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
  • C10L1/224—Amides; Imides carboxylic acid amides, imides
• • 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

Definitions

• This invention relates to gasoline compositions adapted to improve the operation ofinternal combustion engines. It is more particularly concerned with motor fuels that provide improved engine operation under cool, humid weather conditions. i
• Carburetor icing occurs in many vehicles when cruising at speeds of 30-60 m.p.h. Such icing is a pronounced problem in the case of certain trucks and cars equipped with carburetors having Venturi-type fuel-air mixing tubes (emulsion tubes). Suchcarburetors are found in trucks and in many European cars. The ice builds up on the tube and restricts the flow of air, thereby enriching the fuel mixture and reducing efficiency. Eventually the engine may stall.
• Gasoline is a mixture of hydrocarbons having 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
• the boiling range of the gasoline reflects on its volatility. Thus, a higher boiling gasoline will be less volatile and give less stalling difliculty. It has been proposed in the art that a gasoline having an A.S.T.M. mid-boiling (50%) point of 310 F. or higher will not be subject to stalling.
• Another object is to pro vide a motor fuel adapted to prevent stalling during engine warmup in cool, humid weather.
• a specific object is to provide an antistall gasoline containing certain Other objects and advantages of this invention will become apparent to those skilled in the art, from the following detailed description.
• this invention provides a motor gasoline, containing a small amount, sufficient to inhibit stalling, of an alkenyl succinamic acid, having between about 10 and about 25 carbon atoms in the alkenyl radical thereof.
• the addition agents contemplated herein are the alkenyl succinamic acids having between about 10 carbon atoms and about 25 carbon atoms in the alkenyl radical. These compounds are readily prepared by reacting an alkenyl succinic acid anhydride in a 1:1 molar ratio with ammonia or with ammonium hydroxide. When reacting the acid anhydride with ammonia, ammonia gas is bubbled through a'solution'of the anhydride in a non-polar solvent, e.g., benzene, toluene, or xylene. Gen: erally, the reaction is carried out by introducing ammonia gas at a slow rate, up to about 126 cc. perminute. The temperaturewill be between about 60 C.
• the free succinamic acid is obtained by neutralizing the ammonium salt with a dilute aqueous acid solution, such as hydrochloric acid andsulfuric acid. It is oftenpreferable to carryout the reaction using an organic solvent, such .aspetroleum ether, benzene, xylene, or toluene.
• a dilute aqueous acid solution such as hydrochloric acid andsulfuric acid. It is oftenpreferable to carryout the reaction using an organic solvent, such .aspetroleum ether, benzene, xylene, or toluene.
• alkenyl'succinic acid anhydrides are well known materials, many of which are commercially available.
• R is an alkenyl radical having between about,
• Non-- limiting examples thereof are decenyl succinic acid anhydride, undecenyl succinic acid anhydride, triisobutenyl succinicacid anhydride, tetrapropenyl succinic acid anhydride, dodecenyl succinic acid anhydride, tetrapropenyl succinic acid anhydride, tetradecenyl succinic acid anhydride, hexadec'enyl succinic acid anhydride, tetraiso butenyl succinic acid anhydride, octadecenyl succinic acid anhydride, eicosenyl succinic acid anhydride, henei-' cosenyl succinic acid anhydride, tricosenyl succinic acid
• the amount of alkenyl succinamic acid that is added to the motor gasoline will vary between about 0.005 percent and about 0.5 percent, by weight, of the gasoline. In preferred practice
• 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 for example, in elude 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.
• CHEVROLET ENGINE TEST A standard Chevrolet engine, equipped with a Holley single downdraft carburetor, was mounted in a cold" chamber refrigerated to about 40 F. A thermocouple was attached to the throttle plate shaft to record the plate temperature. A /2-inch 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 35 F.
• the engine was first run for about minutes at 2000 r.p.m. to bring the engine temperature to equilibrium. The engine was then shut off. When the throttle shaft temperature rose to 40 F., the engine was restarted with the idle speed set at 450 r.p.m. so that the base fuel stalled at idle in 10 seconds or less after at run-time of 20 to 50 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 wifh 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.
• HILLMAN-MINX ENGINE TEST A downdraft Solex FAI 3O carburetor was mounted on a standard 1953 Hillman-Minx engine. The engine was connected to a 7.5 horsepower induction motor and operated under load at 2800 r.p.m. This was equivalent to driving at about 40 miles per hour.
• the Solex carburetor was especially prone to icing on its spraying well which is located in the center of the carburetor throat.
• the spraying well is a cylindrical recorded at one minute intervals for 20 minutes.
• the percent of annular area in the carburetor that is blocked by ice determines the amount of pressure drop across the annular opening in any given installation.
• the amount of throat area blocked by ice is related to the amount of pressure drop above and below the point of ice deposition.
• the relationship between pressure drop and area blocked was determined to calibrate the carburetor, as follows:
• a series of flanged cylinders were prepared, which fitted over the emulsion tube and blocked a portion of the annular opening.
• Each tube had a different, but known size flange. Thus, it was known what fraction of the annular area was blocked by each flange.
• the engine was operated with a flanged cylinder in the carburetor and the amount of pressure drop was noted and recorded. This operation was repeated with each flange.
• Gasoline A was a blend, by volume, of 66 percent catalytically cracked gasoline, 6 percent natural gasoline, 12 percent benzene, 8 percent toluene, and 8 percent butane. It had an A.S.T.M. boiling range of 87 F. to 385 R, with a mid-boiling point of 197 F.
• Gasoline B was a blend, by volume, of 66 percent catalytically cracked gasoline, 2 percent natural gasoline, 12 percent benzene, 8 percent toluene, and 12 percent butane. It had an A.S.T.M. boiling range of F. to
• Gasoline C had the same composition as Gasoline A, but had an A.S.T.M. boiling range of 85 F. to 402 F., with a midboiling point of 198 F.
• Example 1 Into a reaction vessel equipped with a thermometer, condenser, dropping funnel, and agitator, were placed 53.2 grams (0.2 mole) of tetrapropenyl succinic acid anhydride. Agitation was commenced and the contents of the vessel were cooled to 6 C. Then, 28.0 grams (0.8 mole) of ammonium hydroxide was added over a period of 45 minutes. During this period of time, the temperature in the reaction vessel 'was between about 6 C. and about 26 C.
• the thick mass of material (ammonium tetrapropenylsuccinamate) in the flask was diluted with 50 cc. distilled water and cooled to 2 C. Thereupon a gradual addition of 73 cc. of 20% HCl was begun.
• the material in the reaction vessel formed a clear aqueous layer and a very viscous layer of organic material.
• An additional 50 cc. of water and petroleum ether to dissolve the organic matter were added and the addition of HCl was completed.
• the aqueous phase at this point had a pH of 3.
• the material was transferred to a separatory funnel and agitated. The organic layer was separated and filtered.
• the petroleum ether was distilled out at atmospheric pressure and, finally, under 142 mm. mercury pressure at 5062.5 C.
• the product was a very viscous, amber-color fluid, tetrapropenyl succinamic acid.
• Example 2 Into a reaction vessel provided with an agitator, theta mometer, gas inlet tube, and a condenser having a water take-oft trap, were placed 105.2 grams (0.25 mole) of ll-tricosenyl succinic acid anhydride and 500 grams xylene. The contents of the vessel were dried by azeotropic distillation (0.1 cc. water removed). The water take-01f was replaced with a reflux condenser protected with a drying tube containing solid desiccant. Gradually, over 2.75 hours, 3.75 grams of dry ammonia gas was introduced into the reaction mixture and the temperature was slowly raised to 80 C. Then, another 5.2 grams of ammonia gas was introduced at this temperature. The xylene was removed by distillation under reduced pressure leaving the product, ll-tricosenyl suc-. cinamic acid,
• Blends of tetrapropenyl succinamic acid (Example 1) in two concentrations in gasoline I A werev prepared. These blends were subjected to the Chevrolet engine test. Pertinent data are set forth in Table I.
• an alkenyl succinamic acid having between about 10 and about 25 carbon atoms in the alkenyl radical thereof, and being otherwise unsubstituted.

Landscapes

• 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)
• Liquid Carbonaceous Fuels (AREA)

Priority Applications (3)

Applications Claiming Priority (1)

Publications (1)

Family

ID=25147121

Family Applications (1)

Country Status (3)

Cited By (6)

Families Citing this family (1)

Citations (6)

Family Cites Families (4)

• 1959
  • 1959-01-27 US US789269A patent/US2982634A/en not_active Expired - Lifetime
• 1960
  • 1960-01-08 FR FR815190A patent/FR1244786A/fr not_active Expired
  • 1960-01-27 DE DES66809A patent/DE1121404B/de active Pending

Patent Citations (6)

Also Published As

Similar Documents