WO2009130196A1 - Procédé de séparation d'émulsions huile dans eau au moyen d'au moins des agents complexants bidentés - Google Patents

Procédé de séparation d'émulsions huile dans eau au moyen d'au moins des agents complexants bidentés Download PDF

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Publication number
WO2009130196A1
WO2009130196A1 PCT/EP2009/054703 EP2009054703W WO2009130196A1 WO 2009130196 A1 WO2009130196 A1 WO 2009130196A1 EP 2009054703 W EP2009054703 W EP 2009054703W WO 2009130196 A1 WO2009130196 A1 WO 2009130196A1
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radical
radicals
oil
group
complexing agents
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German (de)
English (en)
Inventor
Marcus Guzmann
Andreas Eichhorn
Frank Rittig
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BASF SE
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BASF SE
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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
    • B01D17/02—Separation of non-miscible liquids
    • B01D17/04—Breaking emulsions
    • B01D17/047—Breaking emulsions with separation aids

Definitions

  • a method for splitting oil-water emulsions using at least bidentate chelating agents using at least bidentate chelating agents
  • the invention relates to a process for splitting oil-water emulsions, in particular oil-water emulsions of asphaltene-rich and / or naphthenic-rich crude oils, using emulsion breakers and at least bidentate complexing agents, preferably complexing agents containing phosphonic acid groups.
  • Oil-water emulsions accumulate in a variety of industrial processes, e.g. in the course of metalworking, in car washes, refineries or in oil production. Such emulsions usually have to be separated for further processing or for proper disposal in the components of oil and water. To accelerate the phase separation, it is known to use emulsion breakers (demulsifiers). Emulsion breakers are surface-active substances that influence the oil-water interfaces and thus contribute to a faster phase separation.
  • Petroleum also usually accumulates during production as a relatively stable water-oil emulsion. Depending on the nature of the deposit as well as the degree of discharge, it may contain up to 95 or even% by weight of water.
  • the water may be, on the one hand, water already contained in the deposit, and, on the other hand, water which is injected into the deposit in the course of secondary and / or tertiary mineral oil production by means of injection bores.
  • larger amounts of salts are dissolved in the water, for example alkali or alkaline earth metal salts, and furthermore the emulsion usually also contains solids which are discharged from the borehole with the oil-water emulsion.
  • the water-oil emulsions are stabilized by natural, occurring in crude emulsifiers such as naphthenic acids or asphaltenes. They may also be additionally stabilized by non-naturally occurring emulsifiers, such as surfactants, which have been introduced into the oil reservoir for tertiary mineral oil production, and are then discharged again with the oil thus promoted.
  • crude emulsifiers such as naphthenic acids or asphaltenes.
  • non-naturally occurring emulsifiers such as surfactants
  • Water, salts and solids must be removed before processing the crude oil in the refinery. Refineries often require that the water content of the delivered crude oil is not more than 1%. For economic reasons, the removal of the water and the other components from the crude oil is still at the place of promotion, to avoid the uneconomic transport of water and to prevent or at least minimize corrosion problems.
  • phase separation of the water-oil emulsion should be possible quickly and as completely as possible. Only in this way, in view of the large delivery volumes, the devices for phase separation, such as settling tanks, kept as small as possible become. On offshore platforms, the use of small, compact phase separation devices is a constructive necessity, given the limited space available, and of course, small systems generally require lower investment costs than large systems. An often asked requirement is that the phase separation should not take more than about 20 to 30 minutes.
  • Asphaltenes are those components of crude oil which precipitate out of crude oil with an excess of heptane but are soluble in benzene. These are polycyclic, aromatic hydrocarbons which additionally include heteroatoms such as N, O and S and are stabilized on their surface with resins.
  • polyvalent metal ions especially iron ions
  • asphaltenes can provide good stabilization of the petroleum-water interface and, accordingly, such emulsions are difficult to separate. Iron ions may naturally occur in the reservoir water or be introduced into the reservoir with the flood medium as part of secondary or tertiary mining operations.
  • Naphthenic acids are carboxylic acids of saturated (poly) cyclic hydrocarbons. Naphthenic acids do not precipitate on addition of heptane to crude oil. Naphthenic acids act as surfactants and can thus stabilize the crude oil-water interface.
  • Demulsifiers for splitting oil-water emulsions are known.
  • EP-A 0 264 841 describes the use of linear copolymers of hydrophobic acrylic or methacrylic acid esters and hydrophilic ethylenically unsaturated monomers as petroleum emulsion breakers.
  • EP-A 0 499 068 describes the preparation of reaction products of vinylic monomers and alcohol or phenol alkoxylates and their use as demulsifiers for crude oil emulsions.
  • EP-A 0 541 018 describes emulsion breakers prepared from polyethyleneimines having a weight-average molecular weight of up to 35,000 g / mol and ethylene oxide and propylene oxide, wherein the second active component additionally employed is an alkylphenol formaldehyde resin.
  • EP-A 0 784 645 describes the preparation of alkoxylates of polyamines, especially of polyethyleneimines and polyvinylamines, and their use as crude oil emulsion breakers.
  • EP-A 0 267 517 discloses branched polyaminoesters as demulsifiers.
  • the branched polyamino esters are obtained by reacting alkoxylated primary amines with triols and dicarboxylic acids.
  • WO 2006/084816 describes the use of hyperbranched polymers as demulsifiers for cracking crude oil emulsions.
  • EP 717 167 A2 discloses the use of glycine-N, N-diacetic acid derivatives as complexing agents for alkaline earth and heavy metal ions in the extraction and transport of crude oil and natural gas. The use for cracking crude oil emulsions is not disclosed.
  • WO 98/14621 discloses aminomethylenephosphonic acid derivatives which are soluble in hydrocarbons for the extraction of metal ions from aqueous solutions. The use of phosphonic acid derivatives for the cleavage of oil-water emulsions is not disclosed.
  • the object of the invention was to provide an improved method for splitting oil-water emulsions, which also achieves good results when splitting emulsions of asphaltene-rich crude oils.
  • the complexing agents are amines which comprise, as substituents, methylenephosphonic acid groups -CR 2 -PO 3 H 2 and hydrocarbon groups having from 6 to 30 carbon atoms.
  • oil-water emulsions in particular oil-water emulsions of asphaltene-rich and / or naphthenic-acid-rich petroleum oils, can be separated particularly well using such complexing agents. More specifically, the following is to be accomplished for the invention:
  • At least one emulsion breaker is used to crack the oil-water emulsion.
  • a mixture of two or more emulsion breakers can be used.
  • Emulsion breakers may be, for example, oxyalkylated phenolformaldehyde resins, EO / PO block copolymers, crosslinked diepoxides, polyamides or their alkoxylates, salts of sulfonic acids or ethyoxlated and / or propoxylated polyethyleneimines or hyperbranched polymers.
  • Suitable hyperbranched polymers for splitting emulsions are disclosed, for example, by WO 2006/084816.
  • At least one at least bidentate complexing agent is used in addition to the emulsion breakers.
  • At least bidentate complexing agents are also known as chelating complexing agents.
  • chelating group is meant in a known manner an at least bidentate group which can bind metal ions and which can occupy at least two coordination sites on the central metal ion in the formation of complexes with metal ions.
  • the chelating groups may preferably be O-atom coordinating groups.
  • O-atom coordinating groups examples include COOH groups as well as in particular phosphoric acid and / or phosphonic acid groups. They are preferably complexing agents comprising phosphonic acid groups.
  • complexing agents comprising COOH groups include ethylenediaminetetraacetic acid (EDTA), hydroxyethylethylenediaminetetraacetic acid, diethylenetriaminepentacetic acid or nitrilotriacetic acid, hydroxyethylenediaminotriacetic acid, methylglycinediacetic acid or ethylenediamine-N, N'-dihydroxyphenylacetic acid.
  • EDTA ethylenediaminetetraacetic acid
  • hydroxyethylethylenediaminetetraacetic acid diethylenetriaminepentacetic acid or nitrilotriacetic acid
  • hydroxyethylenediaminotriacetic acid methylglycinediacetic acid or ethylenediamine-N, N'-dihydroxyphenylacetic acid.
  • preferred complexing agents containing phosphorous or phosphonic acid groups include 1-hydroxyethane- (1, 1-diphosphonic acid), ethylenediaminetetramethylenephosphonic acid, diethylene
  • oil-soluble complexing agents which in addition to the at least bidentate group at least one have hydrophobic group.
  • the hydrophobic groups impart to the complexing agent used according to the invention improved solubility in organic phases, in particular in oil phases.
  • the complexing agents should be miscible indefinitely with non-polar organic solvents.
  • at least the solubility of the complexing agents used according to the invention in 2-propylheptanol at room temperature is at least 50 g / kg, preferably at least 100 g / kg, more preferably at least 200 g / kg and very particularly preferably at least 300 g / kg.
  • the hydrophobic groups are preferably straight-chain, branched, saturated or unsaturated aliphatic and / or aromatic hydrocarbon radicals having 6 to 30 carbon atoms, preferably 6 to 22 carbon atoms. Preference is given to unbranched or branched alkyl radicals having 6 to 30 carbon atoms.
  • the chelating groups and the hydrophobic groups may be linked together directly or via suitable linking groups
  • the complexing agents are amines which comprise, as substituents, methylenephosphonic acid groups -CR 2 -PO 3 H 2 and hydrocarbon groups having from 6 to 30 carbon atoms.
  • Phosphonic acid groups are capable of binding metal ions, and the hydrocarbon groups provide the complexing agents with good solubility in organic phases.
  • the complexing agents used according to the invention may be derivatives of monoamines (I), diamines (II) or polyamines (III). Chelating agents based on monoamines have the general formula (I).
  • R 1 is a straight-chain, branched, saturated or unsaturated aliphatic and / or aromatic hydrocarbon radical having 6 to 30 carbon atoms, preferably 6 to 22 carbon atoms, which may optionally be substituted by an OH group.
  • examples of such radicals include C ⁇ to C30 alkyl, C ⁇ to C30 alkenyl, C ⁇ to C30 aryl or C7 to Cis alkylaryl radicals.
  • Ce- to C3o-alkenyl radicals are, for example, oleyl, linolyl and Linolenylreste.
  • C ⁇ - to C3o-aryl radicals include phenyl or naphthyl radicals and corresponding alkyl-substituted radicals such as toyl or xylyl radicals.
  • C7- to C18-alkylaryl radicals are, for example, in particular C7- to C18-phenylalkyl radicals such as benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 2-phenylprop-2-yl, 4 Phenylbutyl, 2,2-dimethyl-2-phenylethyl, 5-phenylamyl, 10-phenyldecyl, 12-phenyldodecyl. Particularly preferred are benzyl radicals.
  • Alkyl radical particularly preferably a C ⁇ - to C22-alkyl radical and particularly preferably a Cs to C 2o-alkyl radical.
  • alkyl radicals include n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, iso-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, iso-tridecyl, n- Tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicosyl.
  • R 1 is a 2-ethylhexyl radical.
  • R 1 may be a group -CH b -CH (OH) -R 4 , where R 4 is one of a straight-chain, branched, saturated or unsaturated aliphatic and / or aromatic hydrocarbon radical having 4 to 28 carbon atoms, preferably 6 to 20 carbon atoms. R 4 is preferably phenyl or a straight-chain or branched C 1 - to C 20 -alkyl radical.
  • groupings of the formula -CH 2 -CH (OH) -R 4 are derived from long-chain epoxidized ⁇ -olefins, such as, for example, 1,2-epoxyhexane, 1,2-epoxyoctane, 1,2-epoxydecane, 1,2-epoxydodecane, 1, 2-epoxytetradecane, 1, 2-epoxyhexadecane or 1, 2-epoxyoctadecane or styrene oxide.
  • the radical R 2 is a methylenephosphonic acid group -CR 2 -PO 3 H 2 or a salt thereof, it being possible for the radicals R ' independently of one another to be hydrogen or a C 1 - to C 4 -alkyl radical. At least one of the radicals R ' is preferably hydrogen and particularly preferably both are hydrogen, ie R 2 is -CH 2 -PO 3 H 2 or a salt thereof.
  • the radical R 3 is a radical selected from the group of hydrogen, a C 1 to C 1 alkyl radical, R 1 or R 2 .
  • the complexing agents are preferably those of formula (I) to those of the formula (R 1 ⁇ 2 N-CH 2 -PO 3 H 2 or R 1 -N (-CH 2 -PO 3 H 2 ) 2 , more preferably (R 1 -) 2 N-CH 2 -PO 3 H 2 , where R 1 is preferably a 2-ethylhexyl radical, of course, it may also be the corresponding salts, in particular the corresponding alkali metal salts.
  • Diamide-based complexing agents have the general formula (II).
  • R 4 is a straight-chain or branched C 1 - to C 12 -alkylene group, preferably a C 2 - to C 8 -alkylene group and particularly preferably a C 2 - to C 6 -alkylene group.
  • radicals R 4 include methylene, 1,2-ethylene, 1,2-propylene, 1,3-propylene, dimethylmethylene, ethylmethylene, 1,2-butylene, 1,3-butylene, 2,3-butylene, 1, 4-butylene, 1, 5-pentamethylene, 1, 6-hexamethylene and 1, 8-octamethylene. It is preferably 1, 2-ethylene, 1, 2-propylene or 1, 3-propylene and particularly preferably 1, 2-ethylene.
  • R 5 is independently a radical selected from the group of hydrogen, a C 1 to C 1 alkyl radical, R 1 or R 2 , with the proviso that at least one of the radicals R 5 is a radical R 1 and at least one further radical R 5 is a radical R 2 .
  • complexing agents (II) include those of formulas (IIa), (IIb) and (Nc).
  • R 4 has the meaning defined above, wherein the different radicals R 4 in formula (III) may be the same or different.
  • the radicals R 6 are each independently a radical selected from the group of hydrogen, a C 1 to C 1 alkyl radical, R 1 or R 2 .
  • R 7 is a radical selected from the group of hydrogen, a C 1 - to C 6 -alkyl radical, R 1 or R 2 or a radical of the general formula (IV)
  • a radical of the formula (IV) represents a branch, which in turn may itself be branched.
  • indices n around m each have at least the value of 1, the sum of n and m added over all branches being 2 to 30,000.
  • Oligomers with a sum of n + m ⁇ 10 can be linear or branched, while polymers usually have branches.
  • the complexing agents of the formula (III) are at least 50%, preferably at least 60% and particularly preferably at least 75% of all the radicals R 6 and R 7 occurring in the molecule to radicals R 1 and / or R 2 , with the proviso the numerical ratio of hydrocarbon groups R 1 to the methylenephosphonic acid groups R 2 X R VX R 2 is 10: 1 to 1: 2.
  • the ratio X R VX R 2 is preferably 5: 1 to 1: 1 and more preferably 2: 1 to 1: 1.
  • the number of substituents R 1 and R 2 in formula (INI) and their ratio is set by the skilled person depending on the desired properties of the complexing agent in the separation process. Depending on the nature and number of radicals R 1 to R 2 , the egg properties of the complexing agents used rather hydrophilic or rather hydrophobic properties.
  • the preferred complexing agents (I), (II) or (III) can be prepared by customary methods.
  • acid catalysis eg inorganic acids or mineral acids such as sulfuric acid or hydrochloric acid, sulfonic acids such as p-toluenesulfonic acid or methanesulfonic acid or carboxylic acids such as Mixture of acetic acid / acetic anhydride
  • Such reactions of amines with formaldehyde and phosphorous acid are usually at 0 to 15O 0 C, in particular 50 to 120 ° C, especially 80 to 110 ° C, performed.
  • Amine, formaldehyde and phosphorous acid are advantageously used, based on an NH bond, in a molar ratio of 1: (2 to 6) :( 1 to 4).
  • these compounds can also be obtained by hydrolysis of corresponding phosphonic acid esters obtainable by reaction with phosphites instead of phosphorous acid.
  • Another synthetic route which is of interest in particular for the compound with R ' * H, is based on aldehydes (eg of the formula R-CHO) or ketones (eg of the formula R-CO-R) and the corresponding primary amines which give imines be converted to which then phosphorous acid is added.
  • aldehydes eg of the formula R-CHO
  • ketones eg of the formula R-CO-R
  • Oligomeric and polymeric complexing agents of the formula (III) can be obtained in a two-stage reaction by first treating a corresponding oligo- or polyamine, ie a compound (III) in which all radicals R 6 and R 7 are hydrogen, in a first Step treated with an alkylating agent to obtain an oligo- or polyamine modified with groups R 1 .
  • This can be phosphonomethylated in a second stage as already described.
  • Suitable oligo- or polyamines are, in particular, oligo- or polyethylenimines, preferably those having an average molar mass M n of 2,000 to 60,000 g / mol, preferably 4,000 to 40,000 g / mol.
  • the groups R 1 and R 2 are in this case bound statistically by the oligo- and polyamines, ie a mixture of different molecules is not formed, not a specific molecule.
  • the above information on the number and the ratio of the groups R 1 and R 2 each refer to such a mixture.
  • oil-soluble complexing agents are used according to the invention in processes for splitting oil-water emulsions.
  • the oil-water emulsions to be split can be any desired oil-water emulsions, for example emulsions which are obtained in the course of metalworking using metalworking fluids, the wastewaters of car washes, from refineries, chemical-technical processes ,
  • emulsion cleavage is also intended to include deoiling processes, which is understood by one skilled in the art to be the removal of minor amounts of residual oil from water, for example from the aqueous phase, which remains after cleavage of a crude oil-water emulsion.
  • the process according to the invention is preferably used for cracking crude oil emulsions.
  • the crude oil emulsions can be both water-in-oil and oil-in-water emulsions.
  • the crude oil emulsions may contain, for example, from 0.1 to 99% by weight of water or salt water.
  • Crude oil may be crude of any origin. They may preferably be asphaltene-rich and / or naphthenic-acid-rich crude oils. It may in particular be crude oils with an asphaltene content of more than 0.1% by weight, preferably more than 1% by weight and more preferably more than 5% by weight and very particularly preferably more than 10% by weight. Furthermore, it may in particular be crude oils having a naphthenic acid content of more than 0.01% by weight, preferably more than 0.1% by weight and more preferably more than 1% by weight.
  • the emulsion breakers to be used and the complexing agents are preferably added in dissolved or dispersed form.
  • mixtures of different emulsion breakers and / or different complexing agents can be used.
  • aqueous or organic formulations may be used for this purpose.
  • organic solvents include alcohols such as methanol, ethanol, propanol, isopropanol, butanol or i-decanol, paraffinic solvents such as hexane, cyclohexane, heptane, octane, isooctane or benzene fractions, or aromatic solvents such as toluene, xylene or solvent naphtha.
  • Aqueous formulations include water as well as mixtures of water and water-miscible organic solvents such as alcohols.
  • the emulsion breakers and complexing agents may be dissolved together or else preferably used in separate formulations.
  • the concentration of the emulsifier or emulsifiers used, based on the oil content of the crude oil emulsion, is generally 1 ppm to 5000 ppm, preferably 1 ppm to 3000 ppm, more preferably 2 ppm to 1000 ppm and especially 5 ppm to 500 ppm; the information "ppm" refers here in each case to the mass of the crude oil.
  • the concentration of the complexing agent or complexing agents used, based on the oil content of the crude oil emulsion, is generally 1 ppm to 50,000 ppm, preferably 1 ppm to 10,000 ppm, more preferably 2 ppm to 1,000 ppm and especially 5 ppm to 500 ppm; the information "ppm" refers here in each case to the mass of the crude oil.
  • the emulsion splitting is usually carried out locally, i. still on the oil field. It may be a plant on a production well or a central plant in which for several production wells of an oil field together the cleavage of the crude oil emulsions is made.
  • the cleavage takes place already at the temperature of the freshly produced crude oil emulsion at such a rate that the emulsion can already be split on the way to the treatment plant.
  • This broken emulsion is then separated in an optionally heated separator and possibly with the aid of an electric field in pure oil and water or salt water.
  • the separator can be systems which only separate under the influence of gravity, for example settling tanks or even other separators, such as hydrocyclones.
  • the separation of the crude oil emulsion is usually carried out at 10 0 C to 130 0 C, preferably at 20 ° C to 90 0 C and particularly preferably at 40 ° to 90 ° C.

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

Abstract

L'invention concerne un procédé de séparation d'émulsions huile dans eau, en particulier des émulsions huiles dans eau d'huiles brutes riches en asphalte, à l'aide de désémulsionneurs et d'au moins deux agents complexants bidentés, de préférence des agents complexants comportant des groupes d'acide phosphonique.
PCT/EP2009/054703 2008-04-22 2009-04-21 Procédé de séparation d'émulsions huile dans eau au moyen d'au moins des agents complexants bidentés Ceased WO2009130196A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP08154942 2008-04-22
EP08154942.0 2008-04-22
EP08172159 2008-12-18
EP08172159.9 2008-12-18

Publications (1)

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WO2009130196A1 true WO2009130196A1 (fr) 2009-10-29

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9062278B2 (en) 2010-02-19 2015-06-23 Basf Se Preparing ether carboxylates

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3259587A (en) * 1960-08-04 1966-07-05 Petrolite Corp Demulsification
US4938876A (en) * 1989-03-02 1990-07-03 Ohsol Ernest O Method for separating oil and water emulsions
US5080779A (en) * 1990-08-01 1992-01-14 Betz Laboratories, Inc. Methods for removing iron from crude oil in a two-stage desalting system
US6267936B1 (en) * 1996-09-30 2001-07-31 Basf Aktiengesellschaft Method for effecting solvent extraction of metal ions using hydrocarbon soluble aminomethylene phosphonic acid compounds
US20040045875A1 (en) * 2002-08-30 2004-03-11 Nguyen Tran M. Additives to enhance metal and amine removal in refinery desalting processes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3259587A (en) * 1960-08-04 1966-07-05 Petrolite Corp Demulsification
US4938876A (en) * 1989-03-02 1990-07-03 Ohsol Ernest O Method for separating oil and water emulsions
US5080779A (en) * 1990-08-01 1992-01-14 Betz Laboratories, Inc. Methods for removing iron from crude oil in a two-stage desalting system
US6267936B1 (en) * 1996-09-30 2001-07-31 Basf Aktiengesellschaft Method for effecting solvent extraction of metal ions using hydrocarbon soluble aminomethylene phosphonic acid compounds
US20040045875A1 (en) * 2002-08-30 2004-03-11 Nguyen Tran M. Additives to enhance metal and amine removal in refinery desalting processes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9062278B2 (en) 2010-02-19 2015-06-23 Basf Se Preparing ether carboxylates

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