Perylene-1,2,3,4-tetracarboxylic acid → Octadecylamine

HRID 1413329Notes

Reaction equation

HRID 1413329 reaction equation
C1(C(O)=O)C2=C3C(C4C5C(=CC=CC2=5)C=CC=4)=CC=C(C(O)=O)C3=C(C(O)=O)C=1C(O)=O.[CH2:33]([NH2:51])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50].C(O)(C)C.Cl>>[CH2:33]([NH2:51])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

Participants

3

Reactant 2

HCID 19063515Perylene-1,2,3,4-tetracarboxylic acid2×HCID 86737470HCID 86737470, compound

Product 1

HCID 15793Octadecylamine

Procedure

The alkaline perylenetetracarboxylic acid solution is added dropwise to the stearylamine/isopropanol/hydrochloric acid suspension in the course of 15 minutes at 60° C., whereupon the perylenetetracarboxylic acid precipitates. The formation of the anhydride imide is brought to completion by boiling the still acid suspension for 3 hours at reflux temperature. The red pigment suspension is filtered at about 70° C. The filter cake is washed neutral with cold water and dried in a vacuum cabinet at 80° C., affording 28.8 parts of stearylamine-modified perylene-3,4,9,10-tetracarboxylic dianhydride pigment. When incorporated in powder form in plasticised PVC rolled sheets, this pigment produces strong, red colourations of excellent fastness properties and has extremely good dispersibility.

Workup

  1. customprecipitates
  2. customfor 3 hours
  3. temperatureat reflux temperature
  4. filtrationThe red pigment suspension is filtered at about 70° C
  5. washThe filter cake is washed neutral with cold water
  6. customdried in a vacuum cabinet at 80° C.

Sources & evidence

ORD record
ord-27c55aeacb914aa39f82de31df4a5f17
Source dataset
uspto-grants-1981_02
Patent number
US04250079

Reaction notes

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