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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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
  • C10L1/224—Amides; Imides carboxylic acid amides, imides

Definitions

• This invention relates to gasoline compositions adapted to improve the operation of internal combustion engines. It is more particularly concerned with motor .fuels that provide improved engine operation under cool, humid weather conditions.
• stalling during the warmup period is attributable to the formation of ice on the throttle plate and the carburetor barrel near it.
• the water which forms the ice does not come from the gasoline, i.e., as entrained water, but from the air that enters the carburetor.
• stalling generally occurs in cool, humid Weather, when the temperatures are above about 30 F. and below about 60 F. and the relative humidity is about 65 percent and higher, up to 100 percent.
• the most critical conditions are temperatures of 35-40 F. and 100 percent relative humidity.
• Gasoline is a mixture of hydrocarbonshaving an initial boiling point falling between about 75 F. and about 135 F. and an end-boiling point falling between about 250 F. and about 450 F.
• the boiling range of the gasoline,-oi course, reflects on its volatility. Thus, a higher boiling gasoline will be less volatile and give less stalling difficulty. 'In modern engine operation, however, control of stalling by means of increased volatility is not feasible, because other performance characteristios are afiected.
• this invention provides a motor gasoline containing a small amount, sufiicient to inhibit stalling,
• R is an alkyl group containing between about 10 and about 30 carbon atoms per alkyl group and having a tertiary carbon atom directly attached to the nitrogen atom.
• the amic acids can be made by any method known in the art for preparing such compounds. Preferably, they are produced by warming succinic acid anhydride with a tertiaryalkyl primary monoamine having between about 12 and about 24 carbon atoms per molecule. This can be done readily by heating a mixture of equimolar amounts of the acid anhydride and the tertiarylalkyl primary amine at a temperature of 65- C. for a period of time varying between one and th-reehours. The addition occurs readily without the formation of water.
• amic acids can be prepared by the controlled reaction between equimolar amounts of succinic acid and the amine, with the eliminationof one mole of water per mole of amic acid produced. Care must be exercised, however, to avoid the elimination of two moles of water to form the-cyclic imide.
• the amines utilizable in forming the amic acids are the tertiaryalkyl primary monoamines in which a primary amino group (NH is directly attached to a tertiary carbon atom, and which contains between about 10 and about 30 carbon atoms per tertiaryalkyl group.
• Non-limiting examples of the amines are t-dodecyl primaryamine, t-tetradecyl primary amine, t-pentadecyl primary amine, t-hexadecyl primary amine, t-octadecyl primary amine, t-eicosyl primary amine, t-tetracosyl primary amine, and t-triacontyl primary amine.
• These amines can be prepared by several methods well known to those skilled in the art. Specific methods for preparing the t-alkyl primary amines are disclosed in the Journal of Organic Chemistry, vol. 20, page 295 et seq. (1955). Mixtures of such amines are contemplated.
• polyolefin fraction e.g., polypropylene and polybutylene cuts
• a polyolefin fraction e.g., polypropylene and polybutylene cuts
• succinamic acids contemplated herein are effective to impart antistall properties to motor gasolines.
• the antistall additives of the invention may be used in the gasoline along with other antistall addition agents or other additives designed to impart other improved properties thereto.
• anti-knock agents pre-ignition inhibitors, anti-rust agents, metal-deactivators, dyes, antioxidants, detergents, etc.
• the gasoline may contain a small amount, from about 0.01 percent to about 1 percent, by weight, of a solvent oil or upperlube.
• Suitable oils include Coastal and Mid-Continent distillate oils having viscosities within the range of from about 50 to about 500 S.U.S. at 100 F.
• Synthetic oils such as diester oils, polyalkylene glycols, silicones, phosphate esters, polypropylenes, polybutylenes and the like, may also be used.
• the amine reactants used in the examples are mixtures of pure amines.
• Amine A is a mixture of primary amines having a tertiary carbon atom of a tertiary butyl group attached to the amino (-NH group and containing 12 to 15 carbon atoms per molecule and averaging 12 carbon atoms per molecule.
• This mixture contains, by Weight, about 85 percent t-dodecyl primary amine, about percent t-pentadecyl primary amine, and relatively small amounts, i.e., less than 5 percent amines having less than 12 or more than 15 carbon atoms.
• Amine B is a mixture of tertiary alkyl primary amines containing 18 to 24 carbon atoms per molecule and averaging about carbon atoms per molecule. It has a tertiary carbon attached to the -NH group. It contains, by weight, about 40 percent t-octadecyl primary amine, about percent t-eicosyl primary amine, about 15 percent tdocosyl primary amine, about 10 percent t-tetracosyl amine, and a small amount, less than 5 percent, other amines.
• EXAMPLE 1 A mixture of 100 grams (0.5 mole) of amine A, 50 grams (0.5 mole) of succinic acid anhydride, and 50 grams of xylene, as diluent, was heated with agitation to 80-85 C. for 3 hours to form the succinamic acid. The reaction product was clear and fluid at room temperature.
• EXAMPLE 2 A mixture of 152 grams (0.5 mole) of amine B and 50 grams (0.5 mole) of succinic acid anhydride was stirred for 2 hours at 110 C. to form the amine B succinamic acid.
• a Holley carburetor was used.
• a thermocouple was attached to the throttle plate shaft to record the plate temperature.
• a /Z-lHCh insulating gasket was placed between the carburetor and manifold to prevent heat conduction.
• An asbestos sheet covered the entire manifold system to shield the carburetor from convection and radiation.
• a spray chamber was used to saturate the incoming air with moisture before entering an ice tower which cooled the air to about F.
• the engine was first run for about 10 minutes at 2000 r.p.m. to bring the engine temperature to equilibrium. The engine was then shutoff. When the throttle shaft temperature rose to 40 F., the engine was restarted with the idle speed set at 400 to 500 r.p.m. so that the base fuel stalled at idle in 10 seconds or less after a run-time of 20 to 40 seconds. Run-time means the time that the engine was run at 2000 r.p.m. before returning to idle.
• the base fuel was first tested followed by several concentrations of the additive.
• the system was flushed between tests with the fuel to be run next. Any improvement caused by the additive was reflected in a longer run-time (as compared to the base fuel) to cause stalling in 10 seconds or less when the engine was idled. The more effective the additive, the longer the run-time.
• Gasoline X was made up, by volume, of 63 percent catalytically cracked gasoline, 17 percent straight run gasoline, 8 percent benzene, and 12 percent toluene. It had an ASTM boiling range of 104 F. to 390 F., with a 50 percent distillation (mid-boiling) point of 203 F.
• Gasoline Y comprised, by volume, 66 percent catalytically cracked gasoline, 2 percent straight run gasoline, 12 percent benzene, 8 percent toluene, and 12 percent butanes. It had an ASTM distillation range of F. to 296 F. and a mid-boiling point of 200 F.
• succinamic acids contemplated herein are effective to prevent icing and stalling.
• other additives as defined herein are also useful to prevent stalling.
• R is a tertiary alkyl group containing between about 10 carbon atoms and about 30 carbon atoms and having a tertiary carbon atom directly attached to the nitrogen atom.
• R is a mixture of tertiary alkyl group having a tertiary carbon atom directly attached to the nitrogen atom and comprising about 85 weight percent d odecyl, l

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Organic Chemistry (AREA)
• Combustion & Propulsion (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (11)

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• 0
  • BE BE568364D patent/BE568364A/xx unknown
  • NL NL106289D patent/NL106289C/xx active
  • NL NL232384D patent/NL232384A/xx unknown
• 1958
  • 1958-01-07 US US707460A patent/US2982629A/en not_active Expired - Lifetime
  • 1958-05-09 GB GB14998/58A patent/GB822699A/en not_active Expired
  • 1958-10-04 DE DES60175A patent/DE1086942B/de active Pending

Patent Citations (11)

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