Ammonia → Disperse Blue 60

HRID 867963Notes

Reaction equation

HRID 867963 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].[NH2:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:23])[C:12]=2[C:11]([NH2:24])=[C:10]2[C:25](=[O:29])N[C:27](=[O:28])[C:9]=12.N>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:25](=[O:29])[C:10]2[C:9](=[C:8]([NH2:7])[C:21]3[C:20](=[O:22])[C:19]4[C:14]([C:13](=[O:23])[C:12]=3[C:11]=2[NH2:24])=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:27]1=[O:28]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 16723-MethoxypropylamineHCID 671921,4-Diamino-2,3-anthraquinonedicarboximide

Product 1

HCID 25530Disperse Blue 60Yield 130%

Conditions

Temperature
40 °C

Procedure

225.2 g of 3-methoxypropylamine are charged to a 750 ml sulfonating flask and heated to 40° C. With stirring, 141.2 g of 1,4-diaminoanthraquinone-2,3-dicarboximide are added over 3 hours. The ensuing reaction is slightly exothermic, with evolution of NH3. The viscous suspension is stirred for another hour at 40°-45° C., then cooled to 20° C. and further stirred for one hour. The precipitated product is filtered with suction and washed with 300 ml of methanol and then with 300 ml of water, affording 226.6 g of N-(3-methoxypropyl)-1,4-diaminoanthraquinone-2,3-dicarboximide [dye of formula (3)]. After optional replenishment with fresh 3-methoxypropylamine, the mother liquor can be re-used for a new batch.

Workup

  1. customThe ensuing reaction
  2. stirringThe viscous suspension is stirred for another hour at 40°-45° C.
  3. temperaturecooled to 20° C.
  4. stirringfurther stirred for one hour
  5. filtrationThe precipitated product is filtered with suction
  6. washwashed with 300 ml of methanol

Sources & evidence

ORD record
ord-2c32d5e55c684fa6b36788a07bce72fd
Source dataset
uspto-grants-1988_10
Patent number
US04777266

Reaction notes

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