Natural vs. Synthetic Phosphate as Efficient Heterogeneous Compounds for Synthesis of Quinoxalines
Natural phosphate (NP) and synthetic fluorapatite phosphate (SFAP) were proposed as stable, inexpensive, readily available and recyclable catalysts for the condensation of 1,2-diamines with 1,2-dicarbonyls in methanol to afford quinoxaline at room temperature. NP provided as high as 92–99% yield for...
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MDPI AG
2021-12-01
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| Series: | International Journal of Molecular Sciences |
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| author | Abbas Amini Azadeh Fallah Ahmad Sedaghat Ahmad Gholami Chun Cheng Anju R. Gupta |
| author_facet | Abbas Amini Azadeh Fallah Ahmad Sedaghat Ahmad Gholami Chun Cheng Anju R. Gupta |
| author_sort | Abbas Amini |
| collection | DOAJ |
| description | Natural phosphate (NP) and synthetic fluorapatite phosphate (SFAP) were proposed as stable, inexpensive, readily available and recyclable catalysts for the condensation of 1,2-diamines with 1,2-dicarbonyls in methanol to afford quinoxaline at room temperature. NP provided as high as 92–99% yield for quinoxalines in short reaction times (i.e., 1–45 min), while SFAP created quinoxalines with 87–97% yield in 60–120 min. From the chemical analyses, X-ray fluoresecency, X-ray diffraction, energy dispersive X-ray and Fourier-transform infrared spectroscopy methods, two main phases (CaO, P<sub>2</sub>O<sub>5</sub>) appeared in NP together with other low content phases (SiO<sub>2</sub>, Fe<sub>2</sub>O<sub>3</sub>). Compared to other phases, apatite (CaO and P<sub>2</sub>O<sub>5</sub> as Ca10(PO<sub>4</sub>)<sub>6</sub>) played a major role in the catalytic activity of NP. SFAP with similar Ca/P atomic ratio showed a relatively lower catalytic activity than NP for the condensation of 1,2-diamine with 1,2-dicarbonyl in methanol at ambient temperature. To investigate the recyclability of catalysts, the surface properties of NP and 6-recycled NP were investigated using scanning electron microscopy, energy dispersive X-ray and Brunauer–Emmett–Teller and Barrett–Joyner–Halenda methods. Some differences were observed in NP and 6-recycled NP’s particle size, surface area, the volume and size of pores, and the content of elements; nevertheless, the use–reuse process did not noticeably change the catalytic property of NP. |
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| publishDate | 2021-12-01 |
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| series | International Journal of Molecular Sciences |
| spelling | doaj.art-21444745f87b4eb192854383f42cb8eb2023-11-23T08:49:43ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-12-0122241366510.3390/ijms222413665Natural vs. Synthetic Phosphate as Efficient Heterogeneous Compounds for Synthesis of QuinoxalinesAbbas Amini0Azadeh Fallah1Ahmad Sedaghat2Ahmad Gholami3Chun Cheng4Anju R. Gupta5Centre for Infrastructure of Engineering, Bld Z, Locked Bag 1797, Kingswood Campus, Western Sydney University, Penrith, NSW 2751, AustraliaDepartment of Chemistry, Payame Noor University, Tehran 19395-4697, IranDepartment of Mechanical Engineering, Australian College of Kuwait, Mishref, Safat 13015, KuwaitPharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz 71348-14336, IranDepartment of Materials Science and Engineering, Southern University of Science and Technology (SUSTech), Shenzhen 518055, ChinaDepartment of Mechanical Engineering, Industrial and Manufacturing Engineering, The University of Toledo, Toledo, OH 43606, USANatural phosphate (NP) and synthetic fluorapatite phosphate (SFAP) were proposed as stable, inexpensive, readily available and recyclable catalysts for the condensation of 1,2-diamines with 1,2-dicarbonyls in methanol to afford quinoxaline at room temperature. NP provided as high as 92–99% yield for quinoxalines in short reaction times (i.e., 1–45 min), while SFAP created quinoxalines with 87–97% yield in 60–120 min. From the chemical analyses, X-ray fluoresecency, X-ray diffraction, energy dispersive X-ray and Fourier-transform infrared spectroscopy methods, two main phases (CaO, P<sub>2</sub>O<sub>5</sub>) appeared in NP together with other low content phases (SiO<sub>2</sub>, Fe<sub>2</sub>O<sub>3</sub>). Compared to other phases, apatite (CaO and P<sub>2</sub>O<sub>5</sub> as Ca10(PO<sub>4</sub>)<sub>6</sub>) played a major role in the catalytic activity of NP. SFAP with similar Ca/P atomic ratio showed a relatively lower catalytic activity than NP for the condensation of 1,2-diamine with 1,2-dicarbonyl in methanol at ambient temperature. To investigate the recyclability of catalysts, the surface properties of NP and 6-recycled NP were investigated using scanning electron microscopy, energy dispersive X-ray and Brunauer–Emmett–Teller and Barrett–Joyner–Halenda methods. Some differences were observed in NP and 6-recycled NP’s particle size, surface area, the volume and size of pores, and the content of elements; nevertheless, the use–reuse process did not noticeably change the catalytic property of NP.https://www.mdpi.com/1422-0067/22/24/13665heterogeneous catalystnatural phosphatefluorapatitequinoxalinesapatitenano-bio-chemistry |
| spellingShingle | Abbas Amini Azadeh Fallah Ahmad Sedaghat Ahmad Gholami Chun Cheng Anju R. Gupta Natural vs. Synthetic Phosphate as Efficient Heterogeneous Compounds for Synthesis of Quinoxalines International Journal of Molecular Sciences heterogeneous catalyst natural phosphate fluorapatite quinoxalines apatite nano-bio-chemistry |
| title | Natural vs. Synthetic Phosphate as Efficient Heterogeneous Compounds for Synthesis of Quinoxalines |
| title_full | Natural vs. Synthetic Phosphate as Efficient Heterogeneous Compounds for Synthesis of Quinoxalines |
| title_fullStr | Natural vs. Synthetic Phosphate as Efficient Heterogeneous Compounds for Synthesis of Quinoxalines |
| title_full_unstemmed | Natural vs. Synthetic Phosphate as Efficient Heterogeneous Compounds for Synthesis of Quinoxalines |
| title_short | Natural vs. Synthetic Phosphate as Efficient Heterogeneous Compounds for Synthesis of Quinoxalines |
| title_sort | natural vs synthetic phosphate as efficient heterogeneous compounds for synthesis of quinoxalines |
| topic | heterogeneous catalyst natural phosphate fluorapatite quinoxalines apatite nano-bio-chemistry |
| url | https://www.mdpi.com/1422-0067/22/24/13665 |
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