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Preparation method of N,N'-dialkyl m-phenylenediamine

A technology of dialkanoyl m-phenylenediamine and alkyl m-phenylenediamine, applied in the N field, can solve the problems such as unreported synthesis patents, and achieve high reaction yield, enhanced controllability, and mild reaction conditions. Effect

Active Publication Date: 2014-01-29
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] N,N'-diethyl-m-phenylenediamine is a new functional monomer designed based on N,N'-dimethyl-m-phenylenediamine, and its synthesis patent has not yet been reported

Method used

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  • Preparation method of N,N'-dialkyl m-phenylenediamine
  • Preparation method of N,N'-dialkyl m-phenylenediamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1N

[0027] Embodiment 1N, the synthesis of N'-diformyl m-phenylenediamine

[0028] In 100mL equipped with magnetic stirring, thermometer, reflux condenser and N2 Add formic acid (0.2mol, 9.206g), 45mL toluene and m-phenylenediamine (0.05mol, 5.407g) into the protected four-necked flask, react under reflux for 3h, set up a water trap after cooling to room temperature, and then heat until separation The liquid in the lower layer of the water tank did not increase any more. Continue heating to distill the toluene out and recover it. After cooling, add 6mLTHF and 6mL ether, stir to precipitate the crude product, filter, wash the filter cake with 15mL ether and dry to obtain a white solid (7.886g) , which is N, N'-diformyl m-phenylenediamine, the product yield is 96.2%, and the purity by liquid chromatography analysis is 100%.

[0029] The above reaction can be done in a few more pots, as the raw material for the next step reaction.

Embodiment 2

[0030] Embodiment 2N, the synthesis of N'-diformyl m-phenylenediamine

[0031] In 100mL equipped with magnetic stirring, thermometer, reflux condenser and N 2 Add formic acid (0.3mol, 13.809g), 30mL toluene and m-phenylenediamine (0.05mol, 5.407g) into the protected four-necked flask, react under reflux for 0.5h, set up a water separator after cooling to room temperature, and then heat until The liquid in the lower layer of the water separator does not increase anymore, continue heating to distill the toluene out and recover, add 6mLTHF and 6mL ether after cooling, stir, and precipitate the crude product, filter, wash the filter cake with 15mL ether and dry to obtain a white solid (7.659g ), which is N, N'-diformyl m-phenylenediamine, the product yield is 93.4%, and the purity by liquid chromatography analysis is 100%.

[0032] The above reaction can be done in a few more pots, as the raw material for the next step reaction.

Embodiment 3

[0033] Embodiment 3N, the synthesis of N'-diformyl m-phenylenediamine

[0034] In 100mL equipped with magnetic stirring, thermometer, reflux condenser and N 2 Add formic acid (0.2mol, 9.206g), 30mL toluene and m-phenylenediamine (0.05mol, 5.407g) into a protected four-necked flask, react for 2h under reflux, set up a water trap after cooling to room temperature, and then heat until separation The liquid in the lower layer of the water tank did not increase any more. Continue heating to distill the toluene out and recover it. After cooling, add 2mL THF and 10mL diethyl ether, stir to precipitate the crude product, filter, wash the filter cake with 15mL diethyl ether and dry to obtain a white solid (7.897g) , which is N, N'-diformyl m-phenylenediamine, the product yield is 96.3%, and the purity by liquid chromatography analysis is 100%.

[0035] The above reaction can be done in a few more pots, as the raw material for the next step reaction.

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Abstract

The invention discloses a preparation method of N,N'-dialkyl m-phenylenediamine, which comprises the following steps: enabling NaBH4, I2, N,N'-dialkyl acyl m-phenylenediamine and THF (Tetrahydrofuran) as a solvent to react for 0.5 to 2 hours at the temperature of 5 to 10 DEG C; heating to 50 DEG C to the reflux temperature to react; and postprocessing the reaction solution to prepare the N,N'-dialkyl m-phenylenediamine after completely finishing a TCL monitoring reaction, wherein the amount ratio of the NaBH4 to the N,N'-dialkyl acyl m-phenylenediamine is 3-6:1; and the amount ratio of the I2 to the N,N'-dialkyl acyl m-phenylenediamine is 1-2:1. Compared with a LiAlH4 reduction system, the invention has the advantages that the reduction system does not require strict anhydrous reaction environment so that the solvent does not required to be dehydrated; the reductibility is milder than the reductibility of the LiAlH4; the safety and the controllability are greatly enhanced; the by-products are reduced so that the yield is obviously enhanced; and the highest yields of N,N'-dimethyl m-phenylenediamine and N,N'-diethyl m-phenylenediamine can respectively reach 77.6% and 85.5%.

Description

(1) Technical field [0001] The invention relates to a method for preparing N, N'-dialkyl m-phenylenediamine, in particular to a method for preparing N, N'-dialkyl m-phenylenediamine by using m-phenylenediamine as a basic raw material. (2) Background technology [0002] N, N'-dialkyl m-phenylenediamine is a kind of polyamine, which can form amide bonds with polyacid chlorides to prepare reverse osmosis membranes, in which N, N'-dimethyl m-phenylenediamine and N, N'-di Ethyl-m-phenylenediamine is especially meaningful for the preparation of oxidation-resistant reverse osmosis composite membranes. [0003] In 2003, T.Shintani's group published a patent on the synthesis of N,N'-dimethyl-m-phenylenediamine. Their synthesis method is: add formic acid to acetic anhydride at 0°C, heat up to 60°C to generate mixed anhydride, add tetrahydrofuran as a solvent, cool to 0°C, add m-phenylenediamine, keep at this temperature for reaction, and decompress the reaction solution The solvent ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/51C07C209/50
Inventor 刘立芬茅佩卿徐振元高从堦
Owner ZHEJIANG UNIV OF TECH
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