Hydrochloric Acid → Perylene

HRID 1413331Notes

Reaction equation

HRID 1413331 reaction equation
C(N)CCCCCCCCCCCCCCCCC.Cl.[C:21]1(C(O)=O)[C:38]2=[C:39]3[C:28]([C:29]4[C:40]5[C:33](=[CH:34][CH:35]=[CH:36][C:37]2=5)[CH:32]=[CH:31][CH:30]=4)=[CH:27][CH:26]=[C:25](C(O)=O)[C:24]3=[C:23](C(O)=O)[C:22]=1C(O)=O.C(O)(=O)CCCCCCCCCCCCCCCCC>C(O)(C)C>[CH:36]1[C:37]2=[C:40]3[C:29]([C:28]4[C:39]5[C:24](=[CH:23][CH:22]=[CH:21][C:38]2=5)[CH:25]=[CH:26][CH:27]=4)=[CH:30][CH:31]=[CH:32][C:33]3=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15793OctadecylamineHCID 86737471HCID 86737471, compound

Product 1

HCID 9142Perylene

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.7 part of stearylamine are dissolved warm in 60 ml of isopropanol and to this solution are added 35 parts by volume of about 37% aqueous hydrochloric acid. With stirring, the alkaline perylenetetracarboxylic acid/stearic acid solution is added dropwise to this mixture in the course of 15 minutes at 60° C. The formation of the anhydride imide is brought to completion by stirring the acid suspension for 31/2 hours at reflux temperature. The red pigment suspension is then filtered at about 70° C. The filter cake is washed neutral with water and dried in a vacuum cabinet at 80° C., affording 29.8 parts of a perylene pigment which produces strong red colourations of excellent fastness properties when it is incorporated in alkylmelamine stoving lacquers.

Workup

  1. stirringby stirring the acid suspension for 31/2 hours
  2. temperatureat reflux temperature
  3. filtrationThe red pigment suspension is then filtered at about 70° C
  4. washThe filter cake is washed neutral with water
  5. customdried in a vacuum cabinet at 80° C.

Sources & evidence

ORD record
ord-d39caadeed884692848808eb2b13e5e1
Source dataset
uspto-grants-1981_02
Patent number
US04250079

Reaction notes

Loading…