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Preparation method and application of adjustable metal organic cage compound for efficiently selective catalytic reduction of nitrobenzaldehyde

A technology of nitrobenzaldehyde and cage compounds, which is applied in the preparation of organic compounds, iron group organic compounds without C-metal bonds, 2/12 groups of organic compounds without C-metal bonds, etc., can solve environmental pollution , the selectivity needs to be improved, etc., to achieve the effect of low price, high yield and stable chemical properties

Inactive Publication Date: 2019-11-22
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The process of this method is relatively simple, the production cost is low, but the selectivity needs to be improved, and in addition, it will cause certain pollution to the environment

Method used

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  • Preparation method and application of adjustable metal organic cage compound for efficiently selective catalytic reduction of nitrobenzaldehyde
  • Preparation method and application of adjustable metal organic cage compound for efficiently selective catalytic reduction of nitrobenzaldehyde
  • Preparation method and application of adjustable metal organic cage compound for efficiently selective catalytic reduction of nitrobenzaldehyde

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of embodiment 1 compound Fe-FPB

[0030] Methyl propargyl (1.68g, 20mmol), benzaldehyde (1.06g, 10mmol) and 2-furylamine (1.13g, 10mmol) were added to 2.0 ml of glacial acetic acid, stirred at 80°C for 20 Hour. The reaction solution was cooled and 25 ml of ethanol was added, sonicated until the solid was powdered, filtered with suction and washed with ethanol to filter the obtained filter cake, and the washed filter cake was vacuum-dried to obtain 1.78 g of a light yellow solid with a yield of 51.8%. 1 H NMR (400MHz, CDCl 3 ,ppm): δ7.51(s,2H),7.46(s,1H),7.18(m,3H),7.10(m,2H),6.49(s,1H),6.43(s,1H),4.82( s,2H),4.70(s,1H),3.53(s,6H). 13 C NMR (101MHz, CDCl 3 ,ppm)δ167.3,149.3,146.3,143.6,137.4,128.2,128.1,126.6,110.8,109.3,109.2,51.4,51.1,37.3.ESI-MS calcd for C 20 h 19 NO 5 353.1263,found 354.1337[M+H] + ,376.1150[M+Na] + . After mixing the pale yellow solid (1.76 g, 5 mmol) with 210 mmol of hydrazine hydrate, the mixture was stirred under reflux...

Embodiment 2

[0031] The preparation of embodiment 2 compound Co-FPB

[0032] Co(BF 4 ) 2 ·6H 2 O (34.0mg, 0.10mmol) and the ligand H prepared in Example 1 2 FPB (53.2 mg, 0.10 mmol) was dissolved in 30 ml of dichloromethane and acetonitrile in a mixed solvent with a volume ratio of 1:4, stirred at room temperature for 4 hours, after stirring and filtering, diethyl ether was diffused into the filtrate, and after 2 weeks at room temperature A solid precipitated out of the solution to obtain 27.4 mg of the target compound Co-FPB with a yield of 36%. ESI-MS:m / z:785.4830[H 3 co 4 (FPB) 4 ] 3+ ,1177.6599[H 2 co 4 (FPB) 4 ] 2+ ,1231.2565[H 3 co 4 (FPB) 4 ·BF 4 ] 2+ . The structure crystal diagram of compound Co-FPB, such as image 3 Shown, the solution ESI-MS high-resolution mass spectrum of compound Co-FPB, such as Figure 4 shown.

Embodiment 3

[0033] The preparation of embodiment 3 compound Ni-FPB

[0034] Ni(ClO 4 ) 2 ·6H 2 O (36.5mg, 0.10mmol) and the ligand H prepared in Example 1 2 FPB (53.2 mg, 0.10 mmol) was dissolved in 30 ml of dichloromethane and acetonitrile in a mixed solvent with a volume ratio of 1:7, stirred at room temperature for 4 hours, after stirring and filtering, diethyl ether was diffused into the filtrate, and after 2 weeks at room temperature A solid precipitated out of the solution to obtain 42.7 mg of the target compound Ni-FPB with a yield of 56%. ESI-MS:m / z:785.1693[H 3 Ni 4 (FPB) 4 ] 3+ ,1177.2492[H 2 Ni 4 (FPB) 4 ] 2+ . The structural crystal diagram of the compound Ni-FPB, such as Figure 5 Shown, the solution ESI-MS high-resolution mass spectrum of compound Ni-FPB, such as Figure 6 shown.

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Abstract

The invention belongs to the technical field of fine chemical engineering. The invention relates to a preparation method and application of an adjustable metal organic cage compound for efficient selective catalytic reduction of nitrobenzaldehyde. According to the preparation method, M<2+> in a transition metal salt is used as a node and L is used as a ligand for reaction to prepare the metal organic cage compound, and the synthetic route is as follows: M<2+> + L- to M-L; wherein the ligand L is selected from H2FPB; the transition metal salt is selected from one of ferrous perchlorate, cobalttetrafluoroborate, nickel perchlorate or zinc tetrafluoroborate. The metal organic cage compound prepared by the method is low in raw material price and high in yield, and the obtained compound is stable in chemical property and easy to put into practical application. As a target compound M-FPB, the adjustable metal organic cage compound shows that the selectivity of the compound M-FPB can reach 99% in the aspects of reduction of p-nitrobenzaldehyde to prepare p-nitrobenzyl alcohol, one-step synthesis of cinnarizine by reduction catalysis of cinnamyl aldehyde and reduction of p-nitrobenzaldehyde to prepare p-aminobenzaldehyde.

Description

technical field [0001] The invention relates to a preparation method and an application of an adjustable metal-organic cage compound for selectively catalytically reducing nitrobenzaldehyde with high efficiency, and belongs to the technical field of fine chemicals. Background technique [0002] Fine chemicals such as drug molecules, food flavors and flavoring agents often have higher added value due to the complexity and difficulty of their synthesis. However, this type of compound has multiple functional groups, and it is necessary to catalyze the conversion of the functional group of the compound with high selectivity during the synthesis process. For example, p-nitrobenzyl alcohol is an important pharmaceutical synthesis intermediate, which can be used to synthesize imipenem, panipenem and other carbapenem antibiotics, which need to be selectively obtained by reducing the carbonyl group of nitrobenzaldehyde ; α, β-unsaturated alcohol is an important intermediate in the p...

Claims

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Application Information

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IPC IPC(8): C07F15/02C07F15/04C07F15/06C07F3/06C07D295/03C07D295/023C07C201/12C07C205/19C07C221/00C07C223/06B01J31/22
CPCB01J31/1815B01J2531/26B01J2531/842B01J2531/845B01J2531/847C07C201/12C07C221/00C07D295/023C07D295/03C07F3/003C07F15/025C07F15/045C07F15/065C07C205/19C07C223/06
Inventor 段春迎魏建伟赵亮何成
Owner DALIAN UNIV OF TECH
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