CHINESE JOURNAL OF CHEMICAL ENGINEERING
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2023
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IF 3.8
Jinxiu Hu,Xianlong Liu,Yi Liu,Kang Xue,Chengxiang Shi,Xiangwen Zhang,Li Wang,Ji-Jun Zou,Lun Pan
High-energy-density fuels are important for volume-limited aerospace vehicles, but the increase of the fuel energy density always leads to poor cryogenic performance. Herein, we investigated the transposed Paternò-Büchi reaction of biomass cyclic ketone and cyclic alkene to synthesize the new kind of alkyl-substituted polycyclic hydrocarbon fuels with high energy density and good cryogenic performance. The triplet-energy-quenching results and phosphorescent emission spectra reveal the sensitization mechanism of the reaction, including photosensitizer excitation, triplet-triplet energy transfer, cyclization and relaxation, and the possible reaction path was revealed by the DFT calculations. The reaction conditions of photosensitizer type and addition, molar ratio of substrates, reaction temperature and incident light intensity were optimized, with the target product yield achieving 65.5%. Moreover, the reaction dynamics of the reaction rate versus the light intensity is established. After hydrogenation deoxygenation reaction, three fuels with high density of 0.864-0.938 g·ml −1 and low freezing point of <−55 °C are obtained. This work provides a benign and effective approach to synthesize high-performance fuels.
研究领域:
化学工程
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能源科学
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合成化学
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DOI
高影响因子
ANALYTICAL AND BIOANALYTICAL CHEMISTRY
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2024
·Vol. 416
·期 19
·4397-4407
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IF 3.8
Wang Yichun,Xia Yu
Plasmalogens are a special class of glycerophospholipids characterized by a vinyl ether bond (-C = C-O-) at the sn -1 position of the glycerol backbone. Altered plasmalogen profiles have been observed in neurodegenerative diseases and cancers. Profiling of plasmalogens requires specifying the vinyl ether bond and differentiating them from various types of isobars and isomers. Herein, by coupling C = C derivatization via offline Paternò–Büchi reaction with liquid chromatography-tandem mass spectrometry, we have developed a sensitive workflow for analysis of plasmalogens from biological samples. Using bovine heart lipid extract as a model system, we profiled more than 100 distinct structures of plasmenylethanolamines (PE-Ps) and plasmenylcholines (PC-Ps) at the C = C location level, far exceeding previous reports. Analysis of human glioma and normal brain tissue samples revealed elevated n-10 C = C isomers of PE-Ps in the glioma tissue samples. These findings suggest that the developed workflow holds potential in aiding the study of altered metabolism of plasmalogens in clinical samples. Graphical Abstract
研究领域:
生物化学
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医学
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分析化学
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PubMed
高影响因子
FOOD RESEARCH INTERNATIONAL
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2024
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IF 7
Chenyang Xu,Xiaohui Feng,Weihai Xing,Chaohua Tang,Xiaojie Sun,Youyou Yang,Junmin Zhang
Livestock and poultry meat is one of the main consumption sources of fatty acids (FAs) in China. FAs are the main component of lipids and essential nutrients for the human body. The location of carbon–carbon double bond (C C) in unsaturated fatty acids (UFAs) significantly affects the nutrition and flavor quality of meat products. This study established an analytical method for identifying the C C positions of UFAs based on the Paternò-Büchi (PB) reaction using ultra-high performance liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QTOF). The FA extract was derivatized with 2-acetylpyridine under ultraviolet light at 254 nm. The derivatized FA was then analyzed using targeted MS/MS mode in positive electrospray ionization. Limits of detection (LOD) and limits of quantitation (LOQ) of 21 UFAs were 0.004–0.680 and 0.013–2.267 μg/L, respectively. Furthermore, for the diagnostic ions at the same functional group terminal fragmented from derivatives of FA C C isomers, the abundance ratio was linear with that of the corresponding content, which could be applied to non-targeted screening of C C positions in FAs. Based on this method, a total of 28 UFAs were screened in five types of livestock and poultry meats in this study. Among them, four isomers of C17:1, four of C18:1, two of C18:2, two of C20:3 and two of C22:5 were identified. The precise identification and quantitation of the double bond positions of fatty acids will be of great significance for the exploration of the nutritional components in livestock and poultry meat.
研究领域:
食品科学
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营养学
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分析化学
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DOI
PubMed
高影响因子
Research
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2022
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IF 11.036
Hai-Fang Li,Jing Zhao,Wenbo Cao,Wenpeng Zhang,Yu Xia,Zheng Ouyang
Unraveling the complexity of the lipidome requires the development of novel approaches to facilitate structural identification and characterization of lipid species with isomer-level discrimination. Ultraviolet photodissociation tandem mass spectrometry (UVPD MS/MS) is a promising tool for structure determination of lipids. The sensitivity of UVPD for lipid analysis however is limited mainly due to weak absorption of UV photons by a C=C. Herein, a C=C site-specific derivatization, the Paternò-Büchi (PB) reaction, was used to incorporate a chromophore to the C=C moiety in fatty acyls, leading to significantly improved UVPD efficiency and sensitivity for pinpointing C=C locations. The wavelength-dependent photodissociation of the PB products demonstrated 4-CF3-benzophenone as the best reagent for UVPD in terms of the efficiency of generating C=C diagnostic fragments and simplicity for C=C location assignments. We demonstrated the effectiveness of this approach for the shotgun profiling of C=C location isomers in different lipid classes from complex lipid extracts, highlighting its potential to advancing the identification of the C=C bond locations in unsaturated lipids.
研究领域:
生物化学
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分析化学
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质谱技术
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DOI
高影响因子
TALANTA
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2021
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IF 6.057
Jian Zhang,Chengan Guo,Xinming Huo,Xiaoxiao Ma,Xin Li,Zeper Abliz,Yao Chu,Xiaohao Wang,Fei Tang
In recent years, the development of unsaturated lipid isomeric imaging based on the Paternò–Büchi (PB) reaction has improved significantly. However, research on this imaging method in ambient conditions needs to expand. In this paper, a method of PB reaction in the solid phase in ambient conditions is developed, which is combined with air-flow-assisted desorption electrospray ionisation mass spectrometry (AFADESI-MS) to achieve in situ imaging of lipids at an isomeric level. Experiments showed that the efficiency of the PB reaction was much higher when spraying the reagent solution than when sprinkling the reactant powder directly, and it was not lower than that in the liquid phase. This method can simplify the reaction conditions in the imaging process and can be applied to tissue section samples with only 10 min of pre-processing. The study successfully demonstrated the spatial distribution of unsaturated lipid isomers, and the isomeric ratio corresponded to the lesion areas in mouse brain cancer tissues. Due to its simple operation and performance in ambient conditions, this method may be useful for future studies on lipid isomers in tissues.
研究领域:
分析化学
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生物医学工程
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质谱学
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脂质组学
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DOI
PubMed
高影响因子
ANALYTICAL CHEMISTRY
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2023
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IF 7.4
Wenya Hu,Jialin Niu,Ruoning Bao,Chenglong Dong,Habtegabir Sara Girmay,Chunming Xu,Yehua Han
Petroleum olefins play important roles in various secondary processing procedures and are important feedstocks for the modern organic chemical industry. It is quite challenging to analyze petroleum olefins beyond the gas chromatography (GC)-able range using mass spectrometry (MS) due to the difficulty of soft ionization and the matrix complexity. In this work, a Paternò–Büchi (PB) reaction combined with atmospheric pressure chemical ionization and ultrahigh resolution mass spectrometry (APCI–UHRMS) was developed for selective analysis of olefins. Through the PB reaction, C═C bonds were transformed into four-membered rings of oxetane with improved polarity so that soft ionization of olefins could be achieved. The systematic optimization of PB reaction conditions, as well as MS ionization conditions, ensured a high reaction yield and a satisfied MS response. Furthermore, a sound scheme was set up to discriminate the coexisting unsaturated alkanes in complex petroleum, including linear olefins, nonlinear olefins, cycloalkanes, and aromatics, making use of their different behaviors during the PB reaction and chemical ionization. The developed strategy was successfully applied to the analysis of olefins in fluid catalytic cracking oil slurry, a complex heavy oil sample. This method extended the characterization of petroleum olefins from lower to higher with high efficiency and selectivity to provide a comprehensive molecular library for heavy petroleum samples and process optimization.
研究领域:
分析化学
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石油化学
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质谱
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产品关联
DOI
PubMed
高影响因子
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