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Preparation method of 4-pyridylaldehyde

A pyridine carboxaldehyde, cyanopyridine technology, applied in the direction of organic chemistry and the like, can solve the problems of unsuitability for industrial production, a large amount of manganese dioxide waste residue, large environmental pollution, etc., and achieves low cost, short reaction period and good catalytic selectivity. Effect

Inactive Publication Date: 2012-08-01
CANGZHOU SENARY CHEM SCI TEC
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0006] Journal of Xianning University 2004: 18-19 Huang Shengtang and Zhou Heping reported that 4-pyridinecarboxylate was obtained by esterification, hydrazinolysis and oxidation of 4-pyridinecarboxylic acid as a raw material, but the reaction time of this method is long and the yield is not high, so it is not suitable for industrial production
[0007] The Journal of Shandong Jianzhu University, Vol. 21, No. 6, 2006, Qin Weiwei, Cai Xiukai, etc. recorded that 4-pyridinemethanol was oxidized with manganese dioxide to obtain 4-pyridineformaldehyde. This method will produce a large amount of manganese dioxide waste residue and cause great environmental pollution.

Method used

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  • Preparation method of 4-pyridylaldehyde

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Experimental program
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Effect test

Embodiment 1

[0027] 1. Preparation of Cu-Ni catalyst

[0028] Add 900L of purified water to a 1000L reactor, stir, add 9kg of copper sulfate pentahydrate, then add 30kg of Raney-Ni catalyst (water content 50%), stir for 30 minutes, let stand, take out the supernatant; add 600L of purified water and stir for 30 Minutes, let it stand, and take out the supernatant; repeat the washing 4 to 6 times until the washing water is checked with a barium chloride test solution without precipitation; put the washed catalyst in a bucket, add purified water and soak it for 25 days to obtain Cu- Ni catalyst.

[0029] 2, the preparation method of 4-pyridinecarbaldehyde, comprises the following steps:

[0030] (1) Add 300kg of purified water to a 1000L dissolution reactor, stir, and slowly add 130kg of concentrated sulfuric acid (with a mass fraction above 97%) under brine cooling, add 50.0kg of 4-cyanopyridine below 30°C, and continue stirring for 30 ~60 minutes for complete dissolution of 4-cyanopyridine...

Embodiment 2

[0040] Other parameters of the preparation method of the catalyst are the same as in Example 1, and the soaking time is 35 days.

[0041] The preparation method of 4-pyridinecarbaldehyde comprises the following steps:

[0042] (1) Add 300kg of purified water to a 1000L dissolution reactor, stir, and slowly add 130kg of concentrated sulfuric acid (with a mass fraction above 97%) under brine cooling, add 50.0kg of 4-cyanopyridine below 30°C, and continue stirring for 30 ~60 minutes for complete dissolution of 4-cyanopyridine.

[0043] The above-mentioned 4-cyanopyridine sulfuric acid solution was transferred to a 1000L hydrogenation reactor, stirred, and 15kg (water content 50%) Cu-Ni catalyst plus 80kg purified water was transferred to the hydrogenation reactor. With 0.7MPa N 2 Leak test, then use 0.5MPa H 2 replace N 2 three times. Charge H 2 to 0.5MPa, raise the temperature to 70°C, hydrogenate at 0.6MPa until the reaction system absorbs hydrogen at 0.01-0.03MPa for 20 ...

Embodiment 3

[0050] The preparation method of catalyst is the same as embodiment 1.

[0051] The preparation method of 4-pyridinecarbaldehyde comprises the following steps:

[0052] (1) Add 300kg of purified water to a 1000L dissolution reactor, stir, and under brine cooling, slowly add 235kg of concentrated sulfuric acid (more than 97% mass fraction), add 50.0kg of 4-cyanopyridine below 30°C, and continue stirring for 30 ~60 minutes for complete dissolution of 4-cyanopyridine.

[0053] The above-mentioned 4-cyanopyridine sulfuric acid solution was transferred to a 1000L hydrogenation reactor, stirred, and 15kg (water content 50%) Cu-Ni catalyst plus 80kg purified water was transferred to the hydrogenation reactor. With 0.7MPa N 2 Leak test, then use 0.5MPa H 2 replace N 2 three times. Charge H 2 to 0.5MPa, raise the temperature to 80°C, hydrogenate at 0.8MPa until the reaction system absorbs hydrogen at 0.01-0.03MPa for 20 minutes, then cool down to normal temperature. Row H 2 , w...

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Abstract

The invention discloses a preparation method of 4-pyridylaldehyde, which belongs to the field of heterocyclic compounds, and comprises the following steps of: (1) adding 4-cyanopyridine into protonic acid water solution, adding a Cu-Ni catalyst, mixing uniformly, and adding hydrogen to carry out hydrogenation reaction until finishing the reaction; (2) filtering; (3) adding a neutralizing agent into the obtained 4-pyridylaldehyde acid solution filtered through the step (2), and neutralizing until a pH value reaches 4-6; and (4) separating and purifying the 4-pyridylaldehyde. According to the method, the Cu-Ni catalyst is adopted to carry out catalytic hydrogenation, so that the generation of 4-pyridinemethylamine, 4-pyridinemethanol and other impurities is avoided, the reaction period is short, and the yield and the purity are high.

Description

technical field [0001] The invention relates to a preparation method of 4-pyridinecarbaldehyde, which belongs to the field of heterocyclic compounds. Background technique [0002] 4-Pyridinecarbaldehyde is an intermediate and basic organic synthetic raw material for the synthesis of donepezil hydrochloride for the treatment of moderate to mild senile dementia. [0003] There are various reports about the preparation method of 4-pyridylcarbinaldehyde: Fieser M Fieser and fiesers reagents for organic synthesis [M].John.Wiley and Sons.Tnc.1984,448 and BockelheideV, Linn WJ.A novel synthesis of pyridyl carbinels and aldehydes [J]Am chem. Soc. 1954,76:1286-1291 reported the preparation of 4-pyridinecarbaldehyde by high-temperature catalytic oxidation using 4-picoline as a raw material. This method requires a high temperature of 400°C and a V-Mo catalyst. The product is a mixture of 4-pyridinecarboxylic acid, 4-pyridinecarbaldehyde, 4-pyridinemethanol and 4-picoline, and it is di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/48
Inventor 李志陵张月成于树岭李志刚刘劲松孙海丽王建柏
Owner CANGZHOU SENARY CHEM SCI TEC
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