EP0900836A1 - Additif pour améliorer l'écoulement d'huiles minérales et de distallats d'huile minérale - Google Patents

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

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Publication number
EP0900836A1
EP0900836A1 EP98115479A EP98115479A EP0900836A1 EP 0900836 A1 EP0900836 A1 EP 0900836A1 EP 98115479 A EP98115479 A EP 98115479A EP 98115479 A EP98115479 A EP 98115479A EP 0900836 A1 EP0900836 A1 EP 0900836A1
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European Patent Office
Prior art keywords
carbon atoms
ethylene
ester
additive
homogeneous
Prior art date
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Granted
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EP98115479A
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German (de)
English (en)
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EP0900836B1 (fr
EP0900836B2 (fr
Inventor
Matthias Dr. Krull
Werner Dr. Reimann
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Clariant Produkte Deutschland GmbH
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Clariant GmbH
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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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    • C10L2250/00—Structural features of fuel components or fuel compositions, either in solid, liquid or gaseous state
    • 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 polar on the basis of ethylene-vinyl ester copolymers and terpolymers 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 ones depending on the origin of the crude oils Amounts of n-paraffins which, when the temperature is lowered, are platelet-shaped 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. B. when 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 failed paraffin crystals, d. H. 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.
  • 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.
  • the task was therefore to find more efficient solvent mediators between the polar 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 include oleic acid eicosyl ester, 2-ethylhexyl stearate, 2-ethylhexyl acid butyrate, Ethyl octanoate, ethyl hexanoate, butyl 2-ethylhexyl acid, 2-ethylhexyl butyrate and 2-ethylhexyl acid-2-ethylhexyl ester called.
  • R and R 'or the acid and the alcohol residue a ring with 8 to 22 ring members.
  • solubilizers are esters
  • the use of mono- and 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.
  • ethers and esters containing mixtures such as as a by-product in the Oxosynthesis arise, 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 ether 10 - 25 2-ethylheryl acid-2-ethylhexyl ester 10 - 25 C 16 lactones 4 - 20 2-ethylhexyl butyrate 3 - 10 2-ethylhexanediol (1,3) 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, in addition to the monomer units mentioned, 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 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 suitable.
  • the mixtures according to the invention become mineral oils or mineral oil distillates added 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 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.
  • 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 Paté 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 -alkyl maleimide (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, 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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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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EP1134273A2 (fr) * 2000-03-16 2001-09-19 Clariant GmbH Mélanges d'acides carboxyliques,leurs dérivés et de polymères portant des groupes hydroxyles, et leurs utilisations pour l'amélioration du pouvoir lubrifiant d'huiles
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EP1116780A1 (fr) * 2000-01-11 2001-07-18 Clariant GmbH Additif polyfonctionnel pour huiles combustibles
EP1116781A1 (fr) * 2000-01-11 2001-07-18 Clariant GmbH Additif polyfonctionnel pour huiles combustibles
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US20170145290A1 (en) * 2014-07-15 2017-05-25 Nelson Akaighe Compositions and Methods for Controlling Paraffin and Asphaltene Problems in Wells
WO2016011018A1 (fr) * 2014-07-15 2016-01-21 Sasol Performance Chemicals Gmbh Compositions et procédés pour contrôler les problèmes de paraffine et d'asphaltène dans des puits
CN106715638A (zh) * 2014-07-15 2017-05-24 萨索尔功能化学品有限公司 用于处理油气井的组合物和方法
WO2016011015A1 (fr) * 2014-07-15 2016-01-21 Sasol Performance Chemicals Gmbh Compositions et procédés de traitement de puits de pétrole et de gaz
CN106795425A (zh) * 2014-07-15 2017-05-31 萨索尔功能化学品有限公司 用于在井中控制石蜡和沥青质问题的组合物和方法
US10259986B2 (en) 2014-07-15 2019-04-16 Sasol Performance Chemicals Gmbh Compositions and methods for treating oil and gas wells
AU2015289868B2 (en) * 2014-07-15 2019-07-11 Sasol Performance Chemicals Gmbh Compositions and methods for treating oil and gas wells
AU2015289871B2 (en) * 2014-07-15 2019-07-11 Sasol Performance Chemicals Gmbh Compositions and methods for controlling paraffin and asphaltene problems in wells
RU2711435C2 (ru) * 2014-07-15 2020-01-17 Сэсол Перформанс Кемикалз Гмбх Композиции и способы для решения проблем с парафинами и асфальтенами в скважинах
RU2711436C2 (ru) * 2014-07-15 2020-01-17 Сэсол Перформанс Кемикалз Гмбх Композиции и способы для обработки нефтяных и газовых скважин
US10711175B2 (en) 2014-07-15 2020-07-14 Sasol Performance Chemicals Gmbh Compositions and methods for controlling paraffin and asphaltene problems in wells
US11084968B2 (en) 2014-07-15 2021-08-10 Sasol Chemicals Gmbh Compositions and methods for treating oil and gas wells

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DE59810065D1 (de) 2003-12-11
ES2209018T5 (es) 2008-11-01
DE19739271A1 (de) 1999-03-11
EP0900836B1 (fr) 2003-11-05
US6010989A (en) 2000-01-04
NO984119L (no) 1999-03-09
KR19990029579A (ko) 1999-04-26
NO984119D0 (no) 1998-09-07
SK123098A3 (en) 1999-04-13
EP0900836B2 (fr) 2008-06-11
ES2209018T3 (es) 2004-06-16
JPH11166186A (ja) 1999-06-22
KR100599016B1 (ko) 2006-12-28
CA2246580A1 (fr) 1999-03-08
JP4592124B2 (ja) 2010-12-01
ATE253623T1 (de) 2003-11-15

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