Preparation of 1,8-diazabicyclo[5.4.0]undec-7-ene

A technology of dinitrobicyclo and acrylonitrile, which is applied in the field of chemical synthesis of pharmaceutical intermediates, can solve the problems of high raw material cost and increased solvent loss, and achieve the effects of increased raw material conversion rate, reduced catalyst cost, and simplified post-treatment

Inactive Publication Date: 2008-10-08
山东新华万博化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] (1) the yield of the addition reaction is only 90%, and the caprolactam transformation rate that accounts for the largest raw material cost is only 96%, thereby causing the ...

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0020] Technology of the present invention:

[0021] In a 500ml reaction flask, add 100g caprolactam, 70ml tert-butanol, 0.3g NaOH, start to add 50.2g of acrylonitrile dropwise when the temperature rises to 40°C, drop the temperature at 40-45°C, and keep it warm for 1 hour after the dropwise addition to stop the reaction , lower the temperature and add sulfuric acid to adjust the pH to 6~7, transfer to the autoclave, add 10g Raney Ni as a catalyst, pass through 30g NH3 to raise the temperature and react after replacement, control the temperature at 115±5°C, start to flow hydrogen, and control the pressure at 5.0MPa until the pressure does not drop until. After the reaction is completed, recover the solvent, then add 3g of p-toluenesulfonic acid and 50ml of toluene, heat up at 150-180°C for closed-loop dehydration until no water comes out, recover the solvent, and fractionally distill to obtain DBU finished product with a total yield of 80%. Caprolactam conversion The rate is ...

Embodiment 2

[0025] Technology of the present invention:

[0026] In a 500ml reaction bottle, add 100g caprolactam, 80ml tert-amyl alcohol, 0.5g NaOH, start to add 50.2g of acrylonitrile dropwise when the temperature rises to 40°C, drop the temperature at 10-15°C, keep it warm for 1 hour after dropping to stop the reaction , add sulfuric acid to adjust the pH to 6~7, transfer to an autoclave, add 10g Raney Ni as a catalyst, pass through 30g NH3 to raise the temperature and react after replacement, control the temperature at 115±5°C, start to pass hydrogen, and control the pressure at 5.0MPa until the pressure does not drop . After the reaction is completed, recover the solvent, then add 3g of p-toluenesulfonic acid and 50ml of toluene, heat up at 150-180°C for closed-loop dehydration until no water comes out, recover the solvent, and fractionally distill to obtain DBU finished product with a total yield of 81.2%. Caprolactam conversion The rate is 98.1%.

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PUM

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Abstract

The invention provides a method to prepare 1,8-dinitrogen-hexagon[5,4,0]hendecene(DBU) with caprolactam and acrylonitrile as material through addition reaction, hydrogenation reaction and cyclization reaction. The method is characterized in that tert-butyl alcohol or tertiary amyl alcohol is used as solvent and NaOH is used as catalyzer during the addition reaction which begins at the temperature of 10-15 DEG C; the hydrogenation reaction is carried out directly after the addition reaction, without recycling the solvent. The method has the advantages that (1) conversion rate of the materials is high, increased from the original 96% to 98%, and the yield of DBU is increased from 74% to above 80%, thus greatly reducing cost on the materials; (2) the process after the addition reaction is simplified and since the conversion rate of caprolactam is improved, the solvent and the caprolactam are of no need to recycle;(3) cost and consumption of catalyzer are reduced; (4)the same solvent is used in the addition reaction and the hydrogenation reaction, thus reducing the loss of solvent.

Description

technical field [0001] The invention relates to a chemical synthesis process of a pharmaceutical intermediate, in particular to a method for preparing a catalyst 1,8-diazabicyclo[5,4,0]undecene (hereinafter referred to as DBU). Background technique [0002] DBU is used as a catalyst for the production of polyurethane and other chemicals, such as ammonia and ethylene dichloride react to form piperazine in its presence; it is also an excellent decarboxylation agent, hardener for epoxy resin, anti-corrosion agent Rust agent, it can also be formulated as advanced corrosion inhibitor, widely used in the production of semi-synthetic antibiotic drugs. [0003] CN1262274 discloses an existing synthesis process of DBU, using caprolactam and acrylonitrile as raw materials, through three steps of addition reaction, hydrogenation reaction and cyclization reaction: [0004] The first step of addition reaction: using aromatic hydrocarbon as solvent, using a mixture of organic base and in...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 毕作文高鸿斌曹洪博王效梅刘昌娥徐芹张宗华
Owner 山东新华万博化工有限公司
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