Nucleophilic ring opening of 2-oxazolines with amines: a convenient synthesis for unsymmetrically substituted ethylenediamines

Fazio, Michael

doi:10.1021/jo00199a029

Cited by 40 publications

(25 citation statements)

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“…Moreover, Lepaumier et al (2009a) showed that HEIA was the major degradation product and was very stable. These results are in accordance with Fazio (1984) who described diamine syntheses with oxazolidin-2-ones as starting materials.…”

Section: Thermal Degradationsupporting

confidence: 93%

Amine degradation in CO2 capture. I. A review

Gouedard

Picq

Launay

et al. 2012

International Journal of Greenhouse Gas Control

442

321

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Section: Thermal Degradationsupporting

confidence: 93%

Amine degradation in CO2 capture. I. A review

Gouedard

Picq

Launay

et al. 2012

International Journal of Greenhouse Gas Control

442

321

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“…The presence of such amine impurities is detrimental for thermal curing polymerizations with 2-oxazolines as they are known to negatively affect the reactivity of the mixture. 61 Additionally, the presence of unreacted itaconic acid or amines will affect the stoichiometry and might hamper build-up of molecular weight. For this purpose, we have slightly modified the synthesis and purification methods provided in the literature: 11 , 15 First the synthesis is performed in bulk at 130–180 °C in the presence of a catalytic amount of water.…”

Section: Resultsmentioning

confidence: 99%

Renewable (Bis)pyrrolidone Based Monomers as Components for Thermally Curable and Enzymatically Depolymerizable 2-Oxazoline Thermoset Resins

Roy

Noordzij

Boomen

et al. 2018

ACS Sustainable Chem. Eng.

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In this study we describe the synthesis of bis(pyrrolidone) based dicarboxylic acids from itaconic acid and their application in 2-oxazoline resins for fully renewable thermoset materials. The monomers are obtained using a bulk aza-Michael addition of a diamine and two itaconic acid molecules using a catalytic amount of water. The monomers can be isolated in high purity after recrystallization, though their yield proved to be highly dependent on the selected diamine spacer length: In general, only the dicarboxylic acids containing diamines with an even number of methylene spacers are isolated in high yields. Through NMR, GPC, and FTIR analysis we demonstrate that these bis(pyrrolidone) based dicarboxylic acids exhibit significantly enhanced curing rates in 2-oxazoline resins compared to resins containing aliphatic dicarboxylic acids such as sebacic acid. Overall, we demonstrate that the rate of 2-oxazoline ring-opening addition with carboxylic acid functionalities is determined by the used dicarboxylic acid, whereas the ring-opening addition of the 2-oxazoline functionality with amide groups is determined by the used bis(2-oxazoline) compound. The thermosets obtained after curing proved to be readily plasticized by water, opening up possibilities for enzymatic degradation.

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“…In the latter case it was suggested that a stable aziridinium compound 208 formed, which would not react easily with acetonitrile because of steric congestion. The opening of 2-oxazolines [103] or of serine-derived blactones [104] by amines has also been used to prepare 1,2-diamine derivatives.…”

Section: Vicinal Diamines From B-amino Alcoholsmentioning

confidence: 99%