EP1124916B1 - Emulsionnants de paraffine a effet lubrifiant pour distillats de produits petroliers - Google Patents

Emulsionnants de paraffine a effet lubrifiant pour distillats de produits petroliers Download PDF

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Publication number
EP1124916B1
EP1124916B1 EP99953878A EP99953878A EP1124916B1 EP 1124916 B1 EP1124916 B1 EP 1124916B1 EP 99953878 A EP99953878 A EP 99953878A EP 99953878 A EP99953878 A EP 99953878A EP 1124916 B1 EP1124916 B1 EP 1124916B1
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Prior art keywords
mineral oil
mixture according
weight
distillates
reaction product
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EP1124916A1 (fr
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Bernd Wenderoth
Dieter Hermeling
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BASF SE
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BASF SE
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    • 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
    • C10L1/22Organic compounds containing nitrogen
    • 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
    • C10L1/143Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • 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
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/221Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • 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
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224Amides; Imides carboxylic acid amides, imides
    • 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
    • C10L1/16Hydrocarbons
    • C10L1/1616Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
    • 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
    • C10L1/188Carboxylic acids; metal salts thereof
    • C10L1/1881Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • C10L1/1883Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom polycarboxylic acid
    • 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
    • C10L1/192Macromolecular compounds
    • C10L1/195Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/197Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
    • C10L1/1973Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
    • 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
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic 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
    • 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
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic 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

Definitions

  • This invention relates to paraffin dispersants having lubricity effects suitable mixtures, their use in petroleum middle distillates, such petroleum middle distillates and concentrates therefor.
  • Middle distillates such as gas oils, diesel oils or light heating oils, which are obtained by distillation from petroleum oils, have different contents of paraffins depending on the origin of the crude oil.
  • solid paraffins are excreted (cloud point or cloud point, CP).
  • the platy n-paraffin crystals form a kind of "house of cards structure" and the middle distillate stagnates, although the majority of the middle distillate is still liquid.
  • the precipitated n-paraffins in the temperature range between cloud point (cloud point) and pour point (pour point) the flowability of middle distillate fuels is significantly affected;
  • the paraffins clog filters and cause uneven or completely interrupted fuel supply to the combustion units. Similar disturbances occur with light fuel oils.
  • Ethylene vinyl carboxylate copolymers have long been used as flow improvers.
  • a disadvantage of these additives is that the precipitated paraffin crystals tend due to their relative to the liquid part higher density tend to settle more and more at the bottom of the container during storage. As a result, a homogeneous low-paraffin phase forms in the upper container part and a two-phase paraffin-rich layer at the bottom. Since the deduction of the middle distillate mostly takes place slightly above the container bottom both in the vehicle tanks and in storage or delivery tanks of the mineral oil dealer, there is a risk that the high concentration of solid paraffins leads to blockages of filters and metering devices. This danger is greater the further the storage temperature falls below the excretion temperature of the paraffins, since the amount of paraffin precipitated increases with decreasing temperature.
  • wax dispersants can reduce these problems.
  • EP-A-0 398 101 describes reaction products of aminoalkylene polycarboxylic acids with long-chain secondary amines as paraffin dispersants for petroleum middle distillates.
  • the effect is not sufficient in all petroleum middle distillate compositions, especially if they have a low sulfur content of less than 500 ppm.
  • DE-A-11 49 843 describes the use of maleamic acids and their amine salts of primary amines and maleic anhydride as corrosion inhibitors and stability improvers for petroleum distillates as well as for the prevention of sedimentation.
  • EP-A-0 106 234 describes the use of amine salts of maleamic acids from primary amines and maleic anhydride as corrosion inhibitors for the storage and transport of crude oils.
  • lubricity additives can improve the lubricity of low-sulfur diesel fuels.
  • the effectiveness is determined according to the standard CEC F-06-A-96 with the HFRR test (High Frequency Reciprocating Rig-Test) by determining the wear size WS1.4 in ⁇ m at 60 ° C; the smaller the WS1.4, the lower the wear and the better the lubricity.
  • WO-A-9 746 640 describes a mixture comprising (a) 10 to 90% by weight of at least one imide of a copolymer based on an ⁇ -olefin and an ethylenically unsaturated dicarboxylic acid and a polyamine and (b) 10 to 90 % By weight of at least one reaction product of a poly (C 2-20 -carboxylic acid) having at least one tertiary amino group with secondary amines, and their use as paraffin dispersants in petroleum middle distillates.
  • the object was to provide improved products which ensure improved flowability of petroleum middle distillates at low temperature by having such a dispersing effect that delaying or preventing settling of precipitated paraffins and simultaneously contributing to improved lubricity of the petroleum middle distillates ,
  • the invention also relates to the use of these mixtures as an additive for petroleum middle distillates, in particular as paraffin dispersant and lubricity additive.
  • the invention also relates to these mixtures containing concentrates and petroleum middle distillates.
  • Component (a) is a reaction product of a tertiary amino group containing poly (C 2-20 carboxylic acid) with secondary amines.
  • the polycarboxylic acid preferably contains at least 3 carboxyl groups, particularly preferably 3 to 12, in particular 3 to 5, carboxyl groups.
  • the carboxylic acid groups in the polycarboxylic acid preferably have 2 to 10 carbon atoms, preferably acetic acid groups.
  • the carboxylic acid groups are suitably linked to the polycarboxylic acid, for example via one or more C and / or N atoms. Preferably, they are attached to tertiary nitrogen atoms, which are linked in the case of several nitrogen atoms via hydrocarbon chains.
  • Component (a) is preferably an amide, amide ammonium salt, ammonium salt or a mixture thereof of aminoalkylcarboxylic acids of the formulas I and II where A is a straight-chain or branched alkylene radical having 2 to 6, preferably 2 to 4, in particular 2 or 3, carbon atoms or the radical of the formula (III) where B is a radical having 1 to 19 carbon atoms, preferably a C 1-19 -alkylene radical, particularly preferably C 1-10 -alkylene radical, in particular a methylene radical.
  • A is an ethylene radical.
  • the secondary amine may be selected from a variety of amines carrying hydrocarbon radicals, optionally linked together.
  • the secondary amine preferably has the formula HNR 2 , wherein the radicals R are independently straight-chain aliphatic radicals, in particular alkyl radicals having 10 to 30, preferably 14 to 24 carbon atoms. They preferably have no heteroatoms or double or triple bonds. Preferably, the radicals R are the same.
  • the secondary amines can be bound to the polycarboxylic acid by means of amide structures or in the form of the ammonium salts, partly also by means of amide structures and partly in the form of the ammonium salts. Preferably, there are little or no free acid groups.
  • the amines are fully bonded in the form of the amide structures.
  • the amides, or amide ammonium salts or ammonium salts of nitrilotriacetic acid, ethylenediaminetetraacetic acid or propylene-1,2-diaminetetraacetic acid are prepared by reacting the acids with from 0.5 to 1.5 mol of amine, preferably from 0.8 to 1.2 mol Amine per carboxyl group.
  • reaction temperatures are about 80 to 200 ° C, wherein for the preparation of the amides, a continuous removal of the resulting reaction water.
  • the reaction does not have to be completely led to the amide, but may be 0 to 100 mol% of the amine used in the form of the ammonium salt.
  • Especially preferred amines are dioleylamine, dipalmitinamine, dicoco fatty amine and dibehenylamine, especially ditallow fatty amine.
  • mixture components (a) according to the invention and their preparation are described in EP-A-0 398 101. Particularly preferred is the reaction product of one mole of ethylenediaminetetraacetic acid and four moles of hydrogenated Ditalgfettamin.
  • the mixture components (a) can still small amounts of conductivity in the form of salts, in particular of hydrocarbon-soluble carboxylic acids and sulfonic acids or their metal and ammonium salts. be added.
  • the preparation of the mixture components (b) according to the invention is carried out in a manner known per se by reacting maleic anhydride with primary C 8-30 -alkylamine. Preference is given to using primary C 8 - to C 18 -alkylamines in a molar ratio of 1: 1 at from 70 to 100 ° C. according to the process described in DE-A-11 49 843 and EP-A-0 106 234.
  • Suitable primary amines are all amines defined within these limits, for example straight-chain or branched octyl, nonyl, decyl, undecyl, dodecyl, tricecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecylamine and mixtures these amines.
  • Particularly preferred is the reaction product of one mole of maleic anhydride and one mole of tridecylamine.
  • the mixtures according to the invention can be prepared by simply mixing components (a) and (b); These mixtures are added to the petroleum distillates in amounts of 10-1000 ppm, preferably 50-500 ppm.
  • the proportion of component (a) is 5 to 95, preferably 30 to 95, in particular 50 to 90 wt .-%, the proportion of component (b) 5 to 95, preferably 5 to 70, in particular 10 to 50 wt .-%.
  • the polymer blends of the invention are used as an additive for petroleum middle distillates, which are understood to include petroleum, light fuel oils and diesel fuels having a boiling point of about 150 to 400 ° C.
  • the polymer mixtures can be added directly to the middle distillates, but preferably as a 20 to 70% by weight solution (concentrate).
  • Suitable solvents are aliphatic or aromatic solvents such as xylene or mixtures thereof, furthermore high-boiling aromatic mixtures such as solvent naphtha, as well as middle distillates.
  • the amount of the mixture in the petroleum middle distillates is usually 10 to 10,000, preferably 20 to 5000, and more preferably 50 to 1000 ppm.
  • middle distillates still contain flow improvers, e.g. based on ethylene / vinylcarboxilate copolymers.
  • middle distillates may additionally contain further additives such as conductivity improvers, anti-corrosive additives, lubricity additives, antioxidants, metal deactivators, anti-foam agents, demulsifiers, detergents, cetane number improvers and / or dyes and fragrances.
  • the mixtures according to the invention in middle distillates significantly improve the flow properties in the cold by effectively keeping the precipitated paraffin crystals in suspension, so that blockages of filters and lines by sedimented paraffin do not occur. They have a good broad effect and cause so that the precipitated paraffin crystals are dispersed very well in different middle distillates; at the same time they contribute to an improved lubricity of the middle distillates.
  • the mixtures according to the invention were tested in two commercial German winter diesel fuels, which correspond to the European diesel fuel standard EN 590; they are referred to as D 1 and D 2 and are characterized by the following physical data: D 1 (97/526) D 2 (96/86) Cloud Point (° C) according to ISO 3015: -6 -6 CFPP (° C) according to EN 116: -10 -8th Density at 15 ° C (kg / m 3 ) according to ASTM D 4052: 841 834 Sulfur content (ppm) according to EN 24260: 160 200 WS1.4 ( ⁇ m) according to CEC F-06-A-96: 542 Distillation according to ISO 3405: Boiling start (° C) 170 171 5% boiling point (° C) 203 193 10% boiling point (° C) 215 200 20% boiling point (° C) 235 212 50% boiling point (° C) 280 249 70% boiling point (° C) 308 282 90% boiling point (° C) 347 329 95% boiling
  • the middle distillates were added with the amounts indicated in the table mixtures of the invention PD 1 to PD 4 or Examples 1 and 2 and the flow improver MDFI at 40 ° C with stirring and then cooled to room temperature.
  • the additized middle distillates were placed in 500 ml glass cylinders in a room temperature refrigerated bath at a cooling rate of about 14 ° C per hour cooled to -13 ° C and stored at this temperature for 20 hours. Subsequently, the amount and appearance of the paraffin phase were determined and assessed visually.
  • Table 1 Dispersing experiments in D 1, CP: -6 ° C, CFPP: -10 ° C, WS1.4: 542 ⁇ m mixture
  • test results show that the mixtures according to the invention, with the same total metering, lead to a lower WS1.4 and thus to an improved lubricity of low-sulfur diesel fuels than the respective individual components.

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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)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Degasification And Air Bubble Elimination (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Claims (10)

  1. Mélange contenant :
    (a) 5 à 95 % en poids d'au moins un produit de mise en réaction d'un acide poly(C2-20-carboxylique) avec des amines secondaires présentant au moins un groupe amino tertiaire et
    (b) 5 à 95 % en poids d'au moins un produit de mise en réaction d'anhydride d'acide maléique et d'une C8-C30-alkylamine primaire.
  2. Mélange selon la revendication 1, caractérisé en ce que l'acide poly(C2-20-carboxylique) présentant au moins un groupe amino tertiaire répond aux formules I ou II ci-dessous :
    Figure imgb0011
    Figure imgb0012
    dans lesquelles A désigne un reste C2-6-alkylène à chaîne droite ou ramifiée ou le reste de formule III
    Figure imgb0013
    dans laquelle B désigne un reste C1-19-alkylène.
  3. Mélange selon l'une des revendications 1 ou 2, caractérisé en ce que le produit de réaction (a) est un amide, un sel d'ammonium-amide ou un sel d'ammonium dans lequel aucun, un ou plusieurs groupes carboxyliques sont transformés en groupes amide.
  4. Mélange selon l'une des revendications 1 à 3, caractérisé en ce que l'amine secondaire du composant (a) présente la formule générale HNR2, les restes R étant des restes C10-30-alkyle qui sont linéaires ou ramifiés.
  5. Utilisation d'un mélange selon l'une des revendications 1 à 4 comme additif pour les distillats moyens de pétrole.
  6. Utilisation selon la revendication 5 comme agent dispersant de paraffine et additif de lubricité pour des distillats moyens de pétrole.
  7. Distillats moyens de pétrole contenant un mélange selon l'une des revendications 1 à 4.
  8. Distillat moyen de pétrole selon la revendication 7, contenant par ailleurs des agents améliorant la fluidité, des agents améliorant la conductivité, des additifs protecteurs contre la corrosion, des additifs de lubricité, des antioxydants, des désactivateurs métalliques, des agents antimousse, des démulsifiants, des détergents, des agents améliorant l'indice de cétane, des colorants ou des arômes ou mélanges de ceux-ci.
  9. Concentré contenant 10 à 60 % en poids par rapport à la quantité totale du concentré en un mélange selon l'une des revendications 1 à 4, dissous dans un solvant d'hydrocarbure.
  10. Distillat moyen de pétrole selon la revendication 7 qui contient par ailleurs des agents améliorant la fluidité à base de copolymères d'éthylène/de carboxylate vinylique.
EP99953878A 1998-10-21 1999-10-19 Emulsionnants de paraffine a effet lubrifiant pour distillats de produits petroliers Expired - Lifetime EP1124916B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19848621 1998-10-21
DE19848621A DE19848621A1 (de) 1998-10-21 1998-10-21 Paraffindispergatoren mit Lubricity-Wirkung für Erdölmitteldestillate
PCT/EP1999/007899 WO2000023541A1 (fr) 1998-10-21 1999-10-19 Emulsionnants de paraffine a effet lubrifiant pour distillats de produits petroliers

Publications (2)

Publication Number Publication Date
EP1124916A1 EP1124916A1 (fr) 2001-08-22
EP1124916B1 true EP1124916B1 (fr) 2006-10-11

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Country Link
US (1) US6786940B1 (fr)
EP (1) EP1124916B1 (fr)
JP (1) JP4603692B2 (fr)
KR (1) KR100693848B1 (fr)
AT (1) ATE342324T1 (fr)
CA (1) CA2347039C (fr)
DE (2) DE19848621A1 (fr)
DK (1) DK1124916T3 (fr)
ES (1) ES2275357T3 (fr)
NO (1) NO329079B1 (fr)
WO (1) WO2000023541A1 (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7132180B2 (en) * 2002-01-25 2006-11-07 Exxonmobil Research And Engineering Company Alkyl sorbitan emulsion compositions for fuel cell reformer start-up
US20030165722A1 (en) * 2002-01-25 2003-09-04 Ramesh Varadaraj Microemulsion compositions for fuel cell reformer start-up
DE10356595A1 (de) 2003-12-04 2005-06-30 Basf Ag Brennstoffölzusammensetzungen mit verbesserten Kaltfließeigenschaften
DE102004035157B3 (de) * 2004-07-20 2005-11-17 Clariant Gmbh Mineralöle mit verbesserter Leitfähigkeit und Kältefließfähigkeit
CN1993449A (zh) * 2004-08-06 2007-07-04 巴斯福股份公司 用于燃料和润滑剂的多胺添加剂
US20060130394A1 (en) * 2004-12-22 2006-06-22 Flint Hills Resources, L.P. Performance diesel fuels and additives
EP1746147B1 (fr) 2005-07-22 2016-02-24 Basf Se Copolymères à base d'oléfines et d'esters d'acides carboxyliques éthylèniquement insaturés pour abaiser le point de trouble des combustibles et des lubrifiants
EP1746146A1 (fr) 2005-07-22 2007-01-24 Basf Aktiengesellschaft Copolymères à base d'oléfines et d'esters d'acides carboxyliques éthylèniquement insaturés pour abaiser le point de trouble des combustibles et des lubrifiants
WO2007131894A2 (fr) * 2006-05-12 2007-11-22 Basf Se Compositions d'huiles combustibles résistantes au froid
ATE451441T1 (de) 2006-06-22 2009-12-15 Basf Se Mischung aus polaren öllöslichen stickstoffverbindungen und säureamiden als paraffindispergator für kraftstoffe
GB0902009D0 (en) * 2009-02-09 2009-03-11 Innospec Ltd Improvements in fuels
EP2230226B1 (fr) * 2009-03-18 2017-01-18 Infineum International Limited Additifs pour huiles de carburant
ES2437073T3 (es) 2009-04-07 2014-01-08 Basf Se Mezcla de compuestos de nitrógeno solubles en aceite polares y compuestos alifáticos solubles en aceite para la reducción del punto de enturbiamiento en combustibles destilados medios
WO2016025749A1 (fr) * 2014-08-13 2016-02-18 Lubrizol Oilfield Chemistry, Llc Dispersant de paraffine acceptable pour l'environnement, et leurs procédés de fabrication et d'utilisation
WO2020115133A1 (fr) 2018-12-04 2020-06-11 Total Marketing Services Compositions de piégeage du sulfure d'hydrogène et de mercaptans
US11952546B2 (en) 2018-12-04 2024-04-09 Total Marketing Services Hydrogen sulphide and mercaptans scavenging compositions
EP3891262B1 (fr) * 2018-12-04 2024-07-31 TotalEnergies OneTech Compositions pour le piégeage de sulfure d'hydrogène et de mercaptans
RS65269B1 (sr) 2021-04-15 2024-03-29 Basf Se Nove kompozicije za smanjenje kristalizacije kristala parafina u gorivima
EP4413101A1 (fr) * 2021-10-04 2024-08-14 Innospec Fuel Specialties LLC Améliorations de carburants
US20240059992A1 (en) * 2022-08-09 2024-02-22 Innospec Fuel Specialties Llc Fuels
WO2024056479A1 (fr) 2022-09-12 2024-03-21 Basf Se Nouvelles compositions pour réduire la cristallisation de cristaux de paraffine dans des combustibles

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE568954A (fr) 1958-01-07
DE3237109A1 (de) 1982-10-07 1984-04-12 Basf Ag, 6700 Ludwigshafen Verwendung von aminsalzen von maleinamidsaeuren als inhibitoren gegen die korrosion von co(pfeil abwaerts)2(pfeil abwaerts) und h(pfeil abwaerts)2(pfeil abwaerts)s in wasser-in-oel-emulsionen
EP0203812A1 (fr) 1985-05-28 1986-12-03 Exxon Research And Engineering Company Composition pour l'écoulement des combustibles à base de distillats moyens
DE3916366A1 (de) 1989-05-19 1990-11-22 Basf Ag Neue umsetzungsprodukte von aminoalkylenpolycarbonsaeuren mit sekundaeren aminen und erdoelmitteldestillatzusammensetzungen, die diese enthalten
DE4237662A1 (de) * 1992-11-07 1994-05-11 Basf Ag Erdölmitteldestillatzusammensetzungen
DE4324394A1 (de) * 1993-07-21 1995-01-26 Basf Ag Umsetzungsprodukte von Aminoalkylencarbonsäuren sowie Erdölmitteldestillate, die diese enthalten
GB9411614D0 (en) * 1994-06-09 1994-08-03 Exxon Chemical Patents Inc Fuel oil compositions
DE19622052A1 (de) * 1996-05-31 1997-12-04 Basf Ag Paraffindispergatoren für Erdölmitteldestillate

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ATE342324T1 (de) 2006-11-15
NO20011927L (no) 2001-06-20
DK1124916T3 (da) 2006-12-27
JP2002527601A (ja) 2002-08-27
DE59913914D1 (de) 2006-11-23
CA2347039A1 (fr) 2000-04-27
NO20011927D0 (no) 2001-04-19
CA2347039C (fr) 2008-05-06
JP4603692B2 (ja) 2010-12-22
EP1124916A1 (fr) 2001-08-22
KR100693848B1 (ko) 2007-03-13
DE19848621A1 (de) 2000-04-27
ES2275357T3 (es) 2007-06-01
KR20010099703A (ko) 2001-11-09
WO2000023541A1 (fr) 2000-04-27
US6786940B1 (en) 2004-09-07
NO329079B1 (no) 2010-08-16

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