EP1453785A2 - Verfahren zur herstellung von acrylsäure aus propan in abwesenheit von molekularem sauerstoff - Google Patents

Verfahren zur herstellung von acrylsäure aus propan in abwesenheit von molekularem sauerstoff

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Publication number
EP1453785A2
EP1453785A2 EP02799759A EP02799759A EP1453785A2 EP 1453785 A2 EP1453785 A2 EP 1453785A2 EP 02799759 A EP02799759 A EP 02799759A EP 02799759 A EP02799759 A EP 02799759A EP 1453785 A2 EP1453785 A2 EP 1453785A2
Authority
EP
European Patent Office
Prior art keywords
limits included
catalyst
limits
propane
oxygen
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Withdrawn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
EP02799759A
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English (en)
French (fr)
Inventor
Jean-Luc Dubois
Stéphanie SERREAU
Julien Jacquel
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.)
Arkema France SA
Original Assignee
Atofina SA
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
Application filed by Atofina SA filed Critical Atofina SA
Publication of EP1453785A2 publication Critical patent/EP1453785A2/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/20—Vanadium, niobium or tantalum
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/24—Chromium, molybdenum or tungsten
    • B01J23/28—Molybdenum
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
    • B01J23/88—Molybdenum
    • B01J23/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/8876—Arsenic, antimony or bismuth
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
    • B01J23/88—Molybdenum
    • B01J23/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/8877—Vanadium, tantalum, niobium or polonium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
    • B01J27/057—Selenium or tellurium; Compounds thereof
    • B01J27/0576—Tellurium; Compounds thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/19—Catalysts containing parts with different compositions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0236—Drying, e.g. preparing a suspension, adding a soluble salt and drying

Definitions

  • the present invention relates to the production of acrylic acid from propane in the absence of molecular oxygen.
  • This process has the major drawback of producing propionic acid as a by-product.
  • This acid poses problems in certain applications of acrylic acid when it is present in too large a quantity.
  • the invention therefore aims to reduce the production of propionic acid in such a process.
  • the subject of the invention is a process such as that which has just been described but in which the gaseous mixture is also passed over a co-catalyst.
  • a more specific subject of the invention is therefore a process for manufacturing acrylic acid from propane, in which a gaseous mixture devoid of molecular oxygen and comprising propane, steam, as well as , where appropriate, an inert gas, on a catalyst comprising molybdenum, vanadium, tellurium, oxygen and at least one other element X chosen from niobium, tantalum, tungsten, titanium, aluminum , zirconium, chromium, manganese, iron, ruthenium, cobalt, rhodium, nickel, palladium, platinum, antimony, bismuth, boron, indium and cerium, to oxidize propane according to the following redox reaction (1):
  • Such a process therefore makes it possible to greatly reduce the propionic acid / acrylic acid ratio at the outlet of the reactor. In addition, it also decreases the formation of acetone, which is also a by-product of the manufacture of acrylic acid from propane.
  • Another subject of the invention is a solid catalytic composition
  • a solid catalytic composition comprising: a) the catalyst as defined above; as well as b) the co-catalyst as defined above.
  • the co-catalyst used in the process according to the invention corresponds to formula (II) indicated above.
  • the oxides of the different metals used in the composition of the mixed oxide of formula (II) can be used as raw materials in the preparation of this composition, but the raw materials are not limited to oxides; as other raw materials, there may be mentioned: - in the case of molybdenum, ammonium molybdate, ammonium paramolybdate, ammonium heptamolybdate, molybdic acid, molybdenum halides or oxyhalides such as MoCl 5 , organometallic molybdenum compounds such as molybdenum alkoxides such as Mo (OC 2 H 5 ) 5 , acetylacetone molybdenyl; - in the case of vanadium, ammonium metavanadate, vanadium halides or oxyhalides such as VC1 4 , VC1 5 or V
  • VO (OC 2 H 5 ) 3 - in the case of niobium, niobic acid, Nb2 (C204) 5, niobium tartrate, niobium hydrogen oxalate, oxotrioxalatoammonium niobiate ⁇ (NH4) 3 [Nb0 (C204) 3] "l , 5H2 ⁇ , niobium and ammonium oxalate, niobium and tartrate oxalate, halides or oxyhalides of nobium such as NbCl3, EbC15 and organometallic compounds of niobium such as niobium alkoxides such as Nb (0C2H5 ) 5, Nb (0-n-Bu) 5;
  • the silicon source generally consists of colloidal silica.
  • solid compositions of formula (II) can be prepared by mixing, with stirring, aqueous solutions of niobic acid, ammonium heptamolybdate, ammonium metavanadate, telluric acid, preferably adding colloidal silica, then precalcining in air at about 300 ° C and calcining under nitrogen at about 600 ° C.
  • limits included d is between 0.1 and 0.6
  • limits included - e ' is between 0.006 and 0.01
  • the catalyst is such as that used in the process of the above-mentioned European patent application No. 608 838, and in particular, the catalyst of formula M ⁇ V 0 , 3 Te 0 , 23 Nbo, ⁇ O n , the preparation of which is described in Example 1 of this patent application.
  • the catalyst corresponds to the following formula (I):
  • a is between 0.006 and 1
  • limits included b is between 0.006 and 1
  • limits included c is between 0.006 and 1
  • limits included d is between 0 and 3.5, limits included
  • - x is the quantity of oxygen linked to the other elements and depends on their oxidation states,
  • a is between 0.09 and 0.8, limits included
  • Such a catalyst can be prepared in the same way as the co-catalyst of formula (II) and from the same raw materials with, in addition, as tellurium source, tellurium oxide, telluric acid or, of a in general, all the compounds capable of forming a tellurium oxide by calcination, namely, metallic salts of organic acids, metallic salts of mineral acids, complex metallic compounds, etc.
  • the manufacture of acrylic acid is carried out by passing a gaseous mixture lacking of molecular oxygen and comprising propane and water vapor, as well as, if appropriate, an inert gas, on a catalyst and a cocatalyst as defined above, to conduct the reaction redox (1) as indicated above.
  • the mass ratio of the catalyst to the co-catalyst is generally greater than 0.5 and preferably at least 1.
  • the catalyst and the cocatalyst are located in the same reactor.
  • the redox reaction is carried out in a single step.
  • the catalyst and the cocatalyst can be in the form of a solid catalytic composition.
  • They may each be in the form of grains, the grains of catalyst and of cocatalyst being mixed before the implementation of the process according to the invention.
  • the catalyst and the cocatalyst can also be in the form of a solid catalytic composition composed of grains, each of which comprises both the catalyst and the cocatalyst.
  • the redox reaction (1) is carried out at a temperature of 200 to 500 ° C, preferably from 250 to 450 ° C, more preferably still, from 350 to 400 ° C.
  • the pressure is generally from 1.01.10 4 to 1.01.10 e Pa
  • the residence time is generally 0.01 to 90 seconds, preferably 0.1 to 30 seconds.
  • the propane / water vapor volume ratio in the gas phase is not critical and can vary within wide limits.
  • the proportion of inert gas which may be helium, krypton, a mixture of these two gases, or nitrogen, carbon dioxide, etc., is also not critical and may also vary within wide limits.
  • the following ratio (by volume) can be cited: propane / inert (He-Kr) / H 2 0 (vapor): 10-20 / 40-50 / 40-50
  • reaction (2) the regeneration of said solid composition is carried out according to reaction (2):
  • the process is generally carried out until the reduction rate of the solid composition is between
  • the solid composition After the regeneration, which can be carried out under conditions of temperature and pressure identical or different from those of the redox reaction, the solid composition regains initial activity and can be used in a new reaction cycle.
  • the redox reaction (1) and the regeneration can be carried out in a conventional reactor, such as a fixed bed reactor, a fluidized bed reactor or a transported bed reactor.
  • the redox reaction (1) and the regeneration can therefore be carried out in a two-stage device, namely a reactor and a regenerator which operate simultaneously and in which two charges of solid composition alternate periodically; we can also conduct the reaction redox (1) and regeneration in the same reactor by alternating the reaction and regeneration periods.
  • the redox reaction (1) and the regeneration are carried out in a reactor with a transported catalyst bed.
  • the propylene produced as a secondary product and / or the unreacted propane are recycled (or returned) to the inlet of the reactor, that is to say that they are reintroduced to the 'inlet of the reactor, in mixture or in parallel with the starting mixture of propane, water vapor and if necessary inert gas (ies).
  • x is the quantity of oxygen linked to the other elements and depends on their oxidation states.
  • catalyst A of formula Mo_Vo t 3 _Jiibo, ⁇ Teo, z2Sio.9sO x a) Preparation of a niobium solution In a 5 1 beaker, 640 g of distilled water are introduced and then 51.2 g of niobic acid (ie 0, 304 moles of niobium). We then add 103.2 g (0.816 mole) of oxalic acid dihydrate.
  • the oxalic acid / niobium molar ratio is therefore 2.69.
  • Ludox silica containing 40% by weight of silica, supplied by the company Dupont
  • the latter retains its clarity and red coloration.
  • the niobium solution prepared above is then added. A fluorescent orange gel is thus obtained after a few minutes of stirring. This solution is then spray dried.
  • the atomizer used is a laboratory atomizer (ATSELAB from the company Sodeva). The atomization takes place under a nitrogen atmosphere (in order to avoid any oxidation and any untimely combustion of the oxalic acid present in the slip).
  • the operating parameters are overall: - nitrogen flow rate of the order of 45 Nm3 / h; slip flow of the order of 500 g / h; gas inlet temperature between 155 ° C and 170 ° C; gas outlet temperature between 92 ° C and 100 ° C.
  • the recovered product 355.2 g, which has a particle size of less than 40 microns, is then placed in an oven at 130 ° C. overnight in a teflon-coated tray. 331 g of dry product are thus obtained.
  • the precalcinations and calcinations were carried out under air and nitrogen flow in steel capacities. These capacities are directly installed in muffle furnaces and the air supply is through the chimney. An internal thermowell allows proper temperature control. The cover is useful to avoid a return of air to the catalyst.
  • the 331 g of the precursor obtained previously is precalcined for 4 hours at 300 ° C. under an air flow of 47.9 ml / min / g of precursor.
  • the solid obtained is then calcined for 2 hours at 600 ° C. under a nitrogen flow of 12.8 ml / min / g of solid.
  • a solution A is prepared by dissolving 79.7 g of ammonium heptamoblydate in 220.3 g of water at room temperature, with stirring, for 5 minutes.
  • a solution B is prepared by dissolving 51.5 g of cobalt nitrate and 0.3327 g of potassium nitrate in 55 g of water at room temperature, with stirring, for 5 minutes. This gives a purple solution B.
  • a solution C is prepared by dissolving 56.4 g of iron nitrate, 19.3 g of bismuth nitrate and 28.6 g of nickel nitrate in 85.1 g of water as follows: the nitrates are introduced in a small amount of water, 4.4 g of 68% nitric acid are added, then the rest of the water is added. The mixture is stirred for 30 to 45 minutes.
  • a solution D is prepared by dissolving 44.5 g of LUDOX AS40 silica in 16.4 g of distilled water at room temperature, with stirring.
  • the temperature is increased to 70 ° C and maintained at this temperature for 90 minutes.
  • the mixture is kept stirring at room temperature. Then the temperature is gradually increased to 70 ° C. The mixture is kept stirred at this temperature for 90 minutes. Then, the heating and stirring are stopped and the mixture is allowed to cool to room temperature.
  • the mixture contains approximately 33% by weight of solid matter and its pH is less than 1. The mixture is then micronized in a ball mill until particles are obtained whose average size is less than 2 microns.
  • a polysilicic acid solution (APS) at 6% by weight of silica
  • This solution is prepared by diluting 1091 g of a sodium silicate solution (360 g of silica) with 4909 g of distilled water . This solution is mixed for a few minutes; the pH of this mixture is approximately 12. Then, with vigorous stirring, a sulfonic cation exchange resin sold by the company Dow Chemicals under the trademark DOWEX Monosphere 650C (H) is added, until the pH of the mixture is between 2.5 and 3. Then the resin is filtered and the filtrate is stored in ice and must be used within the next hour to prepare a precursor suspension-PSA solution for atomization.
  • DOWEX Monosphere 650C DOWEX Monosphere 650C
  • 1110 g of the APS solution with 6% silica (obtained in the previous step) are added to 2000 g of the mixture of micronized precursor and the whole is kept under stirring in ice.
  • the resulting suspension which contains 22.7% solids, has a pH of 1 ⁇ 0.1.
  • This suspension is atomized at a speed of about 200 ml / min, with a nozzle pressure of 0.3 bar and a temperature chamber temperature of 390 ° C, so as to obtain porous microspheres, usable in the redox process, in a transported bed.
  • microspheres collected under the atomizer chamber are calcined in an oven by heating from room temperature to 90 ° C in 1 hour, maintaining the temperature at 90 ° C for 2 hours, then heating to 300 ° C in 2 hours, maintaining the temperature at 300 ° C for 5 hours, then heating to 550 ° C in 2 hours and maintaining the temperature at 550 ° C for 6 hours.
  • the desired cocatalyst C is thus obtained.
  • a first height of 1 ml of silicon carbide in the form of particles of 0.62 mm in diameter is loaded into a vertical reactor from the bottom up, a second height of 1 ml of silicon carbide in the form of particles of 0.125 mm in diameter and 5 g of catalyst in the form of particles of 0.02 to 1 mm, then a third height of silicon carbide in the form of particles of 1.19 mm in diameter.
  • the reactor is then heated to 250 ° C and the vaporizer to 200 ° C.
  • the electric priming of the water pump is activated.
  • the water pump is activated and the temperature of the reactor is raised to 380 ° C. and it is waited 30 minutes for the hot point to be stabilized.
  • Each small washing bottle (25 ml of capacity and filled with 20 ml of water) is equipped with a gas pocket, and when the bottle is connected to the outlet of the reactor (as soon as the liquid bubbles) ), the pocket is opened and the stopwatch is started.
  • the gases are analyzed during the balance on a micro-GC Chrompack chromatograph.
  • An acidity assay is carried out on each bottle to determine the exact number of moles of acid produced during each micro-balance and to validate the chromatographic analyzes.
  • the final result which is rendered corresponds to the average of the micro-assessments carried out on the 4 washing bottles and the 4 gas pockets.
  • T3 and T4 tests A third T3 test was carried out with 5 g of catalyst A. The duration of the propane pulses had been adjusted to approximately 12 s, by adjusting the opening time of the mass flow meter. The number of moles of propane sent to the catalyst is thus predetermined. We proceed as described above. The results obtained are collated in Table 2.
  • a fourth test T4 was carried out, by loading into the reactor, instead of the 5 g of catalyst A, a mechanical mixture of 5 g of catalyst A and 5 g of co-catalyst C.
  • the operating parameters were identical.
  • the results obtained are recorded in Table 2 below.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
EP02799759A 2001-11-30 2002-11-28 Verfahren zur herstellung von acrylsäure aus propan in abwesenheit von molekularem sauerstoff Withdrawn EP1453785A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0115524A FR2833005B1 (fr) 2001-11-30 2001-11-30 Procede de fabrication d'acide acrylique a partir de propane et en l'absence d'oxygene moleculaire
FR0115524 2001-11-30
PCT/FR2002/004089 WO2003045886A2 (fr) 2001-11-30 2002-11-28 Procede de fabrication d'acide acrylique a partir de propane et en l'absence d'oxygene moleculaire

Publications (1)

Publication Number Publication Date
EP1453785A2 true EP1453785A2 (de) 2004-09-08

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EP02799759A Withdrawn EP1453785A2 (de) 2001-11-30 2002-11-28 Verfahren zur herstellung von acrylsäure aus propan in abwesenheit von molekularem sauerstoff

Country Status (8)

Country Link
US (1) US7161028B2 (de)
EP (1) EP1453785A2 (de)
JP (1) JP2005510553A (de)
KR (1) KR20040058339A (de)
CN (1) CN1286794C (de)
AU (1) AU2002364406A1 (de)
FR (1) FR2833005B1 (de)
WO (1) WO2003045886A2 (de)

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WO2004024665A1 (fr) * 2002-09-10 2004-03-25 Arkema Procede de fabrication d'acide acrylique a partir de propane
FR2844262B1 (fr) * 2002-09-10 2004-10-15 Atofina Procede de fabrication d'acide acrylique a partir de propane, en l'absence d'oxygene moleculaire
EP1539670A1 (de) * 2002-09-10 2005-06-15 Arkema Verfahren zur herstellung von acrylsäure aus propan in gegenwart von sauerstoff
JP5094459B2 (ja) * 2007-03-09 2012-12-12 ローム アンド ハース カンパニー アルカンを不飽和カルボン酸に変換するための改良法
JP4822559B2 (ja) * 2007-09-19 2011-11-24 ローム アンド ハース カンパニー （メタ）アクリル酸生成物流からのプロピオン酸の選択的減少のための改良された方法
WO2010037011A2 (en) 2008-09-26 2010-04-01 The Ohio State University Conversion of carbonaceous fuels into carbon free energy carriers
ES2630217T3 (es) 2009-09-08 2017-08-18 The Ohio State University Research Foundation Integración de reformación/división de agua y sistemas electromagnéticos para generación de energía con captura de carbono integrada
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CN103354763B (zh) 2010-11-08 2016-01-13 俄亥俄州立大学 具有反应器之间的气体密封和移动床下导管的循环流化床
CN103635673B (zh) 2011-05-11 2016-05-04 俄亥俄州国家创新基金会 载氧材料
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FR2833005A1 (fr) 2003-06-06
US20050054880A1 (en) 2005-03-10
WO2003045886A2 (fr) 2003-06-05
WO2003045886A3 (fr) 2004-02-12
JP2005510553A (ja) 2005-04-21
CN1286794C (zh) 2006-11-29
AU2002364406A8 (en) 2003-06-10
AU2002364406A1 (en) 2003-06-10
FR2833005B1 (fr) 2004-01-23
KR20040058339A (ko) 2004-07-03
US7161028B2 (en) 2007-01-09

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