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
• • 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
  • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring

Definitions

• This invention relates to improved motor fuel. It is more particularly concerned with motor gasoline containing additives that inhibit the formation of deposits in carburetors of gasoline engines.
• Another object of this invention is to provide a stable gasoline composition. Another object is to provide a gasoline adapted to reduce the formation of carburetor deposits. A further object is to effectively reduce carburetor deposits in spark-ignited internal combustion engines. A specific object is to provide a motor gasoline containing small amounts of certain tetrahydropyrimidines.
• this invention provides a motor gasoline containing a small amount, sufiicient to inhibit the formation of carburetor deposits, of a tetrahydropyrimidine resulting from the condensation of naphthenic acid with an 2,961,308 Patented Nov. 22, 1960 ice 2 aliphatic hydrocarbon substituted propylene-diamine having the formula:
• R is an aliphatic hydrocarbon group containing between about 8 carbon atoms and about 18 carbon atoms.
• the addition agents contemplated herein are tetrahydropyrimidines, i.e., condensation products of naphthenic acids with certain aliphatic hydrocarbon-substituted propylene diamines, described hereinafter.
• the naphthenic acids as is well known to those familiar with the art, are monoca-rboxylic acids found in crude petroleum and in petroleum distillates. They are obtained as mixtures rather than as pure compounds.
• Particularly utilizable herein are naphthenic acids containing between about 10 and about 30 carbon atoms.
• Such acids can have an acid number (mg. KOH per gram) varying between about and about 220, corresponding to an average molecular weight of between about 420 and about 275.
• a particularly useful naphthenic acid, acid X has an average molecular formula, C H O an average molecular weight of 297; and acid number of 178; about 5 percent unsaponifiables; and distils, at a pressure of 2 mm. Hg, over the range 315-485 F.
• the diamine reactant used to make the additives contemplated herein is N-aliphatic hydrocarbon substituted propylene diamine having the formula,
• R is an aliphatic hydrocarbon group containing between about 8 carbon atoms and about 18 carbon atoms.
• the diamine reactant can be a pure compound, but, in practice, it will often be a mixture of pure diamines. Several mixtures of diamine reactants are available on a commercial scale.
• Amine A is a mixture of N-substituted propylene diamines of the formula set forth hereinbefore, wherein about 20 percent of the R groups are hexadecyl, about 17 percent are octadecyl, about 26 percent are octadecenyl, and about 37 percent are octadecadienyl.
• Amine B is a similar mixture wherein 8 percent of the R groups are octyl, about 9 percent are decyl, about 47 percent are dodecyl, about 18 percent are tetradecyl, about 8 percent are hexadecyl, about 5 percent are octadecyl, and about 5 percent are octadecenyl.
• amine C about 2 percent of the R groups are tetradecyl, about 24 percent are hexadecyl, about 28 percent are octadecyl, and about 46 percent are octadecenyl.
• Amine C is particularly preferred.
• the tetrahydropyrimidines utilizable herein are condensation products of the naphthenic acid and the propylene diamine reacted in a 1:1 molar ratio.
• water is a by-product of the reaction, provision is made for water removal.
• temperatures of 275 C. can be used for periods of time until evolution of water ceases, usually 4-16 hours.
• Other means of facilitating water removal can be employed, such as, for example, azeotropic distillation and operation under subatmospheric pressure.
• the tetrahydropyrimidines can be represented by the formula:
• the amount of tetrahydropyrimidine added to the motor gasoline will vary between about one pound per thousand barrels (1 lb./M b.) and about 200 lbs/M b., and preferably between about 5 lbs./M b. and about 20 lbs/M b.
• the motor gasoline can, also, contain small amounts of other addition agents, such as, antiknock agents, scavengers, preignition additives, gum inhibitors, and the like.
• R is naphthenyl and R is 2 percent tetradecyl, 24 percent hexadecyl, 28 percent octadecyl, and 46 percent octadecenyl.
• the deposit-forming tendencies of a fuel are determined in the 40-hour engine test. This accelerated test, when run on fuels that contain no detergents, produces an amount of deposit equivalent to the amount observed in 20,000 miles of operation in field tests on taxicab fleets.
• a six-cylinder Chevrolet engine is equipped with notched rings to increase the amount of blowby. The engine is operated for forty hours, using the fuel under test, at alternate idle and running cycles. In the idle cycle, the engine is run at idling speed of 400 r.p.m. with no load, for five minutes. Then, for one minute, the engine is run at a speed of 2500 r.p.m., under a load of 30 B.I-I.P. and at 9.4 in. mercury manifold pressure.
• Gasoline A contained 1.9 cc./gal. lead tetraethyl; 2.5 pounds per thousand barrels gasoline (lbs/M b.) of phenylene diamine (antioxidant); and 0.4 1b./M b. of N,N'-disalicylidene-l,2 propanediamine.
• Gasoline B contained 2.2 cc./gal. lead tetraethyl; 5 lbs./M b. of 2,6-di-t-butyl-4- methyl phenol (antioxidant); one lb./M b. of N,N'-d.isalicylidene-LZ propanediamine; and 43 lbs./M b. of
• cresyl diphenyl phosphate (preignition additive).
• Gasoline C contained 3 cc./gal. lead tetraethyl; one 1b./ M b. of N,N'-disalicylidene-1,2 propanediamine; 10 lbs./ M b. of 2,6-di-t-butyl-4-methyl phenol (antioxidant); 64 lbs/M b. of cresyl diphenyl phosphate; and 25 lbs./M b. of glyceryl monooleate (de-icer).
• EXAMPLE 2 Into portions of each of the aforedescribed gasolines, were blended 50 pounds per thousand barrels of the tetrahydropyrimidine of Example 1. The resultant blends were then subjected to the 40-hour engine test. The gasolines without tetrahydropyrimidine were also tested. Pertinent data and test results are set forth in Table I.
• EXAMPLE 3 A gasoline blend (D) containing 3 cc./gal. lead tetraethyl, one lb./M b. N,N'-disalicy1idene-l,2 propanediamine, and 10 lbs/M b. of 2,6-di-t-butyl-4-methylphenol was run on the 40-hour engine test. The carburetor was inspected and was found to have a rating of 4. Then, lbs./M b. of the tetrahydropyrimidine of Example 1 was added to the gasoline blend (D) and run on the engine test for 70 hours, using the same dirty carburetor that had a rating of 4. At the end of the run, the carburetor had become cleaner and had a rating of 3.
• R is naphthenyl and R is an aliphatic hydrocarbon radical having 8 to 18 carbon atoms.
• R is naphthenyl and R is an aliphatic hydrowherein R is fiaphthenyl and R' is a mixture of aliphatic carbon radical having 8 to 18 carbon atoms. radicals of which about 2 percent are tetradecyl, about 3.

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

Priority Applications (8)

Applications Claiming Priority (1)

Publications (1)

Family

ID=25047903

Family Applications (1)

Country Status (7)

Cited By (8)

Citations (4)

• 0
  • BE BE582037D patent/BE582037A/xx unknown
  • NL NL122198D patent/NL122198C/xx active
  • NL NL242710D patent/NL242710A/xx unknown
• 1958
  • 1958-08-27 US US757457A patent/US2961308A/en not_active Expired - Lifetime
• 1959
  • 1959-08-08 DK DK284859AA patent/DK111787B/da unknown
  • 1959-08-21 DE DES64554A patent/DE1125716B/de active Pending
  • 1959-08-27 GB GB29384/59A patent/GB903032A/en not_active Expired
  • 1959-08-27 FR FR803696A patent/FR1234931A/fr not_active Expired

Patent Citations (4)

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