Nitric Acid → Naphthalene

HRID 484961Notes

Reaction equation

HRID 484961 reaction equation
[C:1]1(S(O)(=O)=O)[C:10]2[CH:9]=[CH:8][CH:7]=[C:6](S(O)(=O)=O)[C:5]=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 81165Naphthalene-1,3,5-trisulfonic acid

Product 1

HCID 931Naphthalene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

The industrially important 8-nitronaphthalene-1,3,5-trisulphonic acid is prepared by nitrating the naphthalene-trisulphonic acid mixture which is obtained in the trisulphonation of naphthalene with sulphuric acid and oleum and which contains naphthalene-1,3,5-trisulphonic acid as the main constituent, with nitric acid using sulphuric acid as the solvent (see F.I.A.T. Final Report No. 1016, pages 42-44). According to this process, the hot solution, of the naphthalenetrisulphonic acids in sulphuric acid, which has a temperature of 90° C. and is obtained in the trisulphonation of naphthalene is transferred to the nitration kettle and, after cooling to 60° C., diluted with water and nitrated with mixed acid (86% of nitric acid, 12% of sulphuric acid and 2% of water) at 30° to 35° C. The nitration mixture is subsequently stirred at 40° C. for 1 hour. As a repetition of the process has shown, the yield of 8-nitronaphthalene-1,3,5-trisulphonic acid is only about 46%, relative to the naphthalene-1,3,5-trisulphonic acid employed (see Example 16 of the present Application).

Workup

  1. customa temperature of 90° C.

Sources & evidence

ORD record
ord-b093b8a3348349afa46ea2053a69f7c6
Source dataset
uspto-grants-1985_08
Patent number
US04534905

Reaction notes

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