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Method and device for continuously preparing 5-nitro-1,4-dihydro-1,4-methano-naphthalene through channelization

A bridge methylene, pipeline technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve the problems of high risk, unsuitable for industrial production, etc., achieve convenient operation, overcome local concentration inconsistencies Uniform, easy post-processing results

Active Publication Date: 2018-05-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

During this operation, the diazonium salt, which is prone to explosion, is directly filtered out and dropped into the reactor, which is dangerous and not suitable for industrial production.

Method used

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  • Method and device for continuously preparing 5-nitro-1,4-dihydro-1,4-methano-naphthalene through channelization
  • Method and device for continuously preparing 5-nitro-1,4-dihydro-1,4-methano-naphthalene through channelization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The structure of the reaction device is as figure 1 , Tubular reactor I 9 in this example: single tube, tube length 5 m, tube diameter 1 mm; tube reactor II 10: single tube, tube length 10 m, tube diameter 1 mm.

[0027] The molar flow ratio of cyclopentadiene, isoamyl nitrite and 2-amino-6-nitrobenzoic acid is 2: 1:1;

[0028] Pre-prepared 2-amino-6-nitrobenzoic acid solution: 2-amino-6-nitrobenzoic acid (1.82Kg, 10mol), diethylene glycol dimethyl ether 9.5Kg.

[0029] Pre-prepared nitrite solution: isoamyl nitrite (1.17Kg, 10mol), trichloroacetic acid (1.62Kg, 10mol).

[0030] Prepare cyclopentadiene: cyclopentadiene (1.32Kg, 20mol).

[0031]Cool the tubular reactor I 9 to 10°C and keep it warm, store the 2-amino-6-nitrobenzoic acid solution and the nitrite solution in the storage tank I 1 and the storage tank II 2 respectively, and store the cyclopentadiene In the reservoir III 3, the 2-amino-6-nitrobenzoic acid solution and the nitrite solution are continuously i...

Embodiment 2

[0033] The structure of the reaction device is as figure 1 , Tubular reactor I 9: single tube, tube length 5 m, tube diameter 3 mm, tube reactor II 10: single tube, tube length 20 m, tube diameter 3 mm.

[0034] The molar flow ratio of cyclopentadiene to 2-amino-6-nitrobenzoic acid is 5:1, the reaction temperature in tubular reactor I9 is ​​5°C, and the retention time is 60s. The dwell time in 10 is 10s,

[0035] Other operations were the same as in Example 1, and 1.06 Kg of 5-nitro-1,4-dihydro-1,4-endomethylene-naphthalene was finally obtained, with a yield of 57% and a GC content of 92.4%. Gas phase detection conditions are the same as in Example 1.

Embodiment 3

[0037] The structure of the reaction device is as figure 1 , Tubular reactor I 9: single tube, tube length 5 m, tube diameter 3 mm, tube reactor II 10: single tube, tube length 1 m, tube diameter 6 mm.

[0038] The molar flow ratio of cyclopentadiene to 2-amino-6-nitrobenzoic acid is 5:1, the reaction temperature in tubular reactor I9 is ​​-10°C, and the retention time is 60s. In tubular reactor II10 The reaction temperature is 120°C and the residence time is 180s.

[0039] Other operations were the same as in Example 1, and 0.89 Kg of 5-nitro-1,4-dihydro-1,4-endomethylene-naphthalene was finally obtained, with a yield of 48% and a GC content of 95.3%. Gas phase detection conditions are the same as in Example 1.

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Abstract

The invention discloses a method and device for continuously preparing 5-nitro-1,4-dihydro-1,4-methano-naphthalene through channelization. The method comprises the following steps: continuously conveying a 2-amino-6-nitrobenzoic acid solution stored in a storage device I and a nitrite solution stored in a storage device II into a mixer I through a metering pump I and a metering pump II for mixing,enabling the mixed liquid to enter a tubular reactor I for a diazotization reaction, then simultaneously conveying cyclopentadiene stored in a storage device III and a diazotization reaction liquid in the tubular reactor I into a mixer II through a metering pump III for mixing, enabling the mixed liquid to enter a tubular reactor II for a reaction, after the reaction is finished, enabling the reaction liquid to enter a receiving tank, and performing post-treatment to obtain the 5-nitro-1,4-dihydro-1,4-methano-naphthalene. The device used in the invention has a simple structure, the preparation method has good process safety, the reaction conditions are easy to control, the continuous production can be realized, the product has a high yield and stable quality, and large-scale production can be realized in industry with only a small amount of investment.

Description

technical field [0001] The invention relates to a compound preparation method and a device thereof, in particular to a method and a device for pipelined continuous preparation of 5-nitro-1,4-dihydro-1,4-endomethylene-naphthalene. Background technique [0002] 5-nitro-1,4-dihydro-1,4-endomethylene-naphthalene is a key intermediate for the preparation of broad-spectrum fungicide benzovinfluconazole, and the relatively simple synthesis method of this intermediate is based on 2 -Amino-6-nitrobenzoic acid is used as the starting material, which is obtained through diazotization reaction to generate diazonium salt, and then heated to produce o-nitrophenylyne and cyclopentadiene to undergo [4+2] addition reaction. The diazotization reaction is operated in batch kettle mode. This method has many defects. For example, the traditional diazotization is a batch production mode, and the diazonium salt stays in the reactor for a long time, which increases the probability of side reactions...

Claims

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Application Information

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IPC IPC(8): C07C205/06C07C201/12B01J19/24
CPCB01J19/2425C07C201/12C07C205/06
Inventor 李振华谭志勇金国强
Owner ZHEJIANG UNIV OF TECH
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