Hydrochloric Acid → 1,2,4,5-Benzenetetraamine

HRID 6328Notes

Reaction equation

HRID 6328 reaction equation
C1(C(O)=O)C2C(C(O)=O)=CC=C(C(O)=O)C=2C(C(O)=O)=CC=1.Cl.Cl.Cl.Cl.[NH2:27][C:28]1[CH:33]=[C:32]([NH2:34])[C:31]([NH2:35])=[CH:30][C:29]=1[NH2:36].Cl>>[NH2:27][C:28]1[CH:33]=[C:32]([NH2:34])[C:31]([NH2:35])=[CH:30][C:29]=1[NH2:36]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 314221,4,5,8-Naphthalenetetracarboxylic acidHCID 782601,2,4,5-Benzenetetraamine tetrahydrochloride2×

Product 1

HCID 782611,2,4,5-Benzenetetraamine

Procedure

BBL can be prepared by a two step dehydrohalogenationpolycondensation sequence using 1,4,5,8-naphthalene tetracarboxylic acid (NTCA) and 1,2,4,5-tetraaminobenzene tetrahydrochloride (TABH). Initially, TABH was heated with polyphosphoric acid to to liberate hydrogen chloride gas and to afford 1,2,4,5-tetraaminobenzene in situ. Next, NTCA and then phosphorous pentoxide are added to the vessel and then heated under an inert and anhydrous atmosphere to effect polycondensation of NTCA and TABH in approximately equimolar amounts. This product is high melting and metallic golden-green in appearance.

Workup

  1. customBBL can be prepared by a two step dehydrohalogenationpolycondensation sequence

Sources & evidence

ORD record
ord-ac4984dcd66740e9b259f2a6fd748e68
Source dataset
uspto-grants-1993_09
Patent number
US05248580

Reaction notes

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