Highly efficient esterification of waxy maize starch in choline chloride/acetic acid acidic deep eutectic solvent system

In this study, to address the issue of solvent selection in the chemical modification of starch, a method was developed for the efficient esterification of waxy maize starch (WMS) using an acidic deep eutectic solvent composed of choline chloride and acetic acid (CCHAc-ADES). The impact of different...

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Veröffentlicht in:Carbohydrate research 2024-11, Vol.548, p.109345, Article 109345
Hauptverfasser: Sun, Kexuan, Yi, Jie, Dai, Rui, Chen, Hui
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Dai, Rui
Chen, Hui
description In this study, to address the issue of solvent selection in the chemical modification of starch, a method was developed for the efficient esterification of waxy maize starch (WMS) using an acidic deep eutectic solvent composed of choline chloride and acetic acid (CCHAc-ADES). The impact of different mass fractions of CCHAc-ADES on the degree of substitution and reaction efficiency of lauric acid starch esters was explored. It was found that under the conditions of 70 wt% CCHAc-ADES, starch esters with the highest degree of substitution of 0.161 were successfully prepared, achieving an esterification efficiency of 79.63 %. 13C and 1H nuclear magnetic resonance spectroscopy, X-ray diffraction and gel permeation chromatography revealed that CCHAc-ADES acted within the surface voids of WMS particles without seriously damaging the WMS structure, making it a favorable solvent for chemical modification of WMS. By monitoring changes in the morphology, relative crystallinity, particle size, and hydrophobicity of esterified WMS in CCHAc-ADES, the formation mechanism of lauric acid starch esters was inferred, primarily related to the competitive hydrogen bonding of CCHAc-ADES with WMS. The method proposed in this study allows for the preparation of long-chain fatty acid starch esters without the use of any additional chemicals or enzymes, offering significant guidance for the application of deep eutectic solvents in green synthesis. [Display omitted] •Discovered a new method for preparing hydrophobic esterified starch using acidic deep eutectic solvents.•The esterification reaction efficiency was optimized, achieving a value of 79.63 %.•The acid deep eutectic solvent can optimally preserve the structure of waxy maize starch.
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The impact of different mass fractions of CCHAc-ADES on the degree of substitution and reaction efficiency of lauric acid starch esters was explored. It was found that under the conditions of 70 wt% CCHAc-ADES, starch esters with the highest degree of substitution of 0.161 were successfully prepared, achieving an esterification efficiency of 79.63 %. 13C and 1H nuclear magnetic resonance spectroscopy, X-ray diffraction and gel permeation chromatography revealed that CCHAc-ADES acted within the surface voids of WMS particles without seriously damaging the WMS structure, making it a favorable solvent for chemical modification of WMS. By monitoring changes in the morphology, relative crystallinity, particle size, and hydrophobicity of esterified WMS in CCHAc-ADES, the formation mechanism of lauric acid starch esters was inferred, primarily related to the competitive hydrogen bonding of CCHAc-ADES with WMS. The method proposed in this study allows for the preparation of long-chain fatty acid starch esters without the use of any additional chemicals or enzymes, offering significant guidance for the application of deep eutectic solvents in green synthesis. [Display omitted] •Discovered a new method for preparing hydrophobic esterified starch using acidic deep eutectic solvents.•The esterification reaction efficiency was optimized, achieving a value of 79.63 %.•The acid deep eutectic solvent can optimally preserve the structure of waxy maize starch.</description><identifier>ISSN: 0008-6215</identifier><identifier>ISSN: 1873-426X</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2024.109345</identifier><identifier>PMID: 39657463</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Esterification modification ; Hydrogen bonding interaction ; Lauric acid ; Low eutectic solvents ; Starch</subject><ispartof>Carbohydrate research, 2024-11, Vol.548, p.109345, Article 109345</ispartof><rights>2024</rights><rights>Copyright © 2024. 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The impact of different mass fractions of CCHAc-ADES on the degree of substitution and reaction efficiency of lauric acid starch esters was explored. It was found that under the conditions of 70 wt% CCHAc-ADES, starch esters with the highest degree of substitution of 0.161 were successfully prepared, achieving an esterification efficiency of 79.63 %. 13C and 1H nuclear magnetic resonance spectroscopy, X-ray diffraction and gel permeation chromatography revealed that CCHAc-ADES acted within the surface voids of WMS particles without seriously damaging the WMS structure, making it a favorable solvent for chemical modification of WMS. By monitoring changes in the morphology, relative crystallinity, particle size, and hydrophobicity of esterified WMS in CCHAc-ADES, the formation mechanism of lauric acid starch esters was inferred, primarily related to the competitive hydrogen bonding of CCHAc-ADES with WMS. The method proposed in this study allows for the preparation of long-chain fatty acid starch esters without the use of any additional chemicals or enzymes, offering significant guidance for the application of deep eutectic solvents in green synthesis. 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The method proposed in this study allows for the preparation of long-chain fatty acid starch esters without the use of any additional chemicals or enzymes, offering significant guidance for the application of deep eutectic solvents in green synthesis. [Display omitted] •Discovered a new method for preparing hydrophobic esterified starch using acidic deep eutectic solvents.•The esterification reaction efficiency was optimized, achieving a value of 79.63 %.•The acid deep eutectic solvent can optimally preserve the structure of waxy maize starch.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>39657463</pmid><doi>10.1016/j.carres.2024.109345</doi></addata></record>
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subjects Esterification modification
Hydrogen bonding interaction
Lauric acid
Low eutectic solvents
Starch
title Highly efficient esterification of waxy maize starch in choline chloride/acetic acid acidic deep eutectic solvent system
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