2-Methylbenzenesulfonic acid → Perylene

HRID 991374Notes

Reaction equation

HRID 991374 reaction equation
C1(C)C(S(O)(=O)=O)=CC=CC=1.COC1C=CC(N2C(=O)[C:25]3=[CH:26][CH:27]=[C:28]4[C:35]5=[CH:36][CH:37]=[C:38]6C(=O)N(C7C=CC(OC)=CC=7)C(=O)[C:40]7[CH:41]=[CH:42][C:33](=[C:34]5[C:39]6=7)[C:30]5[CH:31]=[CH:32][C:23](=[C:24]3[C:29]4=5)C2=O)=CC=1>O>[CH:36]1[C:35]2=[C:34]3[C:33]([C:30]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][C:28]2=5)[CH:23]=[CH:32][CH:31]=4)=[CH:42][CH:41]=[CH:40][C:39]3=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 80898Anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone, 2,9-bis(4-methoxyphenyl)-

Product 1

HCID 9142Perylene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

Toluene sulfonic acid (TSA, monohydrate, 250 g) was heated in a kettle to 115 to 120° C. until melted and perylene red 179 (83.3 g) was charged to the kettle at a rate of 10 g per 2 minutes. Upon completion of the charge, the mixture was stirred for 20 minutes and held at 115-120° C. for 2 hours. The reaction medium was allowed to solidify on cooling and reheated to 115 to 120° C. for another 6 hours to yield a conditioned pigment. Ice (500 g) and water (1L) were then added to the hot mixture with vigorous stirring. The resulting slurry was filtered and washed until it became a neutral presscake. The presscake was reslurried into three times its weight of water and placed in a pressure reactor. The slurry was heated to 140° C. under increased pressure for 4 hours cooled then treated with mineral spirits (80 g). The mixture was filtered, washed and dried to give a further conditioned perylene pigment product.

Workup

  1. waitheld at 115-120° C. for 2 hours
  2. temperatureon cooling
  3. waitreheated to 115 to 120° C. for another 6 hours
  4. customto yield a conditioned pigment
  5. filtrationThe resulting slurry was filtered
  6. washwashed until it
  7. customplaced in a pressure reactor
  8. temperatureunder increased pressure for 4 hours
  9. temperaturecooled
  10. additionthen treated with mineral spirits (80 g)
  11. filtrationThe mixture was filtered
  12. washwashed
  13. customdried

Sources & evidence

ORD record
ord-823ea6d507854cdfb740007fefab99d1
Source dataset
uspto-grants-2002_10
Patent number
US06464773B1

Reaction notes

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