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Preparation method of chiral POMOFs

A chiral, selected technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., to achieve simple synthesis, low price, good conversion rate and stereoselectivity Effect

Active Publication Date: 2015-12-16
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, catalysts capable of directly preparing chiral cyclic carbonates from simple alkenes in one step through cascade reactions under mild conditions have not been reported.

Method used

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  • Preparation method of chiral POMOFs
  • Preparation method of chiral POMOFs
  • Preparation method of chiral POMOFs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Na 4 W 10 o 32 ·8H 2 O (130mg, 0.05mmol), Zn (NO 3 ) 2 ·6H 2 O (29.8mg, 0.1mmol), 3-amino-4,4'-bipyridine (34.2mg, 0.2mmol) and L-N-tert-butoxycarbonyl-2-imidazole-1-pyrrolidine (25.0mg, 0.1mmol) Dissolve in a mixed solution of water (6.0mL) and acetonitrile (2.0mL) and use 1mol·L -1 HCl adjusted the pH value of the solution to 3.6, stirred evenly, placed in an oven, fired at 130°C for 72h, closed the oven, cooled to room temperature, colorless rod-shaped crystals were produced, filtered, and dried to obtain the target material POMOF (catalyst ZnW- PYI1), yield about 68%. Elemental analysis (%) for C 40 h 54 N 14 o 41 W 12 Zn 3 : C12.68, H1.44, N5.18, Zn5.18, W58.22; Found: C12.64, H1.41, N5.20, Zn5.22, W58.24.IR(KBr): 3440( s), 3123(w), 1619(s), 1532(s), 1247(s), 1103(w), 938(s), 872(s), 756(vs)cm-1 Table 1 shows the reaction performance test of the material in Example 1 asymmetrically catalyzing the one-pot synthesis of cyclocarbonate from olefins.

Embodiment 2

[0029] Na 4 W 10 o 32 ·8H 2 O (130mg, 0.05mmol), Zn (NO 3 ) 2 ·6H 2 O (29.8mg, 0.1mmol), 3-amino-4,4'-bipyridine (34.2mg, 0.2mmol) and D-N-tert-butoxycarbonyl-2-imidazole-1-pyrrolidine (25.0mg, 0.1mmol) Dissolve in a mixed solution of water (6.0mL) and acetonitrile (2.0mL) and use 1mol·L -1 HCl adjusted the pH value of the solution to 3.6, stirred evenly, placed in an oven, fired at 130°C for 72h, closed the oven, cooled to room temperature, colorless rod-shaped crystals were produced, filtered, and dried to obtain the target material POMOF (catalyst ZnW- PYI2), yield about 68%. Elemental analysis (%) for C 40 h 54 N 14 o 41 W 12 Zn 3 : C12.68, H1.44, N5.18, Zn5.18, W58.22; Found: C12.64, H1.42, N5.17, Zn5.20, W58.25 for ZnW-PYI2.IR(KBr): 3443(s), 3124(w), 1618(s), 1531(s), 1248(s), 1104(w), 939(s), 873(s), 757(vs)cm -1 Table 1 shows the reaction performance test of the material in Example 2 asymmetrically catalyzing the one-pot synthesis of cyclocarbonate from ...

Embodiment 3

[0031] Na 4 W 10 o 32 ·8H 2 O (130mg, 0.05mmol), NiCl 2 ·6H 2 O (23.8mg, 0.1mmol), 2,4,6-Tri-pyridin-4-yl-[1,3,5]triazine (31.2mg, 0.1mmol) and L-N-tert-butoxycarbonyl-2-imidazole- 1-Pyrrolidine (25.0mg, 0.1mmol) was dissolved in a mixed solution of water (4.0mL) and acetonitrile (2.0mL) and mixed with 1mol·L -1 HCl adjusted the pH value of the solution to 4.0, stirred evenly, placed in an oven, fired at 130°C for 72h, closed the oven, cooled to room temperature, light green massive crystals were produced, filtered, and dried to obtain the target material POMOF (catalyst NiW -PYI3), yield about 45%.

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Abstract

The invention relates to the technical field of chiral catalytic materials, and relates to a preparation method of chiral POMOFs. The POMOFs with a tunnel structure are prepared through a hydrothermal technology with L-BCIP or D-BCIP as a chiral source, L as a functional connecting ligand, polyoxometallate (POM) as an oxidation catalysis function group, and Ni<2+>, Cu<2+>, Co<2+> or Zn<2+> in a transition metal salt TM as a node. The above catalyst has the advantages of simple synthesis, easy operation, low price of catalysis reaction raw materials, high yield, controllable preparation of two enantiomers, and easy large-area popularization application. Multiple catalysis site synergistic catalysis makes the catalysis reaction have very good conversion rate and stereoselectivity under a catalysis dosage, so the catalyst is suitable for industrial large-scale production demands, and has very good industrial prospect.

Description

technical field [0001] The invention relates to a preparation method of chiral POMOFs, belonging to the technical field of chiral catalytic materials. Background technique [0002] Cyclocarbonate is a class of excellent aprotic polar solvents, and is an important intermediate and chemical raw material in organic synthesis. It can be further reacted to synthesize a large number of useful materials such as bishydroxycarbonate, urea, polymers, etc., in It occupies an extremely important position in the production of fine chemicals and is widely used in fields such as fine chemicals, engineering plastics, antiknock agents and lithium battery electrolytes (such as propylene carbonate). Especially optically active cyclic carbonates are used as precursors and intermediates of medicines, pesticides, spices and functional materials. From an environmental and economic point of view, CO 2 It is cheap, non-toxic and non-flammable, and can be used as a ready-made C 1 The building bloc...

Claims

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Application Information

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IPC IPC(8): B01J31/22B01J35/02C07D317/36
Inventor 段春迎韩秋霞何成祁波史岽瑛
Owner DALIAN UNIV OF TECH
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