Process for the production of dinitrotoluene

• US 6,258,986 B1
• Filed: 08/03/1995
• Issued: 07/10/2001
• Est. Priority Date: 08/11/1994
• Status: Expired due to Term

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Klingler, Uwe, Zimmerman, Jürgen, Wiechers, Gerhard, Wastian, Dietmar, Schieb, Thomas
• Primary Examiner(s): Jones, Dwayne C.
• Application Number:
  US08/511,028
• Time in Patent Office: 2,168 Days
• Field of Search: 568/934, 568/932, 568/927
• US Class Current: 568/934
• CPC Class Codes: C07C 201/08 by substitution of hydrogen atoms by nitro groups
• CPC Class Codes: C07C 205/06 having nitro groups bound to carbon atoms of six-membered aromatic rings

Abstract

Dinitrotoluene is produced by nitrating toluene with nitrating acid under adiabatic conditions in a manner such that some mononitrotoluene is present in reaction mixture. The nitration reaction mixture is then treated to remove at least 5% by weight of water before the reaction mixture is separated into an acid phase and an organic phase. The product dinitrotoluene is recovered from the organic phase. The acid phase may be recycled after nitric acid has been added to replace that which was used in the nitration reaction.

Claims

1. A continuous, single-stage process for the production of a dinitrotoluene isomer mixture comprising

A) reacting

toluene with a nitrating acid composed of

(a) from about 80 to about 100% by weight of inorganic constituents which include

(i) from about 60 to about 90% by weight of sulfuric acid,

(ii) from about 1 to about 20% by weight of nitric acid, and

(iii) at least 5% by weight of water, and

(b) from 0 to about 20% by weight of organic constituents which include

(i) at least 70% by weight dinitrotoluene isomers and

(ii) from 0 to 30% by weight by-products of the nitration process

under adiabatic conditions in amounts such that the molar ratio of nitric acid to toluene is at least 1.5:

1 and such that the ratio of mononitrotoluene to dinitrotoluene in the vapor condensate is from 10;

1 to 1;

5 and at least 5%by weight of mononitrotoluene, based on total weight of reaction product, remains in the reaction mixture,

B) removing at least 5% by weight of water from the reaction mixture of A),

C) removing the reaction mixture of B) at a temperature of at least 120°

C.,

D) separating the reaction mixture from C) into an acid phase and an organic phase containing dinitrotoluene,

E) recovering the dinitrotoluene from the organic phase separated in D).

2. The process of claim 1 in which the molar ratio of nitric acid to toluene in A) is about 1.8:

1.

3. The process of claim 1 in which the water is removed in B) by flash evaporation.

4. The process of claim 1 in which the water is removed in B) by flash evaporation with simultaneous supply of heat.

5. The process of claim 1 in which the water is removed in B) by distillation.

6. The process of claim 1 in which up to 0.6 mole of 50-100% by weight nitric acid is added to the reaction mixture before step D).

7. The process of claim 1 in which up to 0.3 mole of 50-100% by weight nitric acid is added to the reaction mixture before step D).

8. The process of claim 1 in which up to 0.2 mole of 50-100% by weight nitric acid is added to the reaction mixture before step D.

9. The process of claim 1 in which 50-100% by weight nitric acid is added to the acid phase from D).

10. The process of claim 1 in which 50-100% by weight nitric acid added to the acid phase from D) and the resultant acid mixture is recycled to step A).