Phthalic Acid → Diglycidyl isophthalate

HRID 1955826Notes

Reaction equation

HRID 1955826 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([OH:6])=[O:5].[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl.[C:18](Cl)(=[O:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.[CH2:30]1[O:32][CH:31]1[CH2:33][OH:34]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:4]([O:6][CH2:26][CH:22]1[O:24][CH2:23]1)(=[O:5])[C:3]1[CH:2]=[CH:10][CH:9]=[C:8]([C:16]([O:34][CH2:33][CH:31]2[O:32][CH2:30]2)=[O:17])[CH:7]=1.[CH2:16]1[O:17][CH:15]1[CH2:13][O:5][C:4]([C:3]1[C:2]([C:1]([O:12][CH2:20][CH:19]2[O:28][CH2:18]2)=[O:11])=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:6].[C:18]([O:34][CH2:33][CH:31]1[O:32][CH2:30]1)(=[O:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23]([O:5][CH2:13][CH:15]2[O:17][CH2:16]2)=[O:24])=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 1017Phthalic AcidHCID 7488Terephthaloyl chlorideHCID 7835EpichlorohydrinHCID 11164Glycidol

Product 3

HCID 23600Diglycidyl isophthalateHCID 626291,2-Bis(2-oxiranylmethyl) 1,2-benzenedicarboxylateHCID 111271Diglycidyl terephthalate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

Diglycidyl isophthalate and diglycidyl orthophthalate were prepared by caustic treatment of the products from the catalytic reaction of the corresponding phthalic acid with an excess of epichlorohydrin. Diglycidyl terephthalate was prepared in toluene from terephthaloyl chloride, glycidol, and triethylamine.

Sources & evidence

ORD record
ord-96a7873b39fe4c5a92f5146df65224dd
Source dataset
uspto-grants-1998_07
Patent number
US05777045

Reaction notes

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