Dataset Information

Synthesis of Benzoxazoles, Benzimidazoles, and Benzothiazoles Using a Bronsted Acidic Ionic Liquid Gel as an Efficient Heterogeneous Catalyst under a Solvent-Free Condition.

ABSTRACT: Herein, we introduce a reusable Brønsted acidic ionic liquid gel (BAIL gel) obtained by treating 1-methyl-3-(4-sulfobutyl)-1H-imidazolium hydrogen sulfate with tetraethyl orthosilicate (TEOS). The grafting of the Brønsted acidic ionic liquid to the surface of TEOS has increased the catalytic activity of the material and also simplified catalyst recovery from the reaction mixture. This reaction has a wide substrate scope, and the BAIL gel represents a new catalyst for the synthesis of benzoxazoles, benzimidazoles, and benzothiazoles. The method shows attractive characteristics such as high yields, recyclable catalyst, and work-up simplicity. More importantly, no additional additives or volatile organic solvent and inert atmosphere are required for the reaction, and the BAIL gel has shown a great promise for industrial applications. To the best of our knowledge, the synthesis of benzoxazoles, benzimidazoles, and benzothiazoles using a recyclable heterogeneous ionic liquid gel was not previously reported in the literature.

SUBMITTER: Nguyen TT

PROVIDER: S-EPMC6648500 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Synthesis of Benzoxazoles, Benzimidazoles, and Benzothiazoles Using a Brønsted Acidic Ionic Liquid Gel as an Efficient Heterogeneous Catalyst under a Solvent-Free Condition.

Nguyen The Thai TT Nguyen Xuan-Trang Thi XT Nguyen Thuy-Linh Ho TH Tran Phuong Hoang PH

ACS omega 20190107 1

Herein, we introduce a reusable Brønsted acidic ionic liquid gel (BAIL gel) obtained by treating 1-methyl-3-(4-sulfobutyl)-1<i>H</i>-imidazolium hydrogen sulfate with tetraethyl orthosilicate (TEOS). The grafting of the Brønsted acidic ionic liquid to the surface of TEOS has increased the catalytic activity of the material and also simplified catalyst recovery from the reaction mixture. This reaction has a wide substrate scope, and the BAIL gel represents a new catalyst for the synthesis of benz ...[more]

PMID: 31459336

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Project description:Lignin can be considered an essential under-exploited polymer from lignocellulosic biomass representing a key for a profitable biorefinery. One method of lignin valorization could be the improvement of physico-chemical properties by esterification to enhance miscibility in apolar polyolefin matrices, thereby helping the production of bio-based composites. The present work describes for the first time a succeeded chemical esterification of industrial lignins with maleic anhydride in an acidic ionic liquid: 1-butyl-3-methyl imidazolium hydrogen sulfate without additional catalyst. This efficient strategy was applied to four industrial lignins: two softwood Kraft lignins (Indulin AT, Wayagamack), one hardwood Kraft lignin (Windsor), and one softwood organosolv lignin (Lignol), distinct in origin, extraction process and thus chemical structure. The chemical, structural, and thermal properties of modified lignins were characterized by 31P nuclear magnetic resonance, infrared spectroscopy and thermal analyses, then compared to those of unmodified lignins. After 4 h of reaction, between 30 to 52% of the constitutive hydroxyls were esterified depending on the type of lignin sample. The regioselectivity of the reaction was demonstrated to be preferentially orientated toward aliphatic hydroxyls for three out of four lignins (66.6, 65.5, and 83.6% for Indulin AT, Windsor and Lignol, respectively, vs. 51.7% for Wayagamack). The origin and the extraction process of the polymer would thus influence the efficiency and the regioselectivity of this reaction. Finally, we demonstrated that the covalent grafting of maleyl chain on lignins did not significantly affect thermal stability and increased significantly the solubility in polar and protic solvent probably due to additional exposed carboxylic groups resulted from mono-acylation independently of H/G/S ratio. Blending with polyolefins could then be considered in regard of compatibility with the obtained physico-chemical properties.

Dataset Information

Synthesis of Benzoxazoles, Benzimidazoles, and Benzothiazoles Using a Bronsted Acidic Ionic Liquid Gel as an Efficient Heterogeneous Catalyst under a Solvent-Free Condition.

Publications

Synthesis of Benzoxazoles, Benzimidazoles, and Benzothiazoles Using a Brønsted Acidic Ionic Liquid Gel as an Efficient Heterogeneous Catalyst under a Solvent-Free Condition.

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