EP0905217A1 - Bleifreies Benzin für Direkteinspritzbenzinmotor - Google Patents

Bleifreies Benzin für Direkteinspritzbenzinmotor Download PDF

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Publication number
EP0905217A1
EP0905217A1 EP98850150A EP98850150A EP0905217A1 EP 0905217 A1 EP0905217 A1 EP 0905217A1 EP 98850150 A EP98850150 A EP 98850150A EP 98850150 A EP98850150 A EP 98850150A EP 0905217 A1 EP0905217 A1 EP 0905217A1
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EP
European Patent Office
Prior art keywords
carbonate
straight
branched
gasoline
oxygen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98850150A
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English (en)
French (fr)
Inventor
Toru c/o Nippon Oil Co. Ltd. Yoshii
Jun Akimoto
Tokuichi Ichikawa
Tatsuo c/o Nippon Oil Co. Ltd. Omata
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eneos Corp
Original Assignee
Nippon Oil Corp
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Filing date
Publication date
Application filed by Nippon Oil Corp filed Critical Nippon Oil Corp
Publication of EP0905217A1 publication Critical patent/EP0905217A1/de
Withdrawn legal-status Critical Current

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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
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Definitions

  • This invention relates to unleaded gasolines for use in direct injection gasoline engines and more particularly to such a gasoline which is capable of reducing the amount of environmental pollutants emission and further excellent in durability of the engine in which the gasoline is employed.
  • a conventional engine forms a homogeneous pre-mixture of gasoline and air by injecting gasoline into the intake port, while a direct injection gasoline engine injects gasoline directly into the combustion chamber like a diesel engine so that it becomes possible to form a stratified fuel mixture which is rich in the neighborhood of the spark plug but ultra highly lean in the entire combustion chamber. Due to the formation of such a stratified fuel mixture, combustion with the highly lean mixture can be achieved, leading to an improvement in fuel consumption equivalent to that of a diesel engine. Moreover, the direct injection of gasoline into the combustion chamber is contributive to the freedom of delay in gasoline vaporization as seen in the conventional engine and enables further enhanced accuracy in control of fuel injection rate.
  • an unleaded gasoline for a direct injection gasoline engine which contains an oxygen-containing compound having 2-15 carbon atoms in an amount in terms of oxygen atom of 0.1-15 mass % based on the total gasoline.
  • the unleaded gasoline for a direct injection gasoline engine according to the invention contains an oxygen-containing compound having 2-15, preferably 2-12, more preferably 2-10 carbon atoms.
  • the oxygen-containing compound has in its molecule at least one oxygen-containing group selected from the group consisting of a hydroxyl group, an ether bond and a carbonyl group.
  • An oxygen-containing compound eligible for the present invention is represented by the formula wherein R 1 and R 3 each are hydrogen or a C 1 - C 15 hydrocarbon group, R 2 is a C 2 - C 4 alkylene group and n is an integer of 0 - 7, provided that the total carbon number in the molecule is from 2 to 15 and if n is 0, it is excluded that both R 1 and R 3 are hydrogen at the same time.
  • Preferred alkyl groups for R 1 and R 3 include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, straight or branched pentyl, straight or branched hexyl, straight or branched heptyl, straight or branched octyl, straight or branched nonyl, straight or branched decyl, straight or branched undecyl, straight or branched dodecyl and straight or branched tridecyl.
  • Preferred examples of an alkenyl group for R 1 and R 3 include vinyl, propenyl, isopropenyl, straight or branched butenyl, butadienyl, straight or branched pentenyl, straight or branched hexenyl, straight or branched heptenyl, straight or branced octenyl, straight or branced nonenyl, straight or branched decenyl, straight or branched undecenyl, straight or branched dodecenyl and straight or branched tridecenyl groups.
  • a cycloalkyl group for R 1 and R 3 include cyclopentyl, cyclohexyl and cycloheptyl groups while preferred examples of an alkylcycloalkyl groups include methylcyclopentyl, dimethylcyclopentyl (inclusive of all positional isomers), ethylcyclopentyl (inclusive of all positional isomers), straight or branched propylcyclopentyl (inclusive of all positional isomers), ethylmethylcyclopentyl (inclusive of all positional isomers), trimethylcyclopentyl(indusive of all positional isomers), diethylcyclopentyl (inclusive of all positional isomers), ethyldimethylcydopentyl (inclusive of all positional isomers), straight or branched propylmethylcyclopentyl (inclusive of positional isomers), straight or branched propylethylcyclopentyl, di
  • Preferred examples of an aryl group for R 1 and R 3 include phenyl and naphtyl groups, while preferred examples of an alkylaryl group include tolyl (inclusive of all positional isomers), xylyl (inclusive of all positional isomers), ethylphenyl (inclusive of all positional isomers), straight or branched propylphenyl (inclusive of all positional isomers), ethyl methyl phenyl (inclusive of all positional isomers), trimethylphenyl (inclusive of all positional isomers), straight or branched butylphenyl (inclusive of all positional isomers), straight or branched propyl methyl phenyl (inclusive of all positional isomers), diethylphenyl (inclusive of all positional isomers), ethyldimethylphenyl (inclusive of all positional isomers), tetramethylphenyl (inclusive of all positional isomers),
  • R 1 and R 3 each independently are preferably hydrogen or a C 1 - C 12 straight or branched alkyl group, more preferably hydrogen or a C 1 - C 6 straight or branched alkyl group and most preferably hydrogen or C 1 - C 4 straight or branched alkyl group.
  • R 2 in formula (I) is a C 2 - C 4 alkylen group such as ethylene, propylene (1-methylethylene, 2-methylethylene), trimethylene, butylene(1-ethylethylene, 2-ethylethylene), 1,2-dimethylethylene, 2,2-dimethylethylene, 1-methyltrimethylene, 2-methyltrimethylene, 3-methylthrimethylene and tetramethylene among which ethylene, propylene and butylene are preferred.
  • Formula (I) wherein either R 1 or R 2 is hydrogen, the other is a hydrocarbon and n is 0 represents a monohydric alcohol. Such an alcohol is exemplified by a monohydric aliphatic alcohol which may be straight or branched.
  • the monohydric aliphatic alcohol examples include ethanol, straight or branched propanol, straight or branched butanol, straight or branched pentanol, straight or branched hexanol, straight or branched heptanol, straight or branched octanol, straight or branched nonanol, straight or branched decanol, straight or branched undecanol, straight or branched dodecanol, straight or branched tridecanol, straight or branched tetradecanol, straight or branched pentadecanol and mixtures thereof.
  • R 1 and R 3 each are hydrogen and n is an integer of more than 1 is a dihydric alcohol.
  • a dihydric alcohol include ethylene glycol, propylene glycol, 1,3-propane diol, 1,2-butane diol (butylene glycol), 1,3-butane diol, 1,4-butane diol, 2-methyl-1,2-propane diol, 2-methyl-1,3-propane diol, 1,2-pentane diol, 1,3-pentane diol, 1,4-pentane diol, 1,5-pentane diol, neopentyl glycol and polymers thereof.
  • Such a terminal-etherified compound exemplarily include ethylene glycol monoalkylether, ethylene glycol dialkylether, propylene glycol monoalkylether, propylene glycol dialkylether, butylene glycol monoalkylether, butylene glycol dialkylether, diethylene glycol monoalkylether, diethylene glycol dialkylether, dipropylene glycol monoalkylether, dipropylene glycol dialkylether, dibutylene glycol monoalkylether and dibutylene glycol dialkylether.
  • polyhydric alcohols having three or more hydroxyl groups can be used as the oxygen-containing compound defined by the present invention.
  • Such alcohols are those having 3 - 10, preferably 3 - 6 hydroxyl groups.
  • Specific examples of the alcohol having 3 - 10 hydroxyl groups are polyhydric alcohols such as glycerol, polyglycerol (dimers through pentamers of glycerol such as diglycerol, triglycerol and tetraglycerol), trimethylolalkane (trimethylolethane, trimethylolpropane and trimethylolbutane) and the dimers and trimers thereof, pentaerythrirol and the dimers and trimers thereof, 1,2,4-butanetriol, 1,3,5-pentanetriol, 1,2,6-hexanetriol, 1,2,3,4-butanetetrol, sorbitol, sorbitan, sorbitol glycerin condensation products, a
  • the oxygen-containing compound having in its molecule a carbonyl group may be exemplified by ketones and esters.
  • ketones can be represented by the formula wherein R 4 and R 5 are each independently a C 1 - C 13 hydrocarbon group, provided that the total carbon number of R 4 and R 5 is from 2 to 14.
  • Preferred hydrocarbon groups for each R 4 and R 5 are a C 1 - C 13 straight or branched alkyl group, a C 2 - C 13 straight or branched alkenyl group, a C 5 - C 13 cycloalkyl or alkylcycloalkyl group, a C 6 - C 13 aryl or alkylaryl group or a C 7 - C 13 arylalkyl group all of which have been exemplified with respect to R 1 and R 3 , R 4 and R 5 each are more preferably a C 1 - C 12 straight or branched alkyl group. Further more preferably, R 4 and R 5 each are a C 1 - C 6 straight or branched alkyl group and most preferably are a C 1 - C 4 alkyl group.
  • ketones represented by formula (II) include dimethylketone (acetone), methylethylketone, diethyl ketone, methyl propyl ketone (inclusive of all isomers of propyl group), ethylpropylketone (inclusive of all isomers of propyl group), dipropyl ketone (inclusive of all isomers of propyl group), methylbutylketone (inclusive of all isomers of butyl group), ethylbutylketone (inclusive of all isomers of butyl group), propylbutylketone (inclusive of all isomers of propyl and butyl groups), dibutylketone (inclusive of all isomers of butyl group), methylpentylketone (inclusive of all isomers of pentyl group), ethylpentylketone (inclusive of all isomers of pentyl group), propylpentylketone
  • a cyclic ketone such as cyclohexane and the like is also eligible for the inventive oxygen-containing compound.
  • an alcohol which may be monohydric or polyhydric and an acid which may be monobasic or polybasic for the ester used as the oxygen-containing compound.
  • Preferred monohydric alcohols may be those having 1 -10 carbon atoms, more preferred are those having 1 - 6 carbon atoms and most preferred are those having 1 - 4 carbon atoms.
  • Specific examples of the monohydric alcohol having 1 -10 carbon atoms are methanol, ethanol, straight or branched propanol, straight or branched butanol, straight or branched pentanol, straight or branched hexanol, straight or branched heptanol, straight or branched octanol, straight or branched nonanol, straight or branched decanol, straight or branched undecanol, straight or branched undecanol, straight or branched dodecanol, straight or branched tridecanol, straight or branched tetradecanol, straight or branched pentadecanol and mixtures thereof.
  • Eligible polybasic acids are dibasic acids having 2 -13 carbon atoms and trimellitic acid. These dibasic acids having 2 -13 carbon atoms may be straight or branched and saturated or unsaturated. Specific examples of such dibasic acids are saturated dibasic acids such as ethanedioic acid (oxalic acid), propanedioic acid (oxalic acid), straight or branched butanedioic acid (inclusive of succinic acid), straight or branched pentanedioic acid, straight or branched hexanedioic acid, straight or branched heptanedioic acid, straight or branched octanedioic acid, straight or branched nonanedioic acid, straight or branched decanedioic acid, straight or branched undecanedioic acid, straight or branched dodecandioic acid and straight or branched tridecanedioic acid
  • the ester obtained may be a full ester derived from the complete esterification of all of the hydroxyl groups contained in the polyhydric alcohol or a partial ester having one or more of hydroxyl groups remaining unesterified.
  • the ester may be a full ester derived from the complete esterification of all of the carboxyl groups in the polybasic acid or a partial ester having one or more of carboxyl groups remaining unesterified.
  • the inventive gasoline is not restricted to octane number, it should have an octane number of greater than 89, preferably greater than 90, more preferably greater than 90.5 and most preferably greater than 91 by the research octane number (RON), and an octane number of greater than 80, preferably greater than 80.5 and most preferably greater than 81 by the motor octane number (MON) so as to maintain good anti-knock performance.
  • RON research octane number
  • MON motor octane number
  • Both RON and MON octane numbers are values measured by the test procedure of JIS K 2280 "Testing Method for Octane Number and Cetane Number".
  • Lower limit temperature (T 70 ) is preferably 100°C.
  • Upper limit temperature (T 70 ) is 130°C, preferably 125°C, more preferably 123°C, most preferably 120°C. Above 130°C would lead to aggravated normal temperature engine performance.
  • the density at 15°C of the inventive gasoline should preferably be in the range of 0.73 to 0.77 g/cm 3 .
  • the lower limit of densities is 0.73 g/cm 3 , preferably 0.735 g/cm 3 . Densities below 0.73 g/cm 3 would result in increased fuel consumption.
  • the upper limit of density is 0.77 g/cm 3 , preferably 0.76 g/cm 3 . Densities above 0.77 g/cm 3 would lead to the possibility of insufficient acceleration and spark plug smoldering.
  • the inventive gasoline is not restricted in terms of the contents of paraffins, olefins and aromatics, such contents should preferably be in the following range: Paraffins (V(P)) 50 - 100 % by volume Olefins (V(O)) 0 -15 % by volume Aromatics (V(Ar)) 0 - 35 % by volume
  • the content of V(P) in the inventive gasoline should be in the range of 50 - 100 % by volume, preferably 60 - 100 % by volume, more preferably 70 - 100 % by volume with a view to precluding gasoline coking in the injector, reducing spark plug smoldering and ozone-formability of the exhaust gas as well as the benzene concentration thereof, with a freedom from soot.
  • V(C 7 + p) is the amount of a saturated aliphatic hydrocarbon having more than 7 carbon atoms, based on the total gasoline.
  • the lower limit of V(C 7 + p) is 10 % by volume, preferably 20 % by volume, while the upper limit of the same is 50 % by volume, preferably 45 % by volume.
  • V(C 7 + p) greater than 10 % by volume leads to an unleaded gasoline excelled in normal temperature engine performance, while V(C 7 + p) less than 50 % by volume leads to an unleaded gasoline excelled in high temperature engine performance.
  • the saturated aliphatic hydrocarbon of more than 7 carbon atoms exemplarily includes n-heptane, 2-methylhexane, 3-methylhexane, 2,2-dimethyl pentane, 2,3-dimethylpentane, 2,4-dimethylpentane, 3,3-dimethylpentane, 3-ethylpentane and 2,2,3-trimethylbutane.
  • V(C 4 ), V(C 5 ), V(C 5 p), V(C 5 o), V(C 6 ), V(C 6 p), V(C 6 o), V(C 7 + p) and V(C 9 + ) are as determined by gas chromatography. Analysis is made with the use of a methyl silicone-made capillary column, a helium or nitrogen carrier gas and an FID detector under a set of condition of 25 to 50 mm in length, 0.5 to 1.5 ml/min in gas flow rate, 1:50 to 1:250 in partition ratio, 150 to 250°C in inlet temperature, -10 to 10°C in initial column temperature, 200 to 250°C in end column temperature and 150 to 250°C in detector temperature.
  • sulfur content of the inventive gasoline which however is less than 50 ppm, preferably less than 30 ppm, more preferably 20 ppm, most preferably less than 10 ppm, based on the total gasoline.
  • This content if larger than 50 ppm would be responsible for poisoning an after treatment catalyst, increases of the concentrations of NOx, Co and Hc and a sharp rise in benzene emission.
  • any suitable known base gasolines such as light naphtha derivable by atmospheric distillation of crude oil, cracked gasoline derivable by catalytic cracking or hydrocracking, reformed gasoline obtainable by catalytic reforming, polymerized gasoline available by olefin polymerization, alkylates derivable addition reaction or alkylation of a hydrocarbon such as isobutane with a lower olefin, isomerized gasoline derivable by converting light naphtha into isoparaffin using an isomerization device, de-n-paraffinized oil, butane, aromatic hydrocarbons and paraffinic fractions derivable by hydrocracking dimerized propylene.
  • base gasolines such as light naphtha derivable by atmospheric distillation of crude oil, cracked gasoline derivable by catalytic cracking or hydrocracking, reformed gasoline obtainable by catalytic reforming, polymerized gasoline available by olefin polymerization, alkylates derivable addition reaction or alkylation of a hydrocarbon
  • Sample gasolines for Inventive and Comparative Examples were prepared by blending the base gasolines in accordance with the blending ratio indicated in Table 2. The composition and properties of each sample gasoline are shown in Table 2.
  • a 2.0-liter displacement, direct injection gasoline engine was operated at a oil-water temperature of 60 °C under the condition equivalent to the constant running at a speed of 40 km/h for 150 hours and thereafeter the dilution of the engine oil by the gasoline was measured.
EP98850150A 1997-09-30 1998-09-29 Bleifreies Benzin für Direkteinspritzbenzinmotor Withdrawn EP0905217A1 (de)

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WO2001007540A2 (en) * 1999-07-21 2001-02-01 Exxon Chemical Patents Inc. Hydrocarbon fuel composition containing an ester
WO2001032809A1 (en) * 1999-11-03 2001-05-10 Exxon Chemical Patents Inc Reduced particulate forming distillate fuels
WO2002034867A1 (de) * 2000-10-24 2002-05-02 Leszek Pilarczyk Bleifreies motorenbenzin der klasse premium/eurosuper
WO2002062923A2 (en) * 2001-02-08 2002-08-15 Bp Corporation North America Inc. Transportation fuels
US6447557B1 (en) 1999-12-21 2002-09-10 Exxonmobil Research And Engineering Company Diesel fuel composition
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EP1341879A2 (de) * 2000-10-24 2003-09-10 ExxonMobil Research and Engineering Company Verfahren zur steuerung der bildung von ablagerungen in benzinmotoren mit direkteinspritzung durch verwendung eines kraftstoffes mit bestimmten zusammensetzungseigenschaften
WO2003078553A3 (en) * 2002-03-12 2004-02-19 Lubrizol Corp Method of operating a direct injection spark-ignited engine with a fuel composition
US6716258B2 (en) 1999-12-21 2004-04-06 Exxonmobil Research And Engineering Company Fuel composition
WO2006052985A1 (en) * 2004-11-08 2006-05-18 The Board Of Regents Of The University Of Texas System Lactones as new oxygenate fuel additives, fuels based thereon and methods for using same
NL1033228C2 (nl) * 2007-01-15 2008-07-16 Univ Eindhoven Tech Vloeibare brandstofsamenstelling alsmede de toepassing daarvan.
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US8231695B2 (en) 2006-08-09 2012-07-31 Afton Chemical Corporation Fuel compositions comprising hydrocarbon oil carriers and methods for using the same
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WO2001005912A1 (en) * 1999-07-16 2001-01-25 Exxonmobil Research And Engineering Company Diesel fuel containing ester to reduce emissions
WO2001007540A3 (en) * 1999-07-21 2001-08-30 Exxon Chemical Patents Inc Hydrocarbon fuel composition containing an ester
WO2001007540A2 (en) * 1999-07-21 2001-02-01 Exxon Chemical Patents Inc. Hydrocarbon fuel composition containing an ester
WO2001032809A1 (en) * 1999-11-03 2001-05-10 Exxon Chemical Patents Inc Reduced particulate forming distillate fuels
US6447557B1 (en) 1999-12-21 2002-09-10 Exxonmobil Research And Engineering Company Diesel fuel composition
US6447558B1 (en) 1999-12-21 2002-09-10 Exxonmobil Research And Engineering Company Diesel fuel composition
US6458176B2 (en) 1999-12-21 2002-10-01 Exxonmobil Research And Engineering Company Diesel fuel composition
US6716258B2 (en) 1999-12-21 2004-04-06 Exxonmobil Research And Engineering Company Fuel composition
WO2002034867A1 (de) * 2000-10-24 2002-05-02 Leszek Pilarczyk Bleifreies motorenbenzin der klasse premium/eurosuper
EP1341879A2 (de) * 2000-10-24 2003-09-10 ExxonMobil Research and Engineering Company Verfahren zur steuerung der bildung von ablagerungen in benzinmotoren mit direkteinspritzung durch verwendung eines kraftstoffes mit bestimmten zusammensetzungseigenschaften
EP1341879A4 (de) * 2000-10-24 2004-10-27 Exxonmobil Res & Eng Co Verfahren zur steuerung der bildung von ablagerungen in benzinmotoren mit direkteinspritzung durch verwendung eines kraftstoffes mit bestimmten zusammensetzungseigenschaften
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WO2002062923A2 (en) * 2001-02-08 2002-08-15 Bp Corporation North America Inc. Transportation fuels
WO2002062923A3 (en) * 2001-02-08 2003-09-12 Bp Corp North America Inc Transportation fuels
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CN110494534A (zh) * 2017-04-11 2019-11-22 巴斯夫欧洲公司 用作燃料添加剂的烷氧基化胺
US11130923B2 (en) 2017-04-11 2021-09-28 Basf Se Alkoxylated amines as fuel additives
CN111556890A (zh) * 2018-01-10 2020-08-18 国际壳牌研究有限公司 减少颗粒排放物的方法
US20200339898A1 (en) * 2018-01-10 2020-10-29 Shell Oil Company A method for reducing particulate emissions
WO2020021070A1 (fr) * 2018-07-27 2020-01-30 Biothink Utilisation d'esters gras volatils particuliers dans des moteurs a essence pour reduire les emissions
FR3084373A1 (fr) * 2018-07-27 2020-01-31 Biothink Utilisation d'esters gras volatils particuliers dans des moteurs a essence pour reduire les emissions
CN112920866A (zh) * 2021-02-07 2021-06-08 深圳蓝诺清洁能源科技有限公司 一种车用汽油复合清净剂及其制备方法
CN112920866B (zh) * 2021-02-07 2024-01-30 深圳蓝诺清洁能源科技有限公司 一种车用汽油复合清净剂及其制备方法

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