Ethylenediamine → Trimethylolpropane

Participants

Reaction Conditions

Reaction Steps

36.00 g of ethylenediamine (EDA) (0.60 mol) was added into a round-bottom flask with a stirring, a reflux condenser and a thermometer, and cooled to 10° C. below under nitrogen. 74.00 g of methanol solution of trimethylolpropane triacrylate (TMPTA) (40%, 0.1 mol) was added to the round-bottom flask, and the mixture is allowed to react at 25° C. for 24 hours. The result solution is subjected to vacuum distillation to remove excess ethylenediamine (EDA) and methanol at 80° C. for 5 hours, to yield 47.61 g of light-amber viscous material, i.e., intermediate trimethylolpropane core, amino terminated dendrimer (TMPTA-EDA-9NH for abbreviation). 37.52 g of phosphorous acid (99.0%, 0.453 mol) and 54.26 g of concentrated hydrochloric acid (37%, 0.550 mol) were respectively placed and uniformly mixed in a four-necked flask equipped with a condenser, a stirring, a thermometer and a dropping funnel. Next, 47.60 g (50%, 0.05 mol) aqueous solution of the intermediate trimethylolpropane core, amino terminated dendrimer (TMPTA-EDA-9NH) was slowly added to above mixture solution with cooling and stirring in such a rate to maintain temperature below 40° C. The resulting mixture was heated up to 85° C., and 44.60 g of formaldehyde solution (37%, 0.550 mol) was then added to the mixture with stirring to form a reaction mixture. The temperature of the reaction mixture maintained at 90° C. for 1 hour, and then was elevated to 103° C. for a reflux period of 4 hours. After the reflux, reaction mixture was concentrated at 103° C. for 1 hour, and meanwhile, hydrochloric acid was removed off with HCl absorption bottle. Next, the reaction mixture was cooled to ambient temperature, to give an amber transparent liquid product with 38.90% solid content by weight, i.e., the trimethylolpropane core, phosphonic acid terminated dendrimer (TMPTA-EDA-9PO3H2).

Provenance & Evidence