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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
  • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/56—Ring systems containing three or more rings
  • C07D209/58—[b]- or [c]-condensed
  • C07D209/72—4,7-Endo-alkylene-iso-indoles
  • C07D209/76—4,7-Endo-alkylene-iso-indoles with oxygen atoms in positions 1 and 3
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/06—Phosphorus compounds without P—C bonds
  • C07F9/08—Esters of oxyacids of phosphorus
  • C07F9/09—Esters of phosphoric acids
  • C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
• • 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
• • 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
  • C10L1/26—Organic compounds containing phosphorus
  • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
  • C10L1/2658—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) amine salts

Definitions

• New organic compounds usefulas additives for motorfuels are of the formula wherein the hydrocarbon ring is a cyclohexanic, aromatic, dihydroaromatic or tetrahydroaromatic ring, R R R and R are each a hydrogen atom or an aliphatic, linear or branched, saturated or unsaturated hydrocarbon radical, R to R4 having as a whole from to 30 carbon atoms, R and R being optionally interconnected so as to form a bicyclic compound, the assembly R R com prising 1 to 2 carbon atoms, n is an integer from 2 to 10, m is an integer from 0 to and R is a monovalent aliphatic hydrocarbon radical containing from 1 to 30 carbon atoms.
• This invention relates to new organic compounds, which can be used as additives for motor-fuel compositions.
• the invention has also as particular object the use of these new compounds and their neutralization products as additives having a detergent, anti-frost and anti-corrosion action in motor-fuel compositions, and particularly in those which are used in spark ignited engines.
• a further object of the invention is the use of the new imide compounds in association with mineral oils, as additives for motor-fuel compositions, the latter additive compounds exhibiting in addition to the already mentioned detergent, anti-frost and anti-corrosion properties, good cleaning properties. 7
• gasoline it is intended to mean hydrocarbon motorfuels for spark-ignited engines, having a boiling range essentially between 30 and 200 C.
• hydrocarbon ring may be a cyclohexanic, aromatic, dihydroaromatic or tetrahydroaromatic ring
• R R R and R are selected separately from the group consisting of the hydrogen atom and the linear or branched hydrocarbon radicals, either saturated or not, the number of carbon atoms of R to R taken as a whole, being in the range of from 0 to 30, the radicals R and R being optionally interconnected so as to form a bicyclic compound, the assembly R R then optionally comprising 1 or 2 carbon atoms,'n being an integer having a value from 2 to 10, m being an integer having a value from 0 to 10 and R being a linear or branched aliphatic monovalent hydrocarbon radical, saturated or not, having a number of carbon atoms from 1 to 30.
• the number of carbon atoms of R is lower than 5, the number of recurring units ⁇ (CH NH- ⁇ will be preferably high, for example from 5 to 10.
• R1 R: RI R m 1
• R2- COOH wherein the ring may be aromatic, dihydroaromatic, tetrahydroaromatic or cyclohexanic, the substituents R R R and R being defined as above, R being a linear or branched aliphatic radical containing for example from 1 to 12 carbon atoms or a phenyl radical optionally substituted, and the arrows indicating an isomerism possibility, or
• the condensation of the dicarboxylic compound on the mono-primary amine(s) will be carried out by the reaction of substantially equimolecular amounts of these compounds either in a dry state, or in a solvent.
• a solvent capable of forming an azeotrope with the water produced in the reaction will insure the evolution of the reaction towards the formation of the desired imide.
• solvents which can be used there will particularly be mentioned benzene, toluene and xylenes as well as their mixtures which have the advantage of being a part of the gasoline composition.
• the invention accordingly relates also to the compounds resulting from the neutralization of a compound of the Formula 1, by at least one alkylphosphoric acid, as follows:
• R R R R R, n and m have the same meaning as previously, R is an aliphatic linear or branched hydrocarbon radical, the number of carbon atoms of which may vary preferably from 8 to 18, and p and z are integers so selected that the sum of the -OH groups of the acids is at most equal to the number of amine groups present in the nitrogen compound.
• the mixtures of monoalkyl and dialkyl-phosphoric acids obtained by reacting phosphoric anhydride with'an alcohol or a mixture of aliphatic linear or branched alcohols are particularly advantageous.
• the reaction may be illustrated. as follows:
• the alcohol to be used may be selected for the purpose of obtaining a motor-fuel composition resistant to water extraction.
• the use of branched alcohols such as, for instance, ethylhexyl alcohol is, accordingly, preferred.
• the neutralization reaction of the imide of the Formula 1 may be achieved by the addition of 'alkyl-phosphoric acid(s) to a solution of said imide in an aromatic solvent, and by maintaining the reaction mixture, for about 1 hour, at a mean temperature of from about to 100 C.
• the imides of the'Formula 1, used as such or partially or completely neutralized by alkylphosphoric acids are added to motor-fuel compositions at concentrations of from 10 to 250, and preferably from 10 to 100 parts per million of parts by weight, and this without turbidity being observed in the motor-fuel, even when the addition is made at a low temperature.
• These compounds may be associated with the usual additives without disadvantages.
• the imides of the Formula 1 used in a motor-fuel in association with a minor amount of at least one mineral oil, form moreover, additives having a cleaning action.
• a mineral oil such as for example, a naphthenic oil
• at least One compound of the Formula 1 there is used, for example, from 50 to 2000 p.p.m. by weight of a mineral oil, such as for example, a naphthenic oil and from 10 to 250 p.p.m. by weight of at least One compound of the Formula 1.
• EXAMPLE 1 A mixture of 16.3 g. of N-oleyl propylene diamine (0.05 mole), 7.6 g. of tctrahydro-o.phthalic anhydride (0.05 mole) and 60 ml. of a mixture of toluene and xylene by equal parts by volume, is introduced into a three-neck flask, provided with the device of Dean and Stark and with a thermometer.
• EXAMPLE 2 8.8 g. of an equimolecular mixture of monoand dioctylphosphoric acids, which corresponds to 0.05 hydroxyl equivalent, is added to the solution prepared in Example 1. The addition is carried out in such a manner that the temperature of the mixture is maintained below 65 C. The reaction mixture is then brought to about 80 C. for 1 hour under stirring. There is obtained an oily product which is adjusted to a known volume by means of a mixture of toluene and xylene by equal parts by volume, so as to obtain a titrated solution.
• EXAMPLE 3 A mixture comprising 7.4 g. of o.phthalic anhydride (0.05 mole), 16.3 g. of N-oleyl propylene diamine (0.05 mole) and 60 ml. of a toluene-xylene mixture by equal volumes, is introduced into the device described in Examle 1. p The solution is brought to reflux until there is recovered about 1 ml. of water. The obtained solution is then adjusted to a known volume by means of a mixture of the preceding solvents so as to obtain a titrated solution of N(3-oleylamino propyl) phthalimide.
• EXAMPLE 4 8.8 g. of an equimolecular mixture of mono and dioctyl phosphoric acids, corresponding to 0.05 hydroxyl equivalent is added to the solution prepared in Example 3. The addition is carried out under such conditions that the temperature is kept below 65 C. The reaction mixture is then brought to 80 C. for 1 hour under stirring. There is obtained an oily product, which is adjusted to a known volume by means of a toluene-xylene mixture by equal volumes, so as to obtain a titrated solution.
• EXAMPLE 5 9,088 kg. of xylene, 7.380 kg. of a mixture having as essential components N-oleyl propanediamine and N- stearyl propanediamine (known under trademark Dinoram-S) are introduced into a reactor of 70 liters, provided with a stirring device and a system for azeotropic entrainment.
• N-oleyl propanediamine and N- stearyl propanediamine known under trademark Dinoram-S
• the feed is brought to 35-40 C. so as to dissolve the Dinoram-S mixture in xylene.
• the reaction mixture is brought to reflux and water is removed by azeotropic entrainment.
• the total alkalinity is 0.997 NH equivalent per gram of solution.
• This motor lubricated with a multigrade 20 W/ 40 commercial oil, is fed with a premium gasoline having the following composition by weight:
• the motor is run over 48 hours, while 10 to 12% of the exhaust gases are recycled. At each test the consumption of premium gasoline is about 200 liters.
• the carburetor is disassembled at the end of the test and its merit is evaluated.
• R is hydrogen
• R is 9-octadeceny1-l, decyl-l or eicosyl-l
• m is 1-5
• n is 3.
• R is hydrogen, methyl or propyl
• R is hydrogen
• R is hydrogen or propyl
• R is hydrogen
• R is hexyl-l
• m is 1-8
• n is 3 or 4.
• a compound as defined by claim 1 wherein said hydrocarbon ring is 1,2,3,6-tetrahydrophenylene.
• R is hydrogen, methyl or butenyl
• R is hydrogen
• R is hydrogen
• R is hydrogen or methyl
• R is 9-octadecenyl-1, octadecyl-l, or dodecyl-l
• m is 1 or 2
• n is 3-10.
• Example 6 R1 R2 R1 R; R m n 7 OyeIohexylene.-.
• H H 9 oetadeeenyl-1(oley1) 1 3 a do H Hex -1 2 5 0 do Ethyl.
• Octadecyl 1 (stearyl)- 1 3 10 Phenyl H 9 oetadecenyl-l 1 3 11 d la yl 5 3 12 d 1 3 13 1, 2-dihydrophenylene 8 3 14 do Methyl H..- 1 3 15 do 1 4 16 1, 2, 3,6 tetrahydrophenylene H H 1 0 17 do Methyl H 1 5 is do Butenyl.-.
• H 2 3 19 3,6endomethylene eyelohexylene H H H 9octadecenyl-1- 1 3 20 3,6 endodimethylene eyelohexylene H Methyl.... Methyl H..- Octadecyl-1 1 4 21 3, 6 endomethylene 1, 2,3,6 tetrahydro phenylene.. H.. H H... 9 octadecenyl-l. 1 3 22 do H Methyl...- Methyl. H Oetadecyl-l 1 3 These compounds have been tested in the same manner as in Example 6. The results obtained are similar to those given in this example.
• R R R and R are separately selected from the group consisting of hydrogen and alkyl of 1-12 carbon atoms, the number of carbon atoms of R to R taken as a whole, varying from 0 to 30, the radicals R and R being optionally interconnected so as to form a bicyclic compound, the assembly -R R consisting of 1 to 2 carbon atoms inclusive, n is an integer from 2 to 10, inclusive, m is an integer from 1 to 10 inclusive and R is an alkyl or alkenyl radical having from 1 to 30 carbon atoms inclusive with the provision that the group ⁇ -(CH ),,NH ⁇ R contains at least 16 carbon atoms.
• R is hydrogen, methyl or ethyl, R and R are hydrogen, R is hydrogen or ethyl, R is 9-octadecenyl-1, hexyl-l or octadecyl-l, m is 1 or 2, and n is 3-5.
• R and R are hydrogen, R and R are hydrogen or methyl, R is 9-octadecenyl-l or octadecyl-l, m is l and n is 3 or 4.
• a compound as defined by claim 1 wherein said hydrocarbon ring is 3,6 endomethylene-l,2,3,6 tetrahydrophenylene.
• R and R are hydrogen, ⁇ R, and R are hydrogen or methyl, R is 9-octadecenyl-1 or octadecyl-l, m is 1 and n is 3.
• a compound as defined by claim 1 wherein said compound is N(3 oleyl amino propyl)tetrahydroo.phthalimide.
• a compound as defined by claim 1 wherein said compound is N(3-oleylamino propyl)phthalimide.
• a compound as defined by claim 1 wherein said compound is N-(3-stearyl amino-propyl)phthalimide.
• R R R and R are all hydrogen, R is 9-octadecenyl-1, m is 1, and n is 3.
• R R R and R are all hydrogen, R is hexyl, m is 8 and n is 3.
• R R R and R are all hydrogen, R is 9-octadecenyl-l, m is 1 and n is 10.
• R R R and R are all hydrogen, R is 9-octadecenyl-1, m is 1 and n is 3.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Molecular Biology (AREA)
• Biochemistry (AREA)
• General Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Indole Compounds (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Lubricants (AREA)

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Family Applications (1)

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Cited By (4)

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• 1970
  • 1970-01-21 FR FR7002200A patent/FR2076639A5/fr not_active Expired
• 1971
  • 1971-01-04 BE BE761180A patent/BE761180A/xx not_active IP Right Cessation
  • 1971-01-19 US US00107861A patent/US3804852A/en not_active Expired - Lifetime
  • 1971-01-20 CA CA103,241*7A patent/CA962275A/en not_active Expired
  • 1971-01-20 DE DE19712102559 patent/DE2102559A1/de active Granted
  • 1971-01-21 JP JP195271A patent/JPS5617346B1/ja active Pending
  • 1971-01-21 NL NL7100791A patent/NL7100791A/xx not_active Application Discontinuation
  • 1971-04-19 GB GB2003671A patent/GB1303584A/en not_active Expired

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