Method for production of 1,5-pentanediamine by chemical decarboxylation of L-lysine and separation and extraction method

A technology of amino acid chemistry and extraction method, applied in the field of chemical intermediate preparation, can solve problems such as few reports, and achieve the effects of low cost, mild reaction conditions and environmental friendliness

Active Publication Date: 2019-08-20
郑州中科新兴产业技术研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, looking for a method for preparing 1,5-pentanediamine by chemical lysine decarboxylation with simple operation and low pollut...

Method used

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  • Method for production of 1,5-pentanediamine by chemical decarboxylation of L-lysine and separation and extraction method
  • Method for production of 1,5-pentanediamine by chemical decarboxylation of L-lysine and separation and extraction method
  • Method for production of 1,5-pentanediamine by chemical decarboxylation of L-lysine and separation and extraction method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] A kind of L-lysine chemical decarboxylation produces the method for 1,5-pentanediamine, and its steps are:

[0041] 1) Dissolve 15.9mmoL of L-lysine dihydrochloride (L-Lysine dihydrochloride) in 90mL of citric acid-disodium hydrogen phosphate buffer solution (pH 5);

[0042] 2) Add 20mL of N-bromosuccinimide (NBS) in dimethylformamide (DMF) solution dropwise to the solution in step 1) at 25°C, and react for 30 minutes;

[0043]3) Add 96.5moL of nickel chloride hexahydrate to the reaction solution in step 2), and gradually add 158mmoL of sodium borohydride powder in a small amount, and react for 1h in an ice-water bath.

[0044] Above-mentioned a kind of L-lysine chemical decarboxylation produces 1, the separation and extraction method of 5-pentanediamine, and its steps are:

[0045] a) Filter the obtained solution containing 1,5-pentanediamine with diatomaceous earth as a filter aid, and dilute the filtrate to 500 mL;

[0046] b) Add the diluted filtrate to a column o...

Embodiment 2

[0053] A kind of L-lysine chemical decarboxylation produces the method for 1,5-pentanediamine, and its steps are:

[0054] 1) Dissolve 15.9mmoL of L-lysine dihydrochloride (L-Lysine dihydrochloride) in 90mL of citric acid-disodium hydrogen phosphate buffer solution (pH 5);

[0055] 2) Add 20mL of N-bromosuccinimide (NBS) in dimethylformamide (DMF) solution dropwise to the solution in step 1) at 25°C, and react for 30 minutes;

[0056] 3) Add 96.5moL of cobalt chloride hexahydrate to the reaction solution in step 2), and gradually add 158mmoL of sodium borohydride powder in small amounts, and react for 1h in an ice-water bath.

[0057] Above-mentioned a kind of L-lysine chemical decarboxylation produces 1, the separation and extraction method of 5-pentanediamine, and its steps are:

[0058] a) Filter the obtained solution containing 1,5-pentanediamine using diatomaceous earth as a filter aid, and dilute the filtrate to 500 mL;

[0059] b) Add the diluted filtrate to a column ...

Embodiment 3

[0066] A kind of L-lysine chemical decarboxylation produces the method for 1,5-pentanediamine, and its steps are:

[0067] 1) Dissolve 15.9mmoL of L-lysine dihydrochloride (L-Lysine dihydrochloride) in 90mL of citric acid-disodium hydrogen phosphate buffer solution (pH 5);

[0068] 2) Add 20mL of N-bromosuccinimide (NBS) in dimethylformamide (DMF) solution dropwise to the solution in step 1) at 25°C, and react for 30 minutes;

[0069] 3) Add 96.5moL of ferric chloride to the reaction solution in step 2), and gradually add 158mmoL of sodium borohydride powder in small amounts, and react for 1h in an ice-water bath.

[0070] Above-mentioned a kind of L-lysine chemical decarboxylation produces 1, the separation and extraction method of 5-pentanediamine, and its steps are:

[0071] a) Filter the obtained solution containing 1,5-pentanediamine using diatomaceous earth as a filter aid, and dilute the filtrate to 500 mL;

[0072] b) Add the diluted filtrate to a column of strongly ...

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Abstract

The invention provides a method for production of 1,5-pentanediamine by chemical decarboxylation of L-lysine and a separation and extraction method. The method of the invention comprises the followingsteps: (1) dissolving L-lysine or L-lysine hydrochloride in a citric acid-disodium hydrogen phosphate buffer solution; (2) dropwise adding an oxidizer solution into the buffer solution obtained in the Step (1), and reacting at 10-75 DEG C for 20-30 min; and (3) adding transition metal salt into a reaction solution obtained in the Step (2), and simultaneously adding a reducing agent and mixing intensely and reacting for 20-120 min so as to obtain a 1,5-pentanediamine solution. According to the invention, L-lysine or its hydrochloride is used as a raw material to undergo an oxidative decarboxylation reaction and a cyan reduction reaction to obtain 1,5-pentanediamine. The reaction has mild conditions, is easy to operate and has good repeatability. By using cation exchange resin to contact with the 1,5-pentanediamine solution, the method of the invention is low-cost and environmentally-friendly in comparison with existing 1,5-pentanediamine separation methods.

Description

technical field [0001] The invention relates to the technical field of preparation of chemical intermediates, in particular to a method for producing 1,5-pentanediamine by chemical decarboxylation of L-lysine and a separation and extraction method. Background technique [0002] 1,5-pentamethylenediamine, similar to hexamethylenediamine, is polymerized with dibasic acid to produce nylon 5X (nylon 54, nylon 56, etc.), the performance is comparable to or even surpasses the classic nylon 66, and its main application fields are fibers (such as clothing, automobiles, etc.) Tire cords, carpets and pipes, etc.) and engineering plastics (such as electronic instrument products and automotive parts, etc.). The total global demand for nylon exceeds 7 million tons per year, and the market demand for hexamethylenediamine as a raw material for nylon has exceeded 2 million tons per year. Although the market demand is strong, the raw materials are monopolized by foreign companies, and my co...

Claims

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Application Information

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IPC IPC(8): C07C211/09C07C209/78C07C209/84
CPCC07C209/78C07C209/84C07C211/09
Inventor 李辉赵珂珂马占玲张延强
Owner 郑州中科新兴产业技术研究院
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