Synthesis and evaluation of the biodegradability potential of Cholinium-based ionic liquids and deep eutectic solvents

IF 5.2 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Liquids Pub Date : 2025-09-23 DOI:10.1016/j.molliq.2025.128575

Zacharoula Zampeti, Achilleas Papadopoulos, Maria-Anna Karadendrou, Anastasia Detsi, Andromachi Tzani

{"title":"Synthesis and evaluation of the biodegradability potential of Cholinium-based ionic liquids and deep eutectic solvents","authors":"Zacharoula Zampeti, Achilleas Papadopoulos, Maria-Anna Karadendrou, Anastasia Detsi, Andromachi Tzani","doi":"10.1016/j.molliq.2025.128575","DOIUrl":null,"url":null,"abstract":"<div><div>Ionic Liquids (ILs) and Deep Eutectic Solvents (DESs) are two promising classes of solvents, often labeled as “green” alternatives to conventional organic solvents due to their tunable physicochemical properties.</div><div>In this study a series of six DESs and nine ILs were successfully synthesized, structurally characterized by <sup>1</sup>H NMR spectroscopy, and assessed for their biodegradability via the BOD<sub>5</sub> closed-bottle test. All the synthesized solvent systems, share the same structural feature of a cholinium cation, whereas a series of carboxylic acids was used to act either as counterion (in the case of protic ILs) or the hydrogen bond donors (in the case of DES). Despite the growing interest in green solvents, to our knowledge, no prior studies were set to examine and compare the biodegradability of ILs and DESs formed from the same or structurally similar components.</div><div>Among the ILs and DESs, biodegradability rates reached up to 81.3 % and 86.1 % respectively. Five ILs (IL<sub>2-3</sub>and IL<sub>6</sub><sub>–</sub><sub>9</sub>) and two DESs (DES<sub>4</sub> and DES<sub>6</sub>), exceeded 60 % biodegradability within five days, surpassing the OECD's 28-day threshold for classification as “readily biodegradable.”</div><div>The BOD results indicate that ILs and DESs composed by the same starting materials tend to exhibit varying biodegradability rates, possibly due to different molecular interactions existing in the systems (mainly ionic and electrostatic interactions in ILs and hydrogen bond and Van der Waals interactions in DES). Overall, the results demonstrate that the majority of the synthesized solvents were found to be readily biodegradable.</div></div>","PeriodicalId":371,"journal":{"name":"Journal of Molecular Liquids","volume":"437 ","pages":"Article 128575"},"PeriodicalIF":5.2000,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Molecular Liquids","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0167732225017520","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}

引用次数: 0

Abstract

Ionic Liquids (ILs) and Deep Eutectic Solvents (DESs) are two promising classes of solvents, often labeled as “green” alternatives to conventional organic solvents due to their tunable physicochemical properties.

In this study a series of six DESs and nine ILs were successfully synthesized, structurally characterized by ¹H NMR spectroscopy, and assessed for their biodegradability via the BOD₅ closed-bottle test. All the synthesized solvent systems, share the same structural feature of a cholinium cation, whereas a series of carboxylic acids was used to act either as counterion (in the case of protic ILs) or the hydrogen bond donors (in the case of DES). Despite the growing interest in green solvents, to our knowledge, no prior studies were set to examine and compare the biodegradability of ILs and DESs formed from the same or structurally similar components.

Among the ILs and DESs, biodegradability rates reached up to 81.3 % and 86.1 % respectively. Five ILs (IL_2-3and IL₆_–₉) and two DESs (DES₄ and DES₆), exceeded 60 % biodegradability within five days, surpassing the OECD's 28-day threshold for classification as “readily biodegradable.”

The BOD results indicate that ILs and DESs composed by the same starting materials tend to exhibit varying biodegradability rates, possibly due to different molecular interactions existing in the systems (mainly ionic and electrostatic interactions in ILs and hydrogen bond and Van der Waals interactions in DES). Overall, the results demonstrate that the majority of the synthesized solvents were found to be readily biodegradable.

查看原文本刊更多论文

基于胆碱的离子液体和深度共晶溶剂的生物降解潜力的合成与评价

离子液体（ILs）和深共晶溶剂（DESs）是两种很有前途的溶剂，由于其可调的物理化学性质，通常被标记为传统有机溶剂的“绿色”替代品。本研究成功合成了6个DESs和9个il，通过1H NMR对其进行了结构表征，并通过BOD5闭瓶试验对其生物降解性进行了评价。所有合成的溶剂体系都具有相同的胆离子结构特征，而一系列羧酸被用来作为反离子（在质子ILs的情况下）或氢键供体（在DES的情况下）。尽管人们对绿色溶剂的兴趣日益浓厚，但据我们所知，之前还没有研究对由相同或结构相似的组分形成的il和DESs的生物降解性进行检验和比较。il和DESs的生物降解率分别达到81.3%和86.1%。5种il （il - 2-3和il - 6 - 9）和2种DESs （DES4和DES6）在5天内生物降解率超过60%，超过了经合组织28天的“易生物降解”分类门槛。BOD结果表明，由相同起始材料组成的il和DES往往表现出不同的生物降解率，这可能是由于系统中存在不同的分子相互作用（il主要是离子和静电相互作用，DES主要是氢键和范德华相互作用）。总的来说，结果表明，大多数合成溶剂是易于生物降解的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of Molecular Liquids 化学-物理：原子、分子和化学物理

CiteScore

10.30

自引率

16.70%

发文量

2597

审稿时长

78 days

期刊介绍： The journal includes papers in the following areas: – Simple organic liquids and mixtures – Ionic liquids – Surfactant solutions (including micelles and vesicles) and liquid interfaces – Colloidal solutions and nanoparticles – Thermotropic and lyotropic liquid crystals – Ferrofluids – Water, aqueous solutions and other hydrogen-bonded liquids – Lubricants, polymer solutions and melts – Molten metals and salts – Phase transitions and critical phenomena in liquids and confined fluids – Self assembly in complex liquids.– Biomolecules in solution The emphasis is on the molecular (or microscopic) understanding of particular liquids or liquid systems, especially concerning structure, dynamics and intermolecular forces. The experimental techniques used may include: – Conventional spectroscopy (mid-IR and far-IR, Raman, NMR, etc.) – Non-linear optics and time resolved spectroscopy (psec, fsec, asec, ISRS, etc.) – Light scattering (Rayleigh, Brillouin, PCS, etc.) – Dielectric relaxation – X-ray and neutron scattering and diffraction. Experimental studies, computer simulations (MD or MC) and analytical theory will be considered for publication; papers just reporting experimental results that do not contribute to the understanding of the fundamentals of molecular and ionic liquids will not be accepted. Only papers of a non-routine nature and advancing the field will be considered for publication.