Carbon Dioxide → Solvent Red 49

HRID 2295700

Reaction equation

HRID 2295700 reaction equation
[CH3:1][CH2:2][N:3]([C:6]1[CH:7]=[CH:8][C:9]2[C:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[C:31](C)=[O:32])=[C:23]3[C:13](=[CH:14][C:15]([CH:21]=[CH:22]3)=[N+:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[O:12][C:10]=2[CH:11]=1)[CH2:4][CH3:5].C(N(CC)C1C=C([OH:43])C=CC=1)C.C1(=O)OC(=O)C2=CC=CC=C12.C(=O)=O.[OH-].[Na+]>O>[CH3:5][CH2:4][N:3]([C:6]1[CH:7]=[CH:8][C:9]2[C:24]3([O:32][C:31](=[O:43])[C:30]4[C:25]3=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:23]3[CH:22]=[CH:21][C:15]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:14][C:13]=3[O:12][C:10]=2[CH:11]=1)[CH2:2][CH3:1]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 6811Phthalic AnhydrideHCID 70623-(Diethylamino)phenolHCID 14798Sodium HydroxideHCID 45271881[9-(2-Acetylphenyl)-6-(diethylamino)xanthen-3-ylidene]-diethylazanium

Product 1

HCID 62357Solvent Red 49Yield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

The Rhodamine dye of formula (II), Rhodamine B free base (Colour Index 45170:1), a well-known pigment, can be prepared by heating a stirred mixture of 10 parts by weight of m-diethylaminophenol and 12 parts by weight of phthalic anhydride to 175° C. under a blanket of carbon dioxide. The reaction mixture is stirred at 170°-175° C. for a period of 6-7 hours, then cooled to 40° C. and discharged into water. The pH of the resulting slurry is adjusted to 12 by adding caustic soda, and the insoluble material is recovered by filtration. The filter cake is then rinsed with water and dried to obtain Rhodamine B Base in a yield about 90% of theoretical.

Workup

  1. temperatureby heating
  2. filtrationthe insoluble material is recovered by filtration
  3. washThe filter cake is then rinsed with water
  4. customdried

Sources & evidence

ORD record
ord-ed8de1c0e85242978067f03c34f2e41e
Source dataset
uspto-grants-1984_01
Patent number
US04426205

Linked notes

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