Preparation method and applications of metal organic triangular prism compound for preparing amine aromatic hydrocarbons through catalytic reduction of nitro aromatic hydrocarbons

A technology for preparing amine-based aromatic hydrocarbons and metal organics from nitroaromatic hydrocarbons is applied in the preparation of organic compounds, cobalt organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., and can solve the problem of high production cost and high atomic hydrogen activity. , low production safety and other problems, to achieve the effect of high yield, stable chemical properties and low price

Active Publication Date: 2019-11-19
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it needs to use flammable catalyst Raney nickel or precious metal catalyst platinum, palladium, rhodium, etc. in the actual production process, so the production safety is not high, and the production cost is high, and the selectivity needs to be improved.
(3) Electrolytic reduction method, aromatic nitro compounds are usually in the cathode (metal Materials such as copper, nickel, palladium, etc.) are electrolyzed to generate active atomic hydrogen, which then reduces arylamine compounds to nitro compounds, but atomic hydrogen is extremely active, and this method still receives other functional groups that are easily hydrogenated. influences

Method used

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  • Preparation method and applications of metal organic triangular prism compound for preparing amine aromatic hydrocarbons through catalytic reduction of nitro aromatic hydrocarbons
  • Preparation method and applications of metal organic triangular prism compound for preparing amine aromatic hydrocarbons through catalytic reduction of nitro aromatic hydrocarbons
  • Preparation method and applications of metal organic triangular prism compound for preparing amine aromatic hydrocarbons through catalytic reduction of nitro aromatic hydrocarbons

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Isophthalic acid (33.0 g, 0.20 mol) and 95% paraformaldehyde (3.1 g, 0.10 mol) were dissolved in 100 mL of 20% oleum, and the mixture was stirred at 118° C. for 6 hours. After cooling to room temperature, the mixture was poured onto ice water, and the precipitate was filtered, washed with water, and dried in vacuo to obtain a yellow solid. Then the obtained yellow solid was dissolved in 100 mL of methanol, 220 mL of hydrochloric acid was added and refluxed for 30 minutes. The mixture was cooled to 10°C, then the solid product which appeared was filtered, washed with cold methanol and dried. 4.40 g of white solid product was obtained with a yield of 11%. 1 H-NMR (400MHz, CDCl3): δ8.55(t, J=1.6Hz, 2H), 8.05(d, J=1.6Hz, 4H), 4.16(s, 2H), 3.93(s, 12H).ESI -MS mass spectrum, exact molecular weight 400.1158, actual peak 401.1237[M+H] + ,423.1068[M+Na] + .

[0024] After mixing the white solid product (4.00 g, 10 mmol) with 800 mmol of hydrazine hydrate, it was stirred un...

Embodiment 2

[0028] Co(ClO 4 ) 2 ·6H 2 O (36.6mg, 0.1mmol) and the ligand H prepared in Example 1 4 PTPC (74.5mg, 0.05mmol) was dissolved in 30mL of methanol, ethanol and acetonitrile in a mixed solvent with a ratio of 1:0.9:2, stirred at room temperature for 4 hours, stirred and filtered, and the filtrate was placed in the solution at room temperature for 2 weeks An orange-red solid was precipitated to obtain 27.3 mg of the target compound Co-PTPC with a yield of 21.9%. ESI-MS mass spectrum: m / z: 801.66[Co 6 (PTPC) 3 ] 6+ .

Embodiment 3

[0030] Co(BF 4 ) 2 ·6H 2 O (34.1mg, 0.1mmol) and the ligand H prepared in Example 1 4 PTPC (74.5mg, 0.05mmol) was dissolved in 30mL of methanol, ethanol and acetonitrile in a mixed solvent with a ratio of 1:1:1.5, stirred at room temperature for 4 hours, stirred and filtered, and the filtrate was placed in the solution at room temperature for 2 weeks An orange-red solid was precipitated to obtain 22.4 mg of the target compound Co-PTPC with a yield of 18.2%. ESI-MS mass spectrum: m / z: 801.66[Co 6 (PTPC) 3 ] 6+ .

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Abstract

The invention belongs to the technical field of fine chemical industry, and relates to a preparation method and applications of a metal organic triangular prism compound for preparing amine aromatic hydrocarbons through catalytic reduction of nitro aromatic hydrocarbons. According to the preparation method, the metal organic triangular prism compound is prepared by using the Co<2+> in a transitionmetal salt as a node and using L as a ligand through a reaction; the synthesis route is Co<2+>+L [arrow] Co-L; and the ligand L is selected from H4PTPC, and the transition metal salt is one selectedfrom cobalt nitrate, cobalt perchlorate, cobalt tetrafluoroborate and cobalt trifluoromethanesulfonate. According to the present invention, the preparation method has characteristics of inexpensive raw materials and high yield, and the prepared metal organic triangular prism compound has stable chemical properties, and is easily used in practical application; and with the application of the prepared metal organic triangular prism compound as the compound Co-PTPC in the reduction of m-nitroacetophenone into m-aminoacetophenone and the reduction of p-nitroacetophenone into p-aminoacetophenone, the TON can be up to 36000, and the selectivity is greater than 99%.

Description

technical field [0001] The invention relates to a preparation method and application of a metal-organic triangular prism compound used for catalytic reduction of nitroaromatics to produce aminoaromatics, and belongs to the technical field of fine chemicals. Background technique [0002] Aminoaromatic compounds are one of the most important intermediates in the production of chemical industry. They can be used in the dye industry to produce acid ink blue G, golden light red, phenol cyanine red, etc.; Agents such as DDV, webfen, toxachlor, etc. Among them, p-aminoacetophenone is a very important pharmaceutical intermediate used for the synthesis of crotonin and flurbiprofen. Clantamin can be used to treat diseases such as bronchial asthma, chronic asthmatic bronchitis and emphysema. Flurbiprofen is a non-steroidal anti-inflammatory analgesic that can be used for rheumatoid arthritis, osteoarthritis, and flexural spondylitis. At present, there are three main methods in the i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/50C07F15/06B01J31/24C07C221/00
CPCB01J31/2409B01J2231/64B01J2531/845C07C221/00C07F9/5022C07F9/5054C07F15/065C07C225/22
Inventor 段春迎赵亮魏建伟刘广洲
Owner DALIAN UNIV OF TECH
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