EP0857776B2 - Verbesserung der Fliessfähigkeit von Mineralölen und Mineralöldestillaten unter Verwendung von Alkylphenol-Aldehydharzen - Google Patents

Verbesserung der Fliessfähigkeit von Mineralölen und Mineralöldestillaten unter Verwendung von Alkylphenol-Aldehydharzen Download PDF

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Publication number
EP0857776B2
EP0857776B2 EP97122900A EP97122900A EP0857776B2 EP 0857776 B2 EP0857776 B2 EP 0857776B2 EP 97122900 A EP97122900 A EP 97122900A EP 97122900 A EP97122900 A EP 97122900A EP 0857776 B2 EP0857776 B2 EP 0857776B2
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EP
European Patent Office
Prior art keywords
mineral oil
alkylphenol
aldehyde
weight
ppm
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
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EP97122900A
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German (de)
English (en)
French (fr)
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EP0857776A1 (de
EP0857776B1 (de
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 Produkte Deutschland 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 Produkte Deutschland GmbH filed Critical Clariant Produkte Deutschland GmbH
Publication of EP0857776A1 publication Critical patent/EP0857776A1/de
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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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    • C10L1/196—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
    • C10L1/1966—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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    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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Definitions

  • the invention relates to a process for improving the flowability of paraffin-containing mineral oils and mineral oil distillates by adding flow improvers based on ethylene-vinyl ester copolymers and terpolymers, alkylphenol-aldehyde resins and optionally further paraffin dispersants.
  • crude oils and middle distillates obtained by distillation of crude oils such as gas oil, diesel oil or fuel oil
  • crude oils and middle distillates obtained by distillation of crude oils contain different amounts of n-paraffins which crystallize out as platelet-shaped crystals when the temperature is lowered and partly agglomerate with the inclusion of oil.
  • the flow properties of the oils or distillates deteriorate, which can lead to disruptions in the extraction, transport, storage and / or use of the mineral oils and mineral oil distillates.
  • the phenomenon of crystallization especially in winter, can lead to deposits on the pipe walls, in individual cases, e.g. at standstill of a pipeline, even lead to their complete blockage.
  • Typical flow improvers for crude oils and middle distillates are copolymers and terpolymers of ethylene with carboxylic acid esters of vinyl alcohol.
  • Another object of flow improver additives is the dispersion of paraffin crystals, i. the delay or prevention of the sedimentation of paraffin crystals and thus the formation of a paraffin-rich layer at the bottom of storage containers.
  • Examples of monomeric paraffin dispersants which are known from EP-A-0 413 279 are reaction products of alkenyl spiro-bis-lactones with amines.
  • EP-A-0 061 894 discloses oil-soluble nitrogen-containing compounds, e.g. Reaction products of phthalic anhydride with amines described, which are used in admixture with ethylene-vinyl acetate copolymers.
  • reaction products of aminoalkylenecarboxylic acids with primary or secondary amines are known.
  • polymeric paraffin dispersants for example, the following are described in the literature.
  • EP-A-0 688 796 discloses copolymers based on ⁇ , ⁇ -unsaturated olefins having at least 3 C atoms and ⁇ , ⁇ -unsaturated dicarboxylic acid anhydrides, the dicarboxylic anhydride units being prepared 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 paraffinic petroleum products.
  • EP-A-0 154 177 describes reaction products of alternating copolymers based on maleic anhydride and ⁇ , ⁇ -unsaturated compounds with primary monoalkylamines and aliphatic alcohols. These copolymers are particularly useful as paraffin inhibitors of paraffinic petroleum products, for example, crude oils and distillation residues from petroleum processing.
  • EP-A-0 436 151 discloses reaction products of copolymers based on maleic anhydride and ⁇ , ⁇ -unsaturated compounds with dialkylamines.
  • EP-A-0 283 293 discloses copolymers based on aliphatic olefins and maleic anhydride, which copolymer must have both ester and amide groups, each containing an alkyl group of at least 10 carbon atoms, and copolymers obtained by reacting a secondary amine with a polymer containing anhydride groups, wherein the anhydride groups in equal parts amides or ammonium salts.
  • paraffin dispersants are usually used together with other flow improvers, in particular ethylene-vinyl ester copolymers.
  • emulsion breakers have the ability to break an oil / water emulsion to form separate oil and water phases. They must therefore contain both hydrophobic and hydrophilic structural units in order to dissolve sufficiently in the oil of the oil / water emulsion on the one hand, in order to split the latter, and on the other hand to enrich after the phase separation in the aqueous phase.
  • oxalkylated alkylphenol-formaldehyde resins are suitable.
  • the oxalkyl side chain representing the hydrophilic structural portion contains up to 50 oxalkyl units, each having 2-6 C atoms.
  • EP-A-0 311 452 discloses condensation products of at least 80 mole% of difunctional, alkylated phenol and aldehydes comprising from 1 to 30 carbon atoms as flow improvers for mineral oils.
  • the use of condensation products of monoalkylated phenols with aldehydes as flow improvers or paraffin dispersants is not disclosed.
  • paraffin-dispersing effect of the known paraffin dispersants described above is not always sufficient, so that on cooling the oils sometimes form large paraffin crystals, which sediment over time due to their higher density and thus lead to the formation of a paraffin-rich layer at the bottom of Lager organizationsem , Problems occur especially in the addition of paraffin-rich narrow distillation cuts with boiling ranges of 20-90% by volume less than 110 ° C, especially less than 100 ° C. Even with distillates with more than 20 ° C, especially more than 25 ° C large difference in temperature between the boiling point and the temperature at which distilled 90% by volume, can be achieved by the addition of known additives often no sufficient paraffin dispersion.
  • alkylphenol-aldehyde resins which themselves have a paraffin-dispersing action, are excellent solubilizers between these substances.
  • the invention relates to a process for improving the flowability of paraffin-containing mineral oils and mineral oil distillates, according to claim 1.
  • the alkylphenols are preferably para-substituted. They are preferably substituted at most 7 mol%, in particular at most 3 mol%, with more than one alkyl group.
  • the use of the alkylphenol-aldehyde resins B in combination with the ethylene / vinyl ester co- / terpolymers A and optionally the paraffin dispersants C other than B has a positive effect on the paraffin dispersion, i. the accumulation of paraffin crystals precipitated on cooling, e.g. on the tank bottom or the fuel filter, is delayed or prevented. As a result of the uniform dispersion of the paraffin crystals, a homogeneously turbid phase is obtained. There is also an improvement in the cold flow properties, in particular the filterability of the additized paraffinic mineral oils and in particular mineral oil distillates below the cloud point.
  • the additives A, B and, if appropriate, C may be the paraffin-containing mineral oils or mineral oil distillates be added separately.
  • the individual additives or the corresponding mixtures are dissolved or dispersed in an organic solvent or dispersion medium before addition to the mineral oils or mineral oil distillates.
  • the solution or dispersion contains 5-90, preferably 5-75 wt .-% 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 invention further mineral oils or mineral oil distillates, according to claim 13.
  • the mineral oils or mineral oil distillates may also contain other conventional additives such as dewaxing aids, corrosion inhibitors, antioxidants, lubricity additives, sludge inhibitors, Cetanierevermonyer, detergent additives, dehazers, conductivity improvers or dyes.
  • the invention further provides an additive mixture for paraffin dispersion in paraffin-containing mineral oils and mineral oil distillates 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 is added as a solubilizer.
  • Another object of the invention is a process for the preparation of solutions of paraffin dispersants in aliphatic or aromatic liquid hydrocarbons by adding an alkylphenol-aldehyde resin to the mixture of these substances.
  • Alkylphenol-aldehyde resins B are known in principle and, for example, in Römpp Chemie Lexikon, 9th edition, Thieme Verlag 1988-92, Volume 4, p 3351ff. described.
  • the alkyl radicals of the o- or p-alkylphenol especially have 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 may also contain up to 50 mol% phenol units.
  • the same or different alkylphenols may be used.
  • the aliphatic aldehyde in the alkylphenol-aldehyde resin B has 1-4 carbon atoms and is preferably formaldehyde.
  • the molecular weight of the alkylphenol-aldehyde resins is 400-10,000, preferably 400-5,000, g / mol. requirement here is that the resins are oil-soluble.
  • the preparation of the alkylphenol-aldehyde resins B takes place in a known manner by basic catalysis, resulting in condensation products of the resol type, or by acid catalysis, resulting in condensation products of the novolac type.
  • the condensates obtained according to both types are suitable as additives B in the process according to the invention.
  • the condensation is in the presence of acidic catalysts.
  • alkylphenol-aldehyde resins are a bifunctional o- or p-alkylphenol having 4 to 12 carbon atoms, in particular 6 to 12 carbon atoms per alkyl group, or mixtures thereof and an aliphatic aldehyde having 1 to 4 carbon atoms with each other reacted, wherein per mole of alkylphenol about 0.5 to 2 mol, preferably 0.7 to 1.3 mol and in particular equimolar amounts of aldehyde are used.
  • Suitable alkylphenols are C 4 -C 12 -alkylphenols such as, for example, 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 may contain small amounts, preferably up to about 10 mol%, in particular up to 7 mol% and especially up to 3 mol% of dialkylphenols.
  • aldehydes are formaldehyde, acetaldehyde and butyraldehyde, with formaldehyde being preferred.
  • the formaldehyde may be used in the form of paraformaldehyde or in the form of a preferably 20-40% by weight aqueous formalin solution. Corresponding amounts of trioxane can also be used.
  • alkylphenol and aldehyde is usually carried out in the presence of alkaline catalysts, for example alkali metal 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 Azeotrope-forming organic solvent, for example toluene, xylene, higher aromatics or mixtures thereof.
  • the reaction mixture is heated to a temperature of 90 to 200 ° C, preferably 100 to 160 ° C, wherein the resulting reaction water is removed during the reaction by azeotropic distillation.
  • Solvents that do not release protons under condensation conditions may remain in the products after the condensation reaction.
  • the resins may be used directly or after neutralization of the catalyst, optionally 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 Naphtha
  • monomeric polar nitrogen-containing compounds according to claim 1 C for example, the following substances can be used.
  • EP-A-0 413 279 describes suitable reaction products of alkenyl spiro-bis-lactones with amines.
  • oil-soluble reaction products of phthalic anhydride with amines disclosed in EP-A-0 061 894 can be used in admixture with ethylene-vinyl acetate copolymers.
  • reaction products of aminoalkylenecarboxylic acids with primary or secondary amines known from EP-A-0 597 278 are suitable as monomeric nitrogen-containing compounds according to claim 1 C.
  • polymeric polar nitrogen-containing compounds according to claim 1 C preference is given to using copolymers or terpolymers based on ⁇ , ⁇ -unsaturated compounds and maleic acid. Suitable examples are:
  • copolymers based on ⁇ , ⁇ -unsaturated olefins having at least 3 C atoms and ⁇ , ⁇ -unsaturated dicarboxylic acid anhydrides known from EP-A-0 688 796, where the dicarboxylic acid anhydride units are prepared by polymer-analogous reaction with polyetheramines or alkanolamines in imide, Amide and ammonium units were transferred;
  • copolymers based on aliphatic olefins and maleic anhydride disclosed in EP-A-0 283 293, which copolymer has both ester and amide groups, each containing an alkyl group of at least 10 carbon atoms.
  • additive A it is also possible to use mixtures of different ethylene vinyl ester copolymers or terpolymers which have a different qualitative and / or quantitative composition and / or different (measured at 140 ° C.) Have viscosities.
  • additive B mixtures of alkylphenol-aldehyde resins are also usable which contain various alkylphenols and / or aldehydes as components.
  • mixtures of several of B different paraffin dispersants C can be used. In this way, the flow improvers can be adapted to individual requirements.
  • additives A, B and, if appropriate, C oils of animal, vegetable or mineral origin can be added in the process according to the invention.
  • Paraffin-containing mineral oils and mineral oil distillates in the context of the invention are, for example, crude oils, petroleum refining residues or other paraffin-containing oils. (See, for example, Compositions and Properties of Petroleum, F. Enke Publishers, Stuttgart 1981, page 1-37).
  • Paraffin-containing mineral oil products, especially middle distillates such as jet fuel, diesel, fuel oil EL and heavy fuel oil are characterized by a boiling range of 120-500 ° C, preferably 150-400 ° C.
  • the paraffins are straight-chain or branched alkanes having about 10 to 50 carbon atoms.
  • the cold flow behavior was determined as follows:
  • test oils were admixed at room temperature with the amounts of the additives heated to 60 ° C. in Table 2, warmed to 40 ° C. for 15 minutes with occasional shaking and then cooled to room temperature.
  • the CFPP value (cold filter plugging point) was determined in accordance with EN 116 from the middle distillate so additized.
  • the paraffin dispersion in middle distillates was detected in the short sediment test as follows:
  • the additized middle distillates were cooled to -13 ° C. in a cold cabinet at -2 ° C./hour in 200 ml graduated cylinders and stored at this temperature for 16 hours. Subsequently, the volume and appearance of both the sediment (paraffin phase) and the overlying oil phase were determined and assessed visually. A small amount of sediment and a cloudy oil phase show a good paraffin dispersion.
  • A3 150 -21 25 75 clear +3.1 9.1 27 A3 300 -24 21 79 clear +3.4 9.4 28 A3 150 B1 150 -25 11 89 cloudy -2.5 3.5 29 A3 150 B1 100 C1 50 -24 0 100 cloudy -5.7 0.3 30 A3 150 B1 75 C1 75 -25 0 100 cloudy -5.0 1.0 31 A3 150 B1 50 C1 100 -27 0 100 cloudy -5.0 1.0 32 A3 150 C1 150 -25 22 88 cloudy -0.5 5.5 33 A3 150 B2 50 C1 100 -26 0 100 cloudy -5.5 0.5 20, 22, 26, 27, 32 Comparative Examples Ex.

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EP97122900A 1997-01-07 1997-12-24 Verbesserung der Fliessfähigkeit von Mineralölen und Mineralöldestillaten unter Verwendung von Alkylphenol-Aldehydharzen Expired - Lifetime EP0857776B2 (de)

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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
NO980064D0 (no) 1998-01-06
KR19980070366A (ko) 1998-10-26
US5998530A (en) 1999-12-07
ATE223953T1 (de) 2002-09-15
KR100523677B1 (ko) 2006-01-27
CA2226278A1 (en) 1998-07-07
EP0857776A1 (de) 1998-08-12
CA2226278C (en) 2006-10-24
ES2183073T5 (es) 2007-10-16
NO980064L (no) 1998-07-08
JPH10245575A (ja) 1998-09-14
JP4132167B2 (ja) 2008-08-13
EP0857776B1 (de) 2002-09-11

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