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Method for preparing 1,6-adipaldehyde

A technology of adipaldehyde and cyclohexene, which is applied in the field of fine chemical synthesis, can solve the problems of harsh low-temperature reaction conditions, expensive catalysts, and long reaction time, and achieve the effects of simple process, good industrial application prospects, and high activity

Inactive Publication Date: 2012-10-24
中国平煤神马控股集团有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Catalytic hydrogenation reduction to decompose ozonide has better reduction efficiency, but the catalyst is more expensive and the operation is inconvenient
The above-mentioned zinc powder-acetic acid produces nascent hydrogen reduction decomposition method, the low temperature reaction conditions are harsh, and the reaction time is long

Method used

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  • Method for preparing 1,6-adipaldehyde

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Experimental program
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Effect test

Embodiment 1

[0023] (1) Add 50mmol of cyclohexene, 15mL of dichloromethane and 6g (100mmol) of glacial acetic acid in a three-necked flask, put it in a low-temperature reaction bath, stir until the temperature of the system drops to -20℃, and pass O 3 / O 2 Carry out ozonation reaction. The tail gas first absorbs unreacted ozone through potassium iodide solution, and then recovers a small amount of volatile cyclohexene and organic solvent through glacial acetic acid. With 5% Br 2 / CCl 4 The solution detects the end of the reaction, after the oxidation is completed, pass 2 min N 2 Excess ozone is eliminated to obtain the ozonation reaction liquid, and the ozone compound directly enters the reduction reaction without separation.

[0024] (2) Transfer the ozonation reaction solution to a constant pressure dropping funnel, add it dropwise to 50mmol of activated zinc powder in distilled water, and complete the dropwise addition within 0.5h; stir for 50min at room temperature under nitrogen protectio...

Embodiment 2

[0026] (1) Add 50 mmol of cyclohexene, 25 mL of chloroform and 5.4 g (90 mmol) of glacial acetic acid in a three-necked flask, put it in a low-temperature reaction bath, stir until the temperature of the system drops to -10°C, and pass O 3 / O 2 Carry out oxidation reaction. The tail gas first absorbs unreacted ozone through potassium iodide solution, and then recovers a small amount of volatile cyclohexene and organic solvent through glacial acetic acid. With 5% Br 2 / CCl 4 The solution detects the end of the reaction, after the oxidation is completed, pass 2 min N 2 Excess ozone is eliminated to obtain the ozonation reaction liquid, and the ozone compound directly enters the reduction reaction without separation.

[0027] (2) Transfer the ozonation reaction solution to a constant pressure dropping funnel, add dropwise to 45mmol of distilled water containing activated zinc powder, and complete the dropwise addition within 0.5h; stir and react at room temperature under nitrogen pro...

Embodiment 3

[0029] (1) Add 50 mmol of cyclohexene, 40 mL of 1,2-dichloroethane and 6.6 g (110 mmol) of glacial acetic acid in a three-necked flask, put it in a low-temperature reaction bath, and stir until the temperature of the system drops to 5°C. O 3 / O 2 Carry out oxidation reaction. The tail gas first absorbs unreacted ozone through potassium iodide solution, and then recovers a small amount of volatile cyclohexene and organic solvent through glacial acetic acid. With 5% Br 2 / CCl 4 The solution detects the end of the reaction, after the oxidation is completed, pass 2 min N 2 Excess ozone is eliminated to obtain the ozonation reaction liquid, and the ozone compound directly enters the reduction reaction without separation.

[0030] (2) Transfer the ozonation reaction solution to a constant pressure dropping funnel, add it dropwise to 60mmol of distilled water containing activated zinc powder, and complete the dropwise addition within 0.5h; stir and react at room temperature for 75min un...

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Abstract

The invention belongs to the field of synthesis of fine chemicals, and discloses a method for preparing 1,6-adipaldehyde. The method comprises the following steps of: performing an ozonization reaction on cyclohexene serving as a raw material by taking ozone as an oxidant and taking an organic solvent and glacial acetic acid as mixed solvents at the reaction temperature of between 20 DEG C below zero and 10 DEG C to obtain an ozonized reaction liquid, and directly performing a reducing reaction on an ozonide without separating; and reducing and decomposing by adopting zinc powder, and reacting under the protection of nitrogen gas at the room temperature for 0.5-1.5 hours to obtain 1,6-adipaldehyde. Compared with the conventional method, the method has the advantages: ozone is taken as an oxidant, so that high oxidizing capacity and high selectivity are realized, the environmental pollution is low, the requirement of ozonization reaction temperature is low, energy is saved, and consumption is lowered. After reacting, a product is easy and convenient to separate; and zinc acetate is recovered from a water phase by concentrating and crystalizing, so that production cost is lowered, and industrial production is facilitated.

Description

Technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and relates to a method for synthesizing aldehyde compounds, in particular to a method for preparing 1,6-adipaldehyde by an ozone oxidation method. Background technique [0002] 1,6-Hexanedial (1,6-Hexanedial) is a new non-toxic, quick-acting and broad-spectrum chemical sterilant, which can kill most bacteria, bacterial propagules, fungi, spores and viruses quickly and efficiently , And it is green without residue and harmless to human body; it does not corrode metal equipment, glass and plastic products, and is widely used in the disinfection and sterilization of medical equipment, food equipment, poultry and livestock houses, etc. In addition, 1,6-adipaldehyde is also used in petroleum exploration to inhibit the effect of sulfate-reducing bacteria and prevent the increase in sulfur content of crude oil. 1,6-Adipaldehyde, as a kind of crosslinking agent, has the characteristics of hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/12C07C45/40C07C53/10C07C51/41
Inventor 刘慧郑晓广章亚东李吉芳梁政勇李世强张明林健
Owner 中国平煤神马控股集团有限公司
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