WO2007105982A1 - Dérivés de para-éthoxyaniline augmentant la résistance à la détonation de carburants hydrocarbonés et compositions à base de ces dérivés - Google Patents

Dérivés de para-éthoxyaniline augmentant la résistance à la détonation de carburants hydrocarbonés et compositions à base de ces dérivés Download PDF

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WO2007105982A1
WO2007105982A1 PCT/RU2006/000428 RU2006000428W WO2007105982A1 WO 2007105982 A1 WO2007105982 A1 WO 2007105982A1 RU 2006000428 W RU2006000428 W RU 2006000428W WO 2007105982 A1 WO2007105982 A1 WO 2007105982A1
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Prior art keywords
para
ethoxyaniline
methyl
acetyl
phenethidine
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PCT/RU2006/000428
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English (en)
Russian (ru)
Inventor
Yuri Alexandrovich Ivanov
Alexander Yurievich Frolov
Valeriy Vladimirovich Osinin
Vladimir Mixaylovich Perevezentzev
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Obshestvo S Ogranichennoy Otvetstvennjcty 'inoxim'
Limited Liability Company Ifo
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Publication of WO2007105982A1 publication Critical patent/WO2007105982A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • 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
    • 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
    • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
    • 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
    • C10L1/224—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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/10—Use of additives to fuels or fires for particular purposes for improving the octane number

Definitions

  • New compounds N-methyl- or N, N-dimethyl- 5 or N-methyl-N-acetyl-substituted para-ethoxyanilines with high antiknock activity.
  • Para-ethoxyaniline, N-acetyl-para-ethoxyaniline and the new N-methyl- or N, N-dimethyl- or N-methyl-N-acetyl-substituted para-ethoxyanilines are individual or mixtures thereof as components, additives (additives) and / or synergents that effectively increase the resistance of hydrocarbon fuels (fuels) to detonation and fuel compositions based on them.
  • the present invention relates to substances that increase the antiknock resistance of hydrocarbon fuels (fuels) and can be used in the field of oil refining, gas processing to create high-octane fuels.
  • antiknock additives to produce high-octane hydrocarbon combustibles (fuels, gasolines). It is known that to increase the octane number of fuels, both ash and ash-free antiknock additives (additives) are used (used) [1-17.35]. Well-known, but currently little used ash antiknock additives (additives), synergents are organic compounds of manganese, iron, copper, chromium, cobalt, nickel, rare earth elements, lead [1, 4, 5, 17.35], etc., however, all of them are highly toxic, especially organic lead compounds.
  • additives are: low molecular weight aromatic amines [N-methylaniline (MMA), xylidine, toluidine].
  • ADA additive TU 38-401-58-61-93 Another known additive of a similar type is the ADA additive TU 38-401-58-61-93, which additionally contains an antioxidant additive of the ionol type [14].
  • the disadvantages of this type of additives are: their restriction in content due to the increase in oxidation products, tar formation in gasoline during storage and carbon formation during operation in the engine at their increased concentration, and a relatively low increase in octane number in fuels [14, 17].
  • the homologues of benzene are also known as antiknock agents: xylene, ethylbenzene, toluene [14, 16, 17], which increase the octane number of fuels very slightly.
  • hydrocarbon fuels consist of a mixture of various hydrocarbons, which, with a certain combination of components, can acquire the necessary properties in the process of their use (application), namely, as hydrocarbon fuels (fuel) in internal combustion engines, where their optimal operation requires simultaneous achievement of the maximum pressure of the vapor-air mixture at the moment the piston passes the top dead center and decomposition (ignition) of this mixture from the electric spark of the spark plug. If these conditions are not met, detonation occurs, which adversely affects engine operation, fuel consumption and exhaust gas composition [1-7].
  • Aromatic amines can in combination with hydrocarbon fuels (fuels), consisting of a mixture of various hydrocarbons, to form intermolecular bonds with molecules of substances that make up fuels through the formation of complexes, with charge transfer, ⁇ - complexes, ⁇ - complexes, as well as free stable radicals and other active intermediates with resonant energy exchange or new formations [18-32] , which determines the possibility of a synergistic effect.
  • the system can be excited by various and numerous factors at the same time or selectively from only one factor, for example, from an electric discharge, which is very important when certain processes occur under given conditions.
  • ethoxyanilines phenethidines, aminophenetols
  • dyes eg triarylmethane
  • N-cetyl-para-ethoxyaniline N-acetyl-para-phenetidine, phenacetin, acetphenetidine
  • oxygenates can be chosen as prototypes: ethyl or methyl tert-butyl ether, and aniline, xylidine, toluidine, N-methylaniline, N, N-dimethylaniline, which are primary, secondary and tertiary amines.
  • the disadvantages of oxygenates are the need to add them in gasoline in large quantities of 10-25%, to raise the octane number by 3-8 units, the energy of fuels and the negative effect on rubber parts of cars are reduced [14, 16.17].
  • the disadvantages of additives containing aniline and its derivatives are their instability, increased gumming due to which their permissible concentrations are limited to 1-1.3% (mass) and the need for their use in combination with antioxidants.
  • the task of effectively increasing the resistance to detonation of hydrocarbon fuels (fuels) is achieved by using (using) the proposed known para-ethoxyaniline (para-phenethidine, para-aminophenetole) and / or N-acetyl-para-ethoxyaniline (N-acetyl-para-phenethidine, phenacetin ), and / or new N-methyl-N-acetyl-para-ethoxyaniline (N-methyl-N-acetyl-para-phenethidine) synthesized by us, and / or N-methyl-para-ethoxyaniline (N-monomethyl-para -ethoxyaniline, N-methyl-para-phenethidine), and / or N, N-dimethyl-para-ethoxyaniline (N, N ⁇ dimethyl-para-phenethidine), individual il mixtures thereof as components, additives (additives) and / or synergents with or without oxygenates.
  • Figure 3 shows the IR spectrum of N-methyl-para-ethoxyaniline
  • FIG. 4 shows the UV spectrum of N-methyl-para-ethoxyaniline
  • FIG. 5 shows the mass spectrum of N-methyl-para-ethoxyaniline
  • Figure 9 shows the UV spectrum of N 5 N-dimethyl-p-ethoxyaniline
  • Figure 10 shows the mass spectrum of No. 5 N-dimethyl-p-ethoxyaniline
  • Figure 11 shows the IH NMR spectrum of N-methyl-N-acetyl-p-ethoxyaniline
  • Figure 13 shows the IR spectrum of N-methyl-N-acetyl-para-ethoxyaniline
  • Figure 14 shows the UV spectrum of N-methyl-N-acetyl-para-ethoxyaniline
  • Figure 15 shows the Mass spectrum of N-methyl-N-acetyl p-ethoxyaniline
  • N-methyl-N-acetyl-para-ethoxyaniline 22.78 g of N-acetyl-para-ethoxyaniline obtained according to the procedures described in [34.36.37.38] are dissolved in 150 ml of acetone, 20.36 g of finely ground sodium hydroxide are added.
  • the mixture is transferred to a separatory funnel and the target product is extracted twice with 70 ml of toluene.
  • N 5 N-dimethyl-para-ethoxyaniline In a 0.25 L flask equipped with an efficiently operating reflux condenser, a 100 ml mixture is charged. (106.52 g) (0.775 M) of freshly distilled para-ethoxyaniline (paraphenetidine) and 61.82 ml. (140.89 g) (0.993 M) methyl iodide and this reaction mass is heated to boiling and boiled for two hours, while the whole mass hardened.
  • reaction mass is cooled to room temperature and, while cooling, a solution of 48.03 g (1.2 M) sodium hydroxide dissolved in 144.44 ml of distilled water is added in small portions (parts) to it.
  • a solution of 48.03 g (1.2 M) sodium hydroxide dissolved in 144.44 ml of distilled water is added in small portions (parts) to it.
  • Separated N-methyl-para-phenetidine is separated in a separatory funnel, and again boiled in a flask with effective reflux condenser with 61.82 ml (140.89 g) (0.993 M) of methyl iodide until the entire mass has solidified.
  • N, N-dimethyl-paraphenetidine is transferred to a separatory funnel and 280 ml (184.8 g) (2.144 M) of hexane are removed from the mixture by adding it in small portions to the separatory funnel and the mixture is vigorously shaken.
  • Hexane solutions containing N, N-dimethyl-paraphenetidine are separated and combined, and then transferred to a distillation flask.
  • N-monomethyl-para-ethoxyaniline and N, N-dimethyl-para-ethoxyaniline were also obtained using dimethyl sulfate, sodium bicarbonate, sodium hydroxide or potassium according to the procedure described in [Weigand-Hilgetag. Experimental methods in organic chemistry. - Moscow. : Publishing House, “Chemistry” 5 1964. -
  • N and C NMR spectra of a solution of N-methyl-para-ethoxyaniline (4-ethoxy-N-methylaniline) in CDCl 3 were measured on a Bruker spectrometer
  • the IR spectrum was measured in the capillary layer in KBr on a SPECORD M82 spectrophotometer.
  • the spectrum of N-methyl-para-ethoxyaniline (Fig. 3) contains absorption bands with maxima at 450, 518, 647, 705, 751, 946 1116,
  • UV spectra were measured in ethanol solution in 1 cm cuvettes on a SPECORD UV VIS instrument (Carl Zeiss, Jepa).
  • UV spectra of N-methyl-para-ethoxyaniline (Fig. 4) with a characteristic concentration dependence of the intensity of the absorption bands show maxima at 242 and 307 nm and minima at 218 and 275 nm.
  • the mass spectrum was measured on a Finnigan MAT 95 XL mass spectrometer by passing through a capillary column (phase - polydimethylsiloxane containing 5% phenyl groups) at an ionizing electron energy of 70 eV.
  • the IR spectrum was measured in the capillary layer in KBr on a Bruker IFS-113 spectrophotometer.
  • the main characteristic absorption frequencies correspond and confirm this structure of the N 5 N-dimethyl-para-ethoxyaniline molecule.
  • UV spectra were measured in ethanol solution on a SPECORD UV VIS instrument (Carl Zeiss, Jepa). UV spectra of N, N-dimethylpara-ethoxyaniline (Fig. 9) with a characteristic concentration dependence of the intensity of absorption bands show maxima at 247 and 308 nm and minima at 221 and 283 nm.
  • the IR spectrum was measured in the capillary layer in KBr on a Svie Albany Inc. M82 spectrophotometer.
  • the spectrum of N-methyl-N-acetyl-para-ethoxyaniline contains absorption bands with maxima at 808, 924, 976, 1012, 1088.1116, 1144, 1172, 1420 and 1480 cm “1 (low intensity), at 844, 1048, 1300 and 1380 cm “1 (medium intensity), at 1248, 1516 and 1664 cm -1 (high intensity).
  • the latter band is characteristic of amide carbonyl.
  • the characteristic absorption bands of stretching vibrations of the CH bond are manifested at 2900, 2920, and 2980 cm ⁇ v .
  • the main characteristic absorption frequencies correspond and confirm this structure of the N-methyl-N-acetyl-para-ethoxyaniline molecule. Investigations of N-methyl-N-acetyl-para-ethoxyaniline by UV spectrophotometry.
  • UV spectra were measured in ethanol solution in 1 cm cuvettes on a SPECORD UV VIS instrument (Carl Zeiss, Jepa). UV spectra of N-methyl-N-acetyl-para-ethoxyaniline (Fig. 14) with a characteristic concentration dependence of the intensity of the absorption bands show maxima at 228 and 275 nm, a shoulder at 282 nm, and minima at 216 and 263 nm.
  • the effectiveness of the compounds we proposed was determined by the increase in the octane number, determined by the motor method (OCHM) and the research method (OCH) in the reference fuel mixture of isooctane and normal heptane (70:30 volume%, respectively) and on direct race gasolines from OChM 51.5 oil units, gasoline stable gas (BGS) ⁇ 65.5 units. and other commodity gasolines.
  • Example 1 Para-ethoxyaniline, taken 1.3% of the mass, in relation to the reference fuel mixture gave an increase in HF by 5.5 units. (OFM) and 7 units. (OCHI).
  • Example 4 A mixture of N-acetyl-para-ethoxyaniline and butanol in a ratio of 1: 1, respectively, taken 5% of the mass, in relation to the reference fuel mixture gave an increase in HF 3.5 units. (OFM) and 5 units. (OCHI).
  • Example 5 A mixture of N-methyl-para-ethoxyaniline and N, N-dimethyl-para-ethoxyaniline in a ratio of 1: 1, taken 2% of the mass, in relation to the reference fuel mixture gave an increase in HF 6.5 units. (OFM) and 8 units. (OCHI).
  • Example 6. A mixture of Para-ethoxyaniline, N-methyl-para-ethoxyaniline and N, N-dimethyl-para-ethoxyaniline in a ratio of 1: 1: 1, taken 2% of the mass, relative to the reference fuel mixture, gave an increase in HF of 7 units. (OFM) and 9 units. (OCHI).
  • Example 7 A mixture of N-methyl-para-ethoxyaniline and MTBE in a ratio of 1: 1, taken 3% of the mass, in relation to the reference fuel mixture gave an increase of 04 to 8 units. (OFM) and 10.5 units. (OCHI).
  • Example 8 A mixture of N, N-dimethyl-para-ethoxyaniline and isopropyl alcohol in a ratio of 1: 1, respectively, taken 3% of the mass, in relation to the reference fuel mixture gave an increase of 04 to 7.5 units. (OFM) and 9.5 units. (OCHI).
  • Example 9 A mixture of N, N-dimethyl-para-ethoxyaniline and MTBE in a ratio of 1: 1, respectively, taken 3% of the mass, in relation to the reference fuel mixture gave an increase of 04 by 4.5 units. (OFM) and 7 units. (OCHI).
  • Example 10 A mixture of N, N-dimethyl-para-ethoxyaniline and isopropyl alcohol in a ratio of 1: 1, respectively, taken 3% of the mass, in relation to the reference fuel mixture gave an increase of 04 by 4 units. (OFM) and 6.5 units. (OCHI).
  • Example 11 A mixture of para-ethoxyaniline and methyl tert.-butyl ether (MTBE) in a ratio of 1: 1, respectively, taken 3%, relative to the reference fuel mixture, gave a gain of 04 by 7.5 units. (OFM) and 9 units. (OCHI).
  • Example 12 A mixture of para-ethoxyaniline and isopropyl alcohol
  • Example 13 N-methyl-N-acetyl-para-ethoxyaniline, taken 2% of the mass, in relation to the reference fuel mixture gave an increase of 04 1 unit (04M) and 1.5 units. (O4I).
  • Example 14 N-methyl-para-ethoxyaniline, taken 5% of the mass, in relation to the reference fuel mixture gave an increase of 04 to 18 units. (O4M) and 21 units. (04I). Similar results with phenethol, anisole, methyl tert-amyl, methyl-sec-pentyl, ethyl tert-butyl, diisopropyl ethers, methyl, ethyl, butyl alcohols, ether fractions and bottoms were also used, tested and obtained as oxygenates. butyl alcohols and mixtures thereof.

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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)
  • Combustion & Propulsion (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne de nouvelles substances de N-méthyl-para-éthoxyaniline, de N,N-diméthyl-para-éthoxyaniline et de N-méthyl-N-acétyl-para-éthoxyaniline présentant un fort pouvoir antidétonant. Cette invention concerne également la para-éthoxyaniline, la N-acétyl-para-éthoxyaniline et de nouvelles para-éthoxyanilines N-méthyl-substituées, N-acétyl-substituées utilisées seules ou conjointement comme composants, adjuvants (additifs) et/ou agents synergétiques augmentant efficacement la résistance à la détonation de combustibles (carburants) hydrocarbonés, ainsi que des compositions de carburants à base de celles-ci.
PCT/RU2006/000428 2006-03-16 2006-08-14 Dérivés de para-éthoxyaniline augmentant la résistance à la détonation de carburants hydrocarbonés et compositions à base de ces dérivés WO2007105982A1 (fr)

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RU2006108236 2006-03-16
RU2006108236/04A RU2309943C1 (ru) 2006-03-16 2006-03-16 Применение производных пара-этоксианилинов, повышающих стойкость углеводородных топлив к детонации, и топливная композиция (варианты)

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Cited By (4)

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WO2008076759A1 (fr) * 2006-12-14 2008-06-26 Shell Oil Company Composition de carburant et utilisation correspondante
EP2014643A1 (fr) * 2006-04-12 2009-01-14 Obshestvo S Ogranichennoy Otvetstvennostiu Inoxim Dérivés de para-méthoxyanilines augmentant le pouvoir antidétonant de carburants hydrocarbonés et compositions sur leur base
WO2010078030A1 (fr) * 2008-12-30 2010-07-08 Shell Oil Company Composition de combustible et son utilisation
US8715376B2 (en) 2009-04-09 2014-05-06 Shell Oil Company Fuel composition and its use

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RU2471771C1 (ru) * 2011-09-28 2013-01-10 Закрытое Акционерное Общество "Ифохим" Способ селективного получения n-метил-пара-фенетидина
RU2524955C1 (ru) * 2013-04-09 2014-08-10 Закрытое Акционерное Общество "Ифохим" Многофункциональная добавка к углеводородсодержащему топливу и топливная композиция, ее содержащая

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BE893220A (fr) * 1982-05-17 1982-11-17 Marotta Dominico Procede d'enrichissement des combustibles liquides et produit destine a realiser le procede
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2014643A1 (fr) * 2006-04-12 2009-01-14 Obshestvo S Ogranichennoy Otvetstvennostiu Inoxim Dérivés de para-méthoxyanilines augmentant le pouvoir antidétonant de carburants hydrocarbonés et compositions sur leur base
EP2014643A4 (fr) * 2006-04-12 2009-09-09 Obshestvo S Ogranichennoy Otve Dérivés de para-méthoxyanilines augmentant le pouvoir antidétonant de carburants hydrocarbonés et compositions sur leur base
WO2008076759A1 (fr) * 2006-12-14 2008-06-26 Shell Oil Company Composition de carburant et utilisation correspondante
JP2010513605A (ja) * 2006-12-14 2010-04-30 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ 燃料組成物及びその使用
US7976591B2 (en) 2006-12-14 2011-07-12 Shell Oil Company Fuel composition and its use
WO2010078030A1 (fr) * 2008-12-30 2010-07-08 Shell Oil Company Composition de combustible et son utilisation
JP2012514108A (ja) * 2008-12-30 2012-06-21 シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー 燃料組成物およびこの使用
US8715376B2 (en) 2009-04-09 2014-05-06 Shell Oil Company Fuel composition and its use

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