EP0857776A1 - Amélioration de la fluidité d'huiles minérales et de distillates d'huiles minérales par l'utilisation de résines alkylphénol-aldéhyde - Google Patents

Amélioration de la fluidité d'huiles minérales et de distillates d'huiles minérales par l'utilisation de résines alkylphénol-aldéhyde Download PDF

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Publication number
EP0857776A1
EP0857776A1 EP97122900A EP97122900A EP0857776A1 EP 0857776 A1 EP0857776 A1 EP 0857776A1 EP 97122900 A EP97122900 A EP 97122900A EP 97122900 A EP97122900 A EP 97122900A EP 0857776 A1 EP0857776 A1 EP 0857776A1
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EP
European Patent Office
Prior art keywords
mineral oil
alkylphenol
paraffin
ppm
ethylene
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.)
Granted
Application number
EP97122900A
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German (de)
English (en)
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EP0857776B1 (fr
EP0857776B2 (fr
Inventor
Matthias Dr. Krull
Michael Dr. Feustel
Werner Dr. Reimann
Ulrike Tepper
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Clariant Produkte Deutschland GmbH
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Clariant GmbH
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Priority claimed from DE1997100159 external-priority patent/DE19700159A1/de
Priority claimed from DE1997139272 external-priority patent/DE19739272A1/de
Application filed by Clariant GmbH filed Critical Clariant GmbH
Publication of EP0857776A1 publication Critical patent/EP0857776A1/fr
Publication of EP0857776B1 publication Critical patent/EP0857776B1/fr
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    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
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    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
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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 invention relates to a method for improving the flowability of mineral oils and mineral oil distillates containing paraffin by adding Flow improvers based on ethylene-vinyl ester copolymers and terpolymers, Alkylphenol aldehyde resins and optionally other paraffin dispersants.
  • Crude oils and middle distillates obtained by distilling crude oils such as gas oil, Diesel oil or heating oil contain different ones depending on the origin of the crude oils Amounts of n-paraffins, which as a platelet when the temperature is lowered Crystallize crystals and partially agglomerate with the inclusion of oil This crystallization and agglomeration leads to a deterioration the flow properties of the oils or distillates, which means that during extraction, transport, Storage and / or use of mineral oils and mineral oil distillates may occur. This can happen when transporting mineral oils through pipes Crystallization phenomenon, especially in winter, to deposits on the Pipe walls, in individual cases, e.g. if a pipeline is at a standstill, even to it cause complete constipation.
  • the mineral oils When storing and processing the Mineral oils may also be required in winter, the mineral oils in heated To store tanks. With mineral oil distillates, it occurs as a result of crystallization if necessary, clogging of the filters in diesel engines and Firing systems, which prevents safe metering of the fuels and possibly complete interruption of fuel or Heating medium supply occurs.
  • Typical flow improvers for crude oils and middle distillates are copolymers and terpolymers of ethylene with carboxylic acid esters of vinyl alcohol.
  • Another task of flow improver additives is to disperse the Paraffin crystals, i.e. the delay or prevention of sedimentation of the Paraffin crystals and thus the formation of a paraffin-rich layer on the bottom of Storage containers.
  • the monomeric paraffin dispersants are, for example, from EP-A-0 413 279 Reaction products of alkenyl spirobis lactones with amines are known.
  • EP-A-0 061 894 are also oil-soluble nitrogen-containing compounds such as e.g. Reaction products of phthalic anhydride with amines described in Mixture with ethylene-vinyl acetate copolymers can be used.
  • EP-A-0 688 796 discloses copolymers based on ⁇ , ⁇ -unsaturated Olefins with at least 3 carbon atoms and ⁇ , ⁇ -unsaturated Dicarboxylic anhydrides are known, the dicarboxylic anhydride units by polymer-analogous reaction with polyetheramines or alkanolamines in Imide, amide or ammonium units are transferred.
  • EP-A-0 606 055 discloses terpolymers based on ⁇ , ⁇ -unsaturated Dicarboxylic acid anhydrides, ⁇ , ⁇ -unsaturated compounds and Polyoxyalkylene ethers of lower, unsaturated alcohols, and their Use as paraffin inhibitors for petroleum products containing paraffin.
  • EP-A-0 154 177 describes reaction products of alternating copolymers based on maleic anhydride and ⁇ , ⁇ -unsaturated compounds primary monoalkylamines and aliphatic alcohols described. This Copolymers are particularly useful as paraffin inhibitors for those containing paraffin Petroleum products, such as crude oils and distillation residues from Petroleum processing, suitable.
  • EP-A-0 436 151 describes reaction products of copolymers based on Maleic anhydride and ⁇ , ⁇ -unsaturated compounds with dialkylamines known.
  • EP-A-0 283 293 discloses copolymers based on aliphatic olefins and Maleic anhydride, the copolymer having both ester and amide groups must have, each of which has an alkyl group with at least 10 Contains carbon atoms, and copolymers obtained by reacting one secondary amine with a polymer containing anhydride groups, from which Anhydride groups in equal parts of amides or ammonium salts are formed.
  • paraffin dispersants are usually used with others Flow improvers, in particular ethylene-vinyl ester copolymers, are used.
  • emulsion splitters have the ability to take an oil / water emulsion Break formation of separate oil and water phases. You must therefore both Hydrophobic as well as hydrophilic structural units contain, on the one hand Side to dissolve sufficiently in the oil of the oil / water emulsion to the latter split, and on the other hand after the phase separation in the to enrich the aqueous phase.
  • emulsion splitter with a flow-improving / paraffin-inhibiting effect suitable according to WO93 / 14178 alkoxylated alkylphenol formaldehyde resins.
  • oxalkyl side chain which represents the hydrophilic structural part, up to 50 Oxalkyl units, each having 2 - 6 carbon atoms.
  • EP-A-0 311 452 discloses condensation products of at least 80 mol% difunctional, alkylated phenol and aldehydes containing 1 to 30 carbon atoms include, as a flow improver for mineral oils.
  • the use of Condensation products of monoalkylated phenols with aldehydes as Flow improvers or paraffin dispersants are not disclosed.
  • paraffin-dispersing action of the known paraffin dispersants is not always sufficient, so that when the oils cool down partially form large wax crystals, which due to their higher density in the course sediment the time and thus to form a paraffin-rich layer on Lead the bottom of storage containers.
  • Problems occur especially with the additives of paraffin-rich narrow distillation cuts with boiling ranges from 20-90 Vol% less than 110 ° C, especially less than 100 ° C. Even with distillates with one more than 20 ° C, in particular more than 25 ° C large temperature difference between The boiling point and the temperature at which 90% by volume are distilled can be determined by the Addition of known additives often does not provide sufficient paraffin dispersion achieve.
  • alkylphenol-aldehyde resins themselves have a paraffin-dispersing effect, excellent solubilizers between these substances.
  • the alkylphenols are preferably para-substituted. They are preferably too at most 7 mol%, in particular at most 3 mol% with more than one Alkyl group substituted.
  • the additives A, B and optionally C can be the paraffinic Mineral oils or mineral oil distillates are added separately.
  • the individual additives or corresponding mixtures before addition to the mineral oils or Mineral oil distillates dissolved in an organic solvent or dispersant or dispersed.
  • the solution or dispersion contains 5-90, preferably 5-75% by weight of the respective mixture.
  • Suitable solvents or dispersants are aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures, e.g. Gasoline fractions, kerosene, decane, pentadecane, toluene, xylene, ethylbenzene or commercial solvent mixtures such as ®Solvent Naphtha, ®Shellsol AB, ®Solvesso 150, ®Solvesso 200, ®Exxsol, ®ISOPAR and Shellsol D types.
  • polar solubilizers such as 2-ethylhexanol, Decanol, iso-decanol or iso-tridecanol can be added.
  • the mineral oils or mineral oil distillates can also be other common Additives such as dewaxing agents, corrosion inhibitors, Antioxidants, lubricity additives, sludge inhibitors, cetane number improvers, Detergent additives, dehazers, conductivity improvers or dyes.
  • Additives such as dewaxing agents, corrosion inhibitors, Antioxidants, lubricity additives, sludge inhibitors, cetane number improvers, Detergent additives, dehazers, conductivity improvers or dyes.
  • Another object of the invention is an additive mixture for Paraffin dispersion in mineral oils and mineral oil distillates containing paraffin, containing at least one paraffin dispersant and at least one aliphatic or aromatic, liquid hydrocarbon as solvent, characterized in that at least one alkylphenol-aldehyde resin as Solubilizer is added.
  • Another object of the invention is a method for producing Solutions of paraffin dispersants in aliphatic or aromatic liquid Hydrocarbons by adding an alkylphenol-aldehyde resin to the mixture of these substances adds.
  • Alkylphenol-aldehyde resins B are known in principle and, for example, in Römpp Chemistry lexicon, 9th edition, Thieme Verlag 1988-92, Volume 4, pp. 3351ff. described.
  • the alkyl radicals of the o- or p-alkylphenol have 1-20, preferably 4-16, especially 6-12 carbon atoms; it is preferably n-, iso- and tert. Butyl, n- and iso-pentyl, n- and iso-hexyl, n- and iso-octyl, n- and iso-nonyl, n-and iso-decyl, n- and iso-dodecyl.
  • the alkylphenol aldehyde can also contain up to 50 mol% Contain phenol units.
  • the same or different alkylphenols can be used.
  • the aliphatic aldehyde in Alkylphenol aldehyde resin B has 1-4 carbon atoms and is preferred Formaldehyde.
  • the molecular weight of the alkylphenol-aldehyde resins is 400 - 10,000, preferably 400 - 5000 g / mol. The prerequisite here is that the resins are oil-soluble.
  • the alkylphenol-aldehyde resins B are prepared in a known manner by basic catalysis, whereby condensation products of the resol type arise, or by acidic catalysis, producing condensation products of the novolak type.
  • the condensates obtained in both ways are as additives B in method according to the invention suitable.
  • the condensation is preferred in Presence of acidic catalysts.
  • Suitable alkylphenols are in particular C 4 -C 12 alkylphenols such as o- or p-cresol, n-, sec. - and tert. Butylphenol, n- and i-pentylphenol, n- and iso-hexylphenol, n- and iso-octylphenol, n- and iso-nonylphenol, n- and iso-decylphenol, n- and iso-dodecylphenol
  • the alkylphenols to be used can be small amounts, preferably up to about 10 mol%, in particular up to 7 mol% and especially up to 3 mol% Contain dialkylphenols.
  • aldehydes are formaldehyde, acetaldehyde and butyraldehyde, formaldehyde is preferred.
  • the formaldehyde can be in the form of paraformaldehyde or in the form of a preferably 20-40 wt .-% aqueous formalin solution can be used. It appropriate amounts of trioxane can also be used.
  • alkylphenol and aldehyde usually takes place in the presence of alkaline catalysts, for example alkali hydroxides or alkylamines, or of acidic catalysts, for example inorganic or organic Acids, such as hydrochloric acid, sulfuric acid, phosphoric acid, sulfonic acid, Sulfamido acids or haloacetic acids, and in the presence of one with water Azeotropic organic solvent, for example toluene, xylene, higher aromatics or mixtures thereof.
  • the reaction mixture is on a Temperature of 90 to 200 ° C, preferably 100-160 ° C heated, which water of reaction formed during the reaction by azeotropic distillation Will get removed.
  • the resins can be used directly or after neutralization of the catalyst are used, if necessary after further dilution of the solution with aliphatic and / or aromatic hydrocarbons or Hydrocarbon mixtures, e.g. Gasoline fractions, kerosene, decane, pentadecane, Toluene, xylene, ethylbenzene or solvents such as ®Solvent Naphtha, ®Shellsol AB, ®Solvesso 150, ®Solvesso 200, ®Exxsol, ®ISOPAR and Shellsol D types.
  • aliphatic and / or aromatic hydrocarbons or Hydrocarbon mixtures e.g. Gasoline fractions, kerosene, decane, pentadecane, Toluene, xylene, ethylbenzene or solvents such as ®Solvent Na
  • Such ethylene-vinyl ester copolymers or terpolymers having a Ethylene content of 60-90% by weight Such ethylene-vinyl ester copolymers or terpolymers having a Ethylene content of 60-90% by weight.
  • the polar ones are preferred nitrogenous compounds.
  • monomeric polar nitrogen-containing compounds C for example following substances are used.
  • EP-A-0 413 279 describes suitable reaction products of Alkenylspirobislactones with amines are described.
  • the oil-soluble reaction products of EP-A-0 061 894 Phthalic anhydride with amines can be mixed with ethylene-vinyl acetate copolymers be used.
  • reaction products known from EP-A-0 597 278 of Aminoalkylene carboxylic acids with primary or secondary amines as monomers nitrogenous compounds C are also known from EP-A-0 597 278 of Aminoalkylene carboxylic acids with primary or secondary amines as monomers nitrogenous compounds C.
  • Additive A can also Mixtures of different ethylene vinyl ester copolymers or terpolymers are used which have a different qualitative and / or quantitative Composition and / or different viscosities (measured at 140 ° C) exhibit.
  • Mixtures of alkylphenol-aldehyde resins are also additive B. usable as the various alkylphenols and / or aldehydes Components included.
  • Mixtures of several of B various paraffin dispersants C can be used. Leave this way the flow improvers adapt to individual requirements.
  • Mineral oils and mineral oil distillates containing paraffin are within the meaning of the invention for example crude oils, distillation residues from petroleum processing or others paraffinic oils. (compare e.g. Compositions and Properties of Petroleum, F. Enke Publishers, Stuttgart 1981, pages 1 - 37). Mineral oil products containing paraffin, in particular middle distillates such as jet fuel, diesel, heating oil EL and heavy heating oil is due to a boiling range of 120 - 500 ° C, preferably 150 - 400 ° C characterized.
  • the paraffins are straight-chain or branched alkanes with about 10 - 50 carbon atoms.
  • the cold flow behavior was determined as follows:
  • test oils were measured at room temperature using the ones in Table 2 specified amounts of the additives tempered at 60 ° C, 15 minutes heated to 40 ° C with occasional shaking and then on Cooled to room temperature.
  • the middle distillate so additized was according to EN 116 determines the CFPP value (Cold Filter Plugging Point).
  • the paraffin dispersion in middle distillates was as follows in the short sediment test proven:
  • Representative winter diesel fuels were selected for the following tests German refineries.
  • the middle distillates were at room temperature mixed with the stated amounts of the additives heated to 60 ° C., 15 Minunten heated to 40 ° C with occasional shaking and then on Cooled to room temperature.
  • the middle distillate so additized was according to EN 116 determines the CFPP value.
  • the additive middle distillates were in 200 ml measuring cylinders in one Refrigerator cooled to -2 ° C / hour to -13 ° C and 16 hours at this Temperature stored. Subsequently, both volume and appearance were visual the sediment (paraffin phase) as well as the oil phase above it and judged. A small amount of sediment and a cloudy oil phase show one good paraffin dispersion.

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  • Organic Chemistry (AREA)
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EP97122900A 1997-01-07 1997-12-24 Amélioration de la fluidité d'huiles minérales et de distillates d'huiles minérales par l'utilisation de résines alkylphénol-aldéhyde Expired - Lifetime EP0857776B2 (fr)

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DE19700159 1997-01-07
DE1997100159 DE19700159A1 (de) 1997-01-07 1997-01-07 Verbesserung der Fließfähigkeit von Mineralölen und Mineralöldestillaten unter Verwendung von Alkylphenol-Aldehydharzen
DE19739272 1997-09-08
DE1997139272 DE19739272A1 (de) 1997-09-08 1997-09-08 Additiv zur Paraffindispergierung in Mineralölen und Mineralöldestillaten

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ES2183073T3 (es) 2003-03-16
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ES2183073T5 (es) 2007-10-16
JPH10245575A (ja) 1998-09-14
NO980064L (no) 1998-07-08
KR19980070366A (ko) 1998-10-26
DE59708189D1 (de) 2002-10-17
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US5998530A (en) 1999-12-07
JP4132167B2 (ja) 2008-08-13

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