Chirality diamine-metallic complex polyphase catalyzer as well as preparation method and application

A technology of metal complexes and heterogeneous catalysts, applied in the direction of organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, catalyst supports, etc., to achieve high activity, chiral selectivity, high stability, easy to prepare effects

Inactive Publication Date: 2008-05-14
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The use of magnetic nanoparticles to recover and recycle chiral metal complex catalysts has also begun to develop abroad in the last three years [J.Am.Chem.Soc.127(2005)12486; J.Am.Soc.Chem.128(2006 )5279], but there is no such work in China

Method used

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  • Chirality diamine-metallic complex polyphase catalyzer as well as preparation method and application
  • Chirality diamine-metallic complex polyphase catalyzer as well as preparation method and application
  • Chirality diamine-metallic complex polyphase catalyzer as well as preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1: Preparation of chiral diamine-metal complex heterogeneous catalyst

[0074] 1) Preparation of water-soluble magnetic fluid

[0075] 1.25g FeCl 3 ·6H 2 O and 0.46FeCl 2 4H 2 O was dissolved in 75ml of degassed deionized water, and the temperature was raised to 80°C under the protection of argon. Under vigorous mechanical stirring, 19ml of 28% ammonia water was quickly injected and kept for 20min. Cool down to room temperature, wash with deionized water to neutrality, add 0.45g dopamine hydrochloride, and ultrasonicate for 30min to obtain a water-soluble magnetic fluid with an average particle size of 10-15nm (see figure 1 ).

[0076] 2) Preparation of oil-soluble magnetic fluid

[0077] Same as step 1. 1.25g FeCl 3 ·6H 2 O and 0.46FeCl 2 .4H 2 O was dissolved in 75ml of degassed deionized water, and the temperature was raised to 80°C under the protection of argon. Under vigorous mechanical stirring, 19ml of 28% ammonia water was quickly injected a...

Embodiment 2

[0083] Example 2: Heterogeneous catalysts for asymmetric hydrogen transfer reactions

[0084]Add 0.5mmol acetophenone, 340mgNaCOOH to the heterogeneous catalyst prepared in embodiment 1 step 6 and react at 40°C. After the reaction, remove the solid catalyst with magnet adsorption (see image 3 ), the filtrate was purified by column chromatography and analyzed by gas chromatography for conversion and enantioselectivity (full methylated β-cyclodextrin chiral capillary column), the results are shown in Table 1.

Embodiment 3

[0085] Embodiment 3: heterogeneous chiral catalyst is used for asymmetric hydrogen transfer reaction of acetophenone

[0086] The heterogeneous catalyst prepared in embodiment 1, add 0.5mmol acetophenone, 0.13ml HCOOH, 0.37ml Et 3 N was reacted at 40°C, and the results are shown in Table 1.

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Abstract

The invention discloses a polyphase catalyst and a preparation method for a chiral diamine and metal complex: (a) preparing magnetic nanometer particles using common sedimentation method; (b) adding stabilizing agent to the magnetic nanometer particles prepared in the step a; the stabilizing agent is aryl compoundiarylide comprising ortho bisphenol substituent, polyethylene pyrrolidone, and C15 to C18 alkyl or olefin carboxylic acid; (c) covering the surface of the magnetic nanometer particles got from the step b with a carrier using sol gel method, the carrier is inorganic material or organic inorganic hybrid hole wall material; (d) solidified carry the surface of the product prepared from the step c with chiral diamine; (e) dissolving the product prepared from the step d, adding metal predecessor material, and then obtaining the target product. The method for the polyphase catalyst of the invention is simple and convenient operation. Using the magnet to absorb, easy recovery and recycling for the catalyst can be easily achieved. The invention has an advantage that the catalyst can still maintain the activity and chiral selectivity through a plurality of circulation.

Description

Technical field [0001] The present invention relates to a heterogeneous catalyst, in particular, to a heterogeneous catalyst that immobilizes and recovers chiral diamine-metal complexes through magnetic nanoparticles. [0002] The present invention also relates to a method for preparing the above heterogeneous catalyst. [0003] The present invention also relates to the use of the above heterogeneous catalyst in asymmetric hydrogen transfer reactions. Background technique [0004] In recent years, people's demand for single-enantiomer chiral compounds has been huge and has been increasing year by year [Chem.&Eng.News.79(2001)79]. Optically active alcohols and amines are important intermediates in the fields of medicine, pesticides and fine chemicals. Optically active alcohols and amines can be prepared by reduction of ketone and imine functional groups, respectively. In the early days, it was prepared by hydrogenation of chiral phosphine ligands [Chem.Rev.103(2003)3029]. ...

Claims

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Application Information

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IPC IPC(8): B01J31/22B01J31/28B01J32/00C07B35/02
CPCY02P20/50Y02P20/584
Inventor 李灿李军张艳梅
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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