EP0007590A1 - Distillats moyens de pétrole, appropriés comme huile de diesel et huile de chauffe légère, ayant une filtrabilité améliorée - Google Patents

Distillats moyens de pétrole, appropriés comme huile de diesel et huile de chauffe légère, ayant une filtrabilité améliorée Download PDF

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Publication number
EP0007590A1
EP0007590A1 EP79102558A EP79102558A EP0007590A1 EP 0007590 A1 EP0007590 A1 EP 0007590A1 EP 79102558 A EP79102558 A EP 79102558A EP 79102558 A EP79102558 A EP 79102558A EP 0007590 A1 EP0007590 A1 EP 0007590A1
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EP
European Patent Office
Prior art keywords
copolymers
ethylene
middle distillates
monomeric
esters
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EP79102558A
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German (de)
English (en)
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EP0007590B1 (fr
Inventor
Hans-Henning Dr. Chem. Vogel
Manfred Schramm
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BASF SE
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BASF SE
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Filing date
Publication date
Priority claimed from DE19782832738 external-priority patent/DE2832738A1/de
Priority claimed from DE19792908564 external-priority patent/DE2908564A1/de
Application filed by BASF SE filed Critical BASF SE
Priority to AT79102558T priority Critical patent/ATE17T1/de
Publication of EP0007590A1 publication Critical patent/EP0007590A1/fr
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Publication of EP0007590B1 publication Critical patent/EP0007590B1/fr
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G 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
    • 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
    • C10L1/188—Carboxylic acids; metal salts 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
    • C10L1/196—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
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B3/00—Engines characterised by air compression and subsequent fuel addition
    • F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition

Definitions

  • the invention relates to middle distillates of petroleum which are suitable as diesel fuels or light heating oil with improved filterability at temperatures above and below the cloud point and improved flow behavior.
  • monomers are added as solubilizers.
  • middle distillates such as gas oils, diesel oils or egg oils, such as those obtained from petroleum by distillation
  • paraffin wax is excreted in the form of platelet-shaped crystals, some of which also contain oil.
  • the fluidity of the petroleum distillate - fuels is significantly impaired.
  • this leads to the clogging of filters and thus to the interruption or non-uniform supply of the fuel to the combustion units such as engines or jet engines.
  • Malfunctions in heating oils can also occur in winter if such precipitations, due to low temperatures, occur.
  • the pumping of middle distillates through pipelines over long distances can also be affected in winter by the precipitation of wax crystals.
  • Such additives change the size and shape of the wax crystals so that the oil remains fluid even at low temperatures.
  • Such additives are known as "pour point improvers" or “flow improvers” or “pour point improvers”.
  • condensation products from chlorinated paraffins and naphthalene used. In order to be sufficiently successful, however, such condensation products must be used in relatively large amounts.
  • efforts have recently been made to switch off chlorinated hydrocarbons for this purpose as far as possible in order to avoid corrosive gases which are produced during combustion.
  • the polymers previously proposed as pour point and flow improvers now have the described properties in practical use at low temperatures, i.e. temperatures below the cloud point, as modifiers or growth inhibitors for paraffin crystals, but in many cases they show up to about above the cloud point plus 30 ° C considerable disadvantage le.
  • diesel engines used in practice are equipped with filter materials of different pore sizes depending on the application. An unimpeded fuel supply must be guaranteed at all times, even under extreme conditions.
  • diesel engines have very narrow-pore fuel filters with pore sizes of 2 to 40 ⁇ . Multi-layer filters made of materials with very different pore sizes for coarse and fine filtration are also frequently used.
  • the invention consists in middle distillates of petroleum, which are suitable as diesel fuels or light heating oil, with improved fileability and improved flow behavior with a content of small amounts of modifiers in the form of copolymers, selected from the group of binary copolymers of ethylene and a vinyl ester of a C 2 - or C 3 -alkane carboxylic acid and binary copolymers of a C 1 to C 8 alkyl ester of a C 3 or C 4 alkene monocarboxylic acid, the copolymers copolymerizing 60 to 95% by weight of ethylene and 5 to 40% by weight of the olefinically unsaturated ester contain and have a viscosity in the melt, measured according to DIN 51 562 (ASTM D 445) at 120 ° C from 100 to 5000 mm 2 / sec, which are characterized in that the middle distillates in addition to the copolymers 0.1 to 10 vol .%, based on the copolymer, the monomeric vinyl esters of a C
  • the monomers are preferably present in amounts of 0.5 to 5% by volume, based on the copolymer.
  • binary copolymers which are obtained by polymerizing ethylene and vinyl acetate or alkyl acrylates without solvents at pressures from 500 to 2,000 bar and temperatures from 100 to 350 ° C., preferably 200 to 300 ° C., and the molecular weights from 500 to 10,000, preferably 1,000 to 5,000.
  • the radical copolymerization can be started simply with air, but also by means of suitable proxidic initiators or by adding L suitable controllers (e.g. aliphatic aldehydes) can be controlled.
  • the unreacted ethylene and the vinyl acetate and low-boiling oligomers are preferably separated off by decompression of the reactor and the solvent-imparting monomers are subsequently added to the ethylene-free copolymer.
  • the monomers are preferably subsequently added to the copolymer.
  • the monomers contained in the copolymers are, in particular, vinyl esters of carboxylic acids with 1 to 4 carbon atoms, preferably vinyl acetate with vinyl propionate, and acrylic and methacrylic esters of C 1 to C 8 alkanols, in particular butyl, isobutyl, 2-ethylhexyl and Lauryl acrylate into consideration.
  • esters of maleic acid are dimethyl maleate or dibutyl maleate.
  • the monomers serving as solubilizers are generally added, alone or in combination with one another, to the copolymers prepared by the known processes, which are generally of very tough consistency and, for example, have viscosities in the range from 100 to 5000 mm 2 / s at 120 ° C.
  • the copolymers are usually dispersed in suitable solvents which have little or no solubility-improving effect. They are used e.g. higher-boiling, highly aromatic products, e.g. contain multiple alkylated benzenes, toluenes, xylenes, ethylbenzenes and optionally also higher alkylated naphthalenes. Another frequently used method is the dispersion of the copolymeric waxes in suitable petroleum distillates. Heavy gasoline, petroleum, diesel oil or gas oil fractions are used here in particular.
  • the monomers serving as solubility improvers can therefore be added to the copolymer waxes themselves, but also to the dispersions of these waxes in suitable dispersants; elevated temperatures e.g. 30 to 90 ° C and thorough mixing by stirring or pumping are advisable.
  • polymerization-sensitive unsaturated esters such as vinyl acetate or acrylic acid esters or unsaturated oligomers
  • polymerization inhibitors are e.g. polyalkylated phenols, nitrogen-containing aromatic heterocycles or alkylated aromatic aminophenols or substituted or unsubstituted phenylenediamines.
  • the minimal discoloration of the petroleum distillates caused by the inhibitors is insignificant.
  • the polymeric waxes settle in the dispersions.
  • the dispersions with a low proportion (eg 1 to 50% by weight) of copolymeric ethylene / vinyl fatty acid ester ⁇ or. Ethylene / acrylic acid esters, the dispersions obtained are not as stable as with higher proportions (for example over 50% by weight) of copolymer wax. It has now additionally been found that the additions of monomers to copolymeric waxes described above also have a thickening effect for the dispersions of the copolymeric waxes in the stated concentrations.
  • the stability of the dispersions is also increased considerably in many cases.
  • the copolymeric waxes do not settle or only to a very small extent.
  • a certain amount of the petroleum distillate to be examined (e.g. kerosene, gas oil, diesel fuel, heating oil EL according to DIN 51 601) is filtered in a water jet vacuum in portions of 100 ml each through a membrane filter. The flow times are measured per 100 ml.
  • Sartorius membrane filter attachment type SM 16307 Sartorius membrane filter type SM 11301 pore size 8 / u, n-Pentar
  • the selected petroleum distillate is filtered through a paper pleated filter to remove coarse suspended matter and dirt.
  • the sample which has been pre-cleaned in this way, is filtered in a water jet vacuum through a bluing belt filter.
  • a certain amount of flow improver dispersion or cow axis is mixed into 3,000 ml of the petroleum distillate pretreated in this way at room temperature.
  • the petroleum distillate modified in this way is filtered through a membrane filter in portions of 100 ml.
  • the throughput time for 100 ml of liquid is measured and graphically plotted against the filtered volume.
  • the time axis is divided logarithmically.
  • Method B Quantitative determination of the high molecular weight proportions of copolymer wax which are insoluble in petroleum distillate.
  • the membrane filter Before filtration, the membrane filter is washed with 100 ml of n-pentane, dried and weighed. After filtration of the petroleum distillate to be examined, the membrane filter is washed again oil-free with 100 ml and n-pentane, dried and weighed out. The amount of higher molecular weight residue which is insoluble in petroleum distillate is given in% by weight based on copolymer wax.
  • method A ensures that the filtration curves of petroleum distillate fuels and fuels, which do not contain copolymeric waxes, do not show an increase in the filtration time as the volume of the filtration increases.
  • the filtration time per 100 ml of filtered product depends only on the viscosity or density of the petroleum distillate. According to method A, petroleum distillates not modified with copolymer waxes do not indicate filter clogging.
  • the above filtration test can be varied by filtering smaller volumes (e.g. portions of 20 ml each). In this way it is possible to distinguish more clearly between very similar cow axes, which all result in a very bad filtration curve according to method A.
  • the membrane filter In the case of copolymer waxes with extremely low proportions of higher molecular weight compounds, the membrane filter only clogs at higher throughputs of modified petroleum distillate. (e.g. 10 to 1001.) In this case, larger sample volumes of 500 or 1,000 ml are recommended for the filtration test.
  • the temperature is essential for the filtering behavior of petroleum distillates modified with flow improvers. It could be shown that the solubility of the small amounts of higher molecular weight compounds contained in the copolymer waxes is a function of the temperature.
  • the solubilizing effect of the monomers extends to temperatures from well above the natural cloud point of the petroleum distillates (eg 30 ° C) to far below the cloud point (eg -40 ° C). At or below the cloud point in petroleum distillates, the precipitation of paraffin crystals begins with a further decrease in temperature.
  • ethylene / fatty acid vinyl esters or ethylene / acrylic acid esters as flow improvers, these paraffin crystals are modified and their growth is disturbed, the oil is cloudy due to excreted paraffins, but remains flowable and pumpable.
  • Table 1 shows the physical data of various copolymer waxes based on ethylene / vinyl acetate. The table also shows the proportions of monomeric vinyl acetate still present in the copolymer washes.
  • the cowaxes listed in Table 1 were adjusted as 50% dispersions in various dispersing agents and the filtering behavior of various gas oils after addition of 500 ppm by volume of the dispersions which act as flow improvers was investigated using Method A.
  • the higher molecular weight components present in the 50% dispersions and determined by Method 3 are summarized in Table 2.
  • 1 and 2 show the filtration curves of the cow axis from Table 2 determined according to Method A. A, where here and in the following t means the filtration time in seconds and v the filtration volume in ml.
  • Table 2 and FIGS. 1 and 2 show, all of the cow axes investigated in the dispersants used have poor filterability (according to method A) and correspondingly large proportions of higher molecular weight products according to method B.
  • the following examples show the mode of action of the solubilizers claimed.
  • the Cowachs No. 1 already mentioned in Table 1 and FIG. 1 was mixed with the solubilizers according to the invention as a 50% dispersion in C 4 -oxoalkahol residue as a dispersing agent.
  • the dispersions thus improved were added to a diesel fuel in an amount of 500 ppm by volume and investigated according to methods A and 3.
  • Cowachs No. 3 mentioned in Table 1 was adjusted as a 50% dispersion in C 4 oxo alcohol residue. As Table 2 shows, an amount of 5.6% higher molecular weight components was found in the method B filtration test. Curve 5 in Fig. 1 and A in Fig. 4 shows correspondingly poor filtering behavior (according to method A). When 1% by weight of vinyl acetate is added to the 50% dispersion of Cowachs No. 3 in the C 4 -oxoalcohol residue, after adding 500 vol Method B found only 0.34% higher molecular weight. Curve B in Fig. 4 shows the filtration curves according to method A.
  • the filtration test according to method A was carried out extra easily (according to DIN 51 601) after adding 500 ppm by volume of the 50% dispersion of the copolymer wax in C 4 oxo alcohol residue to a commercially available heating oil. Filtration curve No. 1 shown in FIG. 5 was obtained.
  • a filtration test according to methods A and B with the addition of 800 vol.ppm of the 40% dispersion to a commercially available heating oil is carried out extra easily (in accordance with DIN 51 601).
  • the filter test is carried out immediately, as well as after 8 days and 30 days of the additive heating oil.
  • the associated filtration curves 1, 2 and 3 in FIG. 6 and, according to Method B a proportion of higher molecular weight compounds of 9.5 (curve 1), 9, 7 (curve 2) and 10.1% by weight (based on cowachs) are obtained. .
  • Further filtration tests according to methods A and B are carried out after an amount of 0.5% by weight of monomeric vinyl acetate had previously been added to the dispersion. From this improved flow improver dispersion, 800 vol.ppm were also added to the same heating oil.
  • the filter test of the additive heating oil is also carried out here immediately or after 8 days and 30 days.
  • a copolyner wax prepared by continuous polymerization without solvent at a temperature of 245 ° C and a pressure of 1,500 bar from ethylene and 2-ethylhexyl acrylate with a content of 46.2% by weight 2-ethylhexyl acrylate, a viscosity at (120 ° C) of 252 mm 2 / s and an average molecular weight of 2,440 was adjusted as a 58% dispersion in petroleum, heated to 80 ° C. with stirring for one hour, cooled to room temperature and subjected to a filtration test according to methods A and B.
  • a commercial heating oil (extra light) was mixed with 500 ppm of the 58% dispersion.
  • the filtration test was repeated after 24, 48, 108 and 240 hours at room temperature.
  • the amount of polymeric residues and the associated filtration curves are shown in Tables 4 and 7.
  • t means filtration time in seconds
  • v filtration volume in ml curves 1, 2, 3, 4 according to, (a) after 24, 48, 108 and 240 hours, curves 5, 6, 7, 8 according to (b) after 24, 48 , 108 and 240 hours.
  • the copolymer wax No. 1 described in Table 1 is adjusted as a 50% dispersion in an oxo alcohol residue from the butanol synthesis.
  • the dispersion is heated to 80 ° C. with stirring, allowed to cool to room temperature and after a standing time of 36 days at room temperature for the filter test A and 3 used.
  • a commercial heating oil (extra light) from the cloud point -2 ° C is mixed with 500 ppm by weight of the dispersion and cooled to 0 ° C in the course of 35 minutes.
  • diesel oil is pumped through a commercially available fuel filter.
  • the apparatus consists of an insulated storage vessel (B 1) with a volume of 110 1 for the diesel oil, in which there is a cooling coil operated with cooling brine (s), a Bosch fuel pump (P-1) for 0-1.5 bar , a Kraftstaffiltar (F), Bosch no. 1457434052, with differential pressure gauge (PI-2) and a continuous fuel flow meter (FI).
  • the PI-1 and PI-3 pressure measuring points and the TI-1, TI-2 and TI-3 temperature displays are also installed.
  • the quantity of diesel oil pumped through the filter F is collected in the receptacle B-2 (volume 110 1).
  • the pump and filter are located in a cool box operated with dry ice in order to avoid temperature increases due to heat conduction and pump work.
  • the criterion for covering the fuel filter with high molecular weight components from the copolymeric flow improver is the pressure increase of the differential pressure sonoceter PI-2.
  • Curve 1 Cowaehs from ethylene-vinyl acetate with 28.1% by weight vinyl acetate, average molecular weight 2,160, melt viscosity (120 ° C.) 230 mm 2 / s, content of monomeric vinyl acetate 0.07% by weight, as 50% Dispersion in oxo oil residue from butanol synthesis. Dosage of the dispersion in diesel oil: 500 vol ppm - without further addition of solubilizers - temperature: + 0 ° C.
  • Curve 2 same as 1, but after adding 0.5% by weight of monomeric vinyl acetate (stabilized), based on cowachs.
  • Curve 3 as 2, but with 1.0% by weight of monomeric vinyl acetate.
  • Curve 4 as 2, but with 3.0% by weight of mononer vinyl acetate.
  • the Cowachs No. 1 mentioned in Table 1 and FIG. 1 was added as a 50% dispersion in C 4 -oxoalcohol residue as a dispersant with the solubilizers according to the invention.
  • the dispersions thus improved were added to a diesel fuel in an amount of 500 ppm by volume and investigated according to methods A and B.
  • the following table shows the effect of the solubilizers on the amount of the higher molecular residue contained in Cowachs No. 1.
  • the residues were determined according to method B. 11 shows the filtration curves belonging to table 5.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Lubrication Details And Ventilation Of Internal Combustion Engines (AREA)
EP79102558A 1978-07-26 1979-07-20 Distillats moyens de pétrole, appropriés comme huile de diesel et huile de chauffe légère, ayant une filtrabilité améliorée Expired EP0007590B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT79102558T ATE17T1 (de) 1978-07-26 1979-07-20 Mitteldestillate des erdoels, die als dieseltreibstoffe oder leichtes heizoel geeignet sind, mit verbesserter filtrierbarkeit

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19782832738 DE2832738A1 (de) 1978-07-26 1978-07-26 Mitteldestillate des erdoels, die als dieseltreibstoffe oder leichtes heizoel geeignet sind, mit verbesserter filtrierbarkeit
DE2832738 1978-07-26
DE19792908564 DE2908564A1 (de) 1979-03-05 1979-03-05 Mitteldestillate des erdoels, die als dieseltreibstoffe oder leichtes heizoel geeignet sind, mit verbesserter filtrierbarkeit
DE2908564 1979-03-05

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EP0007590A1 true EP0007590A1 (fr) 1980-02-06
EP0007590B1 EP0007590B1 (fr) 1981-02-18

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EP (1) EP0007590B1 (fr)
DE (1) DE2960183D1 (fr)
NO (1) NO145725C (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4311660C1 (de) * 1993-04-08 1994-01-13 Leuna Werke Ag Kraftstoffzusammensetzung mit verbessertem Fließverhalten bei tiefen Temperaturen
US5814110A (en) * 1986-09-24 1998-09-29 Exxon Chemical Patents Inc. Chemical compositions and use as fuel additives
WO1999029748A1 (fr) * 1997-12-05 1999-06-17 Basf Aktiengesellschaft Procede pour produire des copolymeres d'ethylene dans des reacteurs tubulaires segmentes et utilisation de ces copolymeres comme ameliorateurs d'ecoulement
US6495495B1 (en) 1999-08-20 2002-12-17 The Lubrizol Corporation Filterability improver
EP0900836B2 (fr) † 1997-09-08 2008-06-11 Clariant Produkte (Deutschland) GmbH Additif pour améliorer l'écoulement d'huiles minérales et de distillats d'huile minérale
WO2011001352A1 (fr) 2009-07-03 2011-01-06 Total Raffinage Marketing Terpolymere ethylene/acetate de vinyle/esters insatures comme additif ameliorant la tenue a froid des hydrocarbures liquides comme les distillats moyens et les carburants ou combustibles
WO2011134923A1 (fr) 2010-04-27 2011-11-03 Basf Se Terpolymère quaternisé
WO2011138400A1 (fr) 2010-05-07 2011-11-10 Basf Se Terpolymère et son utilisation pour améliorer les propriétés d'écoulement à froid de carburants de distillat moyen
US8642521B2 (en) 2003-12-04 2014-02-04 Basf Se Fuel oil compositions with improved cold flow properties
US8790426B2 (en) 2010-04-27 2014-07-29 Basf Se Quaternized terpolymer
US9102767B2 (en) 2009-03-25 2015-08-11 Total Raffinage Marketing Low molecular weight (meth)acrylic polymers, free of sulphur-containing, metallic and halogenated compounds and with low residual monomer content, method for preparing the same and uses thereof
WO2016075070A1 (fr) 2014-11-10 2016-05-19 Basf Se Copolymères d'éthylène-propylheptyl(méth)acrylate
WO2021250115A1 (fr) 2020-06-10 2021-12-16 Total Marketing Services Fluide hydrocarboné doté de propriétés améliorées aux températures froides

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3627838A (en) * 1964-12-11 1971-12-14 Exxon Research Engineering Co Process for manufacturing potent pour depressants
US3792983A (en) * 1968-04-01 1974-02-19 Exxon Research Engineering Co Ethylene and acrylate esters, their preparation and their use as wax crystal modifiers
DE2515805A1 (de) * 1974-04-17 1975-10-30 Exxon Research Engineering Co Aethylencopolymere, verfahren zu deren herstellung und dieselben enthaltende destillatoele
FR2344625A1 (fr) * 1976-03-17 1977-10-14 Shell Int Research Compositions combustibles a base de distillats moyens

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3627838A (en) * 1964-12-11 1971-12-14 Exxon Research Engineering Co Process for manufacturing potent pour depressants
US3792983A (en) * 1968-04-01 1974-02-19 Exxon Research Engineering Co Ethylene and acrylate esters, their preparation and their use as wax crystal modifiers
DE2515805A1 (de) * 1974-04-17 1975-10-30 Exxon Research Engineering Co Aethylencopolymere, verfahren zu deren herstellung und dieselben enthaltende destillatoele
FR2344625A1 (fr) * 1976-03-17 1977-10-14 Shell Int Research Compositions combustibles a base de distillats moyens

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5814110A (en) * 1986-09-24 1998-09-29 Exxon Chemical Patents Inc. Chemical compositions and use as fuel additives
DE4311660C1 (de) * 1993-04-08 1994-01-13 Leuna Werke Ag Kraftstoffzusammensetzung mit verbessertem Fließverhalten bei tiefen Temperaturen
EP0620265A1 (fr) * 1993-04-08 1994-10-19 Leuna-Werke Gmbh Composition de combustible à comportement amélioré à l'écoulement aux basses températures
EP0900836B2 (fr) † 1997-09-08 2008-06-11 Clariant Produkte (Deutschland) GmbH Additif pour améliorer l'écoulement d'huiles minérales et de distillats d'huile minérale
WO1999029748A1 (fr) * 1997-12-05 1999-06-17 Basf Aktiengesellschaft Procede pour produire des copolymeres d'ethylene dans des reacteurs tubulaires segmentes et utilisation de ces copolymeres comme ameliorateurs d'ecoulement
DE19754039A1 (de) * 1997-12-05 1999-06-24 Basf Ag Verfahren zur Herstellung von Ethylencopolymeren in segmentierten Rohrreaktoren und Verwendung der Copolymere als Fließverbesserer
US6495495B1 (en) 1999-08-20 2002-12-17 The Lubrizol Corporation Filterability improver
US10526558B2 (en) 2003-12-04 2020-01-07 Basf Se Fuel oil compositions with improved cold flow properties
US10047314B2 (en) 2003-12-04 2018-08-14 Basf Se Fuel oil compositions with improved cold flow properties
US9605227B2 (en) 2003-12-04 2017-03-28 Basf Se Fuel oil compositions with improved cold flow properties
US8642521B2 (en) 2003-12-04 2014-02-04 Basf Se Fuel oil compositions with improved cold flow properties
US9102767B2 (en) 2009-03-25 2015-08-11 Total Raffinage Marketing Low molecular weight (meth)acrylic polymers, free of sulphur-containing, metallic and halogenated compounds and with low residual monomer content, method for preparing the same and uses thereof
WO2011001352A1 (fr) 2009-07-03 2011-01-06 Total Raffinage Marketing Terpolymere ethylene/acetate de vinyle/esters insatures comme additif ameliorant la tenue a froid des hydrocarbures liquides comme les distillats moyens et les carburants ou combustibles
US8790426B2 (en) 2010-04-27 2014-07-29 Basf Se Quaternized terpolymer
WO2011134923A1 (fr) 2010-04-27 2011-11-03 Basf Se Terpolymère quaternisé
WO2011138400A1 (fr) 2010-05-07 2011-11-10 Basf Se Terpolymère et son utilisation pour améliorer les propriétés d'écoulement à froid de carburants de distillat moyen
WO2016075070A1 (fr) 2014-11-10 2016-05-19 Basf Se Copolymères d'éthylène-propylheptyl(méth)acrylate
WO2021250115A1 (fr) 2020-06-10 2021-12-16 Total Marketing Services Fluide hydrocarboné doté de propriétés améliorées aux températures froides
US12091631B2 (en) 2020-06-10 2024-09-17 Totalenergies Onetech Hydrocarbon fluid having improved cold temperature properties

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DE2960183D1 (en) 1981-04-02
EP0007590B1 (fr) 1981-02-18
NO145725B (no) 1982-02-08
NO145725C (no) 1982-05-19
NO792453L (no) 1980-01-29

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