Classifications

• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/146—Macromolecular compounds according to different macromolecular groups, mixtures thereof
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
  • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
  • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
  • C10L1/1966—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof poly-carboxylic
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2366—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amine groups
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2368—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing heterocyclic compounds containing nitrogen in the ring

Definitions

• the present invention relates to petroleum middle distillates which contain small amounts of a conventional flow improver based on ethylene and copolymers of ethylenically unsaturated carboxylic acid esters of long-chain n-alkanols with long-chain alkyl vinyl ethers and are distinguished by improved flow properties in the cold.
• Middle distillates such as gas oils, diesel oils or heating oils, which are obtained from petroleum by distillation, have different levels of paraffins depending on the origin of the crude oil and depending on the processing method in the refinery.
• the proportion of long-chain n-paraffins in particular determines the cold flow behavior of such distillates.
• the n-paraffins Upon cooling, the n-paraffins separate out as platelet-shaped, interlocking crystals that build up a three-dimensional network (house of cards structure), in which large quantities of still liquid distillate are enclosed and immobilized.
• the crystallization of the n-paraffins is accompanied by a decrease in fluidity and an increase in viscosity. This makes it difficult to supply middle distillates to the combustion units, the failed paraffins clog upstream filters, so that in extreme cases the supply can completely stop.
• ethylene copolymers especially copolymers of ethylene and unsaturated esters, such as those e.g. are described in DE-A-21 02 469 or EP-A-84 148.
• DE-A-20 47 448 describes the addition of a mixture consisting of polyvinyl ethers and ethylene-vinyl acetate copolymers to paraffin-based crude oils.
• EP-A-360 419 describes middle distillates which contain polymers of vinyl ethers with hydrocarbon radicals of 1 to 17 carbon atoms. Alkyl acrylates or methacrylates are mentioned as comonomers. In the examples, however, only polymers from alkyl vinyl ethers with up to 4 carbon atoms in the side chain are described. These C i to C 4 vinyl ethers are copolymerized with maleic or fumaric acid derivatives. Examples of copolymers with acrylic acid derivatives are not given. The claimed additives can be used together with other flow improvers.
• the weight ratio of monomers according to formula I to monomers according to formula II is between 10:90 and 95: 5, preferably between 40:60 and 95: 5 and particularly preferably between 60:40 and 90:10 and the ratio of flow improver A to copolymer B is between 40:60 and 95: 5, preferably between 60:40 and 95: 5 and particularly preferably between 70:30 and 90:10.
• the alkyl radicals R 2 and R 3 are preferably straight-chain and unbranched. However, up to 20% by weight of cyclic and / or branched portions can also be present.
• Examples of monomers according to formula 1 are n-octyl (meth) acrylate, n-decyl (meth) acrylate, n-dodecyl (meth) acrylate, n-tetradecyl (meth) acrylate, n-hexadecyl (meth) acrylate and n- Octadecyl (meth) acrylate and mixtures thereof.
• Examples of monomers according to formula II are n-octadecyl vinyl ether, n-eicosyl vinyl ether, n-docosyl vinyl ether, n-tetracosyl vinyl ether, n-hexacosyl vinyl ether and n-octacosyl vinyl ether and mixtures thereof.
• the copolymers B consist of at least 70% by weight of monomers according to formulas I and II.
• other ethylenically unsaturated monomers can also be present, such as, for example, styrene, alkylstyrenes, straight-chain or branched olefins with 2 to 16 Carbon atoms, vinyl esters of C 1 - to C s -carboxylic acids, acrylonitrile, N-alkyl-substituted acrylamides, N-containing, ethylenically unsaturated heterocycles such as vinylpyrrolidone, vinylimidazole or vinylpyridine, hydroxyl- or amino group-containing monomers such as butanediol monoacrylate, hexanediol monoacrylate, dimanediol monoacrylate, dimethylethylaminoethylamate, (Meth) acrylic acid esters from C 1 - to C 8 -alkan
• Examples of flow improvers A are the polymers already mentioned, described in DE-A-21 02 469 and EP-A-84 148, such as copolymers of ethylene with vinyl acetate, vinyl propionate, vinyl butyrate, vinyl pivalate or with esters of (meth) acrylic acid, which are derived from alkanols with 1 to 12 carbon atoms.
• copolymers B show synergistic effects together with flow improvers. Although the copolymers B alone show little or no flow-improving effect, the combination of A and B far exceeds the individual efficacies.
• the monomers according to formula 1 are easily accessible. They can be obtained by the known esterification processes. For example, a solution of (meth) acrylic acid and an alkanol or a mixture of different alkanols is heated in an organic solvent with the addition of the usual polymerization inhibitors, e.g. Hydroquinone derivatives and esterification catalysts such as sulfuric acid, p-toluenesulfonic acid or acidic ion exchangers at the boil and remove the water of reaction formed by azeotropic distillation.
• the usual polymerization inhibitors e.g. Hydroquinone derivatives and esterification catalysts such as sulfuric acid, p-toluenesulfonic acid or acidic ion exchangers
• vinyl ethers can polymerize cationically under acidic conditions or decompose in the presence of water and acid to form acetaldehyde, which interferes with the radical polymerization, the neutralization of the catalyst acid and excess (meth) acrylic acid with e.g. Amines or their removal indicated by washing the ester solution with alkaline agents and water to prepare the copolymers B.
• Particularly pure esters can be obtained by distillation of the pre-cleaned ester solution.
• the vinyl ethers according to formula 11 can be obtained by known processes by reacting alkanols with acetaldehyde and subsequent elimination of water or by catalytic addition of acetylene to alkanols. Particularly pure monomers can also be obtained here by distillation. In the case of vinyl ethers with more than 20 to 22 carbon atoms in the alkyl part, the undecomposed distillation is technically difficult to carry out. In these cases, cleaning by filtration, extraction or recrystallization to remove the catalysts is recommended.
• the copolymers B are prepared by known batch or continuous polymerization processes such as bulk, suspension, precipitation or solution polymerization and initiation with customary radical donors such as acetylcyclohexane sulfonyl peroxide, diacetyl peroxidicarbonate, dicyclohexylproxidicarbonate, di-2-ethylhexyl peroxidate carbonate, tert.
• customary radical donors such as acetylcyclohexane sulfonyl peroxide, diacetyl peroxidicarbonate, dicyclohexylproxidicarbonate, di-2-ethylhexyl peroxidate carbonate, tert.
• -Azobis (4-methoxy-2,4-dimethylvaleronitrile), tert-butyl perpivalate, tert-butyl per-2-ethylhexanoate, tert-butyl permaleinate, 2,2'-azobis (isobutyronitrile), bis (tert .-Butyl peroxide) -cyclohexane, tert-butyl peroxyisopropyl carbonate, tert-butyl peracetate, dicumyl peroxide, di-tert-amyl peroxide, di-tert-butyl peroxide, p-menthane hydroperoxide, cumene hydroperoxide or tert-butyl hydroperoxide and mixtures with one another.
• these initiators are used in amounts of 0.1 to 20% by weight, preferably 0.2 to 15% by weight, based on the monomers.
• the polymerization is generally carried out at temperatures of 40 to 400 ° C., preferably 70 to 300 ° C., the use of solvents with boiling temperatures below the polymerization temperature advantageously being carried out under pressure.
• the polymerization is conveniently carried out in the absence of air, i.e. if it is not possible to work under boiling conditions, e.g. carried out under nitrogen or carbon dioxide, since oxygen delays the polymerization.
• the reaction can be accelerated by using redox coinitiators such as benzoin, dimethylaniline, ascorbic acid and organically soluble complexes of heavy metals such as copper, cobalt, manganese, iron, nickel and chromium.
• the amounts usually used are 0.1 to 2000 ppm by weight, preferably 0.1 to 1000 ppm by weight.
• regulators are, for example, allyl alcohols, such as 1-buten-3-ol, organic mercapto compounds, such as 2-mercaptoethanol, 2-mercaptopropanol, mercaptoacetic acid, mercaptopropionic acid, tert-butyl mercaptan, n-butyl mercaptan, n-octyl mercaptan, n-dodecyl mercaptan and tert.- Dodecyl mercaptan, which are generally used in amounts of 0.1 to 10 wt .-%.
• Equipment suitable for the polymerization is e.g. Conventional stirred kettles with, for example, armature, blade, impeller or multi-stage impulse countercurrent stirrers and for the continuous production of stirred kettle cascades, tubular reactors and static mixers.
• the simplest method of polymerization is bulk polymerization.
• the monomers are polymerized in the presence of an initiator and in the absence of solvents.
• all monomers are mixed in the desired composition and a small part, e.g. about 5 to 10%, in the reactor before, heated to the desired polymerization temperature with stirring and metered in the remaining monomer mixture and the initiator and optionally coinitiator and regulator evenly within 1 to 10 hours, preferably 2 to 5 hours. It is expedient to meter in the initiator and the coinitiator separately in the form of solutions in a small amount of a suitable solvent.
• the copolymer can then be added directly to the middle distillate as a solidified melt or after being taken up in a suitable solvent together with the flow improver.
• a continuous high-pressure process is also suitable for producing the desired copolymers, which permits space-time yields of 1 to 50 kg of polymer per liter of reactor and hour.
• a polymerization vessel, a pressure vessel cascade, a pressure tube or a pressure vessel with a downstream reaction tube, which is provided with a static mixer, can be used as the polymerization apparatus.
• the monomers of (meth) acrylic acid esters and vinyl ethers are preferably polymerized in at least two polymerization zones connected in series.
• One reaction zone can consist of a pressure-tight vessel, the other of a heatable static mixer. You get sales of more than 99%.
• a copolymer of (meth) acrylic acid esters and vinyl ethers can be prepared, for example, by continuously feeding the monomers and a suitable initiator to a reactor or two reaction zones connected in series, for example a reactor cascade, and the reaction product after a residence time of 2 to 60, preferably of 5 to 30 minutes, at temperatures between 200 and 400 ° C continuously from the Eject reaction zone.
• the polymerization is advantageously carried out at pressures of more than 1 bar, preferably between 1 and 200 bar.
• the copolymers obtained have solids contents of over 99% and can be added to the middle distillate without further treatment.
• copolymers B Another simple method for producing the copolymers B is solution polymerization. It is carried out in solvents in which the monomers and the copolymers formed are soluble. All solvents which fulfill this requirement and which do not react with the monomers are suitable for this. For example, these are toluene, xylene, ethylbenzene, cumene, high-boiling aromatic mixtures such as Solvesso @ 100, 150 and 200, aliphatic and cycloaliphatic hydrocarbons such as e.g.
• n-Hexane cyclohexane, methylcyclohexane, n-octane, iso-octane, paraffin oils, Shellsol @ TD, T and K as well as tetrahydrofuran and dioxane, tetrahydrofuran and dioxane being particularly suitable for achieving low molecular weight copolymers.
• solvent and part of the monomer mixture e.g. about 5 to 20%
• the monomers can also be metered in individually at different rates.
• the concentrations of the monomers to be polymerized are between 20 and 80% by weight, preferably 30 and 70% by weight.
• the solid copolymer can be easily obtained by evaporating the solvent.
• Solution polymerization is the preferred form of preparation for the copolymers of (meth) acrylates and vinyl ethers.
• polymers A and B should be present together in the form of a concentrate, since the use of 2 concentrates - one each for polymer A and polymer B - makes handling more difficult. Due to the possible incompatibility of polymers A and B, phase separation can occur when the two polymers are mixed in a common solvent. This can optionally be suppressed by suitable solvents and / or additives. Suitable are e.g.
• Alkanols such as iso-butanol, n-hexanol, 2-ethylhexanol, iso-decanol and their adducts with ethylene oxide, propylene oxide and / or butylene oxide, alkylphenols and their adducts with ethylene oxide, propylene oxide and / or butylene oxide as well as half esters or diesters of dicarboxylic acids with alkanols or (oligo ) alkylene oxide half ethers such as mono- or dibutyl phthalate, mono- or di-2-ethylhexyl phthalate or di- (2-methoxyethyl) phthalate.
• Another method of avoiding possible phase separation is to graft copolymer B at least in part onto the flow improver.
• Bulk or solution polymerization is preferably used for the grafting.
• the polymerization can be carried out according to the "batch" or feed procedure. In the "batch" procedure, the entire amount of flow improver A to be grafted is initially introduced together with the monomers and initiator and, if appropriate, coinitiator and regulator are metered in. In the feed procedure, the entire amount of flow improver A to be grafted is optionally introduced together with some of the monomers and the rest of the monomers, initiator and, if appropriate, coinitiator and regulator are metered in.
• the copolymer B As already mentioned, it is not necessary to graft the copolymer B onto the entire proportion of the flow improver A. For example, at a ratio A: B of 90:10, for reasons of space-time yield, the copolymer B will only be grafted to a proportion of 2 to 20% by weight of the total amount of A. With a ratio of A: B of 40:60, however, to a proportion of 30 to 100% by weight of the total amount of A.
• copolymer B may also be present in the concentrates described.
• the K values (according to H. Fikentscher, Cellulosechemie, Volume 13, pages 58 to 64 and 71 to 74 (1932)), determined in 2% (w / v) xylene solution of the copolymers B are between 10 and 50, preferably between 10 and 40 and particularly preferably between 13 and 30.
• the particularly preferred range corresponds to molecular weights between approx. 5000 and 25,000 g / mol (number average, determined by gel permeation chromatography against polystyrene standards).
• the additives A and B according to the invention are added to the petroleum middle distillates together in amounts of 50 to 5000 ppm, preferably 100 to 2000 ppm.
• the middle distillates according to the invention containing small amounts of a flow improver A and a copolymer B, can, depending on the intended use, other additives or additives such as dispersants, anti-foam additives, corrosion inhibitors, antioxidants, dyes and others. contain.
• Examples 4 to 18 were prepared by a procedure analogous to that in Example 3.
• Example 20 (comparison test analogous to DE-A-16 45 785)
• Examples 17 to 20 are comparative examples and do not form part of the present invention.
• the flow improvers FI (A), FI (B) and Fl (C) are commercially available products, e.g. the Keroflux® brands from BASF.
• Middle distillate I, II, III and IV Heating oils and diesel fuels in commercial West German refinery quality were used as middle distillates. They are referred to as middle distillate I, II, III and IV.

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
• Fats And Perfumes (AREA)
• Detergent Compositions (AREA)
• Treating Waste Gases (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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Cited By (11)

Citations (7)

• 1990
  • 1990-11-14 DE DE4036227A patent/DE4036227A1/de not_active Withdrawn
• 1991
  • 1991-10-24 EP EP91118118A patent/EP0486836B1/fr not_active Expired - Lifetime
  • 1991-10-24 AT AT91118118T patent/ATE118529T1/de not_active IP Right Cessation
  • 1991-10-24 DE DE59104601T patent/DE59104601D1/de not_active Expired - Lifetime
  • 1991-10-24 ES ES91118118T patent/ES2068464T3/es not_active Expired - Lifetime
  • 1991-10-30 FI FI915126A patent/FI105824B/fi active
  • 1991-11-13 CA CA002055418A patent/CA2055418A1/fr not_active Abandoned
  • 1991-11-13 NO NO914443A patent/NO304077B1/no not_active IP Right Cessation

Patent Citations (7)

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