Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
  • C07D239/10—Oxygen or sulfur atoms
• • 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
• • 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
  • C10L1/2227—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond urea; derivatives thereof; urethane

Definitions

• the present invention relates to an improved'motor fuel composition for spark-ignition internal combustion engines, and more particularly to such motor fuel compositions containing an additive which functions to inhibit or to reduce deposits in .the induction system of sparkignition internal combustion engines.
• the critical'accumulation point for these deposits is adjacent to the throttle plate, whose position controls thefuel ratio. As these deposits accumulate, the air flow at idle is restricted with no change in fuel flow, and a rich mixture results causing erratic idling and engine stalling. In order to compensate forthe presence of these deposits, the throttle must be opened slightly by increasing the idle speed adjustment which, although allowing more air flow, automatically supplies more fuel. This requires a fuel correction by changing the idle mixture adjustment screw a compensating amount. The amount of idle adjustment required to. maintaih satisfactory idle performance an indication of the rate of deposit build up. Furthermore; deposits will often form in the idle passageway causing restriction which allows manifold vacuum to draw. more gasoline into the engine, again causing rich idle and engin stalling.
• Still another object of the invention is to provide a motor fuel composition which will remove deposits from the induction system of spark-ignition internal combustion engines.
• a further object of this invention is to provide an additive concentrate, which when added in small amounts to a motor fuel for spark ignition internal combustion engines will inhibit or re
• R is an acyclic aliphatic radical, i.e. an alkyl or alkyleneradical, having from about 8 to about 32 carbon atoms, and is preferably an alkyl group of from about 10 to about 20 carbon atoms derived from a fatty acid or mixed fatty acids, and R ⁇ , R R and R are hydrogen or an alkyl radical of from about 1 to about 4 carbon atoms.
• R R R3 and R are ,alkyl radicals, they can be the same or diiferent alkyl radical.
• Suitable areas are those having the general formula i" RN ⁇ NH Hz lfi CH, wherein R-is as above described, and can be the same or Examples of suitable carbamates are:
• Suitable cyclic ureas are illustrated by the following examples:
• N-stearyl or N-octadecyl propylene urea While combinations of the described carbamates an cyclic ureas in the defined ratios. are efiectiveythey" are not all necessarily equivalent in their effectiveness, since the specific activity of such mixtures may vary to some extent depending upon the severity of conditions during use and other factors. 'In the preparation of the motor fuel compositiomthe carbamate and the urea can be added to the fuelindividually in the defined amounts and proportions, the carbamate and the urea can be pre-admixed in the desired ratio and the mixture added to the fuel, or the mixture ofcarbamate and urea prepared in situ can be added to the fuel. e
• the mixture of carbamate and cyclic urea can be conveniently prepared in situ by reacting molar proportions To a refluxing mixture of 144 g. (0.5 mole) of N-coco- 1,3-propylene diamine and 187 g. of xylene was added 43 g. (0.49 mole) of ethylene carbonate over a 4 /2 hour period.
• the carbamate-urea ratio of the product was 8.2.
• the formation of the cyclic urea (H) a tetrahydropyrimidone is a condensation reaction involving the splitting out from the 3-amino carbamate (1) a molecule of a glycol (HI) corresponding to the starting carbonate ester.
• the secondary reaction forming the cyclic urea is much slower than the initial reaction forming the carbamate, making it facile to vary the reaction conditions so as to obtain the desired carbamate-urea ratio.
• Increasing the reaction time and temperature favor greater urea formation at the expense of "the carbamate yield.
• Product distribution is readily determined by infrared spectroscopy and the reaction can be easily directed thereby.
• the reaction is halted by chilling by suitable means and and isopropylalcohol.
• "'5 ester carburetor is used in m-aking the test-
• a vacuum" port for distributor spark advance is'provided 'iii 'tlie carburetor throat area, and is normally located in the atmospheric pressure area during idling. As deposits build upon the throttle bore, it is necessary to open the throttle valve more to provide the same air flow for the same r.p.m. When this is done; the vacuum port then is partially in the manifold vacuum area. At the start of the test the vacuum on the port is about 2 to 3 inches ofmercury. The failure point of the-test is considered reached when this vacuum increases about 8inches of mercury, i.e. when the port' vacuum reaches to ll inches of mercury.
• the results of the test are expressed in terms of the improvement factor as above defined.
• the base motor fuel employed was a commercial premium gasoline containing the usual additives, i.e. tetraethyl lead, scavengers, antioxidant, metal deactivator, etc.
• gasoline compositions of the present invention were subjected to extensive tests in laboratory engines and in the field.
• laboratorygasolines' containing the -carbamate-urea mix ture of thisinvention passed-the'Chevrol'et induction system deposit; (ISD) test, theCFR L-head surface ignition test and the spark plug fouling test. Further, the de fined mixture demonstrated no deleterious effects on the initial, or storage stability of the base gasoline.
• Gasolines containing the defined carbamate-urea mixture were field tested in a fleet of taxi-cabs over an extended period of time with, periodic inspections of the induction. systems, particularly the carburetors of the test cabs.
• a motor fuel composition comprising a major proportion of a hydrocarbon base fuel distilling within the gasoline distillation range and'from about 0.0005% to about 0.5% of a mixture of 1) a carbamate selected from the group consisting of a hydroxyalkyl 3-(N-alkyl-' amino)- propylcarblamate and a hydroxyalkyl 3'-(-N-al-' kenylamino)-propylcarbamat e having the general formula in which R is an acyclic aliphatic hydrocarbon radical having from about 8 to'about 32 carbon atoms, and R R R R and R are selected from the group consisting, of hydrogen, an alkyl radical of from about 1 to about 4 carbon atoms and mixtures thereof, and (2) a substituted propylene urea having the general formula I CH:
• R is an acylic aliphatic hydrocarbons radical having from about-8 to about 32 carbon atoms, said carbamate and said cyclic urea being present in said mixture in the weight ratio of from about 2:1 to about 1 :2.
• R is an alkyl radical of from about 8 to about 18 carbon atoms derived from mixed fatty acids, and R R R and R are hydrogen.
• a motor fuel composition to spark-ignition internal combustion engines comprising :a major amount of a hydrocarbon base fuel distilling within the gasoline distillation range, a tetra-alkyl lead anti-knock agent and from about 0.0005 to about 0.05% of a mixture of (1) a 2-hydroxyethyl 3-(N-alkylamino)-propylcarbamate having the general formula RNHOHiOHiCHiNHC iOGHQGHmH and (2) a substituted propylene urea having the general formula a a v o l RN ⁇ NH where R is an alkyl group of from about 8 to about 32 carbon atoms, said carbamate and said urea being present in said mixture in the weight ratio of from about 2:1 to about 1:2.
• a motor fuel composition as described in claim 3 in which R is an alkyl group of from 8 to about 18 carbon atoms derived from coconut fatty acids, and in which said carbamate and said urea are present in said mixture in the weight ratio of about "1:1.
• a motor fuel composition as described in claim 3 in herein described can contain in addition thereto 'well which R is an oleyl radical.
• a motor fuel composition for spark-ignition internal combustion engines comprising a major amount of a hydrocarbon base fuel distilling within the gasoline distillation range, a tetraalkyl lead anti-knock agent and from about 0.0005 to about 0.05% of a mixture consisting of (1) a Z-hydroxypropyl S-(N-alkylamine) -propylcarbamate having the general formula RNHCHaCHnCHzNHil O CH( CH!) CHaOH and (2) a substituted propylene urea having the general formula where R is an alkyl group of from about 8 to about 32 carbon atoms, said carbamate and said urea being present in said mixture in the weight ratio of from about 2:1 to about 1:2.
• R is an alkyl group of from 8 to about 18 carbon atoms derived from coconut fatty acids, and in which said carbamate and said urea are present in said mixture in the Weight ratio of about 1:1.
• An additive for use in small amounts in hydrocarbon fuels of the gasoline boiling range adapted for use in spark-ignition internal combustion engines to maintain the induction system of such engines essentially free of deposits said additive consisting essentially of a mixture of (1) a carhamate selected from the group consisting of a hydroxyalkyl 3-(N-alkylamine)-propylcarbamate and a hydroxyalkyl 3-(N-alkenylamino) -propylcarbamate having the general formula R R RNHCH CH OH H o 2 2 rNHCO OH in 1's in which R is an acylic aliphatic hydrocarbon radical having from about 8 to about 32 carbon atoms, and R R R R and R are selected from the group consisting of hydrogen, an alkyl radical of from about 1 to about 4 carbon atoms and mixtures thereof, and (2) a substituted propylene urea having the general formula II RNHCHaCHzCHzNHCOCHaCHaOH formula H113 Ha C a where R is an alky
• R is an alkyl group of from 8 to about 18 carbon atoms derived from coconut fatty acids, and in which said carbamate and said urea are present in said mixture in'the weight ratio of about 1:1.
• An additive for use in small amounts in leaded gasoline for spark-ignition internal combustion engines to maintain the induction system of such engines essentially free of deposits said additive consisting essentially of a mixture of (1) a 2-hydroxypropyl 3- (N-alkyla mino)- propylcarbamate having the general formula II nNnomomomNnooomoHo cmoH and (2) a substituted propylene urea having the general formula 15.
• the method of preparing an additive for use in small amounts in hydrocarbon fuels of the gasoline boiling range adapted for use in spark-ignition internal combustion engines to maintain the induction system of such engines essentially free of deposits comprises reacting molar proportions of a diamine having the general formula RNH(CI-I NH and an alkylene carbonate having the general formula at a temperature of from about 50 C. to about 250 C.
• reaction product consisting essentially of a mixture of a carbamate having the general formula R1 m aumomnmrcob-bon and a cyclic urea having the general formula ll RN NH in which R is an acyclic aliphatic hydrocarbonradical having from about 8 to about 32 carbon atoms,- and R R R and R are selected firom the group consisting of hydrogen, an alkyl radical of from about 1 to about 4 carbon atoms and mixtures thereof, said carbamate and said urea being present in said mixture in the weight ratio of from about 1:2 to about 2: 1.
• R is an alkyl radical of about 8 to about 18 carbon atoms derived from 1 18.
• R is an alkyl group of from about 8'to about 32 carbon atoms, said carbamate and said urea being present in said mixture in the weight ratio of from about 2:1 to about 1:2.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Solid Fuels And Fuel-Associated Substances (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Priority Applications (7)

Applications Claiming Priority (1)

Publications (1)

Family

ID=21842369

Family Applications (1)

Country Status (6)

Cited By (38)

Citations (2)

• 0
  • NL NL120454D patent/NL120454C/xx active
  • BE BE603589D patent/BE603589A/xx unknown
  • NL NL264636D patent/NL264636A/xx unknown
• 1960
  • 1960-05-11 US US28245A patent/US2991162A/en not_active Expired - Lifetime
• 1961
  • 1961-05-10 GB GB17095/61A patent/GB979590A/en not_active Expired
  • 1961-05-10 LU LU40119D patent/LU40119A1/xx unknown
  • 1961-05-10 DE DEST17808A patent/DE1248364B/de active Pending

Patent Citations (2)

Also Published As

Similar Documents