EP1801188A2 - Huiles combustibles ayant une action lubrifiante améliorée, comprenant des mélanges d'acides gras avec émulsifiants de paraffine, tout comme un additif améliorant la lubrification - Google Patents

Huiles combustibles ayant une action lubrifiante améliorée, comprenant des mélanges d'acides gras avec émulsifiants de paraffine, tout comme un additif améliorant la lubrification Download PDF

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Publication number
EP1801188A2
EP1801188A2 EP07005871A EP07005871A EP1801188A2 EP 1801188 A2 EP1801188 A2 EP 1801188A2 EP 07005871 A EP07005871 A EP 07005871A EP 07005871 A EP07005871 A EP 07005871A EP 1801188 A2 EP1801188 A2 EP 1801188A2
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Prior art keywords
alkyl
und
oder
bis
der
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EP07005871A
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German (de)
English (en)
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EP1801188A3 (fr
EP1801188B1 (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 the additives of 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 below -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 carry other substituents such as hydroxy, halogen, amino or nitro groups, if these do not affect the predominant 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 to mean 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, ricinine, castor oil, rapeseed oil, soybean oil, sunflower oil and tall oil fatty acid.
  • 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 contain as component B at least one polar nitrogen-containing compound which is effective as paraffin dispersant in middle distillates.
  • Paraffin dispersants reduce the size of the paraffin crystals precipitated in the cold and cause the paraffin particles not to settle, but instead colloidally with significantly reduced tendency to sediment, remain dispersed.
  • Suitable paraffin dispersants are oil-soluble polar compounds having ionic or polar groups, eg amine salts and / or amides, which are prepared 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 are obtained.
  • 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. Even small amounts B of 100 ppm to 50,000 ppm, preferably 1,000 ppm to 10,000 ppm, in fatty acid solutions act as a cold additive for A. They are able to prevent the 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 are used.
  • 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, ® Shell
  • 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 1:10.
  • 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 may also contain or consist of alcohols such as methanol and / or ethanol.
  • the additives according to the invention are used in middle distillates containing 0.05% by weight of sulfur and less, more preferably less than 350 ppm of sulfur, in particular 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 1 80 20 -9 2 50 50 -24 3 20 80 0 4 80 20 -9 5 50 50 -24 6 20 80 -6 7 80 20 0 8th 50 50 -15 9 20 80 -48 10 80 20 -9 11 50 50 -18 12 20 80 -15 13 80 20 -27 14 50 50 -27 15 20 80 -6 16 80 20 -27 17 50 50 -54 18 20 80 -45 19 80 20 -21 20 50 50 -30 21 20 80 -21 22 80 20 -21 23 50 50 -21 24 20 80 -9 25 * 99.95 0.05 -36 26 * 99.95 0.05 -36 27 99.95 0.05 -15 V1 100 -9 V2 100 6 V3 100 9 V4 100 -12 V5 100 0 V6 100 -6 V7 * 100 -36 * These examples are obtained with a 50% by weight adjustment of the fatty acid in solvent naphtha.
  • Composition (parts by weight) Cloud point example A1 A2 B1 B2 B3 B4 V8 * 100 -27.0 28 * 99.9995 0.0005 -33.0 29 * 99.9995 0.0005 -30.5 30 * 99,998 0,002 -33.5 31 * 99,998 0,002 -33.5 32 * 99.995 0.005 -31.0 33 * 99.995 0.005 -32.2 34 ** (B5) 99,998 0,002 -29.0 35 ** (B6) 99,998 0,002 -31.0 36 ** (B7) 99,998 0,002 -35.5 37 ** (B8) 99,998 0,002 -37.0 * These examples were obtained with a 50% by weight adjustment of the fatty acid in solvent naphtha.
  • 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 (wt%) 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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  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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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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DE10058359A DE10058359B4 (de) 2000-11-24 2000-11-24 Brennstofföle mit verbesserter Schmierwirkung, enthaltend Mischungen aus Fettsäuren mit Paraffindispergatoren, sowie ein schmierverbesserndes Additiv
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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EP07005870A Revoked EP1803791B1 (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
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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EP07005870A Revoked EP1803791B1 (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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EP1803791A3 (fr) 2007-10-03
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USRE40758E1 (en) 2009-06-23
EP1209215A3 (fr) 2003-08-13
EP1803791B1 (fr) 2009-02-18
US20040083644A1 (en) 2004-05-06
EP1801188A3 (fr) 2007-10-03
JP2002167586A (ja) 2002-06-11
EP1801188B1 (fr) 2009-02-18
CA2363700C (fr) 2010-04-06
ES2295098T3 (es) 2008-04-16
DE10058359B4 (de) 2005-12-22
DE50114719D1 (de) 2009-04-02
CA2363700A1 (fr) 2002-05-24
US20020095857A1 (en) 2002-07-25
DE50114718D1 (de) 2009-04-02
EP1803791A2 (fr) 2007-07-04
DE10058359A1 (de) 2002-06-06
EP1209215B1 (fr) 2007-10-10
JP5317380B2 (ja) 2013-10-16
EP1209215A2 (fr) 2002-05-29

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