EP0111883B2 - Utilisation de copolymères d'éthylène comme additifs pour les huiles minérales - Google Patents

Utilisation de copolymères d'éthylène comme additifs pour les huiles minérales Download PDF

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Publication number
EP0111883B2
EP0111883B2 EP83112556A EP83112556A EP0111883B2 EP 0111883 B2 EP0111883 B2 EP 0111883B2 EP 83112556 A EP83112556 A EP 83112556A EP 83112556 A EP83112556 A EP 83112556A EP 0111883 B2 EP0111883 B2 EP 0111883B2
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EP
European Patent Office
Prior art keywords
weight
vinyl
waxy
units
copolymerisates
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
EP83112556A
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German (de)
English (en)
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EP0111883A1 (fr
EP0111883B1 (fr
Inventor
John Dr. Dipl.-Chem. Hobes
Karl Heinz Dr. Dipl.-Chem. Heier
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
Ruhrchemie AG
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Application filed by Hoechst AG, Ruhrchemie AG filed Critical Hoechst AG
Priority to AT83112556T priority Critical patent/ATE15064T1/de
Publication of EP0111883A1 publication Critical patent/EP0111883A1/fr
Publication of EP0111883B1 publication Critical patent/EP0111883B1/fr
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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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1625—Hydrocarbons macromolecular compounds
    • C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
    • C10L1/1641—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aliphatic monomers
    • 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
    • C10L1/1955—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds 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 an alcohol, ether, aldehyde, ketonic, ketal, acetal radical
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
    • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic

Definitions

  • the present invention relates to the use of copolymers of ethylene as pour point depressants and flow improvers for crude oils and middle distillates of crude oil distillation.
  • copolymers of ethylene with esters of vinyl alcohol, especially vinyl acetate are economically most important pour point depressants and flow improvers for crude oils and middle distillates.
  • Such copolymers and their use are e.g. described in DE-A 1 914756 and DE-A 2515805. From GB-A-1 235 836 it is known to use copolymers of ethylene and vinyl methyl ketone as flow improvers.
  • copolymers mentioned are generally prepared in autoclaves at temperatures from 80 to 150 ° C. and pressures from 50 to 150 bar with peroxides as initiators and in the presence of organic solvents as the reaction medium.
  • the present invention relates to the use of waxy copolymers with a molecular weight of 500 to 20,000, which consist of at least 60% by weight of ethylene units, at least 1% by weight of alkenecarboxylic ester and / or vinyl ester units, and 1 to 30% by weight of vinyl ketone -Units as well as minor amounts of customary further monomers copolymerizable with ethylene exist as flow improvers for crude oils and middle distillates of crude oil distillation
  • the ethylene copolymers used according to the invention are prepared by polymerizing the monomer mixture at temperatures from 100 to 350 ° C. and pressures from 1000 to 8000 bar in the presence of initiators which form free radicals. The polymerization does not require the presence of a solvent as the reaction medium. Solvent-free products are therefore obtained immediately.
  • waxy copolymers of ethylene which in addition to alkenecarboxylic acid ester units and / or vinyl ester units also contain vinyl ketone units, significantly improve the flowability of both middle distillates from crude oil distillation and crude oils themselves, compared to conventional products.
  • the improvement in flowability does not correspond to an additive effect of the content of ester and vinyl ketone units in the ethylene copolymers. Rather, it is shown that the action of the ester and vinyl ketone units increases synergistically.
  • the copolymers preferably contain 75 to 94% by weight of ethylene units, 5 to 15% by weight of alkenecarboxylic acid ester units and 1 to 10% by weight of vinyl ketone units.
  • esters of alkenecarboxylic acids having 3 to 12 carbon atoms with primary, secondary or tertiary alcohols containing 1 to 8 carbon atoms can be used as alkenecarboxylic acid esters. Examples are methyl acrylate, ethyl acrylate, butyl acrylate or 2-ethylhexyacrylate. Examples of vinyl esters are vinyl acetate, vinyl propionate; vinyl acetate is particularly suitable. Compounds such as vinyl methyl ketone, vinyl ethyl ketone, vinyl propyl ketone and preferably vinyl methyl ketone are suitable as vinyl ketones.
  • Typical copolymerizable with ethylene monomers which can be additionally contained in the copolymers are, for example C 3 - to C a alkenes, vinyl and Alkenyläther, vinyl and alkenyl alcohols, N-vinyl and N-alkenyl compounds such as N-vinylpyrrolidone , N-vinyl carbazole, N-vinyl caprolactam, acrylic and methacrylamides, acrylic and methacrylonitriles, vinyl and alkenyl ketones, vinyl and alkenyl sulfones and sulfonates, dicarbonates, acid anhydrides and styrene.
  • alkenes vinyl and Alkenyläther
  • vinyl and alkenyl alcohols vinyl and alkenyl alcohols
  • N-vinyl and N-alkenyl compounds such as N-vinylpyrrolidone , N-vinyl carbazole, N-vinyl caprolactam, acrylic and methacrylamide
  • the polymerization takes place in the presence of catalytic amounts of free radical initiators, e.g. Oxygen, in amounts of 2 to 250 mol ppm, based on the ethylene to be polymerized.
  • free radical initiators e.g. Oxygen
  • peroxides such as tert-butyl perbenzoate, dilauroyl peroxide, di-tert-butyl peroxide or azobutyronitrile in amounts of 2 to 200 mol ppm, based on the ethylene, can also be used as initiators.
  • the molecular weights are adjusted using moderators, such as aliphatic alcohols and / or carbonyl compounds, saturated, unsaturated or chlorinated hydrocarbons or hydrogen.
  • copolymers used according to the invention have molecular weights of 500 to 20,000, determined according to K. Rast, Ber. 550, 1922.
  • copolymers described above improve the flow properties of mineral oils, such as middle distillations of crude oil distillation and also of crude oil itself. Their effect is based on the fact that 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 and therefore Filters can pass.
  • These copolymers are normally added to the mineral oil in the form of about 40 to 50% 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.
  • the copolymers can be used alone or together with other pour point depressants or dewaxing aids, corrosion inhibitors, antioxidants or sludge inhibitors.
  • the copolymers are also suitable as adhesives, as coating materials and for mixing with waxes, the properties of which they improve.
  • a paraffin-rich middle distillate with a boiling point of 175 ° C, 5% point 195 ° C, 95% point 365 ° C, boiling point 383 ° C and a CFPP value of + 5 ° C is mixed with 200 ppm of an additive, which is 48% of a copolymer wax contains ethylene and 20% vinyl acetate with a viscosity (at 140 ° C) of 450 mPas.
  • the middle distillate treated in this way has a CFPP value of 0 ° C.
  • the middle distillate of Comparative Example A is mixed with a copolymer wax made of ethylene and 22% t-butyl acrylate, which has a viscosity (at 140 ° C) of 550 mPas, under otherwise constant conditions, the middle distillate treated in this way has a CFPP value of +1 ° C.
  • Comparative Example A If the middle distillate of Comparative Example A is mixed with a copolymer wax of ethylene and 10% methyl vinyl ketone, which has a viscosity (at 140 ° C.) of 500 mPas, under otherwise constant conditions, a CFPP value of +1 ° C. is measured.
  • a middle distillate with a boiling point of 178 ° C, 5% point of 201 ° C, 95% point of 359 ° C, boiling point of 376 ° C and CFPP of -4 ° C is mixed with 200 ppm of an additive that contains 48% of a copolymer wax from ethylene and 24 % Contains vinyl acetate with a viscosity (at 140 ° C) of 1600 mPas.
  • the middle distillate treated in this way has a CFPP value of -7 °.
  • the middle distillate of Comparative Example A is mixed with 200 ppm of an additive which contains 48% of a terpolymer wax made of ethylene, 19% vinyl acetate and 1% methyl vinyl ketone with a viscosity (at 140 ° C.) of 440 mPas.
  • the middle distillate treated in this way has a CFPP value of -3 ° C.
  • the middle distillate of Comparative Example A is mixed with 200 ppm of an additive which contains 48% of a terpolymer wax made of ethylene, 15% t-butyl acrylate and 3% methyl vinyl ketone with a viscosity (at 140 ° C.) of 600 mPas.
  • the middle distillate treated in this way has a CFPP value of -4 ° C.
  • the middle distillate of Comparative Example A is mixed with 200 ppm of an additive which contains 48% of a terpolymer wax made of ethylene, 15% vinyl acetate and 5% methyl vinyl ketone with a viscosity (at 140 ° C.) of 1480 mPas.
  • the middle distillate treated in this way has a CFPP value of -4 ° C.
  • the middle distillate of Comparative Example A is mixed with 200 ppm of an additive which contains 48% of a terpolymer wax made of ethylene, 5% vinyl acetate and 10% vinyl methyl ketone with a viscosity (at 140 ° C.) of 560 mPas.
  • the middle distillate treated in this way has a CFPP value of -6 ° C.
  • the middle distillate of Comparative Example D is mixed with 200 ppm of an additive which contains 48% of a terpolymer wax made of ethylene, 10% vinyl acetate and 10% methyl vinyl ketone with a viscosity (at 140 ° C.) of 1450 mPas.
  • the middle distillate treated in this way has a CFPP value of -14 ° C.

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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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Claims (7)

1. Utilisation de copolymères cireux d'un poids moléculaire de 500 à 20000, qui consistent en au moins 60% en poids de motifs éthylène, au moins 1 % en poids de motifs esters alcènecarboxyliques et/ou de motifs esters vinyliques et 1 à 30% en poids de motifs vinylcétones ainsi que de faibles quantités d'autres monomères habituels copoly- mérisables avec l'éthylene et qui sont préparés à partir des monomères susmentionnés à une pression comprise entre 1000 et 8000 bars et une température comprise entre 100 et 350°C en présence d'initiateurs de radicaux libres, comme agents améliorant la fluidité pour les huiles lourdes et les distillats moyens de la distillation des huiles lourdes.
2. Utilisation de copolymères cireux selon la revendication 1, caractérisée en ce qu'ils contiennent 74 à 94% en poids de motifs éthylène.
3. Utilisation de copolymères cireux selon la revendication 1 ou 2, caractérisée en ce qu'ils contiennent 5 à 15% en poids de motifs esters alcènecarboxyliques.
4. Utilisation de copolymères cireux selon les revendications 1 à 3, caractérisée en ce qu'ils contiennent 1 à 10% en poids de motifs vinylcétones.
5. Utilisation de copolymères cireux selon les revendications 1 à 4, caractérisée en ce qu'ils contiennent comme motif ester d'acide alcène- carboxylique des composés d'acides alcènecarboxyliques en C3-Cl2 et d'alcools primaires, secondaires ou tertiaires en C1-Ca.
6. Utilisation de copolymères cireux selon les revendications 1 à 5, caractérisée en ce qu'ils contiennent comme motif ester vinylique de l'acétate de vinyle.
7. Utilisation de copolymères cireux selon les revendications 1 à 6, caractérisée en ce qu'ils contiennent comme motif vinylcétone de la mé- thylvinylcétone.
EP83112556A 1982-12-23 1983-12-14 Utilisation de copolymères d'éthylène comme additifs pour les huiles minérales Expired EP0111883B2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83112556T ATE15064T1 (de) 1982-12-23 1983-12-14 Verwendung von ethylencopolymerisaten als mineraloeladditive.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19823247753 DE3247753A1 (de) 1982-12-23 1982-12-23 Verwendung von ethylencopolymerisaten als mineraloeladditive
DE3247753 1983-12-23

Publications (3)

Publication Number Publication Date
EP0111883A1 EP0111883A1 (fr) 1984-06-27
EP0111883B1 EP0111883B1 (fr) 1985-08-21
EP0111883B2 true EP0111883B2 (fr) 1988-10-26

Family

ID=6181593

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83112556A Expired EP0111883B2 (fr) 1982-12-23 1983-12-14 Utilisation de copolymères d'éthylène comme additifs pour les huiles minérales

Country Status (5)

Country Link
US (1) US4772673A (fr)
EP (1) EP0111883B2 (fr)
AT (1) ATE15064T1 (fr)
DE (2) DE3247753A1 (fr)
NO (1) NO163454C (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4020640A1 (de) * 1990-06-29 1992-01-02 Hoechst Ag Terpolymerisate des ethylens, ihre herstellung und ihre verwendung als additive fuer mineraloeldestillate
US6495495B1 (en) 1999-08-20 2002-12-17 The Lubrizol Corporation Filterability improver
DE10309571A1 (de) * 2003-03-05 2004-09-16 Basf Ag Brennstoffzusammensetzungen mit verbesserten Kaltfließeigenschaften
US20120302479A1 (en) 2009-12-07 2012-11-29 The Lubrizol Corporation Method of Lubricating a Manual Transmission
US12116474B2 (en) * 2019-01-28 2024-10-15 Japan Polyethylene Corporation Polar group-containing olefin copolymer

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3591502A (en) * 1968-07-15 1971-07-06 Exxon Research Engineering Co Copolymers containing ethylene and unsaturated ketones are wax crystal modifiers for mineral oil
GB1300227A (en) * 1969-05-09 1972-12-20 Exxon Research Engineering Co Flow improvers
US3853814A (en) * 1970-04-27 1974-12-10 J Guillet Photodegradable polymers of methyl methacrylate and unsaturated ketones
NL159413B (nl) * 1973-01-16 1979-02-15 Ruhrchemie Ag Werkwijze ter bereiding van afbreekbare tercopolymeren uit etheen, koolmonoxide en vinylacetaat.
DE2822436A1 (de) * 1978-05-23 1979-12-06 Consortium Elektrochem Ind Hydroxylgruppen enthaltende vinylester- und vinylhalogenid-copolymere
US4230843A (en) * 1979-02-02 1980-10-28 The Lubrizol Corporation Polymeric compositions, method for their preparation, and lubricants containing them

Also Published As

Publication number Publication date
EP0111883A1 (fr) 1984-06-27
NO834647L (no) 1984-06-25
NO163454B (no) 1990-02-19
EP0111883B1 (fr) 1985-08-21
DE3360622D1 (en) 1985-09-26
ATE15064T1 (de) 1985-09-15
US4772673A (en) 1988-09-20
NO163454C (no) 1990-05-30
DE3247753A1 (de) 1984-06-28

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