2-hydroxy-3-naphthoic acid BONA

Hydroxy-3-naphthoic acid ( BONA or BON ) is prepared by heating the sodium salt of 2-hydroxynaphthalene with carbon dioxide in a pressure chamber at 240 to 250°C at a pressure of 15 bar (Kolbe synthesis). The reaction mixture is continuously agitated. Remaining 2-naphthol is separated and recycled ... 

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... 

Pigment Red 52, calcium salt [17852-99-2] 15860 BONA (Ca salt) coupling of dia2oti2ed 2-amino-4-methyl-5-chloroben2enesulfonic acid with 3-hydroxy-2-naphthoic acid, foUowed by salt formation... 

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). 

The history of BONA pigment lakes parallels that of (J-naphthol pigment lakes. Literary evidence of the use of 2-hydroxy-3-naphthoic acid, which was first synthesized in 1887 by Schmitt and Burkard as a coupling component, dates from 1893 (Kostanecki). However, it was not until 1902 that the compound began to be employed in dye synthesis by AGFA (aniline - BONA). 

Diazotization of the aminosulfonic acid and subsequent coupling onto the sodium salt of 2-hydroxy-3-naphthoic acid initially affords the monoazo compound in the form of its soluble sodium salt. Subsequent reaction with chlorides or sulfates of alkaline earth metals or with a manganese salt, frequently in the presence of a dispersion agent, or rosin or its derivatives, at elevated temperature yields the insoluble BONA pigment lake. 

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. 

---