Self-Thickening Materials Derived from Phenylpropanoid Ene Reactions

In this work, we report the observation of uncatalyzed ene reactions between several phenylpropanoid compounds and diethyl azodicarboxylate (DEAD). For allylbenzene, the reaction produces the ene product at molar ratios of up to 1:2 of allylbenzene to DEAD. At higher levels of DEAD, more complex reactions are observed. For the reaction between methyl eugenol and DEAD, similar ene reaction products have been found. However, the reaction of eugenol with DEAD is more complex; in addition to the ene reaction, other reactions happen at the same time. Most of the structures of the resulting products have been elucidated using NMR spectroscopy (<sup>1</sup>H, <sup>13</sup>C, and 2D), and the findings have been further corroborated by FTIR analysis. Interestingly, these products appear to undergo molecular aggregation, which results in self-thickening in their neat form. However, the viscosity significantly decreases upon dilution with a solvent. This self-thickening property suggests their potential use as thickening agents in organic solvent formulations.

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Publication Details

Journal
Molecules
Published
2025-02-20
DOI
https://doi.org/10.3390/molecules30050977
Primary Topic
Lignin and Wood Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Self-Thickening Materials Derived from Phenylpropanoid Ene Reactions

Roselayne Ferro Furtado, Atanu Biswas, Zengshe Liu, Bret J. Chisholm et al.
Molecules
Lignin and Wood Chemistry
article

Self-Thickening Materials Derived from Phenylpropanoid Ene Reactions

Roselayne Ferro Furtado, Atanu Biswas, Zengshe Liu, Bret J. Chisholm, Omar A. El Seoud, Carlúcio Roberto Alves, Kelton G. Forson, Michael Appell, H. N. Cheng, Karl E. Vermillion, Ryan Beni
article en

Abstract

In this work, we report the observation of uncatalyzed ene reactions between several phenylpropanoid compounds and diethyl azodicarboxylate (DEAD). For allylbenzene, the reaction produces the ene product at molar ratios of up to 1:2 of allylbenzene to DEAD. At higher levels of DEAD, more complex reactions are observed. For the reaction between methyl eugenol and DEAD, similar ene reaction products have been found. However, the reaction of eugenol with DEAD is more complex; in addition to the ene reaction, other reactions happen at the same time. Most of the structures of the resulting products have been elucidated using NMR spectroscopy (<sup>1</sup>H, <sup>13</sup>C, and 2D), and the findings have been further corroborated by FTIR analysis. Interestingly, these products appear to undergo molecular aggregation, which results in self-thickening in their neat form. However, the viscosity significantly decreases upon dilution with a solvent. This self-thickening property suggests their potential use as thickening agents in organic solvent formulations.

MoleculesVol. 30(5)
Universidade Estadual do Ceará (BR), Agricultural Research Service (US), Universidade de São Paulo (BR), National Center for Agricultural Utilization Research (US), Brazilian Agricultural Research Corporation (BR), Southern Regional Research Center (US), Tennessee State University (US)
U.S. Department of Agriculture, Agricultural Research Service
Openalex Percentile: Top 97%
Lignin and Wood Chemistry
DOIOpen Access PDFOpenAlex
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