EP1421159A1 - Correcteur de pouvoir lubrifiant pour gazoles - Google Patents

Correcteur de pouvoir lubrifiant pour gazoles

Info

Publication number
EP1421159A1
EP1421159A1 EP02767423A EP02767423A EP1421159A1 EP 1421159 A1 EP1421159 A1 EP 1421159A1 EP 02767423 A EP02767423 A EP 02767423A EP 02767423 A EP02767423 A EP 02767423A EP 1421159 A1 EP1421159 A1 EP 1421159A1
Authority
EP
European Patent Office
Prior art keywords
diesel oil
formula
compounds
use according
oil
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP02767423A
Other languages
German (de)
English (en)
Inventor
Frank Bongardt
Jürgen Röder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Cognis Deutschland GmbH and 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 and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1421159A1 publication Critical patent/EP1421159A1/fr
Withdrawn legal-status Critical Current

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.
  • 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 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.
  • 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.
  • 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.

Landscapes

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

Abstract

L'invention concerne l'utilisation d'esters d'alkylèneglycol d'acides gras, liquides à 21 °C, de formule générale (I), R-COO-(AO)n-H (I), dans laquelle R signifie un reste alkyle ou alcényle comptant 5 à 19 atomes de carbone, A désigne les groupes CH2-CH2 ou C3H6 et n est un nombre entre 0,5 et 6, en tant qu'additifs pour améliorer le pouvoir lubrifiant de gazoles, en particulier de gazoles pauvres en soufre.
EP02767423A 2001-09-01 2002-08-23 Correcteur de pouvoir lubrifiant pour gazoles Withdrawn EP1421159A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10143021A DE10143021A1 (de) 2001-09-01 2001-09-01 Schmierfähigkeitsverbesserer für Dieselöl
DE10143021 2001-09-01
PCT/EP2002/009439 WO2003020851A1 (fr) 2001-09-01 2002-08-23 Correcteur de pouvoir lubrifiant pour gazoles

Publications (1)

Publication Number Publication Date
EP1421159A1 true EP1421159A1 (fr) 2004-05-26

Family

ID=7697484

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02767423A Withdrawn EP1421159A1 (fr) 2001-09-01 2002-08-23 Correcteur de pouvoir lubrifiant pour gazoles

Country Status (4)

Country Link
US (1) US20040237385A1 (fr)
EP (1) EP1421159A1 (fr)
DE (1) DE10143021A1 (fr)
WO (1) WO2003020851A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005123890A1 (fr) * 2004-06-22 2005-12-29 Akzo Nobel N.V. Biodiesels ramifies
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
US10723966B2 (en) 2015-06-30 2020-07-28 Universidad De La Frontera Bio-additive for heavy oils, which comprises rapeseed oil methyl esters, surfactants, diluents and metal oxides, and use thereof for reducing polluting emissions and as a combustion efficiency bio-enhancer for heavy oils
WO2017006141A1 (fr) 2015-07-06 2017-01-12 Rhodia Poliamida E Especialidades Ltda Compositions de diesel présentant un indice de cétane et des performances de pouvoir lubrifiant améliorés
WO2018220640A1 (fr) * 2017-06-02 2018-12-06 Hindustan Petroleum Corporation Limited Formulation destinée à augmenter le pouvoir lubrifiant de carburants

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2807525A (en) * 1950-10-04 1957-09-24 Standard Oil Co Additive for motor fuels
US3287273A (en) * 1965-09-09 1966-11-22 Exxon Research Engineering Co Lubricity additive-hydrogenated dicarboxylic acid and a glycol
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
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
IT1270954B (it) * 1993-07-21 1997-05-26 Euron Spa Composizione di gasolio
US5882364A (en) * 1995-07-14 1999-03-16 Exxon Chemical Patents Inc. Additives and fuel oil compositions
GB2307247B (en) * 1995-11-13 1999-12-29 Ethyl Petroleum Additives Ltd Fuel additive
FR2751982B1 (fr) * 1996-07-31 2000-03-03 Elf Antar France Additif d'onctuosite pour carburant moteurs et composition de carburants
FR2752850A1 (fr) * 1996-08-27 1998-03-06 Inst Francais Du Petrole Compositions d'additifs ameliorant le pouvoir lubrifiant des carburants et carburants les contenant
US6300508B1 (en) * 1997-07-30 2001-10-09 Henkel Kommanditgesellschaft Auf Aktien Thickened aqueous surfactant solutions
FR2772784B1 (fr) * 1997-12-24 2004-09-10 Elf Antar France Additif d'onctuosite pour carburant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03020851A1 *

Also Published As

Publication number Publication date
US20040237385A1 (en) 2004-12-02
DE10143021A1 (de) 2003-03-20
WO2003020851A1 (fr) 2003-03-13

Similar Documents

Publication Publication Date Title
EP0012345B1 (fr) Carburants et leur utilisation
DE69108869T2 (de) Zusammensetzung und Verfahren betreffend Diesel angetriebene Fahrzeuge.
DE60119964T2 (de) Kraftstoffzusammensetzung
DE3525124A1 (de) Kraftstoffe und heizoele und verwendung eines emulgatorsystems zur herstellung dieser kraftstoffe und heizoele
DE69921281T2 (de) Brennstoffe mit erhöhter Schmiereigenschaft
DE4020664A1 (de) Ester enthaltende kraftstoffe fuer ottomotoren und dieselmotoren
DE102008005346A1 (de) Neuer synthetischer Kraftstoff und Verfahren zum Herstellen desselben
DE19955651A1 (de) Verwendung von Festsäuresalzen von alkoxylierten Oligoaminen als Schmierfähigkeitsverbesserer für Mineralölprodukte
EP1421159A1 (fr) Correcteur de pouvoir lubrifiant pour gazoles
DE69804804T2 (de) Verbesserte brennölzusammensetzungen
DE1144971B (de) Kohlenwasserstoff-Kraftstoff vom Benzin-Siedebereich
DE69823742T2 (de) Etheraminalkoxylate enthaltende Brennstoffzusammensetzungen
EP2759588A1 (fr) Carburant pour moteurs à allumage par compression à base de monooxyméthylènediméthyléther
EP1537192A1 (fr) Melange d'additifs pour carburants et lubrifiants
WO2006053664A1 (fr) Additif pour ameliorer le pouvoir lubrifiant de carburants diesel
EP1381658B1 (fr) Melange d'emulsifiants pour emulsions diesel aqueuses
WO2005087900A1 (fr) Compositions de combustibles
DE4137852A1 (de) Carbamidsaeureester, verfahren zu ihrer herstellung sowie kraft- und schmierstoffe, enthaltend die carbamidsaeureester
DE60120130T2 (de) Brennstoffzusätze
WO2004041975A1 (fr) Carburants contenant un additif a effet ameliore
EP0081744B1 (fr) Additifs pour combustibles destinés à des moteurs à combustion interne
EP1444312B1 (fr) Additif pour carburant a faible teneur en soufre
DE3709195A1 (de) Lagerstabile emulgatoren
EP1923453A1 (fr) Additifs et leur utilisation comme agent pour améliorer la solubilité dans les combustibles
EP1558710A1 (fr) Additifs ameliorant la fluidite de carburants

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20040221

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LI LU MC NL PT SE SK TR

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: COGNIS DEUTSCHLAND GMBH & CO. KG

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: COGNIS IP MANAGEMENT GMBH

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20090303