Phthalic Anhydride → Naptalam

HRID 1460269Notes

Reaction equation

[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]1([NH2:22])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>>[C:12]1([NH:22][C:4](=[O:5])[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1]([OH:6])=[O:11])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 6811Phthalic Anhydride

HCID 86401-Naphthylamine

Product 1

HCID 8594NaptalamYield 96%

Procedure

To a 30 mm co-rotating twin screw extruder (Werner & Pfleiderer ZSK type) was added at barrel 1 (of 14) 2370 g (16 mol) per hour phthalic anhydride in the form of crushed pellets, and at barrel 2 molten 1-naphthylamine at a rate of 2234 g (15.62 mol) per hour while maintaining a temperature profile of: zone 1=75°, zone 2=83°, zone 3=95°, zone 4= 75° and zone 5=45° C. At a screw speed of 300 rpm, the residence time was about 60 seconds, resulting in a product containing N-1-naphthylphthalamic acid (4365 g, ca. 96% yield based on 1-naphthylamine).

Workup

customresulting in a product

Sources & evidence

ORD record: ord-3002776ed7014850a01d13388a31f6d0
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05070197

Reaction notes

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