Method for producing nitrobenzene by adiabatic nitriding

Patent metadata

Field	Value
Publication number	US-9284255-B2
Application number	US-201314413277-A
Country	US
Kind code	B2
Filing date	Jul 23, 2013
Priority date	Jul 27, 2012
Publication date	Mar 15, 2016
Grant date	Mar 15, 2016

Abstract

The invention relates to an adiabatic process for producing nitrobenzene by nitrating benzene with sulphuric acid mixtures and nitric acid mixtures using a stoichiometric excess of benzene and reusing non-reacted benzene, the content of the aliphatic organic compounds in the feed benzene being limited, by the targeted evacuation of aliphatic organic compounds to at least one step in the process, to a content of less than 1.5 mass-%, in relation to the total amount of feed benzene.

First claim

The invention claimed is:

1. A continuous adiabatic process for the preparation of nitrobenzene by the nitration of benzene in a nitration unit, comprising:
a) reacting a benzene-containing stream (a.1), comprising at least 90 wt % of benzene, based on the total weight of (a.1), in a reactor with a mixture of sulfuric acid (a.2) and nitric acid (a.3) under adiabatic conditions, the benzene being used in a stoichiometric excess, based on nitric acid (a.3),
b) separating the process product obtained in step a) in a phase separation apparatus into an aqueous phase (b.1) comprising sulfuric acid and an organic phase (b.2) comprising nitrobenzene,
c) concentrating the aqueous phase (b.1) obtained in step b) by evaporation of the water to give an aqueous phase (c.1) having a higher sulfuric acid concentration than (b.1), and recycling all or part of the phase (c.1) into step a) and using the phase (c.1) as a component of (a.2), and
d) working up the organic phase (b.2) obtained in step b) to pure nitrobenzene (d.1) to give a benzene-containing stream (d.2), all or part of which is used as a component of (a.1) in the nitration unit of step a),
wherein
aliphatic organic compounds are specifically removed from the process at at least one point so that only such a benzene-containing stream (a.1) having a content of aliphatic organic compounds of less than 1.5 wt %, based on the total weight of (a.1), is fed into the reactor.

2. An adiabatic process for the preparation of nitrobenzene by the nitration of benzene in a series of two nitration units (100, 200) each having at least one reactor (1, 1*), comprising:
a) reacting exclusively benzene (a.1.1) having a content of aliphatic organic compounds of less than 1.5 wt %, based on the total weight of (a.1.1), in the reactor (1) of the first, continuously operating nitration unit (100) with a mixture of sulfuric acid (a.2.1) and nitric acid (a.3.1) under adiabatic conditions, the benzene being used in a stoichiometric excess, based on nitric acid (a.3.1),
b) separating the process product obtained in step a) in a phase separation apparatus (2) into an aqueous phase (b.1.1) comprising sulfuric acid and an organic phase (b.2.1) comprising nitrobenzene,
c) concentrating the aqueous phase (b.1.1) obtained in step b) by evaporation of the water to give an aqueous phase (c.1.1) having a higher sulfuric acid concentration than (b.1.1), and recycling all or part of the phase (c.1.1) into step a) and using the phase (c.1.1) as a component of (a.2.1), and
d) working up the organic phase (b.2.1) obtained in step b) to pure nitro-benzene (d.1.1) to give a benzene-containing stream (d.2.1),
and reacting the benzene-containing stream (d.2.1) in a reactor (1*) of the second, continuously or discontinuously operating nitration unit (200) with a mixture of sulfuric acid (a.2.2) and nitric acid (a.3.2) under adiabatic conditions to give nitrobenzene, the benzene being used in, a stoichiometric excess, based on nitric acid (a.3.2), of 2.0% to 20%, of theory, and then working up the nitrobenzene formed thereby to pure nitrobenzene.

3. The process according to claim 1 , wherein the aliphatic organic compounds are selected from the group consisting of cyclohexane, heptane, methylcyclohexane, bicycloheptane, isomers of dimethylcyclopentane, ethylcyclopentane, pentane, cyclopentane and 2-methylhexane.

4. The process according of claim 1 , wherein the pressure measured relative to atmospheric pressure in the gas phase of the phase separation apparatus used in step b) is adjusted to a value of 20 mbar to 200 mbar, wherein the temperature in the phase separation apparatus used in step b) is adjusted to a value of 100° C. to 140° C., and wherein aliphatic organic compounds are removed with the gas phase of the phase separation apparatus used in step b).

5. The process according to claim 4 , further comprising feeding an inert gas into the phase separation apparatus in order to assist the removal of the aliphatic organic compounds, the aliphatic organic compounds being removed together with said inert gas via an off-gas line connected to the gas space of the phase separation apparatus.

6. The process according to claim 2 , further comprising separating the process product obtained in the adiabatic reaction in the reactor (1*) in a phase separation apparatus (2*) into an aqueous phase (b.1.2) comprising sulfuric acid and an organic phase (b.2.2) comprising nitrobenzene, and the organic phase (b.2.2)=(15*) being freed of aliphatic organic compounds and excess benzene in a distillation column (7*) and then mixed with the organic phase (b.2.1)=(15) of the first nitration unit (100).

7. The process according to claim 1 , further comprising working up all or part of the removed aliphatic organic compounds by distillation to recover benzene removed together with the aliphatic organic compounds.

8. The process according to claim 7 , further comprising using all or part of the recovered benzene as a component of the stream (a.1) or (a.1.1).

9. The process according to claim 2 wherein the aliphatic organic compounds are selected from the group consisting of cyclohexane, heptane, methylcyclohexane, bicycloheptane, isomers of dimethylcyclopentane, ethylcyclopentane, pentane, cyclopentane and 2-methylhexane.

10. The process according to claim 2 , wherein the pressure measured relative to atmospheric pressure in the gas phase of the phase separation apparatus used in step b) is adjusted to a value of 20 mbar to 200 mbar, wherein the temperature in the phase separation apparatus used in step b) is adjusted to a value of 100° C. to 140° C., and wherein aliphatic organic compounds are removed with the gas phase of the phase separation apparatus used in step b).

11. The process according to claim 10 , further comprising feeding an inert gas into the phase separation apparatus in order to assist the removal of the aliphatic organic compounds, the aliphatic organic compounds being removed together with said inert gas via an off-gas line connected to the gas space of the phase separation apparatus.

12. The process according to claim 9 , further comprising separating the process product obtained in the adiabatic reaction in the reactor (1*) in a phase separation apparatus (2*) into an aqueous phase (b.1.2) comprising sulfuric acid and an organic phase (b.2.2) comprising nitrobenzene, and the organic phase (b.2.2)=(15*) being freed of aliphatic organic compounds and excess benzene in a distillation column (7*) and then mixed with the organic phase (b.2.1)=(15) of the first nitration unit (100).

13. The process according to claim 10 , further comprising separating the process product obtained in the adiabatic reaction in the reactor (1*) in a phase separation apparatus (2*) into an aqueous phase (b.1.2) comprising sulfuric acid and an organic phase (b.2.2) comprising nitrobenzene, and the organic phase (b.2.2)=(15*) being freed of aliphatic organic compounds and excess benzene in a distillation column (7*) and then mixed with the organic phase (b.2.1)=(15) of the first nitration unit (100).

14. The process according to claim 11 , further comprising separating the process product obtained in the adiabatic reaction in the reactor (1*) in a phase separation apparatus (2*) into an aqueous phase (b.1.2) comprising sulfuric acid and an organic phase (b.2.2) comprising nitrobenzene, and the organic phase (b.2.2)=(15*) being freed of aliphatic organic compounds and excess benzene in a distillation column (7*) and then mixed with the organic phase (b.2.1)=(15) of the first nitration unit (100).

15. The process according to claim 2 , wherein the be

Assignees

• Bayer Materialscience Ag

Inventors

• Knauf Thomas
• Racoes Alexandre
• Dohmen Wolfgang
• Mairata Antoni

Classifications

• C07C201/06 Primary

  Preparation of nitro compounds · CPC title

• C07C205/06

  having nitro groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C201/08 Primary

  by substitution of hydrogen atoms by nitro groups · CPC title

• C07C201/16

  Separation; Purification; Stabilisation; Use of additives · CPC title