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重新思考酯季铵盐:结构中含有甜菜碱或胆碱类似物作为阳离子的酯季铵盐的合成、稳定性、生态毒性和应用。

Rethinking the Esterquats: Synthesis, Stability, Ecotoxicity and Applications of Esterquats Incorporating Analogs of Betaine or Choline as the Cation in Their Structure.

机构信息

Chair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Rokietnicka 3, 60-806 Poznan, Poland.

Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, 60-965 Poznan, Poland.

出版信息

Int J Mol Sci. 2024 May 25;25(11):5761. doi: 10.3390/ijms25115761.


DOI:10.3390/ijms25115761
PMID:38891947
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11171562/
Abstract

Esterquats constitute a unique group of quaternary ammonium salts (QASs) that contain an ester bond in the structure of the cation. Despite the numerous advantages of this class of compounds, only two mini-reviews discuss the subject of esterquats: the first one (2007) briefly summarizes their types, synthesis, and structural elements required for a beneficial environmental profile and only briefly covers their applications whereas the second one only reviews the stability of selected betaine-type esterquats in aqueous solutions. The rationale for writing this review is to critically reevaluate the relevant literature and provide others with a "state-of-the-art" snapshot of choline-type esterquats and betaine-type esterquats. Hence, the first part of this survey thoroughly summarizes the most important scientific reports demonstrating effective synthesis routes leading to the formation of both types of esterquats. In the second section, the susceptibility of esterquats to hydrolysis is explained, and the influence of various factors, such as the pH, the degree of salinity, or the temperature of the solution, was subjected to thorough analysis that includes quantitative components. The next two sections refer to various aspects associated with the ecotoxicity of esterquats. Consequently, their biodegradation and toxic effects on microorganisms are extensively analyzed as crucial factors that can affect their commercialization. Then, the reported applications of esterquats are briefly discussed, including the functionalization of macromolecules, such as cotton fabric as well as their successful utilization on a commercial scale. The last section demonstrates the most essential conclusions and reported drawbacks that allow us to elucidate future recommendations regarding the development of these promising chemicals.

摘要

酯基季铵盐是一类独特的季铵盐(QAS),其阳离子结构中含有酯键。尽管这类化合物具有许多优点,但仅有两篇小型综述讨论了酯基季铵盐的主题:第一篇(2007 年)简要总结了它们的类型、合成以及对环境有利所需的结构要素,仅简要涵盖了它们的应用,而第二篇仅综述了选定的甜菜碱型酯基季铵盐在水溶液中的稳定性。撰写这篇综述的理由是批判性地重新评估相关文献,并为其他人提供胆碱型酯基季铵盐和甜菜碱型酯基季铵盐的“最新”快照。因此,本调查的第一部分彻底总结了最重要的科学报告,这些报告展示了有效合成路线的形成,从而形成了这两种类型的酯基季铵盐。在第二部分,解释了酯基季铵盐易水解的原因,并对各种因素(如 pH 值、盐度程度或溶液温度)的影响进行了彻底分析,包括定量成分。接下来的两个部分涉及与酯基季铵盐的生态毒性相关的各个方面。因此,对其生物降解性以及对微生物的毒性影响进行了广泛分析,这是影响其商业化的关键因素。然后,简要讨论了酯基季铵盐的应用,包括对棉织物等大分子的功能化以及它们在商业规模上的成功利用。最后一部分展示了最基本的结论和报告的缺点,使我们能够阐明有关这些有前途的化学品开发的未来建议。

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引用本文的文献

[1]
Production of an Esterquat-Based Novel Softening Agent and Its Impact on Leather and Textile Quality.

ACS Omega. 2025-3-3

[2]
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本文引用的文献

[1]
Choline degradation in : identification of sources of formaldehyde.

J Bacteriol. 2024-4-18

[2]
Ecotoxicity studies reveal that organic cations in dicamba-derived ionic liquids can pose a greater environmental risk than the herbicide itself.

Sci Total Environ. 2024-4-20

[3]
Are natural deep eutectic solvents always a sustainable option? A bioassay-based study.

Environ Sci Pollut Res Int. 2023-2

[4]
Toward revealing the role of the cation in the phytotoxicity of the betaine-based esterquats comprising dicamba herbicide.

Sci Total Environ. 2022-11-1

[5]
Ionic liquids as a useful tool for tailoring active pharmaceutical ingredients.

J Control Release. 2021-10-10

[6]
Novel approach on the synthesis of starch betainate by transesterification.

Int J Biol Macromol. 2021-7-1

[7]
Novel esterquat-based herbicidal ionic liquids incorporating MCPA and MCPP for simultaneous stimulation of maize growth and fighting cornflower.

Ecotoxicol Environ Saf. 2021-1-15

[8]
Iodosulfuron-Methyl-Based Herbicidal Ionic Liquids Comprising Alkyl Betainate Cation as Novel Active Ingredients with Reduced Environmental Impact and Excellent Efficacy.

J Agric Food Chem. 2020-11-25

[9]
Herbicidal Ionic Liquids: A Promising Future for Old Herbicides? Review on Synthesis, Toxicity, Biodegradation, and Efficacy Studies.

J Agric Food Chem. 2020-9-30

[10]
Insights into the Properties and Potential Applications of Renewable Carbohydrate-Based Ionic Liquids: A Review.

Molecules. 2020-7-20

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