Hexamethylenediamine → Trimethylolpropane

HRID 1478784Notes

Reaction equation

HRID 1478784 reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[C:9]([OH:13])(=[O:12])[CH:10]=[CH2:11].[C:14]([OH:18])(=[O:17])[CH:15]=[CH2:16].[C:19]([OH:23])(=[O:22])[CH:20]=[CH2:21].[CH2:24]([C:26]([CH2:31][OH:32])([CH2:29][OH:30])[CH2:27][CH3:28])[OH:25]>CO>[CH2:24]([C:26]([CH2:31][OH:32])([CH2:29][OH:30])[CH2:27][CH3:28])[OH:25].[C:9]([OH:13])(=[O:12])[CH:10]=[CH2:11].[C:14]([OH:18])(=[O:17])[CH:15]=[CH2:16].[C:19]([OH:23])(=[O:22])[CH:20]=[CH2:21].[CH2:24]([C:26]([CH2:31][OH:32])([CH2:29][OH:30])[CH2:27][CH3:28])[OH:25].[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

5

Reactant 2

HCID 16402Hexamethylenediamine2×HCID 250191762-Ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid

Product 2

HCID 6510TrimethylolpropaneHCID 131736528HCID 131736528, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
10 °C

Procedure

69.60 g of 1,6-Hexanediamine (HDA) (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 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 1,6-Hexanediamine (HDA) (0.60 mol) and methanol at 110° C. for 8 hours, to yield 64.46 g of light-amber viscous material, i.e., intermediate trimethylolpropane core, amino terminated dendrimer (TMPTA-HDA-9NH for abbreviation).

Workup

  1. customto react at 25° C. for 24 hours
  2. distillationThe result solution is subjected to vacuum distillation

Sources & evidence

ORD record
ord-d50fc7f5a02d410f82ba21d0fb83f4c6
Source dataset
uspto-grants-2016_08
Patent number
US09403853B2

Reaction notes

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