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EP1341608A2 - Procede de production d'un catalyseur a base de metal alcalin, et utilisation de ce catalyseur pour l'alkylation par chaine laterale d'aromatiques alkyliques - Google Patents

Procede de production d'un catalyseur a base de metal alcalin, et utilisation de ce catalyseur pour l'alkylation par chaine laterale d'aromatiques alkyliques

Info

Publication number
EP1341608A2
EP1341608A2 EP01991839A EP01991839A EP1341608A2 EP 1341608 A2 EP1341608 A2 EP 1341608A2 EP 01991839 A EP01991839 A EP 01991839A EP 01991839 A EP01991839 A EP 01991839A EP 1341608 A2 EP1341608 A2 EP 1341608A2
Authority
EP
European Patent Office
Prior art keywords
alkali metal
catalyst
potassium carbonate
reaction
alkyl
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.)
Ceased
Application number
EP01991839A
Other languages
German (de)
English (en)
Inventor
Ulrich Steinbrenner
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
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 BASF SE filed Critical BASF SE
Publication of EP1341608A2 publication Critical patent/EP1341608A2/fr
Ceased legal-status Critical Current

Links

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
    • B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
    • B01J23/04—Alkali metals
    • 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
    • B01J27/20—Carbon compounds
    • B01J27/232—Carbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/72—Addition to a non-aromatic carbon atom of hydrocarbons containing a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
    • C07C2523/04—Alkali metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/20—Carbon compounds
    • C07C2527/232—Carbonates

Definitions

  • the invention relates to a process for the preparation of an alkali metal catalyst and to the use thereof for the side chain alkylation of alkylaromatics which have at least one alkyl side chain with an ⁇ -oxygen atom.
  • This process is also known as side chain alkylation.
  • Sodium, potassium or sodium / potassium alloy are frequently used as alkali metals. Because of the comparatively low selectivity of the alkali metal for this reaction, however, by-products are often formed.
  • the cyclization of the primary alkyl aromatic is also observed.
  • alkali metal catalysts for side chain alkylation have been described in the prior art which contain the alkali metal in finely divided form on an inorganic support.
  • potassium carbonate see for example GB 933,253, GB 2,249,737, GB 2,254,802, FR 2,609,024, EP-A 173 335, WO 88/04955, J 61053-229-A,
  • the object of the present invention was to provide an alkali metal catalyst which is suitable for the side chain alkylation of alkyl aromatics with olefins.
  • the catalyst should be characterized by a good space-time yield and a high selectivity.
  • an alkali metal catalyst in the form of an alkali metal which is finely distributed on an inorganic support material, the inorganic material being a potassium carbonate with a specific surface area of at least 0.3 m 2 / g.
  • the present invention thus relates on the one hand to a process for the preparation of an alkali metal catalyst by mixing an alkali metal with powdery, solid potassium carbonate as a support, which is characterized in that the potassium carbonate has a specific surface area of at least 0.3 m 2 / g.
  • the process also relates to the catalysts obtainable by this process.
  • the advantageous properties of the catalysts according to the invention are based on the combination of potassium carbonate and the high specific surface area of the potassium carbonate. According to the invention, this is at least 0.3 m 2 / g, preferably at least 0.32 m 2 / g and in particular at least 0.35 m 2 / g and is particularly preferably in the range from 0.35 to 3.0 m 2 / g. According to the invention, the so-called BET surface, as determined according to DIN 66131, is used as the specific surface.
  • a potassium carbonate with a larger specific surface over a longer period of time requires significantly higher space-time yields and selectivities with regard to the target product.
  • the decisive factor is that it is a Potassium carbonate surface.
  • a high surface area of the carrier material itself is not sufficient for the advantages of the method according to the invention.
  • the addition of larger amounts of perovskite with a high specific surface area, e.g. B. in the range of 10 to 20 m 2 / g to the support according to the invention no advantages but significant disadvantages with regard to the selectivity towards undesired ring closure reactions and shorter catalyst downtimes.
  • This effect can also be found in other inorganic supports with a high specific surface area, such as aluminum oxide or magnesium oxide.
  • Additions of other inorganic carrier materials with a comparable high specific surface area are therefore only tolerable in small amounts, e.g. B. in amounts ⁇ 10 wt .-%, in particular ⁇ 5 wt .-%, based on the total amount of carrier material.
  • the origin of the potassium carbonate is of minor importance for the method according to the invention as long as it has the surface according to the invention.
  • the potassium carbonate can, for example, have been produced from another potassium compound by heating, for example in air, carbon dioxide, oxygen or inert gas.
  • a potassium carbonate is preferably used as the carrier, which was preferably prepared by carbonizing potassium hydroxide solution.
  • Sodium has proven particularly useful as an alkali metal, which is also inexpensive and easy to handle. It can also contain up to 5% by weight of other metals, as are usually found in technical sodium, for example potassium, calcium or strontium. In particular, technical grade sodium is used which usually contains less than 1% by weight of the above metals as impurities.
  • the weight ratio of alkali metal to potassium carbonate is preferably in the range from 1: 1 to 1:50, in particular in the range from 1: 2 to 1:30 and particularly preferably in the range from 1: 5 to 1 : 20th
  • the catalysts of the invention can be prepared in the manner known for the preparation of supported alkali metal catalysts. To be mentioned here:
  • the potassium carbonate will only contain small amounts of water, preferably not more than 2000 ppm and in particular not more than 500 ppm.
  • the potassium carbonate is subjected to a drying process before treatment with the alkali metal. It is preferably heated to temperatures> 100 ° C., in particular above 200 ° C. A vacuum can be applied to assist drying and / or an inert gas stream can be passed through the potassium carbonate.
  • the potassium carbonate used to produce the alkali metal catalyst has an average grain size below 1000 ⁇ m, in particular below 200 ⁇ m and particularly preferably in the range from 10 to 100 ⁇ m.
  • the potassium carbonate is ground in the equipment customary for this, such as ball mills, Retsch or impact body mills.
  • an alkali metal catalyst which can be obtained by mixing the molten alkali metal at temperatures above the melting temperature of the alkali metal with the solid, powdered potassium carbonate.
  • a potassium carbonate is used, which, for example, at temperatures> 200 ° C. B. 250 ° C to 400 ° C in an inert gas stream.
  • Mixing is preferably carried out at a temperature of at least 100 ° C., preferably at least 150 ° C. and in particular at least 200 ° C.
  • a temperature of 500 ° C. and in particular 400 ° C. is preferably not exceeded.
  • mixing takes at least 30 minutes, preferably at least 60 minutes and in particular at least 90 minutes.
  • the alkali metal can be added to the carrier as a strand or block and mixed with it while heating.
  • the powdered potassium carbonate can also be added to a melt of the alkali metal.
  • the alkali metal is mixed with the carrier material in the usual equipment, for example in stirred tanks, paddle dryers, kneaders, pan mills or Discotherm equipment.
  • the mixing of alkali metal and inorganic substance is carried out under inert conditions, e.g. B. under an inert gas such as nitrogen or argon or under an inert gas mixture, the inert gas usually containing less than 500 ppm oxygen and less than 100 ppm water.
  • inert conditions e.g. B. under an inert gas such as nitrogen or argon or under an inert gas mixture, the inert gas usually containing less than 500 ppm oxygen and less than 100 ppm water.
  • the alkali metal catalyst can be hydrogenated after the alkali metal has been applied to the support material by preferably mixing the mixture of alkali metal and support material with hydrogen or a mixture of an inert gas and hydrogen at temperatures in the range from 100 ° C. to 400 ° C. treated in the range of 200 ° C to 300 ° C. The catalyst is cooled and stored under an inert gas.
  • the hydrogenation takes place at normal pressure.
  • the hydrogenation presumably produces alkali hydride catalysts, which also catalyze the basic side chain alkylation. Without being bound by any theory, it is believed that even without external hydrogen supply under the reaction conditions a partial hydrogenation of the catalyst takes place in situ by the hydrogen formed as a by-product in the side chain alkylation.
  • the catalyst according to the invention In the presence of the catalyst according to the invention, reactions of alkyl aromatics which contain ⁇ -hydrogen atoms with olefins can be carried out with high selectivity and good space-time yields.
  • the catalysts according to the invention are suitable for deliberately carrying out dimerizations and codimerizations of olefins.
  • Suitable olefins for the process for side chain alkylation according to the invention are monoolefins and conjugated olefins.
  • Suitable monoolefins for the side chain alkylation are in particular those with 2 to 10 and particularly preferably those with 2 to 5 carbon atoms. Examples include ethene, propene,
  • Particularly preferred monoolefins are ethene, propene and 1- or 2-butenes.
  • the catalysts of the invention can also be used for the dimerization of the aforementioned olefins, for example for the dimerization of propene to hexene or preferably for the codimerization of ethene with 1- or 2-butene to form hexenes.
  • Suitable conjugated diolefins for the side chain alkylation of alkyl aromatics are those with 4 to 10 carbon atoms such as 1,3-butadiene, 2-methyl-1,3-butadiene, 1,3-pentadiene, etc., in particular 1,3-butadiene.
  • alkylaromatics use is generally made of derivatives of benzene or naphthalene which have one, two or three alkyl radicals having 1 to 10 carbon atoms, preferably having 1 to 6 carbon atoms and in particular having 1 to 3 carbon atoms, at least one of these radicals has a hydrogen tom on an ⁇ -carbon atom.
  • Typical alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and n-pentyl.
  • Examples of such compounds are mono-, di- and tri-C ⁇ -C 3 -alkylbenzenes such as toluene, xylenes, methylnaphthalenes, mesitylene, ethylbenzenes and isopropylbenzenes, where the latter two types of compounds can also have one or two further methyl groups.
  • Derivatives of benzene or naphthalene are also suitable, in which two alkyl radicals together with the aromatic ring to which they are attached form an alicyelic ring, which may also have an oxygen atom.
  • Examples of such compounds are 1,2,3,4-tetrahydronaphthalene, indane and chroman.
  • Preferred alkyl aromatics are derivatives of benzene, in particular those which have one or two alkyl groups. Preferred alkyl aromatics in particular have at least one methyl group and / or one isopropyl group. Examples of preferred alkyl aromatics are toluene, ortho-xylene, meta-xylene, para-xylene, l-ethyl-2-methylbenzene, l-ethyl-3-methylbenzene, 1,2,4-trimethylbenzene, isopropylbenzene, 4 isopropyl-l-methyl-benzene.
  • toluene the xylenes and isopropylbenzene are particularly preferred, and toluene and o-xylene are very particularly preferred.
  • the process according to the invention can be used, for example, to convert cumene to ethene.
  • the alkylation generally takes place at elevated temperature, ie at temperatures above room temperature, preferably above 80 ° C. and in particular above 100 ° C.
  • the reaction temperature in the process according to the invention will not exceed 300 ° C., preferably 250 ° C. and in particular 200 ° C.
  • the reaction is particularly preferably carried out below 180 ° C. and very particularly preferably below 160 ° C., for example at 120 ° C. to 140 ° C.
  • the process according to the invention can be carried out both in the gas phase and in the liquid phase.
  • the olefin can also be introduced in gaseous form into the liquid reaction phase which contains the alkali metal catalyst and the alkylaromatics.
  • the reaction is preferably carried out in a liquid reaction phase.
  • the liquid reaction phase can also contain a solvent which is inert under the reaction conditions. Examples include aliphatic and alicyclic hydrocarbons such as octane, hexane, cyclohexane, cyclooctane and decalin. However, it is preferred to work in bulk, i.e. H. the liquid reaction phase contains only the liquid feed components and the alkali metal catalyst.
  • the feedstocks usually contain less than 1000 ppm and very particularly preferably less than
  • the oxygen content of the starting materials is generally below 500 ppm and particularly preferably below 50 ppm.
  • the water from the feedstocks will be used for this by known methods, e.g. B. by using drying agents such as active alumina, silica gel, molecular sieve or activated carbon, by treatment with metallic sodium or potassium or by freezing.
  • the reaction can be carried out both under an inert gas atmosphere and under the vapor pressure of the liquid reaction phase.
  • the reaction is particularly preferably carried out in a completely or almost completely flooded reactor which contains practically no gas phase. This procedure is particularly preferred when the method is carried out continuously.
  • the olefin is preferably used in a molar deficit, based on the alkylaromatics.
  • the molar ratio of olefin to alkyl aromatic preferably does not exceed a value of 0.8, in particular 0.6 and particularly preferably 0.5.
  • the molar ratio is preferred be at least 0.1, in particular 0.2 and particularly preferably at least 0.3. This measure avoids the dimerization of the olefin and subsequent reactions of the alkyl aromatics formed in the reaction, which may still have active hydrogen atoms.
  • an excess of olefin, based on the alkylaromatics can also be used, in particular if an alkylaromatic compound is formed in the process according to the invention which no longer has an ⁇ -hydrogen atom, for example the tert formed in the reaction of cumene with ethene. -Amylbenzol.
  • the method according to the invention can be designed as a batch method and as a continuous method.
  • the procedure is generally such that the alkylaromatics and the alkali metal catalyst are initially charged and the olefin, preferably in liquid form, is added to this under reaction conditions, depending on its consumption. In this way it is achieved that the olefin is in a deficit in the reaction mixture, based on the alkylaromatic.
  • the reaction is stopped by cooling the reaction mixture, the alkali metal catalyst is separated off and the mixture is worked up in the usual manner, preferably by distillation.
  • the process according to the invention is preferably carried out continuously.
  • the feedstocks are passed continuously under reaction conditions through a reaction zone charged with the catalyst.
  • the alkali metal catalyst can be in the form of a fixed bed in the reaction zone. However, it is preferably in the form of a suspension in the liquid reaction phase.
  • the liquid reaction phase is preferably stirred intensively, for example using impeller turbines or anchor stirrers.
  • the starting materials can be fed into the reactor both in one stream and in separate streams.
  • the rate at which the feedstocks are fed into the reactor naturally depends on the reactivity of the feedstocks and the catalyst.
  • the feed rate is preferably in the range from 0.05 to 5 kg of starting materials per kg of catalyst mass and hour, in particular in the range from 0.1 to 1 kg / h per kg of catalyst mass.
  • a molar ratio of Al- kylaromat to olefin below 1 and in particular in the range from 1:10 to 1: 2 and especially in the range from 1: 4 to 2: 3.
  • the catalyst is generally separated from the reaction phase and worked up by distillation. Residues of catalyst that remained in the reaction phase due to incomplete removal of the catalyst are generally deactivated before working up, for example by adding water and / or alkanols such as methanol, ethanol or isopropanol. If the reaction is carried out continuously, the procedure will generally be to discharge an amount of liquid reaction phase which corresponds to the amount supplied and to work up in the manner described above.
  • the liquid reaction phase is preferably discharged with extensive or complete retention of the alkali metal catalyst in the reaction space.
  • the catalyst is retained, for example, by means of suitable filters or separators such as cross flow filters, candle filters, membranes or settlers.
  • the liquid reaction phase is separated into the product of value, by-products, optionally solvents and excess alkylaromatic.
  • the excess alkyl aromatic which may be obtained is preferably returned to the process.
  • the dimerization and codimerization of olefins is preferably carried out analogously to the side chain alkylation of alkyl aromatics.
  • the alkali metal catalysts according to the invention provide the desired alkyl aromatics with high selectivity and space-time yield. Surprisingly, the alkali metal catalysts suitable according to the invention are superior in terms of service life to the alkali metal catalysts of the prior art.
  • Catalyst B 10.8 g of sodium on a mixture of 70 g of dry CaTi0 3 (BET surface area 14.6 m 2 / g) and 70 g of potassium carbonate (not according to the invention).
  • Catalyst C 10.8 g sodium on 70 g potassium carbonate with a BET surface area of 0.29 m 2 / g (not according to the invention).
  • the reaction was carried out continuously in a stirred tank reactor with an internal volume of 270 ml, which was equipped with a magnetically coupled stirrer with an impeller turbine.
  • the reactor each contained the catalyst suspension and was flooded with the mixture of liquid propene and toluene before the start of the reaction.
  • the reactor was heated to 130 ° C. and stirred at speeds in the range from 1,000 to 1,200 rpm. 0.132 mol / h dry liquid propene and 0.316 mol / h dry toluene were fed continuously into the reactor.
  • the reaction discharge was drawn off via a 4 ⁇ m filter and analyzed for the content of the products by means of online gas chromatography.
  • Tables 1 to 3 below show the results for run times in the range from 10 to 100 hours.
  • T toluene
  • IBB isobutylbenzene
  • nBB n-butylbenzene
  • I indan
  • P propene
  • Kat catalyst
  • GC gas chromatogram
  • T toluene
  • IBB isobutylbenzene
  • nBB n-butylbenzene
  • I indan
  • P propene
  • Kat catalyst
  • GC gas chromatogram
  • T toluene
  • IBB isobutylbenzene
  • nBB n-butylbenzene
  • Kat catalyst
  • GC gas chromatogram
  • the catalysts according to the invention compared to the catalysts with conventional potassium carbonate as a carrier with regard to the selectivity isobutylbenzene vs. n-butylbenzene are superior.
  • the catalysts according to the invention are distinguished by better space-time yields, in particular in the case of longer service lives.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne un procédé de production d'un catalyseur à base de métal alcalin par mélange d'un métal alcalin avec, comme support, du carbonate de potassium solide en poudre. Ce procédé se caractérise en ce que le carbonate en poudre présente une surface spécifique d'au moins 0,3 m<2>/g. L'invention concerne également l'utilisation de ce catalyseur pour l'alkylation par chaîne latérale de benzols alkyliques.
EP01991839A 2000-12-14 2001-12-13 Procede de production d'un catalyseur a base de metal alcalin, et utilisation de ce catalyseur pour l'alkylation par chaine laterale d'aromatiques alkyliques Ceased EP1341608A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10062242 2000-12-14
DE10062242A DE10062242A1 (de) 2000-12-14 2000-12-14 Verfahren zur Herstellung eines Alkalimetall-Katalysators sowie dessen Verwendung zur Seitenkettenalkylierung von Alkylaromaten
PCT/EP2001/014686 WO2002047813A2 (fr) 2000-12-14 2001-12-13 Procede de production d'un catalyseur a base de metal alcalin, et utilisation de ce catalyseur pour l'alkylation par chaine laterale d'aromatiques alkyliques

Publications (1)

Publication Number Publication Date
EP1341608A2 true EP1341608A2 (fr) 2003-09-10

Family

ID=7667073

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01991839A Ceased EP1341608A2 (fr) 2000-12-14 2001-12-13 Procede de production d'un catalyseur a base de metal alcalin, et utilisation de ce catalyseur pour l'alkylation par chaine laterale d'aromatiques alkyliques

Country Status (5)

Country Link
US (1) US7148177B2 (fr)
EP (1) EP1341608A2 (fr)
JP (1) JP2004522564A (fr)
DE (1) DE10062242A1 (fr)
WO (1) WO2002047813A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4809205B2 (ja) * 2006-12-19 2011-11-09 三井化学株式会社 α−オレフィン二量化用触媒およびα−オレフィン二量体の製造方法。
WO2020240460A1 (fr) * 2019-05-31 2020-12-03 Mangalore Refinery & Petrochemicals Ltd. Isobutyle benzène et procédé de synthèse d'isobutyle benzène à l'aide d'un catalyseur

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Also Published As

Publication number Publication date
DE10062242A1 (de) 2002-06-20
US7148177B2 (en) 2006-12-12
JP2004522564A (ja) 2004-07-29
US20040059168A1 (en) 2004-03-25
WO2002047813A3 (fr) 2002-08-08
WO2002047813A2 (fr) 2002-06-20

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