Chemical Properties
Dark green powder. 1-Aminonaphthalene-8-sulfonic acid [82- 75-7]. (8-aminonaphthalene-1-sulfonic acid), Peri acid, C10H9NO3S, Mr 223.24, crystallizes as the monohydrate and is sparingly soluble even in boiling water. The sodium salt is also sparingly soluble in water. Caustic fusion at 200℃ produces 8-amino-1- naphthol, whereas slow hydrolysis with 10 % sodium hydroxide at 220 – 260℃ yields 1,8- dihydroxynaphthalene. Sulfonation with cold 10 % oleum produces 1-aminonaphthalene-4,8- disulfonic acid, whereas hot concentrated sulfuric acid results in slow isomerization into naphthionic acid.
Uses
Intermediate of dyestuff. Dehydration with phosphorus oxychloride yields naphthosultam, and diazotization followed by hydrolysis results in naphthosultone, the intermediate for 1- hydroxynaphthalene-8-sulfonic acid. Diazotization followed by a Sandmeyer cyanide reaction gives 8-cyanonaphthalene-1-sulfonic acid, one of the most industrially important Sandmeyer reaction products because the nitrile forms the lactam, naphthostyril [130-00-7], upon treatment with concentrated alkali at 185℃. Hydrolysis of naphthostyril with dilute alkali yields 8-aminonaphthalene-1-carboxylic acid, which is the key intermediate for production of anthanthrone vat dyes via 1,10 -binaphthyl8,80 -dicarboxylic acid.
Production Methods
Naphthalene is converted to naphthalene-1-sulfonic acid. The crude sulfonation product is diluted with sulfuric acid, and 67.5 % nitric acid is added slowly at 30℃ to give the 5- and 8-nitro derivatives. The products are converted to the readily soluble magnesium salts by addition of a slurry of dolomite. The reaction mixture is neutralized with chalk and filtered hot. The filtrate is run into a suspension of iron powder in boiling water, which is kept slightly acidic with sulfuric acid. When reduction is complete, dissolved iron is precipitated by addition of magnesia, the iron residues are filtered off while hot, and the resulting liquor is acidified to pH 4.5 with sulfuric acid to give 99 % pure Peri acid in 48 % yield. The filtrates are further acidified to precipitate crude Laurent’s acid. This may be purified via its magnesium salt to give a 17 % yield of pure 1,5-isomer.
