Formaldehyde → Hydroxymethyl Oxazolidine Iodopropynyl Butylcarbamate

Participants

Reaction Conditions

Reaction Steps

A closed vessel is charged with 102 g of 1,3-dihydroxybutane and 62 g of prilled paraformaldehyde is added and mixed at room temperature until a uniform slurry is formed. The slurry is then heated to 60° C. and a 2% molar (or 1–5%) molar excess of tris(hydroxymethyl)aminomethane (THAM) is introduced. A total of 124 g of 99% pure tris(hydroxymethyl)aminomethane is gradually added in increasing increments until a 2% molar excess is obtained. The ensuing condensation reaction takes place over a period of 3 hours. During the reaction, soluble bicyclic hydroxymethyl oxazolidine is continuously formed. Since paraformaldehyde and tris(hydroxymethyl)-aminomethane are of low solubility in the reaction medium, completion of the reaction is indicated when a clear solution is formed with water by-product. When the mixture becomes clear, insuring that all of the formaldehyde has reacted, the resulting solution is allowed to cool to ambient temperature and 4.42 g of powdered IPBC (weight ratio of bicyclic hydroxymethyl oxazolidine HMBO to IPBC is 33:1) is added and stirred until a clear solution is obtained. No crystallization of IPBC is noted in the substantially colorless product and a pure clear, liquid composition containing less than 1000 ppm of formaldehyde is obtained.

Provenance & Evidence