Glutaric Acid → HCID 22335829, compound

HRID 586646Notes

Reaction equation

HRID 586646 reaction equation
[C:1]([OH:9])(=[O:8])[CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:10]([O:14][CH2:15][CH2:16][O:17][CH:18]=[CH2:19])[CH:11]1[O:13][CH2:12]1>>[CH2:10]([O:14][CH2:15][CH2:16][O:17][CH:18]([O:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][C:1]([O:9][CH:18]([O:17][CH2:16][CH2:15][O:14][CH2:10][CH:11]1[O:13][CH2:12]1)[CH3:19])=[O:8])[CH3:19])[CH:11]1[O:13][CH2:12]1

Participants

3

Reactant 2

HCID 743Glutaric AcidHCID 2047352-{[2-(Ethenyloxy)ethoxy]methyl}oxirane

Product 1

HCID 22335829HCID 22335829, compound

Procedure

Glutaric acid (1.32 g; 0.01 moles) was added slowly over about 20 minutes to a stirred reaction flask containing 2-vinyloxyethyl glycidyl ether (prepared as described by Sawamoto et. Al in J. Polym. Sci., Part A 1987, V. 25, 2717) at 80° C. After all the acid was added, heating and stirring was continued for a further 2 hours. On cooling, the product, bis-[α-(2-glycidoxyethoxy)ethyl]glutarate, was obtained in quantitative yield. The structure of the product was confirmed by 1H NMR and IR analysis. Previous synthesis of polyepoxides by addition of 2-vinyloxyethyl glycidyl ether to polycarboxylic acids has previously been reported to occur in the presence of acid catalysts by Tofimov et. al (Review Heteroatom Chem. 1993, V.9, 205). Such catalysts are undesirable as they tend to reduce the storage stability of the epoxide monomer and reduce the degradation temperature of the cured adhesive polymer.

Workup

  1. additionAfter all the acid was added
  2. temperatureheating
  3. temperatureOn cooling

Sources & evidence

ORD record
ord-969bc0d246f14f14877f93f784814c13
Source dataset
uspto-grants-2005_08
Patent number
US06936664B2

Reaction notes

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