EP0301837A1 - Verfahren zur Herstellung einer fliessverbesserten Brennölzusammensetzung - Google Patents

Verfahren zur Herstellung einer fliessverbesserten Brennölzusammensetzung Download PDF

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Publication number
EP0301837A1
EP0301837A1 EP88306929A EP88306929A EP0301837A1 EP 0301837 A1 EP0301837 A1 EP 0301837A1 EP 88306929 A EP88306929 A EP 88306929A EP 88306929 A EP88306929 A EP 88306929A EP 0301837 A1 EP0301837 A1 EP 0301837A1
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EP
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Prior art keywords
amount
fuel oil
smaller
paraffin
ethylene
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Application number
EP88306929A
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English (en)
French (fr)
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EP0301837B1 (de
Inventor
Tadayuki Ohmae
Sumio Hara
Kentaro Mashita
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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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
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • 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
    • C10L1/16—Hydrocarbons
    • C10L1/1691—Hydrocarbons petroleum waxes, mineral waxes; paraffines; alkylation products; Friedel-Crafts condensation products; petroleum resins; modified waxes (oxidised)
    • 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

Definitions

  • This invention relates to a fuel oil composition having a low flowability at low temperatures prepared from a heavy distillate fuel of petroleum and a low temperature flow improver.
  • kerosene and heavy oil A suffer remarkable decrease in flowability at low temperatures (or cold flowability) in winter season and the like due to separation of wax component contained in the oil, which tends to cause severe problems.
  • the wax component contained in kerosene separates out and causes clogging or plugging of minute screen which is incorporated in a filter for preventing impurities provided in midway in a pipeline from a kerosene tank to an engine in a diesel automobile, so that supply of kerosene becomes impossible and as the result the engine stops.
  • Another conventional method for improving the cold flowability of fuel oils is to add a cold flow improver to the fuel oils.
  • the action of the cold flow improver is to give influence upon separation-out of wax from fuel oils to prevent the growth of wax into large-size cyrstals but retain the wax in the form of minute crystals, thus stabilizing the cold flowability.
  • This method not only requires addition of both the ethylene copolymer and n-paraffin, which causes complication of installments and operation, but also involves increase in the amont of wax separated out at low temperatures because of paraffin, which is a principal causal substance for aggravation of cold flowability due to separating-out of wax, is positively added. As the result, it is often the case that the cold flow improver does not act effectively.
  • an object of this invention is to obviate the above-described defects of the prior arts and provide a fuel oil mainly composed of medium and/or heavy distillates of crude oil and having an improved cold flowability.
  • Another object of this invention is to optimize the amount of n-paraffin contained in the middle and/or heavy distillates of crude oil in order to have sufficiently exhibited the effect of a cold flow improver.
  • this invention provides a fuel composition
  • a fuel composition comprising a base fuel oil composed mainly of middle and/or heavy distillates of crude oil and containing n-paraffin having at least 25 carbon atoms in an amount of not smaller than 0.1 wt.% and smaller than 0.6 wt.% and wax which separates out at a temperature by 10°C lower than the cloud point in an amount of smaller than 4 wt.%, and a cold flow improver composed of a copolymer of ethylene and a vinyl ester of an unsaturated carboxylic acid, the copolymer having an ethylene content of 60 to 80 wt.% and a number average molecular weight of 1,000 to 5,000, in an amount of 30 to 1,500 ppm.
  • base fuel oil composed mainly of middle and/or heavy distillates of crude oil refers to distillate oils obtained by distilling crude oil which is a mixture of a great number of components composed mainly of hydrocarbons having a boiling point of from about 150°C. to about 450 °C.
  • distillate fractions obtained from general petroleum distilling installments include light gas oil, heavy gas oil, or heavy gas oil hydrogenated using a purifier such as a unifiner, or vacuum gas oil which is obtained by vacuum distilling the distillation residue from normal pressure distillator in a vacuum distillator and its hydrogenated product. They can be used as a blend depending on their application.
  • the base fuel oil can be mixed with a small amount of middle or heavy distillate oil generated in petroleum purifiers, e.g., oils treated in catalytic cracking apparatus, hydrogenolysis apparatus, etc. or residual oils after dewaxing during manufacture of lubricants.
  • middle or heavy distillate oil generated in petroleum purifiers, e.g., oils treated in catalytic cracking apparatus, hydrogenolysis apparatus, etc. or residual oils after dewaxing during manufacture of lubricants.
  • the amount of n-paraffin having at least 25 carbon atoms contained in the middle and/or heavy distillate oils of petroleum as base fuel oil can be analyzed in a usual manner using a programmed-temperature gas chromatography apparatus.
  • a trace amount sample is analyzed using a hydrogen flame ionizing detector with a column packed with a filler composed of a partition agent having a weak polarity and a porous carrier, and the content of n-paraffin is obtained from the respective chromatograms of the separated components.
  • a sample oil is injected into a column of a stain-less steal tube having a diameter of 3 mm and a length of 4,000 mm packed with a column filler (Silicon GE SE-30, 2%, 60/80 mesh, Uniport HP carrier) commercially available from Wako Pure Chemicals Industries, Ltd. and the temperature of the column is elevated starting from 70°C to 270 °C at a rate of 5 °C/min., and detection is performed by hydrogen flame ionizing method.
  • the electric signals detected are processed with a recorder or data processor as output to outside.
  • the content of n-paraffin can be obtained by calculating n-paraffin peak.
  • the content of n-paraffin having at least 25 carbon atoms contained in the middle and/or heavy distillate oils of petroleum as base fuel oil is preferably not smaller than 0.1 wt.% and smaller than 0.6 wt%.
  • n-paraffin having at least 25 carbon atoms When the content of n-paraffin having at least 25 carbon atoms is smaller than 0.1 wt%, the effect of improvement in cold filter plugging point with a cold flow improver becomes poor. On the other hand, when it is larger than 0.6 wt%, although sometimes addition of a very large amount, e.g., 2,000 ppm or more, of a cold flow improver permits improvement in cold filter plugging point, total amount of wax which separates out increases, resulting in that the fuel oil obtained tends to be one which cannot be used practically.
  • Preferred amount of n-paraffin having at least 25 carbon atoms with which the effect of cold flow improver added can be exhibited more efficiently is not smaller than 0.2 wt.% and smaller than 0.5 wt.%. In this range, addition of a relatively low amount of cold flow improver enables sufficient decrease in the cold filter plugging point.
  • cold flow improver used in this invention examples include those described in "Shinpan Sekiyu Seihin Tenkazai” ed. by Toshio Sakurai, Saiwai Shobo, July 1986, pp.192-195. More particularly, ethylene copolymers disclosed in Japanese Patent Publication Nos. Sho-48-23165, Sho-55-33480, and Sho-60-17399, Published Unexamined Japanese Patent Application No. Sho-59-136391.
  • ethylene copolymer examples include those copolymers which contain one or more vinyl esters of saturated fatty acids such as vinyl acetate, vinyl propionate, vinyl butyrate, etc. as a comonomer. They may be a low molecular weight product obtained by decomposing a high molecular weight ethylene copolymer with oxygen, peroxides, heat, etc.
  • Preferred ethylene coplymer inlcudes those copolymers which have an ethylene content of 60 to 80 wt.%, and a number average molecular weight in the range of from 1,000 to 5,000 measured by vapor ressure equilibrium method.
  • the ethylene copolymer may be used singly or as a mixture of two or more of it. Although the ethylene copolymer can be mixed with and dissolved in fuel oils as it is, it is industrially preferred to dissolve it in a hydrocarbon based solvent and use it as a 10 to 90 wt.% solution.
  • ethylene-vinyl acetate coplymers are particularly preferred because they are not only readily available on industrial scale but also are excellent in the effect of improving cold flowability.
  • More preferred ethylene-vinyl acetate copolymer is those copolymers having an ethylene content of 60 to 75 wt.%, and a number average molecular weight of 1,000 to 4,000, with molecular weight distribution being not lower than 4.0, and containing not more than 6 methyl terminated side chains per 100 main-chain methylene groups as well as methyl groups contained in the acetyl group.
  • the copolymers exhibit further decrease in cold filter plugging point.
  • the molecular weight distribution is obtained from the ratio of weight average molecular weight (Mw)/number average molecular weight (Mn) calculated as standard polystyrene according to gel permeation chromatography (GPC) (cf. "Kobunshi Sokuteihou, Kouzou to Bussei” vol. 1, ed. by Kobunshi Gakkai, Baihukan, 1973, pp.76-89).
  • GPC gel permeation chromatography
  • the degree of branching as used herein is expressed as the number of methyl terminated side chains per 100 main-chain methylene groups besides methyl groups in the acetoxy groups, and calculated from the results obtained by nuclear magnetic resonance (1H NMR) method (cf. the method described in "Nippon Kagaku Kai Shi", No. 1, 1980, pp.74-­78).
  • peak ratio based on methyl group and methylene group in proton nuclear magnetic resonance spectrum is obtained.
  • the vinyl acetate content is obtained by saponification method and the number average molecular weight is obtained by vapor pressure osmotic pressure method.
  • the degree of branching is calculated from the peak ratio, the vinyl acetate content and the number average molecular weight. It is to be noted that assumption is made that both the ends of the main-chain methylene groups are methyl groups and that all the side chains are ethyl groups, and therefore, 2 terminal methyl groups are deduced upon calculation.
  • the amount of the cold flowability improver used in this invention is in the range of preferably 30 to 1,500 ppm, more preferably 50 to 1,000 ppm based on the weight of the base fuel oil composed of the middle and/or heavy distillates of petroleum.
  • the fuel oil composition of this invention may contain one or more of rust preventives, antioxidants, antistatics, cetane value improvers and anticorrosives.
  • n-Paraffin content 50 ml of cold ethanol was added to the residual wax component and the mixture was all intorduced into 11G4 glass filter to remove oily component under vacuum. After the wax component which remained on the glass filter was air-dried for one day and one night, the weight of wax component was measured to obtain the amount of wax separated out.
  • n-paraffin in the test oil was obtained using GAS CHROMATOGRAPH GC-9A type and CHROMATOPACK C-R2AX data processor, manufactured by Shimazu Seisakusho Co., Ltd.
  • n-Triacontane was used as an inner standard substance for quantitative determination.
  • Principal operational conditions are as follows. Column: Made of stainless steal, 3 mm in inner diameter and 4m in length
  • Injection Temperature 270 °C
  • Carrier Gas Helium Detector: Hydrogen flame ionizing detector
  • Diesel gas oil samples Nos. 5 and 9 shown in Tables 4 and 5 were mixed with each other at a mixing ratio of 75/25 (Sample No. 6), 50/50 (Sample No. 7), or 25/75 (Sample No. 8), each by volume.
  • the characteristics of mixed test oils are also shown in Tables 4 and 5.
  • Additive A composed of a 60 wt.% xylene solution of an ethylene-vinyl acetate copolymer having a viny acetate content of 36.5 wt.%, a number average molecular weight of l,690, and a number of methyl terminated side chains of 3.8 groups/100 methylene groups, and CFPP of each mixture was measure.
  • Additive B is a 60 wt.% xylene solution of an ethylene-vinyl acetate copolymer having a vinyl acetate content of 16.5 wt.%, a number average molecular weight of 2,200.
  • Additive C is a 60 wt.% xylene solution of an ethylene-vinyl acetate copolymer having a vinyl acetate content of 44.6 wt.% and a number average molecular weight of 1,820.
  • Table 7 Sample No.
  • sample oils which contained n-paraffin having at least 25 carbon atoms in an amount of below 0.1 wt.% or not smaller than 0.6 wt.% and wax component which separated out at a temperature 10°C- below the cloud point in an amount of not smaller than 4 wt.% did not exhibit effect of decreasing CFPP by the addtition of a cold flowability improver.
  • those oils which contained n-paraffin in an amount of not smaller than 0.1 wt.% and below 0.6 wt.% and wax component which separated out at a temperature 10 °C below the cloud point in an amount of below 4 wt. % showed decrease in CFPP with the cold flowability improver. Thhis effect was much more excellent with sample oils of which the wax content was not smaller than 0.2 wt.% and below 0.5 wt.%.
  • CFPP of fuel oils decreased widely particularly when an ethylene-vinyl acetate copolymer having an ethylene content of 60 to 80 wt.% and a number average molecular weight of 1,000 to 4,000 was used as a cold flowability improver. Among them, remarkable effect was observed with those copolymers which had a molecular weight distribution of not greater than 4.0 and contained not more than 6 methyl terminated side chains per 100 methylene units.

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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)
  • Liquid Carbonaceous Fuels (AREA)
EP19880306929 1987-07-28 1988-07-27 Verfahren zur Herstellung einer fliessverbesserten Brennölzusammensetzung Expired EP0301837B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP186651/87 1987-07-28
JP18665187 1987-07-28

Publications (2)

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EP0301837A1 true EP0301837A1 (de) 1989-02-01
EP0301837B1 EP0301837B1 (de) 1992-11-25

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EP (1) EP0301837B1 (de)
JP (1) JP2714748B2 (de)
CA (1) CA1339640C (de)
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Cited By (9)

* 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
WO1996034073A1 (en) * 1995-04-28 1996-10-31 Exxon Chemical Patents Inc. Fuel composition
EP0890633A1 (de) * 1997-07-08 1999-01-13 Clariant GmbH Brennstofföle auf Basis von Mitteldestillaten und Copolymeren aus Ethylen und ungesättigten Carbonsäureestern
EP0960930A1 (de) * 1998-05-15 1999-12-01 Tonen Corporation Dieselbrennölzusammensetzung
EP0967263A1 (de) * 1998-06-22 1999-12-29 Tonen Corporation Dieselbrennölzusammensetzung
US6846338B2 (en) 1997-07-08 2005-01-25 Clariant Gmbh Fuel oils based on middle distillates and copolymers of ethylene and unsaturated carboxylic esters
EP1690919A1 (de) * 2005-02-11 2006-08-16 Infineum International Limited Kraftstoffölzusammensetzungen
EP1391498A4 (de) * 2001-05-08 2009-08-12 Sanyo Chemical Ind Ltd Fliessfähigkeitsverbesserer und brennölzusammensetzung
CN104531240A (zh) * 2014-11-27 2015-04-22 陕西省石油化工研究设计院 柴油低温流动改进剂

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4715287B2 (ja) * 2005-04-28 2011-07-06 日油株式会社 燃料油用流動性向上剤
FR2903418B1 (fr) * 2006-07-10 2012-09-28 Total France Utilisation de composes revelateurs d'efficacite des additifs de filtrabilite dans des distillats hydrocarbones, et composition synergique les contenant.
US8597502B2 (en) 2007-09-28 2013-12-03 Japan Oil, Gas And Metals National Corporation Method of manufacturing diesel fuel base stock and diesel fuel base stock thereof

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1264638A (de) * 1968-09-17 1972-02-23
GB1264684A (de) * 1968-09-17 1972-02-23
FR2307032A1 (fr) * 1975-04-07 1976-11-05 Exxon Research Engineering Co Additifs polymeres ameliorant les proprietes des huiles hydrocarbonees
US4210424A (en) * 1978-11-03 1980-07-01 Exxon Research & Engineering Co. Combination of ethylene polymer, normal paraffinic wax and nitrogen containing compound (stabilized, if desired, with one or more compatibility additives) to improve cold flow properties of distillate fuel oils
US4354011A (en) * 1978-10-02 1982-10-12 Exxon Research & Engineering Co. Copolymers of ethylene and ethylenically unsaturated monomers, process for their preparation and distillate oil containing said copolymers
EP0061895B1 (de) * 1981-03-31 1986-03-05 Exxon Research And Engineering Company Zusatz zur Verbesserung des Fliessverhaltens von Destillat-Treibstoffen und Konzentrate daraus
EP0184048A1 (de) * 1984-12-06 1986-06-11 QUANTUM CHEMICAL CORPORATION (a Virginia corp.) Als Fliesspunkt erniedrigende in Destillatölen verwendbare Terpolymere von Ethylen, Vinylacetat und Isobutylen
EP0187488A1 (de) * 1984-12-12 1986-07-16 Exxon Research And Engineering Company Für Mitteldestillatsbrennstoffe fliessverbesserende Zusammensetzung

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1264638A (de) * 1968-09-17 1972-02-23
GB1264684A (de) * 1968-09-17 1972-02-23
FR2307032A1 (fr) * 1975-04-07 1976-11-05 Exxon Research Engineering Co Additifs polymeres ameliorant les proprietes des huiles hydrocarbonees
US4354011A (en) * 1978-10-02 1982-10-12 Exxon Research & Engineering Co. Copolymers of ethylene and ethylenically unsaturated monomers, process for their preparation and distillate oil containing said copolymers
US4210424A (en) * 1978-11-03 1980-07-01 Exxon Research & Engineering Co. Combination of ethylene polymer, normal paraffinic wax and nitrogen containing compound (stabilized, if desired, with one or more compatibility additives) to improve cold flow properties of distillate fuel oils
EP0061895B1 (de) * 1981-03-31 1986-03-05 Exxon Research And Engineering Company Zusatz zur Verbesserung des Fliessverhaltens von Destillat-Treibstoffen und Konzentrate daraus
EP0184048A1 (de) * 1984-12-06 1986-06-11 QUANTUM CHEMICAL CORPORATION (a Virginia corp.) Als Fliesspunkt erniedrigende in Destillatölen verwendbare Terpolymere von Ethylen, Vinylacetat und Isobutylen
EP0187488A1 (de) * 1984-12-12 1986-07-16 Exxon Research And Engineering Company Für Mitteldestillatsbrennstoffe fliessverbesserende Zusammensetzung

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
WO1996034073A1 (en) * 1995-04-28 1996-10-31 Exxon Chemical Patents Inc. Fuel composition
US6015441A (en) * 1995-04-28 2000-01-18 Exxon Chemical Patents, Inc. Fuel composition
EP0890633A1 (de) * 1997-07-08 1999-01-13 Clariant GmbH Brennstofföle auf Basis von Mitteldestillaten und Copolymeren aus Ethylen und ungesättigten Carbonsäureestern
US6846338B2 (en) 1997-07-08 2005-01-25 Clariant Gmbh Fuel oils based on middle distillates and copolymers of ethylene and unsaturated carboxylic esters
US6136049A (en) * 1998-05-15 2000-10-24 Tonen Corporation Diesel fuel oil composition
EP0960930A1 (de) * 1998-05-15 1999-12-01 Tonen Corporation Dieselbrennölzusammensetzung
US6136050A (en) * 1998-06-22 2000-10-24 Tonen Corporation Diesel fuel oil composition
EP0967263A1 (de) * 1998-06-22 1999-12-29 Tonen Corporation Dieselbrennölzusammensetzung
EP1391498A4 (de) * 2001-05-08 2009-08-12 Sanyo Chemical Ind Ltd Fliessfähigkeitsverbesserer und brennölzusammensetzung
EP1690919A1 (de) * 2005-02-11 2006-08-16 Infineum International Limited Kraftstoffölzusammensetzungen
CN104531240A (zh) * 2014-11-27 2015-04-22 陕西省石油化工研究设计院 柴油低温流动改进剂
CN104531240B (zh) * 2014-11-27 2016-01-06 陕西省石油化工研究设计院 柴油低温流动改进剂

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Publication number Publication date
JPH06192666A (ja) 1994-07-12
DE3876165D1 (de) 1993-01-07
DE3876165T2 (de) 1993-05-19
DE3876165T4 (de) 1994-02-10
EP0301837B1 (de) 1992-11-25
JP2714748B2 (ja) 1998-02-16
CA1339640C (en) 1998-01-27

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