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 rea...
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2025-02-01
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| author | Atanu Biswas Huai N. Cheng Bret Chisholm Ryan Beni Zengshe Liu Karl Vermillion Michael Appell Kelton Forson Omar El Seoud Carlucio R. Alves Roselayne F. Furtado |
| author_facet | Atanu Biswas Huai N. Cheng Bret Chisholm Ryan Beni Zengshe Liu Karl Vermillion Michael Appell Kelton Forson Omar El Seoud Carlucio R. Alves Roselayne F. Furtado |
| author_sort | Atanu Biswas |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-e26f4bf98afe423786800406c74e1ec9 |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-e26f4bf98afe423786800406c74e1ec92025-08-20T02:53:21ZengMDPI AGMolecules1420-30492025-02-0130597710.3390/molecules30050977Self-Thickening Materials Derived from Phenylpropanoid Ene ReactionsAtanu Biswas0Huai N. Cheng1Bret Chisholm2Ryan Beni3Zengshe Liu4Karl Vermillion5Michael Appell6Kelton Forson7Omar El Seoud8Carlucio R. Alves9Roselayne F. Furtado10National Center for Agricultural Utilization Research, USDA Agricultural Research Services, 1815 N. University Street, Peoria, IL 61604, USASouthern Regional Research Center, USDA Agricultural Research Service, 1100 Allen Toussaint Boulevard, New Orleans, LA 70124, USANational Center for Agricultural Utilization Research, USDA Agricultural Research Services, 1815 N. University Street, Peoria, IL 61604, USANational Center for Agricultural Utilization Research, USDA Agricultural Research Services, 1815 N. University Street, Peoria, IL 61604, USANational Center for Agricultural Utilization Research, USDA Agricultural Research Services, 1815 N. University Street, Peoria, IL 61604, USANational Center for Agricultural Utilization Research, USDA Agricultural Research Services, 1815 N. University Street, Peoria, IL 61604, USANational Center for Agricultural Utilization Research, USDA Agricultural Research Services, 1815 N. University Street, Peoria, IL 61604, USANational Center for Agricultural Utilization Research, USDA Agricultural Research Services, 1815 N. University Street, Peoria, IL 61604, USAInstitute of Chemistry, University of São Paulo, São Paulo 05508-000, SP, BrazilChemistry Department, State University of Ceará, Silas Munguba Av. 1.700, Fortaleza 60740-020, CE, BrazilEmbrapa Agroindústria Tropical, Rua Dra. Sara Mesquita 2270, Fortaleza 60511-110, CE, BrazilIn 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.https://www.mdpi.com/1420-3049/30/5/977allylbenzenediethyl azodicarboxylateene reactioneugenolmethyl eugenolphenylpropanoids |
| spellingShingle | Atanu Biswas Huai N. Cheng Bret Chisholm Ryan Beni Zengshe Liu Karl Vermillion Michael Appell Kelton Forson Omar El Seoud Carlucio R. Alves Roselayne F. Furtado Self-Thickening Materials Derived from Phenylpropanoid Ene Reactions Molecules allylbenzene diethyl azodicarboxylate ene reaction eugenol methyl eugenol phenylpropanoids |
| title | Self-Thickening Materials Derived from Phenylpropanoid Ene Reactions |
| title_full | Self-Thickening Materials Derived from Phenylpropanoid Ene Reactions |
| title_fullStr | Self-Thickening Materials Derived from Phenylpropanoid Ene Reactions |
| title_full_unstemmed | Self-Thickening Materials Derived from Phenylpropanoid Ene Reactions |
| title_short | Self-Thickening Materials Derived from Phenylpropanoid Ene Reactions |
| title_sort | self thickening materials derived from phenylpropanoid ene reactions |
| topic | allylbenzene diethyl azodicarboxylate ene reaction eugenol methyl eugenol phenylpropanoids |
| url | https://www.mdpi.com/1420-3049/30/5/977 |
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