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NEW JOURNAL OF CHEMISTRY · 2023 ·Vol. 47 ·期 23 ·11318-11324 · IF 3.3

A general and selective Ni-catalysed reductive amination using hydrazine hydrate as facile hydrogen and nitrogen sources

Jiazheng Zhu,Chengjie Duan,Sen Ye,Qizhong Zhang,Kun Li,Guangke He,Xiang Liu,Zhiguo Zhang

Exploring synthetic methods and catalysts that are easy to handle, highly active, and low-cost for producing industrially important chemicals is a long-term goal in both science and industry. Herein, we present a general and facile Ni-catalyzed reductive amination of aldehydes/ketones methodology using hydrazine as both nitrogen and hydrogen sources, instead of the traditionally used hydrogen gas and ammonia. The mesostructured alumina-supported Ni catalyst with a relatively high ratio of Ni0 and small-sized Ni nanoparticles plays a critical role in this transformation, resulting in 55 aldehydes/ketones successfully converting to their corresponding primary amines with 61–99% yields. This work outlines a low-cost yet robust catalytic methodology for the facile and general synthesis of primary amines for practical laboratory and industrial application.

CAS / MDL: 1344-28-1 10026-12-7
研究领域: 有机化学 · 催化化学
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CATALYSIS LETTERS · 2022 ·Vol. 153 ·期 4 ·1215-1226 · IF 2.936

Combining Ni3P and Lewis Acid–Base Pair as a High-Performance Catalyst for Amination of 1-Octanol

Wang Shiqing,Li Yafei,Lan Xiaocheng,Liu Boyang,Wang Tiefeng

Ni phosphide and Lewis acid–base pair site of Al 2 O 3 were combined as highly efficient catalyst for direct amination of 1-octanol to 1-octylamine. Due to the higher dehydrogenation activity and the site isolation effect, Ni 3 P/Al 2 O 3 -TPP prepared by organophosphorus was 4.0 times more active than Ni/Al 2 O 3 and increased the selectivity to 1-octylamine from 71.4 to 92.8% at 0.4 MPa NH 3 . Graphical Abstract

CAS / MDL: 13478-00-7 603-35-0
研究领域: 催化化学 · 材料科学
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MOLECULES · 2018 ·Vol. 23 ·期 9 ·2234 · IF 3.098

Imidazolium Chloride: An Efficient Catalyst for Transamidation of Primary Amines

Qingqiang Tian,Zongjie Gan,Xuetong Wang,Dan Li,Wen Luo,Huajun Wang,Zeshu Dai,Jianyong Yuan

A highly efficient and convenient protocol of imidazolium chloride (30 mol %) catalyzed amidation of amines with moderate to excellent yields was reported. The protocol shows broad substrate scope for aromatic, aliphatic, and heterocyclic primary amines.Keywords:imidazolium chloride;catalyst;primary amines;transamidation

研究领域: 有机化学 · 催化反应
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ChemCatChem · 2019 ·Vol. 11 ·期 22 ·5562-5569 · IF 4.495

Selective Synthesis of Furfurylamine by Reductive Amination of Furfural over Raney Cobalt

Kuo Zhou,Bixian Chen,Xiaoting Zhou,Shimin Kang,Yongjun Xu,Jinjia Wei

Graphical Rane drops keep fallin’ : Cobalt proved to be the most efficient metal for furfurylamine synthesis by reductive amination of furfural with NH 3 and H 2 . Effect of metal nature on reductive amination was investigated with biomass-based furfural as a typical substrate. Among the tested heterogeneous metal catalysts, cobalt proved to be the most effective metal for the synthesis of the corresponding primary amine. Under a relatively mild reaction condition, 98.9 % yield of furfurylamine was obtained over Raney Co and it can be reused more than eight times without a significant decrease in the catalytic performance. By extensively studying the catalytic pathways and reaction mechanism, it is found that the selectivity to primary amine and secondary amine was governed by the relative rate of hydrogenolysis and hydrogenation of the Schiff base intermediate. The superiority of Raney Co in furfurylamine synthesis can be ascribed to its high efficiency on hydrogenolysis of the Schiff base intermediate and its low performance in the hydrogenation of the Schiff base, carbonyl group and furan ring. Furthermore, ammonia greatly promoted the catalytic hydrogenolysis of the Schiff base intermediate over Raney Co without clear deactivation of the metal active sites.

研究领域: 化学工程 · 生物质转化 · 催化科学
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INDUSTRIAL CROPS AND PRODUCTS · 2015 · IF 2.837

Five new sulphur-containing amides from Glycosmis lucida with antifeedant activity against Tribolium castaneum

Kai Yang,Shan-Shan Guo,Zhu-Feng Geng,Chun-Xue You,Wen-Juan Zhang,Yin-Ping Li,Cheng-Fang Wang,Shu-Shan Du,Zhi-Wei Deng

Five new sulphur-containing amides ( 2 , 5 – 8 ) and three known analogue compounds ( 1 , 3 – 4 ) were isolated from the leaves of Glycosmis lucida which were collected in Yunnan province, China. Their structures were elucidated with NMR spectroscopy and mass spectrometry. The compounds were identified as N -( p -hydroxyphenethyl)-3-(methylsulfonyl)-propenamide ( 1 ), N -[2-(4- hydroxyphenyl)-ethyl]-3-methanesulfonyl- N -methyl-propionamide ( 2 ), methylgerambullin ( 3 ), methylisogerambullone ( 4 ), methylgerambullindiol ( 5 ), N -{2-[4-(6,7-hydroxy-3,7-dimethyl-oct- 2-enyloxy)-phenyl]-ethyl}-3-methanesulfonyl- N -methyl-acrylamide ( 6 ), N -{2-[4-(6,7-dihydroxy- 3,7-dimethyl-oct-2-enyloxy)-phenyl]-ethyl}-3-methanesulfonyl- N -methyl-propionamide ( 7 ), ( E )- N -{2-[4-(6-hydroxy-7-dimethyl-oct-2-enyloxy)-phenyl]-ethyl}-3-methanesulfinyl- N -methyl- acrylamide ( 8 ). Feeding deterrent activities of these surphur-containing derivatives against Tribolium castaneum were assayed for the first time. Compound 2 , 3 , 6 possessed significant feeding deterrent activities against T. castaneum adults (EC 50   =   311.6, 244.9 and 108.3   ppm, respectively). These results demonstrated that some sulphur-containing amides are promising candidates as insect antifeedant agents.

CAS / MDL: 9005-64-5
研究领域: 植物化学 · 昆虫学 · 天然产物研究
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ChemistryOpen · 2020 ·Vol. 9 ·期 10 ·996-1000 · IF 2.37

Unveiling the reaction process of the amine in direct amidation of aromatic ketones in H2O

Fangjun He,Rumeng Qu,Jie Su,Muyao Du,Junqiang Liu,Yiping Chen,Bo Wang

Graphical Solving the puzzle : The role of the amine in direct amidation of aromatic ketones has been investigated. Amines act as both the reactant and catalyst, as such the excess amount (two or more equivalents) of amines are required to afford reasonable conversions/yields in the classical amidation. The direct amidation of aromatic ketones has been achieved at mild reaction conditions. In the classical amidation between aromatic ketones and amines, 2.0 equivalents of amines are necessarily required to gain satisfying yields. The specific role of the amine in the direct amidation already puzzled us for a long time. In this work, we disclosed that the amine acts as both reactant and catalyst. Specifically, the determination of reaction intermediates revealed the full mechanism, based on which, the introduction of one equivalent base in the amidation is showcased here that a high yield (∼95 %) can be afforded using only 1.1 equiv. of amine.

研究领域: 有机化学 · 催化化学
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Journal of Water Process Engineering · 2024 · IF 6.3

2D-3D cyclodextrin-modified montmorillonite assembly for efficient directional capture of amines

Wenxin Dong,Peiran Wen,Can Wang,Haodong Tian,Dan Mou,Jiuqiang Huang,Rongrong Hu,Zongshan Xue,Deyi Jiang,Daokui Li

Shale gas exploitation produces a large amount of waste liquid, which cannot be fully recovered and discharged. Discharged wastewater contains several chemicals, including petroleum hydrocarbons, salts, and heavy metals. Amine compounds can absorb harmful gases but may lead to the presence of these compounds in wastewater. Some amine compounds may cause DNA mutations and health threats to humans and animals. Inspired by the assembly of artificial two-dimensional structures, this paper attempts to shape montmorillonite (MMT) with a natural layered structure. Specifically, a functional 2D/3D amine compound collector within the limitations of 2D MMT (Mt) was prepared by self-assembling cyclodextrin molecules. With the assembly of cyclodextrin (CD) molecules, the two-dimensional Mt. layer length increased from 12.14 to 19.11 Å. Adsorption experiments revealed that functional MMT powder (FMP) has good trapping ability for amines, that the adsorption of amine groups on FMP decreases with increasing temperature, and that it has greater potential to remove amine compounds with fewer carbon chains. Through molecular dynamics simulation, it was found that there was a molecular binding energy between FMP and branched polyethyleneimine (BPEI), indicating that FMP had a spontaneous adsorption effect on BPEI. Furthermore, their adsorption favored the Langmuir isotherm model and the pseudo-second-order kinetic model. This study also provides a new collector for the total organic carbon (TOC) advanced treatment system. Compared with that of ozone and UV treatment, the removal rate of FMP is 10 times higher than that of activated carbon and active resin, which can better remove polar molecules and is beneficial for gas field water recovery.

研究领域: 环境科学 · 材料科学
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Scientific Reports · 2017 ·Vol. 7 ·期 1 ·1-12 · IF 4.259

Characterization of O-acetylation in sialoglycans by MALDI-MS using a combination of methylamidation and permethylation

Wu Zhaoguan,Li Henghui,Zhang Qiwei,Liu Xin,Zheng Qi,Li Jianjun

O -Acetylation of sialic acid in protein N-glycans is an important modification and can occur at either 4-, 7-, 8- or 9-position in various combinations. This modification is usually labile under alkaline reaction conditions. Consequently, a permethylation-based analytical method, which has been widely used in glycomics studies, is not suitable for profiling O -acetylation of sialic acids due to the harsh reaction conditions. Alternatively, methylamidation can be used for N-glycan analysis without affecting the base-labile modification of sialic acid. In this report, we applied both permethylation and methylamidation approaches to the analysis of O -acetylation in sialic acids. It has been demonstrated that methylamidation not only stabilizes sialic acids during MALDI processing but also allow for characterization of their O -acetylation pattern. In addition, LC-MS/MS experiments were carried out to distinguish between the O -acetylated glycans with potential isomeric structures. The repeatability of methylamidation was examined to evaluate the applicability of the approach to profiling of O -acetylation in sialic acids. In conclusion, the combination of methylamidation and permethylation methodology is a powerful MALDI-TOF MS-based tool for profiling O -acetylation in sialic acids applicable to screening of N-glycans.

CAS / MDL: 64-18-6 67-66-3
研究领域: 生物化学 · 分析化学 · 糖组学
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INDUSTRIAL CROPS AND PRODUCTS · 2025 · IF 6.2

Dual-functionalization of lignin towards superior reinforcement for styrene-butadiene rubber

Jiye Teng,Tao Zhang,Hongbo Zhao,Peiling Zhang,Zhengzhe Wu,Zhiwei Chang,Ming Li,Chenjie Zhu

Developing lignin-based fillers for reinforcing rubber materials has been recently spotlighted. This work modified lignin via a simple amination and a silylation reaction in a one-pot two-step manner. The molecular structure of aminated lignin (LN) was verified using 2D-HSQC, XPS and elemental analysis. The following silylation on LN results in dual-functionalized lignin (LNSi). LN and LNSi show improved hydrophobicity, reduced Hansen solubility parameters and morphology of nanoparticles (<50 nm). Styrene-butadiene rubber (SBR) composites containing 40 phr of fillers were prepared through latex compounding. SBR-LNSi presents comparable tensile strength to the references with carbon black and silica, and enhanced hardness. These remarkable mechanical performances correlate with its high dispersity and affinity with SBR matrix, and the improved rigidity and structuredness due to the self-condensation of silanol groups. This study provides a proof-of-concept for designing lignin-derived fillers with superior reinforcing effect on rubber materials.

研究领域: 材料科学 · 化学工程
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2020 · IF 3.99

MoS2 decorated with ZrO2 nanoparticles through mussel-inspired chemistry of dopamine for reinforcing anticorrosion of epoxy coatings

Yujuan Jing,Pingquan Wang,Qiangbin Yang,Qiurun Wang,Yang Bai

Faced with severe corrosion of casing in oil wells, the epoxy coating was applied to prevent corrosion. Based on the mechanism that the filler eliminated the internal stress during the curing process of the coating and prevented the penetration of corrosive medium into the coating, a new filler was successfully prepared by the hydrothermal method . When the molar ratio of the precursor of ZrO 2 to MoS 2 was 1.2:1, MoS 2 was uniformly modified with ZrO 2 through mussel inspired chemistry of dopamine. Introducing fillers into epoxy coatings, specifically, a proper content of 0.8 wt.% filler can greatly improve the mechanical properties and corrosion resistance of the coatings. The coating maintained the excellent corrosion resistance for 16 h under high temperature (108  °C) and high pressure (pressurized with CO 2 gas of 35 MPa), which would provide us a reliable anticorrosive coating for oil wells metal casing.

CAS / MDL: 62-31-7 77-86-1
研究领域: 材料科学 · 化学工程
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SCIENCE OF THE TOTAL ENVIRONMENT · 2023 · IF 9.8

Influencing pathways and toxicity changes of pre-ozonation on carcinogenic NDEA formation from greenhouse gas adsorbent DEAPA in subsequent disinfection processes

Tianze Liu,Xiaobin Liao,Xinna Lin,Jing Yu,Huan Qi,Zhibin Jiang,Jing Zou,Qingsong Li

This study was to evaluate the feasibility of controlling carcinogenic nitrosodiethylamine (NDEA) formation from greenhouse gas adsorbent 3-diethylaminopropylamine (DEAPA) by pre-O 3 in subsequent chlorination/chloramination processes. The result indicated that the NDEA yields (0.4 %) during chlorination was 1.3 times of that during chloramination (0.3 %); pre-oxidation with 4 mg/L O 3 significantly cut down its formation; the reduction rates were up to 67.5 and 48.5 %, respectively. OH scavenger greatly augmented the final NDEA amount from 1.86 to 5.05 μg/L during ozonation , while its roles on subsequent processes differed with disinfection methods as well as O 3 (g) dosages. Most of co-existed substances inhibited NDEA generation, except NO 2 − , CO 3 2− and SO 4 2− , which slightly promoted during ozonation. Basing on Gaussian calculation, GC/MS and UPLC-Q-TOF-MS analysis, the influencing mechanisms of pre-O 3 on NDEA formation in subsequent disinfection processes were proposed. In addition, the calculated toxicity analysis as well as the whole toxicity was applied to evaluate the possibility of pre-O 3 on risk control.

研究领域: 环境科学 · 水处理工程 · 毒理学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2023 · IF 4.2

Synthesis of Acetonitrile from Ethanol Dehydroamination over a La-Modified Co/Al2O3 Catalyst

Lin Mei,Chao Feng,Yuzhong Wang,Qiang Yu,Wenjie Xin,Weifeng Chu,Yanan Wang,Xiangxue Zhu,Shenglin Liu,Hongxia Wang,Longya Xu

Synthesis of acetonitrile (ACN) by way of ethanol dehydroamination process was performed over copper-, zinc-, nickel-, and cobalt-based catalysts in a fixed-bed reactor, by which 20Co/Al2O3 was found to be the best one and ready for subsequent La, Ce, and Pr doping. Then, catalytic tests and a series of characterizations such as XRD, XRF, XPS, TEM, TG-DTA, IGA, NH3-TPD, and N2 adsorption–desorption were carried out. The results demonstrate that rare-earth-modified 20Co/Al2O3 catalysts have improved the catalytic performance for ethanol dehydroamination remarkably; the addition of La leads to better dispersion of cobalt species, the higher surface area of 20Co/Al2O3 catalyst, and fast adsorption for ACN, as well as better resistance to carbon deposition. In the meantime, the La-doped catalyst seems to prefer the route of acetaldehyde imine to ACN rather than to ethylamine, and consequently, a highly selective synthesis of ACN with excellent catalytic stability was obtained with the formation of ethylamine being suppressed..

研究领域: 催化化学 · 材料科学
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