Supported metal palladium catalyst, its preparation and its application

A metal palladium, supported technology, applied in the dynamic kinetic resolution of secondary alcohols, supported metal palladium catalyst and its preparation, can solve the problems of restricting wide application, cumbersome post-processing steps, and difficult separation of products in homogeneous catalytic systems , to achieve the effect of cost reduction and efficient splitting

Inactive Publication Date: 2012-11-21
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the use of homogeneous organometallic catalysts as racemic catalysts has high catalytic efficiency, there are always problems such as difficult product separati...

Method used

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  • Supported metal palladium catalyst, its preparation and its application
  • Supported metal palladium catalyst, its preparation and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] (1) Under the protection of an inert gas, add 75 mg (0.246 mmol) of palladium acetylacetonate into 15 mL of oleylamine, stir until dissolved; heat the above solution to 60 °C within 10 minutes with a 4 °C / min program. Dissolve 300 mg (3.46 mmol) tert-butylamine borane in 3.5 mL oleylamine and quickly pour into the above palladium salt solution. The solution was programmed at 3°C / min to 90°C and then held at 90°C for 60 minutes. After cooling to room temperature, 30 mL of absolute ethanol was added, and the product was centrifuged at 8000 rpm and dispersed in 125 mL of n-hexane.

[0020] (2) Impregnate 0.3g of mesoporous silica SBA-15 with 50mL of metal palladium solution (containing 10mg of palladium) in Step 1 at 25°C, ultrasonically at 30W for 2 hours, centrifuge at 8000rmp, wash with ethanol, and vacuum dry at 90°C4 Hour.

[0021] (3) Add 20 mL of toluene to the product in step 2, add 2.5 mL of methyltriethoxysilane, and heat to reflux at 70° C. for 10 hours to obt...

Embodiment 2

[0025] The catalyst described in Example 1 is combined with biological enzymes for dynamic kinetic resolution of secondary alcohols. Namely: 0.5 mmol of racemic phenylethyl alcohol, 5 mL of n-hexane, 60 mg of supported metal palladium catalyst, 100 mg of Novozym 435 biological enzyme and 1.5 mmol of ethylene acetate were added to a 10 mL reaction kettle. Fill and discharge 4-5 times with 5% hydrogen-argon mixed gas to replace the air in the reactor, and finally control the partial pressure of hydrogen in the reactor to 0.03MPa. The reactor was placed in an oil bath at 70°C for 12 hours, cooled to room temperature, centrifuged, and the supernatant was filtered with a 0.2 μm filter head for chromatographic analysis. An ester of 98% conversion, 99.5% optical purity and 99% chemical purity was obtained.

Embodiment 3

[0027] (1) Under the protection of inert gas, add 75mg (0.246mmol) palladium acetylacetonate into 20mL oleylamine, stir until dissolved; heat the above solution to 60°C within 10 minutes at 4°C / min. Dissolve 300 mg (3.46 mmol) tert-butylamine borane in 3.5 mL oleylamine and quickly pour into the above palladium salt solution. The solution was programmed at 3°C / min to 90°C and then held at 90°C for 60 minutes. After cooling to room temperature, 30 mL of absolute ethanol was added, and the product was centrifuged at 8000 rpm and dispersed in 125 mL of n-hexane.

[0028] (2) Impregnate 0.3g of carrier mesoporous silica SBA-15 with 50mL of step 1 metal palladium solution (containing 10mg of palladium) at 25°C, ultrasonicate at 30W for 2 hours, centrifuge at 8000rmp, wash with ethanol, and vacuum dry at 90°C 4 hours.

[0029] (3) Add 20 mL of toluene to the product in step 2, add 2.5 mL of methyltriethoxysilane, and heat to reflux at 70° C. for 10 hours to obtain a supported meta...

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Abstract

The invention discloses a supported metal palladium catalyst, its preparation method and its use. The metal loading amount of the catalyst is 1.0-5.0wt%, the specific surface area of the catalyst is 300-900m<2>/g, the pore volume of the catalyst is 0.3-1.0cm<3>/g, the pore diameter of the catalyst is 3.0-10.0nm, and the metal particle diameter of the catalyst is 1.0-8.0nm. In the invention, the preparation of the high-stability metal catalyst with uniform and controllable dimension is realized through a three-step method. The supported metal palladium catalyst can be used for the dynamic kinetic resolution of a secondary alcohol through combining with a lipase, and the catalytic performance of the supported metal palladium catalyst is further better than that of supported metal palladium catalysts prepared through traditional dipping reduction methods. The supported metal palladium catalyst has the advantages of realization of the efficient resolution of the secondary alcohol in a one-pot reaction system, multiple repeated use, and substantial cost reduction.

Description

technical field [0001] The invention relates to the field of catalysts, in particular to a supported metal palladium catalyst, a preparation method thereof and the use of combining biological enzymes for dynamic kinetic resolution of secondary alcohols. Background technique [0002] Chiral compounds are widely used in related fields such as medicine, pesticide and biology. There are huge differences in the pharmacological effects of chiral compounds with different configurations. How to obtain chiral compounds with a single isomer has become a research hotspot for chemical researchers in various countries. At present, kinetic resolution is the most important method to obtain chiral compounds of single isomer, but its theoretical maximum conversion rate is only 50%. In 1997, Stürmer designed a reaction system for the efficient resolution of chiral compounds combining transition metal complexes and biological enzymes, that is, dynamic kinetic resolution technology. This meth...

Claims

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Application Information

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IPC IPC(8): B01J29/03C12P41/00C12P7/62
Inventor 李辉胥元峰
Owner SHANGHAI NORMAL UNIVERSITY
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