EP0900836B1 - 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
EP0900836B1
EP0900836B1 EP98115479A EP98115479A EP0900836B1 EP 0900836 B1 EP0900836 B1 EP 0900836B1 EP 98115479 A EP98115479 A EP 98115479A EP 98115479 A EP98115479 A EP 98115479A EP 0900836 B1 EP0900836 B1 EP 0900836B1
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Prior art keywords
additive
carbon atoms
ethylene
esters
ester
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EP98115479A
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German (de)
English (en)
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EP0900836B2 (fr
EP0900836A1 (fr
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Matthias Dr. Krull
Werner Dr. Reimann
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Clariant Produkte Deutschland GmbH
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Clariant GmbH
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    • C10L1/00—Liquid carbonaceous fuels
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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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    • 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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    • C10L2250/04—Additive or component is a polymer

Definitions

  • the invention relates to an additive for improving the flowability of mineral oils and mineral oil distillates containing paraffin and 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 distilling crude oils such as gas oil, Diesel oil or heating oil contain different amounts depending on the origin of the crude oils on n-paraffins which, when the temperature is lowered, form platelet-shaped crystals crystallize out and partially agglomerate with the inclusion of oil.
  • Flow properties of the oils or distillates which means 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 tube walls, in individual cases, e.g. B. when a pipeline is at a standstill, even for its complete blockage to lead.
  • 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 failed 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.
  • Paraffin dispersants are known, which together with Co or Terpolymers of ethylene and vinyl esters for the additive of mineral oils and Mineral oil distillates can be used.
  • DE-A-40 19 623 discloses crystallization inhibitors for paraffins in petroleum fractions, that from fatty amines and solutions of benzoic or formic acid in methanol, Ethanol, cyclohexanol or isopropanol exist.
  • 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 Oil.
  • US 4,210,424 discloses the use of polymers derived from carboxylic acid esters and bearing alkyl side chains of 6 to 30 carbon atoms and / or of 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 with at least 4 carbon atoms and aromatic Hydrocarbons in a ratio of 10: 1 to 1: 2.
  • the solvents are used to combine with oil-soluble additives containing NR groups, where R is is a hydrocarbon residue of 8 to 40 carbon atoms, a homogeneous To form mixture.
  • 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 known as flow improvers Ethylene copolymers and conductivity improvers, with 2-EH phthalate can be included.
  • the task was therefore to find more efficient solvent mediators between the polar ones Find nitrogen compounds and the ethylene / vinyl ester copolymers and terpolymers.
  • Another object of the invention is a method for improving the Flowability of mineral oils and mineral oil distillates, characterized in that that the additive according to the invention is added to them.
  • R and the acid residue are preferably linear or branched alkyl or Alkenyl groups with 5 to 22 carbon atoms.
  • R 'and the alcohol residue preferably for linear or branched alkyl or alkenyl groups with 2 to 22 Carbon atoms.
  • ethers are dihexyl ether, dioctyl ether, di (2-ethylhexyl) ether
  • esters are oleic acid eicosyl ester, 2-ethylhexyl stearate, 2-ethylhexyl acid butyrate, ethyl octanoate, ethyl hexanoate, 2-ethylhexyl butyl ester, 2-ethyl hexyl butyrate and 2-ethyl hexyl acid 2-ethyl hexyl ester called.
  • solubilizers are esters
  • the use of monound Diesters of both dialcohols and dicarboxylic acids are preferred.
  • esters are adipic acid di (2-ethylhexyl ester), 2-ethylhexanediol (1,3) mono-n-butyrate, Called 2-ethylhexanediol (1,3) di-n-butyrate.
  • alkylphenol aldehyde resins and / or up to 10% by weight of alcohols, aldehydes and / or acetals (in each case based on the entire preparation) to the additive in addition to the ethers and / or esters .
  • the mixtures can also contain aliphatic and / or aromatic solvents.
  • mixtures containing ether and ester, such as those formed as a by-product in oxosynthesis are used.
  • one of the Oxosynthesis originating hereinafter referred to as MS Solvent mixture 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 (% by weight) 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, also contain 1 to 25 mol% of structural units of the formula (2) have, wherein R 3 is saturated, branched C 6 -C 16 alkyl which has a tertiary carbon atom.
  • the copolymers and terpolymers used for the additive mixture can also contain up to 5 mol% of monomer units derived from olefins such as vinyl ethers, alkyl acrylates, alkyl methacrylates, isobutylene or higher olefins with at least 5 carbon atoms such as, for example, hexene , 4-methylpentene, octene or diisobutylene.
  • olefins such as vinyl ethers, alkyl acrylates, alkyl methacrylates, isobutylene or higher olefins with at least 5 carbon atoms such as, for example, hexene , 4-methylpentene, octene or diisobutylene.
  • the polar ones are preferred nitrogenous compounds.
  • monomeric polar nitrogen-containing compounds 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 phthalic anhydride with amines disclosed in EP-A-0 061 894 can also be used in a mixture with ethylene-vinyl acetate copolymers.
  • the reaction products of aminoalkylene carboxylic acids with primary or secondary amines known from EP-A-0 597 278 are suitable as monomeric nitrogen-containing compounds.
  • the mixtures according to the invention are mineral oils or mineral oil distillates in Form of concentrates added. These concentrates preferably contain 1 to 70, in particular 5 to 60 wt .-% of vinyl ester copolymers and Paraffin dispersants in a ratio of 1:10 to 10: 1, in particular in a ratio of 1: 5 to 5: 1 and 1 to 60 wt .-% in particular 5 to 50 wt .-% of the invention Solvent. The rest to 100% can be aliphatic, aromatic solvents as well as alkylphenol resins, alcohols, aldehydes and / or acetals. Through the Mixtures according to the invention improved in their rheological properties Mineral oils or mineral oil distillates contain 0.001 to 2, preferably 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 in themselves improve the cold flow properties of crude oils, lubricating oils or fuel oils, 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. They are preferably homopolymers whose alkyl side chains contain at least 8 and in particular at least 10 carbon atoms. In copolymers, at least 20%, preferably at least 30%, of the monomers have side chains (cf.
  • comb polymers Comb-like Polymers - Structure and Properties; NA Platé and VP Shibaev, J. Polym. Sci. Macromolecular Revs. 1974, 8, 117 ff).
  • suitable comb polymers are e.g. B. fumarate / vinyl acetate copolymers (cf. EP-A-0 153 176), copolymers of a C 6 -C 24 - ⁇ -olefin and an NC 6 - to C 22 -alkylmaleimide (cf.
  • EP-A-0 320 766 also 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 the cold flow properties of to improve animal, vegetable or mineral oils. You are for that Particularly suitable for use with middle distillates.
  • middle distillates One particularly refers to those mineral oils which are obtained by distilling crude oil be obtained and boiling in the range of 120 to 450 ° C, for example Kerosene, jet fuel, diesel and heating oil.
  • the concentrates clearly show one improved storage stability, especially at low temperatures.
  • the new mixtures can be used alone or together with others Additives are used, for example with dewaxing aids, Corrosion inhibitors, antioxidants, lubricity additives or sludge inhibitors. These additives can be added to the oil together with those of the invention Mixing or done separately.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

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 ester, amide et/ou imide substitués avec au moins une chaíne 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/ou des esters, dans lesquels
    a) les éthers correspondent à la formule 1 R-O-R' 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 chaínons 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 ester 2-éthylhexylique 10-25 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-éthylhexane-(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 00220001
    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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ES2209018T5 (es) 2008-11-01
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US6010989A (en) 2000-01-04
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ATE253623T1 (de) 2003-11-15
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NO984119D0 (no) 1998-09-07
DE19739271A1 (de) 1999-03-11

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