WO2003020851A1 - Schmierfähigkeitsverbesserer für dieselöl - Google Patents
Schmierfähigkeitsverbesserer für dieselöl Download PDFInfo
- Publication number
- WO2003020851A1 WO2003020851A1 PCT/EP2002/009439 EP0209439W WO03020851A1 WO 2003020851 A1 WO2003020851 A1 WO 2003020851A1 EP 0209439 W EP0209439 W EP 0209439W WO 03020851 A1 WO03020851 A1 WO 03020851A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- diesel oil
- formula
- compounds
- use according
- oil
- Prior art date
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
- C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
-
- 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
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
Definitions
- the present application relates to the use of additives for improving the lubricity of diesel oil, a low-sulfur diesel oil which contains such additives and a method for improving the lubricity of diesel oils.
- the present application relates to the use of fatty acid alkylene glycol esters of the general formula (I) which are liquid at 21.degree.
- R represents an alkyl or alkenyl radical having 5 to 19 carbon atoms
- AO represents the groups CH2-CH2 or C3H6 and n is a number between 0.5 and 6, as an additive to improve the lubricity of diesel oil.
- Esters and their alkoxylates are already known from WO 96/23855 as additives for improving the lubricity of diesel oils.
- WO 96/23855 does not disclose the low alkoxylated compounds of the present invention. Specifically, only one sorbitan or one glycerol monoleate is disclosed. Diesel fuels or diesel oils or simply diesel are flame-retardant mixtures of liquid hydrocarbons, which are used as fuels for constant pressure or burner engines (diesel engines) and mainly from paraffins with admixtures of olefins, naphthenes and the like. aromatic hydrocarbons exist.
- Diesel oil is obtained from the distillation of petroleum from the gas oil, from cracking, from the tars which are obtained from the smoldering (or hydrogenation) of brown or hard coal, and the like. by hydrogenating the coal extract. Diesel oils for stationary systems and for marine engines have a similar composition to heavy heating oil, which corresponds to heating oil for cars, buses and trucks.
- Ignitability refers to the property of an engine fuel to ignite more easily or more difficultly in an engine operating on the diesel principle. In addition to atomization, pressure and temperature, this requires a preparation time (ignition delay) until the combustion can be determined. Good 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 fuels for slow-running engines are CZ 20-40, for small and fast-running CZ> 45 or - preferred today - by the limit value of the filterability (cold filter plugging point, CFPP), the temperature at which sucked-through diesel fuel can block a filter, a low pour point, a low content of non-combustible and sooty substances and a low sulfur content
- the additives according to the invention are particularly suitable for use in low-sulfur diesel oils, ie diesel oil with a maximum sulfur content of 0.05% by weight, preferably 0.03 or less% by weight, in DIN-EN 590 (05/1993) the requirements and test methods for diesel fuel are specified throughout Europe.
- the fatty acid alkylene glycols are addition products of ethylene oxide (EO) or propylene oxide (PO) or both of EO and PO with fatty acids of the formula RCOOH, in which R 1 is as defined above.
- EO ethylene oxide
- PO propylene oxide
- RCOOH fatty acids of the formula RCOOH, in which R 1 is as defined above.
- Compounds which contain only EO (CH2-CH2 groups) or only propylene oxide groups (CaH ⁇ groups) are preferred; the ethoxylated compounds are particularly preferred.
- Typical examples are caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid, and technical mixtures, e.g.
- the alkoxylates used according to the invention are ethoxylated and / or propoxylated fatty acids, which are also referred to as fatty acid alkylene glycols, and are compounds known per se. They can be prepared, for example, according to German published patent application DE-A-2024050 by reacting carboxylic acids with alkylene oxides in the presence of amines as catalysts. According to this process, however, the low alkoxylated compounds are obtained in yields well below 90% of theory. According to this process, the ethoxylation is carried out in the presence of alkanolamines as catalyst and gives significantly higher yields.
- the propoxylation and / or ethoxylation-propoxylation reaction can be carried out in a manner known per se.
- the fatty acid and the catalyst are placed in a stirred autoclave, which is placed in front the reaction is freed from traces of water by alternately evacuating and flushing with nitrogen.
- the fatty acid is then reacted with the propylene oxide or with the ethylene oxide / propylene oxide mixture in a molar ratio of 1: 0.5 to 1: 1.5, which can be metered into portions of the pressure vessel after heating by means of a siphon.
- the fatty acids are preferably reacted with one mole to 2 moles of propylene oxide or with one to 2 moles of the ethylene oxide / propylene oxide mixture.
- the reaction can be carried out at temperatures in the range from 80 to 180 ° C., preferably 100 to 120 ° C. and autogenous pressures in the range from 1 to 5, preferably 2 to 3 bar. After the end of the reaction, it is advisable to stir at the reaction temperature for a certain time to complete the conversion (15 to 90 min). The autoclave is then cooled, decompressed and, if desired, acids such as lactic acid or phosphoric acid are added to the product in order to neutralize the basic catalyst.
- liquid compounds of the formula (I) above can generally be used.
- Preferred are those in which n is a number from 0.5 to 2.5 and in particular from 0.5 to 1.5. the odd numbers result from averaging over the different degrees of alkoxylation of the individual compounds.
- a value of n indicates a proportion of unesterified acids.
- additives according to formula (I) in which n is 1 or greater are preferred.
- alkoxylates of the formula (I) if they are alkoxylates with a narrow homolog distribution.
- the compounds of formula (I) should preferably contain more than 90% of a homologue.
- the homologs of the formula (I) with n equal to 1 are particularly preferred.
- the ester is liquid at 21 ° C. (room temperature).
- Compounds of the formula (I) which are obtained on the basis of fatty acid mixtures from sunflower, tall, soybean or rapeseed oil are therefore particularly suitable. It is also preferred to select fatty acids with at least one olefinic double bond as the fatty acid component.
- the mono- or poly-branched fatty acids can also be used to prepare the additives of the formula (I). Additives based on oleic acid (a cis-unsaturated fatty acid) are particularly preferred.
- the additives of formula (I) are added to the diesel oil in amounts of 10 to 1000 ppm, preferably 10 to 250 ppm and in particular 10 to 100 ppm. It is preferred to use less than 100 ppm of the additive. As stated above, the amount of additive should be kept as low as possible. This is achieved according to the invention.
- additives in particular cetane number improvers (nitric or nitrous acid esters), corrosion inhibitors, flow improvers, surfactants (keep the injection nozzles clean), defoamers, and sometimes also smoke reducers, are usually added to the diesel as additives.
- Car exhaust gases from diesel fuels contain more nitrogen oxides and 30 to 100 times more particles (“soot") than those from gasoline fuels after catalytic cleaning.
- Such additives can also be used in combination with the inventive ones. However, preferably no further additives should be used to improve the lubricity be used.
- the present invention further relates to a diesel oil with a sulfur content of at most 0.05% by weight of sulfur which contains additives of the formula (I) to improve the lubricity, preferably in amounts of 10 to 1000 and in particular in amounts of less than 100 ppm. It is further preferred if the diesel oil is free of acylated nitrogen-containing compounds and of free alcohols, in particular fatty alcohols having 6 to 22 carbon atoms and their derivatives, in particular their alkoxylated derivatives.
- the diesel oil according to the invention should contain less than 0.05% by weight of sulfur and have a distillation point (95% - according to ASTM-D86) of at most 350 ° C.
- the so-called flash point should be at least 38 ° C.
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02767423A EP1421159A1 (de) | 2001-09-01 | 2002-08-23 | Schmierfähigkeitsverbesserer für dieselöl |
US10/488,303 US20040237385A1 (en) | 2001-09-01 | 2002-08-23 | Lubricity improver for diesel oil |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10143021.3 | 2001-09-01 | ||
DE10143021A DE10143021A1 (de) | 2001-09-01 | 2001-09-01 | Schmierfähigkeitsverbesserer für Dieselöl |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003020851A1 true WO2003020851A1 (de) | 2003-03-13 |
Family
ID=7697484
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/009439 WO2003020851A1 (de) | 2001-09-01 | 2002-08-23 | Schmierfähigkeitsverbesserer für dieselöl |
Country Status (4)
Country | Link |
---|---|
US (1) | US20040237385A1 (de) |
EP (1) | EP1421159A1 (de) |
DE (1) | DE10143021A1 (de) |
WO (1) | WO2003020851A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005123890A1 (en) * | 2004-06-22 | 2005-12-29 | Akzo Nobel N.V. | Branched biodiesels |
WO2017006141A1 (en) | 2015-07-06 | 2017-01-12 | Rhodia Poliamida E Especialidades Ltda | Diesel compositions with improved cetane number and lubricity performances |
US11060043B2 (en) * | 2017-06-02 | 2021-07-13 | Hindustan Petroleum Corporation Limited | Formulation for enhancing lubricity of fuels |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10215424B2 (en) | 2013-11-27 | 2019-02-26 | Advanced Conservation Technology Distribution, Inc | Methods and apparatus for remotely monitoring and/or controlling a plumbing system |
WO2017001896A1 (es) | 2015-06-30 | 2017-01-05 | Universidad De La Frontera | Bioaditivo para petróleos pesados, que comprende metil ésteres de aceite de raps, tensoactivos, diluyentes y óxidos metálicos y su uso para reducir emisiones contaminantes y biomejorador del rendimiento de combustión para petróleos pesados |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3287273A (en) * | 1965-09-09 | 1966-11-22 | Exxon Research Engineering Co | Lubricity additive-hydrogenated dicarboxylic acid and a glycol |
US4617026A (en) * | 1983-03-28 | 1986-10-14 | Exxon Research And Engineering Company | Method for improving the fuel economy of an internal combustion engine using fuel having hydroxyl-containing ester additive |
EP0635558A1 (de) * | 1993-07-21 | 1995-01-25 | EURON S.p.A. | Dieselölzusammensetzung |
EP0773278A1 (de) * | 1995-11-13 | 1997-05-14 | Ethyl Petroleum Additives Limited | Kraftstoffzusatz |
WO1998004656A1 (fr) * | 1996-07-31 | 1998-02-05 | Elf Antar France | Carburant pour moteurs diesel a faible teneur en soufre |
EP0826765A1 (de) * | 1996-08-27 | 1998-03-04 | Institut Francais Du Petrole | Zusammensetzungen von Treibstoffschmiereigenschaften verbesserenden Zusätzen, und diese enthaltende Treibstoffe |
US5882364A (en) * | 1995-07-14 | 1999-03-16 | Exxon Chemical Patents Inc. | Additives and fuel oil compositions |
FR2772784A1 (fr) * | 1997-12-24 | 1999-06-25 | Elf Antar France | Additif d'onctuosite pour carburant |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2807525A (en) * | 1950-10-04 | 1957-09-24 | Standard Oil Co | Additive for motor fuels |
US3884946A (en) * | 1970-05-16 | 1975-05-20 | Henkel & Cie Gmbh | Process for the production of alkylene glycol monoesters |
US3920414A (en) * | 1972-10-27 | 1975-11-18 | Exxon Research Engineering Co | Crude oils containing nitrogen dispersants and alkoxylated ashless surfactants usable as diesel fuels |
US6300508B1 (en) * | 1997-07-30 | 2001-10-09 | Henkel Kommanditgesellschaft Auf Aktien | Thickened aqueous surfactant solutions |
-
2001
- 2001-09-01 DE DE10143021A patent/DE10143021A1/de not_active Withdrawn
-
2002
- 2002-08-23 EP EP02767423A patent/EP1421159A1/de not_active Withdrawn
- 2002-08-23 WO PCT/EP2002/009439 patent/WO2003020851A1/de not_active Application Discontinuation
- 2002-08-23 US US10/488,303 patent/US20040237385A1/en not_active Abandoned
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3287273A (en) * | 1965-09-09 | 1966-11-22 | Exxon Research Engineering Co | Lubricity additive-hydrogenated dicarboxylic acid and a glycol |
US4617026A (en) * | 1983-03-28 | 1986-10-14 | Exxon Research And Engineering Company | Method for improving the fuel economy of an internal combustion engine using fuel having hydroxyl-containing ester additive |
EP0635558A1 (de) * | 1993-07-21 | 1995-01-25 | EURON S.p.A. | Dieselölzusammensetzung |
US5882364A (en) * | 1995-07-14 | 1999-03-16 | Exxon Chemical Patents Inc. | Additives and fuel oil compositions |
EP0773278A1 (de) * | 1995-11-13 | 1997-05-14 | Ethyl Petroleum Additives Limited | Kraftstoffzusatz |
WO1998004656A1 (fr) * | 1996-07-31 | 1998-02-05 | Elf Antar France | Carburant pour moteurs diesel a faible teneur en soufre |
EP0826765A1 (de) * | 1996-08-27 | 1998-03-04 | Institut Francais Du Petrole | Zusammensetzungen von Treibstoffschmiereigenschaften verbesserenden Zusätzen, und diese enthaltende Treibstoffe |
FR2772784A1 (fr) * | 1997-12-24 | 1999-06-25 | Elf Antar France | Additif d'onctuosite pour carburant |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005123890A1 (en) * | 2004-06-22 | 2005-12-29 | Akzo Nobel N.V. | Branched biodiesels |
WO2017006141A1 (en) | 2015-07-06 | 2017-01-12 | Rhodia Poliamida E Especialidades Ltda | Diesel compositions with improved cetane number and lubricity performances |
WO2017006167A1 (en) | 2015-07-06 | 2017-01-12 | Rhodia Poliamida E Especialidades Ltda | Diesel compositions with improved cetane number and lubricity performances |
US11072753B2 (en) | 2015-07-06 | 2021-07-27 | Rhodia Poliamida E Especialidades S.A. | Diesel compositions with improved cetane number and lubricity performances |
US11060043B2 (en) * | 2017-06-02 | 2021-07-13 | Hindustan Petroleum Corporation Limited | Formulation for enhancing lubricity of fuels |
Also Published As
Publication number | Publication date |
---|---|
EP1421159A1 (de) | 2004-05-26 |
US20040237385A1 (en) | 2004-12-02 |
DE10143021A1 (de) | 2003-03-20 |
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