WO1998001411A2 - Procede de production d'acide acrylique et d'acide methacrylique - Google Patents

Procede de production d'acide acrylique et d'acide methacrylique Download PDF

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Publication number
WO1998001411A2
WO1998001411A2 PCT/EP1997/003629 EP9703629W WO9801411A2 WO 1998001411 A2 WO1998001411 A2 WO 1998001411A2 EP 9703629 W EP9703629 W EP 9703629W WO 9801411 A2 WO9801411 A2 WO 9801411A2
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WO
WIPO (PCT)
Prior art keywords
acrylic acid
acid
solvent mixture
mixture
solvent
Prior art date
Application number
PCT/EP1997/003629
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German (de)
English (en)
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WO1998001411A3 (fr
Inventor
Otto Machhammer
Gerhard Nestler
Original Assignee
Basf Aktiengesellschaft
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Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to EP97936631A priority Critical patent/EP0923523A2/fr
Priority to JP10504806A priority patent/JP2000514076A/ja
Priority to BR9710231A priority patent/BR9710231A/pt
Publication of WO1998001411A2 publication Critical patent/WO1998001411A2/fr
Publication of WO1998001411A3 publication Critical patent/WO1998001411A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/04—Acrylic acid; Methacrylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • the present invention relates to a process for the production of acrylic acid and methacrylic acid.
  • Acrylic acid and methacrylic acid are important basic chemicals. Because of their highly reactive double bond and the acid function, they are particularly suitable as monomers for the preparation of polymers. The greater part of the amount of acrylic acid monomers produced is used before the polymerization - e.g. Adhesives, dispersions or paints - esterified. Only the smaller part of the acrylic acid monomers produced is used directly - e.g. "Superabsorbers" - polymerized. While monomers of high purity are generally required in the direct polymerization of acrylic acid, the requirements for the purity of acrylic acid are not so high when it is esterified.
  • acrylic acid can be prepared in two stages via acrolein by heterogeneously catalyzed gas phase oxidation of propene with molecular oxygen on catalysts in the solid state of aggregation at temperatures between 200 and 400 ° C (cf., for example, DE-A-1 962 431, DE- A-2 943 707, DE-C-1 205 502, DE-A-195 08 558, EP-A-0 257 565, EP-A-0 253 409, DE-A-2 251 364, EP-A- 0 117 146, GB-B-1 450 986 and EP-A-0 293 224).
  • oxidic multi-component catalysts for example based on oxides of the elements molybdenum, bismuth and iron (in the first stage), or molybdenum and vanadium (in the second stage).
  • this amount of solid can be reduced by adding a polar solvent, such as dimethyl phthalate, to the relatively non-polar solvent mixture of diphenyl ether and diphenyl (diphenyl) in one Adds an amount of 0.1 to 25% by weight, which is disadvantageous because of the relatively low Se selectivity of the solvent used with regard to acetic acid and acrylic acid in the absorption in the subsequent work-up steps, a high distillation and therefore expensive separation effort is required. This is associated with a high thermal load on acrylic acid, which leads to product losses due to oligomer and polymer formation.
  • a polar solvent such as dimethyl phthalate
  • EP-A-0 551 111 the mixture of acrylic acid and by-products produced by means of catalytic gas phase oxidation is brought into contact with water in an absorption tower and the aqueous solution obtained is distilled in the presence of a solvent which forms an azeotrope with polar low boilers such as water or acetic acid .
  • DE-C-2 323 328 describes the separation of acrylic acid from an aqueous butanol-acrylic acid esterification liquor by extraction with a special mixture of organic solvents.
  • Acrylic acid purified in this way is suitable, for example, for the production of "superabsorbers".
  • esterification of acrylic acid the corresponding acetates are formed from the acetic acid, which must be separated off by distillation. Under the strongly acidic esterification conditions, the aldehydes lead to resinification products that contaminate the plant.
  • EP-A-0 071 293 describes the selective absorption of carboxylic acids, for example (meth) acrylic acid, from streams containing formic acid, acetic acid and propionic acid with the aid of lactams, for example N-methyl-2-pyrrolidone.
  • BE 694 209 relates to the separation of acrylic acid or methacrylic acid from aqueous solutions containing this acid, which are obtained, for example, directly by oxidation of propene or isobutene after washing with water, by extraction with lactams, which are determined on the N atom with certain C 6 - to C 2 o-containing hydrocarbon radicals are substituted. Ethers or esters can be added to these lactams, for example pyrrolidones. It is disadvantageous that it is difficult to technically separate the (meth) acrylic acid from the pyrrolidones by distillation, as is also shown below in the examples.
  • a solvent mixture of a lactam with a polar organic solvent is much better Selectivity towards alkanoic acids, such as acetic acid, propionic acid, and alkene acids, such as acrylic acid or methacrylic acid, in the absorption than the solvents (mixtures) used hitherto. Because of the lower boiling temperature of the new solvent mixture, the acrylic acid or methacrylic acid is also thermally less stressed during the distillation.
  • the invention thus relates to a process for the preparation of acrylic acid and / or methacrylic acid, which comprises the following steps:
  • Fig. 1 shows a process scheme for the production of acrylic acid according to a preferred embodiment of the invention
  • Fig. 2 is a graphical representation of the acrylic acid removal rate against the distillate fraction for various solvent mixtures according to the
  • a gaseous product mixture which essentially comprises the composition of a reaction mixture for the catalytic gas phase oxidation of C 3 - or C 4 -alkanes, -alkenes, -alkanols and / or - alkanals and / or precursors thereof to acrylic acid or Has methacrylic acid.
  • the gaseous product mixture is particularly advantageously prepared by catalytic gas phase oxidation of propene, acrolein, tert-butanol, isobutene, isobutane, isobutyraldehyde, methacrolein, isobutyric acid or methyl tert-butyl ether.
  • All precursors of the compounds mentioned can be used as starting compounds, in which the actual C 3 - / C 4 starting compound only forms intermediately during the gas phase oxidation.
  • Examples of the production of methacrylic acid are methyl tert-butyl ether or isobutyric acid.
  • the catalytic gas phase reaction of propene and / or acrolein to acrylic acid with molecular oxygen by means of known processes is particularly advantageous, in particular as described in the publications mentioned above.
  • the process is preferably carried out at temperatures between 200 and 450 ° C. and, if appropriate, increased pressure.
  • heterogeneous catalysts oxidic multi-component catalysts based on the oxides of molybdenum, bismuth and iron in the 1st stage (oxidation of propene to acrolein) and the oxides of molybdenum and vanadium in the 2nd stage (oxidation of acrolein to acrylic acid).
  • propane can be converted to a propene / propane mixture by: catalytic oxide hydrogenation, such as. Described, for example, in Catalysis Today 24 (1995), 307-313 or US-A-5 510 558; by homogeneous oxide dehydrogenation, such as. Described in CN-A-1 105 352; or by catalytic dehydrogenation, such as. As described in EP-A-0 253 409, EP-A-0 293 224 or EP-A-0 117 146. When using a propene / propane mixture, propane acts as a diluent.
  • catalytic oxide hydrogenation such as. Described, for example, in Catalysis Today 24 (1995), 307-313 or US-A-5 510 558
  • homogeneous oxide dehydrogenation such as. Described in CN-A-1 105 352
  • catalytic dehydrogenation such as.
  • propane acts as a diluent.
  • Suitable propene / propane mixtures are also refinery propene (70% propene and 30% propane) or cracker propene (95% propene and 5% propane).
  • propene / propane mixtures such as those mentioned above can be oxidized to acrolein and acrylic acid using oxygen or air or a mixture of oxygen and nitrogen of any composition.
  • the conversion of propene to acrylic acid is very exothermic.
  • the reaction gas which contains in addition to the reactants and products advantageously an inert diluent gas, for example recycle gas (see below), atmospheric nitrogen, one or more saturated C j -CG-hydrocarbons, especially methane and / or propane and / or water vapor, can therefore only a absorb a small part of the heat of reaction.
  • an inert diluent gas for example recycle gas (see below)
  • one or more saturated C j -CG-hydrocarbons especially methane and / or propane and / or water vapor
  • the type of reactors used is not limited per se, shell-and-tube heat exchangers that are filled with the oxidation catalyst are mostly used, since the majority of the heat released during the reaction can be dissipated to the cooled tube walls by convection and radiation.
  • the catalytic gas phase oxidation it is not pure acrylic acid that is obtained, but a gaseous mixture which, in addition to acrylic acid as secondary components, essentially unreacted acrolein and / or propene, water vapor, carbon monoxide, carbon dioxide, nitrogen, propane, oxygen, acetic acid, propionic acid, formaldehyde , may contain further aldehydes and maleic anhydride.
  • the reaction product mixture usually contains, based on the entire reaction mixture, 1 to 30% by weight of acrylic acid, 0.05 to 1% by weight of propene and 0.05 to 1% by weight of acrolein, 0.05 to 10% by weight.
  • Oxygen 0.05 to 2% by weight acetic acid, 0.01 to 2% by weight propionic acid, 0.05 to 1% by weight formaldehyde, 0.05 to 2% by weight aldehydes, 0.01 up to 0.5% by weight of maleic anhydride and 20 to 98% by weight, preferably 50 to 98% by weight, of inert diluent gases.
  • Inert diluent gases are, in particular, saturated C r C 6 hydrocarbons, such as 0 to 90% by weight of methane and / or propane, in addition 1 to 30% by weight of water vapor, 0.05 to 15% by weight of carbon oxides and 0 to 90 wt .-% nitrogen, each based on 100 wt .-% diluent.
  • saturated C r C 6 hydrocarbons such as 0 to 90% by weight of methane and / or propane, in addition 1 to 30% by weight of water vapor, 0.05 to 15% by weight of carbon oxides and 0 to 90 wt .-% nitrogen, each based on 100 wt .-% diluent.
  • methacrylic acid can be prepared by catalytic gas phase reaction of C 4 starting compounds with molecular oxygen.
  • the methacrylic acid for. B. by catalytic gas phase oxidation of isobutene, isobutane, tert-butanol, isobutyraldehyde, methacrolein or methyl tert-butyl ether.
  • Transition-metallic mixed oxide catalysts e.g. Mo, V, W and / or Fe are also used as catalysts.
  • Particularly suitable processes are those in which the preparation takes place starting from methacrolein, in particular when the methacrolein is oxidized by gas-phase catalysis of tert-butanol, isobutane or isobutene or by reacting formaldehyde with propionaldehyde according to EP-B-0 092 097 or EP-B-0 058 927 is generated.
  • methacrylic acid in two stages by (1) condensation of propionaldehyde with formaldehyde (in the presence of a secondary amine as catalyst) to methacrylic acid and (2) subsequent oxidation of methacrolein to methacrylic acid.
  • step (b) the acrylic acid and some of the secondary components are separated from the reaction gas (reaction product) by absorption with a solvent mixture.
  • suitable solvent mixtures are high-boiling solvent mixtures composed of at least one lactam which is dissolved in at least one polar organic solvent.
  • the lactams used advantageously have a maximum boiling point of 280 ° C. and preferably a ring size of 5 to 7 atoms.
  • These are in particular pyrrolidones and piperidones which are alkyl-substituted on the nitrogen, the alkyl group preferably containing 1 to 4 carbon atoms, for example N-methylpyrrolidone or N-ethylpyrrolidone.
  • N-methylpyrrolidone Most preferred is N-methylpyrrolidone. Expediently, only a liquid phase is present under the process conditions after absorption.
  • All polar organic solvents with a boiling point of up to 280 ° C. are suitable as polar organic solvents. These are expediently selected from carboxylic acids, preferably C r C 10 carboxylic acids, C 10 -C 10 alcohols, C j -C ⁇ aldehydes, C j - C j o-ketones and mixtures thereof, it being possible for the compounds mentioned to be substituted , in particular with C j -Cg alkyl substituents.
  • Most preferred as the polar organic solvent is ethylhexanoic acid.
  • a mixture of ethylhexanoic acid with N-methylpyrrolidone is therefore expediently used as the solvent mixture.
  • the solvent mixture advantageously contains 3 to 90% by weight, preferably 5 to 25% by weight, in particular 5 to 15% by weight, lactam and 10 to 97% by weight, preferably 75 to 95% by weight, in particular 85 to 95% by weight, polar organic solvent.
  • the ratio of the two mass flows of (to be separated, the acid-containing) reaction gas to the solvent mixture is 0.1: 1 to 10: 1, in particular 1: 1 to 5: 1.
  • the terms high and low boilers, medium boilers and low boilers refer to compounds which have a higher boiling point than acrylic acid (high boilers) or those which have approximately the same boiling point as acrylic acid (middle boilers) or those which have a lower boiling point than acrylic acid (low boilers).
  • the hot reaction gas obtained from stage (a) is cooled by partial evaporation of the solvent mixture in a suitable apparatus, for example a direct condenser or quench apparatus, before absorption. Venturi scrubbers, bubble columns or spray condensers are suitable for this.
  • the high-boiling secondary components of the reaction gas from stage (a) condense into the unevaporated solvent mixture.
  • the partial evaporation of the solvent mixture is also a cleaning step for the solvent mixture.
  • a partial stream of the unevaporated solvent mixture preferably 1 to 10% of the mass stream fed to the absorption column, is drawn off and subjected to solvent cleaning.
  • the solvent mixture is distilled over and the high-boiling secondary components remain, which - if necessary further thickened - can be disposed of, for example burned. This solvent distillation is used to avoid an excessive concentration of high boilers in the solvent stream.
  • the absorption is preferably carried out as countercurrent absorption.
  • the absorption column is preferably equipped with valve or dual flow trays or with packed beds or with ordered or unordered packings, and is charged with (non-evaporated) solvent mixture from above.
  • the gaseous reaction product and any evaporated solvent mixture are introduced into the column from below and then cooled to the absorption temperature.
  • the cooling is advantageously carried out by cooling circuits, ie heated solvent mixture is drawn off from the column, cooled in heat exchangers and fed back to the column at a point above the point of withdrawal.
  • acrylic acid, light, heavy and medium-boiling secondary components and evaporated solvent mixture condense in these solvent cooling circuits. As soon as the reaction gas stream has cooled to the absorption temperature, the actual absorption takes place. The rest of the acrylic acid remaining in the reaction gas is absorbed and part of the low-boiling secondary components.
  • the remaining, non-absorbed reaction gas from stage (a) is further cooled in order to separate off the condensable part of the low-boiling secondary components thereof, in particular water, formaldehyde and acetic acid, by condensation.
  • This condensate is called acid water in the following.
  • the remaining gas stream hereinafter referred to as circulating gas, consists predominantly of nitrogen, carbon oxides and unreacted starting materials. This is preferably partly fed back to the reaction stages as a diluent gas.
  • a solvent stream laden with acrylic acid, heavy and medium-boiling secondary components and a small proportion of low-boiling secondary components is withdrawn from the bottom of the column used in stage (b) and subjected to the distillation in stage (c).
  • the acrylic acid is separated from the solvent mixture together with the medium-boiling components and the last residue of low-boiling secondary components.
  • This separation takes place by means of distillation, in principle any distillation column can be used.
  • the acrylic acid is freely distilled from the solvent mixture and the medium-boiling secondary components, such as maleic anhydride.
  • the distillation is preferably carried out at a temperature of 120 to 200 ° C., in particular between 140 to 170 ° C, at a head pressure of 20 to 600 mbar, in particular 50 to 200 mbar.
  • the buoyancy part of the column is advantageously lengthened and the acrylic acid is withdrawn from the column as a side draw. This acrylic acid is called crude acrylic acid, regardless of its purity.
  • the crude acrylic acid obtained in step (c) contains 98 to 99.8% by weight of acrylic acid and 0.2 to 2% by weight of impurities such as e.g. Acetic acid, aldehydes and maleic anhydride.
  • This acrylic acid can already be used for esterification or can be further purified, e.g. by crystallization.
  • the process according to the invention has the advantage that, owing to the very good selectivity of the solvent mixture used in stage (b) with respect to alkanoic acids, such as acetic acid, propionic acid, and the alkene acids, such as acrylic acid, methacrylic acid, a very good separation of acrylic acid from the secondary components is already in the absorption step , in particular acetic acid and propionic acid, can take place.
  • alkanoic acids such as acetic acid, propionic acid
  • the alkene acids such as acrylic acid, methacrylic acid
  • a very good separation of acrylic acid from the secondary components is already in the absorption step , in particular acetic acid and propionic acid, can take place.
  • the lower boiling point of the solvent mixture used according to the invention for example boiling point of N-methylpyrroiidone 204 ° C., ethylhexanoic acid 228 ° C.
  • the acrylic acid in the distillation column is subjected to significantly less thermal stress. This negates the negative consequences of a high thermal Stress, namely the formation of duners, oligomers or polymers, is greatly reduced.
  • the process according to the invention enables absorptive separation with subsequent distillative separation of propionic acid and acrylic acid.
  • FIG. 1 shows a process diagram for the production of acrylic acid according to a preferred embodiment of the invention.
  • the reference numerals 1 to 12 denote process stages
  • the reference numerals 20 to 31 denote lines
  • K9, K10, K19, K20 and K30 denote apparatuses or apparatus parts.
  • cycle gas compression 1 which essentially consists of nitrogen, carbon oxides and unreacted starting materials and is fed via line 20 to the cycle gas compression 1, this is carried out via line 21 together with propene from line 22 and air Line 23 fed to synthesis 2. This is where the heterogeneously catalyzed two-stage oxidation to acrylic acid takes place.
  • the resulting hot, gaseous reaction product containing the acrylic acid is fed via line 24 to the direct condenser K9 and cooled there by partial evaporation of a solvent mixture of lactam, for example N-methylpyrrolidone, with organic polar solvent, for example ethylhexanoic acid, before absorption.
  • a solvent mixture of lactam for example N-methylpyrrolidone
  • organic polar solvent for example ethylhexanoic acid
  • the solvent mixture loaded with acrylic acid and secondary components is drawn off from the bottom of the column KIO and via line 28 to the distillation column K30, which is preferably a sieve plate.
  • column acts, fed.
  • the solvent mixture distillation 6, the medium boiler distillation 7, the low boiler distillation 8, and the patial condensation 9 take place.
  • the high-boiling solvent mixture and the medium-boiling secondary components for example maleic anhydride, condense into the bottom of column K30 and are returned to absorption 4 via line 29.
  • this low-boiling fraction is expediently reduced by further extending the buoyancy part of the column K30 and withdrawing the acrylic acid from the column K30 via a side draw 30.
  • This acrylic acid is called raw acrylic acid.
  • the process steps of the low boiler stripping 10 shown in dashed lines in the desorption column K20, the low boiler wash 11 in the scrubber K19 and the acid water extraction 12 and the lines relating to these process steps are preferably omitted, in contrast to processes in which solvents / mixtures other than those used according to the invention are omitted be used.
  • the invention relates to the use of a solvent mixture of at least one lactam dissolved in at least one polar organic solvent as solvent in the absorption of acrylic acid and / or methacrylic acid from a product mixture which essentially comprises the composition of a reaction mixture of the catalytic gas phase oxidation of C 3 - / C 4 -alkenes, -alkenes, -alkanols and / or -alkanals and / or precursors thereof to acrylic acid or methacrylic acid.
  • EHS ethylhexanoic acid
  • NMP N-methylpyrrolidone
  • the mass ratio ES to ACS characterizing the selectivity is 50.35. This value means a selectivity which is more than four times higher than in Comparative Example 1.
  • the solvent mixture which in this case is drawn off from the bottom of the column after absorption, there are only 0.094% by weight of ES and 0.060% by weight of water in addition to ACS solved.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production d'acide acrylique ou d'acide méthacrylique comportant les étapes suivantes: (a) production d'un produit réactionnel gazeux renfermant de l'acide acrylique ou méthacrylique et ayant essentiellement la composition d'un mélange réactionnel issu de l'oxydation catalytique en phase gazeuse d'alcanes C3-/C4-, d'alcènes, d'alcanols et/ou d'alcanals et/ou de précurseurs de ceux-ci conduisant à la formation de l'acide acrylique ou méthacrylique, (b) absorption du produit réactionnel avec un mélange solvant renfermant au moins un lactame dissous dans au moins un solvant organique polaire, et (c) distillation du mélange solvant chargé du produit réactionnel pour obtenir un acide acrylique brut ou un acide méthacrylique brut et le mélange solvant.
PCT/EP1997/003629 1996-07-10 1997-07-09 Procede de production d'acide acrylique et d'acide methacrylique WO1998001411A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP97936631A EP0923523A2 (fr) 1996-07-10 1997-07-09 Procede de production d'acide acrylique et d'acide methacrylique
JP10504806A JP2000514076A (ja) 1996-07-10 1997-07-09 アクリル酸およびメタクリル酸の製造方法
BR9710231A BR9710231A (pt) 1996-07-10 1997-07-09 Processo para a preparaçcão de ácdo acrillico ou ácido metacrillico e uso de uma mistura de solventes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19627850A DE19627850A1 (de) 1996-07-10 1996-07-10 Verfahren zur Herstellung von Acrylsäure und Methacrylsäure
DE19627850.3 1996-07-10

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WO1998001411A2 true WO1998001411A2 (fr) 1998-01-15
WO1998001411A3 WO1998001411A3 (fr) 1998-06-25

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EP (1) EP0923523A2 (fr)
JP (1) JP2000514076A (fr)
KR (1) KR20000023679A (fr)
CN (1) CN1227537A (fr)
BR (1) BR9710231A (fr)
CA (1) CA2259994A1 (fr)
DE (1) DE19627850A1 (fr)
ID (1) ID18425A (fr)
WO (1) WO1998001411A2 (fr)

Families Citing this family (15)

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US6180827B1 (en) * 1998-02-03 2001-01-30 Hfm International, Inc. Recovery of acrylic acid from process or waste water streams
FR2798382B1 (fr) * 1999-09-14 2001-10-26 Atofina Procede de purification de l'acide acrylique obtenu par oxydation du propylene et/ou de l'acroleine
US20030150705A1 (en) * 2002-01-08 2003-08-14 Deshpande Sanjeev D. Acrylic acid recovery utilizing ethyl acrylate and selected co-solvents
US20040104108A1 (en) 2002-12-03 2004-06-03 Mason Robert Michael High capacity purification of thermally unstable compounds
WO2011000808A2 (fr) 2009-07-01 2011-01-06 Basf Se Procédé de séparation de l'acide acrylique contenu dans le mélange gazeux produit résultant d'une oxydation en phase gazeuse partielle en catalyse hétérogène d'au moins un composé précurseur c3
DE102010001228A1 (de) 2010-01-26 2011-02-17 Basf Se Verfahren der Abtrennung von Acrylsäure aus dem Produktgasgemisch einer heterogen katalysierten partiellen Gasphasenoxidation wenigstens einer C3-Vorläuferverbindung
DE102009027401A1 (de) 2009-07-01 2010-02-18 Basf Se Verfahren der Abtrennung von Acrylsäure aus dem Produktgasgemisch einer heterogen katalysierten partiellen Gasphasenoxidation wenigstens einer C3-Vorläuferverbindung
DE102010042216A1 (de) 2010-10-08 2011-06-09 Basf Se Verfahren zur Hemmung der unerwünschten radikalischen Polymerisation von in einer flüssigen Phase P befindlicher Acrylsäure
JP5765863B2 (ja) * 2011-03-11 2015-08-19 エルジー・ケム・リミテッド （メタ）アクリル酸の連続回収方法および回収装置
US9822051B2 (en) * 2013-06-03 2017-11-21 Evonik Degussa Gmbh Method for producing acrolein
DE102014017804A1 (de) 2014-12-02 2016-04-21 Basf Se Verfahren zur Herstellung von Acrylsäure
WO2017025391A1 (fr) 2015-08-07 2017-02-16 Basf Se Procédé de fabrication d'acide acrylique
WO2017114831A1 (fr) * 2015-12-29 2017-07-06 Shell Internationale Research Maatschappij B.V. Procédé de conversion d'alcanes et/ou d'alcènes en alcènes et en acides carboxyliques
WO2020020697A1 (fr) 2018-07-26 2020-01-30 Basf Se Procédé pour inhiber la polymérisation radicalaire non souhaitée d'acide acrylique se trouvant dans une phase liquide p
CN115335354A (zh) 2020-03-26 2022-11-11 巴斯夫欧洲公司 抑制存在于液相p中的丙烯酸的不期望的自由基聚合的方法

Citations (2)

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Publication number Priority date Publication date Assignee Title
DE1568081A1 (de) * 1966-02-19 1970-02-05 Basf Ag Verfahren zur Abtrennung von (Meth)acrylsaeure
EP0071293A1 (fr) * 1981-07-24 1983-02-09 Badger B.V. Méthode de séparation d'acides carboxyliques à partir de mélanges contenant des non-acides par un traitement d'absorption et strippage

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1568081A1 (de) * 1966-02-19 1970-02-05 Basf Ag Verfahren zur Abtrennung von (Meth)acrylsaeure
EP0071293A1 (fr) * 1981-07-24 1983-02-09 Badger B.V. Méthode de séparation d'acides carboxyliques à partir de mélanges contenant des non-acides par un traitement d'absorption et strippage

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BR9710231A (pt) 1999-08-10
DE19627850A1 (de) 1998-01-15
KR20000023679A (ko) 2000-04-25
ID18425A (id) 1998-04-09
CA2259994A1 (fr) 1998-01-15
JP2000514076A (ja) 2000-10-24
WO1998001411A3 (fr) 1998-06-25
CN1227537A (zh) 1999-09-01
EP0923523A2 (fr) 1999-06-23

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