EP1801188B1 - Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant - Google Patents

Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant Download PDF

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Publication number
EP1801188B1
EP1801188B1 EP07005871A EP07005871A EP1801188B1 EP 1801188 B1 EP1801188 B1 EP 1801188B1 EP 07005871 A EP07005871 A EP 07005871A EP 07005871 A EP07005871 A EP 07005871A EP 1801188 B1 EP1801188 B1 EP 1801188B1
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alkyl
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EP07005871A
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German (de)
English (en)
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EP1801188A3 (fr
EP1801188A2 (fr
Inventor
Matthias Krull
Werner Reimann
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Clariant Produkte Deutschland GmbH
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Clariant Produkte Deutschland GmbH
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    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)

Definitions

  • the present invention relates to mixtures of fatty acids and paraffin dispersants having improved low-temperature stability, and to their use for improving the lubricity of middle distillate fuel oils.
  • Mineral oils and mineral oil distillates used as fuel oils generally contain 0.5% by weight and more sulfur which causes the formation of sulfur dioxide upon combustion. In order to reduce the resulting environmental impact, the sulfur content of fuel oils is lowered further and further.
  • the standard EN 590 relating to diesel fuels currently prescribes a maximum sulfur content of 350 ppm in Germany. In Scandinavia fuel oils of less than 50 ppm and in exceptional cases less than 10 ppm of sulfur are used. These fuel oils are usually prepared by hydrogenating the fractions obtained from the petroleum by distillation. In the desulfurization but other substances are removed, which give the fuel oils a natural lubricating effect. These substances include polyaromatic and polar compounds.
  • EP-A-0 798 364 discloses salts and amides of mono- to tetracarboxylic acids having 2 to 50 carbon atoms and aliphatic mono- / polyamines having 2 to 50 carbon atoms and 1 to 10 N atoms as lubricity additives for low-sulfur diesel fuel.
  • Preferred amines have 8-20 C-atoms, such as coco fatty amine, tallow fatty amine and oleylamine.
  • WO 95/33805 discloses the use of cold flow improvers to improve the lubricity of low sulfur middle distillates.
  • polar nitrogen-containing compounds which contain a group NR 13 , where R 13 is a hydrocarbon radical having 8 to 40 C atoms and may be present in the form of a cation.
  • WO-A-96/18706 disclosed in analogy to WO 95/33805 the use of the nitrogen-containing compounds mentioned therein in combination with lubricity additives.
  • WO-A-96/23855 disclosed in analogy to WO 95/33805 the use of the nitrogen-containing compounds mentioned therein in combination with detergent additives.
  • the fatty acids used in the prior art have the disadvantage that they solidify when stored at low temperatures, ie often at room temperature, usually at temperatures of 0 ° C at -5 ° C at the latest, or that deposit crystalline particles and problems prepare handling. This problem can only be partially solved by dilution with organic solvents, since components also crystallize out of these solutions or the solution gels and solidifies. For use as lubricity additives, they therefore have to be diluted considerably, or kept in heated storage containers and metered via heated lines.
  • the object underlying the present invention was to find lubricity additives which improve the lubricating effect of middle distillates at reduced metering rates, but remain homogeneous, clear and, in particular, free-flowing even in the cold.
  • Another object of the invention are cold-stabilized solutions of additives according to the invention in organic solvents, wherein the solutions contain 1 to 90 wt .-% of solvent.
  • Suitable solvents are aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures.
  • the additives according to the invention preferably contain 1 to 80%, especially 10 to 70%, in particular 25 to 60%, of solvent.
  • the cold-stabilized solutions according to the invention have an own pour point of less than -40 ° C., preferably -45 ° C. especially -50 ° C.
  • Another object of the invention is the use of said mixtures of the components A and B to improve the lubricating properties of low-sulfur middle distillates with up to 0.05 wt .-% sulfur content.
  • Preferred fatty acids are those having 8-40 C atoms, in particular 12-22 C atoms.
  • the alkyl radicals of the fatty acids consist essentially of carbon and hydrogen. However, they may contain other substituents, e.g. Hydroxyl, halogen, amino or nitro groups, provided they do not affect the predominantly hydrocarbon character.
  • Component A2) may contain one or more double bonds and be of natural or synthetic origin. In the case of polyunsaturated carboxylic acids, their double bonds may be isolated or else conjugated.
  • the proportion of saturated fatty acids A1) in the mixture of A1) and A2) is preferably below 20% by weight, in particular below 10% by weight, especially below 5% by weight.
  • preferred fatty acid mixtures which is understood here as the combination of A1) and A2), at least 50% by weight, in particular at least 75% by weight, especially at least 90% by weight, of the constituents contain one or more double bonds.
  • These preferred fatty acid (mixtures) have iodine numbers of at least 40 g l / 100 g, preferably at least 80 g l / 100 g, in particular at least 125 g l / 100 g.
  • Suitable fatty acids are, for example, lauric, tridecane, myristic, pentadecane, palmitic, margarine, stearic, isostearic, arachic and behenic acid, oleic and erucic acid, palmitoleic, myristoleic, linoleic, linolenic, elaeosterol - and Arachidonic acid, ricinoleic acid and derived from natural fats and oils fatty acid mixtures, such as coconut oil, peanut oil, fish, linseed oil, palm oil, rapeseed oil, ricinoleic, castor oil, rapeseed oil, soybean oil, sunflower oil and tall oil fatty acid.
  • natural fats and oils fatty acid mixtures such as coconut oil, peanut oil, fish, linseed oil, palm oil, rapeseed oil, ricinoleic, castor oil, rapeseed oil, soybean oil, sunflower oil and tall
  • dicarboxylic acids such as dimer fatty acids and alkyl- and alkenylsuccinic acids with C 8 -C 50 -alk (en) yl radicals, preferably with C 8 -C 40 -, in particular with C 12 -C 22 -alkyl radicals.
  • the alkyl radicals can be linear or branched (oligomerized alkenes, PIB).
  • the fatty acids may further contain 1-40, especially 1-25% by weight of resin acids, based on the weight of A1) and A2) together.
  • the additives according to the invention comprise, as constituent B, at least one polar nitrogen-containing compound of formulas 5 or 6 which is effective as paraffin dispersant in middle distillates.
  • the amides or ammonium amides or ammonium salts e.g. Nitrilotriacetic acid, ethylenediaminetetraacetic acid or propylene-1,2-diaminetetraacetic acid are obtained by reacting the acids with 0.5 to 1.5 moles of amine, preferably 0.8 to 1.2 moles of amine per carboxyl group.
  • the reaction temperatures are about 80 to 200 ° C, wherein for the preparation of the amides a continuous removal of the resulting water of reaction takes place. However, 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.
  • the compounds mentioned under B1) can also be prepared.
  • dialkylamines are those in which R 6 , R 7 is a straight-chain alkyl radical having 10 to 30 carbon atoms, preferably 14 to 24 Carbon atoms, means.
  • R 6 , R 7 is a straight-chain alkyl radical having 10 to 30 carbon atoms, preferably 14 to 24 Carbon atoms, means.
  • dioleylamine, dipalmitinamine, dicoco fatty amine and dibehenylamine and preferably ditallow fatty amine may be mentioned.
  • Paraffin dispersants reduce the size of paraffin crystals precipitated in the cold and cause the paraffin particles not to settle but to remain colloidally dispersed with significantly reduced sedimentation effort.
  • oil-soluble polar compounds having ionic or polar groups e.g. Amine salts and / or amides proven to be obtained by reaction of aliphatic or aromatic amines, preferably long-chain aliphatic amines, with aliphatic or aromatic mono-, di-, tri- or tetracarboxylic acids or their anhydrides.
  • paraffin dispersants contain reaction products of secondary fatty amines having 8 to 36 carbon atoms, in particular dicoco fatty amine, ditallow fatty amine and distearylamine.
  • Other paraffin dispersants are copolymers of maleic anhydride and ⁇ , ⁇ -unsaturated compounds which can optionally be reacted with primary monoalkylamines and / or aliphatic alcohols, the reaction products of alkenyl spiro-bis-lactones with amines and reaction products of terpolymers based on ⁇ , ⁇ -unsaturated dicarboxylic acid anhydrides, ⁇ , ⁇ -unsaturated compounds and polyoxyalkylene ethers of lower unsaturated alcohols.
  • Alkylphenol-formaldehyde resins are also suitable as paraffin dispersants. In the following, some suitable paraffin dispersants are listed.
  • the mixing ratio between A and B can vary within wide limits. Thus, even small amounts of B from 100 ppm to 50,000 ppm, preferably 1,000 ppm to 10,000 ppm, in fatty acid solutions as a cold additive for A. They are able to prevent self-crystallization of the fatty acid, which leads to a lowering of the cloud point, or sedimentation Prevent formed crystals and thus allow easy handling at reduced temperatures. However, for specific problem solutions, from 5% up to 50%, in special cases up to 90% of constituent B, based on the amount of constituent A, may also be present. In particular, the self-sticking point of the additive is lowered and the lubricity of the additized oil is improved. Accordingly, the preferred mixing ratio of A: B is between 1:10 and 1: 0.0001, more preferably between 1: 4 and 1: 0.0005, especially between 1: 1 and 1: 0.001.
  • the additives according to the invention are added to oils in amounts of from 0.001 to 0.5% by weight, preferably from 0.001 to 0.1% by weight. They may be used as such or dissolved in solvents, such as aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures such as toluene, xylene, ethylbenzene, decane, pentadecane, gasoline fractions, kerosene or commercial solvent mixtures such as Solvent Naphtha, ® Shellsol AB, ® Solvesso 150 , ® Solvesso 200, ® Exxsol, ® Isopar and ® Shellsol D types.
  • solvents such as aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures such as toluene, xylene, ethylbenzene, decane, pentadecane, gasoline fractions, kerosene or commercial solvent mixtures such as Solvent Naphtha, ® Shellsol
  • the additives according to the invention preferably contain 1 to 80%, especially 10 to 70%, in particular 25 to 60%, of solvent.
  • the additives which can be used without problems even at low temperatures of, for example, -40 ° C and lower, improve the lubricity of the additized oils and their cold and corrosion protection properties.
  • the additives according to the invention can also be used together with one or more oil-soluble co-additives, which in themselves improve the cold flow properties and / or lubricity of crude oils, lubricating oils or fuel oils.
  • oil-soluble co-additives are vinyl acetate-containing copolymers or terpolymers of ethylene, comb polymers, alkylphenol-aldehyde resins and oil-soluble amphiphiles.
  • the additives according to the invention are used in admixture with ethylene / vinyl acetate / vinyl neononanoate terpolymers or ethylene / vinyl acetate / vinyl neodecanoate terpolymers to improve the flowability of mineral oils or mineral oil distillates.
  • the terpolymers of vinyl neononanoate or vinyl neodecanoate contain, in addition to ethylene, 10 to 35% by weight of vinyl acetate and 1 to 25% by weight of the respective neo compound.
  • copolymers contain, in addition to ethylene and from 10 to 35% by weight of vinyl esters, from 0.5 to 20% by weight of olefin, such as diisobutylene, 4-methylpentene or norbornene.
  • olefin such as diisobutylene, 4-methylpentene or norbornene.
  • the mixing ratio of the additives according to the invention with the ethylene vinyl acetate copolymers described above or the terpolymers of ethylene, vinyl acetate and the vinyl esters of neononanic or neodecanoic acid is (in parts by weight) 20: 1 to 1:20, preferably 10: 1 to 1: 10th
  • these alkylphenol-formaldehyde resins are those of the formula wherein R 50 is C 4 -C 50 alkyl or alkenyl, R 51 is ethoxy and / or propoxy, n is a number from 5 to 100 and p is a number from 0 to 50.
  • the additives according to the invention are used together with comb polymers.
  • This term refers to polymers in which hydrocarbon radicals having at least 8, in particular at least 10, carbon atoms are bonded to a polymer backbone.
  • they are homopolymers whose alkyl side chains contain at least 8 and in particular at least 10 carbon atoms.
  • at least 20%, preferably at least 30% of the monomers have side chains (cf. Comb-like Polymers-Structure and Properties; NA Platé and VP Shibaev, J. Polym. Sci. Macromolecular Revs. 1974, 8, 117 ff ).
  • Suitable comb polymers are, for example, fumarate / vinyl acetate copolymers (cf. EP 0 153 176 A1 ), Copolymers of a C 6 -C 24 - ⁇ -olefin and a NC 6 -C 22 -alkylmaleimide (cf. EP 0 320 766 Further, esterified olefin / maleic anhydride copolymers, polymers and copolymers of ⁇ -olefins and esterified copolymers of styrene and maleic anhydride.
  • the additives according to the invention are suitable for improving the lubricating properties of animal, vegetable, mineral or synthetic fuel oils with only low dosing rates. Due to their improved cold properties can be dispensed with storage and application to a warming and / or dilution. In addition, they simultaneously improve the cold and corrosion protection properties of the additized oils. The emulsifying properties of the additized oils are less affected than is the case with the lubricating additives of the prior art.
  • the additives of the invention are particularly well suited for use in middle distillates. As middle distillates are in particular those mineral oils which are obtained by distillation of crude oil and boil in the range of 120 to 450 ° C, for example kerosene, jet fuel, diesel and fuel oil.
  • the oils can also be alcohols such as methanol and / or contain or consist of ethanol.
  • the additives of the invention are used in middle distillates containing 0.05% by weight of sulfur and less, more preferably less than 350 ppm of sulfur, more preferably less than 200 ppm of sulfur and in special cases less than 50 ppm of sulfur. These are generally those middle distillates that have been subjected to a hydrogenating refining, and therefore contain only small amounts of polyaromatic and polar compounds that give them a natural lubricating effect.
  • the additives according to the invention are furthermore preferably used in middle distillates which have 95% distillation points below 370.degree. C., in particular 350.degree. C. and in special cases below 330.degree. They can also be used as components in lubricating oils.
  • the mixtures can be used alone or together with other additives, e.g. with other pour point depressants or dewaxing aids, with corrosion inhibitors, antioxidants, sludge inhibitors, dehazers, conductivity improvers, lubricity additives, and cloud point depressant additives. Furthermore, they are successfully used in conjunction with additive packages, which i.a. known ashless dispersing additives, detergents, defoamers and corrosion inhibitors.
  • Table 1 Own point (pour point) of the additives of the invention Composition (parts by weight) Pour point example A1 A2 B1 B2 B3 B4 V1 80 20 -9 V2 50 50 -24 V3 20 80 0 V4 80 20 -9 V5 50 50 -24 V6 20 80 -6 V7 80 20 0 V8 50 50 -15 V9 20 80 -48 V10 80 20 -9 V11 50 50 -18 V12 20 80 -15 V13 80 20 -27 V14 50 50 -27 V15 20 80 -6 V16 80 20 -27 V17 50 50 -54 V18 20 80 -45 V19 80 20 -21 V20 50 50 -30 V21 20 80 -21 V22 80 20 -21 V23 50 50 -21 V24 20 80 -9 V25 * 99.95 0.05 -36 V26 * 99.95 0.05 -36 V27 99.95 0.05 -15 V28 100 -9 V29 100 6 V30 100 9 V31 100 -12 V32 100 0 V33 100 -6 V34 * 100 -36 * These examples
  • MS is a mixture of a number of aliphatic and cyclic non-aromatic hydrocarbons.
  • the main components of MS can be found in the following table: Table 6: Components of MS component Concentration range (% by weight) Di-2-ethylhexyl 10 - 25 2-ethylhexyl acid-2-ethylhexyl 10 - 25 C 16 lactones 4 - 20 2-Ethylhexylbutyrat 3 - 10 2-ethylhexanediol- (1,3) glycol mono-n-butyrate 5 - 15 2-ethylhexanol 4 - 10 C 4 to C 8 acetates 2 - 10 2-ethylhexanediol- (1,3) 2 - 5 Ethers and esters ⁇ C 20 0 - 20
  • the lubricating effect of the additives was carried out using an HFRR instrument from PCS Instruments on additized oils at 60 ° C.
  • the High Frequency Reciprocating Rig Test (HFRR) is described in D. Wei, H. Spikes, Wear, Vol. 111, No.2, p.217, 1986 , The results are given as coefficient of friction and Wear Scar (WS1.4). A low coefficient of friction and a low Wear Scar show a good lubricating effect.
  • test oils having the following characteristics were used: Test oil 1 Test oil 2 boiling range: 170 - 344 ° C 182-304 ° C density 0.830 g / cm 3 0.821 g / cm 3 Cloud point -9 ° C -33 ° C sulfur content 45 ppm 6 ppm

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Claims (10)

  1. Additifs stabilisés au froid pour carburants présentant une teneur en soufre jusqu'à 0,05% en poids, contenant des mélanges d'acides gras constitués par
    A1) 1 à 99% en poids d'au moins un acide monocarboxylique ou dicarboxylique saturé comprenant 6 à 50 atomes de carbone,
    A2) 1 à 99% en poids d'au moins un acide monocarboxylique ou dicarboxylique insaturé comprenant 6 à 50 atomes de carbone,
    ainsi que
    B) au moins un composé azoté polaire actif comme dispersant de paraffines dans les distillats moyens en une quantité de 0, out à 90% en poids par rapport au poids total de A1) , A2) et B), qui est un amide ou un sel d'ammonium d'acides aminoalkylènepolycarboxyliques avec des amines secondaires des formules 5 et 6
    Figure imgb0043
    Figure imgb0044
     dans lesquelles
    R10 signifie un radical alkylène linéaire ou ramifié comprenant 2 à 6 atomes de carbone ou le radical de formule 7
    Figure imgb0045
     où les structures amides peuvent également se trouver, partiellement ou complètement, sous forme de la structure de sel d'ammonium de formule 8
    Figure imgb0046
     et
    R6 et R7 peuvent être identiques ou différents et au moins un de ces groupes représente C8-C36-alkyle, C6-C36-cycloalkyle, C6-C36-alcényle, et l'autre groupe signifie hydrogène, C1-C36-alkyle, C2-C36-alcényle, cyclohexyle, ou un groupe des formules -(A-O)x-E ou - (CH2)n-NYZ, où A représente un groupe éthylène ou propylène, x un nombre de 1 à 50, E = H, C1-C30-alkyle, C5-C12-cycloalkyle ou C6-C30-aryle, et n vaut 2, 3 ou 4, et Y et Z signifient, indépendamment l'un de l'autre H, C1-C30-alkyle ou - (A-O)x-H.
  2. Additifs selon la revendication 1, où le constituant A comprend des acides carboxyliques comprenant 12 à 22 atomes de carbone
  3. Additifs selon la revendication 1 et/ou 2, contenant 1 à moins de 20% en poids de A1) et plus de 80 à 99% en poids de A2).
  4. Additifs selon l'une ou plusieurs des revendications 1 à 3, où le mélange de A1) et de A2) présente un indice d'iode d'au moins 40 g I/100 g.
  5. Additifs selon l'une ou plusieurs des revendications 1 à 4, où le mélange de A1) et de A2) comprend 1 à 40% en poids d'acides de résine.
  6. Solutions stabilisées au froid des additifs selon l'une ou plusieurs des revendications 1 à 5 dans des solvants organiques, les solvants contenant 1 à 80% en poids de solvant.
  7. Solutions stabilisées au froid selon la revendication 6, où on utilise comme solvant des hydrocarbures aliphatiques et/ou aromatiques et/ou oxygénés.
  8. Mélanges d'acides gras stabilisés au froid, contenant
    A1) 1 à 99% en poids d'au moins un acide monocarboxylique ou dicarboxylique saturé comprenant 6 à 50 atomes de carbone,
    A2) 1 à 99% en poids d'au moins un acide monocarboxylique ou dicarboxylique insaturé comprenant 6 à 50 atomes de carbone,
    ainsi que
    B) au moins un composé azoté polaire actif comme dispersant de paraffines dans les distillats moyens, tel qu'indiqué comme constituant B) dans la revendication 1, en une quantité de 0,01 à 90% en poids par rapport au poids total de A1), A2) et B) .
  9. Carburants, contenant, outre un distillat moyen présentant une teneur en soufre jusqu'à 0,05% en poids, un additif selon l'une ou plusieurs des revendications 1 à 8.
  10. Utilisation d'additifs selon l'une ou plusieurs des revendications 1 à 8 pour améliorer les propriétés lubrifiantes de distillats moyens pauvres en soufre présentant une teneur en soufre jusqu'à 0,05% en poids.
EP07005871A 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant Expired - Lifetime EP1801188B1 (fr)

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EP01126254A EP1209215B1 (fr) 2000-11-24 2001-11-06 Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant

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EP01126254A Expired - Lifetime EP1209215B1 (fr) 2000-11-24 2001-11-06 Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant
EP07005871A Expired - Lifetime EP1801188B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant

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US6610111B2 (en) 2003-08-26
EP1801188A3 (fr) 2007-10-03
DE50114718D1 (de) 2009-04-02
EP1803791A3 (fr) 2007-10-03
EP1209215A2 (fr) 2002-05-29
US20020095857A1 (en) 2002-07-25
EP1803791B1 (fr) 2009-02-18
EP1209215A3 (fr) 2003-08-13
EP1209215B1 (fr) 2007-10-10
DE50113115D1 (de) 2007-11-22
EP1801188A2 (fr) 2007-06-27
DE10058359B4 (de) 2005-12-22
CA2363700A1 (fr) 2002-05-24
CA2363700C (fr) 2010-04-06
JP5317380B2 (ja) 2013-10-16
US20040083644A1 (en) 2004-05-06
JP2002167586A (ja) 2002-06-11
DE50114719D1 (de) 2009-04-02
DE10058359A1 (de) 2002-06-06
USRE40758E1 (en) 2009-06-23
EP1803791A2 (fr) 2007-07-04
ES2295098T3 (es) 2008-04-16

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