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Hydrochloric Acid → Perylene

HRID 1413330
Notes
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Reaction equation

HRID 1413330 reaction equation
C(O)(=O)CCCCCCCCCCCCCCCCC.[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(N)CCCCCCCCCCCCCCCCC.Cl>[K].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.[OH-].[K+].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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 5281Stearic AcidHCID 15793OctadecylamineHCID 86737471HCID 86737471, compound

Product 1

HCID 9142Perylene

Reagents, catalysts & solvents 4

HCID 3776IsopropanolSolvent
HCID 14797
Potassium Hydroxide
Solvent
2×
HCID 5462222PotassiumSolvent
HCID 19063515Perylene-1,2,3,4-tetracarboxylic acidSolvent

Procedure

27.4 parts of crude perylenetetracarboxylic dianhydride in the form of the potassium salt of perylenetetracarboxylic acid are dissolved in aqueous potassium hydroxide solution as described in Example 1. To this solution are added 2 parts of stearic acid, dissolved in 60 parts by volume of 1% potassium hydroxide solution. With stirring, the alkaline perylenetetracarboxylic acid/stearic acid solution is added dropwise in the course of 15 minutes at 60° C. to a suspension consisting of 1.4 parts of MgCl2.6H2O, 0.7 parts of stearylamine, 35 parts by volume of about 37% aqueous hydrochloric acid and 60 parts by volume of isopropanol. 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 cold water and dried in a vacuum cabinet at 80° C., affording 29.8 parts of a perylene pigment with properties as good as those of the pigment of Example 1.

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 cold water
  5. customdried in a vacuum cabinet at 80° C.

Sources & evidence

ORD record
ord-87b70f3364c44a2c930935bdf9f06233
Source dataset
uspto-grants-1981_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04250079

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes