WO2013174631A1 - Utilisation d'un produit réactionnel d'acides carboxyliques avec des polyamines aliphatiques pour l'amélioration ou l'augmentation de la séparation d'eau et de mazouts - Google Patents

Utilisation d'un produit réactionnel d'acides carboxyliques avec des polyamines aliphatiques pour l'amélioration ou l'augmentation de la séparation d'eau et de mazouts Download PDF

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WO2013174631A1
WO2013174631A1 PCT/EP2013/059052 EP2013059052W WO2013174631A1 WO 2013174631 A1 WO2013174631 A1 WO 2013174631A1 EP 2013059052 W EP2013059052 W EP 2013059052W WO 2013174631 A1 WO2013174631 A1 WO 2013174631A1
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weight
acid
fuel oils
use according
anhydride
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PCT/EP2013/059052
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English (en)
Inventor
Maxim Peretolchin
Günter OETTER
Harald BÖHNKE
Markus Hansch
Ludwig Völkel
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Basf Se
Basf Schweiz Ag
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Application filed by Basf Se, Basf Schweiz Ag filed Critical Basf Se
Priority to CN201380035627.4A priority Critical patent/CN104411805A/zh
Priority to KR20147036114A priority patent/KR20150021533A/ko
Priority to CA2874311A priority patent/CA2874311A1/fr
Priority to RU2014152461A priority patent/RU2014152461A/ru
Priority to AU2013265587A priority patent/AU2013265587A1/en
Priority to EP13720367.5A priority patent/EP2855633A1/fr
Publication of WO2013174631A1 publication Critical patent/WO2013174631A1/fr
Priority to ZA2014/09463A priority patent/ZA201409463B/en

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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10G33/00—Dewatering or demulsification of hydrocarbon oils
    • C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means
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    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
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    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
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    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/202—Heteroatoms content, i.e. S, N, O, P
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    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C10G2300/301—Boiling range
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    • C10L1/22—Organic compounds containing nitrogen
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    • C10L1/224—Amides; Imides carboxylic acid amides, imides
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    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
    • C10L2200/0446—Diesel
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Definitions

  • the present invention relates to the use of a reaction product (RP) of (A) at least one saturated or unsaturated aliphatic mono- or polycarboxylic acid with 10 to 200 carbon atoms or an anhydride thereof with (B) at least one aliphatic polyamine comprising 2 to 10 nitrogen atoms and 0 to 2 hydroxyl groups exhibiting at least one primary or secon- dary amino group, for improving or boosting the separation of water from fuel oils which comprise (C) at least one additive with detergent action.
  • RP reaction product of (A) at least one saturated or unsaturated aliphatic mono- or polycarboxylic acid with 10 to 200 carbon atoms or an anhydride thereof with (B) at least one aliphatic polyamine comprising 2 to 10 nitrogen atoms and 0 to 2 hydroxyl groups exhibiting at least one primary or secon- dary amino group, for improving or boosting the separation of water from fuel oils which comprise (C) at least one additive with detergent action.
  • Fuel oils such as middle distillates, e.g. diesel fuels, heating oils or jet fuels, often contain small amounts of water, typically in the region of from several parts per millions up to several per cent by weight, due to condensation of water into the cold fuel oils and into the storage tanks and pipelines during transport and storage. This amount of water partly separates as a layer at the bottom of the storage tank and partly is emulsified in the fuel oil. The presence of water is undesired as it can cause severe problems on transport and on use in combustion engines and heating devices.
  • German laid open Patent Application 1 645 705 discloses to use of amides of carboxylic acids to dehaze hydrocarbon mixtures, e.g. heating oil and diesel fuel.
  • the said amides are for example prepared from di-, tri- and polyamines like ethylene- diamine, propylenediamine, diethylenetriamine, tetraethylenepentamine, dipropylene- triamine, methyldipropylenetriamine, diaminobutane or polyamylenepolyamine, and higher fatty acids, e.g. oleic acid, however, without giving any stoichiometric ratios for preparation.
  • Chinese Patent Application 102277212 A (2) relates to a diesel performance additive which is a mixture of tall oil fatty acids, an oleic acid amide and a naphthenic acid imidazoline.
  • the said three-component additive is recommended as an emulsifying agent to dehaze and clear up diesel fuels.
  • a corresponding oleic acid amide is prepared by reaction of oleic acid with diethylenetriamine in the stoichiometric ratio of 1 : 1.75. Similar to (1 ) above, no hint is given to any possible interactions or synergistic interactions of the said amides with further middle distillate performance additives such as additives with detergent action or further additives with dehazing action.
  • As the teaching of (2) also refers to dehaze the diesel fuels, i.e. to clear them up by generating hydrocarbon-water-emulsions, such technical solution may only work with relatively small amounts of water; this method will fail with larger amounts of water.
  • Dehazing as referred to in the cited documents above and as generally understood in the art shall mean clearing up water-containing hydrocarbons or diesel fuels, respectively, by generating clear hydrocarbon-water-emulsions ("emulsification") and shall not include separating water in separate phase (“demulsification”), thus enabling to remove the water by phase separation.
  • emulsification clear hydrocarbon-water-emulsions
  • demulsification separating water in separate phase
  • Such additives should interact with other performance additives present in the fuel oils in an advantageous way.
  • the tendency of modern additives with detergent action to support the undesired formation and stabilization of fuel oil-water-emulsions should be counteracted.
  • reaction product for improving or boosting the separation of water from fuel oils comprising one or more additives with detergent action.
  • water present in the fuel oils is separated as a layer at the bottom of a separation device and, thereafter, can be easily removed.
  • the water content in fuel oils which can be removed in this way is normally from about 200 ppm by weight to about 10% by weight, especially from about 1000 ppm by weight to about 5% by weight.
  • Emulsifying water in the fuel oil by interaction with (RP) occurs only to a negligible minor amount.
  • the reaction product (RP) improves and completes the phase separation of water from the fuel oils which occurs with larger amounts of water present in the fuel oils already without any performance additive but in an incomplete way. Furthermore, (RP) boosts the phase separation of water from fuel oils if other surface active additives, especially certain commercially available dehazers, are already present in the fuel oils. Astonishingly, the interaction between (RP) and certain commercially available dehazers which are by nature emulsifying additives also leads to an improved demulsifying and water phase separating action.
  • Reactant (A) for producing (RP) is a saturated or unsaturated aliphatic mono- or polycarboxylic acid with 10 to 200, preferably 14 to 200, more preferably 16 to 170, most preferably 18 to 100 carbon atoms, or a mixture of such acids.
  • the carboxylic acids for (A) exhibit one or more, e.g. two or three, linear or branched alkyl or alkenyl groups of each at least 10, preferably at least 14, more preferably at least 16, most preferably at least 18 carbon atoms.
  • the carboxylic acids for (A) normally do not comprise cyclic structural units like cyclopentylene or cyclohexylene groups.
  • the carboxylic acids for (A) may comprise monocarboxylic acids or their anhydrides, especially saturated or unsaturated long-chain fatty acids, e.g. lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid and elaidic acid. Oleic acid is especially preferred.
  • the carboxylic acids for (A) may comprise polycarboxylic acids, especially dicarboxylic acids, or their anhydrides which exhibit long-chain alkylene or alkenylene bridging groups between the carboxylic groups with at least 8, preferably at least 12, more preferably at least 14, most preferably at least 16, or one or more side-chain linear or branched alkyl or alkenyl radicals with at least 10, preferably at least 14, more preferably at least 16, most preferably at least 18 carbon atoms.
  • Suitable side-chain branched alkyl and alkenyl radicals are for example polyisobutyl- and polyisobutenyl radicals.
  • reactant (A) comprises at least one saturated or unsaturated aliphatic monocarboxylic acid with 14 to 200, preferably 16 to 170, more preferably 18 to 100 carbon atoms.
  • Reactant (B) for producing (RP) is a linear or branched aliphatic polyamine comprising 2 to 10 nitrogen atoms and 0 to 2 hydroxyl groups exhibiting at least one primary or secondary amino group.
  • (B) comprises at least two amino groups which are primary or secondary amino groups.
  • the aliphatic polyamines for (B) are typically polyaminoalcohols of general formulas HO-(X-NH) p -H or HO-(Y-NH) q -Y-OH, in which p and q independently from each other stand for a number of from 2 to 10 and X and Y independently from each other represent 1 ,2-ethylene, 1 ,3-propylene, 1 ,2-propylene or 1 ,4-butylene.
  • (B) comprises especially polyalkyleneamines in which the nitrogen atoms are bridged by linear or branched alkylene groups with each 1 to 12, preferably 2 to 8 carbon atoms.
  • the aliphatic polyamines for (B) normally do not comprise cyclic bridging units like cyclopentylene or cyclohexylene groups. Tertiary amino groups may also be present.
  • reactant (B) comprises at least one polyalkyleneamine of general formula H2N-(A-NH) n -H in which A represents 1 ,2- ethylene, 1 ,3-propylene, 1 ,2-propylene or 1 ,4-butylene and n stands for a number of from 1 to 5.
  • Typical examples for such polyalkyleneamines are ethylene-1 ,2-diamine, propylene-1 ,3-diamine, propylene-1 ,2-diamine, diethylenetriamine, triethylentetramine, tetraethylenepentamine, pentaethylenehexamine, dipropylenetriamine, N-methyldipro- pylenetriamine and butylene-1 ,4-diamine.
  • the reaction product (RP) of the carboxylic acids (A) and the aliphatic polyamines (B) may be the corresponding ammonium salts, the corresponding amides or imides, the corresponding mixed ammonium salts / amides or imides, and/or follow-up products of the said amides or imides such as products generated by intramolecular or intermole- cular cyclization (especially when higher temperatures are applied during the synthe- sis), e.g. products with imidazoline structural units formed by ring cleavage between a carbonyl atom of an amide unit and a secondary amine group.
  • RP is usually a technical product it is in most cases a mixture of different species of the above amides or imides, mixed ammonium salts / amides or imides, and/or follow-up products of the said amides or imides.
  • reactant (B) exhibits at least two amino groups which are primary or secondary amino groups, and reactants (A) and (B) are reacted in a molar ratio of from 1 .1 : 1 to 7 : 1 , preferably of from 1 .5 : 1 to 6 :1 , more preferably of from 1.7 : 1 to 5 : 1 , most preferably of from 1.8 : 1 to 4 : 1 .
  • (B) may exhibit 2 primary amino group and 0, 1 , 2, 3 or 4 secondary amino groups.
  • a suitable reaction product (RP) is made for example from oleic acid and diethylenetriamine in a molar ratio of 1 .83 : 1 exhibiting a structure with an imidazoline ring for its main component.
  • Additives with detergent action of component (C) refer, in the context of the present invention, to those compounds whose effect in an internal combustion engine or in a heating device, especially a diesel engine, consists predominantly or at least essentially of eliminating and/or preventing deposits.
  • the detergents are preferably amphiphilic substances which have at least one hydrophobic hydrocarbyl radical having a number-average molecular weight (M n ) of 85 to 20.000, especially of 300 to 5000, and in particular of 500 to 2500, and at least one polar moiety.
  • the fuel oils comprise at least one additive component with detergent action (C) which is selected from
  • nitrogen compounds quaternized in the presence of an acid or in an acid-free manner obtainable by addition of a compound comprising at least one oxygen- or nitrogen-containing group reactive with an anhydride and additionally at least one quaternizable amino group onto a polycarboxylic anhydride compound and subsequent quaterniza-tion;
  • derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
  • the moieties with hydroxyl and/or amino and/or amido and/or imido groups are for example carboxylic acid groups, acid amides, acid amides of di- or polyamines, which, as well as the amide function, also have free amine groups, succinic acid derivatives with an acid and an amide function, carboxyimides with monoamines, carboxyimides with di- or polyamines, which, as well as the imide function, also have free amine groups, and diimides, which are formed by the reaction of di- or polyamines with two succinic acid derivatives.
  • Such fuel additives are described especially in US-A 4 849 572.
  • Nitrogen compounds quaternized in the presence of an acid or in an acid-free manner according to the above group (ii) are obtainable by addition of a compound which comprises at least one oxygen- or nitrogen-containing group reactive with an anhydride and additionally at least one quaternizable amino group onto a polycarboxylic anhydride compound and subsequent quaternization, especially with an epoxide, e.g. styrene or propylene oxide, in the absence of free acid, as described in WO
  • Suitable compounds having at least one oxygen- or nitrogen-containing group reactive with anhydride and additionally at least one quaternizable amino group are especially polyamines having at least one primary or secondary amino group and at least one tertiary amino group.
  • Useful polycarboxylic anhydrides are especially dicarboxylic acids such as succinic acid, having a relatively long-chain hydrocarbyl substituent, preferably having a number-average molecular weight M n for the hydrocarbyl substituent of 200 to 10.000, in particular of 350 to 5000.
  • Such a quaternized nitrogen compound is, for example, the reaction product, obtained at 40°C, of polyisobutenylsuccinic anhydride, in which the polyisobutenyl radical typically has an M n of 1000, with 3- (dimethylamino)propylamine, which constitutes a polyisobutenylsuccinic monoamide and which is subsequently quaternized with styrene oxide or propylene oxide in the absence of free acid at 70°C.
  • Polytetrahydrobenzoxazines and bistetrahydrobenzoxazines according to the above group (iii) are described in EP patent application 10 194 307.4.
  • Such polytetrahydrobenzoxazines and bistetrahydrobenzoxazines are obtainable by successively reacting, in a first reaction step, a Ci- to C2o-alkylenediamine having two primary amino functions, e.g. 1 ,2-ethylenediamine, with a Ci- to Ci2-aldehyde, e.g.
  • a tert-octyl, n-nonyl, n-dodecyl or polyisobutyl radical having an M n of 1000, in a stoichiometric ratio relative to the originally used alkylenediamine of 1.2:1 to 3:1 at a temperature of 30 to 120°C and optionally in a third reaction step heating the bistetrahydrobenzoxazine thus obtained to a temperature of 125 to 280°C for at least 10 minutes.
  • reaction product (RP) is preferably used together with quarternized nitrogen compounds (ii) for component (C). Furthermore, the present reaction product (RP) and the at least one additive with detergent action for component (C) exhibit superior performance - even in the sense of synergism - in improving and/or boosting the separation of water from fuel oils when applied together with at least one dehazer exhibiting emulsifying action on its own when used alone as additive component (D) selected from
  • alkoxylation copolymers of ethylene oxide, propylene oxide, butylene oxide, styrene oxide and/or other oxides e.g. epoxy based resins
  • Dehazer components (iv) and (v) are normally commercially available products, e.g. the dehazer products available from Baker Petrolite under the brand name of Tolad® such as Tolad® 2898, 9360K, 9348, 9352K or 9327.
  • the fuel oils additionally comprise as additive component (E) at least on cetane number improver.
  • Cetane number improvers used are typically organic nitrates. Such organic nitrates are especially nitrate esters of unsubstituted or substituted aliphatic or cycloaliphatic alcohols, usually having up to about 10, in particular having 2 to 10 carbon atoms.
  • the alkyl group in these nitrate esters may be linear or branched, and saturated or unsaturated.
  • Typical examples of such 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 nit
  • nitrate esters of alkoxy-substituted aliphatic alcohols such as 2-ethoxyethyl nitrate, 2-(2-ethoxy- ethoxy)ethyl nitrate, 1 -methoxypropyl nitrate or 4-ethoxybutyl nitrate.
  • diol nitrates such as 1 ,6-hexamethylene dinitrate.
  • cetane number improver classes mentioned preference is given to primary amyl nitrates, primary hexyl nitrates, octyl nitrates and mixtures thereof.
  • 2-ethylhexyl nitrate is present in the fuel oils as the sole cetane number improver or in a mixture with other cetane number improvers.
  • fuel oils means prefereably middle distillate fuels, especially diesel fuels.
  • heating oils, jet fuels and kerosene shall also be encompassed.
  • Diesel fuels or middle distillate fuels are typically mineral oil raffinates which generally have a boiling range from 100 to 400°C. These are usually distillates having a 95% point up to 360°C or even higher. However, these may also be what is 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.
  • diesel fuels obtainable by refining, the main constituents of which are relatively long-chain paraffins, those obtainable in a synthetic way by coal gasification or gas liquefaction ["gas to liquid” (GTL) fuels] are suitable, too.
  • mixtures of the aforementioned diesel fuels with renewable fuels (biofuel oils) such as biodiesel or bioethanol.
  • biofuel oils renewable fuels
  • diesel fuels with low sulfur content i.e. with a sulfur content of less than 0.05% by weight, preferably of less than 0.02% by weight, particularly of less than 0.005% by weight and especially of less than 0.001 % by weight of sulfur.
  • the instant reaction product (RP) is used together with the aforementioned components (C), (D) and, if desired (E), in fuel oils which consist
  • the instant reaction product (RP) can also be used together with the aforementioned components (C), (D) and, if desired (E), in fuel oils which consist exclusively of middle distillates of fossil origin and/or of synthetic origin and/or of vegetable and/or animal origin, which are essentially hydrocarbon mixtures and are free of fatty acid esters.
  • Fuel oil component (a) is usually also referred to as "biodiesel”.
  • This preferably comprises essentially alkyl esters of fatty acids which derive from vegetable and/or animal oils and/or fats.
  • Alkyl esters typically refer to lower alkyl esters, especially Ci- to C 4 - alkyl esters, which are obtainable by transesterifying 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").
  • FAME methanol
  • oils which can be converted to corresponding alkyl esters and can thus serve as the basis of 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 shea tree nut; it is additionally also possible to use arachis oil, jatropha oil and linseed oil. The extraction of these oils and the conversion thereof to the alkyl esters are known from the prior art or can be inferred therefrom.
  • Vegetable fats can in principle likewise be used as a source for biodiesel, but play a minor role.
  • animal oils and fats which can be converted to corresponding alkyl esters and can thus serve as the basis of 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 said vegetable and/or animal oils and/or fats which usually have 12 to 22 carbon atoms and may bear an additional functional group such as hydroxyl groups, and 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/or ricinoleic acid.
  • 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”).
  • PME palm oil methyl ester
  • SME soybean oil methyl ester
  • RME rapeseed oil methyl ester
  • the fuel oil component (b) shall be understood to mean the abovementioned middle distillate fuels, especially diesel fuels, especially those which boil in the range from 120 to 450°C.
  • the instant reaction product (RP) is used together with the aforementioned components (C), (D) and, if desired (E), in fuel oils which have at least one of the following properties:
  • Polycyclic aromatic hydrocarbons in ( ⁇ ) shall be understood to mean polyaromatic hydrocarbons according to standard EN 12916. They are determined according to this standard.
  • the fuel oils comprise said reaction product (RP) in the context of the present invention generally in an amount of from 1 to 1000 ppm by weight, preferably of from 5 to 500 ppm by weight, more preferably of from 3 to 300 ppm by weight, most preferably of from 5 to 200 ppm by weight, for example of from 10 to 100 ppm by weight.
  • the additive with detergent action (C) or a mixture of a plurality of such additives with detergent action is present in the fuel oils typically in an amount of from 10 to 2000 ppm by weight, preferably of from 20 to 1000 ppm by weight, more preferably of from 50 to 500 ppm by weight, most preferably of from 30 to 250 ppm by weight, for example of from 50 to 150 ppm by weight.
  • One or more dehazers as additive component (D), if any, are present in the fuel oils generally in an amount of from 0.5 to 100 ppm by weight, preferably of from 1 to 50 ppm by weight, more preferably of from 1 .5 to 40 ppm by weight, most preferably of from 2 to 30 ppm by weight, for example of from 3 to 20 ppm by weight.
  • the cetane number improver (E) or a mixture of a plurality of cetane number improvers is present in the fuel oils normally in an amount of form 10 to 10.000 ppm by weight, preferably of from 20 to 5000 ppm by weight, more preferably of from 50 to 2500 ppm by weight, most preferably of from 100 to 1000 ppm by weight, for example of from 150 to 500 ppm by weight.
  • Subject matter of the present invention is also a fuel additive concentrate suitable for use in fuel oils, especially in diesel fuel, comprising
  • RP 0.01 to 40% by weight, preferably 0.05 to 20% by weight, more preferably 0.1 to 10% by weight, of a reaction product of (A) at least one saturated or unsaturated aliphatic mono- or polycarboxylic acid with 10 to 200 carbon atoms or an anhydride thereof with (B) at least one aliphatic polyamine comprising 2 to 10 nitrogen atoms and 0 to 2 hydroxyl groups exhibiting at least one primary or secondary amino group; (C) 5 to 40% by weight, preferably 10 to 35% by weight, more preferably 15 to 30% by weight, of at least one additive with detergent action selected from
  • nitrogen compounds quaternized in the presence of an acid or in an acid-free manner obtainable by addition of a compound comprising at least one oxygen- or nitrogen-containing group reactive with an anhydride and additionally at least one quaternizable amino group onto a polycarboxylic anhydride compound and subsequent quaternization
  • alkoxylation copolymers of ethylene oxide, propylene oxide, butylene oxide, styrene oxide and/or other oxides e.g. epoxy based resins
  • (F) 0 to 50% by weight, preferably 5 to 50% by weight, more preferably 10 to 40% by weight, of at least one solvent or diluent.
  • Said fuel oils such as diesel fuels, or said mixtures of biofuel oils and middle distillates of fossil, synthetic, vegetable or animal origin, may comprise, in addition to reaction product (RP) and components (C) and, if any (D) and (E), as coadditives further customary additive components in amounts customary therefor, especially cold flow improvers, corrosion inhibitors, further demulsifiers, antifoams, antioxidants and stabilizers, metal deacti-vators, antistats, lubricity improvers, dyes (markers) and/or diluents and solvents.
  • Said fuel additive concentrates may also comprise certain of the above coadditives in amounts customary therefor, e.g.
  • Cold flow improvers suitable as further coadditives are, for example, copolymers of ethylene with at least one further unsaturated monomer, in particular ethylene-vinyl acetate copolymers.
  • Corrosion inhibitors suitable as further coadditives are, for example, succinic esters, in particular with polyols, fatty acid derivatives, for example oleic esters, oligomerized fatty acids and substituted ethanolamines.
  • demulsifiers suitable as further coadditives are, for example, the alkali metal and alkaline earth metal salts of alkyl-substituted phenol- and naphthalenesulfonates and the alkali metal and alkaline earth metal salts of fatty acid, and also alcohol alkoxylates, e.g. alcohol ethoxylates, phenol alkoxylates, e.g. tert-butylphenol ethoxylates or tert-pentylphenol ethoxylates, fatty acids, alkylphenols, condensation products of ethylene oxide and propylene oxide, e.g. ethylene oxide-propylene oxide block copolymers, polyethyleneimines and polysiloxanes.
  • alcohol alkoxylates e.g. alcohol ethoxylates
  • phenol alkoxylates e.g. tert-butylphenol ethoxylates or tert-pentylphenol eth
  • Antifoams suitable as further coadditives are, for example, polyether-modified polysiloxanes.
  • Antioxidants suitable as further coadditives are, for example, substituted phenols, e.g. 2,6-di-tert-butylphenol and 2,6-di-tert-butyl-3-methylphenol, and also phenylene- diamines, e.g. N,N'-di-sec-butyl-p-phenylenediamine.
  • Metal deactivators suitable as further coadditives are, for example, salicylic acid derivatives, e.g. N,N'-disalicylidene-1 ,2-propanediamine.
  • a lubricity improver suitable as a further coadditive is, for example, glyceryl mono- oleate.
  • Suitable solvents and diluents are, for example, nonpolar organic solvents, especially aromatic and aliphatic hydrocarbons, for example toluene, xylenes, "white spirit" and the technical solvent mixtures of the designations Shellsol® (manufactured by Royal Dutch/Shell Group), Exxol® (manufactured by ExxonMobil) and Solvent Naphtha.
  • nonpolar organic solvents especially aromatic and aliphatic hydrocarbons, for example toluene, xylenes, "white spirit” and the technical solvent mixtures of the designations Shellsol® (manufactured by Royal Dutch/Shell Group), Exxol® (manufactured by ExxonMobil) and Solvent Naphtha.
  • polar organic solvents in particular alcohols such as 2-ethylhexanol, decanol and isotridecanol.
  • the test was carried through in a commercially available diesel fuel composed of 100% of middle distillates of fossil origin (“DF1 ”) an in a commercially available biodiesel containing diesel fuel composed of 90% by weight of middle distillates of fossil origin and 10% by weight of FAME (“DF2").
  • DF1 middle distillates of fossil origin
  • DF2 biodiesel containing diesel fuel composed of 90% by weight of middle distillates of fossil origin and 10% by weight of FAME
  • RP1 was the reaction product made from oleic acid and diethylenetriamine in a molar ratio of 1 .83 : 1 exhibiting a structure with an imidazoline ring for its main component.
  • RP2 was the reaction product made from oleic acid and tetraethylenepentamine in a molar ratio of 2.0 : 1.
  • RP 3 was the reaction product made from oleic acid and tetraethylenepentamine in a molar ratio of 3.5 : 1.
  • concentration of said compounds RP1 , RP2 and RP3 in the 80 ml DF1 and DF2, respectively, is given in the table below, when present.
  • the additive with detergent action (C) used was a compound of group (ii), i.e. the reaction product, obtained at 40°C, of polyisobutenylsuccinic anhydride, in which the polyisobutenyl radical has an M n of 1000, with 3-(dimethylamino)propylamine, which constitutes a polyisobutenylsuccinic monoamide and which is subsequently quarter- nized with propylene oxide in the absence of free acid at 70°C.
  • concentration of said compound C(ii) in the 80 ml DF1 and DF2, respectively, is given in the table below, when present.
  • the dehazer (D) used was a compound of group (v), i.e.

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Abstract

L'invention porte sur un produit réactionnel d'acides monocarboxyliques ou polycarboxyliques saturés ou insaturés avec des polyamines aliphatiques pour l'amélioration ou l'augmentation de la séparation d'eau et de mazouts qui comprennent des additifs ayant un effet détersif. L'invention porte également sur un concentré d'additif pour carburant comprenant ledit produit réactionnel, certains additifs présentant un effet détersif et éventuellement des agents diminuant le trouble, des agents améliorant l'indice de cétane et des solvants ou diluants.
PCT/EP2013/059052 2012-05-25 2013-04-30 Utilisation d'un produit réactionnel d'acides carboxyliques avec des polyamines aliphatiques pour l'amélioration ou l'augmentation de la séparation d'eau et de mazouts WO2013174631A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
CN201380035627.4A CN104411805A (zh) 2012-05-25 2013-04-30 羧酸与脂族多胺的反应产物用于改进或促进水从燃料油中分离的用途
KR20147036114A KR20150021533A (ko) 2012-05-25 2013-04-30 연료유로부터의 물의 분리를 개선 또는 신장시키기 위한 카르복실산과 지방족 폴리아민의 반응 생성물의 용도
CA2874311A CA2874311A1 (fr) 2012-05-25 2013-04-30 Utilisation d'un produit reactionnel d'acides carboxyliques avec des polyamines aliphatiques pour l'amelioration ou l'augmentation de la separation d'eau et de mazouts
RU2014152461A RU2014152461A (ru) 2012-05-25 2013-04-30 Применение продукта реакции карбоновых кислот с алифатическими полиаминами для улучшения или стимулирования отделения воды от жидких топлив
AU2013265587A AU2013265587A1 (en) 2012-05-25 2013-04-30 Use of a reaction product of carboxylic acids with aliphatic polyamines for improving or boosting the separation of water from fuel oils
EP13720367.5A EP2855633A1 (fr) 2012-05-25 2013-04-30 Utilisation d'un produit réactionnel d'acides carboxyliques avec des polyamines aliphatiques pour l'amélioration ou l'augmentation de la séparation d'eau et de mazouts
ZA2014/09463A ZA201409463B (en) 2012-05-25 2014-12-22 Use of a reaction product of carboxylic acids with aliphatic polyamines for improving or boosting the separation of water from fuel oils

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CN104479733A (zh) * 2014-12-29 2015-04-01 江苏健神生物农化有限公司 油质抗菌净化剂及其制备方法
US9475743B2 (en) 2013-03-13 2016-10-25 Wintershall Holding GmbH Process for the preparation of substituted TRIS(2-hydroxyphenyl)methane
US9556395B2 (en) 2013-03-11 2017-01-31 Basf Se Use of polyalkoxylates in lubricant compositions
US10414988B2 (en) 2015-12-02 2019-09-17 Ecolab Usa Inc. Methods of treating a stream comprising crude oil and water

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BR112016028067A2 (pt) * 2014-05-30 2017-08-22 Lubrizol Corp Amida/éster de alto peso molecular contendo sais de amônio quaternário
AU2015267144B2 (en) * 2014-05-30 2019-06-13 The Lubrizol Corporation Low molecular weight amide/ester containing quaternary ammonium salts

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US2225189A (en) * 1938-07-29 1940-12-17 Truman B Wayne Process and reagent for resolving emulsions
DE1645705A1 (de) * 1967-10-13 1970-07-16 Basf Ag Mittel zum Enttrueben von Kohlenwasserstoffgemischen
EP0074077A2 (fr) * 1981-09-05 1983-03-16 Hoechst Aktiengesellschaft Bisimidazolines, procédé pour leur préparation et leur application
EP0383550A2 (fr) * 1989-02-14 1990-08-22 Nippon Light Metal Co., Ltd. Electrode de formation d'un plasma et son procédé d'utilisation

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Publication number Priority date Publication date Assignee Title
US2225189A (en) * 1938-07-29 1940-12-17 Truman B Wayne Process and reagent for resolving emulsions
DE1645705A1 (de) * 1967-10-13 1970-07-16 Basf Ag Mittel zum Enttrueben von Kohlenwasserstoffgemischen
EP0074077A2 (fr) * 1981-09-05 1983-03-16 Hoechst Aktiengesellschaft Bisimidazolines, procédé pour leur préparation et leur application
EP0383550A2 (fr) * 1989-02-14 1990-08-22 Nippon Light Metal Co., Ltd. Electrode de formation d'un plasma et son procédé d'utilisation

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9556395B2 (en) 2013-03-11 2017-01-31 Basf Se Use of polyalkoxylates in lubricant compositions
US9475743B2 (en) 2013-03-13 2016-10-25 Wintershall Holding GmbH Process for the preparation of substituted TRIS(2-hydroxyphenyl)methane
CN104479733A (zh) * 2014-12-29 2015-04-01 江苏健神生物农化有限公司 油质抗菌净化剂及其制备方法
CN104479733B (zh) * 2014-12-29 2016-11-23 烟台史密得机电设备制造有限公司 油质抗菌净化剂及其制备方法
US10414988B2 (en) 2015-12-02 2019-09-17 Ecolab Usa Inc. Methods of treating a stream comprising crude oil and water

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