4,4-Diaminodiphenylmethane → 2,6-Naphthalenedicarboxylic acid

HRID 1459875Notes

Reaction equation

HRID 1459875 reaction equation
C(N1C(=O)N(CCO)C(=O)N(CCO)C1=O)CO.C(OC)(=O)C1C=CC(C(OC)=O)=CC=1.[CH:33]1[C:42]2[C:37](=[CH:38][C:39]([C:43]([O:45]C)=[O:44])=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[C:47]([O:49]C)=[O:48].C1C(CC2C=CC(N)=CC=2)=CC=C(N)C=1>C1(C)C(O)=CC=CC=1.C(O)CO>[CH:33]1[C:42]2[C:37](=[CH:38][C:39]([C:43]([OH:45])=[O:44])=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[C:47]([OH:49])=[O:48]

Participants

7

Reactant 4

HCID 75774,4-DiaminodiphenylmethaneHCID 8441Dimethyl terephthalateHCID 132861,3,5-Tris(2-hydroxyethyl) isocyanurateHCID 61225Dimethyl-2,6-naphthalenedicarboxylate

Product 1

HCID 143572,6-Naphthalenedicarboxylic acid

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 335O-CresolSolvent

Procedure

72.9 g of ethylene glycol, 192.2 g of THEIC, 83.3 g of dimethyl terephthalate, 104.4 g of dimethyl 2,6-naphthalenedicarboxylate, 220.1 g of trimellitic anhydride, 112.0 g of 4,4'-diaminodiphenylmethane and 0.7 g of tetra-n-butyl titanate are heated at 200° C. to prepare a polyesterimide resin. 96.8 g of distillate are obtained. At 200° C., the batch is diluted with 808.5 g of cresol. The cooled cresolic solution is diluted with 288.5 g of solvent naphtha and catalysed with 11.4 g of cresyl titanate.

Workup

  1. customto prepare a polyesterimide resin
  2. custom96.8 g of distillate are obtained

Sources & evidence

ORD record
ord-d8afe60cb70f47e2b262902aa68a8235
Source dataset
uspto-grants-1998_12
Patent number
US05854334

Reaction notes

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