WO2009150145A1 - Utilisation d'agents solubilisants pour l'homogénéisation de concentrés d'additifs - Google Patents

Utilisation d'agents solubilisants pour l'homogénéisation de concentrés d'additifs Download PDF

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Publication number
WO2009150145A1
WO2009150145A1 PCT/EP2009/057076 EP2009057076W WO2009150145A1 WO 2009150145 A1 WO2009150145 A1 WO 2009150145A1 EP 2009057076 W EP2009057076 W EP 2009057076W WO 2009150145 A1 WO2009150145 A1 WO 2009150145A1
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Prior art keywords
solubilizer
groups
acid
carbon atoms
additive concentrates
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PCT/EP2009/057076
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English (en)
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Frank-Olaf Mähling
Irene Trötsch-Schaller
Heinrich Lubojanski
Thomas Pfeiffer
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Basf Se
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Publication of WO2009150145A1 publication Critical patent/WO2009150145A1/fr

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Definitions

  • the present invention relates to the use of specific dicarboxylic acid derivatives as solubilizers for homogenizing additive concentrates which comprise cold flow improvers, detergent additives, inert organic solvents and if appropriate cetane number improvers.
  • the invention further relates to additive concentrates suitable for additizing fuel oil compositions which consist predominantly of a middle distillate fuel which boils in the range of 120-500 0 C and/or a renewable fuel, said additive concentrates having the ingredients mentioned.
  • additive concentrates which, as well as cold flow improvers which are typically added to the diesel fuels and heating oils in the mineral oil refineries, also comprise detergent additives and cetane number improvers which form the main constituents of so-called diesel performance packages, there are frequent occurrences - especially at temperatures significantly below 20 0 C - of flaky precipitates which cannot be filtered off; attempted filtration can lead to filter conglutination.
  • additive concentrates are, however, generally slightly to highly turbid.
  • the presence of additionally used organic solvents in the additive concentrates cannot prevent such flaky precipitates or turbidities.
  • the flaky precipitates which usually at first remain more or less dispersed in the solution, can subsequently lead to severe sedimentation or to gel formation in the additive concentrate.
  • R 1 denotes a hydrocarbylene radical having from 1 to 12 carbon atoms or a hydrocarbylene radical which has from 2 to 12 carbon atoms, is interrupted by one or more heteroatoms selected from the group of O, S and N, and may in each case bear one or more functional groups selected from the group of OH, OR 3 , NH 2 , NHR 4 , NR 4 R 5 , COOH, COOR 7 , CONHR 4 and CONR 4 R 5 , where amino groups may also be present in protonated form and carboxylic acid groups also in deprotonated form,
  • X is OH, OR 3 , NH 2 , NHR 4 or NR 4 R 5 , where, in the case that X together with the adjacent carbonyl group is a carboxylic acid radical, this radical is present in deprotonated form and the accompanying cation may be a hydrocarbyl- substituted ammonium cation selected from the group of [HsNR 8 J + , [H 2 NR 8 R 9 J + and [HNR 8 R 9 R 1Q ] + ,
  • Y is O, S, NH or NR 6 , or, in the case that X is NH 2 or NHR 4 , is a chemical bond to X with formation of an imide structure,
  • R 2 to R 10 are each independently hydrocarbyl radicals having from 1 to 30 carbon atoms
  • R 2 , R 3 , R 4 , R 5 , R 6 and R 7 radicals has at least 4 carbon atoms
  • additive concentrates suitable for additizing fuel oil compositions which consist predominantly of a middle distillate fuel which boils in the range of 120-500 0 C and/or a renewable fuel, said additive concentrates comprising
  • the additive concentrates mentioned preferably additionally comprise
  • solubilizers I used according to the invention also occurs in principle in additive concentrates which do not comprise any cetane number improver.
  • solubilizers I used in accordance with the invention are used to homogenize additive concentrates which comprise (A) from 1 to 50% by weight, especially from 2 to 40% by weight, in particular from 3 to 20% by weight, of at least one cold flow improver,
  • (B) from 0.5 to 40% by weight, preferably from 0.7 to 20% by weight, especially from 1 to 12% by weight, in particular from 1.5 to 7% by weight, of at least one detergent additive,
  • (C) from 1 to 60% by weight, especially from 3 to 50% by weight, in particular from 5 to 40% by weight, of an inert organic solvent or of a mixture of such solvents and
  • (D) from 0 to 80% by weight, especially from 25 to 75% by weight, in particular from 40 to 70% by weight, of at least one cetane number improver.
  • the additive concentrates mentioned may additionally comprise further ingredients, in which case the sum of all ingredients adds up to 100% by weight.
  • homogenization shall be understood to mean the prevention or the elimination of the flaky precipitates or turbidities described above in the additive concentrates.
  • the specific dicarboxylic acid derivatives of the general formula I used as solubilizers in the present invention are known from WO 2007/131894. They are recommended there as cold stabilization enhancers in fuel oil compositions which comprise customary cold flow improvers and detergent additives, in low dosages - specifically from 1 to 2000 ppm by weight, based on the fuel oil composition. Corresponding additive concentrates or technical problems to be solved with such additive concentrates are not addressed in WO 2007/131894.
  • EP-A 807 676 discloses low-sulfur middle distillate fuels which, to improve their lubricity, comprise carboxamides, for example also amides of C3- to C4o-dicarboxylic acids, cold flow improvers and ashless dispersants.
  • the additives mentioned may also be added to the middle distillate fuels in the form of a concentrate which typically also comprises diluents or solvents.
  • EP-A 301 448 describes alkali metal or alkaline earth metal salts of amides of di-, tri- or tetracarboxylic acids, for example monoamides of dicarboxylic acids such as maleic acid, as valve seat wear-reducing additives for gasoline fuels.
  • EP-A 555 006 discloses the wear-reducing action of dicarboxylic acid derivatives such as the reaction product of maleic anhydride with a secondary amine to give the monoamide in the form of the alkali metal salt in internal combustion engines operated with gasoline fuel.
  • EP-A 798 364 describes amides obtained by condensation reactions of carboxylic acids with aliphatic amines as additives for diesel fuels for reducing deposits at the injection nozzles, for increasing the lubricity of the fuel and for reducing the wear of the injection pumps.
  • These amides are based preferably on relatively long-chain mono- carboxylic acids, especially having from 8 to 30 carbon atoms, such as oleic acid, and on relatively long-chain amines, especially those having from 8 to 20 carbon atoms, such as oleylamine or oleylpropylenediamine.
  • dodecenylsuccinic acid and its anhydride are also mentioned as a starting material for such amides.
  • the amides mentioned may be used together with other customary diesel additives such as low- temperature flow improvers, cetane number improvers, antioxidants, metal deactivators, rust and corrosion inhibitors, demulsifiers and foam inhibitors.
  • the compounds of the general formula I are dicarboxylic acid derivatives.
  • they are present especially in the form of monoesters, monothioesters, monoamides, diesters, bisthioesters, diamides or mixed derivatives having in each case two different functions from the group of the ester, thioester and amide functions or are joined to form a cycle via an imide function.
  • variable R 1 in the compounds I is the bridging member between the two carbonyl carbon atoms.
  • a hydrocarbylene radical shall be understood here to mean a divalent hydrocarbon radical of any structure which, however, in accordance with the definition, may also comprise heteroatoms and/or functional groups.
  • the hydrocarbenyl radical may be saturated, unsaturated or of aromatic nature; it may have a linear, branched or cyclic structure.
  • Compounds of the formula I which comprise benzene or pyridine skeletons for R 1 are based, for example, on benzenedi-, -tri- or -tetracarboxylic acids such as phthalic acid (benzene-1 ,2-dicarboxylic acid), isophthalic acid (benzene-1 ,3-dicarboxylic acid), terephthalic acid (benzene-1 ,4-dicarboxylic acid), trimellitic acid (benzene-1 ,2,4-tri- carboxylic acid), trimesic acid (benzene-1 ,3,5-tricarboxylic acid) or pyromellitic acid (benzene-1 ,2,4,5-tetracarboxylic acid) or on pyridinedicarboxylic acids such as quino- linic acid (pyridine-2,3-dicarboxylic acid), lutidinic acid (pyridine-2,4-dicarboxylic acid), dipicolinic acid (pyridine-2,6-dicar
  • Hydrocarbylene radicals interrupted by heteroatoms from the group of O, S and N for R 1 are especially d- to Ci2-alkylene groups which comprise, incorporated in their chain, one, two or three oxygen, sulfur and/or nitrogen atoms, where, in the case of nitrogen atoms, their free valence is preferably saturated by a lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl; examples thereof are -CH 2 -O-CH 2 -, -CH 2 CH 2 -O-CH 2 -CH 2 -, -CH 2 -N(CHs)-CH 2 -, -CH 2 CH 2 -N(CH 3 )- CH 2 -CH 2 and -CH 2 CH 2 -O-CH 2 CH 2 -O-CH 2 CH 2 -.
  • hydrocarbyl-substituted ammonium cations selected from the group of [H 3 N R 8 ] + , [H 2 NR 8 R 9 ] + and [HNR 8 R 9 R 10 J + occur as cations;
  • the variables R 8 , R 9 and R 10 therein each independently denote preferably linear or branched alkyl radicals such as methyl, ethyl, vinyl, n-propyl, isopropyl, 1-propenyl, 2-propenyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, neooctyl, nonyl, neononyl, decyl, 2-propylheptyl, neodecyl, unde
  • R 2 , R 3 , R 4 , R 5 , R 6 or R 7 radicals are a hydrocarbyl radical having from 1 to 30 carbon atoms, it shall be understood here to mean a virtually purely hydrocarbon radical of any structure, which, however, provided that this does not distort the dominant hydrocarbon character, may still have, to a small degree, heteroatoms, for example O or N, and/or functional groups with heteroatoms, for example OH groups.
  • This hydrocarbyl radical may be of saturated, unsaturated or aromatic nature; it may have a linear, branched or cyclic structure.
  • such a hydrocarbyl radical having from 1 to 30 carbon atoms for one of the R 2 , R 3 , R 4 , R 5 , R 6 or R 7 radicals is preferably a linear or branched alkyl or alkenyl radical such as methyl, ethyl, vinyl, n-propyl, isopropyl, 1-propenyl, 2-propenyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, neooctyl, nonyl, neononyl, decyl, 2-propylheptyl, neodecyl, undecyl, neoundecyl, dodecyl, tridecyl, isotridecyl,
  • such a hydrocarbyl radical having from 1 to 30 carbon atoms for one of the R 2 , R 3 , R 4 , R 5 , R 6 or R 7 radicals may also be an aryl, alkaryl or arylalkyl radical, for example phenyl, naphthyl, benzyl, 2-phenylethyl, 3-phe- nylpropyl, 4-phenylbutyl, or o-, m- or p-xylyl.
  • At least one of the R 2 , R 3 , R 4 , R 5 , R 6 or R 7 radicals in the solubilizers I must have at least 4, preferably at least 6, especially at least 8, more preferably at least 10, in particular at least 12 carbon atoms, in order that the compounds I have the necessary oil solubility.
  • Such relatively long-chain radicals are typically present in the form of linear or slightly branched alkyl or alkenyl chains as described above.
  • the remaining R 2 , R 3 , R 4 , R 5 , R 6 or R 7 radicals are then typically short-chain, i.e. they have generally from 1 to 4 carbon atoms, or the corresponding valences in the compound I are saturated by hydrogen.
  • At least one solubilizer I in which the variable X is OH is used for the present invention; they are then especially dicarboxylic monoesters, dicarboxylic monothioesters or dicarboxylic monoamides.
  • At least one solubilizer I which derives from maleic acid or phthalic acid, i.e. the bridging member R 1 is a 1 ,2-vinylidene group of the formula -CH CH- or a 1 ,2-phenylene group, is used for the present invention.
  • the solubilizers I used in accordance with the invention are present in the additive concentrates generally in an amount of from 1.05 to 15% by weight, preferably from 1.25 to 13.5% by weight, more preferably from 1.5 to 12% by weight, especially from 2.0 to 10% by weight, in particular from 2.5 to 7% by weight, based in each case on the total amount of the additive concentrate.
  • the preferred ranges mention- ned are sufficient to obtain a sufficient homogenizing action in the additive concen- trates.
  • the lower limit for the amount of solubilizers I used in accordance with the invention is critical; it has been found that amounts up to 1 % by weight are frequently still not sufficient to obtain the desired homogenization.
  • cold flow improvers of component (A) shall be understood to mean all additives which improve the cold properties of fuel oil compositions.
  • MDFIs actual cold flow improvers
  • WASAs paraffin dispersants
  • WAFIs the combination of MDFIs and WASAs
  • (A) should advantageously be one or more representatives selected from
  • the monomer is preferably selected from alkenylcarboxylic esters, (meth)acrylic esters and olefins.
  • Suitable olefins are, for example, those having from 3 to 10 carbon atoms and having from 1 to 3, preferably having 1 or 2 carbon-carbon double bonds, in particular having one carbon-carbon double bond. In the latter case, the carbon-carbon double bond may be arranged either terminally ( ⁇ -olefins) or internally. However, preference is given to ⁇ -olefins, particular preference to ⁇ -olefins having from 3 to 8 carbon atoms, such as propene, 1-butene, 1-pentene, 1-hexene and 1-octene.
  • Suitable (meth)acrylic esters are, for example, esters of (meth)acrylic acid with C1-C14- alkanols, especially with methanol, ethanol, propanol, isopropanol, n-butanol, sec-bu- tanol, isobutanol, tert-butanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol, nonanol, decanol, 2-propylheptanol, dodecanol and tetradecanol.
  • Suitable alkenylcarboxylic esters are, for example, the vinyl and propenyl esters of carboxylic acids having from 2 to 20 carbon atoms whose hydrocarbon radical may be linear or branched. Among these, preference is given to the vinyl esters.
  • carboxylic acids having a branched hydrocarbon radical preference is given to those whose branch is disposed in the ⁇ -position to the carboxyl group, and particular preference is given to the ⁇ -carbon atom being tertiary, i.e. the carboxylic acid is a neocarboxylic acid.
  • 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, preference being given to the vinyl esters.
  • a particularly preferred alkenylcarboxylic ester is vinyl acetate; typical copolymers of group (Aa) resulting therefrom are ethylene-vinyl acetate copolymers ("EVA”), which are used in diesel fuels on a large scale.
  • EVA ethylene-vinyl acetate copolymers
  • ethylenically unsaturated monomer being selected from alkenylcarboxylic esters.
  • copolymers which comprise two or more different copolymerized alkenylcarboxylic esters which differ in the alkenyl function and/or in the carboxylic acid group.
  • copolymers which, in addition to the alkenylcarboxylic ester(s), comprise at least one copolymerized olefin and/or at least one copolymerized (meth)acrylic ester.
  • the ethylenically unsaturated monomer is copolymerized in the copolymer of group (Aa) in an amount of preferably from 1 to 50 mol%, more preferably from 10 to 50 mol% and in particular from 5 to 20 mol%, based on the overall copolymer.
  • the copolymer of group (Aa) preferably has a number-average molecular weight M n of from 500 to 20 000, more preferably from 7500 to 10 000 and in particular from 1000 to 6000.
  • Comb polymers of group (Ab) are, for example, those described in "Comb-Like Polymers. Structure and Properties", N. A. Plate and V. P. Shibaev, J. Poly. Sci. Macromolecular Revs. 8, pages 117 to 253 (1974).
  • suitable comb polymers are, for example, those of the formula Il
  • D is R 17 , COOR 17 , OCOR 17 , R 18 , OCOR 17 or OR 17 ,
  • E is H, CH 3 , D or R 18 ,
  • G is H or D
  • J is H, R 18 , R 18 COOR 17 , aryl or heterocyclyl,
  • K is H, COOR 18 , OCOR 18 , OR 18 or COOH
  • L is H, R 18 , COOR 18 , OCOR 18 , COOH or aryl,
  • R 17 is a hydrocarbon radical having at least 10 carbon atoms, preferably having from
  • R 18 is a hydrocarbon radical having at least one carbon atom, preferably having from 1 to 30 carbon atoms, m is a molar fraction in the range from 1.0 to 0.4 and n is a molar fraction in the range from O to 0.6.
  • Preferred comb polymers are, for example, obtainable by 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 having at least 10 carbon atoms.
  • Further preferred 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.
  • Also suitable are mixtures of comb polymers.
  • Comb polymers may also be polyfumarates or polymaleates. Homo- and copolymers of vinyl ethers are also suitable comb polymers.
  • Suitable polyoxyalkylenes of group (Ac) are, for example, polyoxyalkylene esters, ethers, ester/ethers and mixtures thereof.
  • the polyoxyalkylene compounds preferably comprise at least one linear alkyl group, more preferably at least two linear alkyl groups, having from 10 to 30 carbon atoms and a polyoxyalkylene group having a molecular weight of up to 5000.
  • the alkyl group of the polyoxyalkylene radical preferably comprises from 1 to 4 carbon atoms.
  • Such polyoxyalkylene compounds are described, for example, in EP-A-O 061 895 and also in US 4,491 ,455, which are hereby fully incorporated by reference.
  • Preferred polyoxyalkylene esters, ethers and ester/ethers have the general formula III R 19 £0- ⁇ CH 2 ) y kO-R 20 (III) in which
  • R 19 and R 20 are each independently R 21 , R 2I -CO-, R 21 -O-CO(CH 2 ) Z - or R 21 -O-CO(CH 2 ) Z - CO- where R 21 is linear d-Cso-alkyl, y is from 1 to 4, x is from 2 to 200, and z is from 1 to 4.
  • Preferred polyoxyalkylene compounds of the formula III in which both R 19 and R 20 are R 21 are polyethylene glycols and polypropylene glycols having a number-average molecular weight of from 100 to 5000.
  • Preferred polyoxyalkylenes of the formula III in which one of the R 19 radicals is R 21 and the other is R 21 -CO- are polyoxyalkylene esters of fatty acids having from 10 to 30 carbon atoms, such as stearic acid or behenic acid.
  • Preferred polyoxyalkylene compounds in which both R 19 and R 20 are an R 21 -CO- radical are diesters of fatty acids having from 10 to 30 carbon atoms, preferably of stearic acid or behenic acid.
  • the polar nitrogen compounds of group (Ad), which are advantageously oil-soluble, may be either ionic or nonionic and preferably have at least one substituent, more preferably at least 2 substituents, of the formula >NR 22 in which R 22 is a C8-C4o-hydro- carbon radical.
  • the nitrogen substituents may also be quaternized, i.e. be in cationic form.
  • An example of such nitrogen compounds is that of ammonium salts and/or amides which are obtainable by the reaction of at least one amine substituted by at least one hydrocarbon radical with a carboxylic acid having from 1 to 4 carboxyl groups or with a suitable derivative thereof.
  • the amines preferably comprise at least one linear C8-C4o-alkyl radical.
  • Suitable primary amines are, for example, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tetradecylamine and the higher linear homologs.
  • Suitable secondary amines are, for example, dioctadecylamine and methyl- behenylamine.
  • amine mixtures in particular amine mixtures obtainable on the industrial scale, such as fatty amines or hydrogenated tallamines, as described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 6th Edition, "Amines, aliphatic" chapter.
  • Acids suitable for the reaction are, for example, cyclo- hexane-1 ,2-dicarboxylic acid, cyclohexene-1 ,2-dicarboxylic acid, cyclopentane-1 ,2-di- carboxylic acid, naphthalenedicarboxylic acid, phthalic acid, isophthalic acid, terephthalic acid and succinic acids substituted with long-chain hydrocarbon radicals.
  • a further example of polar nitrogen compounds of group (Ad) is that of ring systems which bear at least two substituents of the formula -A-NR 23 R 24 in which A is a linear or branched aliphatic hydrocarbon group which is optionally interrupted by one or more groups selected from O, S, NR 35 and CO, and R 23 and R 24 are each a C9-C4o-hydrocar- bon radical which is optionally interrupted by one or more groups selected from O, S, NR 35 and CO, and/or substituted by one or more substituents selected from OH, SH and NR 35 R 36 where R 35 is Ci-C4o-alkyl which is optionally interrupted by one or more moieties selected from CO, NR 35 , O and S, and/or substituted by one or more radicals selected from NR 37 R 38 , OR 37 , SR 37 , COR 37 , COOR 37 , CONR 37 R 38 , aryl or heterocyclyl, where R 37 and R 38 are each independently selected from H or
  • A is preferably a methylene or polymethylene group having from 2 to 20 methylene units.
  • suitable R 23 and R 24 radicals are 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl, 2-ketopropyl, ethoxyethyl and propoxypropyl.
  • the cyclic system may be homocyclic, heterocyclic, fused polycyclic or nonfused polycyclic systems.
  • the ring system is preferably carbo- or heteroaromatic, in particular carboaromatic.
  • polycyclic ring systems examples include fused benzoid structures such as naphthalene, anthraxcene, phenanthrene and pyrene, fused nonbenzoid structures such as azulene, indene, hydrindene and fluorene, nonfused polycycles such as diphenyl, heterocycles such as quinoline, indole, dihydroindole, benzofuran, coumarin, isocoumarin, benzothiophene, carbazole, diphenylene oxide and diphenylene sulfide, nonaromatic or partially saturated ring systems such as decalin, and three-dimensional structures such as ⁇ -pinene, camphene, bornylene, norbornane, norbornene, bicyclooctane and bicyclooctene.
  • fused benzoid structures such as naphthalene, anthraxcene, phenanthrene and pyrene
  • a further example of suitable polar nitrogen compounds is that of condensates of long- chain primary or secondary amines with carboxyl group-containing polymers.
  • Suitable polar nitrogen compounds are also described, for example, in DE-A-198 48 621 , DE-A-196 22 052 or EP-B 398 101 , which are hereby incorporated by reference.
  • Suitable sulfo carboxylic acids/sulfonic acids or their derivatives of group (Ae) are, for example, those of the general formula IV
  • Y' is SO 3 -(N R 25 sR 26 ) + , SO 3 -(N H R 25 2 R 26 ) + , SO 3 -(NH 2 R 25 R 26 ), SO 3 -(NH 3 R 26 ) or SO 2 NR 25 R 26
  • X' is Y', CONR 25 R 27 , CO 2 -(N R 25 3 R 27 ) + , CO 2 -(N H R 25 2 R 27 ) + , R 28 -COOR 27 , NR 25 COR 27 , R 28 OR 27 , R 28 OCOR 27 , R 28 R 27 , N(COR 25 )R 27 or Z " (NR 25 3 R 27 ) + , where
  • R 25 is a hydrocarbon radical
  • R 26 and R 27 are each alkyl, alkoxyalkyl or polyalkoxyalkyl having at least 10 carbon atoms in the main chain
  • R 28 is C 2 -C 5 -alkylene
  • Z- is one anion equivalent
  • A' and B are each alkyl, alkenyl or two substituted hydrocarbon radicals or, together with the carbon atoms to which they are bonded, form an aromatic or cycloaliphatic ring system.
  • Suitable poly(meth)acrylic esters of group (Af) are either homo- or copolymers of acrylic and methacrylic esters. Preference is given to copolymers of at least two different (meth)acrylic esters which differ in the esterified alcohol. Optionally, the copolymer comprises another different copolymerized olefinically unsaturated monomer.
  • the weight-average molecular weight of the polymer is preferably from
  • a particularly preferred polymer is a copolymer of methacrylic acid and methacrylic esters of saturated Ci 4 - and Cis-alcohols, in which the acid groups have been neutralized with hydrogenated tallamine.
  • Suitable poly(meth)acrylic esters are described, for example, in WO 00/44857, which is hereby fully incorporated by reference.
  • the additive concentrates mentioned preferably comprise, as component (A), at least one cold flow improver of group (Aa) or a mixture of one or more cold flow improvers of group (Aa) and one or more cold flow improvers selected from the remaining groups (Ab) to (Af), especially a mixture of one or more cold flow improvers of group (Aa) and one or more cold flow improvers of group (Ad).
  • the additive concentrates mentioned comprise, as cold flow improvers of components (A), one or more representatives selected from
  • N,N-dialkylammonium salts of 2-N',N'-dialkylamidobenzoates representatives of group (Ad)
  • the detergent additives of component (B) to be used in the additive concentrates mentioned are generally advantageously amphiphilic substances which have at least one hydrophobic hydrocarbon radical having a number-average molecular weight (M n ) of from 85 to 20 000 and at least one polar moiety which is selected from
  • the hydrophobic hydrocarbon radical in the above detergent additives which ensures the adequate solubility in the fuel oil composition, has a number-average molecular weight (Mn) of from 85 to 20 000, especially from 1 13 to 10 000, in particular from 300 to 5000.
  • detergent additives examples include the following:
  • polybutene or polyisobutene having predominantly internal double bonds usually in the beta- and gamma-position
  • a possible preparative route is by chlorination and subsequent amination or by oxidation of the double bond with air or ozone to give the carbonyl or carboxyl compound and subsequent amination under reductive (hydrogenating) conditions.
  • the amines used here for the amination may be, for example, ammonia, monoamines or polyamines, such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
  • amines used here for the amination may be, for example, ammonia, monoamines or polyamines, such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
  • Corresponding additives based on polypropene are described in particular in WO-A-94/24231.
  • Further preferred additives comprising monoamino groups (Ba) are the hydrogenation products of the reaction products of polyisobutenes having an average degree of polymerization P of from 5 to 100 with nitrogen oxides or mixtures of nitrogen oxides and oxygen, as described in particular in WO-A-97/03946.
  • additives comprising monoamino groups (Ba) are the compounds obtainable from polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols, as described in particular in DE-A-196 20 262.
  • These reaction products are generally mixtures of pure nitropoly- isobutenes (e.g. ⁇ , ⁇ -dinitropolyisobutene) and mixed hydroxynitropolyiso-butenes (e.g. ⁇ -nitro- ⁇ -hydroxypolyisobutene).
  • Additives comprising carboxyl groups or their alkali metal or alkaline earth metal salts are preferably copolymers of C2-C4o-olefins with maleic anhydride which have a total molar mass of from 500 to 20 000 and of whose carboxyl groups some or all have been converted to the alkali metal or alkaline earth metal salts and any remainder of the carboxyl groups has been reacted with alcohols or amines.
  • Such additives are disclosed in particular by EP-A-307 815.
  • Such additives serve mainly to prevent valve seat wear and can, as described in WO-A-87/01 126, advantageously be used in combination with customary fuel detergents such as poly(iso)buteneamines or polyetheramines.
  • Additives comprising sulfonic acid groups or their alkali metal or alkaline earth metal salts are preferably alkali metal or alkaline earth metal salts of an alkyl sulfosuccinate, as described in particular in EP-A-639 632.
  • Such additives serve mainly to prevent valve seat wear and can be used advantageously in combination with customary fuel detergents such as poly(iso)buteneamines or polyetheramines.
  • Additives comprising polyoxy-C2-C4-alkylene moieties are preferably polyethers or polyether amines which are obtainable by reaction of C2-C6o-alkanols, C ⁇ -Cso-alkane- diols, mono- or di-C2-C3o-alkylamines, Ci-C3o-alkylcyclohexanols or Ci-C3o-alkylphenols with from 1 to 30 mol of ethylene oxide and/or propylene oxide and/or butylene oxide per hydroxyl group or amino group and, in the case of the polyether amines, by subsequent reductive amination with ammonia, monoamines or polyamines.
  • Such products are described in particular in EP-A-310 875, EP-A-356 725, EP-A-700 985 and US-A-4 877 416.
  • polyethers such products also have carrier oil properties. Typical examples of these are tridecanol butoxylates, isotridecanol butoxy- lates, isononylphenol butoxylates and polyisobutenol butoxylates and propoxylates and also the corresponding reaction products with ammonia.
  • Additives comprising carboxylic ester groups (Bg) are preferably esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, in particular those having a minimum viscosity of 2 mm 2 /s at 100 0 C, as described in particular in DE-A-38 38 918.
  • the mono-, di- or tricarboxylic acids used may be aliphatic or aromatic acids, and particularly suitable ester alcohols or ester polyols are long-chain representatives having, for example, from 6 to 24 carbon atoms.
  • esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, of isononanol, of isodecanol and of isotridecanol.
  • Such products also have carrier oil properties.
  • Particular interest attaches to derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
  • the moieties having hydroxyl and/or amino and/or amido and/or imido groups are, for example, carboxylic acid groups, acid amides of monoamines, acid amides of di- or polyamines which, in addition to the amide function, also have free amine groups, succinic acid derivatives having an acid and an amide function, carboximides with monoamines, carboximides with di- or polyamines which, in addition to the imide function, also have free amine groups, or diimides which are formed by the reaction of di- or polyamines with two succinic acid derivatives.
  • Such fuel additives are described in particular in US-A-4 849 572.
  • Additives comprising moieties (Bi) obtained by Mannich reaction of substituted phenols with aldehydes and mono- or polyamines are preferably reaction products of polyiso- butene-substituted phenols with formaldehyde and mono- or polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine or dimethylaminopropylamine.
  • These are preferably the reaction products of alkyl- or alkenyl-substituted succinic anhydrides, especially of polyisobutenylsuccinic anhydrides, with amines. It will be appreciated that these reaction products are not obtainable only when substituted succinic anhydride is used, but also when substituted succinic acid or suitable acid derivatives, such as succinyl halides or succinic esters, are used.
  • the additive concentrates mentioned comprise, as a detergent additive of component (B), one or more derivatives which have been derived from polyisobutenylsuccinic anhydride and have amino and/or amido and/or imido groups.
  • Particularly preferred detergent additives in this context are polyisobutenyl-substituted succinimides, especially the imides with aliphatic polyamines.
  • Particularly preferred polyamines are diethylenetriamine, tetraethylenepentamine and pentaethylenehexamine, particular preference being given to tetraethylenepentamine.
  • the polyisobutenyl radical has a number-average molecular weight M n of preferably from 500 to 5000, more preferably from 500 to 2000 and in particular of about 1000.
  • the detergent additives mentioned are used in combination with at least one carrier oil in the additive concentrates mentioned.
  • Suitable mineral carrier oils are the fractions obtained in crude oil processing, such as brightstock or base oils having viscosities, for example, from the SN 500 - 2000 class; but also aromatic hydrocarbons, paraffinic hydrocarbons and alkoxyalkanols. Likewise useful is a fraction which is obtained in the refining of mineral oil and is known as "hydrocrack oil” (vacuum distillate cut having a boiling range of from about 360 to 500 0 C, obtainable from natural mineral oil which has been catalytically hydrogenated under high pressure and isomerized and also deparaffinized). Likewise suitable are mixtures of abovementioned mineral carrier oils.
  • suitable synthetic carrier oils are selected from: polyolefins (poly-alpha- olefins or poly(internal olefin)s), (poly)esters, (poly)alkoxylates, polyethers, aliphatic polyether amines, alkylphenol-started polyethers, alkylphenol-started polyether amines and carboxylic esters of long-chain alkanols.
  • suitable polyethers or polyetheramines are preferably compounds com- prising polyoxy-C2-C4-alkylene moieties which are obtainable by reacting C2-C6o-alka- nols, C6-C3o-alkanediols, mono- or di-C2-C3o-alkylamines, Ci-C3o-alkylcyclohexanols or Ci-C3o-alkylphenols with from 1 to 30 mol of ethylene oxide and/or propylene oxide and/or butylene oxide per hydroxyl group or amino group, and, in the case of the polyether amines, by subsequent reductive amination with ammonia, monoamines or polyamines.
  • Such products are described in particular in
  • the polyether amines used may be poly-C2-C6-alkylene oxide amines or functional derivatives thereof. Typical examples thereof are tridecanol butoxylates or isotridecanol butoxylates, isononylphenol butoxylates and also polyisobutenol butoxylates and propoxylates, and also the corresponding reaction products with ammonia.
  • carboxylic esters of long-chain alkanols are in particular esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, as described in particular in DE-A-38 38 918.
  • the mono-, di- or tricarboxylic acids used may be aliphatic or aromatic acids; suitable ester alcohols or polyols are in particular long-chain representatives having, for example, from 6 to 24 carbon atoms.
  • esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, isononanol, isodecanol and isotridecanol, for example di- (n- or isotridecyl) phthalate.
  • suitable synthetic carrier oils are alcohol-started polyethers having from about 5 to 35, for example from about 5 to 30, Cs-C ⁇ -alkylene oxide units, for example selected from propylene oxide, n-butylene oxide and isobutylene oxide units, or mixtures thereof.
  • suitable starter alcohols are long- chain alkanols or phenols substituted by long-chain alkyl in which the long-chain alkyl radical is in particular a straight-chain or branched C ⁇ -Cis-alkyl radical.
  • Preferred examples include tridecanol and nonylphenol.
  • suitable synthetic carrier oils are alkoxylated alkylphenols, as described in DE-A-10 102 913.6.
  • Preferred carrier oils are synthetic carrier oils, particular preference being given to polyethers.
  • a carrier oil When a carrier oil is also incorporated into the additive concentrate, it is added typically in an amount of from 10% by weight to 100% by weight, preferably from 20 to 70% by weight, based in each case on the amount of detergent additive of component (B).
  • inert organic solvents or solvent mixtures of component (C) used in the additive concentrates mentioned are generally those which are selected from hydrocarbons, alcohols, carboxylic esters or mixtures thereof. "Inert” means here that such organic solvents exert no significant interactions, if any, with the active components in the additive concentrates or enter into chemical reactions with them under use conditions. Such inert organic solvents or solvent mixtures are essentially free of further organic compounds with functional groups.
  • Typical hydrocarbon solvents suitable as component (C) are n-pentane, n-hexane, n-heptane, cyclohexane, methylcyclohexane, toluene, xylenes, technical hydrocarbon mixtures such as Solvent Naphtha, as are commercially obtainable, for example, under the name Solvesso® 150, and fuels themselves.
  • Typical alcohols suitable as component (C) are methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol, 2-ethylhexanol and 2-propylheptanol.
  • Carboxylic esters suitable as component (C) are, for example, fatty acid lower alkyl esters, especially fatty acid methyl esters.
  • the cetane number improvers of component (D) are also referred to as ignition or combustion improvers.
  • the component (D) to be used in the additive concentrates mentioned is preferably at least one cetane number improver which is selected from organic nitrates.
  • Such organic nitrates are especially nitrate esters of unsubstituted or substituted, aliphatic or cycloaliphatic alcohols, usually having up to about 10 and in particular having from 2 to 10 carbon atoms.
  • the alkyl group in these nitrate esters may be linear or branched, saturated or unsaturated.
  • nitrate esters are methyl nitrate, ethyl nitrate, n-propyl nitrate, isopropyl nitrate, allyl nitrate, n-butyl nitrate, isobutyl nitrate, sec-butyl nitrate, tert-butyl nitrate, n-amyl nitrate, isoamyl nitrate, 2-amyl nitrate, 3-amyl nitrate, tert-amyl nitrate, n-hexyl nitrate, n-heptyl nitrate, sec-heptyl nitrate, n-octyl nitrate, 2-ethylhexyl nitrate, sec-octyl nitrate, n-nonyl nitrate, n-decyl nitrate, 2-propylh
  • nitrate esters of alkoxy-substituted aliphatic alcohols such as 2-ethoxyethyl nitrate, 2-(2-ethoxyethoxy)ethyl nitrate, 1 -methoxypropyl nitrate or 4-ethoxybutyl nitrate.
  • diol nitrates such as 1 ,6-hexamethylene dinitrate.
  • cetane number improver classes mentioned primary amyl nitrates, primary hexyl nitrates, octyl nitrates and mixtures thereof are preferred.
  • 2-ethylhexyl nitrate as component (D).
  • 2-Ethylhexyl nitrate may be present as the sole cetane number improver or in a mixture with other cetane number improvers.
  • the additive concentrates mentioned may comprise further customary coadditives, especially boosters for the cold flow improvers (A), such as oleic acid- diethylenetriamine reaction products, corrosion inhibitors, deicing agents such as ethylene glycol mono- or dimethyl ethers, demulsifiers, dehazers, antifoams, lubricity improvers, metal deactivators, antioxidants or stabilizers, antistats, metallocenes, markers and/or dyes.
  • boosters for the cold flow improvers (A) such as oleic acid- diethylenetriamine reaction products, corrosion inhibitors, deicing agents such as ethylene glycol mono- or dimethyl ethers, demulsifiers, dehazers, antifoams, lubricity improvers, metal deactivators, antioxidants or stabilizers, antistats, metallocenes, markers and/or dyes.
  • boosters for the cold flow improvers (A) such as oleic acid- diethylenetriamine reaction products, corrosion
  • fuel oil compositions shall be understood to mean middle distillate fuels which boil within the range of 120-500 0 C, renewable fuels and mixtures thereof.
  • middle distillate fuels are in particular diesel fuel, heating oil or kerosene, particular preference being given to heating oil and in particular diesel fuel.
  • renewable fuels are bioethanol and in particular biodiesel.
  • the heating oils are, for example, low-sulfur or sulfur-rich crude oil raffinates or bituminous or brown coal distillates which typically have a boiling range of from 150 to 400 ° C.
  • the heating oils may be standard heating oil according to DIN 51603-1 , which has a sulfur content of from 0.005 to 0.2% by weight, or they are low-sulfur heating oils having a sulfur content of from 0 to 0.005% by weight.
  • Examples of heating oil include in particular heating oil for domestic oil-fired boilers or EL heating oil.
  • the quality requirements for such heating oils are laid down, for example, in DIN 51603-1 (cf. also Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, Volume A12, p. 617 ff . , which is hereby explicitly incorporated by reference).
  • the diesel fuels are, for example, crude oil raffinates which typically have a boiling range from 100 to 400 ° C. These are usually distillates having a 95% point up to 360 ° C or even higher. They may also be so-called "ultra low sulfur diesel” or "city diesel", characterized by a 95% point of, for example, not more than 345 ° C and a sulfur content of not more than 0.005% by weight, or by a 95% point of, for example, 285 ° C and a sulfur content of not more than 0.001 % by weight.
  • suitable diesel fuels also include those obtainable by coal gasification or gas liquefaction ["gas-to-liquid” (“GTL”) fuels] or by biomass liquefaction ["biomass-to-liquid” (“BTL”) fuels]. Also suitable are mixtures of the aforementioned diesel fuels with renewable fuels such as biodiesel or bioethanol.
  • GTL gas-to-liquid
  • BTL biomass liquefaction
  • the diesel fuels are more preferably those having a low sulfur content, i.e. having a sulfur content of less than 0.05% by weight, preferably of less than 0.02% by weight, in particular of less than 0.005% by weight and especially of less than 0.001 % by weight of sulfur.
  • Biodiesel (also referred to as biofuel oil) preferably comprises essentially alkyl esters of fatty acids which derive from vegetable and/or animal oils and/or fats.
  • Alkyl esters are understood to mean typically lower alkyl esters, especially d- to C4-alkyl esters, which are obtainable by transesterifiying the glycerides which occur in vegetable and/or animal oils and/or fats, especially triglycerides, by means of lower alcohols, for example ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, tert- butanol or especially methanol (“FAME": fatty acid methyl esters).
  • FAME fatty acid methyl esters
  • oils which are converted to corresponding alkyl esters and can thus serve as the basis for biodiesel are castor oil, olive oil, peanut oil, palm kernel oil, coconut oil, mustard oil, cottonseed oil and especially sunflower oil, palm oil, soybean oil and rapeseed oil. Further examples include oils which can be obtained from wheat, jute, sesame and the shea tree nut; it is also possible to use arachis oil, jatropha oil and linseed oil.
  • Vegetable fats are likewise usable in principle as a source for biodiesel, but are of minor importance.
  • animal fats and oils which are converted to corresponding alkyl esters and can thus serve as the basis for biodiesel are fish oil, bovine tallow, porcine tallow and similar fats and oils obtained as wastes in the slaughter or utilization of farm animals or wild animals.
  • the parent saturated or unsaturated fatty acids of the vegetable and/or animal oils and/or fats mentioned said fatty acids usually having from 12 to 22 carbon atoms and possibly bearing additional functional groups such as hydroxyl groups, which occur in the alkyl esters are especially lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, elaidic acid, erucic acid and ricinoleic acid, 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 find use 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”).
  • the present invention also provides additive concentrates suitable for additizing fuel oil compositions which consist predominantly of a middle distillate fuel which boils in the range of 120-500 0 C and/or a renewable fuel, said additive concentrate comprising at least one solubilizer of the general formula I
  • R 1 denotes a hydrocarbylene radical having from 1 to 12 carbon atoms or a hydro- carbylene radical which has from 2 to 12 carbon atoms, is interrupted by one or more heteroatoms selected from the group of O, S and N, and may in each case bear one or more functional groups selected from the group of OH, OR 3 , NH 2 , NHR 4 , NR 4 R 5 , COOH, COOR 7 , CONHR 4 and CONR 4 R 5 , where amino groups may also be present in protonated form and carboxylic acid groups also in deprotonated form,
  • X is OH, OR 3 , NH 2 , NHR 4 or NR 4 R 5 , where, in the case that X together with the adjacent carbonyl group is a carboxylic acid radical, this radical is present in deprotonated form and the accompanying cation may be a hydrocarbyl- substituted ammonium cation selected from the group of [HsNR 8 J + , [HbNR 8 R 9 J + and [HNR 8 R 9 R 1Q ] + ,
  • Y is O, S, NH or NR 6 , or, in the case that X is NH 2 or NHR 4 , is a chemical bond to X with formation of an imide structure,
  • R 2 to R 10 are each independently hydrocarbyl radicals having from 1 to 30 carbon atoms
  • R 2 , R 3 , R 4 , R 5 , R 6 and R 7 radicals has at least 4 carbon atoms
  • the additive concentrates mentioned preferably additionally comprise
  • inventive additive concentrates comprise
  • (A) from 1 to 50% by weight, especially from 2 to 40% by weight, in particular from 3 to 20% by weight, of at least one cold flow improver,
  • (B) from 0.5 to 40% by weight, preferably from 0.7 to 20% by weight, especially from 1 to 12% by weight, in particular from 1.5 to 7% by weight, of at least one detergent additive,
  • (C) from 1 to 60% by weight, especially from 3 to 50% by weight, in particular from 5 to 40% by weight, of an inert organic solvent or of a mixture of such solvents and
  • (D) from 0 to 80% by weight, especially from 25 to 75% by weight, in particular from 40 to 70% by weight, of at least one cetane number improver.
  • the additive concentrates mentioned may additionally comprise further ingredients, in which case the sum of all ingredients adds up to 100% by weight.
  • the solubilizers of the general formula I used in accordance with the invention ensure sufficient homogenization of additive concentrates which comprise both cold flow improvers and detergent additives, and also inert organic solvents and if appropriate cetane number improvers, by stabilizing them such that no flaky precipitates or opacity occur in the course of formulation or storage - even in the course of storage over prolonged periods, for example over several weeks - of the additive concentrates.
  • the examples which follow are intended to illustrate this effect of the solubilizers I.
  • Additive concentrates composed of the following components were prepared by mixing:
  • Solubilizer L2 Monoamide formed from succinic acid and tridecylamine (isomer mixture with ⁇ 50 mol% of n-tridecylamine) [HOOC-CH 2 -CH 2 -CO-NH-CI 3 H 27 ]
  • Solubilizer L3 Monoamide formed from n-decylsuccinic acid and tridecylamine (isomer mixture with ⁇ 50 mol% of n-tridecylamine) [HOOC-CH(C I OH 2I )-CH 2 -CO-NH-C I3 H 27 ]
  • Cold flow improver A1 Commercial reaction product formed from 1 mol of ethylenediaminetetraacetic acid and 4 mol of hydrogenated ditallow fat amine [cold flow improver of group (Ad), especially effective as a paraffin dispersant (“WASA”)]
  • Cold flow improver A2 Commercial ethylene-vinyl acetate-acrylate copolymer [cold flow improver of group (Aa)]
  • Detergent additive B1 Commercial polyisobutylenesuccinamide based on an aliphatic polyamine [detergent component with the (Bh) moiety]
  • Solvent C1 Solvent Naphtha (Solvesso® 150)
  • Booster F1 Customary oleic acid-diethylenetriamine reaction product
  • the degree of homogenization of the additive concentrates prepared was assessed visually by the following rating scale:
  • compositions of the additive concentrate prepared and the assessment of their degree of homogenization according to the above rating scale is evident from the table below (the composition of the additive concentrates is reported in each case in % by weight).
  • L1 or at least the majority of L1 was added as the last component.
  • the state of the additive concentrates thus prepared which was rated remained stable in each case for a prolonged period.

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Abstract

La présente invention concerne une composition d'huile combustible résistante au froid comprenant une proportion majeure en poids d'un combustible de distillat moyen qui bout dans la plage de 120 à 500 °C et des proportions mineures en poids de (A) au moins un agent améliorant l'écoulement à froid, (B) au moins un additif détergent et (C) au moins un agent solubilisant à froid I de formule (I), qui possède au moins un radical ayant au moins 4 atomes de carbone.
PCT/EP2009/057076 2008-06-12 2009-06-09 Utilisation d'agents solubilisants pour l'homogénéisation de concentrés d'additifs WO2009150145A1 (fr)

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WO2023057748A1 (fr) * 2021-10-04 2023-04-13 Innospec Fuel Specialties Llc Améliorations de carburants
EP4166633A1 (fr) * 2021-10-15 2023-04-19 Innospec Fuel Specialties LLC Améliorations de carburants

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EP2417229B1 (fr) * 2009-04-07 2013-10-02 Basf Se 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
WO2014067748A1 (fr) 2012-11-02 2014-05-08 Evonik Industries Ag Formulations de distillat moyen contenant des copolymères de méthacrylate d'alkyle dispersifs exempts de soufre
CN104854222B (zh) * 2012-12-20 2018-04-10 阿彻丹尼尔斯米德兰德公司 从生物衍生的羧酸酯生产生物燃料
US20230151290A1 (en) * 2020-03-30 2023-05-18 China Petroleum & Chemical Corporation Lubricity modifier for fuels and application thereof

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WO2023057748A1 (fr) * 2021-10-04 2023-04-13 Innospec Fuel Specialties Llc Améliorations de carburants
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EP4166633A1 (fr) * 2021-10-15 2023-04-19 Innospec Fuel Specialties LLC Améliorations de carburants

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