# US 2013/0158296 A1 · Process for the synthesis of 1-amino-3-halo-4,6-dinitrobenzene

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- Number: US 2013/0158296 A1
- Document ID: US20130158296A1
- Status: Published application
- Kind: A1
- Application number: 13/517,052
- Filed: 2010-12-21
- Published: 2013-06-20
- Earliest claimed: 2009-12-21
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: Annalisa Hargis; Joachim C. Ritter
- Web page: https://patentgrep.com/patent/US20130158296A1

## CPC

- C07C 209/10: with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process is provided for the preparation of 1-amino-3-halo-4,6-dinitrobenzene and related compounds by monoamination of dihalodinitrobenzenes by ammonia in the presence of solvent and water. Using glycol as a solvent for the dihalodinitrobenzene and feeding ammonia at a rate at which it is consumed allows for the synthesis of high purity product, such as 1-amino-3-chloro-4,6-dinitrobenzene, at high yields.

## Claims

### Claim 1

A process for preparing a compound represented by Formula (II):
wherein Z is Cl or Br; R1 and R2 are each independently H, alkyl, or aryl; and R3 and R4, are each independently alkyl or aryl or may be joined to form an aliphatic ring structure;
by forming a reaction mixture comprising a compound represented by the structure of the following Formula (III)
and solvent, in the presence of ammonia and about 2 to about 25 wt % water, wherein the ammonia is fed at about the rate at which it is consumed; and heating the reaction mixture between about 60° C. and about 140° C. to convert the compound represented by the structure of Formula (III) to the compound represented by the structure of Formula (II).

### Claim 2 (depends on 1)

A process according to claim 1 wherein each Z is Cl.

### Claim 3 (depends on 2)

A process according to claim 2 wherein Z═Cl and R1, R2, R3, and R4 are each H.

### Claim 4 (depends on 1)

A process according to claim 1 wherein the solvent comprises an aliphatic dihydric alcohol.

### Claim 5 (depends on 4)

A process according to claim 4 wherein the aliphatic dihydric alcohol is ethylene glycol.

### Claim 6 (depends on 1)

A process according to claim 1 wherein the reaction mixture is prepared by contacting a suspension of a compound represented by Formula (III) in solvent and water with gaseous ammonia.

### Claim 7 (depends on 1)

A process according to claim 1 wherein the reaction mixture is prepared by contacting a suspension of a compound represented by Formula (III) in solvent with an aqueous solution of ammonia.

### Claim 8 (depends on 1)

A process according to claim 1 wherein the reaction mixture is prepared by contacting a compound represented by Formula (III) with a feed stream containing solvent, water and NH3.

### Claim 9 (depends on 8)

A process according to claim 8 wherein the amount of water is between about 1 and about 5 times the amount of NH3.

### Claim 10 (depends on 1)

A process according to claim 1 wherein the compound represented by Formula (II) thereby produced is filtered and washed with solvent and then water.

### Claim 11 (depends on 10)

A process according to claim 10 wherein the filtrate containing solvent is collected and distilled, and the solvent is recovered and recycled to the reaction mixture.

### Claim 12 (depends on 1)

A process according to claim 1 wherein the compound represented by Formula (II) thereby produced is slurried with water as a suspension and transferred to another reactor for further processing.

### Claim 13 (depends on 1)

A process according to claim 1 further comprising:
(a) admixing a 1,3-dihalobenzene, which is represented by the structure of the following Formula (IX):
wherein each X is independently Cl or Br, with fuming nitric acid, sulfuric acid, and SO3 to form a reaction mixture that is characterized by (i) a concentration of nitric acid therein that is in the range of about 2.0 to about 2.3 moles per mole of 1,3-dihalobenzene; (ii) a concentration of SO3 therein that is in the range of about 1 to about 3 moles per mole of 1,3-dihalobenzene; (iii) a concentration of 1,3-dihalobenzene therein that is in the range of about 12 to about 24 weight percent; and (iv) a temperature of up to about 120° C.; and
(b) stirring the reaction mixture at a temperature in the range of about −10° C. to about 70° C. to form a 1,3-dihalo-4,6-dinitrobenzene product;
to provide a 1,3-dihalo-4,6-dinitrobenzene for incorporation into the reaction mixture in the process of claim 1.