Formaldehyde → HCID 20524062, compound

Participants

Reaction Steps

A solution of 25.6 g (0.200 mole) naphthalene in 128 ml. glacial acetic acid, contaning 11.1 ml (0.200 mole) 96% sulfuric acid, was maintained at 116°-120° C. during addition, over 13 minutes, of 16 ml (0.200 mole) 37% formaldehyde solution. After heating and stirring at 111°-116° C. for two hours, the suspension of slightly gummy solids was cooled to room temperature and the reaction contents poured into 500 ml ice-water mixture. The solids were filtered, washed with water, and air dried. The polymer solids were dissolved in 70 ml. tetrahydrofuran and the solution added slowly to 700 ml. methanol with vigorous stirring to re-precipitate the purified polymer. The solids were collected, washed with methanol, and the precipitation procedure from tetrahydrofuran/methanol repeated. The yield of the naphthalene/formaldehyde polymer, showing a softening point of about 145° C., was 25.0 g. The weight average molecular weight, determined by light scattering in chloroform at room temperature, was 2300±100.

Provenance & Evidence