EP0405270B1 - Procédé d'amélioration de la fluidité d'huiles minérales et de distillats d'huiles minérales - Google Patents

Procédé d'amélioration de la fluidité d'huiles minérales et de distillats d'huiles minérales Download PDF

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Publication number
EP0405270B1
EP0405270B1 EP90111397A EP90111397A EP0405270B1 EP 0405270 B1 EP0405270 B1 EP 0405270B1 EP 90111397 A EP90111397 A EP 90111397A EP 90111397 A EP90111397 A EP 90111397A EP 0405270 B1 EP0405270 B1 EP 0405270B1
Authority
EP
European Patent Office
Prior art keywords
vinyl acetate
ethylene
mineral oil
weight
flowability
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP90111397A
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German (de)
English (en)
Other versions
EP0405270A1 (fr
Inventor
Wolfgang Dr. Dipl.-Chem. Payer
Werner Dr. Dipl.-Chem. Reimann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
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Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to AT90111397T priority Critical patent/ATE82587T1/de
Publication of EP0405270A1 publication Critical patent/EP0405270A1/fr
Application granted granted Critical
Publication of EP0405270B1 publication Critical patent/EP0405270B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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 a process for improving the flowability of mineral oils and mineral oil distillates by adding mixtures of ethylene-vinyl acetate copolymers and ethylene-vinyl acetate-N-vinylpyrrolidone terpolymers.
  • mineral oils and mineral oil distillates contain different amounts of paraffin, which is deposited at low temperatures in the form of platelet-shaped crystals in which oil is still trapped. This significantly affects the flowability of mineral oils and mineral oil distillates. This leads e.g. in the case of diesel fuel for clogging of filters, with the result that the supply of the fuel to the combustion units, such as engines or jet engines, takes place unevenly or is completely interrupted. Malfunctions can also occur during the transport of heating oils in incineration plants if such wax deposits occur due to low temperatures.
  • the remedy is to add large quantities or to mix the mineral oil or mineral oil distillate with low-boiling hydrocarbons.
  • DE-A-26 39 672 describes mixtures of polymers with an ethylene skeleton and copolymers of C2- to C50-olefins, which can lead to a synergistic improvement in the flow properties of distillate hydrocarbon oils in the cold.
  • US-A-40 19 878 discloses mixtures consisting of an ethylene-containing polymer, beeswax, ozokerite and / or a long-chain alpha-olefin.
  • the object was therefore to provide additives which have an even greater range of uses than the known flow improvers. They are also intended to increase the flowability of oils in which the known additives have little or no effect.
  • the invention consists in a method for improving the flowability of mineral oils and mineral oil distillates. It is characterized in that mixtures of an ethylene-vinyl acetate copolymer and an ethylene-vinyl acetate-N-vinylpyrrolidone terpolymer are added to the mineral oils or mineral oil distillates.
  • the process according to the invention effectively suppresses the separation of paraffins from mineral oils and mineral oil distillates and any paraffin crystals which have separated out in suspension holds.
  • the additives used according to the new process thus counteract an increase in the viscosity of the hydrocarbon mixtures as temperatures drop and lower the pour point.
  • the claimed working method has proven itself to improve the flowability of mineral oils and their distillation products, regardless of their qualitative and quantitative composition. It is particularly important that the two components reinforce each other synergistically. The effectiveness of the polymer mixture is therefore greater than the sum of the effectiveness of its components.
  • the ethylene-vinyl acetate copolymers used according to the invention contain 20 to 40% by weight of vinyl acetate. Copolymers with 25 to 35% by weight of vinyl acetate have proven particularly useful. Its viscosity, measured according to the German standard DIN 53 019 in a rotary viscometer (manufacturer: Haake) at 140 ° C, is 30 to 1000 mPa.s, in particular 30 to 250 mPa.s.
  • Each 100 CH2 groups have 1 to 10 and preferably 2 to 7 CH3 groups in the side chains, which do not result from the acetate residue of the vinyl acetate.
  • the number of CH3 groups is determined by H-NMR spectroscopy.
  • the production of the ethylene-vinyl acetate copolymers is known. It can e.g. by polymerization of the monomer mixture at pressures of 5 to 15 MPa and temperatures of 70 to 150 ° C in the presence of free radical initiators.
  • An organic solvent or suspension medium such as toluene can be used as the reaction medium.
  • the ethylene-vinyl acetate-N-vinylpyrrolidone terpolymers used as the second constituent of the flow improver mixture contain 15 to 50% by weight, in particular 20 to 35% by weight of vinyl acetate and 0.5 to 10% by weight, in particular 1.0 to 5.0% by weight of N-vinylpyrrolidone.
  • Their viscosity measured in the same way as for the ethylene-vinyl acetate copolymers, is 100 to 5000 mPa.s and in particular 150 to 1500 mPa.s.
  • ethylene-vinyl acetate-N-vinylpyrrolidone terpolymers The production of ethylene-vinyl acetate-N-vinylpyrrolidone terpolymers is known. It takes place e.g. by polymerization of the monomer mixture at pressures above 5 MPa and temperatures above 60 ° C in the presence of free radical initiators in autoclaves. Organic solvents which dissolve ⁇ 5% by weight of ethylene are used as the reaction medium. Methanol, t-butanol, benzene, dioxane are suitable (cf. FR 1 392 354).
  • the weight ratio of the two polymers in the additive mixture can be varied within wide limits. It has proven useful to use ethylene-vinyl acetate copolymer and ethylene-vinyl acetate-N-vinylpyrrolidone terpolymer in a weight ratio of 1: 1 to 100: 1. Mixtures which contain copolymer and terpolymer in a weight ratio of 3: 1 to 20: 1 are preferred.
  • the process according to the invention improves both the flowability of mineral oils and of mineral oil distillates.
  • mineral oils is understood here to mean in particular crude oils and distillation residues, such as heavy fuel oil.
  • Mineral oil distillates are hydrocarbon fractions with a boiling temperature between approximately 150 and 400 ° C. These include, for example, petroleum, light heating oils and diesel fuels. Middle distillates such as heating oil EL and diesel fuel are of particular importance.
  • the mixture of the two polymers is added to mineral oils or the mineral oil distillates in the form of solutions which contain 20 to 70% by weight (based on the solution) of the polymers.
  • Suitable solvents are aliphatic or aromatic hydrocarbons or hydrocarbon mixtures, e.g. Gasoline fractions. Kerosene is particularly suitable.
  • the amount of polymer, based on mineral oil or mineral oil fractions, should be 0.001 to 2, preferably 0.005 to 0.5% by weight.
  • the polymer mixtures can be used alone or together with other additives, e.g. with other pour point depressants or dewaxing aids, with corrosion inhibitors, antioxidants, sludge inhibitors and additives to lower the cloud point.
  • additives e.g. with other pour point depressants or dewaxing aids, with corrosion inhibitors, antioxidants, sludge inhibitors and additives to lower the cloud point.
  • Examples 1 to 4 relate to the process according to the invention.
  • Examples 5 to 7 show the results of comparative experiments which are obtained using ethylene-vinyl acetate copolymers alone (Examples 5 and 6) and an ethylene-vinyl acetate-N-vinylpyrrolidone terpolymer alone (Example 7).
  • the vinyl acetate content in the polymers is determined using the pyrolysis method. For this purpose, 200 mg of the polymer are heated with 300 mg of pure polyethylene in a pyrolysis flask to 450 ° C. for 5 minutes and the cracked gases are collected in a 250 ml round-bottom flask. The resulting acetic acid is reacted with a NaJ / KJO3 solution and the iodine released is titrated with Na2S2O3 solution.
  • the N-vinylpyrrolidone content in the polymer is calculated from the nitrogen content of the polymer determined according to Dumas.
  • Table 2 contains information on the effectiveness of the process according to the invention for improving the flowability of mineral oils and mineral oil distillates.

Landscapes

  • 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)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Fats And Perfumes (AREA)

Claims (5)

  1. Procédé d'amélioration de la fluidité d'huiles minérales et de distillats d'huiles minérales caractérisé en ce que l'on ajoute aux huiles minérales ou aux distillats d'huiles minérales, des mélanges composés d'un copolymère éthylène-acétate de vinyle et d'un terpolymère éthylène-acétate de vinyle-N-vinylpyrrolidone.
  2. Procédé selon la revendication 1, caractérisé en ce que le copolymère éthylène-acétate de vinyle contient de 20 à 40 % en poids, de préférence de 25 à 35 % en poids d'acétate de vinyle, possède une viscosité, mesurée à 140°C, de 30 à 1000, de préférence de 30 à 250 mPa.s, et que pour 100 groupes CH₂ il y a 1 à 10, de préférence 2 à 7 groupes CH₃ dans les chaînes latérales ne provenant pas du radical acétate de l'acétate de vinyle.
  3. Procédé selon la revendication 1 caractérisé en ce que le terpolymère éthylène-acétate de vinyle-N-vinylpyrrolidone contient de 15 à 50 % en poids, de préférence de 20 à 35 % en poids d'acétate de vinyle, de 0,5 à 10 % en poids, de préférence de 1,0 à 5,0 % en poids de N-vinylpyrrolidone, et possède une viscosité, mesurée à 140°C, de 100 à 5000 mPa.s, en particulier de 150 à 1500 mPa.s.
  4. Procédé selon la revendication 1 caractérisé en ce que le copolymère éthylène-acétate de vinyle et le terpolymère éthylène-acétate de vinyle-N-vinylpyrrolidone sont utilisés dans un rapport pondéral de 1:1 à 100:1, de préférence de 3:1 à 20:1.
  5. Huile minérale ou distillat d'huile minérale ayant une fluidité améliorée caractérisé en ce qu'il ou elle contient de 0,001 à 2, de préférence de 0,005 à 0,5 % en poids d'un mélange composé d'un copolymère éthylène-acétate de vinyle et d'un terpolymère éthylène-acétate de vinyle-N-vinylpyrrolidone.
EP90111397A 1989-06-29 1990-06-16 Procédé d'amélioration de la fluidité d'huiles minérales et de distillats d'huiles minérales Expired - Lifetime EP0405270B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT90111397T ATE82587T1 (de) 1989-06-29 1990-06-16 Verfahren zur verbesserung der fliessfaehigkeit von mineraloelen und mineraloeldestillaten.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3921279 1989-06-29
DE3921279A DE3921279A1 (de) 1989-06-29 1989-06-29 Verfahren zur verbesserung der fliessfaehigkeit von mineraloelen und mineraloeldestillaten

Publications (2)

Publication Number Publication Date
EP0405270A1 EP0405270A1 (fr) 1991-01-02
EP0405270B1 true EP0405270B1 (fr) 1992-11-19

Family

ID=6383843

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90111397A Expired - Lifetime EP0405270B1 (fr) 1989-06-29 1990-06-16 Procédé d'amélioration de la fluidité d'huiles minérales et de distillats d'huiles minérales

Country Status (9)

Country Link
EP (1) EP0405270B1 (fr)
JP (1) JPH0768505B2 (fr)
KR (1) KR930011928B1 (fr)
AT (1) ATE82587T1 (fr)
AU (1) AU624965B2 (fr)
CA (1) CA2020104A1 (fr)
DE (2) DE3921279A1 (fr)
ES (1) ES2054152T3 (fr)
ZA (1) ZA904894B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0857776A1 (fr) 1997-01-07 1998-08-12 Clariant GmbH Amélioration de la fluidité d'huiles minérales et de distillates d'huiles minérales par l'utilisation de résines alkylphénol-aldéhyde
WO2010081634A1 (fr) 2009-01-13 2010-07-22 Evonik Rohmax Additives Gmbh Compositions de carburant ayant un point de trouble amélioré et des propriétés améliorées au stockage
WO2011095249A1 (fr) 2010-02-05 2011-08-11 Evonik Rohmax Additives Gmbh Composition ayant une filtrabilité améliorée
DE10155774B4 (de) 2001-11-14 2020-07-02 Clariant Produkte (Deutschland) Gmbh Additive für schwefelarme Mineralöldestillate, umfassend einen Ester alkoxylierten Glycerins und einen polaren stickstoffhaltigen Paraffindispergator

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19739271A1 (de) * 1997-09-08 1999-03-11 Clariant Gmbh Additiv zur Verbesserung der Fließfähigkeit von Mineralölen und Mineralöldestillaten
DE19816797C2 (de) * 1998-04-16 2001-08-02 Clariant Gmbh Verwendung von stickstoffhaltigen Ethylencopolymeren zur Herstellung von Brennstoffölen mit verbesserter Schmierwirkung
DE19823565A1 (de) 1998-05-27 1999-12-02 Clariant Gmbh Mischungen von Copolymeren mit verbesserter Schmierwirkung
WO2001088066A1 (fr) * 2000-05-19 2001-11-22 Nippon Mitsubishi Oil Corporation Additif pour carburant diesel et composition de carburant diesel
CA2412740A1 (fr) 2000-06-15 2002-12-13 Clariant International Ltd Additif pour ameliorer la fuidite a froid et la stabilite au stockage du petrole brut
DE10155748B4 (de) 2001-11-14 2009-04-23 Clariant Produkte (Deutschland) Gmbh Schwefelarme Mineralöldestillate mit verbesserten Kälteeigenschaften, umfassend einen Ester eines alkoxylierten Polyols und ein Copolymer aus Ethylen und ungesättigten Estern
JP4484458B2 (ja) 2002-07-09 2010-06-16 クラリアント・プロドゥクテ・（ドイチュラント）・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 高度に脱硫された燃料油用の酸化安定性潤滑剤添加剤
ES2399626T3 (es) 2002-07-09 2013-04-02 Clariant Produkte (Deutschland) Gmbh Agente mejorador de la fluidez en frío para aceites combustibles de procedencia vegetal o animal
DE10349850C5 (de) 2003-10-25 2011-12-08 Clariant Produkte (Deutschland) Gmbh Kaltfließverbesserer für Brennstofföle pflanzlichen oder tierischen Ursprungs
DE10349851B4 (de) 2003-10-25 2008-06-19 Clariant Produkte (Deutschland) Gmbh Kaltfließverbesserer für Brennstofföle pflanzlichen oder tierischen Ursprungs
DE10357878C5 (de) 2003-12-11 2013-07-25 Clariant Produkte (Deutschland) Gmbh Brennstofföle aus Mitteldestillaten und Ölen pflanzlichen oder tierischen Ursprungs mit verbesserten Kälteeigenschaften
DE10357880B4 (de) 2003-12-11 2008-05-29 Clariant Produkte (Deutschland) Gmbh Brennstofföle aus Mitteldestillaten und Ölen pflanzlichen oder tierischen Ursprungs mit verbesserten Kälteeigenschaften

Family Cites Families (9)

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Publication number Priority date Publication date Assignee Title
CA658216A (en) * 1963-02-19 Esso Research And Engineering Company Multi-purpose additive for petroleum fuels
GB885348A (en) * 1960-02-26 1961-12-28 Exxon Research Engineering Co Improved hydrocarbon fuel oil compositions
FR1392354A (fr) * 1963-05-09 1965-03-12 Bayer Ag Procédé de préparation de copolymères d'éthylène
FR96138E (fr) * 1967-11-30 1972-05-19 Exxon Research Engineering Co Compositions copolymeres pour abaisser la viscosité de produits pétroliers.
US3620696A (en) * 1968-09-17 1971-11-16 Exxon Research Engineering Co Fuel oil with improved flow properties
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
DE3112456A1 (de) * 1981-03-28 1982-10-07 Hoechst Ag, 6000 Frankfurt "verfahren zur verbesserung der fliessfaehigkeit von mineraloelen"
JPS5880386A (ja) * 1981-11-06 1983-05-14 Nippon Cooper Kk 燃料油添加剤
DE3621395A1 (de) * 1986-06-26 1988-01-28 Ruhrchemie Ag Verfahren zur verbesserung der fliessfaehigkeit von mineraloelen und mineraloeldestillaten

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0857776A1 (fr) 1997-01-07 1998-08-12 Clariant GmbH Amélioration de la fluidité d'huiles minérales et de distillates d'huiles minérales par l'utilisation de résines alkylphénol-aldéhyde
DE10155774B4 (de) 2001-11-14 2020-07-02 Clariant Produkte (Deutschland) Gmbh Additive für schwefelarme Mineralöldestillate, umfassend einen Ester alkoxylierten Glycerins und einen polaren stickstoffhaltigen Paraffindispergator
WO2010081634A1 (fr) 2009-01-13 2010-07-22 Evonik Rohmax Additives Gmbh Compositions de carburant ayant un point de trouble amélioré et des propriétés améliorées au stockage
WO2011095249A1 (fr) 2010-02-05 2011-08-11 Evonik Rohmax Additives Gmbh Composition ayant une filtrabilité améliorée

Also Published As

Publication number Publication date
ZA904894B (en) 1991-04-24
ES2054152T3 (es) 1994-08-01
EP0405270A1 (fr) 1991-01-02
JPH0768505B2 (ja) 1995-07-26
KR910001004A (ko) 1991-01-30
AU5791090A (en) 1991-01-03
AU624965B2 (en) 1992-06-25
JPH0339385A (ja) 1991-02-20
DE59000480D1 (de) 1992-12-24
KR930011928B1 (ko) 1993-12-22
CA2020104A1 (fr) 1990-12-30
ATE82587T1 (de) 1992-12-15
DE3921279A1 (de) 1991-01-03

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