OXYNAPHTHOATE

Hydroxy-2-Naphthalcnccarboxylic Acid. 3-Hydroxy-2-naphthoic acid or p-oxynaphthoic acid (BON BONA Developer 8) (28) is the principal commercial product among the hydroxynaphthalenecarboxyUc acids. To produce BON, 2-naphthol is first transformed into sodium... 

This carboxylation reaction is of importance mainly for the manufacture from 2-naphthol of P-oxynaphthoic acid (BON) acid, the parent acid of sodium 3-hydroxy-2-naphthoate (4-35). The carboxylation is achieved by heating the sodium salt of 2-naphthol under pressure in an atmosphere of carbon dioxide (Scheme 4.25). Under these conditions an equilibrium mixture of the naphthol and its carboxylated derivative is established, the mixture containing about 30% of the carboxylic acid. The desired product is extracted from the reaction mixture and the unchanged 2-naphthol is recycled. 

In 1892, the chemist Schopf, in an attempt to prepare 2-phenylamino-3-naph-thoic acid, developed a synthetic route leading to the anilide of 2-hydroxy-3-naph-thoic acid. His method continues to be used today, if only in a slightly modified form. He added phosphorus trichloride to a molten reaction mixture containing aniline and 2-hydroxy-3-naphthoic acid (beta-oxynaphthoic acid, also known as BONA) and received Naphthol AS in good yield. Modern processes differ from this principle only in terms of reaction control the synthesis is now carried out in the presence of organic solvents, such as aromatic hydrocarbons. 

These pigments derive their name from 2-hydroxy-3-naphthoic acid, which is used as a general coupling component for the entire group. The compound is also known as beta-oxynaphthoic acid (BONA). 

Carboxylation. The introduction of carboxyl groups into the structures of phenols and naph-thols produces some important dye intermediates, including salicylic acid and (3-oxynaphthoic acid (BON acid). This process is conducted under pressure at elevated temperatures using the sodium salts of phenols/naphthols and in the case of (3-naphthol, the carboxyl group enters... 

Naphthylthiourea Adenosine triphosphate Bovine 7-globulin Butylated nydroxyanisole Benzene hexachloride /3-Methylumbelliferone /3-Oxynaphthoic acid... 

These compounds are also useful in wool-dyeing. The dyeing process is simple, as owing to the stability of these compounds the mordanting with bichromate and the dyeing may be effected in one bath. -oxynaphthoic acid combines with nitrodiazo-compounds, producing brown dyestuffs which possess the property, like the above, of dyeing on mordants. 

Both 2-naphthol (35) and its derivative B-, or 2-oxynaphthoic acid are important coupling components in the production of azo pigments. The latter is used for several reds,... 

Beilstein Handbook Reference) AI3-00894 B.o.n. acid BON BON acid BONA BRN 0744100 Cl Developer 8 Cl Developer 20 CCRIS 2298 Developer 8 Developer BON EINECS 202-180-8 HSDB 5278 2-Hydroxy-3-naphthalenecarboxylic acid 2-Hydroxy-3-naphthoic acid Kyselina 3-hydroxy-2-naftoova Miketazol Developer ONS p-Naphthoic acid, 3-hydroxy- Naphthol B.O.N. Naphthol bon NSC 3719 p-Oxynaphthoic acid. Needles mp = 222.5 Xm = 235, 284 nm (MeOH) slightly soluble in H2O, readily soluble in EtOH, Et20, CeHe, CHCI3, CrH8. 

Alpha-oxynaphthoic acid 91/0 wt%) [4] Combination of boric acid and phenol [4]... 

A typical example is the Kolbe-Schmitt carbonation of the sodium salt of / -naphthol in an inert liquid medium in the production of /3-oxynaphthoic acid (commonly known as BON acid), a useful intermediate in the manufacture of dyes and other chemicals. Chlorination of wood pulp suspended in water is another example. 

Oxynaphthoic acid (BON acid), a useful organic intermediate used mainly in the manufacture of dyes, is produced by the Kolhe-Scimitt carbonation of sodium naphthenate prepared by reacting naphthalene with sodium hydroxide. The carbonation step is normally carried out in a dry atmosphere, but the possibility of conducting the reaction in a liquid medium such as kerosene has also been explored. The reaction scheme may be represented as... 

Piezoelectric can be produced Ifom liquid-crystal polymers based on -oxybenzoic acid/polyethyleneterephthalate and -oxybenzoic acid/ oxynaphthoic acid. Time-stability and temperature range of efficiency of piezoelectric from polymer made of 6,2-oxynaphthoic acid are higher compared to that of polyethyleneterephthalate. 

Results are presented of an investigation of the use of linear-temp, controlled pyrolysis with subsequent analysis of the pyrolysates (volatiles and residues) by 18V electron-impact mass spectrometry and FTIR spectrometry to provide information on the thermal degradation mechanisms of aromatic polyesters, in particular polyhydroxybenzoic acid and oxybenzoate-oxynaphthoate copolymer (Vectra). 13 refs. 

Early studies of the thermal degradation of so-called polyarylates were covered by Neiman [100] and Ehlers and co-workers [101]. Since then, several highly aromatic and specifically liquid crystalline (mesogenic) polyesters have been examined in terms of their anaerobic thermal degradation characteristics. These inclnde homopolymers of hydroxybenzoic acids [102-105] copolymers of hydroxybenzoic acid with hydroxynaphthoic acid [105-108] polymers which are essentially copolymers of hydroxybenzoic acid and alkyene terephthalates [107-118] copolymers of hydroxybenzoic acid with other aromatic polyesters [119-122] phenolic and bisphenolic terephthalates [123-127] poly(oxynaphthoate)s [128] and liquid crystal polyesters (LCP) containing unsaturated acids as part of a copolyester chain [129-131]. 

Poly(oxybenzoate-co-oxynaphthoate). Figure 2.64 represents an even more complicated polymer system. In this case the macromolecule is the random copolymer poly(oxybenzoate-co-oxynaphthoate), a high-strength material (Vectra ). 

In this section, copolymers of polyethylene are discussed, starting with low-density, branched polyethylene and culminating with crystallization, melting, and annealing of poly(ethylene-co-octene-l), also described as linear-low-density polyethylene, LLDPE. Furthermore, partial phase diagrams of poly(ethylene terephthalate-co-oxybenzoate), PETcoOB, andpoly(oxybenzoate-co-oxynaphthoate), POBcoON, are presented. The latter systems are examples of increasing chain stiffness by cocrystalUzation which leads to mesophase behavior (see Sect. 5.5). 

PETcoOB and POBcoON. A second example of thermal analysis of copolymers involves the two systems, poly(ethylene terephthalate-co-oxybenzoate), PETcoOB, and poly(oxybenzoate-co-oxynaphthoate), POBcoON. The structural formulas of the CRUs are as follows ... 

Of special importance is in this case that the backbone of the copolymer can change chemically by trans-esterification (see Fig. 3.47). In fact, heating poly(ethylene terephthalate) and acetoxybenzoic acid in the melt is a common synthetic route to PETcoOB. The inclusion of oxybenzoate groups makes poly(ethylene terephthalate) increasingly stiffer (see Fig. 1.50). In POBcoON, oxynaphthoate adds an additional off-set of the large zig-zag of the benzoate. As a result of this chain stiffening, the PETcoOB with more than 30 mol-% oxybenzoate shows an anisotropic melt, as for a nematic main-chain liquid crystal (see Fig. 5.136) and the system POBcoON has a mesophase character over the whole concentration range. 

POB, see poly(4-hydroxybenzoic acid), as well as polyoxybenzoate POBcoON, see poly(oxybenzoate-co-oxynaphthoate)... 

X.-G. Li and M.-R. Huang, Thermal decomposition kinetics of thermotr( icpoly(oxybenzoate-co-oxynaphthoate) vectra copolyester. Polymer Degradation and Stability, 64, 81 (1999). 

The thermotropic liquid-crystal copolyesters can be synthesized also on the basis of -oxybenzoic and 2, 6-oxynaphthoic acid at presence of catalysts (sodium and calcium acetates) [69, 70], The catalyst sodium acetate accelerates the process of synthesis. Calcium acetate accelerates the process only at high concentration of the catalyst and influences on the morphology of complex copolyesters. 

Claret red n. Azo pigment produced by coupling Tobias acid (2-naphthylamine-l-sulfonic acid) with 3-oxynaphthoic acid, followed by conversion to the calcium lake. 

Hydroxy-2-naphthoic Acid (2 i-Hydr-oxynaphthoic acid, -hydroxynaphthoic acid, 3-oxynaphthoic acid, 2-naphthol-i-carboxylic acid). 

In a series of investigations on polymers carrying chemically-bound chromo-phores, oxyethylenes, and oligo(oxyethylene-co-oxypropylene)s with hydroxyl end groups were modified by nitration and amination. The amino end groups were then diazotized and coupled with /8-oxynaphthoic acid and AA -diethylaniline. From the... 

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