IP Library Granted Patent US 9,776,956
Granted Patent B2
US 9,776,956 · App. 15/355,108 · Granted Oct 3, 2017

Method for preparing N,N′-bis(2-cyanoethyl)-1,2-ethylenediamine by using cation exchange resin as catalyst

Inventors: Te-Chao Liao (Taipei, TW); Jung-Jen Chuang (Taipei, TW); Zhi-Ming Huang (Taipei, TW); Shun-Chi Chen (Taipei, TW); Tzu-Chiang Lin (Taipei, TW)
Assignee: NAN YA PLASTICS CORPORATION
C07C253/18
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Quick Facts
Patent No.
US 9,776,956
App. No.
15/355,108
Granted
Oct 3, 2017
Kind
B2
Abstract

A method for preparing N,N′-bis(2-cyanoethyl)-1,2-ethylenediamine involves using strongly acidic cation exchange resin as a catalyst for synthesis, and is advantageous for not only eliminating the need of distillation for purification and thereby reducing reaction time, but also improving the yield of N,N′-bis(2-cyanoethyl)-1,2-ethylenediamine to 97.70-98.08%; and the method benefits simplified process and reduced costs and helps to save water significantly, thereby minimizing environmental pollution.

Claims (14)

1. A method for preparing N,N′-bis(2-cyanoethyl)-1,2-ethylenediamine, comprising steps of: taking ethylenediamine and acrylonitrile at a molar ratio therebetween of 1:1.9-2.1 as reactants to perform synthesis reaction in the presence of strongly acidic cation exchange resin for 5-30 minutes at a temperature of 20-70° C. thereby obtaining N,N′-bis(2-cyanoethyl)-1,2-ethylenediamine with a yield of 97.7% or more; wherein the strongly acidic cation exchange resin is sulfonic-acid-based or carboxylic-acid-based cation exchange resin and is used in an amount of 50-100 wt % based on a weight of the ethylenediamine reactant.

2. The method of claim 1 , wherein the strongly acidic cation exchange resin is bead-form sulfonic-acid-based or carboxylic-acid-based cation exchange resin, with an average diameter (D 50 ) of 0.1-1.0 mm and has a total exchange capacity greater than 1.7 eq/L.

3. The method of claim 1 , wherein the strongly acidic cation exchange resin is Amberlyst-15 or Amberlyst-36 cation exchange resin.

4. The method of claim 2 , wherein the strongly acidic cation exchange resin is Amberlyst-15 or Amberlyst-36 cation exchange resin.

5. The method of claim 1 , wherein the molar ratio between ethylenediamine and acrylonitrile is 1:2.06.

6. The method of claim 2 , wherein the molar ratio between ethylenediamine and acrylonitrile is 1:2.06.

7. The method of claim 1 , wherein the synthesis reaction performs continuously for 5-30 minutes at room temperature of 25° C.

8. The method of claim 2 , wherein the synthesis reaction performs continuously for 5-30 minutes at room temperature of 25° C.

9. The method of claim 1 , wherein the acrylonitrile is added dropwise into a reactor.

10. The method of claim 2 , wherein the acrylonitrile is added dropwise into a reactor.

11. The method of claim 1 , wherein the acrylonitrile is continuously added but not added dropwise into a reactor.

12. The method of claim 2 , wherein the acrylonitrile is continuously added but not added dropwise into a reactor.

13. The method of claim 11 , wherein the acrylonitrile is added into the reactor simultaneously with ethylenediamine in a continuous manner.

14. The method of claim 11 , wherein the acrylonitrile is added into the reactor simultaneously with the cation exchange resin in a continuous manner.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2016
From: LIAO, TE-CHAO; CHUANG, JUNG-JEN; HUANG, ZHI-MING; CHEN, SHUN-CHI; LIN, TZU-CHIANG
To: NAN YA PLASTICS CORPORATION
Reel/Frame 040365/0056 →
Priority Claims (1)
TW 104139365 A · Nov 26, 2015 · national
Continuity (1)
Related Publication 20170152216A1 · Jun 1, 2017