Classifications

• • 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
  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
  • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
  • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing

Definitions

• ABSTRACT Liquid hydroearbon fuel compositions are provided containing antiknock quantities of alkali metal salts of alkyl and dialkyl-aminoalkyl phenols.
• This invention relates to liquid hydrocarbon fuel compositions having improved antiknock properties. In one of its aspects, the invention relates more particularly to liquid hydrocarbon fuel compositions intended for use in internal combustion engines containing novel and effective antiknock agents.
• antiknock agents include: aniline and alkali derivatives thereof such as N- methylaniline and N-ethylaniline; phenylenediamines; nitriles, proprionitrile'; tertiary alkyl ethe'rs; tetramethyl lead; and tetraethyl lead.
• aniline and alkali derivatives thereof such as N- methylaniline and N-ethylaniline
• phenylenediamines such as N- methylaniline and N-ethylaniline
• phenylenediamines such as phenylenediamines
• nitriles, proprionitrile' tertiary alkyl ethe'rs
• tetramethyl lead and tetraethyl lead.
• liquid hydrocarbon fuel compositions containing an antiknock quantity of alkali metal salts of alkyl and dialkyl-aminoalkyl phenols. These compoundsare represented by the following general formula:
• these novel phenate salt compounds effect improvement in both Motor Octane Number and Research Octane Number in fuels.
• these novel antiknock additives are employed in amounts from about 0.1 to about 5 percent, and preferably from about 0.1 to about 2 percent, by weight, of the total weight of the fuel composition.
• the antiknock agents of the present invention are prepared, in general, by the following method:
• One mol e of the appropriate phenol is moxed with 1.1 mole of 25 percent aqueous alkyl or dialkyl amine. To this admixture, 1.1 mole of 37 percent formalin is added dropwise, with stirring. The reaction temperature is not. allowed to rise above 25C. for optimum results. After the addition is complete, 200 ml. of saturated salt solution is added and the mixture is extracted three times with 200 ml. ether. The ether fractions are combined and extracted twice with 250 ml. of 15 percent aqueous hydrochloric acid. The acid fractions are then combined, made alkaline (pl-I9) and extracted twice with 200 ml. ether.
• the ether fractions are then combined, dried over anhydrous sodium sulfate, and the ether is evaporated off to yield the desired alkyl or dialkyl aminoalkyl phenol.
• This phenol is transformed to its alkali metal salt by treating it with the corresponding alkali metal hydroxide, hydride, alkoxide or amide in an appropriate solvent such'as tetrahydrofuran, methanol, ethanol or liquid ammonia.
• EXAMPLE 1 Preparation of the lithium slat of 2-dime- 5 thylaminomethyl-4-cresol To a mixture of 120 grams 4-cresol and 180 ml. 25 percent aqueous dimethylamine was added 200 grams of 37 percent formalin, dropwise and with stirring. The temperature was not allowed to rise above 25C. After the addition was completed, 200 ml. of salt solution were added. The mixture was extracted three times with 200 ml. ether, the ether fractions were combined and extracted twice with 250 ml. of 15 percent aqueous hydrochloric acid. The acid fractions were combined, made slightly alkaline (pl-I9) and extracted twice with 200 ml. ether. The ether fractions were combined,
• Lithium hydroxide monohydrate (4.2 grams) was added to a solution of 8.2 grams 2-dimethylaminomethyl-4-cresol in 300 ml. ethanol. The mixture was refluxed under a Soxhlet extractor containing molecular sieves for 3 hours. The mixture was then filtered and the ethanol was evaporated off to yield 7.8 grams of the lithium salt of the above cresol.
• sodium salt employing method (a) had the following l structure: (
• r l H This compound, prepared by the above-described 40 lNO2H'5 procedure was transformed to the potassium salt, em- H ploying method a, and had the following structure:
• the compounds of the present invention will increase the antiknock ratings of liquid hydrocarbon fuels even though other antiknock agents may also be present. It will also be understood that other additives intended for the purpose of imparting other improving properties to the fuel may be employed in combination with the present antiknock compounds. Hence, metal deactivators, antioxidants, anti-rust, anti-stalling and ignition control compounds may also be employed in these fuels.
• a gasoline composition containing an antiknock quantity of at least one member of the group consisting of alkali metal salts'of alkyl aminoalkyl phenols and alkali metal salts of dialkyl aminoalkyl phenols.
• composition of claim 1 wherein said antikn'ock compound comprises the lithium salt of 2 -dimethylaminomethyl-4-cresol.
• composition of claim 1 wherein said antiknock compound comprises the lithium saltvof 2- TABLE I Antiknock effectiveness of alkali metal salts of alkyl and dlalkylaminoalkyl phenols Auti- Antiknock Base knock RON Base compound Conc., fuel, fuel, apprefuel, examples gin/liter RON RON ciation MON Antiknock MON fuel, appre- MON ciation 83.8 1. 3 85. 0 2.5 86. 6 4. 1 81. 6 O. 2 83. 4 1. 2 83. 3 0. 8 82. 6 0. l 82. 9 0.8 83. 5 0. 9 83.3 0. 7 83. (l 0. 4
• composition of claim 1 wherein said antiknock compound comprises the sodium salt of 2- (dimethylaminomethyl)-5-cresol.
• composition of claim 1 wherein said antiknock compound comprises the lithium salt of 2-(diethylaminomethyl)-4-cresol.

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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)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Liquid Carbonaceous Fuels (AREA)

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Citations (4)

• 1972
  • 1972-06-19 US US00263904A patent/US3770397A/en not_active Expired - Lifetime
• 1973
  • 1973-05-21 GB GB2407573A patent/GB1387767A/en not_active Expired
  • 1973-06-07 JP JP48063423A patent/JPS4957004A/ja active Pending
  • 1973-06-18 BE BE132412A patent/BE801085A/xx unknown
  • 1973-06-18 IT IT25531/73A patent/IT990757B/it active
  • 1973-06-19 DE DE2331214A patent/DE2331214A1/de active Pending
  • 1973-06-19 NL NL7308543A patent/NL7308543A/xx unknown
  • 1973-06-19 FR FR7322318A patent/FR2189379B1/fr not_active Expired

Patent Citations (4)

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