Nitrobenzene → Quinoline Yellow

HRID 1361115Notes

Reaction equation

HRID 1361115 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH:13]1[C:18](C(O)=O)=[CH:17][C:16]2[C:22]([O:24][C:25](=O)[C:15]=2[CH:14]=1)=[O:23].[N+](C1C=CC=CC=1)([O-])=O>>[CH:8]1[CH:9]=[C:10]2[CH:11]=[CH:12][C:3]([CH:2]3[C:25](=[O:24])[C:15]4[C:16](=[CH:17][CH:18]=[CH:13][CH:14]=4)[C:22]3=[O:23])=[N:4][C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 7416NitrobenzeneHCID 11089Trimellitic anhydrideHCID 731962-Quinolinemethanol

Product 1

HCID 6731Quinoline Yellow

Procedure

As shown by this reaction scheme (5), a hydroxyquinaldine derivative and a trimellitic acid anhydride derivative are added to nitrobenzene, and the mixture is heated and stirred at a refluxing temperature for several hours. Subsequently, the product is collected by filtration and washed with methanol, then dried, to yield the quinophthalone compound of the present invention. Here, a process of removing impurity substances such as inorganic salts can be included. The quinophthalone compound and mixed colorant in the present invention preferably have decreased contents of impurity substances such as inorganic salts, whereby the mechanical properties of the thermoplastic resin can be well maintained, and the anti-migration property and anti-sublimation property can be improved. The content of these impurity substances is desirably not more than 2%.

Workup

  1. customAs shown by this reaction scheme (5)
  2. temperaturethe mixture is heated
  3. filtrationSubsequently, the product is collected by filtration
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-5bb1eddd21744e53b10dd9940e4b864e
Source dataset
uspto-grants-2011_02
Patent number
US07879929B2

Reaction notes

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