EP0654526A2 - Trübungspunkterniedrigende Zusammensetzung - Google Patents

Trübungspunkterniedrigende Zusammensetzung Download PDF

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Publication number
EP0654526A2
EP0654526A2 EP94308217A EP94308217A EP0654526A2 EP 0654526 A2 EP0654526 A2 EP 0654526A2 EP 94308217 A EP94308217 A EP 94308217A EP 94308217 A EP94308217 A EP 94308217A EP 0654526 A2 EP0654526 A2 EP 0654526A2
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Prior art keywords
carbon atoms
composition
hydrocarbyl
alkyl
polymer
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EP94308217A
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English (en)
French (fr)
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EP0654526A3 (de
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Gregory Lee Hiebert
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Lubrizol Corp
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Lubrizol Corp
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Publication of EP0654526A3 publication Critical patent/EP0654526A3/de
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    • 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
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Definitions

  • the dewaxing aid is a mixture of poly di-alkyl fumarate/vinyl acetate copolymers and a wax-naphthalene condensate.
  • the condensate has a molecular weight of about 1,000 and greater.
  • the present invention provides a composition
  • a composition comprising (a) a polymer of (i) a hydrocarbyl ester of an ethylenically unsaturated acid of 3 to 6 carbon atoms, wherein the hydrocarbyl group contains about 8 to about 40 carbon atoms, (ii) an ester-containing monomer selected from the group consisting of alkyl esters of ethylenically unsaturated acids of 3 to 6 carbon atoms wherein the alkyl group contains fewer than 8 carbon atoms and vinyl alkanoates wherein the alkanoate group contains up to about 8 carbon atoms, and (iii) an alkyl ether monomer wherein the alkyl group contains up to about 8 carbon atoms; and (b) a polynuclear aromatic material, substituted on at least one ring with at least one hydrocarbyl group having about 8 to about 20 carbon atoms and with at least one hydrocarbyl group having about 21 to about 40 carbon atoms, wherein the amounts
  • the invention further provides a method for reducing the cloud point of a paraffinic liquid, comprising adding thereto an effective amount of such compositions; and further such compositions such additives in paraffinic liquids.
  • stereochemistry of the resulting polymer may in some cases differ depending on whether maleic (cis) or fumaric (trans) monomer is used. In some instances it may be more convenient to use one material rather than the other; maleic acid, for example, can form a cyclic anhydride which can be polymerized as such, while fumaric acid cannot.
  • references herein to polymers of fumaric acid or fumaric esters are intended to include polymers similarly derived from maleic acid, maleic anhydride, or maleic esters.
  • the alcohol with which the acid monomer or the polymeric acid functionality is reacted to form the ester is an alcohol with a hydrocarbyl chain containing 8 to 40 carbon atoms, more preferably 10 to 28 carbon atoms, and most preferably 12 to 14 carbon atoms.
  • the hydrocarbyl group need not be derived from a single alcohol of a single chain length, however, but can be derived from a mixture of alcohols if desired, provided that at least some of the chain lengths of the alcohol portion are within the desired range.
  • the specific chain length of the hydrocarbyl groups can be selected to correspond to the type of paraffinic fluid in which the polymer is employed, as described in more detail below.
  • the polymer of component (a) may also contain other copolymerizable monomers such as the ⁇ -olefins, including ethylene, propylene, or styrene, as well as carbon monoxide or sulfur dioxide.
  • the amount of these and other supplemental comonomers, if any, is preferably sufficiently low that the polymer substantially retains its character as a hydrocarbyl alkenoate polymer, modified by the presence of the above-defined comonomers.
  • the reaction time will vary from 1 to 30 hours depending on the temperature, reactivity of the monomers, and other reaction conditions.
  • the polymerization can be run continuously or batchwise. Details of such polymerizations are well known to those skilled in the art and are reported in greater detail in U.S. Patent 3,250,715.
  • the second important component (b) of the present invention is a compound with fused aromatic rings, that is, polynuclear aromatic compounds in which the aromatic rings share at least one side.
  • the polynuclear aromatic compound is substituted on at least one such ring with at least one hydrocarbyl group having chain length defined below.
  • Typical fused ring aromatic systems include naphthalene, with two rings, anthracene and phenanthrene, with three rings, and naphthacene, chrysene, triphenylene, and pyrene with four rings. Naphthalene is the preferred fused ring aromatic hydrocarbon.
  • the substitution of the material of component (b) comprises a fraction of relatively shorter chain hydrocarbyl groups, containing 8 to 20 carbon atoms, and a second fraction of relatively longer chain hydrocarbyl (or hydrocarbylene) groups, containing 21 to 40 carbon atoms.
  • the longer chain groups are preferably derived from chlorinated hydrocarbons or are materials of similar structure although derived from precursors other than chlorinated hydrocarbons.
  • Chlorinated hydrocarbons typically contain at least a fraction of molecules which are polychlorinated, which fraction can result in hydrocarbylene substitution on the aromatic molecules, that is, formation of hydrocarbylene linkages among aromatic nuclei. (As used herein, the term "hydrocarbyl" is to be construed to include hydrocarbylene).
  • hydrocarbylene linkages increases the effective molecular weight of the molecules.
  • the polyfunctional reactants which lead to hydrocarbylene groups and the linkage of aromatic moieties preferably contain at least about 14 carbon atoms, and more preferably at least about 22 carbon atoms. That is, preferably the polyfunctional reactants constitute the longer chain fraction of the hydrocarbyl substituents.
  • the hydrocarbyl group or groups are preferably alkyl (or alkylene) groups.
  • Alkyl or alkylene groups can be attached to an aromatic ring by any of a variety of methods, the commonest being known as the Friedel-Crafts reaction.
  • a chlorinated alkane or a chlorinated wax for example, can be condensed with the aromatic ring in the presence of an appropriate amount of inert solvent, using a small amount of a catalyst such as aluminum chloride.
  • a chlorinated material with a single chlorine atom will provide an alkyl chain; a material with multiple chlorine atoms will provide alkylene substitution and linkage of multiple aromatic rings into an oligomeric or polymeric structure.
  • the starting material can be an olefin which is reacted with aluminum chloride in situ.
  • the reaction can be started at room temperature and, after the catalyst and reactants have all been mixed, the reaction mixture can be heated to a final temperature of 30 to 100°C. After the reaction has been completed (generally requiring 1/2 hour to 10 hours) residual catalyst can be hydrolyzed by adding water and base and the catalyst removed by an appropriate method such as filtration or washing with water. The product can be purified if desired by known methods, although this may not be necessary.
  • Such bridged materials may be considered polymeric materials, the term being interpreted broadly to include oligomeric materials containing e.g. 2 or 3 or several aromatic groups as well as structures with higher molecular weights. Such materials are included within the definition of hydrocarbyl-substituted aromatic compounds, and in such cases the hydrocarbyl substituents are to be construed to contain the number of carbon atoms contained in the chlorinated alkane, that is, discounting the effects of the polymerization.
  • components (a) and (b) are such that the combination, when added to a paraffinic liquid, provides a reduction in the cloud point of the liquid. In practice is has been found preferable in some cases to use a modest excess of the hydrocarbyl-substituted aromatic compound.
  • components (a) and (b) are used in relative amounts of 90:10 to 5:95 by weight; preferably the relative amounts of components (a) and (b) are 80:20 to 10:90, and most preferably the relative amounts are 50:50 to 20:80.
  • Components (a) and (b) can be combined by any convenient means, or they can be added separately to a paraffinic liquid. Combining of the components can be effected by blending at ambient temperatures with moderate mixing for 10 minutes to 2 hours, typically about 30 minutes. Gentle heating, to e.g. 50-80°C (preferably about 65°C) often improves the ease of mixing.
  • Paraffinic liquids include refined and unrefined petroleum, including condensate crude oils (oils obtained from gas wells, comprising predominantly low molecular weight materials with a high molecular weight fraction).
  • Crude petroleum contains a wide variety of components, in particular alkanes having up to about 28 carbon atoms and above.
  • the fractions derived from crude oil by distillation are middle distillates, loosely characterized by normal boiling points of 177-454°C (350-850°F), and diesel fuels, loosely characterized by normal boiling points of 177-343°C (350-650°F). These boiling points correspond roughly to those of alkanes in the C12 to C18 range for middle distillates and the C12 to C16 range for diesel fuels.
  • the present invention is also applicable to lighter distillation cuts including gasoline or naphtha, as well as to synthetic oils which have a paraffinic component.
  • Such synthetic oils include those made by polymerization of olefins or other unsaturated aliphatic olefins.
  • the invention is applicable to paraffinic liquids which can be used as lubricants, as fuels, as functional fluids (including hydraulic fluids), or for any other use.
  • the chain lengths of the substituents of components (a) and (b) are preferably selected to correspond, at least approximately, to the length of the carbon chains in the paraffinic liquid. That is, when the composition is used as a cloud point depressant in a diesel fuel, the hydrocarbyl or alkyl groups in the alcoholic-derived moiety of the ester group preferably contain 10 to 16, and more preferably 12 to 14 carbon atoms. When the composition is used in other middle range distillates, the alcohol-derived moieties can preferably contain 12 to 20, and more preferably 14 to 18 carbon atoms. For higher boiling fractions, the alcohol-derived moieties can contain 18 to 28 carbon atoms.
  • the hydrocarbyl or alkyl groups on the polynuclear aromatic material can be similarly selected. Suitable selection of hydrocarbyl chain length provides optimum solubility and compatibility properties.
  • the amount of the total additive composition (a) plus (b) is an amount sufficient to cause a reduction of the cloud point of the paraffinic liquid to which it is added. Often this amount is 50 to 2000 parts per million, preferably 100 to 600 parts per million (i.e. 0.01 to 0.6 percent by weight of the composition).
  • EVA copolymers are well known materials, typically made by free-radial polymerization of vinyl acetate and ethylene, optionally with other comonomers.
  • Preferred materials for use in the present invention are binary copolymers which contain 15 to 40 weight percent, and more preferably 33 to 38 weight percent copolymerized vinyl acetate.
  • the number average molecular weight of the supplemental polymeric pour point depressant is not particularly critical but for EVA copolymers is preferably 1000 to 10,000, more preferably 1500 to 2600.
  • compositions are prepared of a standard diesel fuel (AmocoTM Whiting base fuel) containing various amounts of the composition of the present invention and, for comparison, no additive.
  • the additive representative of the present invention is a mixture of a C12 ⁇ 14 fumarate/vinyl acetate/ethyl vinyl ether copolymer (5.5% vinyl acetate moiety content and 3.1% ethyl vinyl ether content, by weight, weight average molecular weight about 20,000) and an alkylated naphthalene, in the parts by weight indicated.
  • Examples 11-28 Examples 1-10 are substantially repeated in a diesel fuel from Star Enterprise. The concentrations and results are shown in Table II: TABLE II Ex. Fumarate copolymer ppm alkylated naphthalene, ppm Cloud point, °C 11 0 0 -6 12 630 1000 -9 13 630 1000 -9 14 756 1000 -9 15 882 1000 -9 16 1008 1000 -9 17 630 800 -9 18 630 600 -9 19 194 192 -6 20 388 385 -9 21 582 577 -6 22 776 769 -9 23 970 962 -9 24 1164 1154 -9 25 1552 1538 -9 26 1940 1923 -9 27 252 600 -9 28 126 300 -9
  • Example 29 The above procedure is repeated in a diesel fuel designated DDR-490, which has a cloud point of -6°C.
  • DDR-490 diesel fuel designated DDR-490
  • Addition of 386 to 773 ppm of the additive combination of Example 8 reduces the cloud point to -9°C.
  • Addition of 213 to 639 ppm of the additive combination of Example 2 does not lead to a measurable change in cloud point at a measurement interval of 3C°. More precise measurements, made using an interval of less than 3C° or using a differential scanning calorimetry method, will detect the reduction in cloud point.
  • Example 34 Example 33 is repeated except that the alkylated naphthalene is replaced in turn by a corresponding amount of the following materials:

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
EP94308217A 1993-11-09 1994-11-08 Trübungspunkterniedrigende Zusammensetzung. Withdrawn EP0654526A3 (de)

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US149589 1993-11-09

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6203583B1 (en) 1999-05-13 2001-03-20 Equistar Chemicals, Lp Cold flow improvers for distillate fuel compositions
US6206939B1 (en) 1999-05-13 2001-03-27 Equistar Chemicals, Lp Wax anti-settling agents for distillate fuels
US6342081B1 (en) 1999-07-13 2002-01-29 Equistar Chemicals, Lp Cloud point depressants for middle distillate fuels
US6673131B2 (en) 2002-01-17 2004-01-06 Equistar Chemicals, Lp Fuel additive compositions and distillate fuels containing same
WO2024115211A1 (en) * 2022-11-30 2024-06-06 Basf Se Homo- and copolymers of vinyl ethers for reducing crystallization of paraffin crystals in fuels

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3250715A (en) * 1964-02-04 1966-05-10 Lubrizol Corp Terpolymer product and lubricating composition containing it
US3961915A (en) * 1974-12-27 1976-06-08 Exxon Research And Engineering Company Synergistic additive in petroleum middle distillate fuel
US4088589A (en) * 1976-05-20 1978-05-09 Exxon Research & Engineering Co. Dual pour depressant combination for viscosity index improved waxy multigrade lubricants
US4255159A (en) * 1980-02-11 1981-03-10 Exxon Research & Engineering Co. Polymer combinations useful in fuel oil to improve cold flow properties
FR2566288B1 (fr) * 1984-06-21 1991-10-18 Elf Aquitaine Additifs polymeriques utilisables pour l'inhibition du depot de paraffines dans les huiles brutes
US4753745A (en) * 1985-12-30 1988-06-28 The Lubrizol Corporation Methylene linked aromatic pour point depressant
GB8820071D0 (en) * 1988-08-24 1988-09-28 Exxon Chemical Patents Inc Fuel compositions
GB9205996D0 (en) * 1992-03-19 1992-04-29 Exxon Chemical Patents Inc Polymers and additive compositions
GB9301752D0 (en) * 1993-01-29 1993-03-17 Exxon Chemical Patents Inc Oil and fuel oil compositions

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6203583B1 (en) 1999-05-13 2001-03-20 Equistar Chemicals, Lp Cold flow improvers for distillate fuel compositions
US6206939B1 (en) 1999-05-13 2001-03-27 Equistar Chemicals, Lp Wax anti-settling agents for distillate fuels
US6342081B1 (en) 1999-07-13 2002-01-29 Equistar Chemicals, Lp Cloud point depressants for middle distillate fuels
US6673131B2 (en) 2002-01-17 2004-01-06 Equistar Chemicals, Lp Fuel additive compositions and distillate fuels containing same
WO2024115211A1 (en) * 2022-11-30 2024-06-06 Basf Se Homo- and copolymers of vinyl ethers for reducing crystallization of paraffin crystals in fuels

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FI945203A7 (fi) 1995-05-10
EP0654526A3 (de) 1996-03-27
FI945203A0 (fi) 1994-11-04
FI945203L (fi) 1995-05-10
NO944198D0 (no) 1994-11-03
CA2135136A1 (en) 1995-05-10
JPH07188501A (ja) 1995-07-25
NO944198L (no) 1995-05-10

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