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FOOD RESEARCH INTERNATIONAL · 2023 · IF 8.1

Machine learning based age-authentication assisted by chemo-kinetics: Case study of strong-flavor Chinese Baijiu

Qing-Ru Liu,Xiao-Juan Zhang,Lei Zheng,Lian-Jun Meng,Guang-Qian Liu,Ting Yang,Zhen-Ming Lu,Li-Juan Chai,Song-Tao Wang,Jin-Song Shi,Cai-Hong Shen,Zheng-Hong Xu

The aged Chinese liquor, Baijiu, is highly valued for its superior organoleptic qualities. However, since age-authentication method and aging-mechanism elucidation of Baijiu is still in the exploratory stage, high-quality aged Baijiu is often replaced by lower-quality, less-aged product with fraudulent mislabeling. Authentic high-quality strong-flavor Baijiu was analyzed by gas chromatography-mass spectrometry. Total esters decreased with aging, while acids, alcohols, aldehydes, ketones, terpenes, pyrazines increased. Although concentrations of partial compounds showed non-monotonic profiling during aging, a close positive linear correlation (R 2  = 0.7012) of Baijiu Evenness index (0.55–0.59) with aging time was observed, indicating a more balanced composition in aged Baijiu. The reaction quotient (Qc) of each esterification, calculated by the corresponding reactant and product concentration, approached to the corresponding thermodynamic equilibrium constant Kc. This result demonstrated that the spontaneous transformation driven by thermodynamics explained part of the aging compositional profiling. Furthermore, an aging-related feature selection and an age-authentication method were established based on three models combined with five ranking algorithms. Forty-one key features, including thirty-six compound concentrations, four esterification Qc values and the Evenness index were selected out. The age-authentication based on neural network using forty-one input features accurately predicted the age group of Baijiu samples (F1 = 100 %). These findings have deepened understanding of the Baijiu aging mechanism and provided a novel, effective approach for age-authentication of Baijiu and other liquors.

研究领域: 食品科学 · 化学 · 人工智能
✓ 已验证 DOI PubMed 高影响因子
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MOLECULES · 2023 ·Vol. 28 ·期 9 ·3948 · IF 4.6

Highly Efficient Synthesis of Chlorogenic Acid Oleyl Alcohol Ester under Non-Catalytic and Solvent-Free Conditions

Cong Sun,Hui Liu,Yanran Chen,Xianzhi Wei,Shaohua Liang

As a natural polyphenolic compound, chlorogenic acid (CGA) has attracted increasing attention for its various biological activities, such as antioxidant, liver protection, intestinal barrier protection, and effective treatment of obesity and type II diabetes. However, the poor solubility of CGA in hydrophobic media limits its application in the food, drug and cosmetic industries. In order to obtain new hydrophobic derivatives, a highly efficient synthesis approach of CGA oleyl alcohol ester (CGOA) under non-catalytic and solvent-free conditions was developed in this study. The influences of reaction temperature, reaction time, substrate molar ratio, and stirring rate on the CGA conversion were investigated. The results showed that the optimal conditions were as follows: reaction temperature 200 °C, reaction time 3 h, molar ratio of CGA to oleyl alcohol 1:20, and stirring rate 200 rpm. Under these conditions, the CGA conversion could reach 93.59%. Then, the obtained crude product was purified by solvent extraction and column chromatography, and the purify of CGOA was improved to 98.72%. Finally, the structure of CGOA was identified by FT-IR, HPLC-MS and NMR. This study provides a simple and efficient strategy for the preparation of CGOA with the avoidance of catalysts and solvents.Keywords:chlorogenic acid;chlorogenic acid oleyl alcohol ester;esterification;non-catalytic synthesis

CAS / MDL: 7553-56-2 143-28-2
研究领域: 食品科学 · 药物化学 · 天然产物化学
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FUEL · 2025 · IF 7.5

Adjustable Brønsted type ionic liquid catalyst based on porous cellulose microspheres for green and efficient catalytic system in transesterification

Tao Wang,Xiqing Wang,Tianshu Liu,Yujie Fu

Realizing high catalytic efficiency and stability always be the core guiding principle and continuous optimization in industrial production. Fatty Acid Methyl Esters (FAMEs) are a key component of biodiesel, serving as a renewable, environmentally friendly alternative to conventional petroleum-based diesel fuel. In this study, a series of novel Brønsted acidic cellulose-based ionic liquids (PCM-ILs) were successfully prepared using cellulose as the raw material through chemical grafting and ionic bonding. These PCM-ILs were first applied to catalyze the transesterification of Pistacia chinensis Bunge seed oil for FAMEs production. PCM-ILs can be tailored by varying anions. Under optimal conditions—methanol/oil ratio (10:1), catalyst (10 wt%), temperature (80 °C), and time (6 h)—the FAME yield reached 98.6 %. In addition, the conversion yield remained above 85 % after the prepared catalyst be recycled for six times. Thus, the development of this straightforward and economically viable cellulose-based assembly opens up innovative avenues for the design of high-performance biocatalysts suitable for industrial applications.

研究领域: 化学工程 · 可再生资源技术 · 绿色化学
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Catalysts · 2024 ·Vol. 14 ·期 2 ·142 · IF 3.8

The Green Synthesis of Biodiesel via Esterification in Water Catalyzed by the Phosphotungstic Acid–Functionalized Hydrophobic MCM–41 Catalyst

Dengke Li,Qinghao Shi,Fengbing Liang,Dexin Feng

Biodiesel is a non-toxic and environmentally friendly fuel that is made from renewable biological sources. It can replace petrochemical diesel and has very broad application prospects. However, the main raw materials in biodiesel are animal and plant oils, which present the problems of high costs and a lack of resources. The current research primarily emphasizes the transesterification process, with comparatively less focus on the esterification of fatty acids. In this paper, a series of phosphotungstic acid (PTA)-functionalized hydrophobic MCM–41 catalysts, OTS–PTA–MCM–41(Cx), were synthesized and used to catalyze the esterification of long-chain fatty acids with methanol in water. The experimental results show that the yield of esterification reached a maximum when catalyzed by OTS–PTA–MCM–41(Cx) and synthesized with a template agent with two carbon atoms less than the number of carbon atoms of a fatty acid. The effects of different reaction variables were investigated to optimize the reaction conditions for the maximum conversion. The stability of the catalyst was also verified. Finally, a mixed catalyst was used to catalyze in situ the esterification of fatty acids in a fermentation broth, which reached a high level (close to 90%). This paper provides references for the synthesis of a hydrophobic solid acid catalyst and green synthesis by esterification reactions in an aqueous solution and a fermentation broth system.

研究领域: 化学工程 · 环境科学
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JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY · 2011 ·Vol. 89 ·期 4 ·705-711 · IF 1.587

Synthesis of Trimethylolpropane Esters of Oleic Acid Using a Multi-SO3H-Functionalized Ionic Liquid as an Efficient Catalyst

Li Rui-Jun,Chen Li,Yan Zong-Cheng

Biodegradable trimethylolpropane triesters of oleic acid were synthesized by esterification of trimethylolpropane and oleic acid over a multi-SO 3 H-functionalized strong Brønsted acidic ionic liquid as the catalyst. The results showed that the esterification can proceed satisfactorily over the catalyst at an ambient pressure even without simultaneous removal of water. Under the optimal reaction conditions (temperature: 100 °C, reaction time: 3 h, reactant molar ratio: 3.6:1, and catalyst amount, high conversion rate of trimethylolpropane (99.0%) and selectivity of trimethylolpropane triester (92.1%) were obtained. The ionic liquid was reused six times after the removal of water and no obvious change in catalytic activity was detected. Operational simplicity, high yields along with good reusability makes the multi-SO 3 H-functionalized ionic liquid a promising catalyst for the esterification of trimethylolpropane with oleic acid.

研究领域: 化学工程 · 绿色化学
✓ 已验证 DOI 高影响因子
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Journal of Food Measurement and Characterization · 2021 ·Vol. 15 ·期 6 ·5345-5359 · IF 2.431

Effects of electrostatic field treatment on the maturation characteristics of rum and its mechanism

Zhang Mingjun,Chen Yu,Wei Qunshu,Li Jianbin

The effect of applying an electrostatic field treatment to rum and its underlying reaction mechanism based upon a model system were investigated in this study. A field intensity of 1 kV·cm −1 and processing time of 30 min were the optimal treatment conditions, the content of (desirable) ester was increased to 219.57 ± 4.61 μg·mL −1 , and the content of (undesirable) fusel oil was decreased to 643.37 ± 15.26 μg·mL −1 , compared with the control (208.42 ± 2.31 μg·mL −1 and 707.04 ± 2.21 μg·mL −1 , respectively). In addition, Odorant Activity Value (OAV) analysis showed that there were 15 main flavor components (OAV  > 1) in rum, and the concentrations of 13 flavor components were increased after 1 kV·cm −1 electrostatic field treatment, indicating that the flavor quality of rum was improved. When the electrostatic field intensity was 0.5, 1, and 2 kV·cm −1 , the rate constant (k) of the esterification reaction increased in the ethanol-acetic acid model system, and the activation energy decreased from 47.7 kJ·mol −1 to 46.1, 40.6 and 38.6 kJ·mol −1 , respectively. This showed that the electrostatic field treatment was helpful to the esterification reaction in the rum simulation system. 1 H NMR results showed that δET-OH, δH-OH, δCH 3 , and δCH 3 in the ethanol–water model system were all increased when the electrostatic field strength was 0.5, 1, 2, and 4, respectively. This showed that the electrostatic field treatment promoted the hydrogen bond association between ethanol and water molecules in the rum simulation system. Therefore, the maturation process in rum was accelerated and the quality of the rum was improved by electrostatic field treatment.

研究领域: 食品科学 · 化学工程
✓ 已验证 DOI 高影响因子
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APPLIED ORGANOMETALLIC CHEMISTRY · 2024 ·Vol. 38 ·期 6 ·e7504 · IF 3.7

In situ impregnation of cobalt-doped tungstophosphoric acid on MOF-801 toward enhanced catalytic activity for esterification

Qiuyun Zhang,Mengmeng Hu,Fan Chen,Jiao Lei,Jingsong Cheng,Juan Ma,Yongting Zhao,Yutao Zhang

Development of an energy-efficient and economical route is necessary for society to synthesize green biofuels. Herein, cobalt-doped tungstophosphoric acid (Co-HPW) is in-situ impregnated in the Zr-based metal–organic framework (MOF-801) forming composite of Co-HPW/MOF-801. The chemical composition, morphology, and acidic sites of the Co-HPW/MOF-801 composite were analyzed through x-ray diffractometer (XRD), Fourier transform infrared (FTIR), scanning electron microscope (SEM), energy-dispersive x-ray spectroscopy (EDS), thermogravimetric analysis (TG), N 2 physisorption, ammonia temperature-programmed desorption (NH 3 -TPD), pyridine-adsorbed infrared spectra (Py-FTIR), and x-ray photoelectron spectroscopy (XPS). The catalytic performance of the as-synthesized catalyst was explored to catalyze esterification of lauric acid (LA) with methanol. The outcomes revealed that the Co-HPW/MOF-801 nanocatalyst achieved a high conversion of 86.3% under the optimized reaction condition (catalyst amount of 0.15 g, temperature of 100°C, time of 4 h, and methanol/LA molar ratio of 20:1). The excellent catalytical performance is mainly due to the large BET surface area, exposure of more active centers from available pore structure, and simultaneous possession of high Lewis and Brønsted acidity. Furthermore, the kinetic study revealed that the reaction process was kinetically controlled and the activation energy was found to be 42.1 kJ/mol. The results suggest that the synthesized Co-HPW/MOF-801 nanocatalyst is an environmental greenness, low cost, and suitable for easy scale-up for the production of biofuels.

研究领域: 材料科学 · 催化化学 · 能源化学
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CANADIAN JOURNAL OF CHEMICAL ENGINEERING · 2024 · IF 1.6

Structural modulation of ionic liquids as efficient catalysts for esterification reaction

Ping Xie,Tianhao Zhong,Tao Li,Yiwu Lu,Yingmin Yu,Qingshan Zhao,Zhongtao Li

There is an urgent need to develop green catalytic transesterification technology to reduce liquid waste and instrument corrosion. Ionic liquids with controlled activity, easy recovery, and corrosion resistance have great potential as catalysts for transesterification reactions. In this paper, a series of ionic liquids were prepared using imidazole and ammonium compounds as cations, and sulphuric acid, p -toluenesulfonate, and bistrifluoromethanesulfonate anions as anions. In comparison, the ionic liquid made from imidazole with H 2 SO 4 (IMIHS) was found to be the best catalyst for the esterification reaction with high speed, high activity, low corrosion, and high stability, and its catalytic performance was superior to that of sulphuric acid. The optimum reaction conditions were as follows: the molar ratio of ethanol to acetic acid was 1:1, the catalyst amount was 5 wt.%, the reaction temperature was 80°C, and the reaction time was 120 min. The maximum yield of ethyl acetate was 66.2% under the optimum reaction conditions. The catalytic activity was not declined obviously by reusing six times. The activation energy of the reaction is 48.748 kJ/mol.

研究领域: 化学工程 · 催化科学
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Industrial Chemistry & Materials · 2022 ·Vol. 1 ·期 1 ·106-116 · IF 0

Hierarchically ordered porous carbon with atomically dispersed cobalt for oxidative esterification of furfural

Wen Yao,Chenghong Hu,Yajie Zhang,Hao Li,Fengliang Wang,Kui Shen,Liyu Chen,Yingwei Li

Nitrogen-rich zeolitic imidazolate frameworks (ZIFs) are ideal precursors for the synthesis of metal single atoms anchored on N-doped carbon. However, the microporous structures of conventional ZIFs lead to low mass transfer efficiency and low metal utilization of their derivatives. Here, we construct a composite of Co single atoms anchored on nitrogen-doped carbon with a three-dimensional ordered macroporous structure (Co-SA/3DOM-NC) by two-step pyrolysis of ordered macro/microporous ZnCo-ZIF. Co-SA/3DOM-NC shows high activity in the oxidative esterification of furfural, achieving a 99% yield of methyl 2-furoate under mild reaction conditions, which is significantly superior to the microporous and the Co-nanoparticle counterparts. The high activity of Co-SA/3DOM-NC should be attributed to the CoN4 centers with high intrinsic activity and the ordered macroporous structure, promoting the mass transfer of reactants and accessibility of active sites. Keywords: Heterogeneous catalysis; Hierarchical pores; Ordered macropore; Oxidative esterification reaction; Single-atom catalysts.

研究领域: 化学工程 · 材料科学
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FUEL PROCESSING TECHNOLOGY · 2016 · IF 3.847

Catalytic upgrading of bio-oil by simultaneous esterification and alkylation with azeotropic water removal

Junxiang Lu,Shujun Guo,Yan Fu,Jie Chang

Due to the negative effects of acids and aldehydes, crude bio-oil has to be upgraded before its application as a high-graded fuel. A novel method for bio-oil upgrading by simultaneous catalytic esterification and alkylation with azeotropic water removal using n-butanol and 2-methylfuran was investigated in this work. Under the optimum upgrading conditions, water content was evidently decreased from 27.82% to 3.21%, and acid number was reduced from 41.12   mg NaOH/g to 6.17   mg NaOH/g. High heating value of upgraded bio-oil was more than 2 times higher than crude bio-oil and the other properties were also improved significantly. GC-MS analysis indicated that labile acids, aldehydes, ketones and lower alcohols were transformed to stable target products. The introduction of 2-methylfuran effectively suppressed acetalization reactions and the yields of more stable alkylation products were higher than acetals. In addition, oxygenated liquid fuel and sugars and their derivatives could be effectively separated from upgraded bio-oil by H 2 O/CH 2 Cl 2 extraction. The main product in crude sugars part was butyl-β-D-glucopyranoside, which was formed by means of hydrolysis of levoglucosan and the following glycosidation.

研究领域: 能源生物学 · 催化化学
✓ 已验证 DOI 高影响因子
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2022 · IF 5.518

Synthesis of sinapic acid modified sodium hyaluronate particles and the one-step processing of multiple Pickering emulsion

Wenxiu Liu,Lin Ding,Jiawen Xu,Yazhuo Shang,Zejian Wang,Honglai Liu

In this study, a series of sodium hyaluronate (HA) polymer molecules grafted with different amounts of sinapic acid (SA) groups were synthesized by adjusting the esterification reaction time, and the introduction of SA endows the polymer with both amphipathy and UV absorbability. The amphipathic polymer molecules (HA-SA) tend to self-assemble into polydisperse colloid particles and the particle properties of HA-SA, such as particle size, zeta potential as well as the interfacial activity were studied in detail. The results indicate that the properties of HA-SA particles prepared with different esterification reaction time are quite different due to the different graft amounts of SA. The graft amount of SA increased with the prolongation of esterification reaction time, and the interfacial activity of the obtained HA-SA particles also increased gradually, but an excessively high graft amount would make the polymer too hydrophobic and thus lead to the interfacial activity reduce slightly. By controlling the esterification reaction time within an appropriate range, the prepared particles show significant interfacial activity and are apt to linger on the interface of oil-water to reduce the interfacial tension, which has potential to be a new promising stabilizer of emulsions. Further studies show that, benefiting from the polydispersity of the HA-SA particles, the water-in-oil-in-water (W/O/W) multiple Pickering emulsion can be prepared by one-step homogenization using HA-SA particles as stabilizer. Different from the inorganic particle emulsifiers and their stabilized Pickering emulsions, the particles that self-assembled by HA-SA amphiphilic polymers and their stabilized Pickering emulsions have obvious sensitivity to pH and temperature due to the existence of both COO - and OH - in HA molecule, which provides a new strategy for developing stimulus-responsive Pickering emulsifiers. The excellent moisture retention of HA and the protection of SA against UV radiation make HA-SA particles potentially a high-end cosmetic emulsifier accompanied with moisturizing and sunscreen effects on skin.

研究领域: 材料科学 · 化妆品科学 · 界面化学
✓ 已验证 DOI 高影响因子
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CATALYSIS TODAY · 2019 · IF 4.888

Ionic liquid [BMIm][HSO4] as dual catalyst-solvent for the esterification of hexanoic acid with n-butanol

Qian Zeng,Zhen Song,Hao Qin,Hongye Cheng,Lifang Chen,Ming Pan,Yi Heng,Zhiwen Qi

Butyl hexanoate (BuHE) is currently synthesized through the Fischer esterification with mineral acid as catalyst, which suffers from the problems of side reaction, difficult recycling, and corrosion. To overcome these disadvantages, ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate ([BMIm][HSO 4 ]) is employed as dual catalyst-solvent for the esterification of hexanoic acid (HeAc) with n-butanol (BuOH) in a reactive extraction process. The dual functions of [BMIm][HSO 4 ], extraction and catalysis, were confirmed by liquid-liquid equilibria for the two systems {[BMIm][HSO 4 ] + HeAc + BuHE} and {[BMIm][HSO 4 ] + BuOH + BuHE}, and by the comparison of esterifications with or without [BMIm][HSO 4 ], respectively. Moreover, the optimal reactive extraction conditions for BuHE formation were obtained. Finally, the possible mechanism of intensification of [BMIm][HSO 4 ] on BuHE formation in reactive extraction process was proposed.

CAS / MDL: 71-36-3 142-62-1
研究领域: 化学工程 · 催化科学
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