-21 Chevron Res Oils for two-cycle engines containing basic amino-containing detergents and aryl halides
US3390088A (en) * 1965-02-18 1968-06-25 Ethyl Corp Gasoline lubricating oils or organometallic antiknock fluids containing a mixture ofmono-alkylphenol condensation products
US3426738A (en) * 1967-10-16 1969-02-11 Chevron Res Method of operation and lubricant for closed emission internal combustion engines
US4100082A (en) * 1976-01-28 1978-07-11 The Lubrizol Corporation Lubricants containing amino phenol-detergent/dispersant combinations
US4740321A (en) * 1982-06-07 1988-04-26 The Lubrizol Corporation Two-cycle engine oils containing sulfurized alkyl phenols
US4743389A (en) * 1982-11-30 1988-05-10 Mobil Oil Corporation N-alkyl amides as friction-reducers for lubricants and fuels
EP0818524A1 (en) * 1996-07-08 1998-01-14 Chimec S.P.A. Method and additive to increase yield in thermal conversion operations within petroleum plants

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1649485A (en) * 1926-10-18 1927-11-15 Orelup John Wesley Fuel for internal-combustion engines
US1692784A (en) * 1925-01-23 1928-11-20 Boyce Ite Products Inc Fuel and fuel ingredients
GB795390A (en) * 1955-10-21 1958-05-21 Exxon Research Engineering Co Fuel composition
GB795658A (en) * 1956-02-20 1958-05-28 Shell Res Ltd Improved lubricating oil compositions and fuels suitable for use in two-stroke internal combustion engines
US2944086A (en) * 1955-09-23 1960-07-05 Ethyl Corp 1, 1-bis(3, 5-dialkyl-4-hydroxyphenyl) methanes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1692784A (en) * 1925-01-23 1928-11-20 Boyce Ite Products Inc Fuel and fuel ingredients
US1649485A (en) * 1926-10-18 1927-11-15 Orelup John Wesley Fuel for internal-combustion engines
US2944086A (en) * 1955-09-23 1960-07-05 Ethyl Corp 1, 1-bis(3, 5-dialkyl-4-hydroxyphenyl) methanes
GB795390A (en) * 1955-10-21 1958-05-21 Exxon Research Engineering Co Fuel composition
GB795658A (en) * 1956-02-20 1958-05-28 Shell Res Ltd Improved lubricating oil compositions and fuels suitable for use in two-stroke internal combustion engines

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3310492A (en) * 1964-09-08 1967-03-21 Chevron Res Oils for two-cycle engines containing basic amino-containing detergents and aryl halides
US3390088A (en) * 1965-02-18 1968-06-25 Ethyl Corp Gasoline lubricating oils or organometallic antiknock fluids containing a mixture ofmono-alkylphenol condensation products
US3426738A (en) * 1967-10-16 1969-02-11 Chevron Res Method of operation and lubricant for closed emission internal combustion engines
US4100082A (en) * 1976-01-28 1978-07-11 The Lubrizol Corporation Lubricants containing amino phenol-detergent/dispersant combinations
US4740321A (en) * 1982-06-07 1988-04-26 The Lubrizol Corporation Two-cycle engine oils containing sulfurized alkyl phenols
US4743389A (en) * 1982-11-30 1988-05-10 Mobil Oil Corporation N-alkyl amides as friction-reducers for lubricants and fuels
EP0818524A1 (en) * 1996-07-08 1998-01-14 Chimec S.P.A. Method and additive to increase yield in thermal conversion operations within petroleum plants

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