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A kind of synthetic method of 1-cyclohexene-1,2-dicarboximide

A dicarboximide and synthesis method technology, applied in the direction of organic chemistry, can solve problems such as difficult separation, low product quality, difficult to apply to the fields of biology and materials science, and achieve high selectivity, high conversion rate, The effect of avoiding polymerization side reactions

Active Publication Date: 2022-04-12
仪征市海帆化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Because both isomerization and amidation are carried out at high temperature, both the intermediate product and the final product will inevitably generate a large amount of gelatinous substances produced by double bond cleavage and repolymerization, which are difficult to separate, and the product quality is low, and it is difficult to apply fields of biology and materials science

Method used

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  • A kind of synthetic method of 1-cyclohexene-1,2-dicarboximide
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  • A kind of synthetic method of 1-cyclohexene-1,2-dicarboximide

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0036] Add 14.7g (0.1mol) of phthalimide, 500ml of N,N-dimethylformamide and 1g of 60% palladium carbon (5%) on a dry basis in a 1L stainless steel magnetically stirred autoclave, and close the reaction kettle . After the air in the kettle was replaced with nitrogen, stirring was started to raise the temperature.

[0037] When the temperature rises to 90°C, the gauge pressure is 0MPa. At this time, hydrogen gas was introduced, and the temperature in the kettle was ensured to be between 85-95°C. After 15 minutes, the pointer of the pressure gauge was raised, the hydrogen inlet valve was closed, and the heat preservation and stirring were continued for 2.5 hours, and the pressure gauge returned to zero.

[0038] Open the hydrogen inlet valve again, and after 40 minutes, the pointer of the pressure gauge rises, close the hydrogen inlet valve, continue to keep warm and stir for 2 hours, and the pressure gauge returns to zero.

[0039] In this way, whenever the pressure gauge ha...

example 2

[0043] Add 55g (0.37mol) of phthalimide, 700ml of N,N-dimethylformamide and 5.5g of 60% palladium carbon (5%) on a dry basis in a 1L stainless steel magnetically stirred autoclave, and close the reaction kettle . After the air in the kettle was replaced with nitrogen, stirring was started to raise the temperature.

[0044] When the temperature rises to 80°C, the gauge pressure is 0MPa. At this time, hydrogen gas was introduced, and the temperature in the kettle was ensured to be between 75-90°C. After 35 minutes, the pointer of the pressure gauge was raised, the hydrogen inlet valve was closed, and the heat preservation and stirring were continued for 3 hours, and the pressure gauge returned to zero.

[0045] Open the hydrogen inlet valve again, and after 40 minutes, the pointer of the pressure gauge rises, close the hydrogen inlet valve, continue to keep warm and stir for 2 hours, and the pressure gauge returns to zero.

[0046]In this way, whenever the pressure gauge has ...

example 3、4、5

[0050] Except catalyzer, repeat example 2 operation, obtain the result shown in the following table. The catalyst filtered out in Example 2 was only dried (vacuum oven, 100° C., 5 hours), and no new catalyst was added, and it was directly used in Examples 3, 4, and 5.

[0051]

[0052] As can be seen from the above table, the catalyst can be recycled and used mechanically. But when it is applied to the third time, the content of the product drops significantly, the melting range of the product is long, and there are many impurities.

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Abstract

The invention discloses a synthesis method of 1-cyclohexene-1,2-dicarboximide. Using phthalimide and hydrogen as raw materials, 1-cyclohexene-1,2-dicarboximide is prepared in a high yield under the catalysis of a catalyst. The present invention achieves the purpose of avoiding side reactions by changing the process conditions, and finally realizes high selectivity and high conversion rate of the reaction; the reaction solution can obtain products with a mass fraction of more than 98% by means of simple distillation and crystallization filtration; By adding palladium-carbon with a mass fraction of 5% and a mass fraction of 60% on a dry basis as a catalyst, palladium-carbon was used as a catalyst to catalyze the reaction, and the low-temperature reaction was realized, and the highest reaction conversion rate could reach more than 93%.

Description

technical field [0001] The invention belongs to the improvement of the synthesis method of 1-cyclohexene-1,2-dicarboximide. Background technique [0002] 1-cyclohexene-1,2-dicarboximide, the molecular structure is: [0003] [0004] 1-Cyclohexene-1,2-dicarboximide, also known as 3,4,5,6-tetrahydrophthalimide, or tetrahydrophthalimide, the pure product is white flakes crystalline powder. As an intermediate, it is widely used in various fields of organic synthesis, such as biomedicine, new unsaturated resin materials, modification of composite materials, pesticides, etc. It has broad application prospects. [0005] At present, it is reported in open literature that its synthetic method is mostly to use maleic anhydride and 1,4-butadiene to carry out conjugate addition first to obtain 1,2,3,6-tetrahydrophthalic anhydride, and then in pentoxide Under the catalysis of diphosphorus, 3,4,5,6-tetrahydrophthalic anhydride is obtained through isomerization reaction by heating a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 邹从伟戴久坤周芬沈永刚邹从欢
Owner 仪征市海帆化工有限公司