Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure-Biodegradation Relationship

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	Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure-Biodegradation Relationship
	Yu, Yinghao 1,2; Lu, Xingmei 1; Zhou, Qing 1; Dong, Kun 1; Yao, Hongwei 1,2; Zhang, Suojiang 1
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	2008
卷号	14 期号:35 页码:11174-11182
关键词	biodegradability green chemistry ionic liquids molecular descriptors reaction mechanisms
ISSN号	0947-6539
其他题名	Chem.-Eur. J.
中文摘要	It has been confirmed that commonly used ionic liquids are not easily biodegradable. When ultimately disposed of or accidentally released, they would accumulate in the environment, which strongly restricts large-scale industrial applications of ionic liquids. Herein, ten biodegradable ionic liquids were prepared by a single, one-pot neutralization of choline and surrogate naphthenic acids. The structures of these naphthenic acid ionic liquids (NAILs) were characterized and confirmed by (1)H and (13)C NMR spectroscopy, IR spectroscopy, and elemental analysis, and their physical properties, such as densities, viscosities, conductivities, melting points (T(m)), glass transition points (T(g)), and the onset temperatures of decomposition (T(d)), were determined. More importantly, studies showed that these NAILs would be rapidly and completely biodegraded in aquatic environments under aerobic conditions, which would make them attractive candidates to be utilized in industrial processes. To explore the underlying mechanism involved in the NAIL biodegradation reaction and seek prediction of their biodegradability under environmental conditions, four molecular descriptors were chosen: the logarithm of the n-octanol/water partition coefficient (log P), van der Waals volume (V(vdW)), energies of the highest occupied molecular orbital (E(HOMO)), and energies of the lowest unoccupied molecular orbital (E(LUMO)). Through multiple linear regression, a general and qualified model including the biodegradation percentage for NAILs after the 28-day OECD 301D test (%B(28)) and molecular descriptors was developed. Regression analysis showed that the model was statistically significant at the 99% confidence interval, thus indicating that the %B(28) Of NAILs could be explained well by the quantum chemical descriptor E(HOMO), which might give some important clues in the discovery of biodegradable ionic liquids of other kinds.
英文摘要	It has been confirmed that commonly used ionic liquids are not easily biodegradable. When ultimately disposed of or accidentally released, they would accumulate in the environment, which strongly restricts large-scale industrial applications of ionic liquids. Herein, ten biodegradable ionic liquids were prepared by a single, one-pot neutralization of choline and surrogate naphthenic acids. The structures of these naphthenic acid ionic liquids (NAILs) were characterized and confirmed by (1)H and (13)C NMR spectroscopy, IR spectroscopy, and elemental analysis, and their physical properties, such as densities, viscosities, conductivities, melting points (T(m)), glass transition points (T(g)), and the onset temperatures of decomposition (T(d)), were determined. More importantly, studies showed that these NAILs would be rapidly and completely biodegraded in aquatic environments under aerobic conditions, which would make them attractive candidates to be utilized in industrial processes. To explore the underlying mechanism involved in the NAIL biodegradation reaction and seek prediction of their biodegradability under environmental conditions, four molecular descriptors were chosen: the logarithm of the n-octanol/water partition coefficient (log P), van der Waals volume (V(vdW)), energies of the highest occupied molecular orbital (E(HOMO)), and energies of the lowest unoccupied molecular orbital (E(LUMO)). Through multiple linear regression, a general and qualified model including the biodegradation percentage for NAILs after the 28-day OECD 301D test (%B(28)) and molecular descriptors was developed. Regression analysis showed that the model was statistically significant at the 99% confidence interval, thus indicating that the %B(28) Of NAILs could be explained well by the quantum chemical descriptor E(HOMO), which might give some important clues in the discovery of biodegradable ionic liquids of other kinds.
WOS标题词	Science & Technology ; Physical Sciences
类目[WOS]	Chemistry, Multidisciplinary
研究领域[WOS]	Chemistry
关键词[WOS]	CHROMATOGRAPHY-MASS SPECTROMETRY ; TEMPERATURE MOLTEN-SALTS ; GREEN CHEMISTRY ; DESIGN ; EXTRACTION ; SOLVENTS ; CATIONS ; IMIDAZOLIUM ; MOLECULES ; TRANSPORT
收录类别	SCI ; IC
原文出处	://WOS:000261933000036
语种	英语
WOS记录号	WOS:000261933000036
公开日期	2013-10-08
内容类型	期刊论文
版本	出版稿
源URL	[http://ir.ipe.ac.cn/handle/122111/2899]
专题	过程工程研究所_研究所（批量导入）
作者单位	1.Chinese Acad Sci, Inst Proc Engn, Key Lab Green Proc & Engn, Beijing 100190, Peoples R China 2.Chinese Acad Sci, Grad Univ, Beijing 100149, Peoples R China
推荐引用方式 GB/T 7714	Yu, Yinghao,Lu, Xingmei,Zhou, Qing,et al. Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure-Biodegradation Relationship[J]. CHEMISTRY-A EUROPEAN JOURNAL,2008,14(35):11174-11182.
APA	Yu, Yinghao,Lu, Xingmei,Zhou, Qing,Dong, Kun,Yao, Hongwei,&Zhang, Suojiang.(2008).Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure-Biodegradation Relationship.CHEMISTRY-A EUROPEAN JOURNAL,14(35),11174-11182.
MLA	Yu, Yinghao,et al."Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure-Biodegradation Relationship".CHEMISTRY-A EUROPEAN JOURNAL 14.35(2008):11174-11182.