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CHEMICAL ENGINEERING JOURNAL · 2021 · IF 13.273

Enhanced recovery of acetophenone and 1‐phenylethanol from petrochemical effluent by highly porous starch-based hypercrosslinked polymers

Liqin Zhou,Kungang Chai,Xingdong Yao,Hongbing Ji

It is highly desirable to design and fabricate porous bio-based adsorbent for efficient and selective recovery of acetophenone (AP) and 1-phenylethanol (PE) from the effluent of propylene oxide and styrene monomer co-production (PO/SM) process. Herein, using cassava starch as the starting material, starch-graft-styrene hypercrosslinked polymers (SSHCPs) were designed and synthesized facilely by starch-graft-styrene copolymerization and subsequent crosslinking via a Friedel-Crafts alkylation route. SSHCP-3 (knitted by 4,4′-bis-(chloromethyl)-1,1′-biphenyl) shows high BET surface area (818 m 2 ·g −1 ), large pore volume, and high thermal stability, making it a highly efficient adsorbent for removal of aromatic pollutants from water. SSHCP-3 showed high uptake for AP (2.82 mmol·g −1 ) and selectivity (4.95) of AP over PE in binary-solute adsorption experiments. Spectral studies and theoretical calculation demonstrated that AP and PE uptake could occur at glucose units and benzene moiety via van der Waals interaction and π-π stacking interactions. SSHCP-3 also showed excellent adsorption efficiency of AP (93.6%) and PE (74.4%) in the wastewater discharged from PO/SM process. These results demonstrated that transforming styrene and starch to bio-based hypercrosslinked polymers provides an environmentally friendly and attractive strategy for recovery of AP and PE in practical application.

研究领域: 环境科学 · 材料科学 · 化学工程
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Food Chemistry-X · 2023 · IF 6.1

Manufacturing process differences give Keemun black teas their distinctive aromas

Yujie Xu,Yaqin Liu,Jihong Yang,Hui Wang,Hanchen Zhou,Pandeng Lei

Traditional Keemun black tea is also known as Congou black tea (CF). Over the last three decades, three other types of Keemun black tea (Jinzhen, JZ; Maofeng, MF; Xiangluo, XL) made by different processing have been introduced into the tea market. Total CF volatile concentrations ranged from 1666.3 to 2185.7 μg/L, followed by XL (1193.5–1916.1 μg/L), JZ (1058.9–1811.0 μg/L), and MF (987.5–1518.0 μg/L) tea infusions. A total of 79 volatiles in tea infusions was identified by two methods, among which fourteen with OAVs > 1 were identified and OAVs proportion of volatiles with flowery, fruity, or sweet notes to those with other notes differed in four Keemun black teas (CF = 6.58:1, MF = 5.16:1, JZ = 4.04:1, XL = 5.11:1). Phenylethyl alcohol oxidation resulted in phenylacetaldehyde formation which is the characteristic odorant in Keemun black tea. We clearly show that changes in tea processing gives the distinctive aroma to different Keemun black teas.

研究领域: 食品科学 · 植物学
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POLYMER BULLETIN · 2019 ·Vol. 77 ·期 2 ·989-1001 · IF 1.858

Microencapsulation of 2-phenyl ethanol with methylcellulose/alginate/methylcellulose as the wall material and stability of the microcapsules

Qiu Bining,Tian Hua,Yin Xueqiong,Zhou You,Zhu Li

In this study, 2-phenyl ethanol (2-PEA) was microencapsulated with natural and semisynthetic carbohydrate polymers as the wall material. The wall material components methylcellulose (MC), alginate sodium (ALG), and carboxymethyl chitosan were optimized according to the results of microscopy images, zeta potential, and 2-PEA content. The combination of MC/ALG/MC was selected as the best wall components. Cobalt chloride (CoCl 2 ) was used as the core material to prepare microcapsules whose color was measured with a colorimeter to intuitively express the water absorption of the microcapsules. The absorbed water mass and b* were related to one variable quadratic equation. The rapid release properties and the natural long-term release properties of 2-PEA microcapsules were measured.

研究领域: 食品科学 · 材料科学
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FOOD CHEMISTRY · 2018 · IF 4.946

Study of the biochemical formation pathway of aroma compound 1-phenylethanol in tea (Camellia sinensis (L.) O. Kuntze) flowers and other plants

Ying Zhou,Qiyuan Peng,Lanting Zeng,Jinchi Tang,Jianlong Li,Fang Dong,Ziyin Yang

After tea leaves, tea ( Camellia sinensis ) flowers are becoming a second tea plant resource because they contain not only functional metabolites similar to those found in tea leaves, but also predominant amounts of functional metabolites that only occur in tea leaves in small amounts. 1-Phenylethanol (1PE) is a predominant aroma compound found in tea flowers. A 1PE synthase in tea flowers was isolated, functionally characterized, and shown to have the highest catalytic efficiency for the conversion of acetophenone (AP). To determine why 1PE accumulates more in tea flowers than other plants, we compared their 1PE contents and used a stable isotope labeling method to elucidate the 1PE biosynthetic route. Supplementation with [ 2 H 8 ] l -phenylalanine and [ 2 H 5 ]AP suggested that most plants containing the enzyme/gene catalyzed the conversion of AP to 1PE. Furthermore, the availability of AP derived from l -phenylalanine was responsible for the difference in 1PE accumulation between tea flowers and other plants.

CAS / MDL: 75-09-2
研究领域: 植物学 · 生物化学 · 植物代谢
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SEPARATION AND PURIFICATION TECHNOLOGY · 2024 · IF 8.1

Covalent functionalization of NH2-MIL-101(Cr) with bovine serum albumin for enatioselectic separation of racemic 1-phenylethanol

Yanyan Xing,Mengke Tian,Ruoman Ji,Ting Wang,Xiaohong Hou

The immobilization of bovine serum albumin (BSA) with high efficiency, good reproducibility and stability for chiral separation has attracted much attention in the medicinal field. BSA was immobilized into MIL-101(Cr) by three ways for efficient chiral separation in this research. MIL-101(Cr)@BSA was firstly prepared by adsorption, NH 2 -MIL-101(Cr) ⊂ BSA by direct bonding, and NH 2 -MIL-101(Cr) ⊂ Glu ⊂ BSA by glutaraldehyde crosslinking bonding. Compared to the other two materials, NH 2 -MIL-101(Cr) ⊂ BSA as a new enantioselective separator, with the most BSA loading rate of 437.6 mg g −1 exhibited excellent chiral separation performances and succeeded in realizing a complete chiral separation of racemic 1–phenylethanol within 14 s. It was found that the NH 2 -MIL-101(Cr) ⊂ BSA was more strongly bound to R -1-phenylethanol and the ee value could reach 100 % when the material was added in three batches. The different interactions between BSA and racemates mainly including hydrogen bonding, hydrophobic interaction and π-π interaction were revealed by the molecular docking studies, especially hydrogen bonding, accounting for the observed selective chiral recognition capacity of racemic 1–phenylethanol of NH 2 -MIL-101(Cr) ⊂ BSA. Moreover, both of NH 2 -MIL-101(Cr) ⊂ BSA and NH 2 -MIL-101(Cr) ⊂ Glu ⊂ BSA showed excellent stability and reusability. This combination of theory and experiment provided a clearer basis for other researchers to have different requirements for protein immobilization, and provided new ideas and methods for the development of chiral selectors.

CAS / MDL: 10312-55-7 111-30-8
研究领域: 生物化学 · 材料科学 · 医药工程
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JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES · 2015 · IF 0.606

Fast Quantification of Phenylethyl Alcohol in Rose Water and Chemical Profiles of Rose Water and Oil of Rosa damascena and Rosa rugosa from Southeast China

Gaoming Lei,Longhu Wang,Xuesong Liu,Anyun Zhang

A new and effective high performance liquid chromatography (HPLC) method was developed for fast quantification of phenylethyl alcohol in rose water. Chemical profiles of rose water and oil of Rosa damascena and Rosa rugosa from Southeast China were investigated by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). Fast HPLC was achieved by rapid sample preparation and fast elution using acetonitrile–water (35:65, v/v) on Zorbax SB-C18. It was validated and applied to rapid analysis of different rose water samples, in which the contents of phenylethyl alcohol ranged from 454.6 to 526.7 µg/mL. GC and GC–MS revealed that rose water volatiles of R. damascena and R. rugosa mainly consisted of phenylethyl alcohol (90.2% and 78.7%, respectively) and citronellol (4.5% and 13.5%, respectively). This is the first report on fast HPLC quantification of phenylethyl alcohol in rose water and chemical profiles of rose water volatiles of R. damascena and R. rugosa from Southeast China. The developed HPLC method can serve as a fast quality control during rose water production.

研究领域: 植物化学 · 分析化学
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BIOSENSORS & BIOELECTRONICS · 2017 · IF 7.78

Multichannel electroanalytical devices for competitive ELISA of phenylethanolamine A

Yang Liu,Meng Cai,Weiping Wu,Yuting Fang,Pei She,Shouming Xu,Jianguo Li,Kang Zhao,Jingjuan Xu,Ning Bao,Anping Deng

Herein, we reported a disposable electroanalytical device for competitive enzyme-linked immunosorbent assay (ELISA) of phenylethanolamine A (PA). Conductive carbon tape coated with gold cluster served as the working electrode , while the counter and reference electrodes were fabricated on the filter paper by the screen-printing technique. Separating fabrication of the working electrode from other electrodes could make it possible for full utilization of the working electrode modification in bulk and no contamination of the immune-reagents on the counter and reference electrodes. The gold cluster played an important role in both immobilizing antigen and accelerating electron transfer . The eight-channel devices were utilized to detect PA on the strategy of competitive ELISA. The detection range and the limit of detection (LOD) using differential pulse voltammetry for PA were 0.005–60   ng   mL −1 and 2.6   pg   mL −1 , respectively. And also, the linear range for PA performed by square wave voltammetry was 0.05–60   ng   mL −1 with the LOD value as 0.028   ng   mL −1 . The results clearly demonstrated that the proposed electroanalytical devices could be successfully applied in immunoassay and might be further developed for determination of different analytes based on ELISA format.

研究领域: 分析化学 · 免疫学
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY · 2020 · IF 3.306

Visible light catalyzed anti-markovnikov hydration of styrene to 2-phenylethanol: From batch to continuous

Yuhang Chen,Jie Zhang,Zhiyong Tang,Yuhan Sun

The 2-phenylethanol production by traditional chemical methods requires multi-step reactions, in which harsh conditions such as high temperature or strong acid/base are required and undesired by-products are easily produced. The visible light catalyzed anti-Markovnikov hydration of styrene is a single-step reaction using non-toxic catalyst under mild conditions. However, this reaction usually takes ten or even dozens of hours, facing the problem in scale up. The present work aims to intensify this reaction in continuous flow microreactor with comparison to traditional batch reactor. The effects of light source shape, reaction temperature, substrate concentration and catalyst concentration on the reaction were investigated. The continuous flow microreactor permitted to ensure more uniform light intensity and larger specific surface area, the reaction rate could thus be enhanced. The maximum productivity of 2-phenylethanol was 0.122 mol/(L.h), which was 2.5 times higher than that obtained in test tube under the same reaction conditions and 34 times higher than that reported in previous literature. The optimal photosensitizer concentration was 2 %. The increase of substrate concentration would lead to the addition reaction between styrene cationic intermediates with styrene, thereby decreasing the selectivity of 2-phenylethanol.

研究领域: 化学工程 · 催化化学
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APPLIED SURFACE SCIENCE · 2025 · IF 6.9

Unraveling the efficient separation of positional phenylethanol isomers by aluminum-based metal–organic frameworks: The role of pore geometry and multiple molecular interactions

Gankai Huang,Yubao Wang,Yan Du,Qunhua Long,Kungang Chai

Adsorption-based separation of 2-phenylethanol (2-PE) and 1-phenylethanol (1-PE) is crucial yet challenging in the petrochemical industry. In this study, we report that an ultra-micropore aluminum-based metal–organic framework (Al-MOF) (i.e., CAU-23) exhibits higher 2-PE/1-PE selectivity (6.12) and 2-PE adsorption capacity (2.52 mmol g −1 ) in liquid phase compared to its pseudo-isostructural analogue of Al-MOFs, MIL-160 and MOF-303 at 293 K. The micropore diffusion model was employed to give the best fit to the adsorption kinetics of the CAU-23 with a rate achieved higher than MIL-160 and MOF-303. Computational analysis confirmed that 2-PE preferential adsorption stems from CAU-23′s well-matched pore geometry which enables efficient molecular confinement. In combination of inspecting the static adsorption properties of 2-PE and 1-PE onto CAU-23, we found that the superior affinity of CAU-23 toward 2-PE over 1-PE originates from entropy and enthalpy effect. The remarkable 2-PE/1-PE separation capability of CAU-23 was confirmed through breakthrough curve analysis (separation factor ≈ 4). As the first Al-MOF developed for 2-PE/1-PE separation, CAU-23 offers valuable insights into the design of advanced 2-PE-selective adsorbents.

CAS / MDL: 91-20-3 98-85-1
研究领域: 化学工程 · 材料科学 · 吸附技术 · 分离科学 · 计算化学
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Catalysts · 2018 ·Vol. 8 ·期 1 ·13 · IF 3.465

Immobilized Burkholderia cepacia Lipase on pH-Responsive Pullulan Derivatives with Improved Enantioselectivity in Chiral Resolution

Li Xu,Guli Cui,Caixia Ke,Yanli Fan,Yunjun Yan

A kind of pH-responsive particle was synthesized using modified pullulan polysaccharide. The synthesized particle possessed a series of merits, such as good dispersity, chemical stability and variability of particle size, making it a suitable carrier for enzyme immobilization. Then,Burkholderia cepacialipase (BCL), a promising biocatalyst in transesterification reaction, was immobilized on the synthesized particle. The highest catalytic activity and immobilization efficiency were achieved at pH 6.5 because the particle size was obviously enlarged and correspondingly the adsorption surface for BCL was significantly increased. The immobilization enzyme loading was further optimized, and the derivative lipase was applied in chiral resolution. Under the optimal reaction conditions, the immobilized BCL showed a very good performance and significantly shortened the reaction equilibrium time from 30 h of the free lipase to 2 h with a conversion rate of 50.0% andeesat 99.2%. The immobilized lipase also exhibited good operational stability; after being used for 10 cycles, it still retained over 80% of its original activity. Moreover, it could keep more than 80% activity after storage for 20 days at room temperature in a dry environment. In addition, to learn the potential mechanism, the morphology of the particles and the immobilized lipase were both characterized with a scanning electron microscope and confocal laser scanning microscopy. It was found that the enlarged spherical surface of the particle in low pH values probably led to high immobilized efficiency, resulting in the improvement of enantioselectivity activity in chiral resolution.Keywords:immobilization;Burkholderia cepacialipase;chiral resolution;1-phenylethanol;pullulan

CAS / MDL: 9057-02-7
研究领域: 生物化学 · 酶工程
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MOLECULES · 2022 ·Vol. 27 ·期 21 ·7390 · IF 4.927

Phenylethanoid and Phenylmethanoid Glycosides from the Leaves of Ligustrum robustum and Their Bioactivities

Shi-Hui Lu,Hao-Jiang Zuo,Jing Huang,Ran Chen,Jia-Ping Pan,Xiu-Xia Li

The phytochemical study on the leaves ofLigustrum robustum, which have been used as Ku-Ding-Cha, led to the isolation and identification of three new phenylethanoid glycosides and three new phenylmethanoid glycosides, named ligurobustosides R1(1b), R2–3(2), R4(3), S1(4b), S2(5), and S3(6), and five reported phenylethanoid glycosides (7–11). In the bioactivity test, (Z)-osmanthuside B6(11) displayed strong fatty acid synthase (FAS) inhibitory activity (IC50: 4.55 ± 0.35 μM) as the positive control orlistat (IC50: 4.46 ± 0.13 μM), while ligurobustosides R4(3) and S2(5), ligupurpuroside B (7),cis-ligupurpuroside B (8), ligurobustoside N (9), osmanthuside D (10), and (Z)-osmanthuside B6(11) showed stronger ABTS radical scavenging activity (IC50: 2.68 ± 0.05~4.86 ± 0.06 μM) than the positive control L-(+)-ascorbic acid (IC50: 10.06 ± 0.19 μM). This research provided a theoretical basis for the leaves ofL. robustumas a tea with function in treating obesity and diabetes.Keywords:Ligustrum robustum;phenylethanoid glycoside;phenylmethanoid glycosides;FAS;α-glucosidase;antioxidant;anti-obesity;hypoglycemic

CAS / MDL: 28752-68-3
研究领域: 植物化学 · 药理学 · 代谢生物学
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2021 · IF 2.694

Isobaric Vapor–Liquid Equilibrium for the Binary Systems of 2-Phenylethanol + 2-Ethylphenol, 1-Phenyl-2-propanol + 2-Ethylphenol, 2-Phenylethanol + 1-Phenyl-2-propanol and 2-Phenyl-1-propanol + 2-Ethylphenol under 101.3 kPa

Qing Yi,Wei-Peng Chen,Xiang-yang Zhang,Yan-Yang Wu,Bin Wu,Kui Chen,Li-Jun Ji

The isobaric vapor–liquid equilibrium (VLE) data of 2-phenylethanol (2-PE) + 2-ethylphenol (2-EP), 1-phenyl-2-propanol (1,2-PP) + 2-ethylphenol (2-EP), 2-phenylethanol (2-PE) + 1-phenyl-2-propanol (1,2-PP) and 2-phenyl-1-propanol (2,1-PP) + 2-ethylphenol (2-EP) were measured by a modified Rose type still under 101.3 kPa. Both the Fredenslund test and Redlich–Kister area test were employed to verify the consistency of the experimental data. Besides, the experimental isobaric VLE data were correlated by Wilson, nonrandom two-liquid, and universal quasi-chemical models, and the corresponding parameters were obtained accordingly. All three models showed good agreement with the experimental data, and among which the Wilson model performed slightly better than the others.

研究领域: 化学工程 · 物理化学
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