M-Phenylenediamine → Terephthalic Acid

HRID 1356482Notes

Reaction equation

HRID 1356482 reaction equation
CC1C(C)=C(C)C(C)=C(C)C=1.FC1C=[C:15]([O:21]B(O)O)C=C(F)C=1F.[C:25]1([NH2:32])[CH:30]=[CH:29][CH:28]=[C:27](N)[CH:26]=1.C(O)(=O)[C:34]1[CH:42]=[CH:41][CH:40]=[C:36]([C:37]([OH:39])=[O:38])[CH:35]=1.C[N:46]1CCCC1=[O:51]>>[CH:30]1[C:25]([NH2:32])=[CH:26][CH:27]=[C:28]([NH2:46])[CH:29]=1.[C:37]([OH:39])(=[O:38])[C:36]1[CH:35]=[CH:34][C:42]([C:15]([OH:21])=[O:51])=[CH:41][CH:40]=1

Participants

7

Reactant 5

HCID 7935M-PhenylenediamineHCID 8496Isophthalic AcidHCID 12784PentamethylbenzeneHCID 13387N-methyl-2-pyrrolidoneHCID 21870694HCID 21870694, compound

Product 2

HCID 7489Terephthalic AcidHCID 7814P-Phenylenediamine

Conditions

Temperature
200 °C

Procedure

Next, various aromatic dicarboxyic acids (4 mmol), various aromatic diamines (4 mmol), pentamethylbenzene (4 g), N-methylpyrrolidinone (NMP) (1 g), and 3,4,5-trifluorophenylboric acid (0.04 mmol) were poured into a Schlenk and stirred at 200° C. (temperature of oil bath) for one day. The other conditions were the same as in Example 2. When m-phenylenediamine and isophthalic acid were polycondensed as in chemical formula 2, the isolation yield of nomex was 99% or more. As to the isolation yield of keylar, the same result was obtained for a case of chemical formula 3, where p-phenylenediamine and terephthalic acid were polycondensed. The isolation yield of nomex was 97% for a case of chemical formula 4, where diaminodiphenylether and isophthatic acid were polycondensed. The isolation yield of tellurone was 42% for a case of chemical formula 5, where p-aminobenzoic acid was polycondensed.

Workup

  1. customAs to the isolation yield of keylar, the same result

Sources & evidence

ORD record
ord-bdb86a194e7748fca70f80e83e401b10
Source dataset
uspto-grants-2003_07
Patent number
US06586555B1

Reaction notes

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