EP2417229B1 - Mélange de composés azotés polaires solubles dans l'huile et de composés aliphatiques solubles dans l'huile servant à abaisser le cloud point dans les carburants diesel - Google Patents

Mélange de composés azotés polaires solubles dans l'huile et de composés aliphatiques solubles dans l'huile servant à abaisser le cloud point dans les carburants diesel Download PDF

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EP2417229B1
EP2417229B1 EP10711676.6A EP10711676A EP2417229B1 EP 2417229 B1 EP2417229 B1 EP 2417229B1 EP 10711676 A EP10711676 A EP 10711676A EP 2417229 B1 EP2417229 B1 EP 2417229B1
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acid
oil
weight
middle distillate
carbon atoms
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EP2417229A1 (fr
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Frank-Olaf Mähling
Jan Strittmatter
Heinrich Lubojanski
Andreas Minke
Uwe Rebholz
Alex J. Attlesey
Stephan B. Lopes Ii
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BASF SE
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BASF SE
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    • 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
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • 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
    • C10L1/16—Hydrocarbons
    • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
    • 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
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
    • 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
    • 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

Definitions

  • the present invention relates to a specific mixture of such components (A), (B1) and (B2) and inert diluent containing a proportion of certain alkanols, phenols and / or carboxylic acid esters, and the use of this particular mixture as a component of additive concentrates for middle distillate fuels.
  • Middle distillate fuels of fossil origin especially gas oils, diesel oils or light fuel oils derived from petroleum
  • the cloud point or cloud point (“CP") causes the beginning of solid paraffin excretion, which consists predominantly or exclusively of n-paraffins.
  • the platy n-paraffin crystals form a kind of "house of cards structure" and the middle distillate fuel stagnates, although its predominant part is still liquid.
  • ethylene-vinyl carboxylate copolymers have long been used as cold flow improvers or Middle Distillate Flow Improvers ("MDFI").
  • MDFI Middle Distillate 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 fuel or fuel usually takes place only 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.
  • Cloud Point Depressants can extend the temperature range, where middle distillate fuels can be used easily, to lower temperatures.
  • a mixture of 5 to 95% by weight of at least one polar oil-soluble nitrogen compound capable of adequately dispersing cold-precipitated paraffin crystals in fuels is 1 to 50% by weight of at least one oil-soluble polyamines acid amide with 2 to 1000 nitrogen atoms and C 8 - to C 30 -fatty acids or fatty acid-analogous compounds containing free carboxyl groups and 0 to 50 wt .-% of at least one oil-soluble reaction product of ⁇ , ⁇ -dicarboxylic acids having 4 to 300 carbon atoms or their derivatives and primary alkylamines, and the use of this mixture as an additive to fuels for improving the cold flow behavior, in particular in the function as paraffin dispersant described.
  • Examples of polar oil-soluble nitrogen compounds in (1) are the reaction products of 1 mole of ethylenediaminetetraacetic acid and 4 moles of hydrogenated ditallow fatty amine, the reaction product of 1 mole of phthalic anhydride and 2 moles of hydrogenated or unhydrogenated ditallow fatty amine or the reaction product of 1 mole of alkenyl spirobislactone with 2 moles of hydrogenated or not called hydrogenated ditallow fatty amine.
  • the mixture described in (1) may be added to the fuel neat or in a hydrocarbon solvent.
  • Cold-stabilized fuel oil compositions containing cold flow improvers detergent additives and cold stabilizers are known.
  • a low-temperature stabilizer especially the half-amide of maleic acid and tridecylamine is recommended.
  • these low-temperature stabilization boosters reduce the CFPP value and / or CP value raised or no longer sufficiently lowered by the detergents.
  • reaction products of 1 mole of ethylenediaminetetraacetic acid and 4 moles of hydrogenated Ditalgfettamin, the reaction product of 1 mole of phthalic anhydride and 2 moles of hydrogenated or non-hydrogenated Ditalgfettamin or the reaction product of 1 mole of alkenyl spirobislactone with 2 moles of hydrogenated or non-hydrogenated Ditalgfettamin called.
  • the fuel oil compositions described in (2) may contain, among other common co-additives, inter alia unspecified solubilizers.
  • WO 03/042336 (3) describes mixtures of an ester of an alkoxylated polyol and a polar nitrogen-containing paraffin dispersant, for example a reaction product of an alkenyl spiro-bis-lactone with an amine, an amide or ammonium salt of an aminoalkylene polycarboxylic acid such as ethylenediaminetetraacetic acid or nitrilotriacetic acid or an amide of a dicarboxylic acid such as phthalic acid, as additives for low sulfur mineral oil distillates , Solubilizers such as 2-ethylhexanol, decanol, iso-decanol or iso-tridecanol can be added to these mixtures.
  • a polar nitrogen-containing paraffin dispersant for example a reaction product of an alkenyl spiro-bis-lactone with an amine, an amide or ammonium salt of an aminoalkylene polycarboxylic acid such as ethylenediaminet
  • the EP-A 0 413 279 (5) discloses the use of an oil-soluble polar nitrogen compound, which is obtainable from 1 mole dodecenyl spirolactone and 2 moles tallow fatty or ditallow fatty amine in middle distillate fuels to lower the cloud point while at the same time reducing the cold filter plugging point lowering response the addition of cold flow improvers.
  • the object was to provide products as more efficient cloud point depressants, which have an improved cold flowability behavior of such middle distillate fuels, which already have a relatively low CP value of -8.0 ° C. or lower before the addition of additives, by lowering the cloud point ("CP"), determined in the non-sedimented middle distillate fuel, at standard dosing rates efficiently, ie by at least 1.5 ° C, over the non-additive fuel, without at the same time reducing the response to Lowering the Cold Filter Plugging Point ("CFPP”) with the addition of cold flow improvers deteriorate, as is the case with the known from the prior art Cloud Point depressants - as well as those described in document (4) - usually the case.
  • CP cloud point
  • CFPP Cold Filter Plugging Point
  • the object is achieved by the above-defined use of the mixture comprising the components (A), (B1) and (B2).
  • the CP value in the middle distillate fuel is at least 1.8 ° C, especially at least 2.3 ° C, especially at least 2.6 ° C, compared with the non-additive middle distillate fuel at a dosage of the mixture in the range of 150 to 250 ppm by weight, each determined in the non-sedimented middle distillate fuel lowered, the response for lowering the CFPP value at previous or subsequent addition of cold flow improvers such as conventional MDFI, for example ethylene-vinyl carboxylate copolymers, not only does not deteriorate but is generally improved over the middle distillate fuel containing only the cold flow improvers, usually by further lowering the CFPP Values at least 2 ° C, in particular at least 3 ° C, especially at least 4 ° C.
  • cold flow improvers such as conventional MDFI, for example ethylene-vinyl carboxylate copolymers
  • the present invention does not -sediment mandat total middle distillate fuel, the measurement of the application-relevant meaningful CP and CFPP values and thus indicates the relevant for refineries, for practical reasons upwards strictly limited CP values of the fuel.
  • Component (A) provides reaction products of dicarboxylic acids such as cyclohexane-1,2-dicarboxylic acid, cyclohexene-1,2-dicarboxylic acid, cyclopentane-1,2-dicarboxylic acid, naphthalenedicarboxylic acids such as naphthalene-1,2-dicarboxylic acid, naphthalene-1, 4-dicarboxylic acid, Naphthalene-1,5-dicarboxylic acid and naphthalene-1,8-dicarboxylic acid, phthalic acid, isophthalic acid, terephthalic acid and with long-chain hydrocarbon radicals such as octyl, 2-ethylhexyl, nonyl, isononyl, decyl, 2-propylheptyl, undecyl, dodecyl, tridecyl, Iso-tridecyl, tetradecyl, hexadec
  • the primary and secondary amines having at least 8 carbon atoms as respective reaction partners for the dicarboxylic acids to form the component (A) are usually monoamines, especially aliphatic monoamines. These primary and secondary amines may be selected from a variety of amines bearing hydrocarbon radicals, optionally linked together. In a preferred embodiment, these amines are secondary amines and have the general formula HNR 2 , in which the two variables R independently of one another in each case straight-chain or branched C 8 - to C 30 alkyl or alkenyl, in particular C 14 to C 24th Alkyl radicals, especially C 16 - to C 20 alkyl radicals, mean.
  • longer-chain alkyl or alkenyl radicals are preferably straight-chain or only slightly branched.
  • the abovementioned secondary amines are derived with respect to their longer-chain alkyl or alkenyl radicals from naturally occurring fatty acids or from their derivatives.
  • the two radicals R are the same.
  • Suitable primary amines are octylamine, 2-ethylhexylamine, nonylamine, decylamine, 2-propylheptyl, undecylamine, dodecylamine, tridecylamine, isotridecylamine, tetradecylamine, hexadecylamine, octadecylamine (stearylamine), oleylamine or behenylamine.
  • Suitable secondary amines are, for example, dioctadecylamine (distearylamine) and methylbehenylamine.
  • amine mixtures in particular industrially available amine mixtures such as fatty amines or hydrogenated or non-hydrogenated tallamines, for example hydrogenated or non-hydrogenated tallow fatty amine, as used, for example, in US Pat Ullmanns Encyclopedia of Industrial Chemistry, 6th edition, in the chapter “Amines, aliphatic " to be discribed.
  • the above-mentioned long-chain secondary amines such as distearylamine may also be used in free, i.e. not reacted with a carboxyl function, form part of mixtures suitable as additive concentrates for middle distillate fuels.
  • the component (A) may be mentioned the N, N-dialkylammonium salts of 2-N ', N'-dialkylamidobenzoates, for example the reaction product of 1 mole of phthalic anhydride and 2 moles of ditallow fatty amine, the latter being hydrogenated or unhydrogenated.
  • the oil-soluble polar nitrogen compounds (A) are amides, amide ammonium salts or ammonium salts in which none, one or more carboxylic acid groups have been converted to amide groups.
  • the abovementioned secondary amines can be bound to the dicarboxylic acids by means of amide structures or in the form of the ammonium salts, and only one part can be present as amide structures and another part as ammonium salts. Preferably, only a few or no free acid groups are present.
  • such reaction products of dicarboxylic acids with secondary amines are present as mixed amide ammonium salts.
  • the oil-soluble aliphatic compounds of component (B) are preferably based on aliphatic mono- or dicarboxylic acids as carboxylic acid components.
  • the dicarboxylic acids mentioned typically have an ⁇ , ⁇ structure with respect to the position of the two carboxyl functions.
  • Monoamines of component (B) may be based on primary or secondary monoamines having 1 to 30 carbon atoms whose hydrocarbon radicals are alkyl, alkenyl or cycloalkyl substituents.
  • component (B) may be based on those having 2 to 1000, in particular 2 to 500, in particular 2 to 100, nitrogen atoms in the molecule; Suitable hydrocarbon radicals and bridge members here are preferably corresponding alkyl and alkenyl or alkylene and alkenylene radicals. Alcohols may be based on aliphatic or cycloaliphatic mono-, di- or polyalcohols having 1 to 30 carbon atoms.
  • the oil-soluble aliphatic compounds of component (B) are thus usually carboxylic acid amides, Carbon
  • At least one building block in component (B) - be it the carboxylic acid, the amine or the alcohol unit - one or more straight-chain or branched alkyl or alkenyl chains having at least 8, especially 14, especially 16 carbon atoms exhibit.
  • the ⁇ , ⁇ -dicarboxylic acids on which the oil-soluble reaction products of component (B1) are based which have 4 to 300, in particular 4 to 75, especially 4 to 12 carbon atoms, are, for example, succinic acid, maleic acid, fumaric acid or derivatives thereof, those on the bridging ethylene or ethenylene group may have shorter or longer chain hydrocarbyl substituents which contain or may carry heteroatoms and / or functional groups.
  • succinic acid, maleic acid, fumaric acid or derivatives thereof those on the bridging ethylene or ethenylene group may have shorter or longer chain hydrocarbyl substituents which contain or may carry heteroatoms and / or functional groups.
  • succinic acid maleic acid, fumaric acid or derivatives thereof, those on the bridging ethylene or ethenylene group
  • those on the bridging ethylene or ethenylene group may have shorter or longer chain hydrocarbyl substituents which contain or may carry heteroatoms
  • the oil-soluble aliphatic compound (B1) is a reaction product of maleic anhydride and primary C 9 - to C 15 -alkylamines.
  • the primary alkylamines on which the oil-soluble reaction products of component (B1) are based are usually medium-chain or long-chain alkyl or alkenyl monoamines having preferably 8 to 30, in particular 8 to 22, especially 9 to 15 Carbon atoms and linear or branched, saturated or unsaturated aliphatic hydrocarbon chain, for example octyl, nonyl, iso-nonyl, decyl, undecyl, tridecyl, iso-tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, Octadecyl- or oleylamine and mixtures of such amines.
  • medium-chain or long-chain alkyl or alkenyl monoamines having preferably 8 to 30, in particular 8 to 22, especially 9 to 15 Carbon atoms and linear or branched, saturated or unsaturated aliphatic hydrocarbon chain, for example octyl, nony
  • reaction products of component (B1) are usually present - depending on the stoichiometry and reaction regime - as semi- or bisamides of the dicarboxylic acid; they may also contain minor amount of corresponding ammonium salts.
  • a typical example of an oil-soluble reaction product of component (B1) is the reaction product of 1 mol of maleic anhydride with 1 mol of isotridecylamine, which is present predominantly as a half-amide of maleic acid.
  • the polyamines on which the oil-soluble acid amides of component (B2) are based can either be structurally clearly defined low molecular weight "oligo" amines or polymers having up to 1000, in particular up to 500, especially up to 100, nitrogen atoms in the macromolecule.
  • oligo low molecular weight
  • the latter are then usually polyalkyleneimines, for example polyethyleneimines, or polyvinylamines.
  • the polyamines mentioned are reacted with C 8 - to C 30 -fatty acids, in particular C 16 - to C 20 -fatty acids, or fatty acid-analogous compounds containing free carboxyl groups to the oil-soluble acid amides (B2).
  • C 8 - to C 30 -fatty acids in particular C 16 - to C 20 -fatty acids, or fatty acid-analogous compounds containing free carboxyl groups to the oil-soluble acid amides (B2).
  • B2 oil-soluble acid amides
  • reaction of the polyamines with the fatty acid to form the oil-soluble acid amides of component (B2) takes place completely or partially.
  • subordinate fractions of the product are usually present in the form of corresponding ammonium salts.
  • the completeness of the conversion to the acid amides can generally be controlled by the reaction parameters.
  • Suitable polyamines for the conversion to the acid amides of component (B2) are, for example: ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, dipropylenetriamine, tripropylenetetramine, tetrapropylenepentamine, pentapropylenhexamine, polyethyleneimines having an average degree of polymerization (corresponding to the number of nitrogen atoms) of, for example, , B. 10, 35, 50 or 100 and polyamines, which were obtained by reaction of oligoamines (with chain extension) with acrylonitrile and subsequent hydrogenation, for. N, N'-bis (3-aminopropyl) ethylenediamine.
  • Suitable fatty acids for the conversion to the acid amides of component (B2) are pure fatty acids and technically customary fatty acid mixtures which contain, for example, stearic acid, palmitic acid, lauric acid, oleic acid, linoleic acid and / or linolenic acid.
  • Naturally occurring fatty acid mixtures for example tallow fatty acid, coconut oil fatty acid, trans fatty acid, coconut oil fatty acid, soybean oil fatty acid, rapeseed oil fatty acid, peanut oil fatty acid or palm oil fatty acid, which contain oleic acid and palmitic acid as main components.
  • fatty acid analogues containing free carboxyl groups which are also suitable for reaction with said polyamines to the acid amides of component (B2) are monoesters of long-chain alcohols of dicarboxylic acids such as tallow fatty alcohol maleic acid half-ester or tallow fatty alcohol succinic acid half ester or corresponding glutaric or adipic acid half-esters.
  • the oil-soluble aliphatic compound (B2) is an oil-soluble acid amide of aliphatic polyamines having 2 to 6 nitrogen atoms and C 16 to C 20 fatty acids, all of the primary and secondary amino functions of the polyamines being converted to acid amide functions.
  • a typical example of an oil-soluble acid amide of component (B2) is the reaction product of 3 moles of oleic acid with 1 mole of diethylenetriamine.
  • the mixture used according to the invention comprises as additional component at least one inert polar diluent (C) selected from C 8 - to C 30 -alkanols, aryl-substituted C 1 - to C 6 -alkanols, C 6 - to C 20 -phenols , Monocarboxylic acid monoalkyl esters having at least one hydrocarbyl chain having 8 to 30 carbon atoms and dicarboxylic acid dialkyl esters having at least one hydrocarbyl chain having 8 to 30 carbon atoms in an effective amount for the further lowering of the cloud point.
  • C inert polar diluent
  • inert polar diluents when combined with components (A), (B1) and (B2), cause further or increased lowering of the cloud point in middle distillate fuels, without sacrificing the response to lowering the cold filter plugging Point with the addition of cold flow improvers to deteriorate.
  • Examples of suitable C 8 - to C 30 -alkanols for component (C) are: n-octanol, 2-ethylhexanol, n-nonanol, isononanol, n-decanol, 2-propylheptanol, n-undecanol, n-octanol Dodecanol, n-tridecanol, iso-tridecanol, n-tetradecanol, n-pentadecanol, n-hexadecanol, n-heptadecanol, n-octadecanol, n-nonadecanol and eicosanol.
  • the branched alkanols 2-ethylhexanol, isononanol, 2-propylheptanol, isotridecanol and the linear alkanols n-heptadecanol and n-octadecanol show particularly good activity.
  • Suitable aryl-substituted C 1 -C 6 -alkanols for component (C) are, for example: benzyl alcohol, 2-phenylethanol, 3-phenylpropanol, 4-phenylbutanol and 6-phenylhexanol.
  • Examples of suitable C 6 - to C 20 -phenols for component (C) are: unsubstituted phenol, ⁇ -naphthol, ⁇ -naphthol, o-, m- and p-cresol, 2-tert-butylphenol, 4- tert-butylphenol, 2,4-di-tert-butylphenol and 2,6-di-tert-butylphenol.
  • Suitable monocarboxylic acid monoalkyl esters having at least one hydrocarbyl chain having 8 to 30 carbon atoms for the component (C) are firstly esters of shorter-chain carboxylic acids and longer-chain alcohols, such as n-octyl, 2-ethylhexyl, n-nonyl, iso-nonyl, n-decyl, 2-propylheptyl, n-undecyl, n-dodecyl, n-tridecyl, iso-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and eicosyl esters of formic acid, acetic acid, propionic acid, butyric acid, iso-butyric acid, valeric acid,
  • the carboxylic acid component has 1 to 12, in particular 1 to 8, especially 1 to 6 carbon atoms.
  • the esters of C 4 to C 6 monocarboxylic acids with the branched, long-chain alkanols 2-ethylhexanol, isononanol, 2-propylheptanol and isotridecanol show particularly good activity here.
  • monocarboxylic acid monoalkyl esters having at least one hydrocarbyl chain having 8 to 30 carbon atoms for the component (C) on the other esters of longer-chain carboxylic acids and shorter-chain alcohols such as methyl, ethyl, n-propyl, iso-propyl -, n-butyl, iso-butyl, sec-butyl and tert-butyl esters of C 12 - to C 20 fatty acids.
  • both pure fatty acids and technically conventional fatty acid mixtures are suitable, which contain, for example, stearic acid, palmitic acid, lauric acid, oleic acid, linoleic acid and / or linolenic acid, for example the mixtures tallow fatty acid, coconut oil fatty acid, trans fatty acid, coconut oil fatty acid, soybean oil fatty acid, rapeseed oil fatty acid, peanut oil fatty acid or palm oil fatty acid as main components oleic acid and palmitic acid.
  • the sunflower methyl ester used as biodiesel or biodiesel components, palm oil methyl ester ("PME"), soybean oil methyl ester ("SME”) or rapeseed oil methyl ester (“RME”) can also be used here.
  • Suitable dicarboxylic acid dialkyl esters having at least one hydrocarbyl chain having 8 to 30 carbon atoms are, for example, component (C): the di-n-octyl, di-2-ethylhexyl, di-n-nonyl, di-iso nonyl, di-n-decyl, di-2-propylheptyl, di-n-undecyl, di-n-dodecyl, di-n-tridecyl, di-iso-tridecyl, di-n-tetradecyl , Di-n-pentadecyl, di-n-hexadecyl, di-n-heptadecyl, di-n-octadecyl, di-n-nonadecyl and dieicosyl esters of oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid, glutaric acid , Ad
  • the two ester alcohol units may also be different but are preferably the same.
  • the diesters of C 4 -C 6 -dicarboxylic acids with the branched alkanols 2-ethylhexanol, isononanol, 2-propylheptanol and isotridecanol are particularly effective here.
  • a typical example of such a dicarboxylic acid diester is cyclohexane-1,2-dicarboxylic acid di-iso-nonyl ester.
  • This hydrocarbyl chain is the backbone of the monocarboxylic acid or ester alcohol or the bridging unit between two carboxylic acid functions.
  • inert nonpolar diluents (D) may also be present in the mixture used according to the invention.
  • the proportion of inert polar diluents (C) in the total amount of the inert diluent - ie the sum of (C) and (D) - should, if one is used, at least 20 wt .-%, in particular at least 40 wt .-% , especially at least 50 wt .-%, amount.
  • inert nonpolar diluents mention may be made in particular of aliphatic and aromatic hydrocarbons, for example xylenes or mixtures of high-boiling aromatics such as solvent naphtha. Even middle distillate fuels themselves can be used here as diluents.
  • the mixture used according to the invention can be prepared by simply mixing the said components without heat supply - without or with diluents (C) and / or (D).
  • the mixture used in the invention is used in the function as a cloud point depressant as an additive to middle distillate fuels, the already before the addition of additives a relatively low CP value of -8.0 ° C or lower, especially of -10.0 ° C or lower, to lower the cloud point, without at the same time deteriorate the response to the lowering of the cold filter plugging point with the addition of cold flow improvers.
  • Middle distillate fuels which are used in particular as gas oils, petroleum, diesel oils (diesel fuels) or light fuel oils, are often referred to as fuel oils.
  • Such middle distillate fuels generally have boiling temperatures of 150 to 400 ° C.
  • the mixture used according to the invention can be added to the middle distillate fuels with or without the abovementioned diluents.
  • the dosing rate of the cloud point depressant components mixture, i. from the components (A) and (B) or (A), (B) and (C), in the middle distillate fuels is generally 5 to 10,000 ppm by weight, in particular 10 to 5000 ppm by weight, especially 25 to 1000 ppm by weight, eg 50 to 400 ppm by weight, based in each case on the total amount of middle distillate fuel.
  • the fuel component (E) is usually referred to as "biodiesel".
  • the middle distillates of the fuel component (A) are preferably substantially alkyl esters of fatty acids derived from vegetable and / or animal oils and / or fats.
  • Alkyl esters are usually lower alkyl esters, in particular C 1 - to C 4 -alkyl esters, understood by transesterification of occurring in vegetable and / or animal oils and / or fats glycerides, especially triglycerides, by means of lower alcohols, for example ethanol, n-propanol, iso-propanol, n-butanol , iso-butanol, sec-butanol, tert-butanol, or especially methanol ("FAME").
  • Examples of vegetable oils which are converted into corresponding alkyl esters and thus can serve as a basis for biodiesel are castor oil, olive oil, peanut oil, palm kernel oil, coconut oil, mustard oil, cottonseed oil, and in particular sunflower oil, palm oil, soybean oil and rapeseed oil.
  • Other examples include oils that can be extracted from wheat, jute, sesame and the shea nut; furthermore, arachis oil, jatropha oil and linseed oil are also usable. The recovery of these oils and their conversion to the alkyl esters are known in the art or may be derived therefrom.
  • Vegetable fats are also useful in principle as a source of biodiesel, but play a minor role.
  • animal fats and oils that are converted to corresponding alkyl esters and thus can serve as the basis for biodiesel include fish oil, beef tallow, swine tallow, and similar fats and oils derived from the slaughtering or recycling of farmed or wild animals.
  • saturated or unsaturated fatty acids which usually have from 12 to 22 carbon atoms and may carry additional functional group such as hydroxyl groups, occur in the alkyl esters in particular lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid , Linoleic, linolenic, elaidic, erucic and ricinolic acids, especially in the form of mixtures of such fatty acids.
  • Typical lower alkyl esters based on vegetable and / or animal oils and / or fats which are used as biodiesel or biodiesel components are, for example, sunflower methyl ester, palm oil methyl ester ("PME”), soybean oil methyl ester (“SME”) and especially rapeseed oil methyl ester (“RME”). ).
  • fuel component (F) is to be understood to mean boiling middle distillate fuels in the range from 120 to 450 ° C.
  • middle distillate fuels are used in particular as diesel fuel, heating oil or kerosene, with diesel fuel and heating oil being particularly preferred.
  • middle distillate fuels fuels obtained by distillation of crude oil and boiling in the range of 120 to 450 ° C.
  • low sulfur middle distillate fuels are used, i. those containing less than 350 ppm by weight of sulfur, in particular less than 200 ppm by weight of sulfur, in particular less than 50 ppm by weight of sulfur.
  • the sulfur content of the middle distillate fuels used is at most 15 ppm by weight, in particular not more than 10 ppm by weight; such middle distillate fuels are also referred to as "sulfur-free".
  • These are generally crude oil distillates, which have been subjected to a hydrogenating refining and therefore contain only small amounts of polyaromatic and polar compounds.
  • middle distillate fuels which have 95% distillation points below 370 ° C., in particular below 350 ° C. and in special cases below 330 ° C.
  • Low-sulfur and sulfur-free middle distillate fuels can also be obtained from heavier petroleum fractions, which can no longer be distilled under atmospheric pressure.
  • Hydrocarbon cracking, thermal cracking, catalytic cracking, coker processes and / or visbreaking may be mentioned as typical conversion processes for producing middle distillate fuels from heavy petroleum fractions. Depending on the process, these middle distillate fuels are produced with little or no sulfur or are subjected to hydrogenating refining.
  • the middle distillate fuels preferably have aromatics contents of less than 28% by weight, in particular less than 20% by weight.
  • the content of normal paraffins is between 5% and 50% by weight, preferably between 10 and 35% by weight.
  • middle distillate fuels should also be understood middle distillates, which can be derived either indirectly from fossil sources such as oil or natural gas or produced from biomass via gasification and subsequent hydrogenation.
  • a typical example of a middle distillate fuel derived indirectly from fossil sources is GTL (gas-to-liquid) diesel fuel produced by Fischer-Tropsch synthesis.
  • GTL gas-to-liquid diesel fuel produced by Fischer-Tropsch synthesis.
  • a middle distillate is produced via the BTL (“biomass-to-liquid”) process, which can be used either alone or in admixture with other middle distillates as fuel component (F).
  • the middle distillates also include hydrocarbons obtained by hydrogenation of fats and fatty oils. They contain mostly n-paraffins.
  • the said middle distillate fuels have in common that they are essentially hydrocarbon mixtures and are free of fatty acid esters.
  • the oil-soluble polar nitrogen compounds of component (A) contained in the mixture used in the present invention are known in middle distillate fuels mainly as paraffin dispersants ("WASA"). Such oil-soluble polar nitrogen compounds often exert their effect as paraffin dispersants especially well together with the conventional cold flow improvers.
  • WASA paraffin dispersants
  • the components (A) contained in the mixture used according to the invention also develop their effect for lowering the cloud point in the context of the present invention generally particularly well together with such cold flow improvers.
  • the response to the lowering of the CFPP value with the concomitant use of such cold flow improvers is not worsened, in most cases this is even improved.
  • the monomer is preferably selected from alkenylcarboxylic esters, (meth) acrylic esters and olefins.
  • Suitable olefins for this purpose are, for example, those having 3 to 10 carbon atoms and having 1 to 3, preferably 1 or 2, in particular having a carbon-carbon double bond.
  • the carbon-carbon double bond can be arranged both terminally ( ⁇ -olefins) and internally.
  • ⁇ -olefins particularly preferably ⁇ -olefins having 3 to 6 carbon atoms, for example propene, 1-butene, 1-pentene and 1-hexene.
  • Suitable (meth) acrylic esters are, for example, esters of (meth) acrylic acid with C 1 - to C 10 -alkanols, in particular with methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, isobutanol, tert. Butanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol, nonanol, 2-propylheptanol and decanol.
  • Suitable alkenylcarboxylic esters are, for example, the vinyl and propenyl esters of carboxylic acids having 2 to 20 carbon atoms, the hydrocarbon radical of which may be linear or branched. Preferred among these are the vinyl esters.
  • carboxylic acids having a branched hydrocarbon radical preferred are those whose branch is in the ⁇ -position to the carboxyl group, the ⁇ -carbon atom being particularly preferably tertiary, ie. H. the carboxylic acid is a so-called neocarboxylic acid.
  • the hydrocarbon radical of the carboxylic acid is linear.
  • alkenylcarboxylic esters examples include vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, vinyl neopentanoate, vinyl hexanoate, vinyl neononanoate, vinyl neodecanoate and the corresponding propenyl esters, the vinyl esters being preferred.
  • a particularly preferred alkenyl carboxylic acid ester is vinyl acetate;
  • typical resulting copolymers of the additive class (G1) are ethylene-vinyl acetate copolymers ("EVA”), which are widely used in diesel fuels.
  • the ethylenically unsaturated monomer is in the copolymer of the additive class (G1) in an amount of preferably 1 to 50 mol .-%, in particular from 10 to 50 mol .-% and especially from 5 to 20 mol .-%, based on the total copolymer , copolymerized.
  • the copolymer of the additive class (G1) preferably has a number average molecular weight M n of from 1000 to 20,000, particularly preferably from 1000 to 10,000 and in particular from 1000 to 6000.
  • Comb polymers of the additive class (G2) are for example those described in " Comb-like polymers. Structure and Properties ", NA Plate and VP Shibaev, J. Poly. Sci. Macromolecular Revs., 8, pp. 117-253 (1974 Typical comb polymers which can be used here are those obtained by the copolymerization of maleic anhydride or fumaric acid with another ethylenically unsaturated monomer, for example with an ⁇ -olefin or an unsaturated ester, such as vinyl acetate, and subsequent esterification of the anhydride or acid function with an alcohol
  • Other useful comb polymers are copolymers of ⁇ -olefins and esterified comonomers, for example, esterified copolymers of styrene and maleic anhydride or esterified copolymers of styrene and fumaric acid.Mixtures of comb polymers are also suitable.Combpolymers may also be polyfum
  • Suitable polyoxyalkylenes of the additive class (G3) are, for example, polyoxyalkylene esters, ethers, ester / ethers and mixtures thereof.
  • the polyoxyalkylene compounds contain at least one, more preferably at least two linear alkyl groups each having 10 to 30 carbon atoms and a polyoxyalkylene group having a number average molecular weight of up to 5000.
  • the alkyl group of the polyoxyalkylene radical preferably contains 1 to 4 carbon atoms.
  • Such polyoxyalkylene compounds are for example in the EP-A 061 895 as well as in the U.S. 4,491,455 described.
  • Preferred polyoxyalkylene compounds are polyethylene glycols and polypropylene glycols having a number average molecular weight of from 100 to 5,000.
  • Preferred polyoxyalkylenes are also polyoxyalkylene esters of fatty acids having from 10 to 30 carbon atoms, such as stearic acid or behenic acid.
  • Preferred polyoxyalkylene compounds are also diesters of fatty acids having 10 to 30 carbon atoms, preferably stearic or behenic acid.
  • Suitable sulfocarboxylic acids / sulfonic acids or their derivatives of the additive class (G4) are, for example, sulfocarboxylic acids or sulfonic acids and their derivatives, as described in the EP-A-0 261 957 are described.
  • Suitable poly (meth) acrylic esters of the additive class (G5) are both homo- and copolymers of acrylic and methacrylic acid esters. Preferred are copolymers of at least two mutually different (meth) acrylic acid esters, which differ with respect to the fused alcohol. Optionally, the copolymer contains a further, different of which olefinically unsaturated monomer copolymerized. The weight-average molecular weight of the polymer is preferably 50,000 to 500,000.
  • a preferred polymer is a copolymer of methacrylic acid and methacrylic acid esters of saturated C 14 and C 15 alcohols wherein the acid groups are neutralized with hydrogenated tallamine.
  • Suitable poly (meth) acrylic esters are, for example, in WO 00/44857 described.
  • the middle distillate fuels in addition to the mixture used in the present invention in the presence of Kaltfeuerverêtern from the additive classes (G1) to (G5) in an amount of usually 1 to 2000 ppm by weight, preferably from 5 to 1000 ppm by weight, in particular of 10 to 750 ppm by weight and especially from 50 to 500 ppm by weight, eg from 150 to 400 ppm by weight.
  • This special mixture according to the invention is suitable as a constituent of additive concentrates for middle distillate fuels.
  • the stated middle distillate fuels or the said additive concentrates for middle distillate fuels may also be used as further additives in customary amounts of cold flow improvers (as described above), further paraffin dispersants, conductivity improvers, anti-corrosion additives, lubricity additives, antioxidants, metal oxides.
  • DK1 Ultra Low Sulfur Diesel
  • CP accordinging to ISO 3015
  • -10.4 ° C CFPP accordinging to EN 116): -12 ° C
  • Density d 15 (DIN 51577): 835.7 kg / m 3
  • Initial boiling point (DIN 51751): 185 ° C, boiling end: 354 ° C
  • Sulfur content 10 ppm by weight
  • the fuel DK1 was added in each case while stirring at 40 ° C with 200 ppm by weight of the mixtures M1 to M6 (active ingredient content: each 104 ppm by weight) and then cooled to room temperature. From these additized fuel samples, the CP was determined according to ISO 3015 and the CFPP according to EN 116, the measurements - as before on the non-additive fuel DK1 - respectively on non-sedimented total fuel (and not one in a short-term sedimentation test generated subphase) was made. This was done in accordance with the two standards mentioned above. The measurement accuracies and repeatabilities observed in this case were ⁇ 0.1 ° C for the CP value and ⁇ 1 ° C for the CFPP value.
  • Table 2 The results obtained are shown in Table 2 below: Table 2: mixture CP CFPP CFPP * [° C] [° C] [° C] unadditized DK1 -10.4 -12 DK1 only with MDFI -10.4 -27 DK1 with MDFI + M1 -12.7 -12 -31 DK1 with MDFI + M2 -13.0 -12 -30 DK1 with MDFI + M3 -13.4 -13 -32 DK1 with MDFI + M4 -13.0 -12 not determined DK1 with MDFI + M5 -12.4 -12 -31 DK1 with MDFI + M6 -12.2 -13 not determined

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Claims (9)

  1. Utilisation d'un mélange comprenant :
    (A) 5 à 95 % en poids d'au moins un composé azoté polaire soluble dans les huiles, différent du composant (B), qui est en mesure d'interagir à froid avec des cristaux de paraffine dans des combustibles de distillat moyen, et qui est choisi parmi les produits de réaction d'un acide dicarboxylique aromatique ou cycloaliphatique ou d'un acide succinique substitué avec des radicaux hydrocarbonés en C8 à C30 avec 2 moles d'amines primaires ou secondaires contenant au moins 8 atomes de carbone, et
    (B) 5 à 95 % en poids d'un mélange de deux composés aliphatiques solubles dans les huiles (B1) et (B2), contenant chacun au moins une chaîne alkyle ou alcényle linéaire ou ramifiée contenant au moins 8 atomes de carbone, pouvant être obtenus par réaction d'un acide mono- ou dicarboxylique aliphatique ou ses dérivés avec des mono- ou polyamines ou avec des alcools,
    (B1) correspondant à des produits de réaction d'acides α,β-dicarboxyliques aliphatiques contenant 4 à 300 atomes de carbone ou leurs dérivés avec des alkyl- ou alcényl-monoamines primaires en C8 à C30 et
    (B2) correspondant à des amides d'acides solubles dans les huiles de polyamines contenant 2 à 1 000 atomes d'azote et d'acides gras en C8 à C30 ou de composés analogues à des acides gras contenant des groupes carboxyle libres,
    pour l'abaissement du point de trouble (« CP ») de combustibles de distillat moyen, qui présentent avant l'ajout d'additifs une valeur CP de -8,0 °C ou moins, d'au moins 1,5 °C par rapport au combustible de distillat moyen sans additif, à un dosage du mélange dans la plage allant de 50 à 300 ppm en poids, les valeurs CP étant à chaque fois déterminées dans le combustible de distillat moyen non sédimenté, sans aggravation simultanée du comportement de réponse pour l'abaissement de la température limite de filtrabilité des gazoles (« CFPP ») lors de l'ajout d'agents d'amélioration de l'écoulement à froid.
  2. Utilisation d'un mélange selon la revendication 1 pour l'abaissement du point de trouble de combustibles de distillat moyen présentant une teneur en soufre d'au plus 15 ppm en poids.
  3. Utilisation d'un mélange selon la revendication 1 ou 2, dans laquelle les composés azotés polaires solubles dans les huiles (A) sont des amides, des sels d'amide-ammonium ou des sels d'ammonium, dans lesquels aucun, un ou plusieurs des groupes acide carboxylique ont été transformés en groupes amide.
  4. Utilisation d'un mélange selon les revendications 1 à 3, dans laquelle les amines primaires ou secondaires contenant au moins 8 atomes de carbone transformées en les composés azotés polaires solubles dans les huiles (A) sont des amines secondaires de formule générale HNR2, dans laquelle les deux variables R signifient à chaque fois indépendamment l'une de l'autre des radicaux alkyle ou alcényle en C8 à C30 linéaires ou ramifiés.
  5. Utilisation d'un mélange selon la revendication 1 ou 2, dans laquelle le composé aliphatique soluble dans les huiles (B1) est un produit de réaction d'anhydride de l'acide maléique et d'alkylamines primaires en C9 à C15.
  6. Utilisation d'un mélange selon la revendication 1 ou 2, dans laquelle le composé aliphatique soluble dans les huiles (B2) est un amide d'acide soluble dans les huiles de polyamines aliphatiques contenant 2 à 6 atomes d'azote et d'acides gras en C12 à C20, toutes les fonctions amino primaires et secondaires des polyamines ayant été transformées en fonctions amide d'acide.
  7. Utilisation d'un mélange selon les revendications 1 à 6, comprenant en tant que composant supplémentaire au moins un diluant polaire inerte (C) choisi parmi les alcanols en C8 à C30, les alcanols en C1 à C6 à substitution aryle, les phénols en C6 à C20, les esters monoalkyliques d'acides monocarboxyliques contenant au moins une chaîne hydrocarbyle de 8 à 30 atomes de carbone et les esters dialkyliques d'acides dicarboxyliques contenant au moins une chaîne hydrocarbyle de 8 à 30 atomes de carbone, en une quantité efficace pour l'abaissement supplémentaire du point de trouble.
  8. Mélange, contenant :
    (a1) 5 à 60 % en poids d'au moins un produit de réaction soluble dans les huiles (A1) d'un acide dicarboxylique aromatique ou cycloaliphatique ou d'un acide succinique substitué avec des radicaux hydrocarbonés en C8 à C30 avec 2 moles d'amines primaires ou secondaires contenant au moins 8 atomes de carbone,
    (b1) 3 à 40 % en poids d'au moins un produit de réaction aliphatique soluble dans les huiles (B1) d'un acide α,β-dicarboxylique aliphatique contenant 4 à 300 atomes de carbone ou ses dérivés avec des alkyl- ou alcényl-amines primaires en C8 à C30,
    (b2) 1 à 30 % en poids d'au moins un amide d'acide aliphatique soluble dans les huiles (B2) de polyamines contenant 2 à 1 000 atomes d'azote et d'acides gras en C8 à C30 ou de composés analogues à des acides gras contenant des groupes carboxyle libres, et
    (c/d) 5 à 75 % en poids d'au moins un diluant inerte qui comprend, en plus de composants diluants inertes apolaires (D), au moins 20 % en poids, par rapport à la quantité totale du diluant inerte, d'au moins un diluant inerte polaire (C), choisi parmi les alcanols en C8 à C30, les alcanols en C1 à C6 à substitution aryle, les phénols en C6 à C20, les esters monoalkyliques d'acides monocarboxyliques contenant au moins une chaîne hydrocarbyle de 8 à 30 atomes de carbone et les esters dialkyliques d'acides dicarboxyliques contenant au moins une chaîne hydrocarbyle de 8 à 30 atomes de carbone,
    la somme des quatre composants cités étant de 100 % en poids.
  9. Utilisation du mélange selon la revendication 8 en tant que constituant de concentrés additifs pour combustibles de distillat moyen.
EP10711676.6A 2009-04-07 2010-03-30 Mélange de composés azotés polaires solubles dans l'huile et de composés aliphatiques solubles dans l'huile servant à abaisser le cloud point dans les carburants diesel Not-in-force EP2417229B1 (fr)

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US8721744B2 (en) 2010-07-06 2014-05-13 Basf Se Copolymer with high chemical homogeneity and use thereof for improving the cold flow properties of fuel oils
US8790424B2 (en) 2011-03-30 2014-07-29 Basf Se Copolymer and use thereof for improving the cold flow properties of middle distillate fuels
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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
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EP2217061A2 (fr) 2007-11-09 2010-08-18 Basf Se Éther en tant qu'agent potentialisant pour des biocides
EP2235144B1 (fr) * 2008-01-22 2018-09-26 Basf Se Production de mélanges d'additifs
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