The method of obtaining oxide catalysts containing copper to oxidation more than zero

 

The invention relates to a method of producing an oxide catalyst containing copper to oxidation more than zero for the dehydrogenation of secondary alcohols by treatment of solid oxide carrier with an aqueous solution containing at least one salt of copper, followed by calcination, and the copper is applied on the carrier by deposition from aqueous solution using precipitating means, with an aqueous solution containing water-soluble organic polymer in a concentration of from 0.1 to 100 g/l, coordinating binding copper ions, and selected from homopolymers of N-vinylpyrrolidone. The invention also concerns the catalysts obtained using this method, and method of dehydrogenation of secondary alcohols to ketones using catalysts of this method, especially the method of dehydrogenation of cyclohexanol. The technical effect of improving the activity of the catalyst with high selectivity. 3 s and 5 C.p. f-crystals, 1 table.

The invention relates to a method of producing an oxide catalyst containing copper to oxidation more than zero, by processing the solid oxide material carrier water restore using this method, as well as their application in the hydrogenation of secondary alcohols to ketones, especially for the dehydrogenation of cyclohexanol to cyclohexanone.

Catalytic dehydrogenation of secondary alcohols in industrial production of ketones, especially when getting cyclohexanone from cyclohexanol, plays an important role (see, for example, K. Weissermel, H.-J. Agra, Industrielle organische Chemie ("Industrial organic chemistry") 4 Aufl. Verlag Chemie, Weinheim, 1994, P. 274). These methods, as will become clear from the form of the present invention, are known in different ways and require only basic explanations. Generally, these methods alkanol or alkanol/ketone mixture in contact with a carrier of copper at elevated temperatures, typically above 200oC. Here it is crucial to bear in mind that the catalytic dehydrogenation of alcohols to ketones is usually reversible, and the equilibrium position with decreasing temperature is shifted in the direction of the educt or dedicated substances. With decreasing temperature, the equilibrium slows down, which results in a low degree of conversion. If the method is carried out at elevated temperature, for example above 400oSince it is a low selectivity with respect to the mouths or dimerization of the resulting ketones.

For the dehydrogenation of alcohols at temperatures below 400oTo apply often the catalysts containing copper as an active ingredient in a solid, in most cases, the oxide carrier. The copper content of such catalysts may be up to 50 wt.% in terms of the total weight of the catalyst. Typical materials native oxide type are ceramic oxides such as aluminum oxide, zirconium dioxide and titanium dioxide, hereinafter the zeolite and pumice. Along with copper, as the active component of the catalysts of the prior art often contain small amounts of alkali metals as promoters.

For non-oxidative dehydrogenation of cyclohexanol known catalysts si/Al2O3the UK patent GB-A1081491, Cu/Li/5 SiO2patent USSR SU-A 465217, C/K/Al2About3patent USSR SU-A 522853. Consider copper catalysts in most cases get method, in which copper active ingredients applied on the pre-made media or by deposition of a copper salt, or by soaking the corresponding solution of copper salt, or deposition of all of the components constituting the catalyst.

Chang et al. (Appl. Catal. A 103(1994), S. 233-4 is vosstanovitelnogo deposition of copper on-Al2About3as the carrier.

The lack of restorative deposition is that, as a rule, to achieve a uniform deposition of copper on the media last first, you need to hunt a noble metal such as platinum, rhodium, iridium, gold or palladium. This leads to additional costs. In addition, the catalysts described (Supply) Chang et al., we are talking about powders, from which it is difficult to prepare tablets, as these powders are only conditionally can be processed into a molded body, such as, for example, tablet. Therefore, for industrial applications, these catalysts are not suitable.

Next Supply (Chang et al. (Appl. Catal. A 115 (1994), S. 29-44) describes the copper catalysts that get by alkaline precipitation of copper from aqueous copper salt solution to the media - silicon dioxide. Obtained according to the methods described there, the catalysts are relatively high selectivity, but their activity for the intended use is not sufficient.

In addition, in the known catalysts with increasing downtime reduced activity. This leads to the fact that in case of prolonged operation must constantly Russkiye deactivation of the catalyst.

Thus, the task of the invention to provide catalysts for non-oxidative dehydrogenation of secondary alcohols to the corresponding ketones with high activity and high selectivity. In addition, after long usage, it should not lose its activity. Then getting it should not be costly, and he should possess superior mechanical properties.

This problem is solved by the present invention using the catalysts obtained by processing the solid oxide carrier with an aqueous solution of salt of copper, containing at least one organic, water-soluble polymer, coordinating binding copper ions, followed by calcination.

According to the above present invention relates to a method of producing an oxide catalyst containing copper to oxidation more than 0, by processing the solid oxide carrier with an aqueous solution containing at least one salt of copper, and subsequent calcination, wherein the aqueous copper salt solution contains at least one organic water-soluble polymer, coordinating binding copper ions in a concentration from 0.1 to 100 g/L. Mistressmadeleine the present invention, coordinating binding copper ions, contain or carboxylate groups, or amino groups and/or carboxamide group. Polymers containing carboxylate groups, are, as a rule, Homo - or copolymers of acrylic acid, methacrylic acid, crotonic acid, maleic acid, fumaric acid and basis of itaconic acid. Typically, the polymers of the invention under examination containing carboxylate groups, are not less than 50 mol % of the above Ethylenediamine carboxylic acids in terms of the total number of their constituent monomers.

Suitable comonomers are, first and foremost, monomers with high solubility in water (i.e. more than 60 g/l at a temperature of 25oC), for example, amides of the above Ethylenediamine carboxylic acids, N-vinylacetate and hydroxyalkylated above Ethylenediamine carboxylic acids. Preferred polymers containing carboxylate groups, are Homo - and copolymers of acrylic acid.

Typical polymers containing amide groups, are Homo - and copolymers of unsaturated amides monoetilenglikolya acids, for example, polymers of acrylamide and/or methacrylamide. Typically, these floor is Auda above Ethylenediamine carboxylic acid or N-vinylacetate. The following class of polymers containing amide groups, contains at least 50 mol % of the polymer of N-vinylation, such as N-vinyl pyrrolidone, N-vinylcaprolactam and N-vinylpyridine. Suitable comonomers for N-vinylacetate are above unsaturated Telecabine acids, their amides, their hydroxyalkylated, vinyl acetate, finalproject and nitrogen, vinylsubstituted a heterocycle, as vinylpyridine and vinylimidazole.

Polymers containing amino groups, include both Homo-and copolymers of monomers containing amino groups, and such polymers, which can be obtained by transformation similar to the polymerization of functional amino groups. The examples mentioned at the beginning of the monomers are Homo - and copolymers of aminoalkylsilanes and methacrylates, such as N,N-dimethylaminoethylacrylate and methacrylate, vinylpyridine and vinylimidazole. To fit the comonomers aminecontaining monomers include, for example, amides Ethylenediamine carboxylic acids, N-vinylacetal and nitrogen, vinylsubstituted a heterocycle. Polymers, amino groups which can be obtained by polymeranalogous reaction of functional groups on the polymer, include the products of hydrolysis of polymers based on N-vinyl is s based Ethylenediamine NITRILES, for example, the hydrogenation products of Homo - and copolymers of Acrylonitrile and Methacrylonitrile.

Water-soluble polymers used in this invention have srednevekovoi molecular weight Mw of more than 500 up to 106Daltons. Preferably water-soluble polymers of the present invention have srednevekovoi molecular weight in the range from 1000 to 100000, preferably in the range of from 2000 to 50,000 and most preferably in the range of from 5,000 to 30,000 daltons. They are known to the specialist, they can be purchased in shopping online or using known methods.

Pursuant to this invention the preferred Homo - and copolymers of N-vinylacetate, especially N-vinylpyrrolidone. Among them, preferred Homo - and copolymers, especially the homopolymers with srednevekovym molecular weight in the range from 1000 to 100000, particularly in the range from 2,000 to 50,000 and most preferably in the range from 5000 to 30 000. Homo - and copolymers of N-vinylation sufficiently known to the expert, for example from Ullmann''s Encyclopedia of Indastrial Chemistry, 5thed, Vol A21, s.752-756, and Rompp, Chemielexikon, 9th. , Publishing house Georg-Thieme-Verlag, Stuttdard, 1989-1992, S. 3583 f., and literature cited therein (see also Davidson, Handbook of Water-Soluble Gum and Resins, McGraw-Hill, New-York-Londo is a means of processing the medium aqueous solution, containing at least one copper salt and at least one water-soluble polymer in the amount indicated above. The deposition is carried out so that copper is deposited on a solid oxide carrier, and the degree of oxidation of the precipitated copper more than zero.

Treatment of solid oxide carrier with an aqueous solution of salt of copper in the present invention may be implemented in radically different ways. When performing the present invention the solid oxide carrier impregnated with the aqueous copper salt solution containing water-soluble polymer is dried and repeat under certain conditions this process until you get the desired amount of copper. The impregnation can be carried out by wetting the solid oxide carrier with an aqueous solution of salt of copper boiling or fluidized bed. Suitable settings for these purposes are, for example, the drageeing boiler or pellet fluidized bed. Another way impregnation of solid oxide carrier is suspendirovanie it in an aqueous copper salt solution and the water-soluble polymer, filtering and drying (see below); if necessary this process can be repeated until you get the desired amount of copper.

In the implementation considered adiusaha funds. As a rule, do this as follows: solid oxide carrier is suspended in an aqueous solution containing at least one copper salt and at least one water-soluble polymer and then adding the precipitating agent. Needless to say, as a salt of copper, and water-soluble polymer can be added to the aqueous suspension of solid oxide carrier in the form of a solution, and solids. Pursuant to this invention it is important that the polymer and a salt of copper was added in dissolved form to make precipitating means in the aqueous dispersion medium. After deposition of the obtained solid (media besieged compound of copper) is filtered and dried. Under certain conditions, the obtained solid substance before drying washed with water or an organic solvent miscible with water, to remove excess precipitating means. The drying is generally conducted at temperatures above 100oWith at normal pressure. It can be done at a lower pressure, and under certain conditions, lower temperature. Drying time is usually from 1 to 48 hours. Drying temperature, as a rule, should not exceed 200o

Preferred precipitating means are aqueous solutions of water-soluble carbonates and hydroxides, such as aqueous solutions of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide. Most preferred as the precipitating funds are considered by aqueous solutions of sodium carbonate or potassium carbonate.

The deposition may be carried out at room temperature and at elevated temperatures. The deposition is carried out mainly at temperatures above 50oWith, especially if the besiegers tools use a carbonate or hydroxide. It is preferable to add the precipitating agent immediately, but over a longer period, mainly from 0.5 to 10 hours, before the comfort, typically, the media is selected from a ceramic oxide, such as silicon dioxide, for example silicic acid and silicic gels, silicates, aluminum silicates, aluminum dioxide, especially-aluminium oxide, zirconium dioxide and titanium dioxide or mixtures of these oxides, and zeolites and pumice. Preferred pursuant to this invention the material-carriers contain at least 80 wt.% silicon dioxide, for example, in the form of a silicon gel or silicic acid. Used according to the present invention, the oxide materials-the media have, as a rule, the specific BET-surface (specific surface area of the catalyst, measured by the method of brunauer, Emmett and teller) (measured according to German standard DIN 66131) of more than 30 m2/g, mostly above 50 m2/g and especially above 100 m2/, usually WET the surface does not exceed 600 m2/g and especially 500 m2/, Mainly as oxide material carrier using silicon dioxide having a BET surface in the range of 200-400 m2/,

Used in the present invention, aqueous solutions of salts of copper contain, as a rule, water-soluble salt of copper in a concentration of from 0.05 to 5 mol is copper, used for impregnation). However, this concentration is determined by the solubility of the copper salt or for practical reasons. Typical copper salts include copper acetate (II) chloride copper (II) sulfate copper (II) nitrate copper (II), and the corresponding hydrates of these salts. The concentration of the water-soluble polymer in these solutions is generally from 0.1 to 100 g/l, preferably from 0.5 to 50 g/l and most preferably from 1 to 10 g/L. the Ratio of copper to polymer is generally from 100:1 to 1:2, the preferred range is from 50: 1 to 1:1 and most preferred from 20:1 to 2:1 ratio (weight parts of copper to the polymer).

According to the present invention after a stage of processing of solid oxide material of the carrier with an aqueous solution of salt of copper should, under certain conditions, stage of calcination. The calcination occurs mainly at temperatures from 250 to 450oWith on the air or in the atmosphere of inert gas, preferably in a nitrogen atmosphere. The duration of calcination is generally from 1 to 24 hours.

The powder of the catalyst produced by the method of the present invention, as a rule, adding for tabletting auxiliary substances, puff products. As excipients for tableting you can use the usual auxiliary substances used for these purposes. For example, graphite, magnesium stearate, methylcellulose (as Walocel), copper powder or a mixture thereof. The molding bodies may occur before the process of calcination, and after it.

The copper content in the catalyst (calculated as metallic copper) take usually in an amount of from 0.01 to 50 weight. %, preferably from 2 to 30 weight. %, most preferably from 5 to 20 wt.% in terms of the total weight of the catalyst. Depending on the method of producing the catalysts of the present invention may contain up to 2 wt. % alkali metal, especially sodium or potassium. WET the surface (measured according to DIN 66131) of the catalyst is usually not less than 30 m2/g, preferably from 50 to 600 m2/g, most preferably from 100 to 500 m2/, Preferably from 200 to 400 m2/the Average size of the particles deposited on the catalyst carrier salt of copper pursuant to this invention is generally below 20 nm. The particle sizes determined, for example, by the method of transmission electron microscop consider the invention can be used for the dehydrogenation of secondary alcohols and obtain the corresponding ketones. In the case of secondary alcohols can talk about how the alcohols with an open circuit, and cycloalkane. The preferred eductae method of the present invention are alkanols and cycloalkanes with 3-14 carbon atoms. The most preferred adytum include cycloalkanes as Cyclopentanol, cyclohexanol, methylcyclohexanol and cyclododecanol. The catalysts of the invention under examination is most suitable for the dehydrogenation of cyclohexanol.

As doctow dehydrogenation can be used as a pure alcohols, and mixtures of different alcohols. Often also used a mixture of alcohol and the product of the dehydrogenation. As educt for the dehydrogenation of cyclohexanol is used, as a rule, a mixture of cyclohexanol and cyclohexanone. Of course, you can also use pure cyclohexanol. Commonly used mixture consists of from 50 to 100, preferably from 60 to 99, most preferably 96 weight. % of cyclohexanol and from 50 to 0, predominantly from 40 to 1, mostly 4 weight. % cyclohexanone. Cyclohexanone and cyclohexanol get usually by oxidation of cyclohexane with subsequent concentration of cyclohexanol by distillation, cyclohexanone and other easily and a temperature of from 180 to 400oC, preferably from 200 to 350oC, most preferably at a temperature of from 220 to 260oC. the Pressure is set as a rule in the range from 50 kPa to 5 MPa, primarily working at atmospheric pressure.

As a rule, before the reaction, the catalyst is activated with hydrogen (forming). The stream of hydrogen diluted with an inert gas, mostly nitrogen, at a certain temperature, mainly in the range from 120 to 300oC, is passed through the catalyst. The proportion of hydrogen in pampering gas usually continuously increased until the termination temperature changes.

In a preferred form of execution of the educt is passed in the gaseous state through the catalyst, and LHSV (Liquid Hourly Space Velocity-hour space velocity of the liquid) is mainly from 0.1 to 100 h-1preferably, from 0.1 to 20 h-1. The educt can be mixed with an inert gas such as nitrogen or steam. The product of the dehydrogenation can be processed in the usual way (as in the case of cyclohexanone, see for example German patent application DE-A 1296625 and DE-A 1443462) and carry out the further processing.

Then, in the preferred form of the invention from the reaction mixture, you is. For further response is beneficial to the reaction mixture was kept in the loop until, until you reach the desired conversion.

Compared to the catalysts used in industry, the catalyst of the present invention, due to its high activity, can be used at much lower temperatures, it is characterized by a short stage of formation, high selectivity and conversion, close to equilibrium. In addition, deactivation of the catalyst occurs after a significantly longer period of operation, in comparison with commonly used so far catalysts.

The catalyst of the invention under examination has a high ability to pelletizing, sufficient hardness, high turnover at low operating temperatures, high selectivity for cyclohexanol and the short period of inactivity.

Examples I. Obtaining catalysts of the present invention (example 1).

271 g of silica with a BET-surface 270 m2/g suspended in 1 l of deionized water. Add 5 g of polyvinylpyrrolidone (PVP Merck, order No. 7443, medium molecular weight of 25,000 g/mol) that extending t is at this temperature for 4 hours 3000 ml of concentrated aqueous solution of sodium carbonate to achieve a constant pH of about 9.6. Cooled to room temperature, the obtained dark-grey suspension was filtered and washed with 80 l of water.

Then the powder is dried for 16 hours at a temperature of 120oC. then conduct the process of calcination or calcining for 2 hours at a temperature of 300oC.

Elemental analysis of the obtained catalyst powder (atom-absorbing spectroscopy) gave the copper content of 15.1 wt.% (calculated as elemental copper) and 1.0 wt.% sodium (calculated as elemental sodium).

Study of catalyst powder using transmission electron microscopy showed that the diameter of the deposited particles of copper is mostly less than 10 nm.

100 g of the catalyst powder obtained in example 1, tabletirujut (diameter 20 mm, thickness 2 mm) with 3 g of graphite and 1 g of magnesium stearate. Then tablets push through a sieve with a width of holes 1 mm and pressed into tablets (diameter 5 mm and thickness 3 mm). Lateral pressure tablets is 36=4 n Lateral pressure is determined by the device Fa. Frank. Typen 81557.

Comparative example 1 133,93 g three-hydrate nitrate copper (II) and 200 g of silicon dioxide (WET surface 372 m2/g) are suspended in 1500 ml of distilled water. The suspension is heated to 80oC. At this tempeau add 4200 ml of 0.3 N aqueous solution of potassium hydroxide until reaching a constant pH of about 9.5. Under stirring for 4 hours to keep the temperature of the 90oC. Then gray-black, the catalyst was filtered and dried 8 hours at a temperature of 120oC. then conduct the calcination for 5 hours at a temperature of 300oC. Elemental analysis of the obtained powder catalyst (atom-absorbing spectroscopy) gave the copper content of 14.3 weight. % (calculated as elemental copper) and 3.3 weight. % potassium (calculated as elemental potassium).

Study of catalyst powder using transmission electron microscopy showed that the diameter of the deposited particles of copper is mainly to 150 nm.

Thus obtained catalyst powder with 1.5 g of graphite is pressed as described above in tablet thickness 5x4 mm, the Strength of lateral pressure tablets 60=8 n

II. Test of catalyst Test of the catalyst was carried out in a reactor with a diameter of 5 cm and a length of 60 cm, Each time with 200 ml of the catalyst from I to the reaction of activated hydrogen. The catalyst prior to the filing of the educt activated at a temperature of 120oWith 150 l of N2/h and 1.5 l of N2/H. When the temperature increased by more than 10oWith, stopped the flow of hydrogen. After that, the temperature gradually, 20oWith, povysiloThe catalyst was activated 150 l N2/h and 7.5 l H2/H. At the end of the process of activation of the catalyst was applied anal-anholonomy mixture (96% of cyclohexanol, 4% cyclohexanone), and LHSV was about 0.7 h-1. Through different periods of time spent gas chromatographic analysis of the products leaving the reactor.

The results are presented in the table.

The catalyst of the invention under examination already at more than 220oProvides conversion, close to equilibrium, while at the same time a very high selectivity greater than 99%. When this temperature is very slow deactivation of the catalyst, which is expressed only in a slight increase in temperature to preserve the conversion.

Claims

1. The method of obtaining oxide catalysts containing copper to oxidation more than zero for the dehydrogenation of secondary alcohols by treatment of solid oxide carrier with an aqueous solution containing at least one salt of copper, followed by calcination, and the copper is applied on the solid oxide carrier by deposition from aqueous solution using precipitating means, characterized in that modnyavyy copper ions, and selected from homopolymers of N-vinylpyrrolidone.

2. The method according to p. 1, characterized in that the deposition is carried out at temperatures above 50C.

3. The method according to one of the above paragraphs, wherein the oxide carrier has a BET-surface >50 m2/g, measured according to DIN-standard 66131.

4. The method according to one of the above paragraphs, wherein the oxide carrier contains at least 70 wt.% silicon dioxide, calculated on the total weight of the carrier.

5. The method according to one of the above paragraphs, wherein the copper is applied on the carrier in an amount of from 0.1 to 50 wt.% calculated on the total weight of the catalyst.

6. Catalyst for dehydrogenation of secondary alcohols containing copper to oxidation more than zero on solid oxide carrier, characterized in that it is obtained by the method according to one of the aforementioned items, and deposited on the carrier copper has an average particle size of less than 20 nm.

7. The method of dehydrogenation of cyclic secondary alcohols to the corresponding ketones, characterized in that the dehydrogenation is performed on the catalyst under item 6.

8. The method according to p. 7, wherein the secondary alcohol is a cyclohexane

 

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