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
  • C10L1/22—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

• Harris Smith ABSTRACT Gasoline fuel compositions containing a dual additive comprising a composition having the general formula R-NHCH CH CH NHCOR is improved by incorporation therewith of a second additive having the general formula R"OCH CH CH NHCH C- H CH NHCOR in which R is an aliphatic hydrocarbon radical having 10-20 carbon atoms; R' is an aliphatic hydrocarbon radical having 9-19 carbon atoms and R" is an aliphatic hydrocarbon radical having 10-l5 carbon atoms.
• R is an aliphatic hydrocarbon radical having 10-20 carbon atoms; R' is an aliphatic hydrocarbon radical having 9-19 carbon atoms and R" is an aliphatic hydrocarbon radical having 10-l5 carbon atoms.
• This invention relates to an improved gasoline composition for internal combustion engines. Particularly, the invention relates to the discovery that the incorporation of a combination of additives in gasoline produces a lower formation of deposits in the upper portion of the induction system, including the carburetor bore area, than that found for gasolines containing a single additive selected from the combination.
• blow-by gasses from the crank case out of the engine into the intake air supply to the carburetor rather than venting these gases to the atmosphere as in the past.
• These blow-by gases contain substantial amounts of deposit forming substances, and it has been observed that some of the substances in the blow-by gases form deposits in and around the throttle plate area of the carburetor. These deposits restrict the flow of air through the carburetor and idle in low speed so that an over-rich fuel mixture results. This condition produces rough idling, engine stalling, and also results in excessive hydrocarbon exhaust emissions to the atmosphere.
• the incorporation of these additives will provide corrosion inhibition and anti-icing.
• amine derivatives such as amides, imides, amines, imidazolines, triazines, pyrimidines, polyamids, low molecular weight polymers, organophosphates, and amine phosphates as well as ordinary ammonium salts of such materials are well known fuel additives which in part increase the operating efficiency of the carburetor system.
• amine derivatives such as amides, imides, amines, imidazolines, triazines, pyrimidines, polyamids, low molecular weight polymers, organophosphates, and amine phosphates as well as ordinary ammonium salts of such materials are well known fuel additives which in part increase the operating efficiency of the carburetor system.
• alkyl substituted diaminoamid derivatives are US. Pat. Nos. 2,805,135; 2,922,707; 2,996,365; 3,251,853; 3,313,607; 3,589,877; 3,653,853; 3,704,109;
• the deposits which are formed in the carburetor system may be due in part to the make up of the motor fuel which is used; but it is believed that deposits are due to a greater extent, at least to foreign matter introduced into the carburetor, through the air intake system since air cleaners are not completely effective.
• Major contributors to air contamination are crank case vapors formed from the crank case, exhaust vapors, dust, smoke and the like.
• the problem with respect to carburetor deposits resulting from air contamination is further aggravated by the positive crank case ventilating system which is employed in many of the recently introduced automotic engines. In engines equipped with a positive crank case ventilating system, fumes and vapors from the crank case are passed through a metering valve into the air intake system of the engine.
• Another source of carburetion deposit is derived from the composition and history of the fuel. Trace contaminants in the fuel which result from its process of manufacture, storage and geographical origin are thought to be responsible for the high molecular varnishes and gums which are deposited over long periods of use.
• Another objective of the invention is to provide gasoline compositions comprising hydrocarbons boiling in the gasoline boiling range with a combination of detergents comprising alkoxy substituted derivatives of propylamides and alkylamine substituted derivatives of propylamides.
• a by-component detergent composition comprising a blend of monoamides A and B having the general struc-
• the first component (A) of the blend is a propylene diamine derivative wherein R and R is a C C fatty aliphatic hydrocarbon radical.
• the second component (B) of the blend is a propylene diamine derivative wherein R is a C C fatty aliphatic hydrocarbon radical and R is a hydrocarbon radical having 10-15 carbon atoms.
• the first detergent component referred to above can be made by reacting a monoalkyl N-substituted propylenediamine derivative with mono carboxcylic acids to form the N,N amide derivative.
• N-aliphatic substituted propylene diamines are N-nonyl propylenediamine, N-tetradecylpropylenediamine, N-tetradecenlpropylenediamine, N-hexadecylpropylenediamine, N-eicosylpropylenediamine, N-cicosenylpropylcnediamine, N- docosylpropylenediamine, and N-docosenylpropylenediamine.
• the aliphatic N- substituent is an alkyl or alkenyl group containing at least 12 and preferably 16-20 carbon atoms are considered to be most effective.
• the N-aliphatic substituted propylenediamines which are considered to form especially effective materials are the N-dodecyl, N-hexadecyl, propylenediamines, and especially the 18 carbon alkyl--, alkenyland the alkadienyl-substituted propylenediamines such as the N- octadecyl-, N-octadecenyl, and N-octadecadienyl propylenediamine.
• N-aliphatic substituted propylenediamine such as are formed when the aliphatic N- substituent is derived from mixed fatty acids obtained from naturally occuring fats and oils, form highly effective materials for use in the composition of the invention.
• the aliphatic N- substituent is a straight chain, monovalent and hydrocarbon radical containing from 10-20 carbon atoms.
• Examples of such mixtures of N-aliphatic substituted propylenediamines are N-tallow propylenediamine,
• propylenediamine 3 propylenediamine where the respective N- substituents are mixed alkyl and unsaturated alkyl groups derived from animal tallow (C -C fatty acids, soybean (C -C fatty acids and coconut (C -C fatty acids.
• These N- aliphatic substituted propylenediamines can be prepared by converting commerially available fatty acids to their corresponding nitriles and thereafter reducing the nitriles with hydrogen to form the primary amine. This primary amine is then treated with acrylonitrile to obtain the corresponding cyanopropyl aliphatic amine which is then hydrogenated to obtain the alkyl substituted propylenediamine.
• Exemplary commercially available N-aliphatic substituted propylenediamines are Duomeen-T and Duomeen-S (products of Armour and Company.) which have gen- N-octadecylpropylenediaminemonooleate N- octadecylpropylenediamin estearate, N-tallow propylenediaminemonoole ate, 'N-soya' propylenediaminemonooleate, and N-coco propylenediaminestearate.
• Duomeen-T and Duomeen-S products of Armour and Company.
• a preferred detergent derivative representative of the above described is prepared by reacting 1 mol of oleic acid which is commercially available and sold under the trademark ACINTOL No. l with 1 mol of N-tallow propylenediamine sold under the trademark KEMAMINE D-974 at a temperature ranging between 50 and 105C. until the removal of 1 mol of water is accomplished.
• the second detergent component of the blend is made byreacting compounds having the general forwherein R" is an aliphatic hydrocarbon radical having -15 carbon atoms with a monocarboxylic acid having 10-20 carbon atoms selected from those described above.
• R" is an aliphatic hydrocarbon radical having -15 carbon atoms
• monocarboxylic acid having 10-20 carbon atoms selected from those described above Such starting-materials are readily commercially available and can be reacted'together at temperatures up to about 105C. in equal molar quantities to eliminate 11 mol of water.
• a preferred material is prepared by reacting 1 mol of oleic acid (Acintol FA. No. l) with N-tridecyloxypropylethylenediamine ('Adogen 583).
• the detergent compositions of the invention can also be made by simultaneously reacting in one vessel equal molar portions'of the N-a'lkyl substituted propylenediamine compounds along with the N-alkoxypropylpropylenediamine derivatives with 2 equivalents of the monocarboxylic acid to form a mixture of the detergent combination.
• the A and B diamine derivatives be present in the final combination in weight ratios of 1:9 to 9:1.
• the individually prepared detergents can be mixed together in these weight ratios for addiis present in concentrations ranging from 0003-015 4 percent by weight of the fuel.
• each individual detergent can be added directly to the gasoline in the appropriate weight ratios and concentrations.
• EXAMPLE 1 In a test device called an Induction System Deposit (ISD) bench apparatus, the performance of the detergent blends was measured in a gasoline designed specifically for lube oil engine tests.
• the bench test apparatus was designed specifically for military and commercial organizations and is described in detail in a publication entitled A Bench Technique for Evaluating the Induction System Deposit Tendencies of Motor Gasolines by A. A. Johnston and E. Dimitroff, SAE Transactions, Vol. (1967), paper No. 660783.
• the test operates by impinging a stream of air propelled fuel onto a preweighed heated deposit-collecting tube made of aluminum tubing. As the gasoline impinges on the tube, thin film, flash evaporation occurs and varying amounts of deposits remain, depending upon the fuels deposition tendencies.
• EXAMPLE 2 The effectiveness of the additive blend is more realistically demonstrated by comparing their effectiveness as a detergent in maintaining valves and carburetor cleanliness in a standard operating V-8 automobile engine modified slightly such that two gasolines may be compared simultaneously.
• Removable aluminum sleeves are placed in the throttle bores of two test carburetors and the weight of deposit accumulated on these sleeves is a measure of fuel additive performance.
• the results of a 24 hr. test are indicated in Table III using low lead gas as described in Table I.
• the results obtained in Table III for the performance test suggests that Additive A is improved by a factor of about 10 percent whileAdditive B is improved by a factor of 20 percent.
• a dual additive comprising the simultaneous reac- Cmpound ptb Fuel Dams Reducm" tion product of a monocarboxylic having 10-20 carbon 28 k k 32 atoms with a mixture of an N-alkyl substituted 15 Ptb A W propylenediamine derivative wherein said alkyl substit- 35 ptb B 50 Low Lead 36 uent is an aliphatic group having 10-20 carbon atoms,
• a gasoline fuel composition comprising from 0.003 to 0.15 percent by weight of a dual additive comwith N-( 3-tridecyloxyp ropyl) propylenediamine such that the molar ratio of the monocarboxylic acid present in the reaction mix toeach of the propylenediamine derivatives is 2:1.

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)
• Solid Fuels And Fuel-Associated Substances (AREA)
• Lubricants (AREA)
• Detergent Compositions (AREA)
• Liquid Carbonaceous Fuels (AREA)

Priority Applications (10)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

Country Status (10)

Cited By (3)

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Citations (5)

• 1974
  • 1974-11-11 US US522709A patent/US3923474A/en not_active Expired - Lifetime
• 1975
  • 1975-07-08 CA CA230,969A patent/CA1047252A/en not_active Expired
  • 1975-07-23 NL NL7508814A patent/NL7508814A/xx not_active Application Discontinuation
  • 1975-10-23 IT IT51902/75A patent/IT1048323B/it active
  • 1975-10-28 NO NO753608A patent/NO141519C/no unknown
  • 1975-10-30 BE BE1006983A patent/BE835025A/xx not_active IP Right Cessation
  • 1975-10-30 FR FR7533207A patent/FR2290489A1/fr active Granted
  • 1975-11-03 DE DE19752549691 patent/DE2549691A1/de not_active Withdrawn
  • 1975-11-10 JP JP13500975A patent/JPS5516196B2/ja not_active Expired
  • 1975-11-11 GB GB46556/75A patent/GB1483866A/en not_active Expired

Patent Citations (5)

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