Method for preparing Salen Ni

A technology of salicylaldehyde and Schiff base, which is applied in the preparation of Salen Ni and the field of one-pot preparation of chiral catalysts, which can solve the problem of increasing "three wastes" and raw material consumption, increasing operation steps and solvent consumption, and "three wastes" treatment capacity Major problems, to achieve the effect of simplifying the post-processing equipment, reducing the generation of by-products and improving the purity

Active Publication Date: 2013-11-06
CHEM TECH ACAD OF SHANDONG PROVINCE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction virtually increases the amount of operation steps and solvents, which in turn increases the consumption of "three wastes" and raw materials
[0006]Because the existing methods for synthesizing Salen Ni have problems such as cumbersome process routes, serious environmental pollution, and a large amount of "three wastes" to be processed, industrial production is limited, so there is an urgent need for a A new technology to solve the existing problems to meet the market demand

Method used

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  • Method for preparing Salen Ni
  • Method for preparing Salen Ni
  • Method for preparing Salen Ni

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Add 22.8 g of chiral cyclohexanediamine and 100 mL of dichloromethane into a 1000 mL single-necked bottle, and add 93.6 g of 3,5-di-tert-butyl salicylaldehyde dichloromethane dropwise at -20°C in 200 mL , 1.5 hours to drop, after the end of the drop, keep warm for 2 hours, add 49.6 grams of nickel acetate tetrahydrate aqueous solution (2.0 mol / L) 100mL, react at room temperature for 12 hours, separate the reaction mixture after the reaction, and wash with 30 mL of dichloromethane The aqueous phase was combined with the organic phase, and the solvent was distilled off to obtain a crude product. The crude product was recrystallized from pure ethanol to obtain a reddish-brown Salen Ni solid powder with a yield of 86%. The purity of the sample was greater than 99% as measured by specific rotation.

Embodiment 2

[0029] Add 22.8 g of chiral cyclohexanediamine (RR type) and 100 mL of dichloromethane into a 1000 mL single-necked bottle, and add 70.2 g of 3,5-di-tert-butyl salicylaldehyde dichloride dropwise at -20 °C 200 mL of methane solution, drop it in 1.5 hours, keep it warm for 2 hours after the addition, add 49.6 grams of nickel acetate tetrahydrate aqueous solution (2.0 mol / L) 100 mL, react at room temperature for 12 hours, separate the reaction mixture after the reaction, 30 mL The aqueous phase was washed with dichloromethane, the organic phase was combined, and the solvent was distilled off to obtain a crude product. The crude product was recrystallized from pure ethanol to obtain a reddish-brown Salen Ni solid powder with a yield of 87%. The purity of the sample was greater than 99% as determined by specific rotation.

Embodiment 3

[0031]Add 22.8 g of chiral cyclohexanediamine (R R type) and 100 mL of dichloromethane into a 1000 mL single-necked bottle, and add 93.6 g of 3,5-di-tert-butyl salicylaldehyde dichloride dropwise at -20 °C 200 mL of methane solution, drop it in 1.5 hours, keep it warm for 2 hours after the addition, add 100 mL of 24.8 g nickel acetate tetrahydrate aqueous solution (1.0 mol / L), react at room temperature for 12 hours, separate the reaction mixture after the reaction, 30 mL The aqueous phase was washed with dichloromethane, the organic phase was combined, and the solvent was distilled off to obtain a crude product. The crude product was recrystallized from pure ethanol to obtain a reddish-brown Salen Ni solid powder with a yield of 41%. The purity of the sample was greater than 99% as determined by specific rotation.

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Abstract

The invention discloses a method for preparing salen Ni. The method comprises the following steps of: reacting cyclohexane diamine and salicylide or a salicylide derivative in an organic solvent to generate a Schiff alkali ligand; reacting by adding a nickel acetate aqueous solution; carrying out coordination on Ni2+ and Schiff alkali; taking organic phase of the obtained final reaction liquid; obtaining a salen Ni crude product by removing the solvent; and re-crystallizing the crude product to obtain the salen Ni. According to the method disclosed by the invention, the proper solvent and reaction condition can be selected; process parameters are optimized; post-processing equipment is greatly simplified; the cost is reduced; the generated by-products are reduced; the product purity is increased; compared with the prior art, the process route is simplified; the three wastes (waste gas, waste water and industrial residue) can be reduced; and the method is more advantageous for industrial implementation.

Description

technical field [0001] The invention relates to a method for preparing a chiral catalyst by a one-pot method, in particular to a method for preparing Salen Ni, which belongs to the technical field of organic synthesis. Background technique [0002] In 1864, Professor H. Schiff reported for the first time the condensation reaction of primary amines and carbonyl compounds to form a product with an imine group, which was later called Schiff base (Chinese translation name Schiff base, Schiff base, etc.). If two identical aldehyde molecules and one diamine molecule are polycondensed, the resulting chelating schiff base N,N'-disalicylaldehyde ethylenediamine is generally abbreviated as Salen. The Salen-type schiff base complex is an important class of coordination compounds, because its basic structure contains a C=N structure, and the N atom on its hybrid orbital has a lone pair of electrons, so it is endowed with important chemical and biological meaning. [0003] Salen coordi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/02C07C251/24
Inventor 高爱红岳涛刘丽秀柳泽岳张立东曹波
Owner CHEM TECH ACAD OF SHANDONG PROVINCE
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