EP2035138A1 - Système catalyseur et procédé de production d'acides carboxyliques et / ou d'anhydrides d'acides carboxyliques - Google Patents

Système catalyseur et procédé de production d'acides carboxyliques et / ou d'anhydrides d'acides carboxyliques

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Publication number
EP2035138A1
EP2035138A1 EP07729957A EP07729957A EP2035138A1 EP 2035138 A1 EP2035138 A1 EP 2035138A1 EP 07729957 A EP07729957 A EP 07729957A EP 07729957 A EP07729957 A EP 07729957A EP 2035138 A1 EP2035138 A1 EP 2035138A1
Authority
EP
European Patent Office
Prior art keywords
catalyst
catalyst layer
active
weight
layer
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Withdrawn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
EP07729957A
Other languages
German (de)
English (en)
Inventor
Hagen Wilmer
Cornelia Dobner
Tina Einfeld
Sebastian Storck
Jürgen ZÜHLKE
Frank Rosowski
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.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP07729957A priority Critical patent/EP2035138A1/fr
Publication of EP2035138A1 publication Critical patent/EP2035138A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • B01J23/22—Vanadium
    • 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
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
    • B01J27/198—Vanadium
    • B01J35/19—
    • 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
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl 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
    • C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
    • C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
    • 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

Definitions

  • the present invention relates to a catalyst system for the production of carboxylic acids and / or carboxylic anhydrides, which has at least three catalyst layers arranged one above the other in the reaction tube, with the proviso that the active material content, based on the total mass of the catalyst, of one or more of the middle catalyst layer (s) less is as the active mass content of one or more of the upper, to the gas inlet side located catalyst layer (s) and is less than one or more of the lower, to the gas outlet side located catalyst layer (s).
  • the invention further relates to a process for gas phase oxidation in which a gaseous stream comprising a hydrocarbon and molecular oxygen is passed through a plurality of catalyst layers, wherein the active material content, based on the total mass of the catalyst, of one or more of the central catalyst layer (n) is less than the active material content of one or more of the upper, to the gas inlet side located catalyst layer (s) and is less than one or more of the lower, the gas outlet side catalyst layer (s).
  • a variety of carboxylic acids and / or carboxylic anhydrides are industrially prepared by the catalytic gas phase oxidation of aromatic hydrocarbons, such as benzene, xylenes, naphthalene, toluene or durene, in fixed bed reactors. You can in this way z.
  • a mixture of an oxygen-containing gas and the starting material to be oxidized is passed through tubes containing a bed of catalyst. For temperature control, the tubes are surrounded by a heat transfer medium, for example a molten salt.
  • hot spots may occur in the catalyst bed in which a higher temperature prevails than in the remaining part of the catalyst bed or in the remaining part of the catalyst bed. These hot spots lead to side reactions, such as the total combustion of the starting material, or to the formation of undesirable, by the reaction product or only with great effort separable by-products.
  • the catalyst can be damaged irreversibly from a certain hot spot temperature.
  • DE 198 23 262 A1 describes a process for preparing phthalic anhydride with at least three shell catalysts arranged one above the other in layers, wherein the catalyst activity increases from layer to layer from the gas inlet side to the gas outlet side.
  • a yield of 113 m / m% is achieved in a 3-layer catalyst system.
  • the content of phalide is 0.15 to 0.25 mol% in the crude PSA, ie 0.13 to 0.22 wt .-% in the reactor outlet gas.
  • the content of residual o-xylene is not mentioned.
  • EP-A 1 063 222 describes a process for the preparation of phthalic anhydride, which is carried out in one or more fixed bed reactors.
  • the catalyst beds in the reactors have three or more than three individual catalyst layers following each other in the reactor.
  • 30 to 70% by weight of the o-xylene, naphthalene or the mixture of the two used are reacted.
  • 70% by weight or more is reacted.
  • a yield of> 114 m / m% is achieved in a 3-layer catalyst system.
  • the content of phalide is 0.07 mol%, ie 0.06 wt .-%.
  • the content of residual o-xylene is not mentioned.
  • EP-A 1 063 222 further summarizes that the increase in activity is carried out by the following measures or combinations thereof:
  • the by-products which increase during aging, especially in connection with high loading, include not only phthalide (PHD) but also unreacted o-xylene.
  • a very low by-product spectrum in particular very low levels of anthraquinonedicarboxylic acid, is achieved in that only the last catalyst layer has phosphorus and that in the last layer at least 10% by weight of vanadium (calculated as V 2 O 5 ) based on the active material of the catalyst and that the ratio of vanadium (calculated as V 2 O 5 ) to phosphorus has a value of greater than 35.
  • a yield of 113.5% is achieved in a 4-layer catalyst system with a residual o-xylene content of 0.003 wt .-% and a Phalidgehalt of 0.02 wt .-%.
  • WO 2005/115616 describes a process for preparing phthalic anhydride in a fixed bed reactor having three or more catalyst layers with increasing activity in the flow direction. It is disclosed that a low by-product spectrum is achieved when the content of the active compositions and thus the layer thicknesses of the catalysts decreases in the flow direction. In the examples, a yield of 1 13.7% is achieved in a 3-layer catalyst system at a loading of 60 g / Nm 3 . The phalide content is ⁇ 500 ppm, this corresponds to a value of ⁇ 0.5 wt .-%. The content of residual o-xylene is not mentioned.
  • the object has been achieved by a catalyst system for producing carboxylic acids and / or carboxylic anhydrides, which has at least three catalyst layers arranged one above the other in the reaction tube, with the proviso that the active material content, based on the total mass of the catalyst, of one or more of the middle catalyst layer (s) is lower than the active material content of one or more of the upper, to the gas inlet side located catalyst layer (s) and is less than one or more of the lower, to the gas outlet side located catalyst torlage (n).
  • the active material content of the middle layer (s) is advantageously from 0.1 to 5 wt .-% (absolute), preferably 0.1 to 2.5, in particular 0.3 to 1 lower than the active material content of the upper, the gas inlet side located catalyst layer (s).
  • the active material content of the middle layer (s) is advantageously 0.1 to 5% by weight (absolute), preferably 0.1 to 2.5, in particular 0.3 to 1, lower than the active material content of the lower, to the gas outlet side situated catalyst layer (s).
  • the active material content of the upper catalyst layer (s) situated to the gas inlet side is advantageously from 5 to 15% by weight, preferably from 6 to 13% by weight, in particular from 7.5 to 10.5% by weight, based on the total mass of the catalyst.
  • the active material content of the middle catalyst layer (s) is advantageously 5 to 15 wt .-%, preferably 6 to 13 wt .-%, in particular 7 to 10.5 wt .-% based on the total mass of the catalyst.
  • the active material content of the lower catalyst layer (s) located toward the gas outlet side is advantageously from 5 to 15% by weight, preferably from 6 to 13% by weight, in particular from 7.5 to 11% by weight, based on the total mass of the catalyst ,
  • the BET surface area of the catalytically active components of the catalyst is preferably in the range from 5 to 50 m 2 / g, preferably from 5 to 40 m 2 / g, in particular from 9 to 35 m 2 / g.
  • the activity of the catalyst layers advantageously increases from the gas inlet side to the gas outlet side. Possibly.
  • prior art or intermediate catalysts could be used with higher activity (European Patent Application Serial No. 061 12510.0) or one or more moderator sites (European Patent Application 27.04.2006 entitled "Process for Gas Phase Oxidation Using a Moderator Layer” by BASF Aktiengesellschaft).
  • the activity of the catalyst layers preferably increases continuously from the gas inlet side to the gas outlet side.
  • the activity of a catalyst layer is defined as follows: the higher the conversion for a particular reactant mixture at the same salt bath temperature, the higher the activity.
  • the bed length of the upper catalyst layer in a 3-layer catalyst system preferably accounts for 27 to 60%, in particular 40 to 55% of the total Katalysator Stahl in the reactor.
  • the bed length of the middle layer preferably accounts for 15 to 55%, preferably 20 to 40% of the total bed length.
  • the upper layer advantageously makes 27 to 55%, in particular 32 to 47%, the upper middle layer advantageously 5 to 30%, preferably 10 to 25% and the lower middle layer advantageously 8 to 35% , in particular 12 to 30%, of the total bed height in the reactor.
  • the lowest layer of a 4-layer catalyst system advantageously accounts for 8 to 35%, in particular 12 to 30%, of the total bed height in the reactor.
  • the catalyst layers may also be optionally distributed to multiple reactors.
  • Typical reactors have a filling height of 2.5 to 3.4 meters.
  • the catalytically active composition of all catalysts preferably comprises at least vanadium oxide and titanium dioxide.
  • the catalytically active composition may be contained oxidic compounds which, as promoters, influence the activity and selectivity of the catalyst, for example by lowering or increasing its activity.
  • activity-influencing promoters are the alkali metal oxides, in particular cesium oxide, lithium, potassium and rubidium oxide, thallium (I) oxide, alumina, zirconium oxide, iron oxide, nickel oxide, cobalt oxide, manganese oxide, tin oxide, silver oxide, copper oxide, chromium oxide, molybdenum oxide, tungsten oxide, iridium oxide , Tantalum oxide, nickel oxide, arsenic oxide, antimony oxide, ceria.
  • cesium is used as promoter from this group.
  • Suitable sources of these elements are the oxides or hydroxides or the salts which can be thermally converted into oxides, such as carboxylates, in particular the acetates, malonates or oxalates, carbonates, bicarbonates or nitrates.
  • oxides or hydroxides or the salts which can be thermally converted into oxides, such as carboxylates, in particular the acetates, malonates or oxalates, carbonates, bicarbonates or nitrates.
  • oxidic phosphorus compounds in particular phosphorus pentoxide
  • phosphoric acid, phosphorous acid, hypophosphorous acid, ammonium phosphate or phosphoric acid ester and above all ammonium dihydrogen phosphate are suitable as the phosphorus source.
  • antimony oxides especially antimony trioxide.
  • a higher activity of a catalyst layer is advantageously achieved by a lower content of cesium in the active composition, by a higher re active material per tube volume, achieved by a higher content of vanadium in the active composition, by a higher BET surface area of the catalysts or by a combination of the said possibilities.
  • the catalysts used in the process according to the invention are generally coated catalysts in which the catalytically active composition is applied in the form of a dish on an inert support.
  • the layer thickness of the catalytically active composition is generally 0.02 to 0.25 mm, preferably 0.05 to 0.15 mm.
  • the catalysts have a cup-shaped active mass layer of substantially homogeneous chemical composition.
  • one or more successive two or more different active mass layers can be applied to a carrier. It is then spoken of a two- or multi-layer catalyst (see, for example, DE 19839001 A1).
  • Steatite is preferably used in the form of spheres with a diameter of 3 to 6 mm or of rings with an outer diameter of 5 to 9 mm, a length of 4 to 7 mm and an inner diameter of 3 to 7 mm.
  • the application of the individual layers of the coated catalyst can be carried out by any known methods, for.
  • the active composition of the upper, to the gas inlet side catalyst layer (s) advantageously includes on non-porous and / or porous support material 7 to 11% by weight, based on the total catalyst, active composition, containing 4 to 1 1 wt% V 2 O 5 , 0 to 4% by weight Sb 2 O 3 or Nb 2 O 5 , 0 to 0.5% by weight P, 0.1 to 1, 1% by weight alkali (calc. As alkali metal) and the remainder TiO 2 in anatase form.
  • the active composition of the middle catalyst layer (s) advantageously contains on non-porous and / or porous carrier material 7 to 11 wt .-%, based on the total catalyst, active composition, containing 5 to 13 wt .-% V 2 O 5 , 0 to 4% by weight of Sb 2 O 3 or Nb 2 O 5 , 0 to 0.5% by weight of P, 0 to 0.4% by weight of alkali (calculated as alkali metal) and the remainder as TiO 2 in anatase form.
  • the active composition of the lower, to Gausauseriesseite catalyst layer (s) advantageously includes on non-porous and / or porous support material 8 to 12 wt .-%, based on the total catalyst, active composition, containing 10 to 30 wt .-% V 2 O 5 , 0 to 4 wt .-% Sb 2 O 3 or Nb 2 O 5 , 0 to 0.5 wt .-% P, 0 to 0.1 wt .-% alkali (calc. As the alkali metal) and the balance TiO 2 in anatase form.
  • the anatase titanium dioxide used advantageously has a BET surface area of from 5 to 50 m 2 / g, in particular from 15 to 40 m 2 / g. It is also possible to use mixtures of anatase titanium dioxide with a different BET surface area, with the proviso that the resulting BET surface area has a value of 15 to 40 m 2 / g.
  • the individual catalyst layers may also have titanium dioxide with different BET surface areas.
  • the BET surface area of the titanium dioxide used preferably increases from the upper catalyst layers located toward the gas inlet to the lower catalyst layers located toward the gas outlet.
  • FIGS. 1 to 3 show catalyst systems according to the invention with four catalyst layers arranged one above the other in the reaction tube.
  • FIGS. 20 and 23 show catalyst systems which are not according to the invention and which have hitherto not been described in the prior art.
  • the catalysts are filled for reaction in layers in the tubes of a Rohbündelreaktors.
  • the different active catalysts can be thermostated to the same or different temperatures.
  • the present invention relates to a process for gas phase oxidation in which a gaseous stream comprising at least one hydrocarbon and molecular oxygen is passed through at least three catalyst layers arranged one above the other in the reaction tube, wherein the amount of active composition, based on the total mass of the catalyst, one or more the mean catalyst layer (s) is lower than the active material content of one or more of the upper, to the gas inlet side catalyst layer (s) and one or more of the lower, the gas outlet side catalyst layer (s).
  • the process according to the invention is advantageously suitable for the gas-phase oxidation of aromatic C 6 -C 10 -hydrocarbons, such as benzene, xylenes, toluene, naphthalene or durene (1, 2,4,5-tetramethylbenzene) to carboxylic acids and / or carboxylic anhydrides, such as maleic anhydride, phthalic anhydride, benzoic acid and / or or pyromellitic dianhydride.
  • the process is suitable for the preparation of phthalic anhydride from o-xylene and / or naphthalene.
  • the gas-phase reactions for the preparation of phthalic anhydride are generally known and are described, for example, in WO 2004/103561 on page 6.
  • the applied to the steatite rings active composition was 8.7%.
  • the analyzed composition of the active composition consisted of 7.1% V 2 O 5 , 1.8% Sb 2 O 3 , 0.41% Cs, balance TiO 2 .
  • Catalyst K4 Preparation analogous to K1 with variation of the composition of the suspension. After calcination of the catalyst for one hour at 450 ° C, the applied to the steatite rings active mass was 9.1%.
  • the analyzed composition of the active composition consisted of 20% V 2 O 5 , 0.38% P, remainder TiO 2 .

Abstract

Système catalyseur et procédé de production d'acides carboxyliques et / ou d'anhydrides d'acides carboxyliques, qui possède au moins trois couches de catalyseur placées les unes sur les autres dans le tube de réaction, à condition que la fraction de masse active, par rapport à la masse totale du catalyseur, d'une ou des couches médianes soit inférieure à la fraction de masse active d'une ou des couches supérieures de catalyseur situées du côté de l'entrée des gaz, et soit inférieure à la masse active d'une ou des couches de catalyseur inférieures situées du côté de la sortie des gaz. La présente invention concerne en outre un procédé d'oxydation en phase gazeuse à l'aide du système catalyseur décrit.
EP07729957A 2006-06-20 2007-06-06 Système catalyseur et procédé de production d'acides carboxyliques et / ou d'anhydrides d'acides carboxyliques Withdrawn EP2035138A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07729957A EP2035138A1 (fr) 2006-06-20 2007-06-06 Système catalyseur et procédé de production d'acides carboxyliques et / ou d'anhydrides d'acides carboxyliques

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP06115699 2006-06-20
PCT/EP2007/055583 WO2007147733A1 (fr) 2006-06-20 2007-06-06 Système catalyseur et procédé de production d'acides carboxyliques et / ou d'anhydrides d'acides carboxyliques
EP07729957A EP2035138A1 (fr) 2006-06-20 2007-06-06 Système catalyseur et procédé de production d'acides carboxyliques et / ou d'anhydrides d'acides carboxyliques

Publications (1)

Publication Number Publication Date
EP2035138A1 true EP2035138A1 (fr) 2009-03-18

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EP07729957A Withdrawn EP2035138A1 (fr) 2006-06-20 2007-06-06 Système catalyseur et procédé de production d'acides carboxyliques et / ou d'anhydrides d'acides carboxyliques

Country Status (6)

Country Link
US (1) US20090318712A1 (fr)
EP (1) EP2035138A1 (fr)
JP (1) JP2009541245A (fr)
CN (1) CN101472680A (fr)
TW (1) TW200808441A (fr)
WO (1) WO2007147733A1 (fr)

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US8263789B2 (en) 2006-12-21 2012-09-11 Basf Se Catalyst system and method for gas phase oxidation using an upstream layer
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JP5586581B2 (ja) 2008-04-07 2014-09-10 ビーエーエスエフ ソシエタス・ヨーロピア 気相酸化反応器の始動方法
DE102009041960A1 (de) * 2009-09-17 2011-04-07 Süd-Chemie AG Verfahren zur Herstellung einer Katalysatoranordnung für die Herstellung von Phthalsäureanhydrid
WO2011061132A1 (fr) * 2009-11-20 2011-05-26 Basf Se Catalyseur multicouche utilisé pour la production d'acides carboxyliques et/ou d'anhydrides d'acide carboxylique, à l'antimoniate de vanadium dans au moins une couche de catalyseur, et procédé de production d'anhydride d'acide phtalique à basse température en zone de surchauffe maximale
US20110230668A1 (en) * 2010-03-19 2011-09-22 Basf Se Catalyst for gas phase oxidations based on low-sulfur and low-calcium titanium dioxide
US8901320B2 (en) 2010-04-13 2014-12-02 Basf Se Process for controlling a gas phase oxidation reactor for preparation of phthalic anhydride
US8859459B2 (en) 2010-06-30 2014-10-14 Basf Se Multilayer catalyst for preparing phthalic anhydride and process for preparing phthalic anhydride
JP5879342B2 (ja) * 2010-06-30 2016-03-08 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 無水フタル酸を製造するための多層触媒、及び無水フタル酸の製造方法
US9212157B2 (en) 2010-07-30 2015-12-15 Basf Se Catalyst for the oxidation of o-xylene and/or naphthalene to phthalic anhydride
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CN116060025A (zh) * 2021-10-31 2023-05-05 中国石油化工股份有限公司 一种加氢催化剂及其制备方法和应用

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CN101472680A (zh) 2009-07-01
TW200808441A (en) 2008-02-16
WO2007147733A1 (fr) 2007-12-27
US20090318712A1 (en) 2009-12-24

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