Naphthalene → 1,4-Naphthoquinone

HRID 485217Notes

Reaction equation

HRID 485217 reaction equation
S(=O)(=O)(O)[OH:2].[CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[OH2:16]>>[C:14]1(=[O:2])[C:15]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11](=[O:16])[CH:12]=[CH:13]1

Participants

4

Reactant 3

HCID 931NaphthaleneHCID 962WaterHCID 1118Sulfuric Acid

Product 1

HCID 85301,4-Naphthoquinone

Procedure

The process for the preparation of the quinone according to the present invention is usually conducted in the following manner. Namely, an aqueous sulfuric acid solution containing a predetermined amount of a ceric salt such as ceric sulfate, is reacted with a solution of the starting material such as naphthalene in the above-mentioned inert organic solvent immiscible with water according to the present invention, for a predetermined period of time under stirring at a predetermined temperature. Then, the solvent layer is separated from the aqueous layer. Some of the product still remaining in the aqueous layer is extracted with the above-mentioned organic solvent and combined to the separated solvent layer. The combined solvent layer is then treated depending upon the particularly purpose. For instance, for the purpose of obtaining a quinone such as 1,4-naphthoquinone, the solvent is removed under reduced pressure to obtain the product by precipitation or drying. Whereas, for the purpose of using it for the subsequent reaction step, the solvent layer is subjected to a proper treatment such as washing with water before subjecting it to the reaction step. The above process may be conducted by a multi-stage countercurrent process instead of conducting the above-mentioned reaction steps and the separation steps for the separation of the solvent layer from the aqueous layer by a combination of plurality of reactors and separation tanks.

Workup

  1. customThen, the solvent layer is separated from the aqueous layer
  2. extractionis extracted with the above-mentioned organic solvent
  3. additionThe combined solvent layer is then treated

Sources & evidence

ORD record
ord-eb9bc99b96c54badb9a64097e80d9710
Source dataset
uspto-grants-1985_08
Patent number
US04536337

Reaction notes

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