# US 2014/0194643 A1 · Process for the Preparation of Aminonitrile and Diamine, and Corresponding Devices

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- Number: US 2014/0194643 A1
- Document ID: US20140194643A1
- Status: Published application
- Kind: A1
- Application number: 14/127,526
- Filed: 2011-07-07
- Published: 2014-07-10
- Earliest claimed: 2011-07-07
- Assignees: Solvay (Zhangjiagang) Specialty Chemicals Co., Ltd.; Rhodia Operations
- Inventors: Zhongjie Lu; Shiquan Diao; Xinjun Zhang; Peijun Xu
- Web page: https://patentgrep.com/patent/US20140194643A1

## CPC

- C07C 253/30: by reactions not involving the formation of cyano groups
- C07C 209/48: by reduction of nitriles
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The present invention relates to a continuous process for the preparation of an aminonitrile comprising the stages of: a) formation of the aminonitrile by reaction between an alkenyl nitrile, mixed with aminonitrile, and a monoamine introduced in molar excess with respect to the alkenyl nitrile; b) separation of the unreacted monoamine and the aminonitrile; c) reaction between the monoamine separated during stage b) and all or part of the alkenyl nitrile in order to form a mixture of aminonitrile and of unreacted alkenyl nitrile, with the alkenyl nitrile being introduced in molar excess with respect to the said monoamine; d) transfer of the mixture of aminonitrile and alkenyl nitrile resulting from stage c) to the reaction of stage a), and e) in the case where only a portion of the alkenyl nitrile is introduced during stage c), introduction of the remaining molar amount of alkenyl nitrile into the mixture of stage d).

## Claims

### Claim 1

A continuous process for the preparation of an aminonitrile comprising the stages of:
a) formation of an aminonitrile by reaction between an alkenyl nitrile, mixed with aminonitrile, and a monoamine introduced in molar excess with respect to the alkenyl nitrile;
b) separation of the unreacted monoamine and the aminonitrile;
c) reaction between the monoamine separated during said stage b) and all or part of the alkenyl nitrile in order to form a mixture of aminonitrile and of unreacted alkenyl nitrile, with the alkenyl nitrile being introduced in molar excess with respect to the said monoamine;
d) transfer of the mixture of aminonitrile and alkenyl nitrile resulting from said stage c) to the reaction of stage a), and e) in the case where only a portion of the alkenyl nitrile is introduced during stage c), introduction of the remaining molar amount of alkenyl nitrile into the mixture of said stage d);
the total molar amount of the alkenyl nitrile introduced during said stages c) and e) being equal to the molar amount of monoamine introduced during said stage a).

### Claim 2 (depends on 1)

The process according to claim 1, wherein the alkenyl nitrile is selected from the group consisting of linear and branched C2 to C4 alkenes wherein a hydrogen atom is replaced by a conjugated cyano group.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the monoamine is a secondary amine of general formula R1R2NH, wherein R1 and R2, which are identical or different, represent a linear or branched C1 to C4 alkyl.

### Claim 4 (depends on 1)

The process according to claim 1, wherein:
the alkenyl nitrile is acrylonitrile (AN);
the monoamine is dimethylamine (DMA); and
the aminonitrile is 3-(dimethylamino)propanenitrile (DMAPN).

### Claim 5 (depends on 1)

The process according to claim 1, wherein the total amount of monoamine introduced during said stages a) and c) is in molar excess with respect to the total amount of alkenyl nitrile.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the separation of said stage b) is carried out by distillation and/or flash distillation.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the separation of said stage b) is carried out at atmospheric pressure.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the separation of said stage b) is carried out under reduced pressure.

### Claim 9 (depends on 8)

The process according to claim 8, wherein the pressure is less than 0.9 bar.

### Claim 10 (depends on 8)

The process according to claim 8, for which wherein the pressure is between 0.1 and 0.8 bar.

### Claim 11 (depends on 1)

The process according to claim 1, wherein, during said stage c), the alkenyl nitrile is introduced in an excess of at least 1 mol % with respect to the monoamine

### Claim 12 (depends on 1)

The process for the preparation of a diamine, comprising the stages of:
(i) continuous preparation of an aminonitrile according to the process of claim 1; and
ii) reduction of the aminonitrile resulting from stage (i).

### Claim 13 (depends on 12)

The process according to claim 12, wherein the diamine is dimethylaminopropylamine (DMAPA).)

### Claim 14

A device for the preparation of an aminonitrile, comprising:
a reactor (1) for the reaction between an alkenyl nitrile, mixed with the aminonitrile, and a monoamine in molar excess with respect to the alkenyl nitrile, in order to form the aminonitrile;
a separation device (2) which makes possible the separation of the unreacted monoamine and the aminonitrile;
a device (3) for conveying the monoamine separated by means of the separation device (2) to a reactor (4);
a reactor (4) for the reaction between the monoamine separated by means of the device (2) and all or a portion of the alkenyl nitrile, in molar excess with respect to the monoamine, in order to form a mixture of aminonitrile and unreacted alkenyl nitrile; and
a device (5) for conveying the mixture of aminonitrile and alkenyl nitrile exiting from the reactor (4) to the reactor (1).)

### Claim 15 (depends on 14)

A device for the preparation of a diamine, comprising:
a device according to claim 14; and
a device (8) for conveying the aminonitrile separated by means of the device (2) to a reactor (9) in order to be subjected to a reduction reaction in order to form the diamine.

### Claim 16 (depends on 1)

The process according to claim 1 wherein the total amount of monoamine introduced during said stages a) and c) is in an excess of at least 0.1 mol %, with respect to the total amount of alkenyl nitrile.
