EP0572881B1 - Procédé de séparation d'émulsions de pétrole du type eau dans l'huile - Google Patents

Procédé de séparation d'émulsions de pétrole du type eau dans l'huile Download PDF

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Publication number
EP0572881B1
EP0572881B1 EP93108316A EP93108316A EP0572881B1 EP 0572881 B1 EP0572881 B1 EP 0572881B1 EP 93108316 A EP93108316 A EP 93108316A EP 93108316 A EP93108316 A EP 93108316A EP 0572881 B1 EP0572881 B1 EP 0572881B1
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EP
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Prior art keywords
radical
fatty amine
acid
dicarboxylic acid
water
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Expired - Lifetime
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EP93108316A
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German (de)
English (en)
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EP0572881A1 (fr
Inventor
Rainer Kupfer
Martin Hille
Roland Böhm
Friedrich Staiss
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Clariant Produkte Deutschland GmbH
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Hoechst AG
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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
    • C10G33/00—Dewatering or demulsification of hydrocarbon oils
    • C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means

Definitions

  • the invention relates to a method for separating water-in-oil type petroleum emulsions using ester products.
  • oil extraction leads to a watering down of the oil.
  • the water that is conveyed forms a water-in-oil emulsion with the oil.
  • Salts such as sodium chloride, calcium chloride and / or magnesium chloride can be dissolved in the emulsified water.
  • the emulsion water must be separated before the oil is transported to the refinery. In the refinery, before the distillation, the salt content is further reduced by renewed emulsion formation with fresh water and demulsification. Too high a salt content in the crude oil could lead to malfunctions and corrosion in the refinery.
  • a petroleum splitter also called a demulsifier or emulsion splitter, has the task of breaking the emulsion in the lowest possible concentration and, in this separation process, as far as possible without water or with minimal additional use of heat, and to achieve a complete water separation and to reduce the salt content to a minimum.
  • the quality criteria for delivered crude oil are the residual salt and the water content.
  • the crude oils have different compositions depending on their provenance.
  • the natural emulsion stabilizers have a complex, differentiated chemical Construction.
  • selective splitters have to be developed.
  • the different requirements for a petroleum splitter become even more diverse due to different production and processing conditions. Due to the constant opening up of new oil fields and the change in the production conditions of older oil fields, the development of optimal demulsifiers remains an acute problem, and a large number of different types of demulsifiers and demulsifier mixtures are required.
  • esterification products from an oxyalkylated primary fatty amine (as the sole component which supplies OH groups) and a dicarboxylic acid are also very effective petroleum splitters and that this is particularly the case when the esterification product consists of an oxyalkylated primary fatty amine and a dicarboxylic acid the group of dimeric (dimerized) fatty acids.
  • the process according to the invention for separating petroleum emulsions of the water-in-oil type is accordingly characterized in that the emulsions are treated with an effective amount of an esterification product from an oxyalkylated primary fatty amine of the formula 1 below in which R 1 is an alkyl radical or alkenyl radical with 6 to 23 C atoms, R 2 is H or CH 3 and within the chain of the polyoxalkylene radical, arranged in blocks or randomly, can also take on both meanings, and a and b are numbers of 2 in total to 30, with the proviso that neither a nor b is zero, and 0.5 to 1.5 moles per mole of oxyalkylated primary fatty amine, preferably 0.5 to 1.1 moles per mole of oxyalkylated primary fatty amine, of a dicarboxylic acid, preferably one from the group of dimeric fatty acids.
  • R 1 is an alkyl radical or alkenyl radical with 6 to 23 C atoms
  • ester products would also be suitable as demulsifiers for any emulsion or even water-in-oil petroleum emulsions, and the preferred esterification products according to the invention (that is, those of an oxyalkylated primary fatty amine and a dimeric fatty acid as Dicarboxylic acid components) are not even mentioned in the two documents, they should rather be regarded as new.
  • R 1 is a Is an alkyl radical with 8 to 18 carbon atoms or an alkenyl radical with 8 to 18 carbon atoms (it preferably contains 1 to 3 double bonds)
  • R 2 is H and a and b (identical or different, whole or fractional) numbers totaling 2 to 15, taking into account the above-mentioned requirement.
  • the oxyalkylation of primary fatty amines is well known and can be carried out by one of the methods for the oxyalkylation of compounds bearing acidic (active) H atoms.
  • the oxyalkylated fatty amines can contain units of ethylene oxide or propylene oxide or units of ethylene oxide and propylene oxide which are present in random or block form, preference being given to the ethoxylated primary fatty amines, ie those containing only ethylene oxide units.
  • the fatty amines used for the oxalkylation can be individual primary fatty amines or mixtures thereof.
  • fatty amines whose hydrocarbon chain contains one or more double bonds, such as the residues of oleic, linoleic or linolenic acid.
  • the preferred primary fatty amines are the technically available products such as stearylamine, coconut fatty amine or tallow fatty amine (in these technical products there are alkyl residues with essentially 8 to 18 carbon atoms).
  • Preferred dicarboxylic acids are those of formula 2 below (these are simple dicarboxylic acids) HOOC-R 3 -COOH wherein R 3 is an alkylene radical of the formula - (CH 2 ) z -, in which z is an integer from 1 to 10, preferably 4 to 8, and wherein the alkylene radical has 1 or 2 OH groups or 1 or 2 C.
  • 1 to C 18 alkyl or C 3 to C 18 alkenyl may be substituted, or is a vinylene radical or a p-phenylene radical, and those of formula 3 below (these are dicarboxylic acids from the group of dimerized unsaturated C 18 fatty acids) HOOC-R 4 -COOH where R 4 is a divalent hydrocarbon radical with 34 C atoms (R 4 thus represents the radical containing 34 C atoms which is formed when an unsaturated fatty acid with 18 C atoms is dimerized to a dicarboxylic acid with a total of 36 C atoms).
  • malonic acid succinic acid, glutaric acid, adipic acid, pimelic acid and so on may be mentioned in the homologous series, furthermore tartronic acid, malic acid and tartaric acid as well as fumaric acid and maleic acid and finally terephthalic acid.
  • Particularly preferred simple dicarboxylic acids are those of the homologous series from adipic acid to sebacic acid, furthermore maleic acid, fumaric acid, dodecylsuccinic acid and dodecenylsuccinic acid. It goes without saying that instead of these dicarboxylic acids, their anhydrides, halides or esters of lower alkanols can also be used.
  • Dimeric fatty acids are usually produced by addition polymerization (dimerization) of mono- or polyunsaturated fatty acids.
  • the number of carbon atoms and the structure of the dicarboxylic acids obtained essentially depend on the starting fatty acids and on the reaction conditions during the dimerization.
  • Various types and structures of dimeric fatty acids are commercially available.
  • dimeric fatty acids preferred those which are produced by dimerization of unsaturated C18 fatty acids, for example oleic acid, linoleic acid, linolenic acid or tallow fatty acid (dimerization is known to mean the union of two identical molecules to form a new molecule, the dimer, by addition reaction).
  • the dimerization of C 18 fatty acids is generally carried out at a temperature of 150 to 250 ° C, preferably 180 to 230 ° C, with or without a dimerization catalyst.
  • the dicarboxylic acid obtained (this is the dimeric fatty acid) corresponds to the formula 3 given, where R 4 is the divalent linkage formed in the dimerization of the C 18 fatty acid, which bears the two -COOH groups and has 34 C atoms.
  • R 4 is preferably an acyclic (aliphatic) or a mono- or bicyclic (cycloaliphatic) radical with 34 C atoms.
  • the acyclic radical is usually a branched (substituted) and mono- to trisaturated alkyl radical with 34 carbon atoms.
  • the cycloaliphatic radical generally also has 1 to 3 double bonds.
  • the preferred dimeric fatty acids described are generally a mixture of two or more dicarboxylic acids of the formula 3 with structurally different R 4 radicals.
  • the dicarboxylic acid mixture often has a more or less large content of trimeric fatty acids which have arisen during the dimerization and have not been removed during the working up of the product by distillation.
  • some dimeric fatty acids which are formed in the dimerization of the C 18 fatty acids mentioned are given in terms of formula, the hydrocarbon radical bearing the two -COOH groups being an acyclic, monocyclic or bicyclic radical:
  • dicarboxylic acids ie the simple dicarboxylic acids and the dimeric fatty acids, the latter are preferred; they are generally technical products which are commercially available under the name "dimerized fatty acids” or “dimer fatty acids” and, as already mentioned above, can contain a more or less high proportion of trimerized fatty acids.
  • the esterification of the two reaction components, oxalkylated primary fatty amine and dicarboxylic acid takes place in the ratio of 1 mol fatty amine to 0.5 to 1.5 mol dicarboxylic acid, preferably 0.5 to 1.1 mol dicarboxylic acid.
  • the esterification under polycondensation can be carried out using a higher-boiling inert solvent such as toluene, xylene or technical aromatic cuts or without solvent in the melt and under cover with a protective gas, the procedure in solvents being preferred is.
  • the reflux temperature of the reaction mixture is expediently chosen as the reaction temperature and the water of reaction formed is removed azeotropically.
  • the water of reaction is distilled off directly from the reaction mixture.
  • the reaction temperature is 100 to 220 ° C, preferably 130 to 200 ° C.
  • an alkaline or acidic catalyst is used, as is expedient in esterification reactions, acidic catalysis with, for example, a hydrohalic acid, phosphoric acid, sulfuric acid, sulfonic acid or haloacetic acid as the catalyst being preferred.
  • acidic catalysis with, for example, a hydrohalic acid, phosphoric acid, sulfuric acid, sulfonic acid or haloacetic acid as the catalyst being preferred.
  • the course and the end of the reaction can be checked using the water of reaction formed or by determining the acid number. It is preferred to conduct the reaction to about 90 to 100% conversion, that is, until substantially no more water of reaction is formed.
  • the procedure is preferably such that the two reaction components in the molar ratio indicated, a solvent and acidic esterification catalyst are initially introduced into a reaction vessel and this mixture is stirred at 100 to 220 ° C., preferably 130, while an inert gas is passed through heated to 200 ° C and held at this temperature with continuous discharge of the water formed (azeotropic distillation) until the reaction is complete.
  • the esterification product obtained which generally has an acid number of ⁇ 10, preferably 2 to 8, can be purified from the catalyst used by washing with water and represents the petroleum splitter according to the invention.
  • the reaction time is in the range from 5 to 20 h.
  • These esterification products are yellow to brown colored, more or less viscous liquids. They have a special chemical, especially when a dimerized fatty acid is used Structure on. Since their preparation is preferably carried out in the presence of solvents, they are generally in the form of a concentrated solution (active substance content preferably 60 to 80% by weight).
  • the ester products (polyester) proposed according to the invention are notable for a high demulsifying effect.
  • complete water separation and a reduction in salinity are achieved after a short separation time.
  • raw oils that are specific to the consumption are obtained after a short separation time at the usual processing temperatures. They also have the effect that the separated water is practically free of oil, so that complete oil separation from the separated water and thus good water quality is also achieved.
  • oil splitters a sharp separation between the oil and water phases is also achieved, which is another great advantage.
  • the amount of demulsifier used according to the invention can vary within wide limits. It depends in particular on the type of petroleum and the processing temperature.
  • the effective amount is generally 5 to 100 g per ton, preferably 10 to 50 g per ton.
  • the splitters described are preferably used in solution for the purpose of better dosage and distributability.
  • Water or organic liquids are suitable as solvents, for example alcohols such as methanol, isopropanol and / or butanol, aromatic hydrocarbons such as toluene and / or xylene or commercially available mixtures of higher aromatics.
  • the two reaction components are therefore used in a molar ratio of 1: 1.
  • 205 g of xylene are added as solvent, which is 25% by weight, based on the total weight of the two reaction components.
  • the mixture is heated and kept at a temperature of 130 to 140 ° C. for 2 hours, the reaction components reacting with esterification and the water of reaction distilled off azeotropically.
  • the mixture is kept at a temperature of 160 to 170 ° C. for a further 10 hours.
  • the course and the end of the esterification reaction are followed by determining the acid number.
  • the esterification product obtained with a degree of conversion of 98% is a liquid with a viscosity of 1.1 Pa s.

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  • 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)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Colloid Chemistry (AREA)
  • Electronic Switches (AREA)
  • Glass Compositions (AREA)
  • Surgical Instruments (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)

Claims (5)

  1. Procédé pour séparer des émulsions de pétrole brut du type eau-dans-l'huile, caractérisé en ce que l'on ajoute aux émulsions une quantité efficace d'un produit d'estérification obtenu à partir d'une amine grasse primaire alcoxylée ayant la formule 1 ci-après :
    Figure imgb0009
        dans laquelle R1 est un groupe alkyle ou un groupe alcényle ayant de 6 à 23 atomes de carbone, R2 est H ou CH3 et, à l'intérieur de la chaîne du radical polyalcoxylène, disposé en séquences ou d'une manière statistique, peut aussi prendre les deux significations, et a et b sont des nombres valant en tout de 2 à 30, du moment que ni a ni b n'est nul,
    et de 0,5 à 1,5 moles par mole d'une amine grasse primaire alcoxylée, d'un acide dicarboxylique.
  2. Procédé selon la revendication 1, dans lequel on ajoute un produit d'estérification obtenu à partir d'une amine grasse primaire alcoxylée et de 0,5 à 1,5 moles, par mole d'une amine grasse, d'un acide dicarboxylique ayant la formule 2 ci-après :

            HOOC-R3-COOH

       où R3 est un radical alkylène de formule -(CH2)z-, où z est un nombre entier de 1 à 10 et où le radical alkylène peut être substitué par un ou deux groupes OH ou par 1 ou 2 groupes alkyle en C1-C18 ou alcényle en C3-C18, ou encore est un radical vinylène ou p-phénylène,
    ou d'un acide dicarboxylique du groupe des acides gras dimères.
  3. Procédé selon la revendication 1, dans lequel on ajoute un produit d'estérification obtenu à partir de l'amine grasse primaire alcoxylée et de 0,5 à 1,5 moles, par mole de l'amine grasse, d'un acide dicarboxylique choisi dans le groupe des acides gras dimères ayant la formule 3 ci-après

            HOOC-R4-COOH

       dans laquelle R4 est un radical hydrocarboné divalent ayant 34 atomes de carbone.
  4. Procédé selon la revendication 2 ou 3, dans lequel on utilise une amine grasse primaire alcoxylée de formule 1 selon la revendication 1, dans laquelle R1 est un groupe alkyle ayant de 8 à 18 atomes de carbone ou un groupe alcényle ayant de 8 à 18 atomes de carbone, R2 est H, et a et b sont des nombres valant en tout de 2 à 15.
  5. Procédé selon l'une des revendications 1 à 4, dans lequel le produit d'estérification est formé à partir de 0,5 à 1,1 moles d'acide dicarboxylique par mole d'amine grasse.
EP93108316A 1992-05-30 1993-05-22 Procédé de séparation d'émulsions de pétrole du type eau dans l'huile Expired - Lifetime EP0572881B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4217985 1992-05-30
DE4217985A DE4217985A1 (de) 1992-05-30 1992-05-30 Verfahren zum Trennen von Erdölemulsionen vom Wasser-in-Öl-Typ

Publications (2)

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EP0572881A1 EP0572881A1 (fr) 1993-12-08
EP0572881B1 true EP0572881B1 (fr) 1997-08-20

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US (1) US5385674A (fr)
EP (1) EP0572881B1 (fr)
JP (1) JP3499900B2 (fr)
AT (1) ATE157116T1 (fr)
BR (1) BR9302096A (fr)
DE (2) DE4217985A1 (fr)
DK (1) DK0572881T3 (fr)
EG (1) EG20364A (fr)
MX (1) MX9303169A (fr)
MY (1) MY107782A (fr)
NO (1) NO304797B1 (fr)
RU (1) RU2105788C1 (fr)

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US9228089B2 (en) 2010-12-28 2016-01-05 Akzo Nobel Chemicals International B.V. Polyester polyamine and polyester polyquaternary ammonium corrosion inhibitors

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DE19524127A1 (de) * 1995-07-03 1997-01-09 Huels Chemische Werke Ag Amphiphile Verbindungen mit mehreren hydrophilen und hydrophoben Gruppen auf der Basis von alkoxylierten Aminen und/oder Amiden und Di-, Oligo- oder Polycarbonsäuren
US5817155A (en) * 1996-08-08 1998-10-06 Shiseido Co., Ltd. Emulsion for hair treatment
WO2003063790A2 (fr) * 2002-01-31 2003-08-07 Croda, Inc. Additifs et produits contenant des oligoesters
DE102005028500A1 (de) * 2005-06-17 2006-12-28 Basf Ag Aminocarbonsäureester mit EO/PO/BuO-Blockpolymersisaten und deren Verwendung als Emulsionsspalter
CN101421376B (zh) * 2006-04-07 2013-09-18 阿克佐诺贝尔股份有限公司 环境友好的油/水破乳剂
EA026467B1 (ru) 2009-07-03 2017-04-28 Акцо Нобель Кемикалз Интернэшнл Б.В. Полимерные ингибиторы коррозии
EP2611889B1 (fr) 2010-08-30 2014-11-26 Akzo Nobel Chemicals International B.V. Utilisation de polyamines de polyester et de polyester d'ammonium polyquaternaire comme inhibiteurs de la corrosion
US8697615B2 (en) * 2010-12-14 2014-04-15 Nalco Company Polyepihalohydrin reverse emulsion breakers
WO2013092440A1 (fr) 2011-12-19 2013-06-27 Akzo Nobel Chemicals International B.V. Compositions comprenant des inhibiteurs de corrosion de polyamine de polyester et d'ammonium polyquaternaire de polyester et des agents de chélation
RU2652712C1 (ru) * 2017-08-28 2018-04-28 Общество С Ограниченной Ответственностью "Ника-Петротэк" Деэмульгирующая композиция и способ ее использования
AU2022323589B2 (en) 2021-08-05 2025-11-20 Clariant International Ltd Use of complex polyester amines and polyester quaternary ammonium compounds as corrosion inhibitors
US11845892B2 (en) 2021-08-05 2023-12-19 Clariant International Ltd Use of complex polyesteramines and polyester polyquaternary ammonium compounds as corrosion inhibitors

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DE3007930A1 (de) * 1980-03-01 1981-09-24 Henkel KGaA, 4000 Düsseldorf Neue polyesterverbindungen, ein verfahren zu ihrer herstellung und ihre verwendung als textilweichmacher
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Publication number Priority date Publication date Assignee Title
US9228089B2 (en) 2010-12-28 2016-01-05 Akzo Nobel Chemicals International B.V. Polyester polyamine and polyester polyquaternary ammonium corrosion inhibitors

Also Published As

Publication number Publication date
DE59307148D1 (de) 1997-09-25
JP3499900B2 (ja) 2004-02-23
ATE157116T1 (de) 1997-09-15
NO931975L (no) 1993-12-01
MY107782A (en) 1996-06-15
US5385674A (en) 1995-01-31
DE4217985A1 (de) 1993-12-02
EP0572881A1 (fr) 1993-12-08
NO931975D0 (no) 1993-05-28
BR9302096A (pt) 1993-12-07
NO304797B1 (no) 1999-02-15
MX9303169A (es) 1993-12-01
RU2105788C1 (ru) 1998-02-27
EG20364A (en) 1999-01-31
DK0572881T3 (da) 1998-03-23
JPH06128558A (ja) 1994-05-10

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