Method of preparing modified platinum catalyst for enantioselective hydration of esters of alfa-ketocarboxylic acids

FIELD: chemistry.

SUBSTANCE: invention relates to production of catalysts and can be used in chemical industry and in production of medications. Described is method of preparing modified platinum catalyst for enantioselective hydration of esters of alfa-ketacarboxylic acids which includes impregnation of hexachloroplatinic acid from solution into pores of prepared carrier, as such supersewn polystyrene is used, by water-absorbing capacity from solution tetrahydrofurane : methanol : water with ratio 4:1:1, mixture of hexachlorplatinic acid and carrier is kept during 10-15 minutes mixed, after which it is dried at 70-75°C, washed with Na2CO3 solution with further reduction of hexachlorplatinic acid, filtering, washing and drying of catalyst and modification with cinchonidine solution.

EFFECT: reduction of time of catalyst preparation, increase of catalyst activity, enentioselectivity and stability.

4 cl, 1 tbl, 3 ex

 

The invention relates to the production of catalysts and can be used in the chemical industry and in the production of medicines.

Known method of preparing a catalyst for chemical processes enantioselective hydrogenation of esters of α-ketocarboxylic acids. The connection of the noble metals (Pt, Pd, Rh) impregnants into the pores of the carrier within 12-24 hours, then the catalyst is filtered off and dried. Before use the catalyst restore in a stream of hydrogen at high temperature and washed with a stream of gaseous nitrogen or helium to prevent ignition. Mass content of noble metal in the catalyst 5% [..Frago, M.J.Mendes, E.Jordao / J. of Molecular Catalysis A: Chemical - 2002 - Vol.179 - P.243-251; K.Balazsik, M.Bartok / J. of Catalysis - 2004 - Vol. 224 - P.463-472].

The disadvantages of the method include the need for preliminary recovery of the catalyst in a stream of hydrogen at high temperatures and subsequent cooling in a stream of nitrogen or helium to prevent ignition, and the necessity of applying high pressures or high temperatures.

The closest in technical essence is a method for preparing a modified platinum catalyst for the enantioselective hydrogenation of esters of α-ketocarboxylic acids, vkljuchajuwih the impregnation hexachloroplatinum acid from the solution into the pores of the prepared media keeping the mixture in solution, the recovery hexachloroplatinic acid, filtering, washing and drying of the catalyst, modified with a solution cinchonidine. As the carrier used To-10 montmorillonite (10M). Impregnation hexachloroplatinum acid into the pores TO-10M was performed from aqueous solution. This mixture was stirred for 12 hours at 25°C., then evaporated water. Impregnated hexachloroplatinum acid was recovered in 6:1 mixture of ethanol/ethylene glycol for 4 hours. After recovery of the catalyst was filtered and 3 times washed with ethanol and dried. Modification of the catalyst solution cinchonidine was carried suspendirovanie catalyst in 75% aqueous solution of ethanol with continuous stirring at 25°C for 24 hours. Then, the catalyst Pt/K-10(CD)IIwas filtered, washed three times with toluene and dried [Article: K.Balazsik, B.Török, G.Szakonyi, M.Bartok / Applied Catalysis A:General 1999 - Vol.182 - P.53-63]. The process of hydrogenation in toluene lasts from 22 to 48 hours, achieving 74% enantiomeric excess.

The disadvantages of this method are the long production cycle of the catalyst, for a long time modification of the catalyst. The resulting catalyst is a cortex platinum on the surface of the carrier and its near-surface layer, which reduces the efficiency of platinum. Listed under is the faultless result in lowering of processability and unnecessary energy consumption. Low activity.

The objective of the invention is to improve the manufacturability of the preparation of the active catalyst, allowing enantioselective hydrogenation of esters of α-ketocarboxylic acids with a high content of the target enantiomer, increasing its activity and enantioselectivity.

The technical result of the invention is to reduce the time of preparation of the catalyst, the increase in activity, enantioselectivity and stability of the catalytic system.

The task and the technical result is achieved by the fact that in the method of preparation of Pt catalysts for enantioselective hydrogenation of esters of α-ketocarboxylic acids, including impregnation hexachloroplatinum acid from the solution into the pores of the prepared media, keeping the mixture in solution, the recovery hexachloroplatinic acid, filtering, washing and drying of the catalyst, modified with a solution cinchonidine, according to the invention, as the carrier used supersewn polystyrene, before restoring the catalyst optionally washed with a solution of Na2CO3and then water, impregnation hexachloroplatinic acid is conducted according to the capacity of a solution of tetrahydrofuran: methanol: water in the ratio 4:1:1, the mixture solution hexachloroplatinic acid and the medium was incubated for 10 of the 15 minutes under stirring, after which additionally carry out the drying at 70÷75°C, the recovery hexachloroplatinic acid is carried tetrahydridoborate(III) sodium within 1÷2 hours, washed with water, dried at 70÷75°C, followed by washing the mixture of 4:1:1 tetrahydrofuran: methanol: water. Modification of the catalyst solution cinchonidine carried out in a three-component solvent tetrahydrofuran: methanol: water 4:1:1 ratio, after which the catalyst is dried at a temperature of 70÷75°C. the Preparation of the carrier is performed by washing the carrier with acetone, filtration and subsequent drying medium at a temperature of 60÷70°C.

The use of polymer grid - supersewn of polystyrene as a carrier allows you to distribute platinum not on the surface of the granules of the media, and in its volume, which in combination with the properties supersewn polystyrene, provides high availability of the platinum particles in the reaction. Application supersewn polystyrene as the carrier provides the durability of the catalyst in comparison with catalysts based on C, SiO2, Al2O3also allows you to increase the activity and stability of the catalytic system. Pre-treatment supersewn polystyrene acetone allows you to clean the polymer matrix from the remnants of a cross-linking agent used in EMA preparation of the polymer network, and other dietary fibers, and drying at 60-70°C allows to effectively remove residual acetone.

Additional washing of the catalyst before restoring solution of Na2CO3and then water is necessary to remove the Hcl formed during formation of the catalyst.

Impregnation hexachloroplatinum acid capacity of solution of tetrahydrofuran: methanol: water in the ratio 4:1:1 allows you to more effectively enter hexachloroplatinum acid in the amount of the polymer, due to the greater swelling of the PCA in this three-component solution. Conducting impregnation within 10÷15 minutes due to the speed of absorption of a solution polymer carrier, reducing the time of impregnation leads to incomplete absorption of the solution, and the increase does not give any advantages due to its complete absorption. Continuous stirring is necessary for uniform absorption of the solution in the whole volume of the polymer carrier.

Recovery hexachloroplatinum acid tetrahydridoborate(III) of sodium was carried out for 1÷2 hours, because the recovery less than 1 hour leads to incomplete recovery of platinum, and increase the recovery time of no advantage, due to the full recovery of platinum.

Washing the recovered catalyst in water was performed to remove OST the Cove reductant products and recovery of the catalyst surface, and washing the mixture of 4:1:1 tetrahydrofuran: methanol: water to remove possible residues of recovery in the amount of ATP.

Modification of the catalyst solution cinchonidine conducted in ternary solvent tetrahydrofuran: methanol: water 4:1:1 due to better swelling of the polymer in the mixture that enables you to evenly distribute the modifier volume of granules of the polymer and to achieve all of the platinum particles distributed therein. Modification time impregnation on capacity due to the speed of absorption of the solution into the polymer beads.

Drying at a temperature of 70-75°C enables the effective removal of components of the three-component solvent of tetrahydrofuran: methanol: water. Reducing the drying temperature increases the removal of components and the increase reduces the activity and enantioselectivity of the catalyst.

The process of preparation of the catalyst is as follows. The flask carrier, fill the flask with acetone and stirred for 1÷2 hours, after which the resulting suspension is filtered on a Buechner funnel and dried under vacuum in a closet at a temperature of 60÷70°C. In the thus prepared carrier make the solution hexachloroplatinic acid in a mixture of tetrahydrofuran:methanol:water in the ratio 4:1:1 and stirred for 10÷15 minutes Then the media, PR is powered hexachloroplatinic acid, dried in a Cabinet at a temperature of 70÷75°C for 2÷5 hours. Then treated with an aqueous solution of Na2CO3within 10÷15 minutes, then the catalyst is filtered off on a Buchner funnel and dried in a Cabinet at a temperature of 70÷75°C for 2÷5 hours. Recovery of the catalyst is carried out with a solution of tetrahydridoborate(III) sodium with stirring for 1÷2 hours, then filtered on a Buechner funnel, washed with water, dried at a temperature of 70÷75°C for 2÷5 hours, then washed with a mixture of tetrahydrofuran: methanol: water in the ratio 4:1:1 and dried in a Cabinet at a temperature of 70-75°C for 2-5 hours. The recovered catalyst is impregnated with a solution of a modifier (cinchonidine) tetrahydrofuran: methanol: water in the ratio 4:1:1 with stirring for 10÷15 minutes Then dried at a temperature of 70÷75°C and used in the enantioselective hydrogenation of esters of α-ketocarboxylic acids.

Example 1

The process of preparation of the catalyst was carried out as follows.

The preparation of the PCA was carried out as follows: the first stage in the flask was placed 1 g of the PCA, filled the flask with acetone and stirred for 2 hours, after which the resulting suspension was filtered on a Buechner funnel and dried under vacuum in a closet at a temperature of 65°C. the thus Prepared carrier was transferred into a flask. In the vessel was prepared 0.1 mo the e/l solution hexachloroplatinic acid in 3 ml of a mixture of tetrahydrofuran: methanol: water in the ratio 4:1:1. The resulting solution was transferred into a flask and was stirred for 10 minutes Then the carrier impregnated hexachloroplatinic acid, dried in a Cabinet at 70°C for 4 hours and transferred into the flask. In the vessel was prepared a solution of 1.3 mol/l Na2CO3in 12 ml of water and carried it into the flask with saturated hexachloroplatinum acid PCA. The contents were mixed for 12 minutes, after which the catalyst was filtered on a Buechner funnel and dried in a Cabinet at 70°C for 4 hours. Then the catalyst was placed in a flask. In the vessel was preparing the solution tetrahydridoborate(III) sodium and carried it into the flask. The resulting suspension was stirred for 1 hour, then was filtered on a Buechner funnel, washed with water, dried at 70°C for 2 hours, washed with a mixture of tetrahydrofuran: methanol: water in the ratio 4:1:1, prepared in a separate container, and dried in a Cabinet at 70°C for 4 hours. The recovered catalyst was transferred into a flask. In a separate container was prepared solution of modifier in a mixture of tetrahydrofuran:methanol:water in the ratio 4:1:1, bore him into the flask and was stirred for 10 minutes Then the contents of the flask were dried in a Cabinet at a temperature of 70°C and used in the enantioselective hydrogenation of esters of α-ketocarboxylic acids. The finished catalyst used in GI is rirovanie of atilirovanie in toluene in a thermostatted reactor at 25°C and excess hydrogen pressure of 1.5 MPa. At 100% conversion of the substrate enantioselectivity was 75%.

Example 2

Carried out analogously to example 1, with the difference that the temperature of the drying of the polymer 60°C drying temperature in the process of preparation of the catalyst at 75°C.

The finished catalyst used in the hydrogenation of atilirovanie in toluene in a thermostatted reactor at 25°C and excess hydrogen pressure of 1.5 MPa. At 100% conversion of the substrate enantioselectivity was 73%.

Example 3

Carried out analogously to example 1, with the difference that the drying temperature in the process of preparation of the catalyst was 72°C.

The finished catalyst used in the hydrogenation of atilirovanie in toluene in a thermostatted reactor at 25°C and excess hydrogen pressure of 1.5 MPa. At 100% conversion of the substrate enantioselectivity was 74%.

The resulting catalyst does not require dovolenkovania before use and retains its activity and enantioselectivity in repeated cycles.

The presented method of preparation of the catalyst can reduce the time spent on the preparation of the catalyst and to increase its activity and enantioselectivity and stability in repeated cycles. The resulting catalyst is characterized by a uniform distribution and availability of platinum across the grain of the catalyst, unlike the prototype, which JW is aetsa catalyst cortical type, and allows more efficient use of the active phase of the catalyst.

The synthesis of the catalyst of the prototype is about 40 hours, while the catalyst can be synthesized in less than 20 hours.

More than an order of magnitude less time to reach 100% conversion under the same conditions compared with the prototype shows that the catalyst is more active than the prototype.

The proposed method can be widely applied for the synthesis of catalysts suitable for the process of fine organic synthesis.

Comparative characteristics of activity and enantioselectivity
CatalystPt, wt.%TimeConversion, %The enantiomeric excess, %
Pt/K-10(CD)IIa)57920010075
the placeholder
Pt/PCA(CD)b) 5120010075
example 1
Pt/PCA(CD)b)5120010073
example 2
Pt/PCA(CD)b)5120010074
example 3
(a) the Conditions of the experiment P(H2) 20 ATM, T 25°C, toluene 5 ml, catalyst - 0,100 g modifier is included in the catalyst composition; the substrate etherpiraat - 0,25 ml
B. the Conditions of the experiment P(H2) 15 ATM, T 25°C, toluene 20 ml, catalyst - 0,100 g modifier is included in the composition of the catalyst, the substrate etherpiraat - 0,25 ml

This invention is in the stage of laboratory research.

1. The method of preparation of the modified platinum catalyst for the enantioselective hydrogenation of esters of α-ketocarboxylic acids, including impregnation hexachloroplatinum acid from the solution into the pores of the prepared media, keeping the mixture in solution, the recovery hexachloroplatinic acid, filtering, washing and drying of the catalyst, modified with a solution cinchonidine, characterized in that as the carrier is used supersewn polystyrene, before restoring hexachloroplatinic acid catalyst optionally washed with a solution of PA2CO3and then water, impregnation hexachloroplatinic acid is conducted according to the capacity of a solution of tetrahydrofuran: methanol: water in the ratio 4:1:1, the mixture solution hexachloroplatinic acid and the medium was incubated for 10÷15 min with stirring, after which additionally carry out the drying at 70÷75°C.

2. The method according to claim 1, characterized in that the recovery hexachloroplatinic acid is carried tetrahydridoborate(III) sodium within 1÷2 h, washed with water and optionally dried at 70÷75°C, then washed with a mixture of 4:1:1 tetrahydrofuran: methanol: water.

3. The method according to claim 1, characterized in that the modification of the catalyst the solution cinchonidine carried out in a solvent of tetrahydrofuran: methanol: water 4:1:1 ratio, then the catalyst is dried at a temperature of 70÷75°C.

4. The method according to claim 1, characterized in that the preparation of the carrier is performed by washing it with acetone, filtration and subsequent drying medium at a temperature of 60÷70°C.



 

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