EP2809750A1 - Procédé permettant de réduire les salissures lors du traitement d'hydrocarbures liquides - Google Patents

Procédé permettant de réduire les salissures lors du traitement d'hydrocarbures liquides

Info

Publication number
EP2809750A1
EP2809750A1 EP13701920.4A EP13701920A EP2809750A1 EP 2809750 A1 EP2809750 A1 EP 2809750A1 EP 13701920 A EP13701920 A EP 13701920A EP 2809750 A1 EP2809750 A1 EP 2809750A1
Authority
EP
European Patent Office
Prior art keywords
use according
alkyl
radical
polyester
anhydride
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.)
Withdrawn
Application number
EP13701920.4A
Other languages
German (de)
English (en)
Inventor
Michael Feustel
Dominko ANDRIN
Matthias Krull
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant International Ltd
Original Assignee
Clariant Finance BVI Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE201210004882 external-priority patent/DE102012004882A1/de
Application filed by Clariant Finance BVI Ltd filed Critical Clariant Finance BVI Ltd
Publication of EP2809750A1 publication Critical patent/EP2809750A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G75/00—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general
    • C10G75/04—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general by addition of antifouling agents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G9/00—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
    • C10G9/14—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils in pipes or coils with or without auxiliary means, e.g. digesters, soaking drums, expansion means
    • C10G9/16—Preventing or removing incrustation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—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
    • C10L1/1983—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 polyesters

Definitions

  • Alkene mixtures proven. These preferably contain at least 50 wt .-%, particularly preferably 60 to 99 wt .-% and in particular 70 to 95 wt .-% such as 75 to 90 wt .-% terminal double bonds ( ⁇ -olefins).
  • R 6 or R 7 is methyl, ethyl or propyl and especially methyl, and the other group is an oligomer of the C 3 -C 6 -olefin.
  • the alkylvinylidene content can be determined, for example, by means of 1 H-NMR spectroscopy.
  • the number of carbon atoms in the polyolefin is between 41 and 400. In a preferred embodiment of the invention, the number of carbon atoms is between 50 and 3000 and in particular between 55 and 200.
  • the C 4 iC 0 o-alkyl or alkenyl underlying polyolefins for example, by ionic polymerization accessible and available as commercial products (eg. B Glissopal ®, BASF polyisobutenes of different
  • r and s independently represent a number from 1 to 9 and
  • the catalysts are preferably added to the reaction mixture in amounts of from 0.01 to 10% by weight, more preferably from 0.1 to 5% by weight, based on the weight of the reaction mixture.
  • the polycondensation of glycerol can be carried out solvent-free as well as in the presence of solvent. If the polycondensation takes place in the presence of solvent, its proportion in the reaction mixture is preferably from 0.1 to 70% by weight, for example from 10 to 60% by weight.
  • Preferred organic solvents are the dicarboxylic acid which is also used for the condensation of the alk (en) yl radicals, their anhydride or their ester and solvent used with the polyol.
  • the polycondensation of glycerol generally takes 3 to 10 hours. This method is analogously applicable to the polycondensation of other polyols.
  • Alkylbenzenes and alkylnaphthalenes For example, aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures, for. B.
  • Preferred acidic organic catalysts are acidic organic compounds with, for example, phosphate groups, sulfonic acid groups, sulfate groups or phosphonic acid groups. Contain particularly preferred sulfonic acids
  • aromatic sulfonic acids and especially alkylaromatic monosulfonic acids having one or more C 1 -C -alkyl radicals and, in particular, those containing C 3 -C 22 -alkyl radicals.
  • alkylaromatic monosulfonic acids having one or more C 1 -C -alkyl radicals and, in particular, those containing C 3 -C 22 -alkyl radicals.
  • Suitable examples are methanesulfonic acid, butanesulfonic acid,
  • Catalysts are used according to the invention 0.01 to 10 wt .-%, preferably 0.02 to 2 wt .-% catalyst. In a specific embodiment, the condensation takes place without the addition of catalysts.
  • Cie-monocarboxylic acids preferably C 2 - to Ci6-monocarboxylic acids, and especially C 3 - to C 4 monocarboxylic acids such as C 4 - to Ci2 monocarboxylic acids replaced.
  • C 3 - to C 4 monocarboxylic acids such as C 4 - to Ci2 monocarboxylic acids replaced.
  • Fumaric acid are replaced.
  • the hydroxyl-bearing polyesters are prepared in the absence of monocarboxylic acids.
  • Hydroxyl group-bearing polyester is preferably between 4 and 200, particularly preferably between 5 and 150, especially between 7 and 100 and in particular between 0 and 70 such as between 15 and 50 repeating units of dicarboxylic acid and polyol. Under the
  • the degree of condensation is understood to be the sum of m + p + q according to formula (A).
  • the weight-average molecular weight M w of the hydroxyl group-carrying polyester determined by GPC in THF against poly (ethylene glycol) standard is preferably between 2,000 g / mol and 600,000 g / mol. at
  • the acid number of the hydroxyl-carrying polyester is less than 40 mg KOH / g and more preferably less than 30 mg KOH / g as
  • the acid value can be determined, for example, by titration of the polymer with alcoholic tetra-n-butylammonium hydroxide solution in xylene / isopropanol.
  • the hydroxyl number of the polyester is between 40 and 500 mg KOH / g, particularly preferably between 50 and 300 mg KOH / g and in particular between 60 and 250 mg KOH / g.
  • the nitrogen content can be determined, for example, according to Kjeldahl.
  • biogenic raw materials accessible products such as animal and vegetable oils and fats and their derivatives such as
  • Hydrocarbon media are preferably added in amounts of from 0.5 to 5,000 ppm by weight, more preferably from 1, 0 to 1,000 ppm by weight, for example from 2 to 500 ppm by weight.
  • the polyesters can be in the liquid
  • Hydrocarbon medium dispersed or dissolved Preferably, they are solved.
  • Preferred solvents are the solvents and solvent mixtures already mentioned as solvents for the condensation reaction between dicarboxylic acid and polyol. Particularly preferred are aromatic solvents.
  • the proportion of the polyester in the concentrate is preferably from 5 to 95% by weight, particularly preferably from 10 to 80% by weight and in particular from 20 to 70% by weight, for example from 25 to 60% by weight.
  • Hydrocarbon media has often been found to aid in the incorporation of the polyester into the liquid hydrocarbon medium by means of static or dynamic mixing devices. Particularly advantageous are the use according to the invention of hydroxyl-bearing polyesters and the process using them in the processing or treatment of liquid hydrocarbon media above 100.degree. C., especially between 150 and 500.degree. C. and in particular between 200.degree. C. and 480.degree. C., for example between 250.degree C and 450 ° C.
  • the inventive method is generally suitable for reducing and often suppressing fouling in the processing of liquid hydrocarbon media at higher temperatures.
  • the acid value of the polymer was 6.5 mg KOH / g, the hydroxyl number was 195 mg KOH / g and the weight average molecular weight was 8,700 g / mol.
  • Amounts of poly (isobutenyl) succinic anhydride (prepared by thermal condensation of maleic anhydride with poly (isobutene) having an average molecular weight Mn of 1,000 g / mol and a
  • the acid value of the polymer was 8.6 mg KOH / g, the hydroxyl value was 47 mg KOH / g and the weight-average molecular weight was 14,000 g / mol.
  • Proportions of poly (isobutenyl) succinic anhydride prepared by thermal condensation of maleic anhydride with poly (isobutene) having an average molecular weight Mn of 2,300 g / mol and a
  • Heating rod was about 400 ° C) reached maximum temperature of the oil at the outlet of the stainless steel capillary registered (T1). On the other hand, the temperature of the oil was registered in the same place after a test time of 5 hours (T2). Since the deposits formed by fouling on the heating rod have a poor thermal conductivity, the initial maximum temperature reached correlates indirectly (low initial temperature T1 implies immediate onset of fouling) and the difference in temperatures T2 and T1 directly with the extent of fouling.
  • Stainless steel capillary oil (T2) adhering temperature recorded and the experiment ended.
  • Target temperature of the oil is specified, the inventive method also leads to energy savings.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

L'invention concerne l'utilisation, comme produit antisalissure lors du traitement thermique d'hydrocarbures liquides dans une plage de température comprise entre 100 et 500 °C, d'un polyester portant des groupes hydroxyle, qui est produit par polycondensation d'un polyol contenant deux groupes OH primaires et au moins un groupe OH secondaire avec un acide dicarboxylique ou un anhydride ou un ester dudit acide, qui porte un reste alkyle en C16 à C400 ou un reste alcényle en C16 à C400.
EP13701920.4A 2012-01-31 2013-01-29 Procédé permettant de réduire les salissures lors du traitement d'hydrocarbures liquides Withdrawn EP2809750A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102012001821 2012-01-31
DE201210004882 DE102012004882A1 (de) 2012-03-10 2012-03-10 Verfahren zur Verminderung von Fouling bei der Verarbeitung flüssiger Kohlenwasserstoffe
PCT/EP2013/000254 WO2013113491A1 (fr) 2012-01-31 2013-01-29 Procédé permettant de réduire les salissures lors du traitement d'hydrocarbures liquides

Publications (1)

Publication Number Publication Date
EP2809750A1 true EP2809750A1 (fr) 2014-12-10

Family

ID=47630247

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13701920.4A Withdrawn EP2809750A1 (fr) 2012-01-31 2013-01-29 Procédé permettant de réduire les salissures lors du traitement d'hydrocarbures liquides

Country Status (9)

Country Link
US (1) US20140338254A1 (fr)
EP (1) EP2809750A1 (fr)
JP (1) JP6095131B2 (fr)
KR (1) KR20140128289A (fr)
CN (1) CN104066820B (fr)
BR (1) BR112014011956A2 (fr)
CA (1) CA2863267A1 (fr)
EA (1) EA025207B9 (fr)
WO (1) WO2013113491A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9505994B2 (en) * 2014-02-05 2016-11-29 Baker Hughes Incorporated Antifoulants for use in hydrocarbon fluids
EP3201297B1 (fr) * 2014-10-02 2020-07-15 Croda, Inc. Inhibition de l'asphaltène
US10717917B2 (en) 2016-06-24 2020-07-21 Croda, Inc. Method and composition for asphaltene dispersion
AR110322A1 (es) * 2016-12-07 2019-03-20 Ecolab Usa Inc Dispersantes poliméricos para corrientes del proceso de petróleo
EP3786561B1 (fr) 2019-09-02 2022-12-14 Orion Engineered Carbons IP GmbH & Co. KG Dispositif antisalissure pour échangeurs thermiques et son utilisation

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271295A (en) 1965-02-23 1966-09-06 Betz Laboratories Process of heat transfer
GB1215214A (en) 1968-05-09 1970-12-09 Exxon Research Engineering Co Fuel or oil compositions
US3447916A (en) 1965-11-10 1969-06-03 Exxon Research Engineering Co Acylated polyesters,polyesteramides,or polyamides
US4216114A (en) 1977-11-18 1980-08-05 Imperial Chemical Industries Limited Demulsification process
US4619756A (en) * 1985-04-11 1986-10-28 Exxon Chemical Patents Inc. Method to inhibit deposit formation
US5183555A (en) * 1991-08-29 1993-02-02 Betz Laboratories, Inc. Method for controlling fouling deposit formation in a liquid hydrocarbonaceous medium
US5171420A (en) * 1991-09-09 1992-12-15 Betz Laboratories, Inc. Method for controlling fouling deposit formation in a liquid hydrocarbonaceous medium
US5342505A (en) 1993-02-25 1994-08-30 Betz Laboratories, Inc. Use of polyalkenyl succinimides-glycidol reaction products as antifoulants in hydrocarbon process media
DE19505100A1 (de) 1995-02-15 1996-08-22 Basf Ag Alk(en)yldicarbonsäurebisester, deren Verwendung sowie Verfahren zu deren Herstellung
US5985940A (en) * 1998-02-17 1999-11-16 Nalco/Exxon Energy Chemicals, L.P. Method of mitigating fouling and reducing viscosity in primary fractionators and quench sections of ethylene plants
DE102004026904A1 (de) * 2004-06-01 2005-12-22 Basf Ag Hochfunktionelle, hoch- oder hyperverzweigte Polyester sowie deren Herstellung und Verwendung
GB0622947D0 (en) 2006-11-17 2006-12-27 Croda Int Plc Surfactant compounds
EP2340296B1 (fr) * 2008-08-26 2014-10-08 Dorf Ketal Chemicals (I) Private Limited Nouvel additif pour l'inhibition de la corrosion par les acides et procédé d'utilisation du nouvel additif
WO2011014215A1 (fr) 2009-07-31 2011-02-03 Exxonmobil Research And Engineering Company Processus dans lequel on utilise du polypropylène ou du poly (éthylène copropylène) succinimide en tant qu'additif antisalissure dans des processus de raffinerie de pétrole
DE102009060371A1 (de) 2009-12-24 2011-06-30 Clariant International Ltd. Multifunktionelle Additive mit verbesserter Fließfähigkeit
CN103608416B (zh) * 2011-06-23 2015-12-02 中国涂料株式会社 二液型水解型防污涂料组合物、防污涂膜及防污基材的制造方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
None *
See also references of WO2013113491A1 *

Also Published As

Publication number Publication date
CN104066820A (zh) 2014-09-24
JP2015508829A (ja) 2015-03-23
EA201400774A1 (ru) 2014-10-30
WO2013113491A1 (fr) 2013-08-08
EA025207B1 (ru) 2016-11-30
KR20140128289A (ko) 2014-11-05
CA2863267A1 (fr) 2013-08-08
JP6095131B2 (ja) 2017-03-15
EA025207B9 (ru) 2017-01-30
US20140338254A1 (en) 2014-11-20
CN104066820B (zh) 2015-11-25
BR112014011956A2 (pt) 2017-05-30

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