WO2010077161A2 - Additifs optimisateurs de carburant synergiques contenant des amines aromatiques et du manganèse, et essence résultant de leur utilisation - Google Patents

Additifs optimisateurs de carburant synergiques contenant des amines aromatiques et du manganèse, et essence résultant de leur utilisation Download PDF

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Publication number
WO2010077161A2
WO2010077161A2 PCT/RO2009/000015 RO2009000015W WO2010077161A2 WO 2010077161 A2 WO2010077161 A2 WO 2010077161A2 RO 2009000015 W RO2009000015 W RO 2009000015W WO 2010077161 A2 WO2010077161 A2 WO 2010077161A2
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gasoline
octane
manganese
additives
synergistic
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WO2010077161A3 (fr
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Constantin-Marius Vladulescu
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Marine Resources Exploration International BV
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Marine Resources Exploration International BV
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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
    • 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
    • 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
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • 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
    • C10L1/223—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 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
    • C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
    • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
    • 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
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)

Definitions

  • the present invention refers to a process for obtaining octane-booster additives whose compositions comprise at least an aromatic amine, such as N-methylaniline; a manganese compound such as bis-(dicypentadienyl)manganese, methylcyclopentadienyl manganese tricarbonyl or manganese carbonyl, and optionally an oxygenated compound belonging to the class of ethers or alcohols and also to the automotive gasoline obtained from basic gasoline and the above mentioned additives.
  • spark-ignition engines require gasoline having high octane numbers, Research Octane Number (RON) > 95 and Motor Octane Number (MON) > 85.
  • the terms RON and MON are specific to the measurement procedure. Further, in USA and Canada the octane number AKI (average knocking index) representing the mean (RON + M0N)/2 is used.
  • compositions of the gasoline approved for the use in the automotive engines imply drastic restrictions: S ⁇ 10 mg/kg; aromatic hydrocarbons ⁇ 35% vol/vol. (content of benzene: ⁇ 1% vol/vol; olefin ⁇ 18% vol/vol, final boiling point 210 0 C, % vol/vol distillation residue ⁇ 2%, density at 15 0 C: 720-775 kg / m 3 etc., and in the future, in order to reduce noxious emissions, new restrictions on the content of aromatic materials will be imposed. Because of all these restrictions, the oil processing becomes more complicated and new technical problems arise.
  • gasoline having high octane number there are used processing fractions containing isoparaffins, cycloparaffins, and aromatic materials, these classes of hydrocarbons being characterized by high octane numbers.
  • the octane number of gasoline represents its knocking resistance. Due to the influence of the temperature of the flame front, the vapour of the hydrocarbon molecules having long straight chain produce high quantities of reactive hydrocarbon radicals. They react with the oxygen of the ignition air and keep the formation of the OH * and O * radicals. These radicals propagate the knock by generating radical branched chains. The branched molecules and those bond to the aromatic or saturated cycles are more resistant to the effect of the temperature this explaining the high octane numbers.
  • the increase of the octane number of the basic gasoline to a value required by the optimal operation of the spark-ignition engines is carried out by using the octane- booster additives.
  • the oxygenated additives produce a local decrease of the temperature, deactivating the radical branched chains.
  • the additives containing metals react with the OH * and O * radicals splitting the propagation branched chains.
  • the first octane-booster additives used on a large scale were lead tertalkyls which, due to their toxicity, are now prohibited, the lead content in the current gasoline being limited to 5 mg/l.
  • organometallic compounds containing cerium (IV), especially salts with 2,2,6,6-tetramethyl-3,5- heptadione US3794473; US 4036605 or containing alkaline metals: RU2203927; RU2152981 ; US3770397.
  • Octane-booster additives containing organometallics have as a main advantage that, at very low concentrations 10-100 mg metal/L, they increase the octane number of the basic gasoline, thus being the cheapest technical solution.
  • the main drawbacks of using organometallic compounds are correlated to the effect of the formation of the metallic oxides onto the equipments of the engine.
  • the iron oxides have an abrasive effect on the valves of the engine and on the sparking plugs, where, by depositing, they alter the dielectric characteristics.
  • MMT When MMT is used at a concentration of 9-12 mg/L Mn it protects the valves of the engine.
  • Both the iron and manganese oxides alter the operation of the exhaust gas catalytic converter. For this reason the use of manganese with a concentration of maximum 18 mg/L is preferred. For its use at reasonable concentrations, it does not cause negative effects on the noxious gases emissions.
  • ethers of tert-butanol with low aliphatic alcohols are used in large amount as octane-booster additives, the most known being tert-butyl methyl ether (MTBE) and low aliphatic alcohols: Mohammad Ashraf SIi, Halim Hamid, Mohammad Ashraf AIi in "Handbook of MTBE and Other Gasoline Oxygenates" Printed in USA, Marcel Dekker Inc, New York. Basel; 1979; US4468233; US5752992. These additives are generically called oxygenated additives. It is also cited the use of the ethers of the phenols with low alcohols RU2005138060.
  • octane-booster additives industrially used are aromatic amines, especially
  • N-methylaniline GB252019; GB334181A; GB530597; FR1255840; RU2184767; US2819953; US5470358; EP0235280; WO2008076759.
  • the aromatic amines are 4-15 times more efficient than the oxygenated additives, however their drawback is their price and sometimes the high toxicity (aniline and o-toluidine).
  • aminofulvenes US5118325; aminophenols: WO2007105982; WO2007117176; colouring agents and other structures having extended molecular orbitals: WO2006076020; ortho- azidophenol; ortho-azidoaniline: US4280458.
  • aminofulvenes US5118325; aminophenols: WO2007105982; WO2007117176; colouring agents and other structures having extended molecular orbitals: WO2006076020; ortho- azidophenol; ortho-azidoaniline: US4280458.
  • aminofulvenes US5118325
  • aminophenols WO2007105982
  • WO2007117176 colouring agents and other structures having extended molecular orbitals
  • ortho- azidophenol ortho-azidoaniline
  • the present invention provides several multi-compound compositions which combine the characteristics of several octane-booster additives so that by synergistic interactions the maximum effects can be realized.
  • the synergistic effect ⁇ Sx occurs when, in the same gasoline, a series of components A 1 ; A 2 ;... A n , each one with an individual concentration C 1 ; C 2 ;... C n individually induces an increase of the octane number A[X] 1 ; A[X] 2 ;...
  • the patent RU2235117 shows the ferrocene - alcohols (esters) - aromatic amines interactions.
  • the level of Fe is very high (40-62mg/kg), but comparing with the individual activity of the components, it can be estimated that the presence of iron results in an antagonism.
  • the patent RU2110561 reports a detailed study referring to the aromatic amines (NMA, xilidine) - MTBE - additives containing iron ( ⁇ - hidroxy propyl ferrocene; ferrocene) interactions, but the interpretation of the shown data does not allow to establish the nature of the interactions between the components.
  • the patent RU2117691 claims the binary additives Mn (MMT) - xilidine, the manganese concentrations being much above the admitted limits; 45 - 136 mg/kg, and the interactions effects certainly are antagonistic.
  • the patent RU2129141 shows different compositions of an tri-component additive N-methyl aniline - ethanol - additives containing iron (ferrocene and ⁇ - hidroxy-isopropyl ferrocene).
  • the composition of the additive 5-10% wt N-methyl aniline, Fe 150 - 145,5 mg/kg; ethanol about up to 100%, was dosed 5% wt. into a synthetic gasoline 70% isooctane and 30% n-heptane rendering obvious certain synergetic effects which can be deduced by the results extrapolating.
  • organometallic octane - booster additives especially those having high concentrations, alter the different parts of the engine; valves, ignition plugs, catalytic converter and can poluate the environment.
  • the octane - booster additives belonging to the oxygenated compounds class requires high concentrations into the gasoline, usually 5 -16% and, while increasing their concentrations, the the emission of volatile organic compounds and nitric oxides in the exhaust gases increase.
  • the octane - booster additives belonging to the aromatic amines class have the drawback of a high cost, and at high concentrations, they can cause the stylificant increase of the nitric oxides emission in the exhaust gases.
  • the technical problem solved by the present invention is the preparation of the multi-component octane - booster additives having high effiency, based on the synergistic interaction of the organometallic compounds containing manganese, preferably as MMT with aromatic amines or mixtures of aromatic amines and oxygenated compounds, the ratio manganese / amines being in a well defined concentration range.
  • the additive dosing is ground on the author's find that for weight ratios of >0-25 mg Mn/g aromatic amine, significant synergistic and demonstrable effects occur, their maximum intensity occurring in the composition range 0,5 - 1 ,0 mg Mn /g aromatic amine.
  • the gasoline used for experiments was refinery blending type whose characteristics are shown in Table 2
  • the gasoline can be further added with deactivating metals, preferably N,N-disalicylidene-1 ,2-diaminopropane [CAS 94-91-7] and antioxidants belonging to the class of sterically hindered phenols, preferably 2,6-di-tert-butyl-p-cresol [CAS 128-37-0] in order to prevent the gums formation phenomena and the oxidation, processes catalyzed by the metals.
  • deactivating metals preferably N,N-disalicylidene-1 ,2-diaminopropane [CAS 94-91-7] and antioxidants belonging to the class of sterically hindered phenols, preferably 2,6-di-tert-butyl-p-cresol [CAS 128-37-0] in order to prevent the gums formation phenomena and the oxidation, processes catalyzed by the metals.
  • the concentration of the manganese in the gasoline is between 4 and 9 mg/L, thus eliminating the negative effects of the metals presence. Further, 5 examples are shown.
  • Example 1 Into the gasoline having the composition of table 2 with MMT is then added, at different concentrations, N-methyl aniline and finally mixtures of N-methyl aniline and MMT, followed by the measuring of the octane number according to the Standards SR EN ISO 5164:06; SR EN ISO 5183:06. The results of the individually adding of N-methyl aniline and MMT are shown in the tables 3 and 4 ( ⁇ RON; ⁇ MON shows the increase of the octane number after adding the additives).
  • NMA N-methyl aniline
  • MMT MMT
  • the data interpretation renders obvious the existence of the synergistic interactions.
  • the range of synergism is maximum in the ratios range Mn/NMA 0,6 - 1 mg/kg N-methyl aniline. This range is suggestively shown in figure 1 , where the percentage increase of the synergistic additive efficiency % ⁇ E is shown comparing with the individual contribution of NMA and MMT, depending on the ratio Mn/ NMA expressed as mg/kg:
  • the synergistic effect decreases while increasing the concentration of N-methyl aniline.
  • concentration of N-methyl aniline is 1% wt.
  • the synergism area is comprised between >0 and >2,2 mg Mn/g N-methyl aniline, while for a concentration of 2% wt. N-methyl aniline, the synergism area is diminished to the range 0,4 - 1 ,8 mg Mn/g N-methyl aniline, and its intensity is reduced to a half.
  • the preferred range of the synergistic additives compositions is 0,5 - 1 ,0 mg Mn/g N-methyl aniline, range in which the synergistic effect intensity is maximum.
  • Example 2 97g of N-methyl aniline was admixed to homogenization with 3g of N,N- dimethyl aniline, resulting 100g solution containing 97% wt. N-methyl aniline (NMA) and 3% wt. N,N-dimethyl aniline (NNDMA).
  • NMA N-methyl aniline
  • NMDMA N,N-dimethyl aniline
  • 0,52 g MMT was admixed with 9,48g solution 97% wt. aniline and 3% wt. N,N-dimethyl aniline previously prepared, resulting a 13,16 mg/g Mn solution.
  • Example 3 Following the procedure of example 2 the admixtures I - IX having octane - booster properties and representing the comparison standard and the multi-component synergistic additives I-Mn - IX-Mn having the content of Mn within the synergism range of 0,6 - 1 mgMn/g were prepared. For the additives VII-Mn si IX-Mn, the Mn concentrations were calculated so they be within the range 0,6 - 1 mg Mn/g N-methyl aniline. All these compositions are shown in table 7. The additives prepared in this way were dosed up into the basic gasoline having the composition of table 2 and the octane numbers were measured according to the Standards mentioned in example 1 ; the test results are shown in table 8.
  • Example 4 1kg of multi-component synergistic additive was prepared by admixing and homogenizing 929g N-methyl aniline; 29,7g N,N-dimethyl aniline; 29,7g anisole; 3,6 g MMT; 4g N,N-disalicylidene-1 ,2-diaminopropane [CAS 94-91-7]; 4g 2,6-di-tert-butyl-p- cresol [CAS 128-37-0].
  • Example 5 6,5kg of multi-component synergistic additive were prepared by admixing and homogenizing 1891g N-methyl aniline; 58,5g N,N-dimethyl aniline; 450Og anhydrous denaturated ethanol; 3,8 g MMT; 4g N,N-disalicylidene-1 ,2-diaminopropane 4g 2,6-di-tert- butyl-p-cresol.
  • the resulted amount of multi-component synergistic additive was admixed and homogenized with 99kg gasoline having the composition of table 2, resulting 100 kg of gasoline RON 95, whose octane numbers were measured according to the Standards mentioned in example 1 ; the results are shown in table 10.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

La présente invention concerne un additif pour essence qui est un mélange d'amines aromatiques, de préférence de N-méthylaniline, et de composés organométalliques contenant du manganèse, de préférence de méthylcyclopentadiényl-manganèse (II) tricarbonyle, et éventuellement d'un composé organique contenant de l'oxygène tel qu'un éther, un ester ou un alcool.
PCT/RO2009/000015 2008-11-21 2009-11-20 Additifs optimisateurs de carburant synergiques contenant des amines aromatiques et du manganèse, et essence résultant de leur utilisation Ceased WO2010077161A2 (fr)

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ROA200800919 2008-11-21
RO200800919 2008-11-21

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WO2010077161A3 WO2010077161A3 (fr) 2010-09-23

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012023872A3 (fr) * 2010-02-10 2012-04-12 Marine Resources Exploration International B.V. Compositions synergétiques d'additifs antidétonants pour essences
WO2014160802A1 (fr) * 2013-03-27 2014-10-02 Motor Sports Fuel And Equipment Additif pour carburant et composition de carburant

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BE590314A (fr) * 1960-05-02
RU2009176C1 (ru) * 1992-09-18 1994-03-15 Акционерное общество "Сигма-Гикон" Многофункциональная добавка к жидким топливам
CN1218096A (zh) * 1997-11-26 1999-06-02 孙乐之 液体燃料的多功能添加剂
RU2161639C1 (ru) * 2000-07-17 2001-01-10 Закрытое акционерное общество Научно-производственное объединение "Химсинтез" Добавка к бензину и композиция, ее содержащая
RU2260034C1 (ru) * 2004-05-05 2005-09-10 Открытое акционерное общество "Пигмент" Добавка к автомобильному бензину
RU2276683C1 (ru) * 2005-01-25 2006-05-20 Общество с ограниченной ответственностью "РЕССЕЛЛ ГРУП" Добавка к бензину
US8715373B2 (en) * 2007-07-10 2014-05-06 Afton Chemical Corporation Fuel composition comprising a nitrogen-containing compound

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012023872A3 (fr) * 2010-02-10 2012-04-12 Marine Resources Exploration International B.V. Compositions synergétiques d'additifs antidétonants pour essences
WO2014160802A1 (fr) * 2013-03-27 2014-10-02 Motor Sports Fuel And Equipment Additif pour carburant et composition de carburant
US9644162B2 (en) 2013-03-27 2017-05-09 Motor Sports Fuel And Equipment Fuel additive and fuel composition

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