WO2005010130A1 - Schwefelarmer dieseltreibstoff sowie verwendung von fettsäuremonoalkylestern als schmierfähigkeitsverbesserer für schwefelarme dieseltreibstoffe - Google Patents

Schwefelarmer dieseltreibstoff sowie verwendung von fettsäuremonoalkylestern als schmierfähigkeitsverbesserer für schwefelarme dieseltreibstoffe Download PDF

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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
WIPO (PCT)
Prior art keywords
fatty acid
acid monoalkyl
low
monoalkyl esters
esters
Prior art date
Application number
PCT/AT2004/000214
Other languages
German (de)
English (en)
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
Application filed by Bdi Anlagenbau Gesellschaft M.B.H. filed Critical Bdi Anlagenbau Gesellschaft M.B.H.
Priority to EP04737103A priority Critical patent/EP1648984A1/de
Priority to NZ545545A priority patent/NZ545545A/en
Priority to CA002533657A priority patent/CA2533657A1/en
Priority to AU2004259773A priority patent/AU2004259773B2/en
Priority to CN2004800281298A priority patent/CN1860209B/zh
Publication of WO2005010130A1 publication Critical patent/WO2005010130A1/de
Priority to US11/341,259 priority patent/US20060213118A1/en
Priority to HK07102628.9A priority patent/HK1097567A1/xx

Links

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
    • 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
    • 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

Definitions

  • the invention relates to a low-sulfur diesel fuel or diesel fuel containing max. 0.2% by weight of sulfur and fatty acid monoalkyl esters in an amount between 10 and 50,000 ppm as lubricity improvers.
  • EP 0 680 506 B describes the use of esters as lubricity improvers.
  • EP 0 635 558 AI describes the use of fatty acid monoalkyl esters from saturated and unsaturated fatty acid esters in an amount of 100 to 10,000 ppm.
  • methyl esters in the composition in which the fatty acids are present in vegetable oils are used for this application without further pretreatment or separation.
  • a similar application can be found in WO 94/17160.
  • WO 96/07632 describes the preparation of agents for improving the lubricity by double transesterification of vegetable oils, fatty acid monoalkyl esters being produced in the first stage, which are transesterified with a polyol in a second stage. Similar compounds are described in EP 1 088 880 AI.
  • No. 5,891,203 describes the use of a mixture of biodiesel and diethanolamine derivatives as lubricity improvers in low-sulfur fuels.
  • Fatty acid amides from diethanolamine and fatty acids are used, with oleic acid being the preferred fatty acid.
  • biodiesel made from various raw materials such as sunflower oil, corn oil, olive oil and used cooking oils, is described as an additive to improve lubricity, whereby a clear effect could be found for all products, without being able to determine differences in the individual raw materials.
  • the low-sulfur diesel fuel according to the invention contains max. 0.2% by weight of sulfur and fatty acid monoalkyl esters in an amount between 10 and 50,000 ppm as lubricity improver and is characterized in that the fatty acid residues of the fatty acid monoalkyl esters derive at least 50%, in particular at least 70%, from saturated fatty acids, the fatty acid monoalkyl esters preferably as fatty acid methyl esters available.
  • the present invention is based on the surprising finding that the lubricity of fatty acid monoalkyl esters obviously depends on the content of saturated fatty acid derivatives. It has been shown that fatty acid esters with a content of more than 50% of saturated fatty acids are much higher
  • Lubricity improvements in low-sulfur diesel fuel show as biodiesel from rapeseed oil or soybean oil.
  • esters with unsaturated fatty acids can be separated off by fractional crystallization and distillation.
  • those fatty acid ester fractions which are obtained by fractional crystallization or distillation and which are characterized by a high content of saturated fatty acids, are particularly suitable as lubricant improvers.
  • the fatty acid monoalkyl esters contained in the diesel fuel according to the invention are preferably made from vegetable fats and or oils. All natural vegetable or animal oils and / or fats whose content of saturated fatty acids is already over 50% or corresponding products which have been produced by enriching or separating the saturated fatty acids from the corresponding oils and fats are suitable as raw materials. Corresponding fractions from palm oil processing (palm stearin) or animal fat fractions are preferably used. Another embodiment of the diesel fuel according to the invention is characterized in that it additionally contains one or more additives for improving the cetane number or for improving the low-temperature behavior.
  • the invention further relates to an agent for improving the lubricity of diesel fuels containing fatty acid monoalkyl esters and is characterized in that at least 50%, in particular at least 70%, of the fatty acid residues of the fatty acid monoalkyl esters come from saturated fatty acids.
  • the invention relates to a process for the preparation of a fatty acid monoalkyl ester, the fatty acid residues of which at least 50%, in particular at least 70%) are derived from saturated fatty acids, which is characterized in that a fatty acid monoalkyl ester, the fatty acid residues of which are derived from saturated and from unsaturated fatty acids, is subjected to fractional crystallization or subjected to distillation.
  • the invention relates to the use of fatty acid monoalkyl esters as lubricity improvers for low-sulfur diesel fuels, the fatty acid residues of the fatty acid monoalkyl esters deriving at least 50%, in particular at least 70%, from saturated fatty acids.
  • the HFRR wear test in accordance with CEC F-06-A-96 was used as the measuring method for determining the lubricity in accordance with international standards.
  • the lubricity is determined based on the abrasion of a rotating ball. With this method, the limit value is an abrasion of 460 ⁇ m.
  • the reference fuel used for the tests was a sulfur-free, non-additive diesel fuel with an abrasion value of 569 ⁇ m.
  • Fatty acid monoalkyl esters with a content of more than 50% saturated fatty acids are ideal additives for improving the lubricating properties of sulfur-free diesel fuels.
  • the starting product was animal fat with the following fatty acid composition:
  • Palmitic acid 25.17%
  • Linoleic acid 9.24% This fat was converted into the corresponding fatty acid methyl esters using known methods using methanol and potassium hydroxide. The fatty acid methyl esters obtained were separated by fractional crystallization at low temperatures into two fractions, of which one fraction with a high proportion of saturated fatty acids was used 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: 21.26% linoleic acid: 2.62%
  • Example 2 A technical fatty acid distillate from palm oil with the following fatty acid composition was used as the raw material for the production of fatty acid methyl esters:
  • This fatty acid mixture was made using methanol and conc. Implemented sulfuric acid as a catalyst, the corresponding fatty acid methyl esters being obtained.
  • Palm stearin which was produced by fractional crystallization from palm oil, with the following fatty acid composition was used as the raw material for the production of fatty acid methyl esters:
  • Palm stearin was subjected to a multi-stage transesterification using methanol and potassium hydroxide as a catalyst, whereby the corresponding fatty acid methyl esters were obtained.
  • This plam oil was subjected to a multistage transesterification using methanol and potassium hydroxide as a catalyst, the corresponding fatty acid methyl esters being obtained.

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)
  • Fats And Perfumes (AREA)
PCT/AT2004/000214 2003-07-28 2004-06-22 Schwefelarmer dieseltreibstoff sowie verwendung von fettsäuremonoalkylestern als schmierfähigkeitsverbesserer für schwefelarme dieseltreibstoffe WO2005010130A1 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP04737103A EP1648984A1 (de) 2003-07-28 2004-06-22 Schwefelarmer dieseltreibstoff sowie verwendung von fettsäur emonoalkylestern als schmierfä higkeitsverbesserer für s chwefelarme dieseltreibstoffe
NZ545545A NZ545545A (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
CA002533657A 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
AU2004259773A AU2004259773B2 (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
CN2004800281298A CN1860209B (zh) 2003-07-28 2004-06-22 贫硫柴油以及脂肪酸单烷基酯作为贫硫柴油燃料的润滑改性剂的用途
US11/341,259 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
HK07102628.9A HK1097567A1 (en) 2003-07-28 2007-03-09 Low-sulphur diesel fuel and use of fatty acid monoalkyl esters as lubricant improvers for low-sulphur diesel fuels

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AT0119403A AT504745B1 (de) 2003-07-28 2003-07-28 Schwefelarmer dieseltreibstoff sowie verwendung von fettsäuremonoalkylestern als schmierfähigkeitsverbesserer für schwefelarme dieseltreibstoffe
ATA1194/2003 2003-07-28

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/341,259 Continuation 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 WO2005010130A1 (de) 2005-02-03

Family

ID=34085018

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AT2004/000214 WO2005010130A1 (de) 2003-07-28 2004-06-22 Schwefelarmer dieseltreibstoff sowie verwendung von fettsäuremonoalkylestern als schmierfähigkeitsverbesserer für schwefelarme dieseltreibstoffe

Country Status (9)

Country Link
US (1) US20060213118A1 (zh)
EP (1) EP1648984A1 (zh)
CN (1) CN1860209B (zh)
AT (1) AT504745B1 (zh)
AU (1) AU2004259773B2 (zh)
CA (1) CA2533657A1 (zh)
HK (1) HK1097567A1 (zh)
NZ (1) NZ545545A (zh)
WO (1) WO2005010130A1 (zh)

Cited By (8)

* 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 Researchmaatschappij B.V. Fuel compositions
EP1731589A2 (en) * 2005-06-10 2006-12-13 Malaysian Palm Oil Board Palm-based biodiesel formulation
FR2894977A1 (fr) * 2005-12-21 2007-06-22 Total France Sa Composant ameliorant de cetane pour carburants diesels et carburants diesel le contenant
FR2894978A1 (fr) * 2005-12-21 2007-06-22 Total France Sa Composant ameliorant de cetane pour carburants diesels et carburants diesel le contenant
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
CN112779064A (zh) * 2019-11-11 2021-05-11 中国石油化工股份有限公司 一种低酸型柴油抗磨剂及其制备方法和应用
US11732628B1 (en) 2020-08-12 2023-08-22 Old World Industries, Llc Diesel exhaust fluid

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102295961B (zh) * 2011-07-21 2013-09-04 淄博润博化工销售有限公司 一种低硫柴油润滑性添加剂及其制备方法
CN102311838A (zh) * 2011-08-08 2012-01-11 华东理工大学 一种低硫柴油润滑添加剂及其制备方法与应用
CN102977945B (zh) * 2012-11-12 2015-07-08 黄河三角洲京博化工研究院有限公司 一种柴油润滑性改进剂
AT513799B1 (de) 2012-12-18 2020-02-15 Mag Schell Klaus Verfahren zur Herstellung eines Bio-Diesel-Kraftstoffes mit einem speziell ausgelegten Reaktor und quasi katalytisch wirksamer nanoskalig strukturierter Materialoberfläche des Reaktors
RU2642080C1 (ru) * 2016-08-12 2018-01-24 Федеральное государственное бюджетное образовательное учреждение высшего образования "Вятский государственный университет" Топливная композиция
CN107177398B (zh) * 2017-06-07 2020-01-31 上海鑫灵精细化工有限公司 柴油抗磨剂及其制备方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (de) * 2001-03-08 2002-09-12 Wolfram Radig Multifunktioneller Zusatz für entschwefelte Mineraldieselkraftstoffe
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

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5891203A (en) * 1998-01-20 1999-04-06 Ethyl Corporation Fuel lubricity from blends of a diethanolamine derivative and biodiesel
US20040231234A1 (en) * 2003-05-19 2004-11-25 May Choo Yuen Palm diesel with low pour point for climate countries

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (de) * 2001-03-08 2002-09-12 Wolfram Radig Multifunktioneller Zusatz für entschwefelte Mineraldieselkraftstoffe
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 (14)

* 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 Researchmaatschappij 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
FR2894978A1 (fr) * 2005-12-21 2007-06-22 Total France Sa Composant ameliorant de cetane pour carburants diesels et carburants diesel le contenant
WO2007077330A2 (fr) * 2005-12-21 2007-07-12 Total France Composant ameliorant de cetane pour carburants diesels et carburants diesel le contenant
WO2007077330A3 (fr) * 2005-12-21 2007-08-23 Total France Composant ameliorant de cetane pour carburants diesels et carburants diesel le contenant
FR2894977A1 (fr) * 2005-12-21 2007-06-22 Total France Sa Composant ameliorant de cetane pour carburants diesels et carburants diesel le contenant
US8409304B2 (en) 2005-12-21 2013-04-02 Total France Cetane-improving component for diesel fuels and diesel fuels containing it
KR101327934B1 (ko) 2005-12-21 2013-11-13 토탈 라피나쥬 마케팅 디젤유용 세탄 개량제 및 이를 포함하는 디젤유
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
CN112779064A (zh) * 2019-11-11 2021-05-11 中国石油化工股份有限公司 一种低酸型柴油抗磨剂及其制备方法和应用
CN112779064B (zh) * 2019-11-11 2022-12-13 中国石油化工股份有限公司 一种低酸型柴油抗磨剂及其制备方法和应用
US11732628B1 (en) 2020-08-12 2023-08-22 Old World Industries, Llc Diesel exhaust fluid

Also Published As

Publication number Publication date
CN1860209B (zh) 2010-12-15
AT504745B1 (de) 2010-07-15
US20060213118A1 (en) 2006-09-28
AU2004259773B2 (en) 2010-02-11
CN1860209A (zh) 2006-11-08
AU2004259773A1 (en) 2005-02-03
CA2533657A1 (en) 2005-02-03
EP1648984A1 (de) 2006-04-26
NZ545545A (en) 2010-06-25
AT504745A1 (de) 2008-07-15
HK1097567A1 (en) 2007-06-29

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