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Inorganic Chemistry Frontiers · 2024 ·Vol. 11 ·期 5 ·1596-1606 · IF 6.1

Synthesis of nano-sized SAPO-34 using a facile micron-meter seed processing method and their enhanced performance in methanol-to-olefin reactions

Dehua Wang,Minghui Mo,Man Xu,Zhijun Xia,Xuebin Zhao,Beibei Gao

Seed-assisted synthesis of nano-SAPOs usually requires a costly nano-sized seed, and the micron-sized seed used should be ball-milled or treated under reflux to broke them into nano-particles. In this study, nano-sized SAPO-34 was prepared using a micron-meter SAPO-34-M seed that was treated facilely with morpholine (MOR) within a Teflon-lined stainless steel autoclave to obtain a seed solution. As MOR was also the template for SAPO-34 synthesis, no extra template was added to the precursor gel. The effects of MOR treatment time on seed properties and the subsequent SAPO-34 fabrication were characterized via XRD, SEM, N2 adsorption–desorption, 29Si NMR and NH3-TPD techniques. The effect of the seed amount on the products was also investigated. There existed optimum seed treatment time and seed addition amount for synthesizing uniform nano-sized SAPO-34 with the characteristics of larger mesopore volume, lower Si contents and acid density and weaker acid strength than conventional SAPO-34. Moreover, heterologous seed-assisted syntheses of SAPO-34 were carried out, and it is found that micron-sized heterologous seeds (AFI, RHO, LEV and AFX) treated with MOR can also deliver nano-sized SAPO-34, although AFI and RHO share no common composite building units (CBUs) with CHA, suggesting that seed selection in this synthesis strategy is not confined to a specific topology. The obtained nano-sized SAPO-34 catalysts exhibited about a 2.7-fold prolonged lifetime and nearly 5% increased selectivity for ethylene and propylene compared to their conventional micron-sized counterparts in methanol-to-olefin (MTO) reactions.

研究领域: 材料科学 · 催化化学 · 能源化学
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CHEMICAL ENGINEERING JOURNAL · 2022 · IF 16.744

Kinetic and mechanistic insights into the roles of protonated morpholine species and weak acidic environment in methylacrolein production catalyzed by morpholine/acid

Qiu Zhao,Hui Zhao,Gang Wang,Hanwen Yan,Junping Zhang,Xinyue Liu,Yijun Cao

Synthesis of methylacrolein (MAL) from formaldehyde and propanal via Mannich reaction receives significant attention considering the gradual depletion of petroleum resource. Herein, series of morpholine/acid catalyst with different acid type and molar ratio were prepared to catalyze the propanal-formaldehyde reactions for MAL production. The catalytic performance of morpholine/acid was significantly affected by the morpholine/acid ratio, acid type, and initial pH value of reactant mixture. While the addition sequence of reactants and formaldehyde source would influence the yield and selectivity of MAL. As a result, the propanal conversion and MAL yield could reach 99.8 % and 89.7 % with catalysis of morpholine/acetic acid having the molar ratio of 1/3 under weak acidic environment (pH = 5.30) at 50 °C. It was revealed that the protonation of morpholine under weak acidic environment could effectively inhibit the deactivation of morpholine/acetic acid catalyst and promote the production of MAL, however, both basic and strong acidic environment would suppress the formation of MAL. Mechanistic DFT calculations also indicated the protonated morpholine species could not only interact with formaldehyde in the form of morpholine but also act as proton donor. The kinetic studies showed that the formation rate of MAL was first-order dependent on the concentrations of both propanal and formaldehyde with the activation barrier of 30.1 kJ/mol. Undesirably, the optimal morpholine/acetic acid catalyst would be gradually deactivated due to the side reactions of morpholine with formaldehyde, propanal and MAL.

CAS / MDL: 141-82-2 123-38-6
研究领域: 化学工程 · 催化化学
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CHINESE JOURNAL OF CHEMICAL PHYSICS · 2019 ·Vol. 32 ·期 2 ·259-266 · IF 0.791

Dissociative photoionization of heterocyclic molecule-morpholine under VUV synchrotron radiation

Song Wen-tao,Hu Yong-jun,Jin Shan,Li Yu-jian

The radiation damage of biomolecules, in particular with aliphatic compound, has been extensively studied. Morpholine is a typical six-membered aliphatic heterocyclic compound. In the present work, photoionization and dissociation of the morpholine monomer and subsequent fragmentations have been investigated by synchrotron vacuum ultraviolet photoionization mass spectrometry and theoretical calculations. The vertical ionization energy of morpholine monomer is 8.37±0.05 eV, which agrees reasonably well with a theo-retical value 8.41 eV of morpholine. Experimentally observed fragmentation of morpholine ( m/z =87 amu) gives rise to m/z =86 amu, m/z =57 amu, and m/z =29 amu. Based on experimental and theoretical results, it is found that the m/z =86 amu is produced by losing H atom, the m/z =57 amu is formed by the elimination of CH 2 O with a ring-opening process, the m/z =29 amu is generated by further dissociation of the fragment m/z =57 amu (C 3 H 7 N) + by the elimination of C 2 H 4 . This finding would provide valuable insight into the photo-damage of aliphatic compounds, which may be related to living cells and other biological system.

CAS / MDL: 110-91-8
研究领域: 生物化学 · 分子生物学 · 物理学
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JOURNAL OF THE INDIAN CHEMICAL SOCIETY · 2025 · IF 3.4

Synthesis and antitumor activity of 4-aminoquinazoline derivatives containing morpholine moieties

Xinxin Zhou,Yicheng Mei,Baowei Yang,Jing Wang,Huiling Tang,Xiaolong Zhang,Changchun Liu

Eight 4-(morpholinyl arylamino)quinazoline-6-carbamoyl carboxylic acid methyl esters and four 4-(morpholinyl arylamino)quinazoline-6-carbamoyl hydroxamic acid derivatives were designed and synthesized by integrating morpholine moieties into the 4-aminoquinazoline scaffold, with additional modifications at the 6-position of quinazoline ring. The antitumor potential of these twelve derivatives was evaluated against human lung cancer A549 cells and breast cancer MDA-MB-231 cells using the Cell Counting Kit-8 (CCK-8) proliferation assays. The bioassay results indicated that most of the derivatives exhibited moderate to potent in vitro antiproliferative activity against both cancer cells. Particularly, compound 7bb demonstrated superior potency against MDA-MB-231 cells and A549 cells, with half maximal inhibitory concentration (IC 50 ) values of 4.286 and 4.720 μM, respectively, compared to the reference drug afatinib (IC 50  = 7.640 and 5.173 μM, respectively). This study provides valuable insights for the development of novel antitumor agents based on the 4-aminoquinazoline scaffold.

研究领域: 药物化学 · 肿瘤学
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RSC Advances · 2017 ·Vol. 7 ·期 65 ·40705-40710 · IF 3.108

High-flux polyamide reverse osmosis membranes by surface grafting 4-(2-hydroxyethyl)morpholine

Ruizhi Pang,Kaisong Zhang

Surface modification is a common approach to improve the desalination performance of polyamide (PA) reverse osmosis (RO) membranes. Nevertheless, the water flux normally decreases due to the additional hydraulic resistance of the surface modification layer. Surface grafted PA RO membrane with 4-(2-hydroxyethyl)morpholine was first fabricated to improve water flux in this study. 4-(2-Hydroxyethyl)morpholine was in situ grafted onto the nascent PA membrane by the reaction between the –OH group of 4-(2-hydroxyethyl)morpholine and the unreacted –COCl groups of the nascent PA membrane and residual trimesoyl chloride. The surface grafted RO membranes were characterized by X-ray photoelectron spectrometry, field emission scanning electron microscopy, atomic force microscopy and contact angle measurement. The surface grafting conditions, including 4-(2-hydroxyethyl)morpholine dipping time, heat treatment time, and 4-(2-hydroxyethyl)morpholine concentration, were optimized by characterizing the desalination performance under brackish water desalination conditions. The resulting surface grafted membrane exhibited a water flux of 125.71 L m−2 h−1 and a salt rejection of 98.6%. The surface grafted membrane surpassed the control polyamide membrane with 41.9% increase in the water flux. Our results demonstrated that surface modification by in situ grafting 4-(2-hydroxyethyl)morpholine is a promising approach to fabricate high-flux RO membranes.

研究领域: 材料科学 · 膜技术 · 化学工程
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Biomolecules · 2026 ·Vol. 16 ·期 7 ·1002 · IF 5.6

Design, Synthesis, and Biological Evaluation of Novel Morpholine–Coumarin Derivatives for Inflammation-Associated Depression

Hui Liu,Lina Hu,Yalan Wang,Zheshan Quan,Zheng Liu,Shiben Wang,Qingkun Shen

The tryptophan–kynurenine pathway, mediated by indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), is critically involved in the pathogenesis of depression. A series of novel morpholine–coumarin derivatives were designed and synthesized as dual IDO1/TDO inhibitors. Through in vitro enzyme screening, compound14dexhibited potent inhibitory activity with IC50values of 0.34 µM and 0.75 µM, respectively. In lipopolysaccharide (LPS)-stimulated BV2 microglial cells,14ddownregulated IDO1/TDO expression, suppressed pro-inflammatory cytokines (IL-1β, COX-2, iNOS, TNF-α), and upregulated the anti-inflammatory cytokine IL-10. In an LPS-induced acute depressive mouse model established in C57BL/6 mice, intraperitoneal administration of14d(20 mg/kg) significantly reduced immobility time in the forced swim and tail suspension tests, without affecting spontaneous locomotor activity. Mechanistic studies revealed that14dinhibited microglial activation in the hippocampal dentate gyrus, reduced cerebral kynurenine levels, increased serotonin content, and upregulated BDNF/PKA signaling. Molecular docking further predicted the binding interactions of14dwith the active sites of IDO1 and TDO. These findings suggest that14drepresents a promising dual IDO1/TDO inhibitor lead compound for the treatment of inflammation-associated depression through modulation of the kynurenine pathway and neuroinflammatory responses.

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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2026 · IF 5.4

Light-switchable emulsion control and phase transfer enabled by a morpholine-functionalised azobenzene surfactant

Hongyan Xue,Jiaming Feng,Biquan Su,Zhihang Wang,Nong Wang

Surfactants are widely used to stabilise emulsions across chemical, pharmaceutical, and environmental processes, yet conventional systems often lack controllability once formed. Smart surfactants capable of reversible emulsification and demulsification therefore offer a promising route toward adaptive formulations, especially when activated by non-invasive light stimuli. In this study, a morpholine-functionalised, photoswitchable azobenzene surfactant (MBAB) was synthesised to enable controllable reversible emulsion through trans – cis photoisomerisation. Using MBAB, a stable, reversible oil-in-water emulsion (MBAB/CTAB/n-hexane/water) was constructed, exhibiting repeatable demulsification and re-emulsification under alternating ultraviolet and visible light irradiation. Kinetically, the hydrophilicity of morpholine ring enhances interfacial hydration, resulting in robuster interfacial membrane and slower photoresponsive behaviour compared with linear alkyl analogues. Beyond demulsification and re-emulsification function, a reversible phase-transfer emulsion system (MBAB/n-octanol/water) was also established, in which UV-induced trans – cis isomerisation increases MBAB’s polarity, driving its migration from the n-octanol phase into water, with visible light restoring the original phase distribution. Both systems display excellent cycling stability, maintaining performance over at least ten switching cycles without significant loss of efficiency. Overall, this work provides an effective strategy for designing reversible photoresponsive surfactants and light-switchable emulsions, offering new opportunities for studying stimulus-responsive interfacial assembly and enabling intelligent separation and controlled-release technologies.

CAS / MDL: 584-08-7
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TRANSACTIONS OF TIANJIN UNIVERSITY · 2012 ·Vol. 18 ·期 5 ·315-319 · IF 0

Synthesis and characterization of novel copolymers based on 3(S)-methyl-morpholine-2,5-dione

Feng Yakai,Chen Chengbin,Zhang Li,Tian Hong,Yuan Wenjie

A series of novel copolymers were successfully synthesized by ring-opening polymerization (ROP) of 3(S)-methyl-morpholine-2,5-dione (MMD) and 5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one (MBC) using stannous octoate as catalyst. The copolymers were characterized by means of 1H-NMR and FT-IR spectroscopy. Gel permeation chromatography (GPC) test shows that the average-number relative molecular mass and average-weight relative molecular mass slightly increase with the increase of MBC content in feed. The results of differential scanning calorimetry (DSC) demonstrate that the glass transition temperature of copolymers increases with the increase of MBC content in copolymers. The copolymers of MMD and MBC are amorphous copolymers, as indicated by DSC results, while the homopolymer of MMD is semicrystalline.

研究领域: 高分子化学 · 材料科学
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ANALYTICA CHIMICA ACTA · 2022 · IF 6.911

AIE fluorescent probe based on tetraphenylethylene and morpholine-thiourea structures for detection of HClO

Dongying Pan,Yan Don,Yunhua Lu,Guoyong Xiao,Haijun Chi,Zhizhi Hu

As an important signal molecule in the living body, hypochlorous acid (HClO) participates in various physiological processes . However, excessive hypochlorous acid will cause some oxidative damage. The organic aggregation-induced emission luminogens (AIEgens) based on tetraphenylethylene (TPE) structures have recently become research hotspots as fluorescent probe materials. In this paper, a kind of water-soluble fluorescent probe TPE-M based on TPE and morpholine-thiourea structures were designed and synthesized for the detection of HClO. Due to the introduction of morpholine structures, the TPE-M showed excellent water solubility. The fluorescence properties of the TPE-M were strongly affected by the polarity of the solvent. Besides, the cation-anion and reactive oxygen species recognition experiments indicated that the fluorescent probe TPE-M displayed a single recognition characteristic for HClO because of the existence of thiourea structures. The limit of detection for HClO was calculated to be 0.25 μM. The particle size distribution measurement under the water phase revealed that the particle size of the TPE-M was mainly centered at 150 nm. The recognition mechanism of HClO by the probe TPE-M was proposed and explained by mass spectra and Gaussian calculation. Furthermore, a cell imaging experiment proved that the TPE-M probe successfully detected HClO in Hela cells.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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CELLULOSE · 2020 ·Vol. 27 ·期 12 ·6861-6870 · IF 4.21

Quantification of N-methyl morpholine N-oxide in biorefinery process solution by headspace gas chromatography

Zeng Tong,Ke Xun,Li Lijuan,Cheng Xinlei,Ni Yonghao,Ouyang Xinhua,Zhang Xingye,Chen Lihui,Huang Liulian,Hu Hui-Chao

Abstract This work developed a novel method for the determination of N-methyl morpholine N-oxide (NMMO) in the solution of biorefining, such as lyocell or biomass pretreatment. Copper hydride in situ (CuH) was generated in alkaline solution from sodium borohydride and cupric ion to completely reduce NMMO to N-methyl morpholine (NMM). Finally, the generated volatile NMM was analyzed by headspace gas chromatography. The generation of in situ CuH, complete reduction of NMMO, and the gas–liquid equilibration of NMM can be synchronously completed at 80 °C in 30 min, with a cupric ion concentration of 20 μmol, sodium hydroxide (0.8 mmol), sodium borohydride (3.0 mg), and 1.0 mL 30% ammonium hydroxide in 5.0 mL aqueous solution. The lowest limit of NMMO quantification was 42 mg/L in the present method, with good precision (standard deviation = 5.62%) and accuracy (recoveries from 95.9 to 106%). The present method has high accuracy, sensitivity, and throughput. It should be a useful tool to determine the content of NMMO and allow optimize the cost efficiency. Graphic abstract

研究领域: 分析化学 · 生物工程
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RSC Advances · 2017 ·Vol. 7 ·期 11 ·6179-6186 · IF 3.108

Molecular structures of gas-phase neutral morpholine and its monohydrated complexes: experimental and theoretical approaches

Huaqi Zhan,Yongjun Hu,Pengchao Wang,Jiaxin Chen

Morpholine (NH(CH2CH2)2O) is a typical six-membered aliphatic heterocyclic compound. Herein, infrared plus vacuum ultraviolet (IR/VUV) single photon “soft” ionization spectroscopy was employed to study the structures of neutral morpholine and its monohydrated clusters. Theoretical calculations revealed that the structures containing equatorial-chair and axial-chair conformations were the most stable conformers in the gas phase, and this was confirmed by IR spectral analysis. Analysis of the observed and calculated spectra of the monohydrated clusters suggested that multiple conformers may co-exist in the molecular beam, and that the water molecule acts as a hydrogen donor. In the most stable structure, the hydrogen atom of the water molecule is bound to the NH group of the equatorial-chair conformer of morpholine. Moreover, the water molecules simultaneously serve as hydrogen bond donors for the NH group and interact with the CH group weakly. It is suggested that the weak intermolecular CH⋯O interaction is also responsible for the molecular stability.

CAS / MDL: 110-91-8
研究领域: 化学 · 物理化学 · 分子光谱学
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JOURNAL OF HAZARDOUS MATERIALS · 2020 · IF 9.038

The absorption of SO2 by morpholine cyclic amines with sulfolane as the solvent for flue gas

Can Cheng,Jianjun Li,Jinyan Cao,Jiaxiu Guo,Wanglai Cen

The absorption properties of N-(2-hydroxyethyl) morpholine (HEM), morpholine (MP) and N-(2-aminoethyl) morpholine (AEM) for SO 2 were studied using sulfolane (SUL) as solvent in this work. Among these solvent combinations, HEM/SUL shows the best cyclic absorption performance, and the capacity of HEM-SUL-40 (40 wt% of HEM and 60 wt% of SUL) to absorb 8580 mg/m 3 SO 2 (the remainder is N 2 ) is 192.18 mg/g at 293.15 K. The absorption capacity of the second cycle is 97.5% of the first absorption cycle, which is higher than 70% of the Cansolv amine solution in a commercial application with similar experimental conditions. However, MP/SUL is difficult to desorb at high temperature, and the absorption capacity of AEM/SUL is much lower than HEM/SUL and MP/SUL. According to the FTIR , 1 H NMR and 13 C NMR, all three cyclic amines have charge transfer effects with SO 2 . The structure of HEM/SUL can be recovered after heating, but MP cannot be recovered. Δ r G m ° in the reaction against HEM with SO 2 increases significantly with increasing temperature. The Δ r G m ° of HEM-SO 2 and MP-SO 2 at 353.15 K is −12.56 kJ/mol and −16.29 kJ/mol, respectively, which further explains the easy desorption of HEM-SO 2 and the difficult desorption of MP-SO 2 at high temperature.

CAS / MDL: 9008-02-0 7704-34-9
研究领域: 化学工程 · 环境科学 · 物理化学
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