Ethylenediamine → Trimethylolpropane

HRID 1478781Notes

Reaction equation

HRID 1478781 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[C:5]([OH:9])(=[O:8])[CH:6]=[CH2:7].[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].[C:15]([OH:19])(=[O:18])[CH:16]=[CH2:17].[CH2:20]([C:22]([CH2:27][OH:28])([CH2:25][OH:26])[CH2:23][CH3:24])[OH:21]>CO>[CH2:20]([C:22]([CH2:27][OH:28])([CH2:25][OH:26])[CH2:23][CH3:24])[OH:21].[C:5]([OH:9])(=[O:8])[CH:6]=[CH2:7].[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].[C:15]([OH:19])(=[O:18])[CH:16]=[CH2:17].[CH2:20]([C:22]([CH2:27][OH:28])([CH2:25][OH:26])[CH2:23][CH3:24])[OH:21].[CH2:1]([NH2:4])[CH2:2][NH2:3]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 250191762-Ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid

Product 2

HCID 6510TrimethylolpropaneHCID 131736526HCID 131736526, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

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).

Workup

  1. customto react at 25° C. for 24 hours
  2. distillationThe result solution is subjected to vacuum distillation
  3. customto remove excess ethylenediamine (EDA) and methanol at 80° C. for 5 hours

Sources & evidence

ORD record
ord-59f2b04217064777b8656bda265febec
Source dataset
uspto-grants-2016_08
Patent number
US09403853B2

Reaction notes

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