Naphthalene → 1-Naphthalenesulfonic acid

HRID 1732491Notes

Reaction equation

HRID 1732491 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11]([O:14][C:15](=[O:17])[CH3:16])(=[O:13])[CH3:12].[S:18](=O)(=[O:21])([OH:20])[OH:19]>C(O)(=O)C>[C:9]1([S:18]([OH:21])(=[O:20])=[O:19])[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1.[C:11]([O:14][C:15](=[O:17])[CH3:16])(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 931Naphthalene2×HCID 1118Sulfuric AcidHCID 7918Acetic Anhydride

Product 2

HCID 68121-Naphthalenesulfonic acidHCID 7918Acetic Anhydride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

128 g (1 mole) of naphthalene are dissolved in 153 g (1.5 mole) of acetic anhydride. The resulting solution is added, under stirring, with 98 g (1 mole) of a 100% sulphuric acid for 95 minutes while gradually raising the temperature from 30° to 45° C. Further sulphonation of naphthalene is conducted at a temperature of 45° C. for an additional 45 minutes following the procedure described in the foregoing Example 1 to give 208 g of naphthalene-α-sulphonic acid, 145 g of glacial acetic acid and 25.5 g of acetic anhydride.

Workup

  1. additionThe resulting solution is added
  2. temperaturewhile gradually raising the temperature from 30° to 45° C

Sources & evidence

ORD record
ord-0ef6759e9da749a7be965b0e70b2838d
Source dataset
uspto-grants-1980_12
Patent number
US04237323

Reaction notes

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