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Preparation method of 2,4-dioxy-3-azole-spiro[5,5]undecane 1,5-dinitrile

An aza, step two technology, applied in organic chemistry and other directions, can solve the problems of low product yield and purity, and achieve the effects of high product purity and yield, low unit consumption and mild reaction conditions

Active Publication Date: 2019-02-22
河北三川化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the problems of low product yield and purity in the existing preparation process of 2,4-dioxo-3-aza-spiro[5,5]undecane-1,5-dinitrile, the present invention provides a 2 , the preparation method of 4-dioxo-3-aza-spiro[5,5]undecane-1,5-dicarbonitrile

Method used

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  • Preparation method of 2,4-dioxy-3-azole-spiro[5,5]undecane 1,5-dinitrile

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Embodiment 1

[0036] A preparation method of 2,4-dioxo-3-aza-spiro[5,5]undecane-1,5-dinitrile:

[0037] 1000kg of cyclohexanone and 2100kg of methyl cyanoacetate were added to the reaction kettle, stirred and cooled to -10°C, and then 4900kg of ammonia methanol solution with an ammonia content of 8.6wt% was added dropwise at a constant speed. During the dropwise addition, the temperature of the reactor was controlled at -10°C, and the dropwise addition time was 15 hours. After the dropwise addition was completed, it was kept at 5°C for 13 hours.

[0038] After the heat preservation is completed, add 5200 kg of water, stir for 10 minutes, and then add sulfuric acid with a mass concentration of 53.64% dropwise to pH = 1.2. The dropwise addition time is 2 hours, and the temperature is controlled at 70°C during the dropwise addition. After the dropwise addition was completed, it was incubated at 50°C for 2.5h. Divide into 4 small batches of centrifugation, the centrifuge feed temperature is 40...

Embodiment 2

[0041] A preparation method of 2,4-dioxo-3-aza-spiro[5,5]undecane-1,5-dinitrile:

[0042] 1000kg of cyclohexanone and 2050kg of methyl cyanoacetate were added to the reaction kettle, stirred and cooled to -5°C, and then 3900kg of ammonia methanol solution with an ammonia content of 9.8wt% was added dropwise at a constant speed. During the dropwise addition process, the temperature of the reactor was controlled at 0°C, and the dropwise addition time was 7h. After the dropwise addition was completed, it was kept at 3°C ​​for 18h.

[0043] Add 2880 kg of water after the heat preservation is completed, stir for 10 minutes, and then add sulfuric acid with a mass concentration of 40.33% dropwise until pH = 2. The dropwise addition time is 2.5 hours, and the temperature is controlled at 30°C during the dropwise addition. After the dropwise addition was completed, it was kept at 70°C for 0.5h. Then the temperature was lowered to 50° C. and started to be centrifuged in 4 small batches...

Embodiment 3

[0046] A preparation method of 2,4-dioxo-3-aza-spiro[5,5]undecane-1,5-dinitrile:

[0047] 1000kg of cyclohexanone and 2120kg of methyl cyanoacetate were added to the reactor, stirred and cooled to 0°C, and then 9341kg of ammonia methanol solution with an ammonia content of 5.2wt% was added dropwise at a constant speed. During the dropwise addition process, the temperature of the reactor was controlled at 5°C, and the dropwise addition time was 12h. After the dropwise addition was completed, it was kept at -5°C for 25h.

[0048]Add 6232 kg of water after the heat preservation is completed, stir for 10 minutes, then add sulfuric acid with a mass concentration of 59.78% dropwise to pH = 3, add dropwise for 1 hour, and control the temperature at 50°C during the dropwise addition. After the dropwise addition was completed, it was incubated at 60°C for 1.5h. Then cool down to 50°C and begin centrifugation in 4 small batches, the centrifuge feed temperature is 50°C, and each small b...

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Abstract

The invention provides a preparation method of 2,4-dioxy-3-azole-spiro[5,5]undecane 1,5-dinitrile. The preparation method comprises the following steps that an ammonia methanol solution is dropwise added into a mixed solution of cyclohexanone and methyl cyanoacetate, and heat-insulating reaction is performed to obtain a 2,4-dioxy-3-azole-spiro[5,5]undecane 1,5-dinitrile ammonium salt solution; then, water is added for even mixing, a sulfuric acid solution is dropwise added, and heat-insulating reaction, separation and washing are performed to obtain the 2,4-dioxy-3-azole-spiro[5,5]undecane 1,5-dinitrile. The preparation method of the 2,4-dioxy-3-azole-spiro[5,5]undecane 1,5-dinitrile is simple in process and low in energy consumption, produces few side reaction, the product yield can reach98.5% or above, the ammonia nitrogen content in the product is 0.3% or below, the unit consumption of the methyl cyanoacetate is 0.85-1.1 t / t, and the preparation method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical production, in particular to a preparation method of 2,4-dioxo-3-aza-spiro[5,5]undecane-1,5-dinitrile. Background technique [0002] 2,4-Dioxo-3-aza-spiro[5,5]undecane-1,5-dicarbonitrile is an intermediate for the preparation of 1,1-cyclohexyldiacetic acid, and 1,1-cyclohexyldiacetic acid Acetic acid is an important pharmaceutical intermediate, such as an important intermediate of gabapentin. Gabapentin is an antiepileptic drug commonly used in the treatment of neuropathic pain and anxiolytic disorders. [0003] The current method for preparing 2,4-dioxo-3-aza-spiro[5,5]undecane-1,5-dinitrile is to add cyclohexanone and ethyl cyanoacetate to ammonia or ammonia in isopropyl However, this process is prone to side reactions, resulting in more impurities in the product, lower product purity, and it will also cause waste of raw materials, increase production costs, and also affect subsequent 1,1 Th...

Claims

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Application Information

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IPC IPC(8): C07D221/20
CPCC07D221/20
Inventor 时军兵梁兵陈雨佳孙东哲李婧林畅
Owner 河北三川化工有限公司
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