Preparation of perylen-3,4:9,10-tetracarboxylic dianhydride...

Details Preparation of perylen-3,4:9,10-tetracarboxylic dianhydride... Preparation of perylen-3,4:9,10-tetracarboxylic dianhydride...

2007-12-13

2010-10-05

Andres, Janet L. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S098000

Reexamination Certificate

active

07807836

ABSTRACT:
A process for preparing perylene-3,4:9,10-tetracarboxylic dianhydride, comprising: dimerizing a naphthalene-1,8-dicarboximide of the formula IIa;reoxidizing the resulting alkali metal salt of the leuco form of the perylene-3,4:9,10-tetracarboxylic diimide of the formula Ia;hydrolyzing the diimide to the tetraalkali metal salt of perylene-3,4:9,10-tetracarboxylic acid in the presence of an inert organic solvent, of an alkali metal base and of water; and subjecting the tetraalkali metal salt of perylene-3,4:9,10-tetracarboxylic acid to the action of an aqueous inorganic acid to convert it into perylene-3,4:9,10-tetracarboxylic dianhydride; wherein R3is cyclohexyl or phenyl which may each be substituted by up to three C1-C4-alkyl radicals, and the dimerizing is in a substantially homogeneous reaction medium consisting essentially of an apolar aprotic organic solvent and an alkali metal base.

REFERENCES:
patent: 2487105 (1949-11-01), Cornwell
patent: 3446810 (1969-05-01), Dien et al.
patent: 4197111 (1980-04-01), Pallos et al.
patent: 4919848 (1990-04-01), Harnisch
patent: 276 9256 (1913-10-01), None
patent: 0 054 806 (1980-12-01), None
patent: 0 525 538 (1993-02-01), None
patent: 141 431 (1977-03-01), None
patent: 3-223282 (1991-10-01), None
patent: 9-194746 (1997-07-01), None
patent: 78 458 (1975-07-01), None
Holtrup et al DN 126:36159a Chem. Abs (1997).
Frank O. Holtrup, et al. “Terrylenimides: New NIR Fluorescent Dyes” Chem. Eur. J. 1997, 3, No. 2 (pp. 219-225).
Sakamoto, Takaaki et al. “Oxidative Coupling Reaction of 1,8-Naphthalimide a new synthetic methodology for the production of Perylene-3,4,9,10-Tetracarboximide”, Kawamura Rikagaku Kenkyusho Hokoku, vol. 8, pp. 85-95, with English abstract & full English translation, (1997).
Sakamoto, Takaaki et al. “A ‘Green’ Route to Perylene Dyes: Direct Coupling Reactions of 1,8-Naphthalimide and Related Compounds under Mild Conditions Using a “New” Base Complex Reagent, t-BuOK/DBN”, J. Org. Chem. vol. 66, pp. 94-98 2001.
Jankowski, Z. et al. “Synthesis and Properties of Some Derivatives of N-[4′-(1,2,3-Benzotriazolyl)-phenyl]-naphthalimide”, Pol. J. Chem, vol. 55, No. 3, pp. 555-563 (abstract only), (1981).
Ganin, E. V. et al. “N-Substituted Isonaphthalimides. Peculiarities of Their Formation and Their Reaction with Amines”, Zh. Org. Khim, vol. 21, No. 11, pp. 2415-2423 (abstract only) 1985.

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