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Method for preparing 1, 5-pentanediamine by one-step chemical decarboxylation of L-lysine

A lysine, pentamethylene diamine technology, applied in chemical instruments and methods, organic chemistry, chemical/physical processes, etc., can solve the problems of difficult separation, low product concentration, low lysine decarboxylase activity, etc. The effect of short process, low energy consumption and good environmental friendliness

Active Publication Date: 2020-04-07
郑州中科新兴产业技术研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention proposes a method for preparing 1,5-pentanediamine by one-step chemical decarboxylation of L-lysine, which solves technical problems such as low lysine decarboxylase activity, low product concentration and difficult separation in the biological fermentation method

Method used

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  • Method for preparing 1, 5-pentanediamine by one-step chemical decarboxylation of L-lysine
  • Method for preparing 1, 5-pentanediamine by one-step chemical decarboxylation of L-lysine
  • Method for preparing 1, 5-pentanediamine by one-step chemical decarboxylation of L-lysine

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Embodiment 1

[0026] A method for preparing 1,5-pentanediamine by one-step chemical decarboxylation of L-lysine, the steps are as follows:

[0027] (1) Catalyst preparation

[0028] Preparation of Fe / SiO with 5% Loading by Equal Volume Impregnation 2 Catalyst, the specific preparation steps are: weigh 1.075 g of ferric nitrate, dissolve it in 10 ml of water, and obtain a red clear solution. Add 5 g of silica carrier to the solution, stir evenly, dry in an oven at 100 °C overnight, and then calcinate in a muffle furnace at 550 °C with a heating rate of 5 °C / min. After calcination for 240 min, a red sample is obtained. Reduction of Fe / SiO at 350 ℃ under hydrogen / argon atmosphere 2 catalyst.

[0029] (2) Decarboxylation reaction

[0030] Take 1 mmol of lysine and 10 ml of water in a reaction kettle with a volume of 25 ml, stir until the raw material of lysine is completely dissolved, add 5mol% Fe / SiO 2 catalyst, the pH was adjusted to 3.0 with phosphoric acid after stirring for 5 min. Af...

Embodiment 2

[0034] A method for preparing 1,5-pentanediamine by one-step chemical decarboxylation of L-lysine, the steps are as follows:

[0035] (1) Catalyst preparation

[0036] Preparation of Fe / SiO with 1% Loading by Equal Volume Impregnation 2 Catalyst, the specific preparation steps are: weigh 0.215 g of ferric nitrate, dissolve it in 10 ml of water, and obtain a red clear solution. Add 5 g of silica carrier to the solution, stir evenly, dry in an oven at 100 °C overnight, and then calcinate in a muffle furnace at 550 °C with a heating rate of 5 °C / min. After calcination for 240 min, a red sample is obtained. Reduction of Fe / SiO at 350 ℃ under hydrogen / argon atmosphere 2 catalyst.

[0037] (2) Decarboxylation reaction

[0038] Take 1 mmol of lysine and 10 ml of water in a reaction kettle with a volume of 25 ml, stir until the raw material of lysine is completely dissolved, add 5mol% Fe / SiO 2 catalyst, the pH was adjusted to 3.0 with phosphoric acid after stirring for 5 min. Af...

Embodiment 3

[0040]A method for preparing 1,5-pentanediamine by one-step chemical decarboxylation of L-lysine, the steps are as follows:

[0041] (1) Catalyst preparation

[0042] Preparation of Fe / SiO with 10% Loading by Equal Volume Impregnation 2 Catalyst, the specific preparation steps are: weigh 2.15 g of ferric nitrate, dissolve it in 10 ml of water, and obtain a red clear solution. Add 5 g of silica carrier to the solution, stir evenly, dry in an oven at 100 °C overnight, and then calcinate in a muffle furnace at 550 °C with a heating rate of 5 °C / min. After calcination for 240 min, a red sample is obtained. Reduction of Fe / SiO at 350 ℃ under hydrogen / argon atmosphere 2 catalyst.

[0043] (2) Decarboxylation reaction

[0044] Take 1 mmol of lysine and 10 ml of water in a reaction kettle with a volume of 25 ml, stir until the raw material of lysine is completely dissolved, add 5mol% Fe / SiO 2 catalyst, the pH was adjusted to 3.0 with phosphoric acid after stirring for 5 min. Aft...

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Abstract

The invention provides a method for preparing 1, 5-pentanediamine by one-step chemical decarboxylation of L-lysine, which comprises the following steps: putting lysine or a lysine salt, water and a solid catalyst into a high-pressure reaction kettle, and reacting to obtain a pentanediamine water solution. According to the method, a supported metal oxide is used as the catalyst, water is used as agreen solvent, a high-pressure reaction kettle is used as a reactor, a reaction is carried out for a certain time, and the yield of pentanediamine in a solution obtained after the reaction can reach 80%. The method is short in technological process and low in energy consumption, a heterogeneous catalyst is adopted, the product separation difficulty is reduced, meanwhile, the reaction is carried out in a water system, no extra organic solvent is introduced, and the method has good environmental friendliness and very wide industrial application prospects.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for preparing 1,5-pentanediamine through one-step chemical decarboxylation of L-lysine. Background technique [0002] 1,5-pentanediamine, also known as cadaverine, can be polymerized with adipic acid to produce nylon 56 material. Nylon 56 material has good comprehensive properties, such as high moisture absorption and perspiration rate, good air permeability, softness and dyeing performance, etc., and it is wear-resistant, chemical-resistant, flame-retardant and easy to process. Among the nylon material series Have a strong competitive advantage. Adiponitrile, the upstream raw material of nylon 66, is monopolized by foreign companies (Invista and Rohidia, etc.), which has become a bottleneck technology that restricts the rapid development of my country's nylon industry. Nylon 56 has excellent properties comparable to nylon 66 and can be used as an alternative material...

Claims

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Application Information

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IPC IPC(8): C07C209/68C07C211/09B01J29/46B01J29/40B01J23/78B01J23/755B01J23/745B01J23/46
CPCC07C209/68B01J23/745B01J23/755B01J23/462B01J23/78B01J29/40B01J29/46B01J2229/18C07C211/09
Inventor 张延强马占玲李祥李辉常立玉
Owner 郑州中科新兴产业技术研究院
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