INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
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2024
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IF 3.8
Lexuan Zhao,Hongye Cheng,Zhiwen Qi
Deep eutectic solvents (DESs) have been widely utilized to intensify separations by adjusting their structures and properties, particularly in extractive deterpenation of essential oils as green alternatives to conventional organic solvents. In this work, experimental and molecular insights into efficient deterpenation intensified by a DES containing tetrabutylammonium bromide (TBAB) and levulinic acid (LEA) were investigated with citral extraction from lemon essential oil as a case study. DES formation and preferred liquid operating window were determined through solid–liquid equilibrium; an excellent extraction performance was observed at varying citral concentrations via liquid–liquid equilibria. Extraction process was simulated with a well-correlated nonrandom two-liquid model, and a 7-fold concentration of terpenoids was achieved under optimal conditions. Fourier transform infrared spectra and molecular dynamics simulations elucidated the DES formation and extraction mechanisms. Hydrogen-bonding interactions primarily mediated by −COOH group of LEA and Br– anion of TBAB resulted in lower freezing points of DES, thereby enhancing extraction performance. The results provide valuable insights into the practical applications of DESs in separating structurally similar natural products.
研究领域:
化学工程
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天然产物分离
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产品关联
DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
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2022
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IF 6.633
Zexian Qin,Hongye Cheng,Zhen Song,Lijun Ji,Lifang Chen,Zhiwen Qi
Lemon essential oil is a complex mixture with citral as the primary terpenoid and limonene as the main terpene. Isolation of terpene and terpenoid, known as deterpenation, is crucial for improving the essential oil quality. In this work, liquid–liquid extraction with deep eutectic solvents (DESs) is utilized for lemon essential oil deterpenation. The performance of 77 DESs formed by seven hydrogen bond acceptors (HBA) with eleven hydrogen bond donors (HBD) is evaluated using COSMO-RS model and verified experimentally. The influences of HBA and HBD structures are investigated and explained by σ-profile. Among 77 DESs, the DES composed of tetrabutylammonium bromide and levulinic acid, namely TBAB:LEA(1:2), is finally selected due to its better performance than the conventional solvent hydrous ethanol. The excellent performance of TBAB:LEA(1:2) in deterpenation of natural lemon essential oil suggests it is a promising solvent in the downstream processing of natural essential oil.
研究领域:
化学工程
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分析化学
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食品科学
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产品关联
DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
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2021
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IF 6.165
Mingyao Wu,Hongye Cheng,Lifang Chen,Zhiwen Qi
Separation of terpenoids from terpenes in citrus essential oils (CEOs) downstream processing is essential for practical applications. In this work, 19 deep eutectic solvents (DESs), formed by combining quaternary ammonium salts as hydrogen bond acceptors (HBAs) with alkanediols, glycols, and monocarboxylic acids as hydrogen bond donors (HBDs), were utilized to evaluate their performance in extractive deterpenation of model CEOs. The effects of HBA and HBD structures, including the alkyl chain length and the anion and HBD types, on extraction efficiency, were explored and interpreted from conductor-like screening model for realistic solvents interaction analysis. The DES TBAC:1,3BD(1:2) composed of tetrabutylammonium chloride as HBA and 1,3-butanediol as HBD was further used for liquid–liquid equilibrium investigation, where the data were well fitted using the non-random two-liquid model. With high extraction performance at various temperatures and feed concentrations, TBAC:1,3BD(1:2) is a promising candidate for extractive deterpenation of CEOs.
研究领域:
化学工程
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食品科学
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分离技术
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DOI
高影响因子
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
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2020
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IF 3.573
Jiangwuji Li,Jingwen Wang,Mingyao Wu,Hongye Cheng,Lifang Chen,Zhiwen Qi
Citrus essential oils (CEOs) are extensively utilized in the cosmetic, flavor, and chemical industries. The separation of the CEOs main compounds, terpenes and terpenoids, known as deterpenation, is required for practical applications. In this work, for deep deterpenation of the CEO, an intensified process of associative extraction was proposed for highly selective extraction of terpenoids into deep eutectic solvents (DESs) with organic salts. The formed DES was then recovered by a two-step reextraction using the antiextractants of organic solvent and water. The quaternary ammonium salt tetrabutylammonium chloride and the organic solvent n-hexane were determined based on the analysis of COSMO-RS interaction, and their extraction performance was experimentally validated. The terpeneless product (linalool with a high purity of 98.76%) was finally obtained from the model CEOs, which verifies the excellent performance for the proposed deep deterpenation process.
研究领域:
化学工程
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植物提取
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产品关联
DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
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2021
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IF 6.165
Fulin Li,Cheng Peng,Ke Yuan,Qiwei Xu,Hang Song
Terpinen-4-ol in natural Tea tree oil (TTO) plays an important role in physiological activities. Selectively removing of 1,8-cineole and the monoterpenes such as γ-terpinene from TTO is necessary for TTO comfort and safety. In this study, the density functional theory (DFT) was employed to estimate the interaction energies between ILs and terpinen-4-ol for preliminarily screening ionic liquid type of extraction agents. It was found hexalkylguanidinium ionic liquids (ILs) [diBTMG]Br exhibited good extraction distribution coefficient of terpinen-4-ol (2.54) and higher extraction selectivity of terpinen-4-ol (6.9 to 1,8-cineole and 9 to γ-terpinene, respectively). The single extraction yield of terpinen-4-ol by the IL could reach to 90%. After the extraction, subsequent twice extractions with n-hexane and water can realize satisfactorily recovery and reuse of all extraction agents. The deterpenation of TTO has advantages of lower energy consumption, safety, environmentally friendly and less cost. It would provide an alternative strategy for the practical deterpenation production of essential oil with ionic liquids.
研究领域:
化学工程
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药学
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环境科学
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有机化学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）