Chiral schiff base-metal heterogeneous epoxidation catalyst and its prepn. method

A technology of oxidation catalysts and Schiff bases, applied in the direction of physical/chemical process catalysts, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., can solve complex catalyst preparation, loss, activity and ee value Poor problems, easy to purify, easy to prepare, easy to handle and operate

Inactive Publication Date: 2006-11-29
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

Although the early literature [Chem.Rev.102 (2002) 3495; Chem.Soc.Rev.33 (2004) 108] reviewed many heterogeneous catalysts prepared by immobilizing Mn(salen), these catalysts are often relatively complicated to prepare , the obtained activity and ee value are relatively poor in homogeneity, and accompanied by a certain loss phenomenon, there is still a certain gap from industrial application

Method used

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  • Chiral schiff base-metal heterogeneous epoxidation catalyst and its prepn. method
  • Chiral schiff base-metal heterogeneous epoxidation catalyst and its prepn. method

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Experimental program
Comparison scheme
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Embodiment 1

[0045] (1) 3 grams of MCM-41 (pore size 1.6nm) was heated and vacuum-treated by adding 150ml of anhydrous toluene and 6ml of HS (CH 2 ) 3 Si(OMe) 3 , Grafted at 120°C for 18h, then filtered, washed and dried.

[0046] (2) Then use 30% H 2 o 2 27ml of the precursor obtained in oxidation step 1 for 24h, add 0.33g NaHCO after filtering and washing 3 20ml of aqueous solution was reacted at room temperature for 3h, filtered, washed and dried.

[0047] (3) the complex (1.0mmol, wherein R 1 =t-Bu,R 2 =t-Bu,R 3 =Ph, chiral ortho-diamine in (1S,2S) configuration, metal =Mn) for 5 hours. The number of heterogeneous catalysts that can be prepared is A.

Embodiment 2

[0049] Same as Example 1, except that step 1 is changed: the carrier adopts an organic-inorganic hybrid material containing propane mercapto group [synthesis details see Micro.Meso.Mater.77 (2005) 257], and step 3 uses Complexes of M(salen) (where R 1 =t-Bu, R 2 =t-Bu, R 3 =-(CH 2 ) 4 -, the chiral adjacent diamine is (1R, 2R) configuration, M=Mn), and the heterogeneous catalyst number of making is B.

Embodiment 3

[0051] (1) Add 150ml of anhydrous toluene and 7ml of PhSi(OEt) to 3 grams of SBA-15 (pore size 7.6nm) after heating and vacuum treatment 3 , Grafted at 120°C for 18h, then filtered, washed and dried. (2) Heat and vacuum the precursor obtained in step 1, add 10 ml of concentrated sulfuric acid for sulfonation at 100 degrees for 8 hours, then filter, wash and dry. Then with 0.33g NaHCO 3 20ml of the aqueous solution was reacted at room temperature for 3 hours, then filtered, washed and dried. (3) the catalyst precursor obtained in step 2 is refluxed in the ethanol of 60ml to graft the complex of M (salen) (1.0mmol, wherein R 1 =t-Bu, R 2 =t-Bu, R 3 =-(CH 2 ) 4 -, chiral ortho-diamine is (1S, 2S) configuration, M=Mn) the heterogeneous catalyst that can be prepared in 5 hours, numbering is C.

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Abstract

A multi-phase epoxidizing catalyst with high activity, chiral selectivity and stability, and short reaction time is prepared through using sulfonyl group to axially fix the complex of the chiral Schiff base and metal to inorganic carrier and / or polymer carrier.

Description

technical field [0001] The invention relates to a chiral Schiff base-metal epoxidation catalyst, in particular to a chiral heterogeneous epoxidation catalyst through which a sulfonic acid group axially supports a chiral Schiff base-metal. [0002] The present invention also relates to a method for preparing the above-mentioned catalyst. Background technique [0003] In the past ten years, people's demand for single-enantiomer chiral compounds is huge and increasing year by year. This demand is mainly reflected in the fields of medicine, pesticides and fine chemicals. Among them, chiral epoxides can obtain a large number of different types of chiral compounds through asymmetric ring opening and functional group transformation, so the synthesis of chiral epoxides has attracted much attention, and the chiral epoxides of chromene derivatives are A very important class of intermediates used in the synthesis of drugs for the treatment of hypertension [US5,352,814; US 5,639,889]. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07F13/00
CPCY02P20/50
Inventor 李灿张慧东张艳梅
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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