EP0061696B1 - Procédé d'amélioration de l'écoulement des huiles minérales - Google Patents

Procédé d'amélioration de l'écoulement des huiles minérales Download PDF

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Publication number
EP0061696B1
EP0061696B1 EP82102388A EP82102388A EP0061696B1 EP 0061696 B1 EP0061696 B1 EP 0061696B1 EP 82102388 A EP82102388 A EP 82102388A EP 82102388 A EP82102388 A EP 82102388A EP 0061696 B1 EP0061696 B1 EP 0061696B1
Authority
EP
European Patent Office
Prior art keywords
ethylene
weight
copolymer
vinyl
middle distillate
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
Application number
EP82102388A
Other languages
German (de)
English (en)
Other versions
EP0061696A3 (en
EP0061696A2 (fr
Inventor
Karl Heinz Dr. Heier
Roland Böhm
John Victor Dr. Hobes
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
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0061696A2 publication Critical patent/EP0061696A2/fr
Publication of EP0061696A3 publication Critical patent/EP0061696A3/de
Application granted granted Critical
Publication of EP0061696B1 publication Critical patent/EP0061696B1/fr
Expired 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
    • C10L1/234—Macromolecular compounds
    • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
    • C10L1/2362—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing nitrile 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, 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
    • C10L1/2364—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, 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
    • 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
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2462—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds
    • C10L1/2468—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds obtained by reactions involving only carbon to carbon unsaturated bonds; derivatives thereof

Definitions

  • copolymers are obtained by high-pressure polymerization in the presence of radical-forming compounds at pressures of about 1000 to 8000, preferably 1500 to 2500 bar, temperatures of 100 to 350, preferably 200 to 350 ° C. and an average residence time of up to 150 seconds.
  • the ethylene used for the polymerization is used in the purity customary for polymerization reactions of at least 99.9%.
  • suitable N-vinyl acid amides are vinylformamide, vinyl acetamide, vinyl N-methylacetamide and vinyl propionamide.
  • the proportion of vinyl acid amide in the copolymer is 0.1 to 40% by weight and, accordingly, the proportion of ethylene is 99.9 to 60% by weight.
  • Vinyl-N-methylacetamide is preferably copolymerized with ethylene in amounts of 0.5 to 30% by weight.
  • the copolymer may contain up to 40 wt .-% further, copolymerizable with ethylene monomers, particularly acrylate and Vinylester such as methacrylate, ethyl acrylate, butyl acrylate, 2 - ethylhexyl acrylate or Essigklarevinylester.
  • ethylene monomers particularly acrylate and Vinylester such as methacrylate, ethyl acrylate, butyl acrylate, 2 - ethylhexyl acrylate or Essigklavinylester.
  • ethylene other monomers copolymerizable with ethylene are suitable, for example C 3 -C 8 -alkenes, vinyl and alkenyl ethers, vinyl and alkenyl alcohols, N-vinyl and N-alkenyl compounds, such as N-vinylpyrrolidone, N-vinylcarbazole, N Vinyl caprolactam, acrylic and methacrylamides, acrylic and methacrylonitriles, alkenyl halides such as vinyl fluoride and vinylidene fluoride, vinyl and alkenyl ketones, vinyl and alkenyl sulfones and sulfonates and styrene.
  • carbon monoxide and sulfur dioxide can also be copolymerized.
  • the polymerization is carried out under the conditions indicated above in the presence of catalytic amounts of free radical initiators, for example with 2 to 250 mol ppm of oxygen, based on the ethylene.
  • free radical initiators for example with 2 to 250 mol ppm of oxygen, based on the ethylene.
  • peroxides such as tert-butyl perbenzoate, dilauroyl peroxide, di-tert-butyl peroxide or azo-butyrononitrile in amounts of 2 to 200 mol ppm, based on ethylene, can also be used as the initiator.
  • the molecular weight is adjusted by adding moderators in amounts of 2 to 25% by volume, depending on the desired molecular weight.
  • the aim is to have low molecular weight copolymers with molecular weights of 500 to 10,000, determined according to K. Rast, Ber. 550, 1922, pp. 1051 and 3727.
  • copolymers of ethylene and vinyl acid amide obtained in this way show an improvement in the flow properties of mineral oils such as middle distillates from crude oil distillation and also of the crude oil itself, because they influence the crystal growth of the paraffin which precipitates in the cold in such a way that the paraffin crystals remain small and do not agglomerate that they can pass through the filters.
  • These copolymers are normally added to the mineral oil in the form of approx. 40-45% solutions in an aromatic hydrocarbon.
  • the amount of copolymer based on the mineral oil should be 0.001 to 2, preferably 0.005 to 0.5% by weight.
  • these copolymers can be used alone or together with other oil additives, such as, for example, with other pour point depressants or dewaxing aids, corrosion inhibitors, antioxidants or sludge inhibitors.
  • the N-ethylene-vinyl acid amide copolymers are also suitable as adhesives, as coating materials, for the production of stretch, skin and shrink films, for injection molding and for pipe and cable sheathing.
  • a reaction mixture consisting of 98.7% by weight of ethylene and 1.3% by weight of vinyl-N-methylacetamide (VIMA) is compressed to 2000 bar.
  • the polymerization is initiated with 30 ppm butyl peroctoate (in the form of a gasoline solution).
  • the reaction temperature is 218 ° C.
  • the melt index of the copolymer obtained is 2.7 g / 10 min, the density is 0.927 g / cm 3 . It contains 0.9% by weight of VIMA in polymer-bound form.
  • the mechanical values of the copolymer are:
  • a reaction mixture consisting of 94.3% by weight of ethylene and 5.7% by weight of VIMA is compressed to 2100 bar.
  • the polymerization is initiated with 35 ppm t-butyl peroctoate.
  • the reaction temperature is 210 ° C. 5.7% by weight of VIMA are incorporated.
  • the melt index of the get NEN copolymer is 1.8 g / 10 min, the density is 0.929 g / cm 3 .
  • the mechanical values of the copolymer are:
  • a reaction mixture consisting of 88.8% by weight of ethylene and 11.2% by weight of VIMA is compressed to 2100 bar and polymerized at a temperature around 210 ° C. using 40 ppm butyl peroctoate as the initiator.
  • a copolymer with 10.3% by weight of VIMA, a melt index of 4.3 g / 10 min and a density of 0.931 g / cm 3 is obtained .
  • the mechanical values of the copolymer are:
  • the yield stress and the tensile strength were determined according to DIN 53455 and the impact strength according to DIN 53448.
  • a middle distillate with an initial boiling point of 178 ° C., 5% point of 201 ° C., 95% point of 359 ° C., end of boiling point 376 ° C. and cloud point of -1 ° C. was mixed with 300 ppm of a 45% solution in xylene of a copolymer of 95% by weight. -% ethylene and 5 wt .-% vinyl methylacetamide with a viscosity of 600 mPas.
  • the middle distillate treated in this way had a CFPP value of -11 ° C.
  • a middle distillate according to Example 4 was mixed with 300 ppm of a 45% solution in xylene of a copolymer of 70% by weight of ethylene, 25% by weight of t-butyl acrylate and 5% by weight of vinyl methylacetamide with a viscosity of 600 mPas.
  • the middle distillate treated in this way had a CFPP value of -13 ° C.
  • a paraffin-rich middle distillate with a start of boiling 172 ° C, 5% point 190 ° C, 95% point 359 ° C, end of boiling 384 ° C and a cloud point of + 8 ° C was mixed with 300 ppm of a 45% solution in xylene of a copolymer 90% by weight of ethylene and 10% by weight of vinyl methylacetamide with a viscosity of 600 mPas.
  • the middle distillate treated in this way had a CFPP value of -6 ° C.
  • a middle distillate according to Example 6 was mixed with 300 ppm of a 45% solution in xylene of a copolymer of 86.8% by weight of ethylene, 6.6% by weight of vinyl acetate and 6.6% by weight of vinyl methylacetamide with a viscosity of 600 mPas.
  • the middle distillate treated in this way had a CFPP value of -6 ° C.
  • a middle distillate with an initial boiling point of 167 ° C., 5% point 175 ° C., 95% point 372 ° C. and cloud point + 5 ° C. was mixed with 300 ppm of a 45% solution in xylene of a copolymer of 68% by weight of ethylene and 32 % By weight of vinyl acetate with a viscosity of 900 mPas.
  • the middle distillate treated in this way had a CFPP value of -8 ° C.
  • a middle distillate according to Example 4 was mixed with 300 ppm of a 45% solution in xylene of a copolymer of 70% by weight of ethylene and 30% by weight of butyl acrylate with a viscosity of 600 mPas.
  • the middle distillate treated in this way had a CFPP value of -7 ° C.
  • the middle distillate according to Example 6 was mixed with 300 ppm of a 45% solution in xylene of a copolymer of 85% by weight of ethylene and 15% by weight of vinyl acetate with a viscosity of 1500 mPas.
  • the middle distillate treated in this way showed a CFPP value of + 1 ° C.
  • the viscosity in the above examples was measured at 140 ° C. in a rotary viscometer (Rotovisko).
  • the CFPP value is the cold filter clogging point and indicates the temperature at which the oil in the test equipment stops flowing. This test is described in "Journal of the Institute of Petroleum", Vol. 52, No. 510, June 1966, pp. 173-185 and in DIN 51428.
  • the copolymer to be used according to the invention not only brings about a significant improvement in the flow properties of mineral oils and mineral oil products when it is used alone, but moreover also shows a pronounced synergistic effect when copolymers other than pour point depressants are also used. This is clear from Example 8, where a significantly better effect was measured for the mixture of ethylene-vinyl acetate copolymer and ethylene-vinyl methylacetamide copolymer than for the same amount of each of these two copolymers alone.

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

Claims (6)

1. Procédé pour améliorer la fluidité d'huiles minérales, procédé caractérisé en ce qu'on ajoute à l'huile minérale un copolymère N-vinyl-amidei éthylène.
2. Procédé selon la revendication 1, caractérisé en ce qu'on ajoute à l'huile minérale un copolymère constitué de 60 à 99,9% en poids d'éthylène et de 0,1 à 40% en poids de vinyl-amide.
3. Procédé selon la revendication 1, caractérisé en ce qu'on ajoute à l'huile minérale un copolymère vinyl-amide/éthylène qui contient, en plus, jusqu'à 40% en poids d'un monomère copolymé- risable avec l'éthylène.
4. Procédé selon la revendication 1, caractérisé en ce que le copolymère est ajouté à l'huile minérale en une quantité de 0,001 à 2% en poids.
5. Procédé selon la revendication 1, caractérisé en ce que le copolymère vinylamide/éthylène est utilisé avec d'autres copolymères.
6. Procédé selon la revendication 1, caractérisé en ce que le copolymère vinylamide/éthylène est utilisé avec un copolymère éthylène/acétate de vinyle.
EP82102388A 1981-03-28 1982-03-23 Procédé d'amélioration de l'écoulement des huiles minérales Expired EP0061696B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813112456 DE3112456A1 (de) 1981-03-28 1981-03-28 "verfahren zur verbesserung der fliessfaehigkeit von mineraloelen"
DE3112456 1981-03-28

Publications (3)

Publication Number Publication Date
EP0061696A2 EP0061696A2 (fr) 1982-10-06
EP0061696A3 EP0061696A3 (en) 1983-01-26
EP0061696B1 true EP0061696B1 (fr) 1985-05-02

Family

ID=6128660

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82102388A Expired EP0061696B1 (fr) 1981-03-28 1982-03-23 Procédé d'amélioration de l'écoulement des huiles minérales

Country Status (6)

Country Link
US (1) US4556499A (fr)
EP (1) EP0061696B1 (fr)
JP (1) JPS57170994A (fr)
CA (1) CA1191834A (fr)
DE (2) DE3112456A1 (fr)
ZA (1) ZA822078B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4769043A (en) * 1984-08-20 1988-09-06 Texaco Inc. Oil containing dispersant VII olefin copolymer
US5814110A (en) * 1986-09-24 1998-09-29 Exxon Chemical Patents Inc. Chemical compositions and use as fuel additives
DE3732721A1 (de) * 1987-09-29 1989-04-06 Ruhrchemie Ag Copolymerisate aus ethylen und methoxyessigsaeurevinylester und ihre verwendung als additive fuer mineraloeldestillate
JP2508783B2 (ja) * 1988-01-26 1996-06-19 日本油脂株式会社 燃料油用流動性向上剤
US4926582A (en) * 1988-06-02 1990-05-22 E. I. Dupont De Nemours & Company Low pour crude oil compositions
DE3921279A1 (de) * 1989-06-29 1991-01-03 Hoechst Ag Verfahren zur verbesserung der fliessfaehigkeit von mineraloelen und mineraloeldestillaten
US5078917A (en) * 1989-11-01 1992-01-07 Functional Products Incorporated White oil pour point depressants
US5432292A (en) * 1992-11-20 1995-07-11 Colorado School Of Mines Method for controlling clathrate hydrates in fluid systems
US5420370A (en) * 1992-11-20 1995-05-30 Colorado School Of Mines Method for controlling clathrate hydrates in fluid systems
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
US6495495B1 (en) 1999-08-20 2002-12-17 The Lubrizol Corporation Filterability improver

Family Cites Families (17)

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Publication number Priority date Publication date Assignee Title
BE539718A (fr) * 1954-07-12
US3089832A (en) * 1955-12-01 1963-05-14 Exxon Research Engineering Co Polymeric lubricating oil additives
US2958590A (en) * 1957-10-15 1960-11-01 Exxon Research Engineering Co Stabilized hydrocarbon fuel oil composition
NL238305A (fr) * 1958-04-21
US3015546A (en) * 1958-10-28 1962-01-02 Exxon Research Engineering Co Gasolines inhibited against the formation of deposits, sludge and varnish
FR1266384A (fr) * 1960-09-01 1961-07-07 Exxon Research Engineering Co Carburants pour moteurs à combustion interne
US3037850A (en) * 1960-10-18 1962-06-05 Exxon Research Engineering Co Middle distillate pour point depressants
BE637124A (fr) * 1962-09-07
NL148099B (nl) * 1966-03-17 1975-12-15 Shell Int Research Werkwijze voor het verlagen van het vloeipunt van een brandstofmengsel.
FR96138E (fr) * 1967-11-30 1972-05-19 Exxon Research Engineering Co Compositions copolymeres pour abaisser la viscosité de produits pétroliers.
FR96140E (fr) * 1967-11-30 1972-05-19
US3620696A (en) * 1968-09-17 1971-11-16 Exxon Research Engineering Co Fuel oil with improved flow properties
US3658493A (en) * 1969-09-15 1972-04-25 Exxon Research Engineering Co Distillate fuel oil containing nitrogen-containing salts or amides as was crystal modifiers
US3966428A (en) * 1973-10-31 1976-06-29 Exxon Research And Engineering Company Ethylene backbone polymers in combination with ester polymers having long alkyl side chains are low viscosity distillate fuel cold flow improvers
US4153422A (en) * 1975-04-07 1979-05-08 Exxon Research & Engineering Co. Polymer combinations useful in distillate hydrocarbon oils to improve cold flow properties
US4261703A (en) * 1978-05-25 1981-04-14 Exxon Research & Engineering Co. Additive combinations and fuels containing them
US4211534A (en) * 1978-05-25 1980-07-08 Exxon Research & Engineering Co. Combination of ethylene polymer, polymer having alkyl side chains, and nitrogen containing compound to improve cold flow properties of distillate fuel oils

Also Published As

Publication number Publication date
US4556499A (en) 1985-12-03
ZA822078B (en) 1983-02-23
EP0061696A3 (en) 1983-01-26
JPS57170994A (en) 1982-10-21
EP0061696A2 (fr) 1982-10-06
CA1191834A (fr) 1985-08-13
DE3112456A1 (de) 1982-10-07
DE3263354D1 (en) 1985-06-05

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