Molecular Catalysis
·
2024
·
IF 3.9
Hui Cao,Yu Liu,Yanqiu Li,Yingxiong Wang,Yan Qiao
The α-hydroxyketones and 1,2-diols are versatile building blocks for the preparation of many natural and synthetic bioactive compounds. In this study, N-heterocyclic carbon (NHC) promoted coupling of several aldehydes with formaldehyde enabled the synthesis of 1,2-diols in moderate to high yields. The highly selective conversion of several aldehydes and formaldehyde into 1,2-diols and α-hydroxyketones was achieved in a one-pot two-step process via [BHMIm][OAc] as a key intermediate. In the first step, formaldehyde was quantitatively converted to [BHMIm][OAc] through the carbene addition. In the second step, 1,2-diol was produced through the intermediate-promoted aldol reaction. The results showed that benzaldehyde was capable to react with [BHMIm][OAc] efficiently, with a 54.1% yield of 1,2-diol after the 3-hour reaction at 85 °C. Among the tested benzaldehyde derivatives, the 4-nitrobenzaldehyde showed the highest yield of 1,2-diol (73.3%) under the optimized reaction conditions. Incorporation of an electron rich group on benzaldehyde promoted carbene regeneration. With 4-methoxybenzaldehyde as the substrate, the yield of α-hydroxyketone reached a maximum of 30.6%. Additionally, dihydroxyacetone derivatives were detected in the system. In situ NMR technique confirmed that it was generated from the further reaction of the carbene/1,2-diol complex with another aldehyde. Based on the results of NMR spectroscopy and mass spectrometry, a possible reaction pathway was also proposed.
研究领域:
有机化学
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合成化学
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产品关联
DOI
高影响因子
CHROMATOGRAPHIA
·
2017
·Vol. 80
·期 8
·1179-1188
·
IF 1.402
Li Ben,Guo Wei,Chi Haijun,Kimura Masaru,Ramsey Edward D.
A high-pressure photochemical reaction cell operated with a magnetic stir drive has been directly interfaced on-line with either SFC or HPLC. The interface consisted of an oven housing a recirculation pump directly connected to a sample injection valve. The inlet of the recirculation pump and the outlet from the sample injection valve were connected to the stirred reaction cell such that a return flow circuit was established. With this arrangement, a continuous flow of fresh supercritical fluid photochemical reaction mixture was maintained through the sample injection valve. This enabled samples of reaction mixture to be conveniently analyzed at regular intervals to monitor reaction progress using either on-line SFC or HPLC. The photoreduction of benzophenone in the presence of propan-2-ol to produce 1,1,2,2-tetraphenylethane-1,2-diol and 2-methyl-1,1-diphenylpropan-1,2-diol was studied. For this reaction, on-line SFC provided significantly better performance than on-line HPLC and was therefore used to monitor overall reaction progress and the different product yields. Quantitative results for this study demonstrate that highly efficient photochemical reactions proceeded in supercritical fluid carbon dioxide at 13 and 20 MPa.
研究领域:
化工工程
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分析化学
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光化学
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超临界流体技术
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DOI
高影响因子
Reaction Chemistry & Engineering
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2024
·
IF 3.4
Shaoyuan Guo,Xinli Tong,Jipeng Wang,Hang Tang
The use of high-entropy oxides (HEOs) in heterogeneous catalysis is a fascinating research direction in the chemical field. In this work, a highly selective aerobic oxidative C–C bond cleavage using a 1,2-diol and lignin model is achieved with the HEOs-derived multimetallic catalyst. In the transformation of 1-phenyl-1,2-ethanediol, a 96.1% conversion with 96.2% selectivity of benzaldehyde was obtained using MgCuMnFeCo–R as the catalyst. Therein, the partial reduction of Fe2+ and Co2+ leading to the formation of numerous oxygen vacancies, plays a crucial role in the excellent catalytic activity. Moreover, this HEO-derived catalyst could maintain high activity even after being reused more than 10 times.
研究领域:
化学
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催化科学
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DOI
高影响因子
ChemSusChem
·
2020
·Vol. 13
·期 19
·5248-5255
·
IF 7.962
Rui Zhu,Gongyu Zhou,Jia-nan Teng,Xinglong Li,Yao Fu
Graphical Oxidative cleavage : A heterogeneous metal-free photocatalytic system is developed for oxidative cleavage of C−C bonds in 1,2-diols at mild conditions (visible light, room temperature, no base, O 2 balloon). The reaction mechanism is studied through a series of control experiments and DFT calculations. In addition, the catalytic system has a broad substrate scope, including aliphatic, benzylic, alkenyl 1,2-diols, and α-hydroxy acids such as lactic acid. The preparation of carbonyl compounds by the aerobic oxidative cleavage of C−C bonds in 1,2-diols under mild reaction conditions is a very significant reaction and is widely employed in various scenarios. Avoiding the use of harmful stoichiometric oxidants and adopting a greener chemical process remain a challenge for this reaction to date. In this manuscript, a heterogeneous metal-free photocatalytic strategy without any additive was developed for aerobic oxidative cleavage of C−C bonds in 1,2-diols at ambient conditions with visible light. The reaction mechanism was further studied through a series of control experiments and density functional theory (DFT) calculations. In addition, the catalytic system showed a broad substrates scope, including aliphatic (linear or cyclic) 1,2-diols, benzylic, alkenyl 1,2-diols, and α-hydroxy acids (such as lactic acid). Thus, this strategy could serve as a method for the transformation of 1,2-diols to corresponding carbonyl compounds by the aerobic oxidative cleavage of C−C bonds.
研究领域:
有机化学
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催化化学
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环境化学
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DOI
高影响因子
FOOD CHEMISTRY
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2023
·
IF 8.8
Wei Jia,Xin Wang
The potential mechanisms about the health risks of endogenous 3-MCPD remain elusive. Here, we researched the influences of 3-MCPD on the metabolic landscape of digested goat infant formulas via integrative UHPLC-Q-Orbitrap HRMS-MS/MS-based peptidomics and metabolomics (%RSDs ≤ 7.35 %, LOQ 2.99–58.77 μg kg −1 ). Digested goat infant formulas under 3-MCPD-interference caused metabolic perturbation by down-regulating levels of peptides VGINYWLAHK (5.98–0.72 mg kg −1 ) and HLMCLSWQ (3.25–0.72 mg kg −1 ) pertained to health-promoting bioactive components, and accelerated the down-regulation of non-essential amino acids (AAs, l -tyrosine 0.88–0.39 mg kg −1 , glutamic acid 8.83–0.88 μg kg −1 , and d -aspartic acid 2.93–0.43 μg kg −1 ), semi-essential AA ( l -arginine 13.06–8.12 μg kg −1 ) and essential AAs ( l -phenylalanine 0.49–0.05 mg kg −1 ) that provide nutritional value. Peptidomics and metabolomics interactions elucidated that 3-MCPD altered the stability of α-lactalbumin and d -aspartate oxidase in a dose-dependent manner, and affected the flavor perception of goat infant formulas, leading to a decline of nutritional value of goat infant formulas.
研究领域:
营养学
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毒理学
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分析化学
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产品关联
DOI
PubMed
高影响因子
LANGMUIR
·
2024
·
IF 3.7
Haochuan Lu,Lining Bao,Qingwen Dong,Xu Li,Jinxiang Dong
Branched surfactants exhibit a lower surface tension, excellent low defoaming performance, and better wetting ability compared with linear surfactants, making them promising for applications in industrial cleaning. In this study, 2-hexyl-1-decene (C8 olefin dimer), obtained from the dimerization of 1-octene, was used as the hydrophobe to synthesize branched nonionic surfactants via hydroxylation and ethoxylation. The hydroxylation of the C8 olefin dimer to synthesize 2-hexyldecane-1,2-diol (C8 BD) using H2O2 and HCOOH was investigated systematically. Under the optimal reaction conditions (H2O2/C8 olefin dimer molar ratio: 1.5, HCOOH/C8 olefin dimer molar ratio: 4.0, reaction time: 10 h, reaction temperature: 50 °C), the conversion of the C8 olefin dimer and selectivity toward C8 BD were found to reach 99.96 and 79.89%, respectively. Further, branched nonionic surfactants (C8 BDEn) were synthesized via ethoxylation of C8 BD with ethylene oxide and characterized using FTIR, LCMS, 1H NMR, and 13C NMR techniques. The presence of a tertiary hydroxyl group in C8 BD increases the reactivity of the primary hydroxyl group, leading to a narrower range of products and lower residual substrate content. The physicochemical properties and surface properties of C8 BDEn with different degrees of ethoxylation at various concentrations were investigated and compared with those of commercially available Guerbet alcohol polyoxyethylene ethers (C8 GAEO9 and C6 GAEO9). The results show that, compared with C8 GAEO9 and C6 GAEO9, C8 BDE6 displayed a higher surface activity with a lower equilibrium surface tension (27.14 mN·m–1), superior wettability with a smaller contact angle (39.2°), better emulsification performance with a longer emulsification time of 548 s, and excellent foaming properties (initial foam volume of 11.6 mL). This strategy of utilizing coal-based α-olefins for the synthesis of branched nonionic surfactants presents a route to prepare value-added fine chemicals from coal-based resources.
研究领域:
化学工程
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材料科学
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产品关联
DOI
PubMed
高影响因子
Arabian Journal of Chemistry
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2021
·
IF 5.165
Aka Alla Martin,Essy Kouadio Fodjo,Zran Vanh Eric-Simon,Zhen Gu,Guangxin Yang,Trokourey Albert,Cong Kong,Hui-Feng Wang
A highly sensitive modified gold (Au) electrode using cysteine-coated silver nanoparticles (Cys-AgNPs) is designed. The electrochemical activity of this designed sensor has exhibited an excellent response for the detection of 3-chloropropane-1,2-diol (3-MCPD). Indeed, the investigation of electrochemical behavior of 3-MCPD at the Cys-AgNPs/Au electrode has shown that the electrocatalytic activity for the 3-MCPD oxidation in NaOH solution is enhanced by three-fold with the presence of Cys-AgNPs film. This Cys-AgNPs film is found to be stable on the Au electrode and the developed electrode can be reused several times while obtaining excellent results. Furthermore, using differential pulse voltammetry technique, the oxidation current peak shows a linear relationship with 3-MCPD concentration between 2.5 ng/mL and 200 ng/mL. The calculated limit of detection (LOD) and limit of quantification (LOQ) are found to be 2.4 ng/mL and 8.6 ng/mL, respectively. A recovery rate ranging from 96% to 105% in the presence of interfering compounds with similar structure to 3-MCPD or not are observed for the determination of 3-MCPD. Moreover, the developed sensor is successfully applied to the determination of 3-MCPD in smoked mackerel and palm oil samples with results which show 3-MCPD concentration ranging from 174 to 439 μg/kg and 895 to 1280 μg/kg in smoked mackerel and palm oil samples, respectively. In addition to the reusability and stability of the electrode, these results suggest that this Cys-AgNPs/Au electrode can be used as an effective sensor to monitor and determine trace level of 3-MCPD in foodstuffs.
研究领域:
分析化学
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食品安全
·
电化学传感器
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产品关联
DOI
高影响因子
RAPID COMMUNICATIONS IN MASS SPECTROMETRY
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2021
·Vol. 35
·期 19
·e9169
·
IF 2.419
Zhang-Na Qin,Jun Ding,Qiong-Wei Yu,Ping Zhou,Yu-Qi Feng
Rationale 3-Monochloropropane-1,2-diol (3-MCPD) is a well-known contaminant formed in food thermal processing, which could be found in a variety of foodstuffs. Due to its potential carcinogenicity, it was essential to quickly develop a rapid and high-throughput analytical method to monitor 3-MCPD in foodstuffs, which is described in this study. Methods 3-MCPD was extracted from foodstuffs and then was derivatized with a boronic acid–modified C 60 (B-C 60 ) through the boronic acid-diol reaction. Microwave heating was used to accelerate the derivatization reaction. Mass spectrometry (MS) analysis was conducted using matrix-assisted laser desorption/ionization-MS (MALDI-MS). The application of the method was validated using various smoked food samples. Results The chemical derivatization of 3-MCPD with B-C 60 enabled the addition of a C 60 -tag to 3-MCPD. High-throughput analysis of the sample within 0.5 h was realized. A good linear range from 0.02 to 1.5 μg mL −1 for 3-MCPD was obtained, with a detection limit of 0.005 μg mL −1 . The recoveries in spiked foodstuffs ranged from 85.4% to 115.1% with relative standard deviations of 2.0%–14.2%. This method was successfully applied to detect 3-MCPD in smoked foodstuffs. Conclusions A quantitative method was developed for the detection of 3-MCPD in foodstuffs using B-C 60 derivatization combined with MALDI-MS strategy. This proposed method may serve as a potential platform for the rapid and high-throughput analysis of 3-MCPD in foodstuffs for the purpose of food safety control.
研究领域:
食品科学
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分析化学
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质谱分析
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF CHROMATOGRAPHY A
·
2025
·
IF 4
Bing Wang,Fuwei Xie,Mantang Chen,Pingping Shang,Lining Pan,Huapeng Cui,Yaqiong Qin,Li Zhang,Jizhao Guo,Xiaobing Zhang,Cong Nie,Xiaoyu Wang,Shaofeng Liu
Glycidol, 3-chloropropane-1,2-diol (3-MCPD), and 2-chloropropane-1,3-diol (2-MCPD), known as thermal processing contaminants, have been identified in heated tobacco product (HTP) aerosol, raising significant health concerns. Therefore, it is necessary to establish a quantitative analytical method for the release of them. In this study, ethyl acetate was used to extract the aerosol of HTP collected by Cambridge filter pad (CFP), the extract was derivatized with heptafluorobutyrylimidazole (HFBI), washed and dried before being analyzed by gas chromatography-mass spectrometry (GC-MS). The retention index and mass spectral characteristics of glycidol-HFBI derivative were characterized for the first time. The limits of quantification (LOQs) for glycidol, 3-MCPD and 2-MCPD were 58.32, 37.51 and 55.88 ng/cigarette respectively;the intra- and inter-day precision were less than 10% with recoveries ranging from 89% to 111%. The analysis results of eight domestic and foreign HTPs showed that: (1) The three target compounds were detected in all eight samples, indicating their widespread presence in HTP aerosol. (2) Significant variations in per-puff emission among samples suggested formulation and heating mode significantly impact glycidol and MCPDs release. (3) Glycidol and 3-MCPD were the major released substances, accounting for about 80% of the total three compounds emission. This study establishes a sensitive, reliable method for determining glycidol, 3-MCPD and 2-MCPD in HTP aerosol, providing critical technical support for health risk assessments.
研究领域:
分析化学
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环境卫生
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毒理学
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食品科学
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烟草科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
RENAL FAILURE
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2024
·
IF 3
Tao Wei,Bohan Liu,Yi Chen,Chang Li
3-monochloropropane-1,2-diol esters (3-MCPDE) are a group of contaminants which are mainly formed during heat processing of edible oil and fat-based foods. The kidney is the primary target organ for the toxic effects of 3-MCPDE. 3-MCPD-di-palmitate exists in a variety of oils and fats, and is the most common and relatively high proportion of 3-MCPDE. In this study, we investigated the protective effect of ascorbic acid on 3-MCPD-di-palmitate-induced renal injury in rats. Thirty 8-week-old male Sprague-Dawley rats were randomly divided into 5 groups, namely control, 3-MCPD-di-palmitate (240 mg/kg·bw), 3-MCPD-di-palmitate (240 mg/kg·bw) + ascorbic acid (100 mg/kg·bw), 3-MCPD-di-palmitate (240 mg/kg·bw) + ascorbic acid (200 mg/kg·bw) and 3-MCPD-di-palmitate (240 mg/kg·bw) + ascorbic acid (500 mg/kg·bw). These treatments were administered via gavage for a duration of 4 weeks. The effects of ascorbic acid on 3-MCPDE-induced kidney injury in rats were investigated by evaluating the kidney index, renal function (BUN, CRE), renal histopathology, oxidative stress markers (ROS, GSH, MDA, and T-AOC), DNA oxidation marker (8-OHdG), and activities of Caspase 3 and 9. The results showed that the exposure to 3-MCPDE significantly increased the kidney index, BUN and CRE levels, ROS and MDA levels, 8-OHdG levels, and activities of Caspase 3 and 9, while decreasing GSH and T-AOC. The combined treatment with 3-MCPDE and ascorbic acid can effectively restore the aforementioned parameters. The present study concluded that ascorbic acid effectively attenuates the renal apoptosis and oxidative homeostasis induced by 3-MCPDE uptake thereby intervening in renal injury.
研究领域:
毒理学
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药理学
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肾脏生理学
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氧化应激研究
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分子生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
MICROCHEMICAL JOURNAL
·
2024
·
IF 4.9
Xu Lu,Ming Li,Keqiang Bo,Bin Zheng,Xu Hun
A photoelectrochemical (PEC) assay strategy for the detection of matrix metalloproteinase-9 (MMP-9) was fabricated. RuSe 2 /CuO nanohybrids were first prepared by hydrothermal method. As a transition metal element semiconductor, RuSe 2 has excellent optical and electrical properties. By combining the excellent conductivity and adjustable bandgap of CuO, a binary heterojunction nanoflower with high photoelectric response was obtained. The combination of RuSe 2 and CuO reduces the electron hole recombination rate; the RuSe 2 /CuO nanohybrids exhibits a higher photocurrent response. In the MMP-9 PEC strategy determination, the magnetic beads (MB)-peptide-alkaline phosphatase (ALP) recognition probe was formed by modifying C-terminal of the peptide chain with biotin and binding to ALP, and the N-terminal was connected to carboxylated MB. When the target MMP-9 exists, the recognition probe, MB-Peptide-ALP, was recognized by MMP-9 to cut the substrate area and coding area and release ALP, catalyzing the hydrolysis of O-phosphonoxyphenol (OPP) to produce benzene-1,2-diol in situ, the photocurrent response was generated. This strategy provides lower background PEC noise for detecting MMP-9, with the advantage of simplicity and the sensitivity than conventional ELISA. The results showed that the recognition peptide probe PEC method achieved ultra-high sensitivity detection of target MMP-9, with a linear detection range of 1 pg/mL–100 ng/mL and a detection limit of 0.3 pg/mL (S/N = 3). The results of PEC assay strategy in human serum sample give the recoveries rate of 94.3 % to 108.1 % and relative standard deviation of 0.45–5.87 %.
研究领域:
纳米技术
·
生物化学
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分析化学
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医学诊断
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产品关联
DOI
高影响因子
Arabian Journal of Chemistry
·
2022
·
IF 6.212
Min Liang,Huixia Zhao,Suyi Dai,Chang Yu,Haijun Cheng,Weiguang Li,Fang Lai,Li Ma,Xiongmin Liu
1,3-Butadiene is the simplest conjugated diene, which is widely used in polymer materials, organic synthesis, and other fields. The investigation of its thermal stability and oxidation characteristics is necessary for production, transportation, and use safety. The pressure and temperature behavior of the autoxidation reaction of 1,3-butadiene with oxygen were determined using a custom-designed mini closed pressure vessel test (MCPVT). The effects of free radical initiators CHP and AIBN on the oxidation reaction were investigated. The thermal decomposition characteristics of oxidation products were measured by differential scanning calorimetry (DSC), and its hazards were discussed. The results showed that the oxidation reaction of 1,3-butadiene was easy to occur. Moreover, the activation energies of autoxidation, CHP-initiated oxidation, and AIBN-initiated oxidation reaction were 20.85 kJ·mol −1 , 33.30 kJ·mol −1 , and 56.27 kJ·mol −1 , respectively. In addition, the oxidation products were analyzed by headspace sampler-gas chromatography-mass spectrometry (HS-GC–MS), GC–MS, and iodometry. Some of 1,3-butadiene oxidation products under three conditions are the same, for example, 3-butene-1,2-diol, 4-vinylcyclohexene, 2(5H)-furanone, 2-propen-1-ol, and 2,6-cyclooctadien-1-ol. According to the reaction products, the oxidation reaction pathway of 1,3-butadiene was described. The research results are significant for avoiding fire and explosion accidents in the production, transportation, and application of 1,3-butadiene.
研究领域:
化学工程
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有机化学
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热分析
·
安全科学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）