ACS Sustainable Chemistry & Engineering
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2018
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IF 6.14
Guiling Shi,Kaihong Chen,Yongtao Wang,Haoran Li,Congmin Wang
Ionic liquids can be designed by varying a great deal of anions and cations offering efficient CO2 capture or CO2 utilization. Generally, the anion played a key role, but the cation did not have a significant impact. Here, a strategy for rational design of functionalized ionic liquids for efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 has been developed through tuning the cations of aprotic ionic liquids. The basicity of cation affects its catalytic activity dramatically and the hydrogen bond from cation can promote this reaction. Then, hydroxyl functionalized ionic liquid [Ch][Im] was designed, which exhibited the best catalytic activity in this reaction. Through the combination of quantum-chemical calculations, NMR spectroscopic investigations, and controlled experiments, the results indicate that in situ generated [Ch][Im]-CO2 complex is the real catalyst. Furthermore, aprotic IL [Ch][Im] exhibits good generality and reuseability. Remarkably, quinazoline-2,4(1H,3H)-dione can also be obtained under simulated flue gas system on a gram scale with excellent yield using [Ch][Im] as catalyst. As we know, this is the first time that obtains quinazoline-2,4(1H,3H)-dione in excellent yield under flue gas condition.
研究领域:
化学
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材料科学
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产品关联
DOI
高影响因子
Reaction Chemistry & Engineering
·
2022
·Vol. 7
·期 9
·1968-1977
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IF 5.2
Yu Chen,Chong Liu,Yaoting Duan,Dongkun Yu,Zhenghui Liu,Yuting Li,Ruifen Shi,Yuting Guo,Tiancheng Mu
Highly efficient and sustainable conversion of CO2 into quinazoline-2,4(1H,3H)-dione at room temperature and atmospheric pressure is challenging. Deep eutectic solvents (DESs) are considered as the green solvents of the 21st century, which are also designable with high tunability and high atom efficiency. Here, DESs are for the first time used to catalyze the CO2 conversion into quinazoline-2,4(1H,3H)-dione at room temperature and atmospheric pressure with high efficiency and nearly 100% yield. This work provides a sustainable way for the efficient conversion of CO2 into quinazoline-2,4(1H,3H)-dione by DESs at room temperature and atmospheric pressure.
研究领域:
化学
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环境科学
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可持续发展
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DOI
高影响因子
CHINESE JOURNAL OF CHEMICAL ENGINEERING
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2023
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IF 3.8
Bowen Jiang,Meiling Weng,Jigang An,Yuewei Fan,Jia Liu,Ying Liu,Ting Yu,Leizhi zheng,Guoqiang Yang,Zhibing Zhang
The transformation of CO 2 into high value-added product is a promising pathway for utilizing CO 2 . However, the process tends to require harsh reaction conditions owing to CO 2 chemical inertness. Designing a high efficiency catalytic system with environmentally benign characteristic are important determinants. In this work, protic ionic liquids [TMG][2-OPy] were prepared via one-step neutralization between 1,1,3,3-tetramethylguanidine and 2-hydroxypyridine, applying to the domain of synthesizing quinzoline-2,4(1H , 3H) - diones from CO 2 and 2-aminobenzontiles without any solvent or metal, achieving the yield of 97% at 90 °C for 8 h under atmospheric. A series of substrates with good to acceptable yield were detected, revealing the generality and universality of the catalyst. Furthermore, the system could be facilely reused for at least six runs, retaining the yield of 94%. A preliminary kinetic equation is calculated with the activation energy of 68 kJ·mol −1 , and a plausible reaction mechanism was put forward. This study highlights that the [TMG][2-OPy] enables to activate CO 2 carboxylation efficiently.
研究领域:
化学
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环境科学
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DOI
高影响因子
Canadian Journal of Chemistry
·
2018
·Vol. 97
·期 3
·
IF 1.084
Guo-Ying Zhao,Ling-Ling Mu,Latif Ullah,Meng Wang,Hong-Ping Li,Xin-Xin Guan
In this study, pharmaceutically relevant quinazoline-2,4(1H,3H)-diones were synthesized eco-efficiently by cycloaddition of CO2 and 2-aminobenzonitrile in water, catalyzed by melamine as a thermoregulated catalyst. Quinazoline-2,4(1H,3H)-dione was produced selectively with 92% yield at 120 °C, 4.2 MPa, and automatically separated from the hot catalytic aqueous solution, which was reused directly for several runs until its activity decreased in an obvious manner. Then, the catalyst melamine was recrystallized from the spent aqueous solution via simple cooling and reused for another several catalytic runs. The efficient valorization of CO2 and the straightforward stepwise recovery of the products and catalyst were important to save energy and minimize process waste for the practical industrial production.
研究领域:
有机化学
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绿色化学
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产品关联
DOI
高影响因子
NEW JOURNAL OF CHEMISTRY
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2019
·Vol. 43
·期 41
·16164-16168
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IF 3.069
Shangqing Chen,Zheng Wang,Jiayin Hu,Yafei Guo,Tianlong Deng
The readily available ZnI2/NEt3 system was used firstly to catalyze the transformation of CO2 and 2-aminobenzonitriles into quinazoline-2,4(1H,3H)-diones at room temperature and low CO2 pressure in high yields. Further experiments indicated that this ZnI2/NEt3 system has excellent effects on activating both amino and cyano groups.
研究领域:
有机化学
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催化化学
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DOI
高影响因子
ACS Sustainable Chemistry & Engineering
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2020
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IF 7.632
Fusheng Liu,Ran Ping,Yongqiang Gu,Penghui Zhao,Bin Liu,Jun Gao,Mengshuai Liu
CO2 capture and utilization (CCU) have aroused much attention. In this paper, several novel triazolium-based ionic liquids (ILs) were developed for highly efficient transformation of CO2 into quinazoline-2,4(1H,3H)-diones. The catalytic behaviors such as the effects of IL structures and reaction parameters, catalyst recyclability, and scope of substrates were studied in detail. As compared to the reported homogeneous and heterogeneous catalysts, the [HTMG][Triz] with a tetramethylguanidine cation and a triazole anion exhibited an exceptional activity at 50 °C and 1 atm CO2 without any organic solvents. On the basis of the CCU strategy, we first studied the equimolar CO2 capture by the [HTMG][Triz] and one pot conversion of activated CO2 into various quinazoline-2,4(1H,3H)-diones, and good to excellent product yields were obtained. In addition, the catalytic performance for synthesis of quinazoline-2,4(1H,3H)-dione under low concentration of CO2 using a simulated flue gas was studied. The developed triazolium-based ILs could realize simultaneous activation of CO2 and the substrates under ambient conditions, which also have been demonstrated to support the reaction mechanism well. The integrative protocol here shows great significance in the practical synthesis of quinazoline-2,4(1H,3H)-dione and their derivatives from captured CO2 waste under mild conditions.
研究领域:
化学工程
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环境科学
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有机合成
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产品关联
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
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2021
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IF 8.198
Ran Ping,Penghui Zhao,Qianqian Zhang,Guangyu Zhang,Fusheng Liu,Mengshuai Liu
Novel aminophenol-based protic ionic liquids (APILs) were designed and synthesized via one-step neutralization, and they were used as catalysts for conversion of 2-aminobenzonitriles and CO2 from simulated flue gases to produce quinazoline-2,4(1H,3H)-diones under mild conditions. The effects of anion–cation structures of APILs, various solvents, reaction parameters, and water contents on the product yields were investigated in detail. The catalyst recyclability and general applicability to different substrates were examined. It showed that both the basicity of the reaction media and the synergistic activation of zwitterions to reactants played important roles during the catalysis. The optimum [HTMG][m-AP] catalyst cooperating with the dimethylformamide (DMF) solvent could selectively convert CO2 into various quinazoline-2,4(1H,3H)-diones with good to excellent product yields at 60 °C and in a 0.1 MPa simulated flue gas atmosphere. In addition, [HTMG][m-AP]/DMF was easily recycled and could be reused in up to five consecutive cycles without an obvious loss of activity. By comparison with the reported catalysts, [HTMG][m-AP]/DMF here showed a superior catalytic performance and a great potential for development. Finally, the activation behaviors of [HTMG][m-AP]/DMF to reactants were studied, and a synergistic catalytic mechanism was proposed.
研究领域:
化学工程
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环境科学
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产品关联
DOI
高影响因子
CHEMICAL ENGINEERING JOURNAL
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2023
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IF 15.1
Guokai Cui,Yisha Xu,Daqing Hu,Ying Zhou,Chunliang Ge,Huayan Liu,Wenyang Fan,Zekai Zhang,Biao Chen,Quanli Ke,Yaoji Chen,Bing Zhou,Wei Zhang,Ruina Zhang,Hanfeng Lu
A series of functional ionic deep eutectic solvents (iDESs) containing pyridinolate anions were reported as green sorbents , solvents, and catalysts for highly efficient capture and transformation of CO 2 to quinazoline-2,4(1 H ,3 H )-dione and its derivatives at mild conditions via tuning the structures of iDESs. Physical properties, such as density and viscosity, as well as flow activation energy and thermal expansion coefficient, were systematically investigated. Effects of the partial pressure of CO 2 and the absorption temperature on the CO 2 absorption capacity using these functional iDESs as sorbents were studied, and the different absorption mechanisms, including carbamate and carbonate pathways, were analyzed by FT-IR and 13 C NMR spectroscopy. Additionally, thermodynamics analysis of CO 2 absorption was performed according to the chemical reaction mechanism, and K θ ,Δ r G θ m), Δ r H θ m, and Δ r S θ m were calculated. Furthermore, the effects of cations, anions, HBDs, reaction temperature, and the molar ratio of catalyst to substrate ( n Cat. / n Sub . ) on CO 2 conversion were systematically studied, and excellent isolated yield of up to 97.1% at mild conditions could be obtained with only 0.25 equiv. DES as the solvent as well as the sorbent and the catalyst. Plausible “simultaneous CO 2 activation and substrate activation” reaction mechanism of capture and transformation of CO 2 to quinazoline-2,4(1 H ,3 H )-diones by [N 2222 ][4-PyO]/DMSO (1:4) was verified by the spectra of FT-IR and based on previous reports. To the best of our knowledge, these are the first examples of tuning functional iDESs for the capture and transformation of CO 2 to quinazoline-2,4-(1 H ,3 H )-dione and its derivatives with only 0.25 equiv. DES. The method may also open a door to obtain the high efficiency of capture and transformation of such gases as NO x , SO 2 , CO, H 2 S, and CO 2 by functional DESs.
研究领域:
化学工程
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环境科学
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催化化学
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产品关联
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
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2022
·
IF 9.224
Tingting Chen,Yunfei Zhang,Yingjie Xu
A novel basic anion-functionalized ionic liquid with a 1-methylhydantoin anion ([1-MHy]−) and [P4442]+ cation was synthesized for efficient CO2 capture and catalytic conversion of CO2 to quinazoline-2,4(1H,3H)-dione, and CO2 absorption and conversion mechanisms were investigated by NMR, FT-IR, and DFT calculations. CO2 absorption results show that the capture capacity of [P4442][1-MHy] at 303.15 K and 0.1 MPa is up to 1.58 molCO2/molIL, which is attributed to the multiple-site cooperative interactions between CO2 with N– and C═O of [1-MHy]− originated from the electron conjugation effect, resulting in a decrease in the CO2 absorption enthalpy (−51.4 kJ/mol) and an increase in the activation of CO2. Moreover, the high yield of quinazoline-2,4(1H,3H)-dione obtained by using [P4442][1-MHy] to catalyze 2-aminobenzonitrile with atmospheric-pressure CO2 was 97% and is solvent- and metal-free. The reaction mechanism indicates that [1-MHy]− with the multiple-site cooperative interactions can not only activate CO2 but also can activate 2-aminobenzonitrile by forming two types of hydrogen bonds with −NH2 (N–H···N– and N–H···O═C), thus ensuring the excellent catalytic performance of [P4442][1-MHy]. Furthermore, due to the similar basicity of [1-MHy]− to the quinazolide anion ([Quinazolide]−), it can effectively prevent the deprotonation of the acidic quinazoline-2,4-dione into [Quinazolide]−, thereby improving its yield. In addition, [P4442][1-MHy] has good recycling performance during CO2 capture and conversion. The physicochemical properties of [P4442][1-MHy] are also reported. The obtained results may provide a new strategy for converting CO2 into value-added chemicals under green conditions.
研究领域:
化学工程
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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
JOURNAL OF HETEROCYCLIC CHEMISTRY
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2023
·
IF 2.4
Ping Zhao,Qingle Zeng
We have developed a diversity-oriented, substrate-controlled, chemoselective synthetic method for a variety of structurally diverse 1-sulfonylquinazoline-2,4(1H,3H)-diones and 2-sulfonamidobenzonitriles. This substrate-controlled synthesis is accomplished through the condensation reaction of 2-(sulfonamido)benzamides with or without an N-methyl group on the amides. The reactions are fulfilled within half an hour at room temperature with solid triphosgene as a convenient condensing agent and pyridine as an acid acceptor. This protocol features easily available starting materials, mild reaction conditions, easy experimental operation, and moderate to excellent yields of products.
研究领域:
有机化学
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药物化学
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DOI
高影响因子
SEPARATION AND PURIFICATION TECHNOLOGY
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2024
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IF 8.1
Litian Wang,Jie Chen,Shuai Wang,Tongyao Zhou,Dan Li,Cuiping Li,Lirong Qian,Yang Xiong,Lin Miao,Zhiyong Xie
Protic ionic liquids (PILs) have emerged as innovative solvents with significant potential for CO 2 capture and transformation, presenting a sustainable alternative to conventional methods which often involve energy-intensive processes or environmentally detrimental chemicals. Herein, a novel strategy for CO 2 capture and conversion at mild conditions using non-stoichiometric protic ionic liquids (NPILs) was demonstrated for the first time. These NPILs, employed as sorbents, solvents, and catalysts, were composed of imidazole (Im) and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) in various ratios. Correlations between the mole ratio of DBU/Im and physicochemical properties such as viscosity, conductivity, thermal stability, and the distribution of neutral and ionic species were systematically investigated. Effects of the absorption temperature and CO 2 partial pressure on the absorption capacity were also studied. Different absorption mechanisms, including carbonate and carbamate pathways, were analyzed using FT-IR and NMR spectroscopy. Moreover, the fixed CO 2 could be catalytically converted to quinazoline-2,4(1H,3H)-diones under exceptionally mild reaction conditions (1 atm, 50 °C, metal-free process). A plausible reaction mechanism involving simultaneous CO 2 activation and substrate activation for the transformation of CO 2 into quinazoline-2,4(1H,3H)-diones was verified through NMR spectra. It is believed that the new insights into the CO 2 mechanism will facilitate the rational design of functional ionic liquids for CO 2 capture, utilization, and storage in the future.
研究领域:
化学
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环境科学
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材料科学
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催化
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DOI
高影响因子
危险品化学品经营许可证（带存储）