WO2005010130A1 - Low-sulphur diesel fuel and use of fatty acid monoalkyl esters as lubricant improvers for low-sulphur diesel fuels - Google Patents

Low-sulphur diesel fuel and use of fatty acid monoalkyl esters as lubricant improvers for low-sulphur diesel fuels

Info

Publication number
WO2005010130A1
WO2005010130A1 PCT/AT2004/000214 AT2004000214W WO2005010130A1 WO 2005010130 A1 WO2005010130 A1 WO 2005010130A1 AT 2004000214 W AT2004000214 W AT 2004000214W WO 2005010130 A1 WO2005010130 A1 WO 2005010130A1
Authority
WO
Grant status
Application
Patent type
Prior art keywords
acid
fatty
esters
diesel
fuel
Prior art date
Application number
PCT/AT2004/000214
Other languages
German (de)
French (fr)
Inventor
Martin Mittelbach
Michael Koncar
Wilhelm Hammer
Helmut Gössler
Original Assignee
Bdi Anlagenbau Gesellschaft M.B.H.
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

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/19Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/08Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear

Abstract

The invention relates to a low-sulphur diesel fuel containing a maximum of 0.2 wt. % sulphur and fatty acid monoalkyl esters in an amount between 10 and 50,000 ppm as lubricant improver, whereby the fatty acid ester of the fatty acid monoalkyl ester is derived from at least 50 %, in particular at least 70 % of saturated fatty acids. It has been shown that said fatty acid esters exhibit a markedly better lubricant improvement in low-sulphur fuels than biodiesel derived from rapeseed oil or soya oil.

Description

Low sulfur diesel fuel and use of fatty acid monoalkyl esters as lubricity for low-sulfur diesel fuels

The invention relates to a low-sulfur diesel fuel or diesel fuel ff containing max. 0.2 wt .-% of sulfur and fatty acid monoalkyl esters in an amount between 10 and 50,000ppm as lubricity.

Legal provisions compel reduce the content of sulfur compounds in mineral fuels, more and more. Since 1996, the content of sulfur in diesel fuel in Europe with 0.05 wt .-% is limited, but in some countries, such as Sweden, almost exclusively so-called zero-sulfur fuel is used at a level of sulfur less than 10 ppm today , Especially for use in urban areas is already often offered a so-called City-diesel with a sulfur content of 50 ppm.

By removing the sulfur compounds during refining a Nerschlechterung the lubricating properties of the fuel goes along. It was shown that the removal of sulfur compounds is also associated with a reduction of polar oxygenated compounds and polycyclic aromatics, which are responsible for the actual lubricity. but a reduced lubricity can cause serious damage to the injection pumps of diesel engines. For this reason it is necessary to add appropriate additives as lubricity to the diesel fuel. Conventional lubricity or - additive are either synthetic mineral oil products or synthetic esters of different chemical structure. As an environmentally friendly alternative to today many renewable resources such as vegetable oils or vegetable oil derivatives such as Fatty proposed as lubricity additives.

EP 0680506 B describes the use of esters as lubricity.

EP 0635558 Al describes the use of fatty acid monoalkyl esters of saturated and unsaturated fatty acid esters in an amount of 100 to 10,000 ppm. There are mainly methyl ester in the composition of the fatty acids present in vegetable oils, used without further treatment or separation for this use. A similar application is shown in WO 94/17160 of.

WO 96/07632 describes the preparation of agents for improving lubricity by double transesterification of vegetable oils, which are produced in the first stage, fatty acid monoalkyl esters, which are esterified in a second step with a polyol. Similar compounds are described in EP 1088880 Al.

Mixtures of fatty acid esters with dicarboxylic acid esters as lubricity are described in DE 19955354

US 5,891,203 describes the use of a mixture of biodiesel and diethanolamine derivatives as lubricity in low sulfur fuels. In this case, fatty acid amides of diethanolamine and fatty acids are used, especially oleic acid is used as a preferred fatty acid.

In Energy and Fuels (2001, 15, 106-112), the use of biodiesel is produced from various raw materials such as sunflower oil, corn oil, olive oil and used cooking oils, described as an additive for lubricity improvement, with a marked effect could be detected in all products, without differences to determine in individual commodities.

By directive of the European Commission, the proportion of biofuels in the EU should by 2010 increase to a share of 5.75%. In order to achieve this proportion, it will be necessary particularly in the field of biodiesel to fully exploit the potential of possible raw materials. This means that more and more raw materials such as used cooking oils, animal fats or palm oil to be used as sources of raw materials.

A major obstacle to the use of these resources as biofuels is the poor low-temperature behavior of the Fatty acid produced therefrom, whereby the insert is available as biodiesel in 100% form and as a blend component still severely limits. This is where the present invention comes in, which has the goal to provide an improved low-sulfur diesel fuel with max. Wt .-% sulfur to provide 0.2, the fatty acid monoalkyl ester in an amount from 10 to 50,000 ppm as lubricity and in which the above problem is reduced.

The inventive diesel fuel, low-sulfur contains max. 0.2 wt .-% of sulfur and fatty acid monoalkyl esters in an amount between 10 and 50,000ppm as lubricity and is characterized in that the fatty acid radicals of the fatty acid monoalkyl esters derived to at least 50%, especially at least 70% of saturated fatty acids, wherein the fatty acid monoalkyl esters preferably used as fatty acid methyl ester available.

The present invention is based on the surprising discovery that the lubricity of fatty acid monoalkyl esters obviously depends on the content of saturated fatty acid derivatives. It was shown that fatty acid esters having a content of more than 50% of saturated fatty acids a much higher

Lubricity improvement in sulfur diesel fuel show as biodiesel from rapeseed oil or soybean oil.

By fractional crystallization and distillation, the shares can be separated to esters with unsaturated fatty acids. Thus, in particular those fatty acid ester groups are particularly suitable as Schmiermittelverbesserer which are obtained by fractional crystallisation or distillation and are characterized by a high content of saturated fatty acids.

The Fatty acid present in the inventive diesel fuel are preferably made of vegetable fats or oils. As raw materials, all natural vegetable or animal oils and / or fats are suitable, the content of which is already more than 50% saturated fat or equivalent products, which were produced by enrichment or separation of saturated fatty acids from the corresponding oils and fats. Preferably, corresponding fractions from palm oil preparation (palm stearin) or animal fat fractions can be used. Another embodiment of the diesel fuel according to the invention is characterized in that it additionally contains one or more additives to improve cetane number, or for improving the cold behavior.

The invention relates to a further means for improving the lubricity of diesel fuels containing fatty acid monoalkyl esters and is characterized in that the fatty acid radicals of the fatty acid monoalkyl esters derived to at least 50%, especially at least 70%> of saturated fatty acids.

Moreover, the invention relates to a method for producing a Fettsäuremonoalkylesters whose fatty acid residues derived to at least 50%, especially at least 70%) of saturated fatty acids, which is characterized in that a fatty acid monoalkyl esters whose fatty acid residues derived from saturated and unsaturated fatty acids to fractional crystallization or is subjected to distillation.

Finally, the invention relates to the use of fatty acid monoalkyl esters as lubricity improvers for low-sulfur diesel fuels, wherein the fatty acid radicals of the fatty acid monoalkyl esters at least 50%, especially at least 70% of saturated fatty acids derived.

As a measurement method for determining the lubricity wear test was used according to CEC F-06-A-96 in accordance with international standards of the HFRR. The lubricity is determined by the abrasion of a rotating ball. As limit abrasion of 460 microns is considered in this method. The reference fuel used for the tests was a sulfur-free, without additives diesel fuel with an abrasion value of 569 microns.

With use of various biodiesel samples (from animal fat, rapeseed oil, soybean oil and waste cooking oil) has surprisingly been found that, while successive with an addition of 0.5% of all biodiesel samples to an improvement of lubricating properties, but only with the present invention means the limit value was significantly below 460 microns. Only when a use of 1.0%, the biodiesel could fall below samples of rapeseed oil and waste cooking oil the limit, while for biodiesel from soybean oil even an addition of 2.0% has not led to a fall below the limit.

There have been used with high content of saturated fatty acids for the production of fatty acid methyl esters, various palm oil or palm oil fatty acids samples. All samples had a content of more than 50% saturated fat. In all samples, the limit of 460 .mu.m could be undercut at least in an insert of 1.0%>.

According to the European standard EN 590 an additive is permitted with 5.0% for mineral diesel fuel. As with the use of additives, the price of the additive plays a crucial role and the conventional lubricity are very cheap to buy, a use of fatty acid alkyl esters is only economically viable when used as little as possible of the additive.

Thus represent Fatty with a share of over 50% saturated fatty acids are ideal additives for improving the lubricating properties of sulfur-free diesel fuels.

With the following examples preferred embodiments of the invention will be explained in more detail.

example 1

The starting product was animal fat with the following fatty acid composition:

Lauric acid: 0.2%

Myristic: 1.86%

Palmitic: 25.17%

Stearic acid: 14.47%

Oleic acid: 42.98%

Linoleic acid: 9.24% This grease was converted by known methods with methanol and potassium hydroxide into the corresponding fatty acid methyl esters. The fatty acid methyl esters were separated by fractional crystallization at low temperatures in two fractions, one of which fraction was used with a high proportion of saturated fatty acids as a lubricant additive. The fatty acid composition of this fraction was as follows:

Lauric acid: 2.06%, myristic acid: 0.44% palmitic acid: 33.75% stearic acid: 35.00% oleic acid: linoleic acid 21.26%: 2.62%

Were made with additive-free sulfur-free diesel fuel mixtures of this fraction and the lubricity determined by determining the HFRR wear tests according to CEC F-06-A-96th

As a comparison, different biodiesel samples produced from rapeseed oil, soybean oil and used cooking oil also measured with the same test.

HFRR wear values ​​in microns; Refernzwert of additive-free fuel: 569 microns

Example 2 As a raw material for the production of fatty acid methyl esters of a technical fatty acid distillate from Palm oil was used with the following fatty acid composition:

Myristic: 1.59% palmitic acid: 52.07% stearic acid: 3.93% oleic acid: linoleic acid 33.80% 8.37%

This fatty acid mixture was using methanol and conc. reacted sulfuric acid as catalyst to give the corresponding fatty acid methyl esters were obtained.

Were made with additive-free sulfur-free diesel fuel mixtures of these fatty acid methyl esters and lubricity determined by determining the HFRR wear tests according to CEC F-06-A-96th

HFRR wear values ​​in microns; Refernzwert of additive-free fuel: 569 microns

example 3

As raw material for the production of fatty acid methyl esters was palm stearin, which was prepared by fractional crystallization of palm oil, used with the following fatty acid composition:

Myristic acid: 1.3% Palmitic acid: 73.83% Stearic acid: 4.84% oleic acid: linoleic acid 16.56%: 3.52% palm stearin was subjected as a catalyst a multistage transesterification using methanol and potassium hydroxide, the corresponding fatty acid methyl esters were obtained ,

Were made with additive-free sulfur-free diesel fuel mixtures of these fatty acid methyl esters and the lubricity determined by determining the HFRR wear tests according to CEC F-06-A-96th

HFRR wear values ​​in microns; Refernzwert of additive-free fuel: 569 microns

example 4

As raw material for the production of fatty acid methyl esters crude palm oil was used with the following fatty acid composition:

Myristic: 1.07% palmitic acid: 44.23% stearic acid: 4.68% oleic acid: linoleic acid 38.28% 11.74%

This was subjected Plamöl using methanol and potassium hydroxide as a catalyst a multistage transesterification with the corresponding fatty acid methyl esters were obtained.

Were made with additive-free sulfur-free diesel fuel mixtures of these fatty acid methyl esters and lubricity determined by determining the HFRR wear tests according to CEC F-06-A-96th

HFRR wear values ​​in microns; Reference value unadditized fuel: 569 microns

Claims

claims:
1. Low-sulfur diesel fuel containing max. 0.2 wt .-% of sulfur and fatty acid monoalkyl esters in an amount between 10 and 50,000ppm as lubricity,
characterized, in that
the fatty acid radicals of the fatty acid monoalkyl esters at least 50%, especially at least 70% of saturated fatty acids derived.
2. Diesel fuel as claimed in claim 1, characterized in that the fatty acid monoalkyl esters are present as fatty acid methyl ester.
3. Diesel fuel according to any one of claims 1 or 2, characterized in that the fatty acid monoalkyl esters made from vegetable fats and / or oils.
4. Diesel fuel according to one or more of claims 1 to 3, characterized in that it additionally contains one or more additives to improve Cetanzahl- or for improving the cold behavior.
5. A composition for improving the lubricity of diesel fuels containing fatty acid monoalkyl esters, characterized in that the fatty acid radicals of the fatty acid monoalkyl esters derived to at least 50% o, preferably at least 70% o of saturated fatty acids.
6. A method for producing a Fettsäuremonoalkylesters whose fatty acid residues derived to at least 50%, especially at least 70%> of saturated fatty acids, characterized in that a fatty acid monoalkyl esters, the fatty acid residues is subjected to saturated and is derived from unsaturated fatty acids to fractional crystallization or distillation ,
7. Use of fatty acid monoalkyl esters as lubricity improvers for low-sulfur diesel fuels, characterized in that the fatty acid radicals of the fatty acid monoalkyl esters derived to at least 50%, especially at least 70% of saturated fatty acids.
PCT/AT2004/000214 2003-07-28 2004-06-22 Low-sulphur diesel fuel and use of fatty acid monoalkyl esters as lubricant improvers for low-sulphur diesel fuels WO2005010130A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AT11942003 2003-07-28
ATA1194/2003 2003-07-28

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP20040737103 EP1648984A1 (en) 2003-07-28 2004-06-22 Low-sulphur diesel fuel and use of fatty acid monoalkyl esters as lubricant improvers for low-sulphur diesel fuels
CA 2533657 CA2533657A1 (en) 2003-07-28 2004-06-22 Low-sulfur diesel fuel as well as the use of fatty acid monoalkyl esters as lubricity improvers for low-sulfur diesel fuels
CN 200480028129 CN1860209B (en) 2003-07-28 2004-06-22 Low-sulphur diesel fuel and use of fatty acid monoalkyl esters as lubricant improvers for low-sulphur diesel fuels
US11341259 US20060213118A1 (en) 2003-07-28 2006-01-27 Low-sulfur diesel fuel and use of fatty acid monoalkyl esters as lubricant improvers for low-sulfur diesel fuels

Publications (1)

Publication Number Publication Date
WO2005010130A1 true true WO2005010130A1 (en) 2005-02-03

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Country Status (5)

Country Link
US (1) US20060213118A1 (en)
EP (1) EP1648984A1 (en)
CN (1) CN1860209B (en)
CA (1) CA2533657A1 (en)
WO (1) WO2005010130A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1674552A1 (en) * 2004-12-24 2006-06-28 Shell Internationale Research Maatschappij B.V. Fuel compositions
EP1731589A2 (en) * 2005-06-10 2006-12-13 Malaysian Palm Oil Board Palm-based biodiesel formulation
FR2894977A1 (en) * 2005-12-21 2007-06-22 Total France Sa Component improving cetane in diesel fuels and useful to prepare diesel fuels, comprises a stearic acid ester comprised e.g. in (a pure state added with a mixture of) vegetable or animal oil esters in crude or partially hydrogenated form
FR2894978A1 (en) * 2005-12-21 2007-06-22 Total France Sa Component improving cetane in diesel fuels and useful to prepare diesel fuels, comprises a stearic acid ester comprised e.g. in (a pure state added with a mixture of) vegetable or animal oil esters in crude or partially hydrogenated form
EP2175010A1 (en) * 2008-10-10 2010-04-14 Eco Air S.r.l. Use of fatty acid esters as descaling and lubricating agents
US7947241B2 (en) 2007-02-23 2011-05-24 Total Raffinage Marketing Aqueous solution for the treatment of exhaust gases of diesel engines

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102295961B (en) * 2011-07-21 2013-09-04 淄博润博化工销售有限公司 Lubricity additive of low-sulfur diesel oil and preparation method thereof
CN102311838A (en) * 2011-08-08 2012-01-11 华东理工大学 Low-sulfur diesel oil lubrication additive and preparation method and application thereof
CN102977945B (en) * 2012-11-12 2015-07-08 黄河三角洲京博化工研究院有限公司 Diesel oil lubricity improving agent
RU2642080C1 (en) * 2016-08-12 2018-01-24 Федеральное государственное бюджетное образовательное учреждение высшего образования "Вятский государственный университет" Fuel composition

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US4920691A (en) * 1989-05-22 1990-05-01 Fainman Morton Z Fuel additive
WO1994017160A1 (en) * 1993-01-21 1994-08-04 Exxon Chemical Patents Inc. Fuel composition
EP0635558A1 (en) * 1993-07-21 1995-01-25 EURON S.p.A. Gas oil composition
DE10111857A1 (en) * 2001-03-08 2002-09-12 Wolfram Radig Multifunctional additive, for desulfurized mineral diesel fuel, comprises saturated fatty acid esters of lower alcohols and methylated dihydroxybenzenes
WO2002100987A1 (en) * 2001-06-08 2002-12-19 Forchem Oy A process for preparing a fuel additive and the additive
WO2003022960A2 (en) * 2001-09-07 2003-03-20 Shell Internationale Research Maatschappij B.V. Diesel fuel and method of making and using same

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US5891203A (en) * 1998-01-20 1999-04-06 Ethyl Corporation Fuel lubricity from blends of a diethanolamine derivative and biodiesel
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US4920691A (en) * 1989-05-22 1990-05-01 Fainman Morton Z Fuel additive
WO1994017160A1 (en) * 1993-01-21 1994-08-04 Exxon Chemical Patents Inc. Fuel composition
EP0635558A1 (en) * 1993-07-21 1995-01-25 EURON S.p.A. Gas oil composition
DE10111857A1 (en) * 2001-03-08 2002-09-12 Wolfram Radig Multifunctional additive, for desulfurized mineral diesel fuel, comprises saturated fatty acid esters of lower alcohols and methylated dihydroxybenzenes
WO2002100987A1 (en) * 2001-06-08 2002-12-19 Forchem Oy A process for preparing a fuel additive and the additive
WO2003022960A2 (en) * 2001-09-07 2003-03-20 Shell Internationale Research Maatschappij B.V. Diesel fuel and method of making and using same

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1674552A1 (en) * 2004-12-24 2006-06-28 Shell Internationale Research Maatschappij B.V. Fuel compositions
EP1731589A2 (en) * 2005-06-10 2006-12-13 Malaysian Palm Oil Board Palm-based biodiesel formulation
EP1731589A3 (en) * 2005-06-10 2009-09-09 Malaysian Palm Oil Board Palm-based biodiesel formulation
FR2894977A1 (en) * 2005-12-21 2007-06-22 Total France Sa Component improving cetane in diesel fuels and useful to prepare diesel fuels, comprises a stearic acid ester comprised e.g. in (a pure state added with a mixture of) vegetable or animal oil esters in crude or partially hydrogenated form
FR2894978A1 (en) * 2005-12-21 2007-06-22 Total France Sa Component improving cetane in diesel fuels and useful to prepare diesel fuels, comprises a stearic acid ester comprised e.g. in (a pure state added with a mixture of) vegetable or animal oil esters in crude or partially hydrogenated form
WO2007077330A2 (en) * 2005-12-21 2007-07-12 Total France Cetane improver for diesel fuels and diesel fuels containing it
WO2007077330A3 (en) * 2005-12-21 2007-08-23 Total France Cetane improver for diesel fuels and diesel fuels containing it
US8409304B2 (en) 2005-12-21 2013-04-02 Total France Cetane-improving component for diesel fuels and diesel fuels containing it
KR101327934B1 (en) 2005-12-21 2013-11-13 토탈 라피나쥬 마케팅 Cetane improver for diesel fuels and diesel fuels containing it
US7947241B2 (en) 2007-02-23 2011-05-24 Total Raffinage Marketing Aqueous solution for the treatment of exhaust gases of diesel engines
EP2175010A1 (en) * 2008-10-10 2010-04-14 Eco Air S.r.l. Use of fatty acid esters as descaling and lubricating agents

Also Published As

Publication number Publication date Type
CA2533657A1 (en) 2005-02-03 application
US20060213118A1 (en) 2006-09-28 application
CN1860209A (en) 2006-11-08 application
EP1648984A1 (en) 2006-04-26 application
CN1860209B (en) 2010-12-15 grant

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