Method for preparing 1,5-diamino-decahydronaphthalene by catalytic hydrogenation of 1,5-diaminonaphthalene

A technology of diaminodecalin and diaminonaphthalene, which is applied in the field of preparing 1,5-diaminodecalin by catalytic hydrogenation of 1,5-diaminonaphthalene, can solve the problem of low nickel effective utilization rate, narrow activation temperature, Dispersion is not high, to achieve good activity and product selectivity, high recycling rate, simple preparation process

Inactive Publication Date: 2013-09-25
武汉椿岭科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the active temperature of nickel-aluminum catalysts currently used in industry is narrow (generally 130-180°C), and even under the best conditions, the yield of the target product cyclohexylamine is only 30-50%, and Accompanied by a large number of side reaction products, such as dicyclohexylamine, N-cyclohexylaniline, benzene and ammonia, in addition to unconverted aniline, these disadvantages are generally considered to be largely due to the higher nickel content, which in the support Accumulated on the surface, the degree of dispersion is not high, resulting in low effective utilization of nickel

Method used

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Comparison scheme
Effect test

preparation example Construction

[0018] The preparation method of the supported nickel-based hydrogenation catalyst is as follows: the active component nickel is loaded on the oxide or zeolite molecular sieve carrier by impregnation method. The impregnation method generally first impregnates the nickel salt solution on the oxide or molecular sieve carrier, and after drying Calcined at 400 °C for 3-5 h, and then reduced at 400 °C for 2-4 h under a hydrogen atmosphere to obtain a supported nickel-based hydrogenation catalyst.

[0019] For example, weigh 1.37g to 4.11g of cobalt nitrate (the value here is based on the metal nickel loading mass accounting for 10 to 30% of the hydrogenation catalyst and the selection of Al 2 o 3 The mass is calculated at 2.5 g, and the load is calculated as the nickel metal load to calculate the amount of metal salt nickel nitrate, the amount of nickel metal is 0.28~0.83g), dissolved in 100mL of water, and then added 2.5g Al 2 o 3 , immersion reaction at 80°C for 10h, rotary eva...

Embodiment 1

[0023] In a stirred pressure reactor, add a hydrogenation catalyst Ni / Al with a nickel loading mass fraction of 10% 2 o 3 100 mg, 1.0 g of 1,5-diaminonaphthalene (NDA), 9.0 ml of tetrahydrofuran, replace the air in the reactor with hydrogen three times, then fill in hydrogen to make the reaction pressure of the reactor reach 4.0 MPa, start stirring, and the stirring speed is 300 r / min, and heating the reaction kettle to make the reaction temperature reach 220 °C, replenish and maintain the reaction pressure at 7.0 MPa, react at constant temperature for 6 h, take out the reaction product, filter the catalyst after cooling, and obtain 1,5-diaminodeca Hydronaphthalene (H 10 NDAs). Using gas chromatography analysis, the conversion rate of 1,5-diaminonaphthalene (NDA) was 100%, and the conversion rate of 1,5-diaminodecalin (H 10 NDA) selectivity was 95.4%.

Embodiment 2

[0025] In a stirred pressure reactor, add a hydrogenation catalyst Ni / Al with a nickel loading mass fraction of 10% 2 o 3 100 mg, 2.0 g of 1,5-diaminonaphthalene (NDA), 8.0 ml of tetrahydrofuran, replace the air in the reactor with hydrogen three times, then fill in hydrogen to make the reaction pressure of the reactor reach 4.0 MPa, start stirring, and the stirring speed is 300 r / min, and heating the reaction kettle to make the reaction temperature reach 220 °C, replenish and maintain the reaction pressure at 7.0 MPa, react at constant temperature for 6 h, take out the reaction product, filter the catalyst after cooling, and obtain 1,5-diaminodeca Hydronaphthalene (H 10 NDAs). Using gas chromatography analysis, the conversion rate of 1,5-diaminonaphthalene (NDA) was 100%, and the conversion rate of 1,5-diaminodecalin (H 10 NDA) selectivity was 95.8%.

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Abstract

The invention relates to a method for preparing 1,5-diamino-decahydronaphthalene (H10NDA) by catalytic hydrogenation of 1,5-diaminonaphthalene (NDA), and is characterized in that: adding NDA and a solvent in a pressure reaction kettle, adding a load type nickel hydrogenation catalyst in an amount of 2.5 to 10% by mass, based on the addition amount of the reaction substrate NDA, replacing air in the reaction kettle with hydrogen for three times, then inletting hydrogen to make the reaction pressure of the reaction kettle reach 4.0 MPa, starting to stir, heating the reaction kettle to make the temperature reach 190 to 230 DEG C, replenishing hydrogen and maintaining the reaction pressure of the reaction kettle of 6 to 8 MPa, undergoing a thermostatic reaction for 5 to 8 h, and filtering out the catalyst after cooling to obtain H10NDA. The method can significantly improve the NDA conversion rate; and at the same time, the catalyst has low cost, simple preparation and long service life, and shows a good application prospect.

Description

Technical field [0001] The present invention involves a 1,5-diosamine (NDA) catalyzed hydrogen hydrogenation and preparation of 1,5-diosamidomyl hydrogen (H 10 The method of NDA) is specific to a load-load nickel-based hydrogen hydrogenation catalyst catalytic 1,5-diodes (NDA) hydrogenation to prepare 1,5-diosamidal hydrogen (H 10 NDA) method. Background technique [0002] 1,5-diodes (NDA) have gradually increased in the application of organic synthesis, pigment, dye medicine, pesticide, rubber auxiliary, resin, and photosensitive materials in recent years.The demand for 1,5-bentisocyanate has increased, and the number of synthesis research on various countries has continued to increase.However, at home and abroad to 1,5-dihydrial hydrogen hydrogenation and hydrogenation products 1,5-dihamine-based hydrogen (H 10 NDA) research and applications are rarely reported. [0003] The study of hydrogenation catalysts is a hot topic for long -term attention at home and abroad.Although it ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/38C07C209/72B01J23/755B01J29/14B01J29/46B01J29/035B01J29/76B01J29/85
Inventor 刘新泰夏清华鲁新环
Owner 武汉椿岭科技有限公司
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