Nitric Acid → Naphthalene

HRID 484960Notes

Reaction equation

HRID 484960 reaction equation
[C:1]1(S(O)(=O)=O)[C:10]2[C:5](=[CH:6][C:7](S(O)(=O)=O)=[CH:8][CH:9]=2)[CH:4]=[C:3](S(O)(=O)=O)[CH:2]=1.[N+]([O-])(O)=O>S(=O)(=O)(O)O>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 44381,3,6-Naphthalenetrisulfonic acid

Product 1

HCID 931Naphthalene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

For example, the industrially important 8-nitronaphthalene-1,3,6-trisulphonic acid (nitro-T-acid) is prepared by nitrating the isomer mixture of naphthalenetrisulphonic acids which is obtained in the trisulphonation of naphthalene with sulphuric acid and oleum and contains, as the main constituent, naphthalene-1,3,6-trisulphonic acid, with nitric acid in sulphuric acid, as the solvent (see F.I.A.T., Final Report 1016, pages 32-39). In the preparation process known from the literature, a procedure is followed in which the hot solution of the naphthalenetrisulphonic acids in sulphuric acid, which solution has a temperature of 150° to 155° C. and is obtained in the trisulphonation of naphthalene, is cooled to 100° C., diluted with water and cooled further to 80° C. The batch is then transferred to the nitration kettle, cooled in this kettle to 35° to 40° C. and nitrated with mixed acid (86% of nitric acid, 12% of sulphuric acid and 2% of water) at 35° to 40° C. in the course of about 10 hours.

Workup

  1. customa temperature of 150° to 155° C.

Sources & evidence

ORD record
ord-f8a36de0a6514cf7ac85a554494208c3
Source dataset
uspto-grants-1985_08
Patent number
US04534905

Reaction notes

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