Naphthalene → 1,3,6-Naphthalenetrisulfonic acid

HRID 1164313Notes

Reaction equation

HRID 1164313 reaction equation
C1C2C(=CC=CC=2)C=CC=1.O[S:12]([OH:15])(=[O:14])=[O:13].[O:16]=[S:17](=[O:19])=[O:18].[C:20]1([S:38]([OH:41])(=[O:40])=[O:39])[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([S:30]([OH:33])(=[O:32])=[O:31])[C:24]=2[CH:23]=[C:22]([S:34]([OH:37])(=[O:36])=[O:35])[CH:21]=1>>[C:20]1([S:38]([OH:41])(=[O:40])=[O:39])[C:29]2[C:24](=[CH:25][C:26]([S:17]([OH:19])(=[O:18])=[O:16])=[CH:27][CH:28]=2)[CH:23]=[C:22]([S:34]([OH:37])(=[O:36])=[O:35])[CH:21]=1.[C:25]1([S:30]([OH:33])(=[O:32])=[O:31])[C:24]2[C:29](=[CH:20][CH:21]=[C:22]([S:34]([OH:37])(=[O:36])=[O:35])[CH:23]=2)[CH:28]=[C:27]([S:12]([OH:15])(=[O:14])=[O:13])[CH:26]=1

Participants

5

Reactant 3

HCID 931Naphthalene2×HCID 24681Fuming sulfuric acidHCID 81165Naphthalene-1,3,5-trisulfonic acid

Product 2

HCID 44381,3,6-Naphthalenetrisulfonic acidYield 21%HCID 119707921,3,7-Naphthalenetrisulfonic acidYield 4%

Procedure

Naphthalene is introduced at 30° to 35° C. into monohydrate (=100% strength H2SO4), 65% strength oleum being run in at the same time. The reaction mixture is kept at 50° C. for one hour, at 70° C. for one hour and at 90° C. for seven hours, until everything has dissolved. With this process the yield of naphthalene-1,3,5-trisulphonic acid is about 68%, based on the naphthalene employed. In addition, about 21% of naphthalene-1,3,6-trisulphonic acid and about 4 to 5% of naphthalene-1,3,7-trisulphonic acid are formed (see Example 6).

Workup

  1. dissolutionhas dissolved

Sources & evidence

ORD record
ord-59df7b0652ed4e688dafa666415fde6a
Source dataset
uspto-grants-1983_01
Patent number
US04369143

Reaction notes

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