1.5- Naphthalic acid

WATER-INSOLUBLE NAPHTHALIC ACID IMIDE DYESTUFFS... 

Water-insoluble naphthalic acid imide dyestuffs of the... 

New water-insol. naphthalic acid imide dyestuffs - used to dye blends of polyamide or urethane- and polyester or tri acetate fibres having good light and washing fastness C91-110.342 RICH DE GB LI) ... 

A waler-insol. naphthalic acid imide dyestuff of formula (I) is new ... 

Naphthalic acid (naphthalene-1,8-dicarboxylic acid) [518-05-8] M 216.9, m 270°, PKeu(I) 2.1, pKEst(2) 4.5. Crystd from EtOH or aq EtOH. 

The oxidation of naphthalic acid (1,8-naphthalenedicarboxylic acid) by peroxide, rather surprisingly, does not proceed by formation of a cyclic peroxide but rather via a dioxirane [53] (a three-membered ring containing a carbon atom and a peroxide group). CL is observed from this reaction. 

The primary starting material for the synthesis of perylene tetracarboxylic acid pigments is the dianhydride 71. It is prepared by fusing 1,8-naphthalene dicar-boxylic acid imide (naphthalic acid imide 69) with caustic alkali, for instance in sodium hydroxide/potassium hydroxide/sodium acetate at 190 to 220°C, followed by air oxidation of the molten reaction mixture or of the aqueous hydrolysate. The reaction initially affords the bisimide (peryldiimide) 70, which is subsequently hydrolyzed with concentrated sulfuric acid at 220°C to form the dianhydride ... 

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 ... 

A different route proceeds by alkali fusion of the corrspondingly substituted naphthalic acid imide. This pathway parallels the synthesis of perylene tetracarboxylic acid diimide 70 (Sec. 3.4.1.1). The method is particularly suited to aliphatic amines. 

Uses Manufacture of dye intermediates, fluorescent dyes, pharmaceuticals, photographic chemicals, insecticides, fungicides, plastics, and 1,8-naphthalic acid chemical research. Derived from coal tar and petroleum refining. 

Dimethylnaphthalene 175 2,6-Naphthalic acid, 20 6-Methyl-2-naphthoic acid, 10... 

Although most of the experiments were carried out using p-xylene as substrate, several exploratory runs were made using other aromatic hydrocarbons. These are summarized in Table I. Maximum yields were not determined. Alkylnaphthalenes gave highly colored oxidates, from which only small amounts of naphthoic and naphthalic acids could be isolated. Oxidation of anthracene gave virtually quantitative yields of anthraquinone under extremely mild conditions (10). 

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). 

The reaction of barbiturate and 1,3 -dimethylbarbiturate ions with 2- and 4-nitrobenzaldehyde and 2,4-dinitrobenzaldehyde represented generally in Scheme 5 involves a diffusion-controlled (viscosity effects on rates) proton transfer from hydronium ion to an addition intermediate T in the slow step.14 The addition of water and ring-opening reactions of the protonated benzoxazines (14) involves the cyclic intermediate (15). At low buffer concentrations buffer-catalysed collapse of the intermediate is rate limiting but, at high buffer concentrations, the addition of water is the rate-limiting step.15 The anionic tetrahedral intermediate (16) is involved in the hydrolysis of the 2, 2, 2,-trifluoroethyl monoester of 1,8-naphthalic acid (17).16... 

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. 

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. 

Isocaffeine l//-Purine-2,6-dione,3,9-dihydro-l,3,9-trimethyl- Naphthalic acid 1,8-Naphthalenedicarboxylic acid... 

By fusion of naphthalene sulphonic acids with potassium cyanide the corresponding cyano naphthalenes are obtained. These compounds are nitriles of naphthalene acids. The mono-carboxyl acids are known as naphthoic acids while the di-carboxyl acids are termed naphthalic acids. The naphthoic acids are similar to benzoic acid and the naphthalic acids are like the phthalic acids. The naphthalic acid... 

The presence of benzoic acid or of diphenic acid, formed in the wet oxidation of plienanthraquinone, has not been reported in the products of phenanthrene oxidation in the vapor phase. A naphthalic acid has been found and the presence of quinones established in the products.11, b Mechanism for this oxidation cannot be postulated because of the present lack of data. 

HBA/HNA, copolyester of 4-hydroxybenoic acid and 6-hydroxy-2-naphthalic acid. 

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