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eFood · 2022 · IF 0

Pectin with various degrees of esterification differentially alters gut microbiota and metabolome of healthy adults

Wenqi Huang,Qingying Fang,Linlin Fan,Tao Hong,Huizi Tan,Shaoping Nie

Pectin with various degrees of esterification (DE) leads to different food processing directions and has the distinct potential for modulating human health. Investigations of pectin–gut microbiota interactions may contribute towards better understanding of the structure–function mechanism. In this study, in vitro batch fermentation (artificial colon model) was used to illustrate the differential impacts of pectin with different DE on the gut microbiota and metabolome of healthy adults. The results indicated that low-esterified pectin L13 showed better-sustained abilities in terms of the diversity of microbiota and promoted the abundance of Clostridiaceae and Lachnospiraceae at family levels, and Bacteroides and Lachnospira at genus levels. High-esterified pectin H121 induced less Enterococcus and Clostridium . Data from untargeted metabolomics revealed the alterations of intracellular metabolites including fatty acids, amino acids, and organic molecules by various types of pectins. Inositol was the unique intracellular metabolite that was significantly upregulated by low-esterified pectin L13. All types of pectins could increase the level of acetic acid, but butyric acid was only enriched by pectin L13.

研究领域: 食品科学 · 微生物学 · 代谢组学
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RENEWABLE ENERGY · 2021 · IF 8.001

Direct production of biodiesel via simultaneous esterification and transesterification of renewable oils using calcined blast furnace dust

Yi-Tong Wang,Wen-Jie Cong,Ya-Nan Zeng,Yu-Qing Zhang,Jing-Long Liang,Jun-Guo Li,Li-Qun Jiang,Zhen Fang

Direct production of biodiesel by both esterification and transesterification of renewable oils with acid value (AV) of 9.6–28.9 mg KOH/g using calcined blast furnace dust is studied. Blast furnace dust calcined at 600–700 °C obviously promotes efficient biodiesel production because of the crystal form transformation from lead sulfate particles in dust into active lead oxide, lead sulfide, and lead particles. It is found for the first time that lead oxide, lead sulfide and lead particles can resist saponification from fatty acids to catalyze raw renewable oils to biodiesel with catalytic activity order as follows: lead oxide > lead > lead sulfide > lead sulfate. Biodiesel production process is optimized according to an orthogonal design with biodiesel yield of 92 wt% obtained at AV of 9.6 mg KOH/g (82 wt% after 5 cycles). Biodiesel yield of 84 wt% is achieved at AV of 28.9 mg KOH/g with acidity of 0.18 mmol/g. Calcined blast furnace dust presents potential applications in the production of biodiesel from renewable oils with high AVs.

研究领域: 化学工程 · 可再生能源 · 催化材料
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TETRAHEDRON · 2015 · IF 2.641

Copper-catalyzed direct esterification of P(O)–OH compounds with phenols

Biquan Xiong,Kui Zeng,Shanshan Zhang,Yongbo Zhou,Chak-Tong Au,Shuang-Feng Yin

A novel copper-catalyzed method for the direct esterification of P(O)–OH compounds using phenols as efficient esterification reagents is illustrated. It is a simple way to generate a broad spectrum of functionalized O -aryl phosphinates , phosphonates , and phosphates from basic starting materials with moderate to excellent yields.

CAS / MDL: 7440-50-8 108-95-2
研究领域: 有机化学 · 合成化学
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ACS Sustainable Chemistry & Engineering · 2019 · IF 6.97

Carbon Nanoparticle-Stabilized Pickering Emulsion as a Sustainable and High-Performance Interfacial Catalysis Platform for Enzymatic Esterification/Transesterification

Zhe Dong,Zengshe Liu,Jie Shi,Hu Tang,Xia Xiang,Fenghong Huang,Mingming Zheng

A sustainable and efficient reaction system for enzymatic oil modification is imperative for the food industry. Given the interfacial activation effect of lipase, the sufficient oil–water interface is vital for excellent catalytic activity of lipase. In the present study, a Pickering emulsion reaction system was prepared through directly using reactants as the oil phase and stabilized by mesoporous carbon spheres (MCS) after immobilization of lipase AYS (Candida rugosa, lipase@MCS). Lipase@MCS worked as both the emulsifier and catalyst. Each droplet in the Pickering emulsion was regarded as a microreactor with the reactants in the oil phase, and the removal of the product H2O “pushed” the reaction forward. Taking advantage of the adequate oil–water interface for “lid” opening of lipase and rapid mass transfer in MCS, the Pickering emulsion exhibited excellent enzymatic activity toward phytosterol esterification and transesterification, achieving 95.0% conversion after 1.5 h and catalytic efficiency (CE) of 6.8 mmol g–1 h–1 under nonequilibrium conditions. It is the best performance reported currently with the shortest reaction time, minimal amount of catalyst, and the highest CE (19-fold higher than free lipase one-phase reaction system). Immobilization of lipase on the MCS not only endowed the lipase with exceptional recyclability but also afforded a shield to protect the enzyme from deactivation in a harsh environment, as evidenced by the thermotolerance and recycling test results. This paper paves the way to advancing progress in enzyme-immobilized Pickering emulsion as a sustainable and high-efficiency platform for biocatalysis application.

CAS / MDL: 3326-32-7
研究领域: 生物化学 · 食品科学 · 材料科学
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EUROPEAN JOURNAL OF INORGANIC CHEMISTRY · 2018 ·Vol. 2018 ·期 41 ·4579-4585 · IF 2.507

Exploration of Intrinsic Lipase-Like Activity of Zirconium-Based Metal-Organic Frameworks

Xiao Liu,Wei Qi,Yuefei Wang,Rongxin Su,Zhimin He

Graphical We demonstrated that UiO-66 and its derivatives possess efficiently intrinsic lipase-like activity, catalyzing ester hydrolysis, transesterification and even the esterification reaction. It's –NH 2 functionalized analogue UiO-66(NH 2 ) exhibited the highest catalytic activity due to the synergistic catalytic effect. To overcome the disadvantages of natural enzymes, artificial enzyme mimics attracted increasing attention of researchers. Metal-organic frameworks (MOFs) are expected as one of the most appropriate candidates for artificial enzyme mimics. In this work, we demonstrate that the zirconium-based MOF material UiO-66 and its analogues possess intrinsic lipase-like activity and can efficiently catalyze ester hydrolysis, transesterification and esterification reactions. Furthermore, the UiO-66(NH 2 ) exhibits much higher catalytic activity than that of UiO-66, which can be attributed to the synergy effect between the zirconium cluster centres and the amino moieties during the catalytic cycle.

研究领域: 生物化学 · 材料科学
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Membranes · 2022 ·Vol. 12 ·期 12 ·1269 · IF 4.562

Improved Esterification of Citric Acid and n-Butanol Using a Dense and Acid-Resistant Beta Zeolite Membrane

Zhengquan Yang,Mingyu Peng,Yu Li,Xiaowei Wu,Tian Gui,Yuqin Li,Fei Zhang,Xiangshu Chen,Hidetoshi Kita

In this work, a dense and acid-resistant beta zeolite membrane was applied to improve the esterification of citric acid and n-butanol, for the first time. Through the continuous removal of the by-product water via pervaporation (PV), the conversion of citric acid was significantly enhanced from 71.7% to 99.2% using p-Toluenesulfonic acid (PTSA) as catalyst. PTSA was a well-known strong acid, and the membrane kept almost no change after PV-esterification, indicating the superior acid resistance of beta zeolite membrane. Compared to the use of acid-resistant MOR zeolite membrane by PV-esterification, a consistently higher conversion of citric acid was obtained using a high-flux beta zeolite membrane. The results showed that high water permeation on the beta zeolite membrane, with good acid resistance, had a strong promoting effect on esterification, leading to an improved conversion. In addition, the citric acid conversion of 97.7% could still be achieved by PV-esterification at a low reaction temperature of 388 K.Keywords:improved esterification;Tributyl citrate;beta zeolite membrane;PV-esterification;high conversion

研究领域: 化学工程 · 材料科学
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JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY · 2015 ·Vol. 92 ·期 4 ·495-502 · IF 1.541

Biodiesel Production Using a Carbon Solid Acid Catalyst Derived from β-Cyclodextrin

Fu Xiao-bo,Chen Jie,Song Xue-li,Zhang Yuan-ming,Zhu Yi,Yang Jun,Zhang Cheng-wu

A novel carbon solid acid catalyst was prepared by incomplete hydrothermal carbonization of β-cyclodextrin into small polycyclic aromatic carbon sheets, followed by the introduction of –SO 3 H groups via sulfonation with sulfuric acid. The physical and chemical properties of the catalyst were characterized in detail. The catalyst simultaneously catalyzed esterification and transesterification reactions to produce biodiesel from high free fatty acid (FFA) containing oils (55.2 %). For the as-prepared catalyst, 90.82 % of the oleic acid was esterified after 8 h, while the total transesterification yield of high FFA containing oils reached 79.98 % after 12 h. By contrast, the obtained catalyst showed comparable activity to biomass (such as sugar, starch, etc.)-based carbon solid acid catalyst while Amberlyst-15 resulted in significantly lower levels of conversion, demonstrating its relatively high catalytic activity for simultaneous esterification and transesterification. Moreover, as the catalyst can be regenerated, it has the potential for use in biodiesel production from oils with a high FFA content.

CAS / MDL: 7585-39-9
研究领域: 化学工程 · 可再生能源
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BIORESOURCE TECHNOLOGY · 2014 · IF 5.039

Lewis acid-catalyzed in situ transesterification/esterification of microalgae in supercritical ethanol

Binbin Jin,Peigao Duan,Yuping Xu,Bing Wang,Feng Wang,Lei Zhang

The activities of several Lewis acid catalysts such SnCl 2 , FeCl 3 , ZnCl 2 , AlCl 3 , and NbCl 5 for the in situ transesterification/esterification of lipid contained within a microalga ( Chlorella pyrenoidosa ) in ethanol at 350   °C were examined to identify the most suitable catalyst in term of crude biodiesel (CBD) yield. Of those catalysts tested, ZnCl 2 showed the highest performance toward the CBD production. Using ZnCl 2 as catalyst, effects of reaction temperature (200–370   °C), time (0–120   min), ethanol to microalga ratio (EtOH:MA) (5/5–40/5), catalyst loading (0–30   wt.%), and algae moisture (0–80   wt.%) on the yields of product fractions and the properties of CBD were studied. The presence of ZnCl 2 not only promoted the production of CBD but also showed activities toward the deoxygenation and denitrogenation of CBD. The moisture content in the starting material is the most influential factor affecting the yield and properties of CBD.

研究领域: 生物化学 · 可再生能源 · 催化化学
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Molecular Catalysis · 2024 · IF 3.9

Efficient cascade reactions involving esterification, hydrogen transfer, and lactonization for biomass conversion using MOF/Metal oxide composites as heterogeneous catalysts

Lizhen Qin,Jingying Wang,Huihui Mao,Lvjie Ge,Chao Yao

Development of heterogeneous catalysts with both Brønsted and Lewis acid properties has proved to be promising and useful because they offer an efficient way to cascade reactions. In this study, we present the synthesis pathway and efficacy evaluation of new composites which combined by sulfonic acid functional group modified TiO 2 and MIL-101, analyzing their structure-performance correlation as heterogeneous catalysts in cascade reactions involving esterification, hydrogen transfer, and lactonization. These composites possess an open porous structure (MOF and porous TiO 2 ), as well as active sites including Lewis acid (unsaturated coordination metal), Lewis base (Ti-OH), and Brønsted acid (-SO 3 H). The role of these active sites and the synergies between them were investigated through the esterification of levulinic acid and the direct synthesis of γ-valerolactone from levulinic acid and furfural under cascade reactions. The composites exhibit a 100% ethyl levulinate (EL) yield at 120°C for 6 hours, with γ-valerolactone yields reaching up to 94.5% (160 °C, 9 h) and 89.5% (160 °C, 16 h) from levulinic acid and furfural, respectively. This synergistic effect of Lewis acid/base and Brønsted acid ensures efficient esterification. The presence of a sulfonic acid group promotes the lactonization reaction, while the Meerwein-Ponndorf-Verley reduction is facilitated by the dual Cr sites located adjacent to each other in the secondary building unit of MIL-101(Cr). Moreover, the double-porous structure of porous TiO 2 and MIL-101(Cr) effectively guarantees the efficient mass transfer of reactants and intermediates, leading to enhanced synergistic effects that promote more efficient reaction conversion.

CAS / MDL: 7789-02-8 100-21-0
研究领域: 化学工程 · 催化科学
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FUEL · 2022 · IF 8.035

Ionic liquid grafted NH2-UiO-66 as heterogeneous solid acid catalyst for biodiesel production

Ping Lu,Huaifang Li,Mantian Li,Jie Chen,Changshen Ye,Hongxing Wang,Ting Qiu

In this work, acidic ionic liquid (AIL) was grafted into NH 2 -UiO-66 through acid-base interaction. And the novel heterogeneous catalyst x AIL@NH 2 -UiO-66 ( x means the mass ratio of AIL to NH 2 -UiO-66) was first applied in the field of biodiesel production. The optimal catalyst 3AIL@NH 2 -UiO-66 with good wettability (with reactants) and high acidity was prepared successfully. Accordingly, the 3AIL@NH 2 -UiO-66 can be widely applied in biodiesel production from different raw materials. The conversion of free fatty acids (FFAs) in esterification was above 90%, as well as the biodiesel yield in transesterification was above 80%, showing excellent catalytic activities of 3AIL@NH 2 -UiO-66. And the 3AIL@NH 2 -UiO-66 also revealed excellent reusability, with the conversion of oleic acid decreases from 96.86% to 90.42% after 6 runs. In addition, the interaction between any two of the three factors (catalyst dosage, reaction time and molar ratio) on the oleic acid conversion was revealed with 3D response surface technology. By the mechanism investigation, the good wettability with reactants and high acidity of the catalysts are identified as key factors for biodiesel production. The method of anchoring ionic liquids with organic linkers for the application of MOFs in biodiesel production offers abundant possibilities.

研究领域: 化学工程 · 催化材料 · 可再生能源
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FUEL · 2019 · IF 5.128

Lewis acid-catalyzed in situ transesterification/esterification of tigernut in sub/supercritical ethanol: An optimization study

Ye Tian,Feng Wang,Long-Fei Xie,Yu-Ping Xu,Pei-Gao Duan

Lewis acid-catalyzed in situ transesterification/esterification of tigernut ( Cyperus esculentus ) was conducted in sub/supercritical ethanol. An L 16 (4 4 ) orthogonal design with four factors at four levels was employed to investigate the influence of the process variables on the product distribution and the composition of crude biodiesel (CBD). The four factors were temperature (230–290 °C), time (0–90 min), ethanol to feedstock ratio (E/F) (4/3–16/3 mL/g), and catalyst type (ZnCl 2 , FeCl 3 , SnCl 2 , and H 3 PO 4 ). The results showed that the catalyst type and E/F ratio were the two most influential variables affecting the yield and composition of the CBD. Of the Lewis acids tested, SnCl 2 showed the highest performance in terms of the CBD yield and its esters content. Increasing the E/F ratio essentially led to a higher CBD yield and higher ester content of the CBD. A higher temperature and longer reaction time resulted in an obvious increase in the gas yield but had no significant effect on the yield and quality of the CBD. The produced CBDs had extremely low N and S contents (0.2–0.6 wt% and less than 0.1 wt%, respectively) and were abundant in fatty acid esters (∼70%), mainly ethyl oleate and ethyl palmitate, making it more suitable for subsequent biofuel production.

研究领域: 生物能源 · 化学工程 · 植物学
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POLYMER BULLETIN · 2019 ·Vol. 77 ·期 6 ·2873-2887 · IF 1.858

A comparative analysis of the preparation of cellulose acetate butyrate and the characteristics of applying in pearlescent coating film

Huang Aimin,Wei Liping,Zhao Zengyan,Wei Guodong,Zhang Yanjuan,Huang Zuqiang,Li Xuanhai,Hu Huayu,Qin Xingzhen,Yang Mei

A simple, green, and efficient mechanical activation-assisted esterification (MAE) technology was developed for the preparation of cellulose acetate butyrate (CAB), which was used as film-former for pearlescent coating. In addition, CAB was also prepared by a traditional liquid phase esterification (LPE) method for comparing the structures and characteristics of the CABs prepared by these two technologies. 1 H and 13 C NMR confirmed that CAB was successfully produced, and the degree of substitution of acetyl and butyryl groups was also calculated. The crystal structure and molar mass of the CABs prepared by MAE and LPE methods were dissimilar, ascribing to different reaction systems and characteristics. FTIR, SEM, and transparency analyses were used to investigate the chemical structure and surface characteristics of CAB films, and appearance, glossiness, rub resistance, and ethanol resistance measurements were carried out to investigate the surface and wear characteristics of CAB/pearlescent coating films. The results indicated that the surface and wear characteristics of the films based on MAE- and LPE-prepared CABs were similar to the same reaction time, and the interfacial adhesion and compatibility among components significantly affected the characteristics of the films.

研究领域: 材料科学 · 化学工程
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