Method for synthesizing 1-amino naphthalenes

A technology of aminonaphthalene and nitronaphthalene, applied in the field of synthesis of 1-aminonaphthalene, can solve the problems of non-universality, serious environmental pollution, complicated operation, etc., and achieve low reaction process difficulty, high reaction selectivity, and simple raw materials Effect

Inactive Publication Date: 2005-03-30
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

Although the iron filings method and the soda sulfide method have wide adaptability, simple process, and reasonable technical economy, they are seriously polluted to the environment and have been gradually eliminated; the electrolysis method has high yield, easy operation, and environmental friendliness, but it consumes a lot of energy and is now widely used. In laboratory synthesis and semi-industrial production; catalytic hydrogenation method has large output and high product quality, and has obvious advantages in solving environmental pollution problems. Therefore, this method has become the mainstream in industry, but this method requires the use of more expensive catalysts and hydrogen, the cost is high and the operation is more complicated
In addition, there are reduction methods using hydrazine under the action of catalysts and metal hydride reduction methods, but they are only suitable for the reduction of special aromatic nitro compounds, and the cost is high, so they are not universal

Method used

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  • Method for synthesizing 1-amino naphthalenes
  • Method for synthesizing 1-amino naphthalenes

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Add 1-nitronaphthalene (10mmol), Se (0.4mmol), H 2 O (0.1mol), triethylamine (5mmol) and solvent DMF (40ml), continue to pass carbon monoxide, then heat to 88 ° C and stir for 4 hours, cool to room temperature, switch carbon monoxide to oxygen or air and stir for 0.5-1 hour Finally, the selenium powder is filtered out, and after the filtrate obtained by filtering is concentrated, the content is determined by gas chromatography, and the chromatographic yield of 1-aminonaphthalene is 100% (in terms of 1-nitronaphthalene). The content determination adopts HP-4890D gas chromatography system, including FID detector, SE-54 capillary column (30m×0.32mm×1.5μm), vaporization chamber temperature: 280°C, column temperature: 250°C, external standard method for quantification.

Embodiment 2

[0019] The solvent is formylpiperidine, and the reaction time is 10 hours. Other experimental methods and conditions are the same as in Example 1. The yield of 1-aminonaphthalene measured by gas chromatography is 50% (calculated as 1-nitronaphthalene).

Embodiment 3

[0020] Embodiment 3: solvent is DMSO, and the reaction time is 3 hours, and other experimental methods and conditions are the same as embodiment 1, and the yield of 1-aminonaphthalene measured by gas chromatography is 100% (calculated as 1-nitronaphthalene).

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Abstract

A process for synthesizing amino naphthalene by nitro naphthalene with carbon monoxide and water, selenium as catalyst, organic alkali and inorganic alkali as assistant catalyst in organic solvent, the molar ratio of nitro naphthalene and water is 1:1 to 1:1000, the molar amount of selenium is 0.1-100% of the molar amount of nitro naphthalene; the molar amount of organic alkali and inorganic alkali is 1-36 hours; reaction temperature is 20-120 deg.C.

Description

technical field [0001] The invention relates to the synthesis of 1-aminonaphthalene, in particular to a method for synthesizing 1-aminonaphthalene by utilizing carbon monoxide and water through selenium catalytic reduction. Background technique [0002] As an important organic synthesis intermediate and raw material, 1-aminonaphthalene is widely used in the fields of medicine, pesticide, dyestuff, auxiliary agent and so on. At present, 1-aminonaphthalene is obtained through the reduction of 1-nitronaphthalene, and the number of relevant documents is huge. The reduction methods of nitro compounds used in industrialization mainly include the following: iron filings reduction, alkali sulfide reduction, electrolysis Reduction and catalytic hydrogenation reduction. Although the iron filings method and the soda sulfide method have wide adaptability, simple process, and reasonable technical economy, they are seriously polluted to the environment and have been gradually eliminated;...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/32C07C211/58
Inventor 刘晓智陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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