WO2003042335A2 - Additif pour carburant a faible teneur en soufre - Google Patents

Additif pour carburant a faible teneur en soufre Download PDF

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Publication number
WO2003042335A2
WO2003042335A2 PCT/EP2002/012371 EP0212371W WO03042335A2 WO 2003042335 A2 WO2003042335 A2 WO 2003042335A2 EP 0212371 W EP0212371 W EP 0212371W WO 03042335 A2 WO03042335 A2 WO 03042335A2
Authority
WO
WIPO (PCT)
Prior art keywords
fuel composition
composition according
fuel
formula
additives
Prior art date
Application number
PCT/EP2002/012371
Other languages
German (de)
English (en)
Other versions
WO2003042335A3 (fr
Inventor
Frank Bongardt
Jürgen Röder
Original Assignee
Cognis Deutschland Gmbh & Co. Kg
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cognis Deutschland Gmbh & Co. Kg filed Critical Cognis Deutschland Gmbh & Co. Kg
Priority to EP02795062A priority Critical patent/EP1444312B1/fr
Priority to US10/495,802 priority patent/US20040255510A1/en
Priority to DE50205670T priority patent/DE50205670D1/de
Priority to CA002467394A priority patent/CA2467394A1/fr
Publication of WO2003042335A2 publication Critical patent/WO2003042335A2/fr
Publication of WO2003042335A3 publication Critical patent/WO2003042335A3/fr
Priority to US11/567,610 priority patent/US20070144061A1/en

Links

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, 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
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols

Definitions

  • the present application relates to low-sulfur fuel compositions which contain certain alkoxylated esters as additives,
  • Petroleum-based or petroleum derived products usually contain small amounts of sulfur. Crude oils usually contain between 2 and 0.5% by weight of sulfur.
  • the combustion of such sulfur-containing fuels produces sulfur dioxide as a combustion product, which is oxidized to sulfuric acid in the air and can then cause considerable environmental damage as acid rain.
  • the sulfur not only has adverse effects, but also serves as a lubricant improver in the small amounts in which it is usually present, which is quite desirable in many technical applications, for example as a fuel for internal combustion engines. That is why the use of low-sulfur fuels often leads problems with the friction of the correspondingly fired machine parts.
  • Contain carbon atom are added to adjust the corresponding coefficients of friction.
  • Esters of carboxylic acids with 2 to 50 carbon atoms and polyols are preferably used.
  • the present application therefore relates to fuel compositions containing more than 50% by weight of diesel, gasoline, kerosene or other hydrocarbons which are liquid at room temperature, these fuel compositions being an additive of the formula (I)
  • R represents a mono- or polyunsaturated alkylene radical having 17 carbon atoms and n represents 2 or 3 and k represents a number between 0.5 and 3, in quantities of 0.001 to 0.1% by weight, with the Provided that the fuel composition has a maximum sulfur content of 0.2% by weight.
  • the fuel compositions according to the invention are further characterized in that the sulfur content max. 0.2 wt .-% based on the fuel composition.
  • fuels are understood to mean all energy-supplying supplies whose free combustion energy is converted into mechanical work. This includes all types of engine and aviation fuels, engine fuels, e.g. liquid at room temperature and normal pressure, e.g. for car or truck engines usually contain hydrocarbons, e.g. Petrol or higher-boiling petroleum fractions.
  • Diesel fuels are flame-retardant mixtures of liquid hydrocarbons, which are used as fuels for constant pressure or burner engines (diesel engines) and mainly consist of paraffins with admixtures of olefins, naphthenes and aromatic hydrocarbons. Their composition is inconsistent and depends particularly on the manufacturing method. Diesel is obtained, for example, from gas oil by cracking or from tars obtained from the smoldering of lignite or hard coal. Conventional products have a density between 0.83 and 0.88 g / cm 3 , a boiling point between 170 and 360 ° C and flash points between 70 and 100 ° C. Diesel fuels. Diesel oils for stationary systems and for marine engines have a similar composition as heavy heating oil, which is used for cars, buses and the like. Trucks correspond to the heating oil EL.
  • An essential factor for the usability of diesel is its ignitability, for which the cetane number (CZ) has been introduced.
  • Ignitability refers to the property of an engine fuel to ignite more easily or more difficultly in an engine operating on the diesel principle. For this purpose, every fuel except atomization, pressure and. Temp. A preparation period (ignition delay) until the detectable combustion is required.
  • Quality Ignitability of a fuel means favorable starting behavior u. smooth running of the diesel engine due to short preparation time or small ignition delay; in the event of a large ignition delay, the well-known "nailing" is evident.
  • the requirements for diesel are for slow-running engines CZ 20-40, for small and fast-running CZ> 45.
  • the fuel compositions according to the invention contain diesel, gasoline, kerosene or other hydrocarbons which are liquid at room temperature, for example hexane or pentane. Such fuel compositions which contain diesel as the fuel are particularly preferred. In principle, it is also possible to provide fuel compositions according to the present invention which contain mixtures of, for example, gasoline and kerosene in any proportions.
  • the additives according to formula (I) are known alkoxylated carboxylic acid esters. It is one of the essential knowledge of the present invention that they are unsaturated
  • Carboxylic acids with 11 to 17 carbon atoms in the alkyl chain must act.
  • Ethylene oxide and / or propylene oxide is carried out in a manner known per se.
  • OffenbBrung ⁇ lerW ⁇ -98f25878r describes the ⁇ one-process-to-syntheses-this shortly ethoxylated ' fatty acids by reaction of the fatty acids in the presence of alkanolamines.
  • a special feature of the present additives according to formula (I) is that the number of
  • Alkoxide units per molecule is strictly limited and is preferably 1, i. H. part of the acid and part of the alkoxide have reacted. Since no uniform products are obtained even with the use of modern catalysts, mixtures of different alkoxylated products are regularly used
  • the number k should preferably be in the range from 0.5 to 1.5; those compounds of the formula (I) in which k is 1 are very particularly preferred. Also preferred are compounds of formula (I) in which k is 1 and n is 2.
  • Fuel compositions contain the additives of formula (I), preferably in amounts of 0.001 to 0.01% by weight and preferably 0.001 to 0.005% by weight. Oleic acid esters with 1 part of ethylene oxide are particularly preferred.
  • the additives of the formula (I) according to the invention are particularly preferred in those fuel compositions which have an extremely low sulfur content, ie. H. contain a sulfur content in the range from 0.005 to max. 0.05% by weight. Use in fuel compositions whose sulfur content is below 0.005% by weight is very particularly preferred.
  • the aromatic content of the claimed fuel composition should be less than 25% by volume and preferably less than 20% by volume. Fuel compositions which contain less than 5% by volume of aromatics are very particularly preferred. Fuel compositions which are free of aromatics are particularly preferred.
  • diesel If diesel is selected as the actual fuel, it should have a cetane index of less than 50 and preferably less than 45. The diesel's cetane number should be less than 50.
  • the HFRR value at 60 ° C. preferably being 600 ⁇ m, preferably at most 500 ⁇ m and in particular 400 ⁇ m or less.
  • the HFRR method High Frequency Reciprocating Rig is known to measure the friction of fuels in use. A description of the details can be found in ISO / TC22 / SC7 / WG6 / N188.
  • the use, for example, of fatty alcohols and / or alkoxylated fatty alcohols and / or alkanolamides and / or their derivatives is preferably excluded.
  • Fuel compositions which contain only additives of the formula (I) for reducing irritation are very particularly preferred.
  • the use of the compounds of the formula (I) defined above in fuels, in particular in diesel fuels leads on the one hand to an adequate lubrication behavior of the fuels without the disadvantageous ecological consequences that are customary in the case of fuels containing sulfur being accepted.
  • the fuels additive according to the invention have excellent cold behavior and that no flocculation occurs even at low temperatures.
  • oleic acid ester according to the invention with 1 mole of ethylene oxide per mole of fatty acid was tested in its action for reducing the coefficient of friction (HFRR) of diesel, a commercial glycerol monooleic acid ester (GMO) being used as a comparison.
  • the amount used was 50 ppm of the additive.
  • the non-additive fourth diesel was measured as a reference.
  • the HFRR value of the non-additive fourth diesel was 591 ⁇ m, a value of 529 ⁇ m was measured for the diesel additive fourth with GMO, while the additive according to the invention reached an HFRR value of 500 ⁇ m.

Landscapes

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

Abstract

Compositions de carburant renfermant plus de 50 % en poids de diesel, essence, kérosène ou autres hydrocarbures, liquides à température ambiante, caractérisées en ce qu'elles renferment un additif de formule (I), dans laquelle R désigne un reste alkylène de 17 atomes de C mono- ou polyinsaturé et n est égal à 2 ou 3, et k est un indice compris entre 0,5 et 3, en des quantités de l'ordre de 0,001 à 0,1 % en poids, sous réserve que la composition du carburant ait une teneur en soufre de 0,2 % en poids maximum.
PCT/EP2002/012371 2001-11-15 2002-11-06 Additif pour carburant a faible teneur en soufre WO2003042335A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP02795062A EP1444312B1 (fr) 2001-11-15 2002-11-06 Additif pour carburant a faible teneur en soufre
US10/495,802 US20040255510A1 (en) 2001-11-15 2002-11-06 Additives for low-sulfur fuels
DE50205670T DE50205670D1 (de) 2001-11-15 2002-11-06 Additive für schwefelarme treibstoffe
CA002467394A CA2467394A1 (fr) 2001-11-15 2002-11-06 Additif pour carburant a faible teneur en soufre
US11/567,610 US20070144061A1 (en) 2001-11-15 2006-12-06 Alkoxylated unsaturated carboxylic acid additives for low-sulfur fuels

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10156024A DE10156024A1 (de) 2001-11-15 2001-11-15 Additive für schwefelarme Treibstoffe
DE10156024.9 2001-11-15

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/567,610 Continuation US20070144061A1 (en) 2001-11-15 2006-12-06 Alkoxylated unsaturated carboxylic acid additives for low-sulfur fuels

Publications (2)

Publication Number Publication Date
WO2003042335A2 true WO2003042335A2 (fr) 2003-05-22
WO2003042335A3 WO2003042335A3 (fr) 2003-09-25

Family

ID=7705782

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/012371 WO2003042335A2 (fr) 2001-11-15 2002-11-06 Additif pour carburant a faible teneur en soufre

Country Status (5)

Country Link
US (2) US20040255510A1 (fr)
EP (1) EP1444312B1 (fr)
CA (1) CA2467394A1 (fr)
DE (2) DE10156024A1 (fr)
WO (1) WO2003042335A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105441142B (zh) * 2010-06-21 2017-09-15 周向进 一种清洁高效环保的汽油产品

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0773278A1 (fr) * 1995-11-13 1997-05-14 Ethyl Petroleum Additives Limited Additif pour combustible
EP0826765A1 (fr) * 1996-08-27 1998-03-04 Institut Francais Du Petrole Compositions d'additifs améliorant le pouvoir lubrifiant des carburants et carburants les contenant
FR2772784A1 (fr) * 1997-12-24 1999-06-25 Elf Antar France Additif d'onctuosite pour carburant

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4010606A1 (de) * 1990-04-02 1991-10-10 Henkel Kgaa Verwendung von hydrophobierten hydrotalciten als katalysatoren fuer die ethoxylierung bzw. propoxylierung
DE4034305A1 (de) * 1990-10-29 1992-04-30 Henkel Kgaa Hydrophobierte doppelschichthydroxid-verbindungen, verfahren zur herstellung und ihre verwendung als alkoxylierungskatalysatoren
US5936107A (en) * 1996-12-09 1999-08-10 Henkel Kommanditgesellschaft Auf Aktien Process for the production of fatty acid polyethylene glycol esters
US6074445A (en) * 1997-10-20 2000-06-13 Pure Energy Corporation Polymeric fuel additive and method of making the same, and fuel containing the additive
US6017369A (en) * 1998-11-23 2000-01-25 Pure Energy Corporation Diesel fuel composition
KR100439592B1 (ko) * 1998-11-23 2004-07-12 퓨어 에너지 코포레이션 디젤 연료 조성물
US6222082B1 (en) * 1999-09-08 2001-04-24 Leonard Bloom Diesel fuel for use in diesel engine-powered vehicles
AU2378902A (en) * 2000-11-08 2002-05-21 Aae Technologies Internat Ltd Fuel composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0773278A1 (fr) * 1995-11-13 1997-05-14 Ethyl Petroleum Additives Limited Additif pour combustible
EP0826765A1 (fr) * 1996-08-27 1998-03-04 Institut Francais Du Petrole Compositions d'additifs améliorant le pouvoir lubrifiant des carburants et carburants les contenant
FR2772784A1 (fr) * 1997-12-24 1999-06-25 Elf Antar France Additif d'onctuosite pour carburant

Also Published As

Publication number Publication date
CA2467394A1 (fr) 2003-05-22
EP1444312A2 (fr) 2004-08-11
EP1444312B1 (fr) 2006-01-18
DE10156024A1 (de) 2003-05-28
US20070144061A1 (en) 2007-06-28
DE50205670D1 (de) 2006-04-06
WO2003042335A3 (fr) 2003-09-25
US20040255510A1 (en) 2004-12-23

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