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
  • 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
  • C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
  • C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters

Definitions

• This invention is directed to an improved petroleum distillate fuel containing an N-tertiary-alkyl alkanesulfonamide.
• the fuel shows significant anti-icing and anticorrosion properties as well as excellent carburetor detergency.
• carburetor icing The operation of an internal combustion engine under cool, humid atmospheric conditions is usually accompanied by engine stalling.
• This effect referred to as carburetor icing, is attributed to the formation of ice particles in the carburetor, especially on the throttle plate and surrounding throttle body walls. Ice formation at the edge of the throttle plate reduces air flow to the engine, thereby causing stalling, or the air bleeds or venturi may ice and stall the engine from excessively rich mixtures.
• the sulfonamides utilized according to the present invention are derived from tertiary-alkyl amines, and possess significant properties to produce an improved fuel composition.
• the N-tertiary-alkyl hydrocarbon sulfonamides are more stable to oxidation and thereby do not form oxidized products which in turn cause gummy deposits in gasoline.
• the N-tertiary-alkyl alkanesulfonamides are clear liquids.
• the N-normal alkyl alkanesulfonamides are heterogeneous pastes that tend to separate into difierent phases on standing. This undesirable property causes great inconvenience at the refinery where the sulfonamides are blended with the gasoline.
• N-tertiary-alkyl alkanesulfonamides can be pumped directly, while the N-normal- 3,250,000 Patented May 10, 1966 alkyl alkanesulfonamides must be heated to form a homogeneous mixture before pumping and blending.
• the present invention is directed to an improved distillate fuel containing a minor pro ortion of an N-tertiary-alkyl alkanesulfonamide having the structure RSO NHR wherein R is a saturated alkyl radical having 12 to 30 carbon atoms and may contain chlorine, or a mixture of such alkyl radicals, and R is a tertiaryalkyl group having 8 to 22 carbon atoms, or a mixture of such alkyl groups.
• RSO NHR wherein R is a saturated alkyl radical having 12 to 30 carbon atoms and may contain chlorine, or a mixture of such alkyl radicals, and R is a tertiaryalkyl group having 8 to 22 carbon atoms, or a mixture of such alkyl groups.
• R may be octyl, dodecyl, myristyl, cetyl, stearyl, eicosyl, myricyl or mixtures of alkyl groups having 12 to 14, 14 to 16, or 16 to 20 carbon atoms, hydrocarbon groups derived from White Oil, paraffin wax or petrolatum or mixtures of such hydrocarbon groups.
• R is derived from a tertiary-alkyl monoamine and has the structure where the tertiary carbon atom is bonded to the nitrogen atom, and may be tertiary-octyl, tertiary-nonyl or a mixture of tertiary alkyl groups having 1214 carbon atoms or 18-21 carbon atoms.
• N-tertiary-octyl stearylsulfonamide N-tertiary-eicosyl dodecylsulfonamide, N-tertiary-dodecyl White Oil-sulfonamide, and N-tertiary-C alkyl eicosyl-sulfonamide.
• a preferred embodiment of the present invention is a distillate fuel containing a sulfonamide of the heretoforedefined structure RSO NHR wherein the sum of carbon atoms of R and R is 25 to 35.
• Representative preferred compounds are N-tertiary-octyl White Oil-sulfonamide, N-tertiary-nonyl White Oil-sulfonamide, N-tertiary-C alkyl White Oil-sulfonamide, and N-tertiary-dodecyl paraflin waX-sulfonamide.
• additives are significantly eifective in reducing the stalling tendencies and prevention of corrosion in hydrocarbon distillate fuels boiling in the gasoline and fuel oil range, such as kerosene, gas oils, cracked gas oils, compression-ignition and internal combustion fuels, and the conventional burner and furnace oils.
• the amount of sulfonamides to be added to the fuel ranges from 0.0005 to 0.03 weight percent, depending upon the size of the hydrocarbon molecule in the fuel and the particular benefit desired. In motor gasolines, usually about 0.001 to 0.01 percent is used. In heavier fractions such as kerosenes, diesel fuels or household burner fuels, somewhat higher concentrations may be required. Below 0.0005 percent, the effect of the sulfo-namide on the mineral oil decreases. Above 0.03 percent, the effect levels off and does not increase. The use of higher concentrations is thus not economically advantageous.
• the sulfonamides utilized according to the present invention may be prepared by any known methods for the preparation of sulfonamides. They are conveniently prepared by starting with the aliphatic hydrocarbon desired and reacting with gaseous sulfur dioxide'and chlorine in the presence of actinic light to obtain the hydrocarbon sulfonyl chloride, as described in US. Patents 2,046,090 and 2,202,791. The hydrocarbon sulfonyl chloride thus obtained may be further reacted with the desired amine by conventional techniques, as set forth in US. 2,334,186.
• the hydrocarbon sulfonyl chloride used for the preparation of the sulfonamides of the present invention is derived from the sul-fochlorination of a commercially available petroleum hydrocarbon, such as No. 40 White Oil, which is highly acid-washed parafiinic petrodistilled, C. 284
• the anti-icing properties of the sulfonamides of the present invention were demonstrated in a 6-cylinder Chrysler engine iwhose carburetor operated in an atmosphere of 40 F. and 95% relative humidity. Fuel additive combinations were rated by the number of minutes of open throttle operation at 1800 rpm. under a load necessary to cause stalling while idling. With the .use of commercial, winter-grade gasoline without anti-icing protection, stalling occurs within 0.5 to 1.25 minutes, whereas a rating of 4 minutes and more may be obtained with the use of the sulfonamide additive of the invention.
• the base fuel used in this test had the following inspection data: ASTM D86 distillation 10%118 F., 20% 135 F., 50%252 F., and 90%339 F.; Reid vapor pressure 13.2 p.s.i.
• the carburetor detergency properties of the sulfonamides of the present invention may be demonstrated using a Lausen test engine equipped with a Tillotsen carburetor modified by inserting removable leaflets around the throttle plate. Throughout the test, a portion of the exhaust gases of a second single cylinder engine running at a constant 2500 r.p.m. is introduced into the test carburetor. The test engine was cycled one minute at open throttle under dynamometer load and then for two minutes at idle of 1100:100 r.p.m. for a period of two hours. At the conclusion of the test, the leaflets were removed and rated on the scale: 0 representing bright and shiny to 10 representing very heavy black deposits. The gasoline used was commercially available and had the following inspection data:
• alkanesulfonamides of the present invention are markedly more effective as anti-rust agents than the arylsulfonamides described in US. Patent 2,197,851.
• a widely accepted test for anti-rust properties in distillate fuels is the dynamic rust test as described in the U.S. Military qualifying test, MIL-I-25017, wherein a carefully polished steel specimen is subjected to the corrosive action of an agitated mixture of 300 ml. of depolarized isooctane and 30 ml. of synthetic sea water at F. for a period of 20 hours.
• the sulfonamide additives of the present invention are unexpectedly superior in anti-rust and corrosion prevention as well as in their remarkable detergent properties and anti-icing characteristics.
• Another desirable feature of the sulfonamides is their economical attractiveness, being prepared from commercially, readily available materials, low in cost.
• the sulfonamides of the invention may promote the action of, or have their functions improved by, other surface-active materials such as carboxylic acids, amides, amines, heterocyclic compounds, salts of petroleum sulfonates, alkyl phosphate Salts, ylene-oxide condensates and other such surfaceactive substances.
• other surface-active materials such as carboxylic acids, amides, amines, heterocyclic compounds, salts of petroleum sulfonates, alkyl phosphate Salts, ylene-oxide condensates and other such surfaceactive substances.
• An improved distillate fuel selected from the group consisting of gasoline and fuel oils containing from 0.0005 to 0.03 weight percent of an N-tert.-alkyl alkanesulfonamide having the structure RSO NHR wherein R 15 is selected from the group consist-ing of an alkyl of from 12 to 30 carbon atoms and a chloro-alkyl of from 12 to 30 carbon atoms, and wherein R is a tertiary alkyl having from 8 to 22 carbon atoms and said tertiary-alkyl is bonded to the nitrogen atom by the tertiary carbon atom.

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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)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

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Cited By (2)

Citations (4)

• 0
  • BE BE608553D patent/BE608553A/xx unknown
• 1962
  • 1962-02-23 US US175267A patent/US3250600A/en not_active Expired - Lifetime

Patent Citations (4)

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