INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
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2025
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IF 3.9
Shuxing Zhang,Xiaoshu Ding,Yanji Wang
5-Amino-1-pentanol is an important pharmaceutical intermediate used in the synthesis of anti-inflammatory and anticancer drugs. The direct hydrogenolysis of furfurylamine to 5-amino-1-pentanol has the advantages of a simple process route and high atom utilization. In this paper, for Pt/ZrO2 catalysts, the effects of different Pt loading and calcination temperatures on catalyst activity, selectivity, and surface properties such as Pt nanoparticle size, acidity and alkalinity, and the ratio of Pt0/(Pt0+Pt2+) were investigated. Through the study of the relationship between catalyst preparation conditions, furfurylamine hydrogenolysis reaction performance, and surface properties, it was found that moderate Pt nanoparticle size, higher Pt0/(Pt0+Pt2+) ratio, and more acidic sites favored furfurylamine hydrogenolysis. The higher number of basic sites favors the dispersion of Pt metal. The results of in situ FTIR show that the amino group of furfurylamine is adsorbed on the acidic site of Pt/ZrO2, and the furan ring is adsorbed on Pt nanoparticles, which is beneficial to the hydrogenolysis of furfurylamine.
研究领域:
催化化学
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药物合成
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DOI
高影响因子
CATALYSIS LETTERS
·
2022
·Vol. 153
·期 9
·2813-2823
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IF 2.936
Yang Jian,Li Xuemei,Zhang Jia,Tian Junying,Yao Xiaolan,Liu Hailong,Xia Chungu,Huang Zhiwei
Valuable 5-amino-1-pentanol (5-AP) was efficiently synthesized from biomass-derived dihydropyran over hydroxylapatite nanorod supported Ni catalysts (Ni-HAP), by coupling the in situ generation of 5-hydroxypentanal (5-HP, via the ring-opening tautomerization of 2-hydroxytetrahydropyran (2-HTHP)) and its subsequent reductive amination. The Ni-HAP catalyst with 10 wt% Ni loading exhibited the highest 5-AP yield than the other Ni-HAP catalysts with different Ni loadings and several commercial hydrogenation catalysts, including Ru/C, Pt/C and Pd/C, as well as Raney Ni. High Ni particles dispersion, high reducibility and acidic intensity were found to account for the superior catalytic performance of 10Ni-HAP. The effect of reaction parameters on the catalytic performance was investigated, and an excellent 5-AP yield of 92% was achieved under mild reaction conditions of 80 °C and 2 MPa H 2 . The stability of the Ni-HAP catalyst was studied using a continuous flow reactor, and the sintering of Ni nanoparticles was considered as the major reason for the decline in hydrogenation activity. Graphical Abstract The Ni-HAP catalyst exhibited high catalytic performance to synthesis 5-AP due to the high Ni particles dispersion, reducibility and acidic intensity.
研究领域:
催化化学
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可再生化学
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DOI
高影响因子
Green Synthesis and Catalysis
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2023
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IF 0
Jia Zhang,Jian Yang,Xuemei Li,Bin Mu,Hailong Liu,Chungu Xia,Aiqin Wang,Zhiwei Huang
The efficient synthesis of useful primary amines via reductive amination of biomass-based aldehydes and ketones over earth-abundant base metal catalysts is an attractive biomass value-adding technology yet facing lots of challenges. Herein, natural attapulgite (ATP) was applied as support for the fabrication of active Ni catalysts with different Ni loadings (5–30 wt%) by the deposition-precipitation method. The Ni/ATP-550 catalyst with 10–15 wt% Ni loadings was found to present the highest catalytic performance for the synthesis of valuable 5-amino-1-pentanol (5-AP) via reductive amination of biofurfural-derived 2-hydroxytetrahydropyran among a variety of commonly used oxide supports loaded Ni catalysts, as well as ATP supported nickel catalysts with other loadings, achieving 5-AP yield up to 94%. The intrinsic activity of the Ni/ATP catalysts was found to depend strongly on the Ni 0 crystallite size and Ni 0 fraction of the catalysts, which generally increased with increasing Ni 0 crystallite size and fraction, owing probably to the hydrogenation of imine intermediate is a structure-sensitive reaction. The efficient 10Ni/ATP-550 catalyst also exhibited good activity and stability in the reductive amination of several other biomass-derived aldehydes and ketones to their corresponding primary amines with good to excellent yields (81%–99%). This work provided a clean and efficient natural ATP-supported non-noble metal nickel-based catalytic system for the reductive amination of aldehydes and ketones to synthesize high-value-added primary amines, which could be a promising candidate for the industrial production of amines.
研究领域:
催化化学
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生物质转化
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绿色化学
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DOI
NEW JOURNAL OF CHEMISTRY
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2021
·Vol. 45
·期 9
·4236-4245
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IF 3.591
Jia Zhang,Jian Yang,Junying Tian,Hailong Liu,Xuemei Li,Weiguo Fang,Xun Hu,Chungu Xia,Jing Chen,Zhiwei Huang
The synthesis of useful amines from bio-based carbonyl compounds is highly desired owing to their mild reaction conditions and green sustainability. The reductive amination of bio-furfural-derived 2-hydroxytetrahydropyran (2-HTHP) to high-value-added 5-Amino-1-pentanol (5-AP) was carried out over efficient Ni–Al2O3 catalysts prepared by a co-precipitation method. Among the Ni–Al2O3 catalysts with different Ni loadings (0–100 wt%) tested, the 50Ni–Al2O3 catalyst exhibited the highest 5-AP yield of 91.3% under mild conditions of 60 °C and 2 MPa H2. This catalyst also presented good stability during a 150 h time-on-stream without appreciable deactivation. Characterization results showed that the 50Ni–Al2O3 catalyst exhibited small Ni0 nanoparticles (5.5 nm), a high reduction degree (up to 95%), and a large amount of strong Lewis acid sites. The cooperative catalysis of the strong Lewis acid sites and highly dispersed metallic Ni sites is suggested to play an important role in achieving high efficiency in 2-HTHP reductive amination.
研究领域:
催化化学
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绿色化学
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产品关联
DOI
高影响因子
Green Chemical Engineering
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2023
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IF 0
Jian Yang,Jia Zhang,Enrico Benassi,Xuemei Li,Hailong Liu,Weiguo Fang,Junying Tian,Chungu Xia,Zhiwei Huang
Al 2 O 3 -supported monometallic Ni, Co, and bimetallic Ni–Co nanocatalysts originated from layered double hydroxide precursors were synthesized by co-precipitation method, and used for the synthesis of useful 5-amino-1-pentanol (5-AP) and 1,5-pentanediol (1,5-PD) by reductive amination (RA) or direct hydrogenation of biofurfural-derived 2-hydroxytetrahydropyran (2-HTHP), respectively. In both reactions, the yield of the target products decreased monotonously with the increasing amounts of Co in the NiCo/Al 2 O 3 catalysts, owing probably to the replacement of highly reactive Ni by Co component with inferior hydrogenation activity at the low reaction temperature of 60 °C. However, the incorporation of Co could improve the reducibility of the NiCo/Al 2 O 3 bimetallic catalysts and promote the reaction stability of the catalysts, especially for Ni 2 Co 1 /Al 2 O 3 , in both reactions with over 180 h time-on-stream. Characterization of the catalysts before and after the reaction showed that the incorporating Co could inhibit the sintering of metal particles and hinder the surface oxidation of the more reactive Ni 0 species, thanks to the formation of Ni–Co alloy in the bimetallic catalysts. DFT-based modeling of the reaction mechanisms is also performed, supporting the reaction pathway proposed previously and also the much higher activity of Ni in the RA of 2-HTHP as compared with Co.
研究领域:
化学工程
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催化材料科学
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DOI
Arabian Journal of Chemistry
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2022
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IF 6.212
Zizhen Zhao,Chen Fu,Yuping Zhang,Yingying Zhang,Xiaoxi Yang,Ailing Fu
The incidence of HCC continues to increase rapidly in recent years. the principle of developing anti-HCC drugs is to specifically kill tumor cells, without affecting the function of normal cells. Here we synthesized a novel protonic compound bis(5-amino-1,10-phenanthroline) (P-BAP), and the antitumor activity was explored in vitro and in vivo . The results showed that P-BAP could selectively inhibit the proliferation of tumor cells, and induce HCC apoptosis. In HCC-bearing mice, P-BAP could effectively retard the tumor growth, even completely eliminate the tumors at the dose of 5 mg/kg, and meanwhile P-BAP had no significant effect on mouse body weight. Mechanism analysis revealed that P-BAP could down-regulate the protein expressions of pleomorphic adenoma gene like-2 (PLAGL2), HIF-1α and β-catenin, and up-regulate the levels of pro-apoptotic protein BAX and BNIP3. In addition, P-BAP could reduce mitochondrial respiratory chain complex activities, leading to insufficient ATP production. The study provides a new approach for designing selective antitumor drugs, and suggests that P-BAP would be a potential candidate for HCC therapy.
研究领域:
肿瘤学
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药理学
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分子生物学
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DOI
高影响因子
SENSORS AND ACTUATORS B-CHEMICAL
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2019
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IF 6.393
Tianyi Zhang,Si Dong,Feifei Zhao,Mingxiao Deng,Yuqin Fu,Changli Lü
Recently, fluorescent pH test paper has been extensively explored for visual assays due to its easy preparation, low-cost, and portable feature. In addition, intracellular pH also plays important roles in different pathological and physiological processes for understanding cellular functions and providing critical assistance for early disease diagnosis. Herein, the tricolor emission [email protected] carbon dots (CDs) were synthesized via one-pot hydrothermal method using 5-amino-1,10-phenanthroline (Aphen) and citric acid (CA) as the carbon sources. The fluorescence emission of CDs showed an interesting pH dependence due to the special structure and properties, which can make the CDs to be used as the pH test paper to qualitatively and quantitatively detect pH value in a wide pH range. At the same time, because of good cell compatibility and low toxicity, CDs can be used as a new type of cell imaging marker to detect intracellular pH. The unique tricolor emission property of CDs can well avoid the fluorescent dyes and protein fluorescence interference.
研究领域:
材料科学
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分析化学
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生物医学工程
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细胞生物学
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产品关联
DOI
高影响因子
SENSORS AND ACTUATORS B-CHEMICAL
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2019
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IF 6.393
Feifei Zhao,Tianyi Zhang,Qian Liu,Changli Lü
For most of the carbon dots (CDs), solid-state fluorescence and room temperature phosphorescence (RTP) are difficult to achieve due to self-quenching and intersystem crossing (ISC) limitations. Here, nitrogen-doped CDs-1 showing both fluorescence and RTP was obtained by hydrothermal reaction from polyvinyl alcohol (PVA) and 5-amino-1,10-phenanthroline (Aphen). The CDs-1 emits blue-green fluorescence in aqueous solution, while emits white fluorescence and yellow-green RTP in the solid state with a RTP lifetime up to 103 ms, exhibiting a long afterglow with a duration of 3 s, which is visible to the naked eyes. The RTP of the CDs-1 is derived from the C N/C N in Aphen and C N/CN in Aphen and C O produced during the carbonization process with a small energy gap between the singlet and triplet states, which helps to realize the ISC. At the same time, the hydrogen bonds between the C N/CN or CO bonds and O H of the not completely carbonized PVA chains on the CDs-1 surface have the advantages of moisture resistance, oxygen barrier and improving the rigidity of CDs-1. Eventually, non-radiative transitions can be suppressed. Based on the decent fluorescence properties, the aqueous solution of CDs-1 can be used to detect TNP and is responsive to pH with a good linear relationship between acid and alkali. In addition, the RTP of CDs-1 can be utilized as banknote anti-counterfeiting material under a long excitation wavelength. This work provides a possibility to realize the multi-mode illumination regulation of CDs by facile one-step strategy.
研究领域:
材料科学
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化学
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纳米技术
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分析化学
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光学材料
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产品关联
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
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2020
·
IF 7.632
Xuemei Li,Junying Tian,Hailong Liu,Xun Hu,Jia Zhang,Chungu Xia,Jing Chen,Haichao Liu,Zhiwei Huang
The reductive amination (RA) of 2-hydroxytetrahydropyran (2-HTHP) produced from biofurfural-derived dihydropyran provides a new efficient process for the clean synthesis of valuable 5-amino-1-pentanol (5-AP). Among various solid catalysts tested, the inexpensive Ni–Mg3AlOx catalysts derived from hydrotalcite precursors were found to be very active and selective, especially at Ni loadings above 20 wt %. A 85% total yield of 5-AP was obtained from dihydropyran on 40Ni–Mg3AlOx, the catalyst with the highest 2-HTHP RA activity among the Ni–Mg3AlOx catalysts, under mild conditions of 60 °C and 2 MPa H2. Characterization results showed that the reducibility of the calcined NiO-Mg3AlOx samples increased with increasing Ni loading from 5 to 50 wt %, while the Ni0 crystallite sizes exhibited a minimum of 4.8 nm on 40Ni–Mg3AlOx after reduction in H2 at 750 °C. The volcanic changes of 5-AP generation rate/yield with increasing Ni loading of the Ni–Mg3AlOx catalysts and with rising prereduction temperature of 30Ni–Mg3AlOx catalyst in 2-HTHP RA indicate that the balance of the reducibility and Ni0 particle size of the catalysts played an important role in obtaining high 5-AP yields. The 30Ni–Mg3AlOx catalyst showed a good stability in 2-HTHP RA examined in a continuous flow reactor over a 90 h time-on stream.
研究领域:
化学工程
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催化
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绿色化学
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生物化工
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产品关联
DOI
高影响因子
Molecular Catalysis
·
2023
·
IF 4.6
Shuxing Zhang,Jiali Zheng,Zhihui Li,Xiaoshu Ding,Yanji Wang
Herein, we reported a green catalytic reaction system for the synthesis of 5-amino-1-pentanol with furfural and ionic liquid hydroxylamine salt as the initial raw material. In addition, the method can obtain 2-furonitrile and furfurylamine in high yields. The reaction system comprises three new reactions, including the reaction of furfural with ionic liquid hydroxylamine salt to synthesize 2-furonitrile, the hydrogenation of 2-furonitrile to prepare furfurylamine, and the hydrogenolysis of furfurylamine to prepare 5-amino-1-pentanol. For the synthesis of 2-furonitrile, ionic liquid hydroxylamine salt (NH 2 OH) 2 ·[HSO 3 - b - mim ]·HSO 4 was prepared. The ionic liquid as co-solvents, catalysts, and hydroxylamine stabilizer has recovery and reusability. For the hydrogenation of 2-furonitrile to furfurylamine, high-efficiency Ru/g-C 3 N 4 catalyst was prepared. For the hydrogenolysis of furfurylamine to 5-amino-1-pentanol, high-efficiency Pt/ZrO 2 catalyst was prepared. Finally, the yield of 5-amino-1-pentanol based on furfural was 48.7%. A potential pathway for preparing drugs from biomass has been identified in this work.
研究领域:
化学工程
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催化
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绿色化学
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有机合成
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生物质转化
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产品关联
DOI
高影响因子
INORGANICA CHIMICA ACTA
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2013
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IF 1.687
Yan-Jing Gu,Bing Yan
The synthesis of organics 9-hydroxyphenalenone (HPO), 2-methyl-9-hydroxyphenalenone (MHPO), 6-hydroxybenz[de]anthracen-7-one (HBAO), 5-amino-1,10-phenanthroline (phen-NH 2 ) and its functionalized mesoporous MCM-41 by covalent band are reported, as well as those of Europium (III) hybrid mesoporous materials, EuL 3 phen-MCM-41 (L = HPO, MHPO, HBAO). The photoluminescence and microstructural properties are characterized, and the XRD and BET results revealed that all of these hybrid materials have uniformity in the mesostructure. It is worth noting that the excitation spectra of these hybrid materials have a broad absorption, which occupies from UV to visible region (250–475 nm). Upon ligand-mediated excitation with the visible light, the low efficient energy transfer exhibit between the organic ligands and europium(III) ion under visible excitation, but the maximum wavelength (456 nm/457 nm/451 nm) located at blue light region, which is in consistent with the blue LED light, then might be a feasible alternative in producing time-resolved luminescence under LED-excitation.
研究领域:
材料科学
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化学
·
光电技术
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）