WO2005087900A1 - Compositions de combustibles - Google Patents

Compositions de combustibles Download PDF

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Publication number
WO2005087900A1
WO2005087900A1 PCT/EP2005/002210 EP2005002210W WO2005087900A1 WO 2005087900 A1 WO2005087900 A1 WO 2005087900A1 EP 2005002210 W EP2005002210 W EP 2005002210W WO 2005087900 A1 WO2005087900 A1 WO 2005087900A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
vegetable oils
weight
reaction
fuel composition
Prior art date
Application number
PCT/EP2005/002210
Other languages
German (de)
English (en)
Inventor
Jürgen Röder
Original Assignee
Cognis Ip Management Gmbh
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 Ip Management Gmbh filed Critical Cognis Ip Management Gmbh
Priority to EP05715674A priority Critical patent/EP1723218A1/fr
Priority to US10/590,980 priority patent/US20070169407A1/en
Priority to BRPI0508562-4A priority patent/BRPI0508562A/pt
Priority to CA002557251A priority patent/CA2557251A1/fr
Publication of WO2005087900A1 publication Critical patent/WO2005087900A1/fr

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
    • 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
    • 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
    • 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
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • 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
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • 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
    • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
    • 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
    • C10L1/1802—Organic compounds containing oxygen natural products, e.g. waxes, extracts, fatty oils
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

Definitions

  • the present invention relates to fuel / ethanol mixtures which contain reaction products from the reaction of di- or trialkanolamines with vegetable oils as additives. Furthermore, the invention relates to a process for the production of diesel oil / ethanol mixtures and the use of the reaction products as solubilizers for ethanol-containing diesel fuel.
  • additives are used in hydrocarbon-based fuels, such as gas oils, heating oils, gasoline, diesel, kerosene, etc.
  • flow improvers or compounds that improve the emission values of gases such as CO, CO 2 or ⁇ O x are also known .
  • the additives should also be surfactants, which make it possible to increase the homogeneity of diesel fuel mixtures containing alcohols by increasing the solubility of the alcohol, in particular of the frequently used ethanol, in the diesel fuel.
  • a first subject of the present application therefore relates to fuel compositions, free of alkoxylated compounds, containing at least 90% by weight of a hydrocarbon-based fuel, 0.5 to 9% by weight of dry ethanol and 0.1 to 5% by weight.
  • an additive which is a reaction product from the reaction of di- or trialcanolamines with vegetable oils or with alkyl esters of the fatty acid mixtures from vegetable oils.
  • 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 that are liquid at room temperature and normal pressure.
  • Motor fuels e.g. for car or truck engines usually contain hydrocarbons, e.g. Petrol or higher-boiling petroleum fractions.
  • the fuels according to the invention are preferably diesel oil, in particular diesel containing biodiesel.
  • Diesel fuels are obtained from gas oil by cracking or from tars obtained from the smoldering of brown or hard coal. 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. Common products have a density between 0.83 and 0.88 g / cm3, a boiling point between 170 and 360 ° C and flash points between 70 and 100 ° C.
  • the fuels according to the invention preferably contain diesel oil or consist of diesel oil. That includes also the so-called biodiesel, ie a fatty acid methyl ester, preferably rapeseed oil fatty acid methyl ester, which is preferably contained in the diesel according to the invention.
  • the dry ethanol is either commercially available "absolute ethanol" with a defined water content, which can vary depending on the commercial product, or ethanol, which is dried using well-known drying agents such as sodium, preferably to a water content of less than 0, 5% by volume of water Drying over a molecular sieve can be connected if necessary.
  • the fuels according to the invention are notable for the fact that they contain, as additives, only the reaction product from the reaction of di- or trialkanolamines with vegetable oils or with alkyl esters of the fatty acid mixtures from vegetable oils, and that therefore no expensive and complex mixtures of different individual substances are necessary. It is a very cost-effective product, since the reaction product does not have to be subjected to any further workup in addition to filtration, which means that costly and time-consuming workup steps are eliminated.
  • the main reaction products from the reaction of di- or trialkanolamines with vegetable oils or with alkyl esters of the fatty acid mixtures from vegetable oils are alkanolamides of the fatty acids contained in the oils.
  • these alkanolamides are from unreacted raw materials such as alkanolamines, partially converted raw materials such as, for example, di- or monoglycerides, to separate further reaction products such as glycerol or ethanol or methanol, but only filtration to remove insoluble constituents is necessary, these are very inexpensive reaction products.
  • ⁇ Effindung are ⁇ sö che Tres töTfzusammen appen containing additives are the reaction products of di- or trialkanolamines with vegetable oils in which the vegetable oils contain fatty acid ester, the mono- or poly-unsaturated alkyl radicals having 11 to 21 C- Contain atoms.
  • fatty acid esters with monounsaturated alkyl radicals with 17 C atoms are particularly preferred.
  • Unsaturated representatives are, for example, laurolein, myristolein, palmitolein, petroselaidin, oil, elaidin, ricinol, linole, linolaidin, linolenadadolein, arachidone and erucic acid. Mixtures of the methyl esters of these acids are also suitable. The use of fatty acid esters which contain fatty acids from the group methyl oleate, methyl palmitate, methyl stearate and / or methyl pelargonate is particularly preferred.
  • the fuel composition according to the invention preferably contain additives which are reaction products of di- or trialkanolamines with vegetable oils, in which the vegetable oils are selected from the group formed by soybean oil, rapeseed oil, sunflower oil, peanut oil, linseed oil, olive oil, castor oil, palm oil and safflower oil.
  • the vegetable oils are selected from the group formed by soybean oil, rapeseed oil, sunflower oil, peanut oil, linseed oil, olive oil, castor oil, palm oil and safflower oil.
  • particularly preferred is the conversion of soybean oil, sunflower oil or rapeseed oil and in particular the conversion of soybean oil.
  • the vegetable oils are essentially triglyceride mixtures, with the glycerin being completely esterified with longer-chain fatty acids.
  • Peanut oil contains on average (based on fatty acid) 54% by weight of oleic acid, 24% by weight of linoleic acid, 1% by weight of linolenic acid, 1% by weight of arachidic acid, 10% by weight of palmitic acid, and 4% by weight of stearic acid.
  • the melting point is 2 to 3 ° C.
  • Linseed oil typically contains 5% by weight of palmitic acid, 4% by weight of stearic acid, 22% by weight of oleic acid, 17% by weight of linoleic acid and 52% by weight of linolenic acid.
  • the iodine number is in the range from 155 to 205, the saponification number is 188 to 196 and the melting point is around - 20 ° C.
  • Olive oil mainly contains oleic acid. Palm oil contains about 2% by weight myristic, 42% by weight palmitic, 5% by weight stearic, 41% by weight oleic, 10% by weight linoleic acid as fatty acid components.
  • Rapeseed oil typically contains about 48% by weight erucic acid, 15% by weight oleic acid, 14% by weight linoleic acid, 8% by weight linolenic acid, 5% by weight iconic acid, 3% by weight palmitic acid7 " 2 G as fatty acid components ⁇ ew: -% ⁇ He - ece äure ⁇ ffii ⁇ T Gew " .-% ⁇ Docosaiäien yarn. RäpsöL from new breeding is enriched with regard to the unsaturated components.
  • Typical fatty acid fractions here are erucic acid 0.5% by weight, oleic acid 63% by weight, linoleic acid 20% by weight, linolenic acid 9% by weight, icosenic acid 1% by weight, palmitic acid 4% by weight, hexadecenoic acid 2 % By weight and docosadienoic acid 1% by weight.
  • Castor oil consists of 80 to 85% by weight of the glyceride of ricinoleic acid, in addition about 7% by weight of glycerides is oil, 3% by weight of glycerides is linoleic and about 2% by weight of glycerides the palmitic and stearic acid contain.
  • Soybean oil contains 55 to 65% by weight of the total fatty acids of polyunsaturated acids, especially linoleic and linolenic acid.
  • the situation is similar with sunflower oil, whose typical fatty acid spectrum, based on total fatty acid, looks as follows: approx. 1% by weight Myristic, 3 to 10% by weight palmitic, 14 to 65% by weight oleic and 20 to 75% by weight linoleic acid.
  • the additives are reaction products from the reaction of di- or trialkanolamines with alkyl esters of the fatty acid mixtures from the vegetable oils mentioned and in particular the preferred vegetable oils.
  • the alkyl esters of the fatty acid mixtures are methyl esters and / or ethyl esters.
  • the fatty acid composition in the mixture results from the respective native fatty acid composition of the vegetable oil used and the respective quality of the raw material from which the methyl and / or ethyl esters are produced in a known manner.
  • the di- or trialkanolamines to be reacted and leading to the desired reaction product are alkanolamines with alkanol residues of 1 to 4 carbon atoms, preferably ethanolamines.
  • the di- or trialkanolamines can have alkanol residues of the same or different number of carbon atoms, but the reaction with amines which have two or three of the same alkanol residues is preferred, the reaction of diethanolamine or triethanolamine being particularly preferred.
  • Alkyl esters of the fatty acid mixtures from vegetable oils are preferably characterized in that the reaction is carried out until the reaction product is clear and the product clearly dissolves in diesel at -10 to -20 ° C. in a 1% mixture. In addition to filtration, no further processing steps are necessary.
  • those fuel compositions are preferred in which the volume ratio (v / v) of diesel oil to additive is in the range from 1000: 0.5 to 1000: 50, and preferably from 1000: 1 to 1000: 50.
  • a preferred embodiment claims a fuel composition consisting of 90 to 98% by weight of diesel oil, 1 to 8% by weight of dry ethanol and 0.1 to 1.5% by weight, preferably 0.5 to 1.0% by weight an additive from the reaction product from the reaction of di- or trialkanolamines with vegetable oils or with alkyl esters of the fatty acid mixtures from vegetable oils.
  • Another object of the invention relates to a method for producing diesel oil / ethanol mixtures, wherein either diesel oil and dry ethanol are mixed and then an additive which is a reaction product from the reaction of di- or trialkanolamines with vegetable oils or with Alkyl esters of the fatty acid mixtures from vegetable oils are added in amounts of at most 0.5 to 5.0% by weight, or first the additive, which is a reaction product from the reaction of di- or trialkanolamines with vegetable oils or with alkyl esters of the fatty acid mixtures deals from vegetable oils, mixed in amounts of maximum 0.1 to 5.0 wt .-% in dry ethanol and then added to the diesel.
  • the use of the additives according to the invention makes it possible to produce inexpensive mixtures of fuels with dry ethanol, preferably diesel oil with dry ethanol. Max. 0.5 to 1.5% by weight of additive was added to the diesel oil / ethanol mixture.
  • the entire fuel composition is preferably dry, i.e. the water content of the entire fuel composition should be less than 0.2% by volume, preferably less than 0.1% by volume.
  • the additized fuel was gradually cooled to -30 ° C in a mixture of 94% Diesel LS, 5% ethanol and 1% reaction product, taking a sample at a temperature distance of 1 ° C and taking it under a vacuum of 2 kPa a standardized filter device was sucked.
  • the specified temperature value then corresponds to the temperature at which the fuel can no longer flow through the filter device in a defined time.
  • DEA diethanolamine
  • TE triethanolamine
  • SZ acid number
  • VZ saponification number
  • AZ amine number

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne des compositions de combustibles exemptes de composés alcoxylés et contenant au moins 90 % en poids d'un combustible à base d'hydrocarbure ; 0,5 à 9 % en poids d'éthanol sec et 0,1 à 5 % en poids d'un additif qui est un produit de conversion issu de la réaction de dialkanolamines ou de trialkanolamines avec des huiles végétales ou des esters d'alkyle des mélanges d'acide gras des huiles végétales.
PCT/EP2005/002210 2004-03-11 2005-03-03 Compositions de combustibles WO2005087900A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP05715674A EP1723218A1 (fr) 2004-03-11 2005-03-03 Compositions de combustibles
US10/590,980 US20070169407A1 (en) 2004-03-11 2005-03-03 Fuel compositions
BRPI0508562-4A BRPI0508562A (pt) 2004-03-11 2005-03-03 composições propelentes
CA002557251A CA2557251A1 (fr) 2004-03-11 2005-03-03 Compositions de combustibles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004011821A DE102004011821A1 (de) 2004-03-11 2004-03-11 Treibstoffzusammensetzungen
DE102004011821.3 2004-03-11

Publications (1)

Publication Number Publication Date
WO2005087900A1 true WO2005087900A1 (fr) 2005-09-22

Family

ID=34895190

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2005/002210 WO2005087900A1 (fr) 2004-03-11 2005-03-03 Compositions de combustibles

Country Status (7)

Country Link
US (1) US20070169407A1 (fr)
EP (1) EP1723218A1 (fr)
CN (1) CN1930273A (fr)
BR (1) BRPI0508562A (fr)
CA (1) CA2557251A1 (fr)
DE (1) DE102004011821A1 (fr)
WO (1) WO2005087900A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007003344B3 (de) * 2006-12-15 2008-07-10 Helmut KÖRBER Dieselkraftstoffgemisch
AU2009279894A1 (en) * 2008-08-05 2010-02-11 Spirit Of The 21St Century Group,Llc Modified fuels and methods of making and using thereof
CN103031165B (zh) * 2012-12-12 2015-01-07 深圳英迪创新科技有限公司 一种燃料添加剂及其制备方法和应用
CN106010679A (zh) * 2016-06-19 2016-10-12 张育栋 一种高热值醇基燃料油及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2336119A (en) * 1998-04-09 1999-10-13 Coval Technologies Limited Solubilising water and petrol
US20020178650A1 (en) * 2001-05-03 2002-12-05 Michio Ikura Low temperature stable diesel oil/alcohol mixtures
US6589302B1 (en) * 2000-05-09 2003-07-08 Texaco Inc. Friction modifier for poor lubricity fuels
US20040040202A1 (en) * 2000-11-08 2004-03-04 Aae Technologies International Plc Alkoxylate and alcohol free fuel additives

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2336119A (en) * 1998-04-09 1999-10-13 Coval Technologies Limited Solubilising water and petrol
US6589302B1 (en) * 2000-05-09 2003-07-08 Texaco Inc. Friction modifier for poor lubricity fuels
US20040040202A1 (en) * 2000-11-08 2004-03-04 Aae Technologies International Plc Alkoxylate and alcohol free fuel additives
US20020178650A1 (en) * 2001-05-03 2002-12-05 Michio Ikura Low temperature stable diesel oil/alcohol mixtures

Also Published As

Publication number Publication date
CN1930273A (zh) 2007-03-14
EP1723218A1 (fr) 2006-11-22
CA2557251A1 (fr) 2005-09-22
US20070169407A1 (en) 2007-07-26
DE102004011821A1 (de) 2005-09-29
BRPI0508562A (pt) 2007-08-14

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