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2,5-Dianilinoterephthalic acid → Quinacridone

HRID 2298703
Notes
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Reaction equation

HRID 2298703 reaction equation
[NH:1]([C:8]1[CH:16]=[C:15]([C:17](O)=[O:18])[C:14]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][C:9]=1[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(NC2C=C(C(O)=O)C(NC3C=CC(OC)=CC=3)=CC=2C(O)=O)=CC=1>CO>[CH:24]1[CH:25]=[C:26]2[C:17]([C:15]3[C:14]([NH:20][C:21]2=[CH:22][CH:23]=1)=[CH:13][C:9]1[C:10]([C:7]2[C:2]([NH:1][C:8]=1[CH:16]=3)=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:11])=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 823512,5-Dianilinoterephthalic acidHCID 30848371,4-Benzenedicarboxylic acid, 2,5-bis[(4-methoxyphenyl)amino]-

Product 1

HCID 13976Quinacridone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
112 °C

Procedure

A mixture (one part) of 2,5-dianilino-terephthalic acid (96%) and 2,5-dianisidino-terephthalic acid (4%) was dissolved in polyphosphoric acid (4 parts at 117.5%). The solution was heated and drowned into methanol as described in Example 3. The mixture was then heated for 4 hours at 112° C. to produce a transparent, beta-phase quinacridone pigment, which exhibited an X-ray diffraction spectrum identical to that of Examples 5 thus confirming the product to be a pure beta-phase quinacridone.

Workup

  1. temperatureThe solution was heated

Sources & evidence

ORD record
ord-a8d4a10c912e44bfb9c4c4176d2021e6
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06494949B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes