Method for purifying adipodinitrile (ADN)

Patent metadata

Field	Value
Publication number	US-9822067-B2
Application number	US-201515116541-A
Country	US
Kind code	B2
Filing date	Feb 3, 2015
Priority date	Feb 7, 2014
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

The present invention relates to a process for purifying adiponitrile (ADN), wherein crude ADN is introduced into a rectification apparatus (R 1 ). The rectification apparatus (R 1 ) comprises a first side draw and preferably also a second side draw, the first side draw being disposed below the crude ADN introduction point and the optional second side draw being disposed above the crude ADN introduction point. The first side draw is used to draw off a gaseous stream comprising ADN while the optional second side draw is used to draw off undesired by-products such as 1-amino-2-cyanocyclopentene (ACCP) which are often generated in ADN production and consequently may be present in the crude ADN. The gaseous stream from the first side draw of (R 1 ) is introduced into a second rectification apparatus (R 2 ). (R 2 ) is used to separate off ADN from remaining high boilers and any other by-products present, pure ADN being drawn off from (D 2 ) as overhead product. It is preferable when the process according to the invention employs crude ADN from a reaction of butadiene with hydrocyanic acid (HCN).

First claim

The invention claimed is:

1. A process for purifying adiponitrile (ADN), comprising:
a) introducing a stream (S 1 ) comprising crude adiponitrile (ADN) into a rectification apparatus (R 1 );
b) separating off a gaseous stream (S 2 ) via a first side draw of (R 1 ), wherein the first side draw of (R 1 ) is disposed below the introduction point for introducing stream (S 1 ) into (R 1 ) and wherein gaseous stream (S 2 ) comprises AND; and
c) introducing gaseous stream (S 2 ) into a second rectification apparatus (R 2 ), wherein an ADN stream (S 7 ) depleted in high boilers (HB) is drawn off from (R 2 ) as overhead product and a liquid stream (S 6 ) enriched in high boilers (HB) is drawn off from (R 2 ) as bottoms.

2. The process according to claim 1 , further comprising at least one of steps d), e) and f):
d) separating off a stream (S 3 ) via a second side draw of rectification apparatus (R 1 ), wherein the second side draw of (R 1 ) is disposed above the introduction point for introducing stream (S 1 ) into (R 1 ), and wherein stream (S 3 ) comprises 1-amino-2-cyanocyclopentene (ACCP);
e) separating off a stream (S 5 ) as overhead product from rectification apparatus (R 1 ), wherein stream (S 5 ) comprises pentenenitriles (PNs); or
f) separating off a stream (S 4 ) from the bottom of rectification apparatus (R 1 ), wherein stream (S 4 ) comprises high boilers (HB).

3. The process according to claim 1 , wherein the crude ADN in stream (S 1 ) comprises adiponitrile (ADN), pentenenitriles (PNs), high boilers (HB), 1-amino-2-cyanocyclopentene (ACCP), 2-methylglutaronitrile (2-MGN) and 2-ethylsuccinonitrile (2-ESN).

4. The process according to claim 2 , wherein:
i) stream (S 4 ) comprises high boilers and ADN and is liquid; or
ii) stream (S 3 ) comprises ACCP, 2-MGN and 2-ESN and is liquid; or
iii) the gaseous stream (S 2 ) comprises ADN, high boilers and no more than 500 ppm of PNs, ACCP, 2-MGN or 2-ESN.

5. The process according to claim 4 , wherein in the gaseous stream (S 2 ) the total amount of PNs, ACCP, 2-MGN and 2-ESN in (S 2 ) is no more than 500 ppm.

6. The process according to claim 5 , wherein the total amount of PNs, ACCP, 2-MGN and 2-ESN is no more than 100 ppm.

7. The process according to claim 1 , wherein a stream (S 8 ) comprising crude ADN and high boilers (HB) is introduced into an evaporation apparatus (E 3 ), wherein a stream (S 1 ) depleted in non-volatile high boilers (HB) compared to stream (S 8 ) is discharged from (E 3 ) and passed into rectification apparatus (R 1 ), and wherein a stream (S 9 ) which comprises non-volatile high boilers and is depleted in ADN compared to stream (S 8 ) is discharged from (E 3 ).

8. The process according to claim 7 , wherein stream (S 9 ) is discharged from the bottom of evaporation apparatus (E 3 ) and passed into an evaporation apparatus (E 4 ), wherein a stream (S 10 ) depleted in non-volatile high boilers compared to stream (S 9 ) is discharged from (E 4 ) and passed into rectification apparatus (R 1 ) or returned to evaporation apparatus (E 3 ), and wherein a stream (S 11 ) depleted in ADN compared to stream (S 9 ) is discharged from (E 4 ).

9. The process according to claim 2 , wherein some or all of stream (S 4 ) is passed from rectification apparatus (R 1 ) into evaporation apparatus (E 3 ) or into evaporation apparatus (E 4 ).

10. The process according to claim 1 , wherein gaseous stream (S 2 ) is introduced into the bottom of (R 2 ) and pure ADN is drawn off from (R 2 ) as overhead product.

11. The process according to claim 1 , wherein the ADN drawn off from (R 2 ) as overhead product has a purity of at least 99.0%.

12. The process according to claim 11 , wherein the ADN drawn off from (R 2 ) as overhead product has a purity of at least 99.8%.

13. The process according to claim 1 , wherein the total amount of PNs, ACCP, 2-MGN and 2-ESN in the ADN drawn off from (D 2 ) as overhead product is no more than 200 ppm.

14. The process according to claim 1 , wherein stream (S 6 ) comprising high boilers (HB) and ADN is drawn off from the bottom of (R 2 ) and some or all of said stream is returned to the bottom of rectification apparatus (R 1 ).

15. The process according to claim 1 , wherein rectification apparatuses (R 1 ) and (R 2 ) are each independently columns with structured packing.

16. The process according to claim 1 , wherein rectification apparatus (R 2 ) does not have an evaporator.

17. The process according to claim 1 , wherein the ADN present in the crude ADN is produced by a reaction of butadiene with hydrocyanic acid (HCN).

18. The process according to claim 1 , wherein the ADN production process comprises a first step of reacting butadiene with HCN in the presence of a nickel(0) phosphorous ligand catalyst complex (Ni—P cat) to afford 3-pentenenitrile (3-PN) and a second step of subsequently reacting 3-PN with HCN in the presence of the same Ni-P cat and a Lewis acid to afford ADN.

19. The process according to claim 1 , wherein the purified ADN is hydrogenated to afford hexamethylenediamine (HMD) in the presence of a hydrogenation catalyst.

20. The process according to claim 1 , wherein the purified ADN is hydrogenated to afford hexamethylenediamine (HMD) in the presence of a Raney nickel catalyst.

Assignees

• Basf Se
• BASF SE (Ellwanger & Baier Patentanwälte)

Inventors

• Luyken Hermann
• Pfab Peter
• Jungkamp Tim

Classifications

• C07C253/34 Primary

  Separation; Purification · CPC title

• C07C209/48

  by reduction of nitriles · CPC title

• C07C253/10

  to compounds containing carbon-to-carbon double bonds · CPC title