Green synthesis of acetylated maize starch in different imidazolium carboxylate and choline carboxylate ionic liquids

Fei Ren; Jinwei Wang; Jinglin Yu; Cheng Zhong; Fengwei Xie; Shujun Wang

doi:10.1016/j.carbpol.2022.119353

Green synthesis of acetylated maize starch in different imidazolium carboxylate and choline carboxylate ionic liquids

Fei Ren, Jinwei Wang, Jinglin Yu, Cheng Zhong, Fengwei Xie, Shujun Wang

Research output: Contribution to journal › Article › peer-review

18 Citations (SciVal)

Abstract

This work demonstrates that acetylated maize starches (AMS) with varied degree of substitution (DS, 0.26–2.63) was synthesized in ionic liquids (ILs) (imidazolium chloride, imidazolium carboxylate and choline carboxylate) at 85 °C without catalyst. The DS of AMS and reaction efficiency increased with decreasing alkyl chain length of cations or anions, while decreased as the choline cation replaced the imidazolium cation and the chloride anion replaced the acetate anion. The AMS synthesized in imidazolium-based ILs exhibited much higher hydrophobicity and thermal stability than the native starch. Rheological properties of ILs and ATR-FTIR analysis of acetic anhydride/ILs mixtures indicated that a shorter alkyl side chain or the combination of an imidazolium cation and an acetate anion gave ILs lower viscosities and weaker interactions between acetic anhydride molecules, which favored the acetylation of starch. These findings provide insights into the design of green processes to modify starch and the application of acetylated starch.

Original language	English
Article number	119353
Journal	Carbohydrate Polymers
Volume	288
Early online date	17 Mar 2022
DOIs	https://doi.org/10.1016/j.carbpol.2022.119353
Publication status	Published - 15 Jul 2022

Funding

The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China ( 3210161263 and 32030084 ) and Natural Science Foundation of Tianjin Municipal Science and Technology Commission ( 20ZYJDJC00040 and 17JCJQJC45600 ).

Funders	Funder number
National Natural Science Foundation of China	3210161263, 32030084
Natural Science Foundation of Tianjin Municipal Science and Technology Commission	20ZYJDJC00040, 17JCJQJC45600

Keywords

1-Butyl-3-methylimidazolium acetate (15953398)
1-Butyl-3-methylimidazolium chloride (2734161)
1-Ethyl-3-methylimidazolium acetate (11658353)
1-Ethyl-3-methylimidazolium butyrate (25056656)
1-Ethyl-3-methylimidazolium chloride (2734160)
1-Ethyl-3-methylimidazolium propionate (25056655)
1-Propyl-3-methylimidazolium acetate (89288526)
1-Propyl-3-methylimidazolium chloride (10154187)
Acetic anhydride (7918)
Acetylated starch (24832118)
Alkyl side chain length
Choline acetate (187)
Choline butyrate (19005306)
Choline propionate (10125109)
Ion types
Ionic liquids
Native maize starch (24836924)
Starch acetylation
Viscosity

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1016/j.carbpol.2022.119353

http://Green synthesis of acetylated maize starch in different imidazolium carboxylate and choline carboxylate ionic liquidsLicence: CC BY-NC-ND

Cite this

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title = "Green synthesis of acetylated maize starch in different imidazolium carboxylate and choline carboxylate ionic liquids",

abstract = "This work demonstrates that acetylated maize starches (AMS) with varied degree of substitution (DS, 0.26–2.63) was synthesized in ionic liquids (ILs) (imidazolium chloride, imidazolium carboxylate and choline carboxylate) at 85 °C without catalyst. The DS of AMS and reaction efficiency increased with decreasing alkyl chain length of cations or anions, while decreased as the choline cation replaced the imidazolium cation and the chloride anion replaced the acetate anion. The AMS synthesized in imidazolium-based ILs exhibited much higher hydrophobicity and thermal stability than the native starch. Rheological properties of ILs and ATR-FTIR analysis of acetic anhydride/ILs mixtures indicated that a shorter alkyl side chain or the combination of an imidazolium cation and an acetate anion gave ILs lower viscosities and weaker interactions between acetic anhydride molecules, which favored the acetylation of starch. These findings provide insights into the design of green processes to modify starch and the application of acetylated starch.",

keywords = "1-Butyl-3-methylimidazolium acetate (15953398), 1-Butyl-3-methylimidazolium chloride (2734161), 1-Ethyl-3-methylimidazolium acetate (11658353), 1-Ethyl-3-methylimidazolium butyrate (25056656), 1-Ethyl-3-methylimidazolium chloride (2734160), 1-Ethyl-3-methylimidazolium propionate (25056655), 1-Propyl-3-methylimidazolium acetate (89288526), 1-Propyl-3-methylimidazolium chloride (10154187), Acetic anhydride (7918), Acetylated starch (24832118), Alkyl side chain length, Choline acetate (187), Choline butyrate (19005306), Choline propionate (10125109), Ion types, Ionic liquids, Native maize starch (24836924), Starch acetylation, Viscosity",

author = "Fei Ren and Jinwei Wang and Jinglin Yu and Cheng Zhong and Fengwei Xie and Shujun Wang",

year = "2022",

month = jul,

day = "15",

doi = "10.1016/j.carbpol.2022.119353",

language = "English",

volume = "288",

journal = "Carbohydrate Polymers",

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T1 - Green synthesis of acetylated maize starch in different imidazolium carboxylate and choline carboxylate ionic liquids

AU - Ren, Fei

AU - Wang, Jinwei

AU - Yu, Jinglin

AU - Zhong, Cheng

AU - Xie, Fengwei

AU - Wang, Shujun

PY - 2022/7/15

Y1 - 2022/7/15

N2 - This work demonstrates that acetylated maize starches (AMS) with varied degree of substitution (DS, 0.26–2.63) was synthesized in ionic liquids (ILs) (imidazolium chloride, imidazolium carboxylate and choline carboxylate) at 85 °C without catalyst. The DS of AMS and reaction efficiency increased with decreasing alkyl chain length of cations or anions, while decreased as the choline cation replaced the imidazolium cation and the chloride anion replaced the acetate anion. The AMS synthesized in imidazolium-based ILs exhibited much higher hydrophobicity and thermal stability than the native starch. Rheological properties of ILs and ATR-FTIR analysis of acetic anhydride/ILs mixtures indicated that a shorter alkyl side chain or the combination of an imidazolium cation and an acetate anion gave ILs lower viscosities and weaker interactions between acetic anhydride molecules, which favored the acetylation of starch. These findings provide insights into the design of green processes to modify starch and the application of acetylated starch.

AB - This work demonstrates that acetylated maize starches (AMS) with varied degree of substitution (DS, 0.26–2.63) was synthesized in ionic liquids (ILs) (imidazolium chloride, imidazolium carboxylate and choline carboxylate) at 85 °C without catalyst. The DS of AMS and reaction efficiency increased with decreasing alkyl chain length of cations or anions, while decreased as the choline cation replaced the imidazolium cation and the chloride anion replaced the acetate anion. The AMS synthesized in imidazolium-based ILs exhibited much higher hydrophobicity and thermal stability than the native starch. Rheological properties of ILs and ATR-FTIR analysis of acetic anhydride/ILs mixtures indicated that a shorter alkyl side chain or the combination of an imidazolium cation and an acetate anion gave ILs lower viscosities and weaker interactions between acetic anhydride molecules, which favored the acetylation of starch. These findings provide insights into the design of green processes to modify starch and the application of acetylated starch.

KW - 1-Butyl-3-methylimidazolium acetate (15953398)

KW - 1-Butyl-3-methylimidazolium chloride (2734161)

KW - 1-Ethyl-3-methylimidazolium acetate (11658353)

KW - 1-Ethyl-3-methylimidazolium butyrate (25056656)

KW - 1-Ethyl-3-methylimidazolium chloride (2734160)

KW - 1-Ethyl-3-methylimidazolium propionate (25056655)

KW - 1-Propyl-3-methylimidazolium acetate (89288526)

KW - 1-Propyl-3-methylimidazolium chloride (10154187)

KW - Acetic anhydride (7918)

KW - Acetylated starch (24832118)

KW - Alkyl side chain length

KW - Choline acetate (187)

KW - Choline butyrate (19005306)

KW - Choline propionate (10125109)

KW - Ion types

KW - Ionic liquids

KW - Native maize starch (24836924)

KW - Starch acetylation

KW - Viscosity

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U2 - 10.1016/j.carbpol.2022.119353

DO - 10.1016/j.carbpol.2022.119353

M3 - Article

C2 - 35450624

AN - SCOPUS:85126913775

SN - 0144-8617

VL - 288

JO - Carbohydrate Polymers

JF - Carbohydrate Polymers

M1 - 119353

ER -

Green synthesis of acetylated maize starch in different imidazolium carboxylate and choline carboxylate ionic liquids

Abstract

Funding

Keywords

ASJC Scopus subject areas

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