EP0900836B2 - Additif pour améliorer l'écoulement d'huiles minérales et de distillats d'huile minérale - Google Patents

Additif pour améliorer l'écoulement d'huiles minérales et de distillats d'huile minérale Download PDF

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Publication number
EP0900836B2
EP0900836B2 EP98115479A EP98115479A EP0900836B2 EP 0900836 B2 EP0900836 B2 EP 0900836B2 EP 98115479 A EP98115479 A EP 98115479A EP 98115479 A EP98115479 A EP 98115479A EP 0900836 B2 EP0900836 B2 EP 0900836B2
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Prior art keywords
additive
carbon atoms
ethylene
esters
alkyl
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EP98115479A
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German (de)
English (en)
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EP0900836A1 (fr
EP0900836B1 (fr
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Matthias Dr. Krull
Werner Dr. Reimann
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Clariant Produkte Deutschland GmbH
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Clariant Produkte Deutschland GmbH
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Definitions

  • the invention relates to an additive for improving the flowability of paraffin-containing mineral oils and mineral oil distillates, containing flow improvers based on ethylene-vinyl ester copolymers and terpolymers, polar nitrogen compounds and ethers and / or esters as solubilizers.
  • 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 crystallization phenomenon especially in winter to deposits on the pipe walls, in some cases, eg. B. at standstill 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 to disperse the precipitated 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.
  • paraffin dispersants which can generally be used together with co- or terpolymers of ethylene and vinyl esters for the addition of mineral oils and mineral oil distillates.
  • DE-A-40 19 623 discloses crystallization inhibitors for paraffins in petroleum fractions consisting of fatty amines and solutions of benzoic or formic acid in methanol, ethanol, cyclohexanol or isopropanol.
  • EP-A-0 104 015 discloses the use of weak organic acids, especially aromatic acids such as benzoic acid, alkylphenols and alkarylsulfonic acids to improve the solubility of nitrogen compounds in oils.
  • U.S. 4,210,424 discloses the use of polymers derived from carboxylic acid esters bearing alkyl side chains of from 6 to 30 carbon atoms, and / or C 8 -C 18 alkanols as solubilizers in compositions of ethylene copolymers, paraffin waxes and nitrogen compounds.
  • EP-A-0 733 694 discloses solvent mixtures of aliphatic or alicyclic alcohols having at least 4 carbon atoms and aromatic hydrocarbons in a ratio of 10: 1 to 1: 2. The solvents are used to form a homogeneous mixture together with oil-soluble additives containing NR groups wherein R is a hydrocarbon radical of 8 to 40 carbon atoms.
  • EP-A-0 398 101 discloses reaction products of aminoalkylene polycarboxylic acids with secondary amines and their use as an additive to middle distillates optionally together with as flow improvers known ethylene copolymers and conductivity improvers, wherein 2-EH-phthalate may be included.
  • the task was therefore to find more efficient solubilizers between the polar nitrogen compounds and the ethylene / vinyl ester copolymers and terpolymers.
  • Another object of the invention is a process for improving the flowability of mineral oils and mineral oil distillates, characterized in that they are added to the inventive additive.
  • R and the acid radical are preferably linear or branched alkyl or alkenyl groups having 5 to 22 carbon atoms.
  • R 'and the alcohol radical are preferably linear or branched alkyl or alkenyl groups having 2 to 22 carbon atoms.
  • ethers are dihexyl ether, dioctyl ether, di (2-ethylhexyl) ether
  • esters are oleic acid ester, 2-ethylhexyl stearate, 2-ethylhexyl acid butyrate, ethyl octanoate, ethylhexanoate, butyl 2-ethylhexylate, 2-ethylhexyl butyrate and Called 2-ethylhexyl acid 2-ethylhexyl ester.
  • solubilizers are esters
  • the use of mono- and diesters of both dialcohols and dicarboxylic acids is preferred.
  • esters adipic acid di (2-ethylhexyl ester) may be mentioned.
  • the additive in addition to the ethers and / or esters, up to 30% by weight of alkylphenol-aldehyde resins and / or up to 10% by weight of alcohols, aldehydes and / or acetals (in each case based on the entire preparation) ,
  • the mixtures may further contain aliphatic and / or aromatic solvents.
  • mixtures containing ethers and esters, such as, for example, as a by-product of the oxo process are used.
  • a solvent mixture originating from the oxosynthesis hereinafter referred to as MS, is added as a solubilizer.
  • MS is a mixture of a number of aliphatic and cyclic non-aromatic hydrocarbons.
  • the main components of MS can be found in the following table: component Concentration range (wt%) Di-2-ethylhexyl 10 - 25 2-ethylhexyl acid-2-ethylhexyl 10 - 25 C 16 lactones 4 - 20 2-Ethylhexylbutyrat 3 - 10 2-ethylhexanediol- (1,3) glycol mono-n-butyrate 5 - 15 2-ethylhexanol 4 - 10 C 4 to C 8 acetals 2 - 10 2-ethylhexanediol- (1,3) 2 - 5 Ethers and esters ⁇ C 20 0 - 20
  • Particularly preferred terpolymers of ethylene and vinyl esters are those which, in addition to 65 to 94 mol% of the structural units derived from ethylene and 5 to 35 mol% of vinyl acetate, contain 1 to 25 mol% of structural units of the formula (2) wherein R 3 is saturated, branched C 6 -C 16 alkyl having a tertiary carbon atom.
  • the copolymers and terpolymers used for the additive mixture may also contain up to 5 mol% of monomer units derived from olefins such as vinyl ethers, alkyl acrylates, alkyl methacrylates, isobutylene or higher olefins having at least 5 carbon atoms such as Witches, 4-methylpentene, octene or diisobutylene derived.
  • olefins such as vinyl ethers, alkyl acrylates, alkyl methacrylates, isobutylene or higher olefins having at least 5 carbon atoms such as Witches, 4-methylpentene, octene or diisobutylene derived.
  • the polar nitrogen-containing compounds are preferred.
  • monomeric polar nitrogen-containing compounds for example, the following substances can be used:
  • EP-A-0 061 894 disclosed oil-soluble reaction products of phthalic anhydride with amines can be used in admixture with ethylene-vinyl acetate copolymers. Furthermore, the off EP-A-0 597 278 known reaction products of Aminoalkylencarbonklaren with primary or secondary amines suitable as monomeric nitrogen-containing compounds.
  • the mixtures according to the invention are added to mineral oils or mineral oil distillates in the form of concentrates.
  • These concentrates preferably contain 1 to 70, in particular 5 to 60 wt .-% of vinyl ester copolymers and paraffin dispersants in the ratio 1:10 to 10: 1, in particular in the ratio 1: 5 to 5: 1 and 1 to 60 wt .-% in particular from 5 to 50% by weight of the solvents according to the invention.
  • the remainder to 100% may be aliphatic, aromatic solvents and alkylphenol resins, alcohols, aldehydes and / or acetals.
  • Mineral oils or mineral oil distillates improved in their rheological properties by the mixtures according to the invention contain from 0.001 to 2, preferably from 0.005 to 0.5,% by weight of the mixtures, based on the distillate.
  • the mixtures according to the invention can also be used together with one or more oil-soluble co-additives, which already by itself the cold flow properties of crude oils, lubricating oils or fuel oils improve, such as comb polymers.
  • Comb polymers are polymers in which hydrocarbon radicals having at least 8, in particular at least 10, carbon atoms are bonded to a polymer backbone. Preferably, they are homopolymers whose alkyl side chains contain at least 8 and in particular at least 10 carbon atoms.
  • copolymers at least 20%, preferably at least 30% of the monomers have side chains (compare Comb-like Polymers - Structure and Properties, NA Platé and VP Shibaev, J. Polym, Sci Macromolecular Revs 1974, 8, 117 ff).
  • suitable comb polymers are, for. As fumarate / vinyl acetate copolymers (see. EP-A-0 153 176 ), Copolymers of a C 6 -C 24 - ⁇ -olefin and a NC 6 - to C 22 -alkylmaleimide (cf.
  • EP-A-0 320 766 Further, esterified olefin / maleic anhydride copolymers, polymers and copolymers of ⁇ -olefins and esterified copolymers of styrene and maleic anhydride.
  • the mixing ratio (in parts by weight) of the mixtures according to the invention with comb polymers is 1:10 to 20: 1, preferably 1: 1 to 10: 1.
  • the mixtures according to the invention are suitable for improving the cold flow properties of animal, vegetable or mineral oils. They are particularly well suited for use with middle distillates.
  • middle distillates are in particular those mineral oils which are obtained by distillation of crude oil and boil in the range of 120 to 450 ° C, for example kerosene, jet fuel, diesel and fuel oil.
  • the concentrates show a significantly improved storage stability, especially at low temperatures.
  • novel mixtures may be used alone or together with other additives, for example dewaxing aids, corrosion inhibitors, antioxidants, lubricity additives or sludge inhibitors.
  • additives for example dewaxing aids, corrosion inhibitors, antioxidants, lubricity additives or sludge inhibitors.
  • the addition of these additives to the oil can be carried out together with the mixture according to the invention or else separately.
  • MS solvent mixture consisting of the following main components: Di-2-ethylhexyl 20% 2-ethylhexyl acid-2-ethylhexyl 14% C 16 lactones 17% 2-ethylhexanediol- (1,3) glycol mono-n-butyrate 10% 2-Ethylhexylbutyrat 5% 2-ethylhexanol 5% C 4 to C 8 acetals 10% Ether / ester ⁇ C 20 19%
  • the mixtures according to the invention Upon reheating, the mixtures according to the invention remain homogeneous.

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  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
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Claims (8)

  1. Additif pour améliorer la fluidité d'huiles minérales et de distillats d'huiles minérales paraffiniques, contenant un mélange d'au moins un co- ou terpolymère éthylène/ester de vinyle et d'au moins un agent dispersant azoté de la paraffine, qui est un composé polaire, de faible masse moléculaire ou polymère oléosoluble, qui contient un ou plusieurs groupes amide et/ou imide substitués avec au moins une chaîne alkyle en C8 à C26, et/ou porte un ou plusieurs groupes ammonium, qui dérive d' amines avec un ou deux groupes alkyle en C8 à C26, caractérisé en ce que le mélange indiqué contient comme agent solubilisant des éthers et des esters, dans lesquels
    a) les éthers correspondent à la formule 1

            R-O-R'     (1),

    dans laquelle R représente des groupes alkyle ou alcényle linéaires ou ramifies avec de 4 à 30 atomes de carbone et R' représente des groupes alkyle ou alcényle linéaires ou ramifiés avec de 1 à 30 atomes de carbone,
    b) les esters dérivent d'acides carboxyliques mono- ou polyvalents ayant des groupes alkyle ou alcényle linéaires ou ramifiés avec de 5 à 22 atomes de carbone (reste acide) et d'alcools mono- ou polyhydroxylés ayant des groupes alkyle ou alcényle linéaires ou ramifiés avec de 2 à 22 atomes de carbone (reste alcool), ou
    C) les éthers et/ou esters sont cycliques, dans lesquels R et R' ou le reste acide et alcool forment un cycle avec de 8 à 22 chaînons de cycle.
  2. Additif selon la revendication 1, caractérisé en ce que les groupes R comprennent de 5 à 22 et les groupes R' de 2 à 22 atomes de carbone.
  3. Additif selon la revendication 1 et/ou 2, caractérisé en ce qu'on utilise un mélange MS comme agent solubilisant, dans lequel MS présente la composition suivante : Constituant Gamme de concentration (% en poids) di-2-éthylhexyléther 10-25 ester 2-éthylhexylique d'acide 2-éthylhexylique 10-25 lactone en C16 4-20 butyrate de 2-éthylhexyle 2-éthylhexanediol-(1,3)- 3-10 mono-n-butyrate 5-15 2-éthylhexanol 4-10 acétals en C4 à C8 2-10 2-êthylhexane-(1,3)-diol 2-5 éther et ester = C20 0-20
  4. Additif selon une ou plusieurs des revendications 1 à 3, caractérisé en ce qu'il contient en plus jusqu'à 10 % en poids d'alcools et/ou jusqu'à 30 % en poids de résines alkylphénol-aldéhyde.
  5. Additif selon une ou plusieurs des revendications 1 à 4, caractérisé en ce qu'il contient au moins un copolymère d'éthylène et un ou plusieurs esters de vinyle.
  6. Additif selon une ou plusieurs des revendications 1 à 5, caractérisé en ce qu'il contient un terpolymère, qui présente en plus de 65 à 94 % en mole de motifs de structure dérivés de l'éthylène et de 5 à 35 % en mole dérivés de l'acétate de vinyle encore 1 à 25 % en mole de motifs de structure de formule (2)
    Figure imgb0004
    dans laquelle R3 représente un groupe alkyle saturé, ramifié en C6 à C16 qui présente un atome de carbone tertiaire.
  7. Procédé pour l'amélioration de la fluidité d'huiles minérales et de distillats d'huiles minérales, caractérisé en ce qu'on ajoute des additifs selon une ou plusieurs des revendications 1 à 6.
  8. Huiles minérales et distillats d'huiles minérales, contenant des additifs selon une ou plusieurs des revendications 1 à 6.
EP98115479A 1997-09-08 1998-08-18 Additif pour améliorer l'écoulement d'huiles minérales et de distillats d'huile minérale Expired - Lifetime EP0900836B2 (fr)

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DE59810065D1 (de) 2003-12-11
JPH11166186A (ja) 1999-06-22
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KR100599016B1 (ko) 2006-12-28
US6010989A (en) 2000-01-04
EP0900836B1 (fr) 2003-11-05
SK123098A3 (en) 1999-04-13
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