2-Naphthoic acids

Naphthoic acids and their halogen, nitrogen and hydroxyl derivatives. (1953.)... 

Naphthoic acids CO in the nucleus oxo-acids, poly-acids. (1954.)... 

Chapter IV. a-Chloromethylnaphthalene (IV,23) benzylamine (Gabriel synthesis) (IV,39) i r.N -dialkylanilines (from amines and trialkyl orthophosphates) (IV,42) a-naphthaldehyde (Sommelet reaction) (IV,120) a-phenyl-cinnamic acid (Perkin reaction using triethylamine) (IV,124) p-nitrostyrene (IV,129) p-bromonaphthalene and p naphthoic acid (from 2 naphthylamine-1 -sulphonic acid) (IV,62 and IV,164) diphenic acid (from phenanthrene) (IV,165). 

Benzoic acid and naphthoic acid are formed by the oxidative carbonylation by use of Pd(OAc)2 in AcOH. t-Bu02H and allyl chloride are used as reoxidants. Addition of phenanthroline gives a favorable effect[360], Furan and thiophene are also carbonylated selectively at the 2-position[361,362]. fndole-3-carboxylic acid is prepared by the carboxylation of 1-acetylindole using Pd(OAc)2 and peroxodisulfate (Na2S208)[362aj. Benzoic acid derivatives are obtained by the reaction of benzene derivatives with sodium palladium mal-onate in refluxing AcOH[363]. 

Hydroxy-2-naphthoic acid. (See also Beta-hydroxynaphthoic acid). 

Poly(d-hydroxy-2-naphthoic acid-co-4-hydroxybenzoic acid) [81843-52-9]... 

In the late 1980s, new fully aromatic polyester fibers were iatroduced for use ia composites and stmctural materials (18,19). In general, these materials are thermotropic Hquid crystal polymers that are melt-processible to give fibers with tensile properties and temperature resistance considerably higher than conventional polyester textile fibers. Vectran (Hoechst-Celanese and Kuraray) is a thermotropic Hquid crystal aromatic copolyester fiber composed of -hydroxyben2oic acid [99-96-7] and 6-hydroxy-2-naphthoic acid. Other fully aromatic polyester fiber composites have been iatroduced under various tradenames (19). 

Industrial Thermotropic LGPs. Vectran, poly(6-hydroxy-2-naphthoic acid- o-4-hydroxybenzoic acid) [81843-52-9] is currendy the only thermotropic fiber which is commercially available (13). Vectran is synthesized by the melt acidolysis of/ -acetoxybenzoic acid and 6-acetoxy-2-naphthoic acid. 

First,/)-hydroxybenzoic acid (HBA) and 6-hydroxy-2-naphthoic acid (HNA) are acetylated to produce the low melting acetate esters which are molten at 200°C. In an inert gas, the two monomers are melted together at 200°C. The temperature is raised to 250—280°C and acetic acid is coUected for 0.5 to 3 h. The temperature is raised to 280—340°C and additional acetic acid is removed in vacuum for a period of 10 to 60 min. The opalescent polymer melt produced is extmded through a spinning jet, foUowed by melt drawdown. The use of the paraUel offset monomer, acetylated HNA, results in the formation of a series of random copolyesters of different compositions, many of which faU within the commercially acceptable melting range of... 

Naphthalenol also is used ia the preparation of azo, iadigoid, and nitro, eg, 2,4-dinitro-l-naphthol, dyes, and ia making dye iatermediates, eg, naphtholsulfonic acids, 4-chloro-1-naphthalenol, and l-hydroxy-2-naphthoic acid. 1-Naphthalenol is an antioxidant for gasoline, and some of its alkylated derivatives are stabilizers for plastics and mbber (68). 

Tetrahydro2oline [84-22-0] 2-(l,2,3,4-tetrahydro-l-naphthyl)2-imida2olin, (Tysine, Visine) (40), a sympathomimetic and nasal decongestant, is made by the condensation of 1,2,3,4-tetrahydro-l-naphthoic acid or its methyl ester with 1,2-ethylenediamine. 

Hydroxy-1-Naphthalenecarboxylic Acid. 2-Hydroxy-1-naphthoic acid is manufactured by a Kolbe-type process, ie, by reaction of the thoroughly dried potassium or sodium 2-naphthalenolate with CO2 at ca 115—130°C in an autoclave at ca 300—460 kPa (3.0—4.5 atm) for 10—16 h. It decarboxylates readily, eg, in water starting at ca 50°C. 

Hydroxy-2-Naphthalenecarboxylic Acid. l-Hydroxy-2-naphthoic acid is made similarly to the isomer (2-hydroxy-1-naphthoic acid) by reaction of dry sodium 1-naphthalenolate with CO2 in an autoclave at ca 125°C. It has been used in making triphenylmethane dyes and metalli able a2o dyes. Alkylamides and arylamides of l-hydroxy-2-naphthalenecarboxyhc acid are cyan couplers, ie, components used in indoaniline dye formation in color films (see Color PHOTOGRAPHY). 

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