Catalytic synthesis of niacin from 3-methyl-pyridine and 30%H₂O₂ by Cu-based zeolite

Abstract

Niacin is well known not only as vitamin B3 but also as an important chemical, and has wide applications in the fields of food, farming, medicine, pharmaceuticals, and industry. With the rapid development of human society, the requirement for niacin has been increasing constantly worldwide. Meanwhile, development of green routes to produce niacin under mild conditions has become particularly urgent to substitute the conventional reaction process with the consideration of energy conservation and emission reduction. Among various synthesis routes of niacin, selective oxidation of 3-methyl-pyridine and hydrogen peroxide (H₂O₂) in the liquid phase has become the focus of research due to its distinct advantages, such as mild reaction conditions, environmentally friendly reaction processes, and so on. Herein, zeolite-based catalysts have been first applied in the liquid phase synthesis of niacin from 3-methyl-pyridine and 30%H₂O₂ under mild reaction conditions. In addition, Cu-based 13X zeolite is found to show the highest catalytic performance, and optimal catalytic reaction systems have been established. This work provides a green and optional route for the synthesis of niacin.

Keywords

Zeolite / copper / niacin / 3-methyl-pyridine / H₂O₂

References

[1] Freese R.Niacin - a scoping review for Nordic Nutrition Recommendations 2023.Food Nutr Res2023;67: PMCID:PMC10770643

[2] Ahmadian A,Seidavi AR.A review of the effects of niacin on broiler productivity.World Poultry Sci J2021;77:589-604

[3] Rennick A,Seel L.Nicotinic acid and nicotinamide: a review of their use for hyperphosphatemia in dialysis patients.Pharmacotherapy2013;33:683-90

[4] Lanska DJ.The discovery of niacin, biotin, and pantothenic acid.Ann Nutr Metab2012;61:246-53

[5] Gasperi V,Savini I.Niacin in the central nervous system: an update of biological aspects and clinical applications.Int J Mol Sci2019;20:974 PMCID:PMC6412771

[6] Song Z,Li W.Innate pharmacophore assisted selective C–H functionalization to therapeutically important nicotinamides.Org Chem Front2019;6:1613-8

[7] Lisicki D,Orlińska B.Methods to produce nicotinic acid with potential industrial applications.Materials2022;15:765 PMCID:PMC8836525

[8] Lisicki D,Orlińska B.Oxidation of picoline with oxygen to nicotinic acid against Co²⁺, NHPI, and phosphonium or ammonium bromides.Catalysts2023;13:1271

[9] Goto Y,Murayama T.Hydrothermal synthesis of microporous W–V–O as an efficient catalyst for ammoxidation of 3-picoline.Appl Catal A Gen2016;509:118-22

[10] Jiang F,Niu L.Effect of supports on the structure and activity of vanadium-chromium oxide catalysts for ammoxidation of 3-picoline.Chinese J Catal2013;34:1833-8

[11] Kalevaru VN,Venkat Rao V.Preparation, characterisation and catalytic evaluation of MgF₂ supported V₂O₅ catalysts for ammoxidation of 3-picoline.Appl Catal A Gen2009;352:223-33

[12] Chuck R.Technology development in nicotinate production.Appl Catal A Gen2005;280:75-82

[13] Ghosh S,Sharma SK.Fabrication of Ag/Mn₃O₄ nano-architectures for the one-step selective oxidation of 3-picoline to niacin: a key to vitamin B₃ production.Catal Sci Technol2016;6:4644-54

[14] Gao ZR,Chen FJ.Interchain-expanded extra-large-pore zeolites.Nature2024;628:99-103

[15] Liu L,Yang Y.Dealuminated Beta zeolite reverses Ostwald ripening for durable copper nanoparticle catalysts.Science2024;383:94-101

[16] Yu S,Lyu JM.Engineering surface framework TiO₆ single sites for unprecedented deep oxidative desulfurization.Natl Sci Rev2024;11:nwae085 PMCID:PMC10989657

[17] Liu S,Yue B.Control of zeolite local polarity toward efficient xenon/krypton separation.J Am Chem Soc2024;146:8335-42

[18] Gong X,Wang J.Hydrophilic Ti-MWW for catalyzing epoxidation of allyl alcohol.Chem Synth2024;4:14

[19] Tai W,Wu G.A simple strategy for synthesis of b-axis-oriented MFI zeolite macro-nanosheets.Chem Synth2023;3:38

[20] Sun MH,Hu ZY.Boosting molecular diffusion following the generalized Murray’s Law by constructing hierarchical zeolites for maximized catalytic activity.Natl Sci Rev2022;9:nwac236 PMCID:PMC9828477

[21] Liu X,Chen L.Construction of Ti-containing zeolite with highly enhanced catalytic activity by active species surface implanting strategy.Catal Today2022;405-6:285-98

[22] Wang J,Chen L,Xia Q.A nucleation-tuned mechanism to prepare centre-crossed zeolite lamellas by the rotating/static switch crystallization strategy.Inorg Chem Front2022;9:889-901

[23] Chai Y,Wu G,Li L.Confinement in a zeolite and zeolite catalysis.Acc Chem Res2021;54:2894-904

[24] Chen LH,Wang Z,Xie Z.Hierarchically structured zeolites: from design to application.Chem Rev2020;120:11194-294

[25] Hu N,Liu S.Enhanced stability of highly-dispersed copper catalyst supported by hierarchically porous carbon for long term selective hydrogenation.Chinese J Catal2020;41:1081-90

[26] Peng Z,Sun M.A hierarchical zeolitic Murray material with a mass transfer advantage promotes catalytic efficiency improvement.Inorg Chem Front2018;5:2829-35

[27] Zhou D,Lu X,Li K.Co²⁺-exchanged MOR and 5A zeolites as efficient solid catalysts for the epoxidation of styrene with air.Catal Commun2014;45:124-8

[28] Kim H,Lee S.Spontaneous generation of H₂O₂ and hydroxyl radical through O₂ reduction on copper phosphide under ambient aqueous condition.Environ Sci Technol2019;53:2918-25