Putrescine → Trimethylolpropane

HRID 1478783Notes

Reaction equation

HRID 1478783 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][NH2:5].[C:7]([OH:11])(=[O:10])[CH:8]=[CH2:9].[C:12]([OH:16])(=[O:15])[CH:13]=[CH2:14].[C:17]([OH:21])(=[O:20])[CH:18]=[CH2:19].[CH2:22]([C:24]([CH2:29][OH:30])([CH2:27][OH:28])[CH2:25][CH3:26])[OH:23]>CO>[CH2:22]([C:24]([CH2:29][OH:30])([CH2:27][OH:28])[CH2:25][CH3:26])[OH:23].[C:7]([OH:11])(=[O:10])[CH:8]=[CH2:9].[C:12]([OH:16])(=[O:15])[CH:13]=[CH2:14].[C:17]([OH:21])(=[O:20])[CH:18]=[CH2:19].[CH2:22]([C:24]([CH2:29][OH:30])([CH2:27][OH:28])[CH2:25][CH3:26])[OH:23].[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][NH2:5]

Participants

5

Reactant 2

HCID 1045Putrescine2×HCID 250191762-Ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid

Product 2

HCID 6510TrimethylolpropaneHCID 131736527HCID 131736527, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
10 °C

Procedure

52.80 g of 1,4-Butanediamine (BDA) (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 1,4-Butanediamine (BDA) (0.60 mol) and methanol at 110° C. for 8 hours, to yield 56.06 g of light-amber viscous material, i.e., intermediate trimethylolpropane core, amino terminated dendrimer (TMPTA-BDA-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-30b42a55e8544b3a9cc3e16d5acc526a
Source dataset
uspto-grants-2016_08
Patent number
US09403853B2

Reaction notes

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