Naphthalic acid anhydride

Naphthalic acid anhydride (110 g, 0.556 mole), glycine (48 g, 0.64 mole) and dimethylformamide (750 ml) are heated and stirred at reflux for 2 hr. The homogeneous dark solution is cooled to about 100°C and 750 ml of hot water is added slowly to the stirred solution. The reaction mixture is cooled and allowed to stand in a refrigerator for 16 hr. The precipitate is collected and recrystallized from ethanol, using decolorizing charcoal, to give the title compound, MP 271°-272°C. 

Since the dye is patented, it is probable that it is represented by one of the five examples in the patent. The most likely possibility is example 3, the condensation product from 4-amino-l,8-naphthalic acid anhydride with cyclohexylamine, or example 4, the sulfonation product of this compound. 

Naphthalic acid anhydride, ethyl malonate, and anhydrous ZnCU heated 4 hrs. at 170-175° crude 2-chloro-l,3-dioxo-2,3-dihydrophenalene heated and shaken ca. 2 min. with coned. HNOg and glacial acetic acid on a water bath until a red soln. results -> 2-chloro-2-nitro-l,3-dioxo-2,3-dihydrophenalene (Y 70%) heated 15 min. at 120° l,2,3-trioxo-2,3-dihydrophenalene (Y 95%). Overall Y 60-65%. W. Ried and M. L. Mehrotra, A. 718, 120 (1968). 

The process to manufacture the perylene chromophore is basically unchanged since its discovery in the early 1900s. The reaction sequence begins with catalyzed air oxidation of a coal tar extract, acenaphthene (2), to produce naphthalic acid anhydride (3). There are several catalysts, such as V2OS, that are used Commercially in this oxidation reaction. Naphthahc acid anhydride is available from several global suppliers in a range of purities. 

Naphthalic acid imide 69 is obtained through air oxidation of acenaphthene 72 with vanadium peroxide as a catalyst. The intermediate, naphthalic anhydride 73, is subsequently reacted with ammonia ... 

On reaction with zinc dust in alkaline medium, naphthalic acid is subjected to reductive dimerization with so-called deoxynaphthalic anhydride 366 as the result (13CB1484). The formation of diarylnaphthalides 371 on... 

The most common compounds from the naphtho[crf]pyran series are naphthalic anhydride and its various derivatives 378 substituted in the naphthalene nucleus. These derivatives are formed on heating naphthalic acids 377, which are obtained on oxidation of the corresponding acenaph-thenes. The syntheses of naphthalic acids 377 and their anhydrides are described in a monograph (66MI1). The interaction between naphthalic acid and sulfur tetrafluoride leads to 2,2,9,9-tetrafluoronaphtho[cd]pyran 379 (73ZOR689). 

Naphthalic anhydride has been prepared by the hydrolysis of the dinitrile of, 2-naphthalic acid,1 by the oxidation of suitably substituted hydrocarbons or ketones,2 or by the dehydrogenation of the 3,4-dihydro compound with bromine 3 or with sulfur.4... 

The naphthalimide ring system has the drawback of low effectiveness, which is mainly attributable to the low molar extinction coefficient. The industrial synthesis of alkoxynaphthalimides begins with acenaphthene. Chlorination and subsequent oxidation with dichromate give the corresponding naphthalic acids [116], which are converted to the anhydrides on drying. Mild reaction with methyla-mine, followed by reaction with sodium methoxide or sodium ethoxide, gives, e.g., 64 or 65. 

The majority of polynaphthylimides described in literature results from the interaction of naphthalene-1,4,5,8-tetracarboxylic acid anhydride with various diamines [156]. In addition, a series of bis(naphthalic anhydrides) with hinge groupings was employed in synthesis of polynaphthylimides. In particular, the... 

Phenylethynyl)-l,2-benzenedicarboxylic acid anhydride, 476, All 4-(l-Phenylethynyl)l,8-naphthalic anhydride, 487 4-(Phenylethynyl)phenol, 183 Phenylhydroquinone, 212 A -Phenylmaleimide, 150... 

A gently stirred mixture of 20 g. 1,8-naphthalic anhydride and PCI5 heated gradually to 160° until it melts, after ca. 1 hr., then refluxed 5 hrs. with vigorous stirring 20 g. 1,8-naphthalic acid chloride. J. Arient and J. Marhan, Goll. 28, 1292 (1963). 

Naphthalic anhydride [81-84-5] M 198.2, m 274°. Extracted with cold aqueous Na2C03 to remove free acid, then crystd from acetic anhydride. 

A solution of 66.5 g. (1.01 moles) of 85% potassium hydroxide in 300 ml. of water in an 800-ml. beaker is heated to 60-70 , and 100 g. (0.505 mole) of commercial 1,8-naphthalic anhydride (Note 1) is stirred in. The pH of the resultant deep-brown solution is adjusted to a value of 7 (Note 2) with 6N hydrochloric acid and 3N potassium hydroxide. It is treated with 10 g. of decolorizing carbon and filtered. This operation is repeated. The filtrate is concentrated in a 1.5-1. beaker on a steam bath to about 180 ml. The concentrate is cooled to room temperature, 800 ml. of methanol is added with vigorous stirring by hand, and the mixture is cooled to 0-5°. The precipitated dipotassium naphthalate is separated by filtration, washed with 150 ml. of methanol, and dried in a vacuum oven at 150°/150 mm. The dried cream-colorcd salt weighs 130 135 g. (88 92%). 

Fig. 13.144 (1) sulfonation, (2) chromate oxidation to give the naphthalic anhydride (64), (3) condensation with A-methylamine, and (4) replacement of the sulfonic acid group in a reaction with methoxide. This process gives C.I. Fluorescent Brightener 162. 

J. W. Cook introduced the method of cyclizing an o-aroylbenzoic acid to an anthraquinone by heating the keto acid with phosphorus pentoxide in nitrobenzene at 150-165 . For example, the isomeric acids (3) and (4) resulting from the Friedel-Crafts reaction of 1,2-naphthalic anhydride with thiophene are cyclized to the same quinone (5). ... 

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