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6 the Oxidation of 3-Picoline to Nicotinic Acid with Vanadyl Pyrophosphate Catalyst
Alma Mater Studiorum - Università di Bologna DOTTORATO DI RICERCA IN CHIMICA Ciclo XXVIII Settore concorsuale di afferenza: 03/C2 Settore scientifico disciplinare: CHIM/04 SUSTAINABLE CATALYTIC PROCESS FOR THE SYNTHESIS OF NIACIN Presentata da Massimiliano Mari Coordinatore dottorato Relatore Prof. Aldo Roda Prof. Fabrizio Cavani Esame finale anno 2016 Niacin Nicotinates production 2-methylglutaronitrile -picoline oxidation Vanadia-zirconia catalyst Zirconium pyrovanadate Vanadyl pyrophosphate in-situ Raman spectroscopy Abstract Nicotinic acid (niacin) is an important vitamin of the B group, with an annual production close to 40,000 tons. It is used in medicine, food industry, agriculture and in production of cosmetics. Older industrial processes have drawbacks such as a low atomic efficiency and the use of toxic catalysts or stoichiometric oxidants. Several studies were carried out during latest years on new technologies for the synthesis of niacin and nicotinate precursors, such as 3-picoline and pyridine-3-nitrile. This thesis reports about the results of three different research projects; the first was aimed at the study of the one-step production of pyridine-3-nitrile starting from 2-methylglutaronitrile, the second at acetaldehyde/acetonitrile condensation for 3-picoline synthesis, and the third at investigating the reactivity of supported vanadium oxide catalysts for the direct gas-phase oxidation of 3-picoline with air; this process would be more sustainable compared to both older ones and some of those currently used for niacin production. For the first two research projects, a catalysts screening was carried out; however, results were not satisfactory. The third project involved the preparation, characterisation and reactivity testing of different zirconia- supported V2O5 catalysts. -
United States Patent Office Patented Feb
3,644,380 United States Patent Office Patented Feb. 22, 1972 1. 2 tion reaction such that the nitrile group farthest from the - 3,644,380 halomethyl group reacts with that group, displacing the PREPARATION OF 3-CYANOPYRIDINE halogen (X) and forming VI where R is H and VII Ronald Harmetz, Dover, and Roger J. Tull, Metuchen, where R is X. N.J., assignors to Merck & Co., Inc., Rahway, N.J. HR is eliminated from each of these compounds form No Drawing. Filed Nov. 24, 1969, Ser. No. 879,519 ing the desired 3-cyanopyridine. The elimination is car at, C. C07d 31/46 ried out by treatment with alkali in the case where R is U.S. C. 260-294.9 8 Claims equal to halogen and catalytically in the case where R is equal to hydrogen. In accordance with one embodiment of our invention, ABSTRACT OF THE DISCLOSURE O 2-methyleneglutaronitrile is halogenated by reaction with A process for preparing 3-cyanopyridine which com chlorine, bromine or iodine to obtain the corresponding prises the steps of reacting 2-methyleneglutaronitrile with 2-halo-2-halomethylglutaronitrile which is then cyclized chlorine, bromine or iodine and reacting said 2-halo-2- by reaction with a Lewis acid and the resulting reaction halomethylglutaronitrile with a Lewis acid producing the product is treated with a base to produce the desired 3 intermediate compound, 3-halo-dihydro-3-cyano-pyridine 5 cyanopyridine. wherein the latter compound undergoes dehydro-dehalo The halogenation is readily effected by intimately con genation when reacted with a base and converted to the tacting the nitrile with the halogen, preferably at tempera expected 3 - cyanopyridine(nicotinonitrile). -
Peter C.K. Lau Editor Quality Living Through Chemurgy and Green Chemistry Green Chemistry and Sustainable Technology
Green Chemistry and Sustainable Technology Peter C.K. Lau Editor Quality Living Through Chemurgy and Green Chemistry Green Chemistry and Sustainable Technology Series editors Prof. Liang-Nian He, State Key Lab of Elemento-Organic Chemistry, Nankai University, Tianjin, China Prof. Robin D. Rogers, Department of Chemistry, McGill University, Montreal, Canada Prof. Dangsheng Su, Shenyang National Laboratory for Materials Science, Institute of Metal Research, Chinese Academy of Sciences, Shenyang, China; Department of Inorganic Chemistry, Fritz Haber Institute of the Max Planck Society, Berlin, Germany Prof. Pietro Tundo, Department of Environmental Sciences, Informatics and Statistics, Ca’ Foscari University of Venice, Venice, Italy Prof. Z. Conrad Zhang, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China Aims and Scope The series Green Chemistry and Sustainable Technology aims to present cutting-edge research and important advances in green chemistry, green chemical engineering and sustainable industrial technology. The scope of coverage includes (but is not limited to): – Environmentally benign chemical synthesis and processes (green catalysis, green solvents and reagents, atom-economy synthetic methods etc.) – Green chemicals and energy produced from renewable resources (biomass, carbon dioxide etc.) – Novel materials and technologies for energy production and storage (biofuels and bioenergies, hydrogen, fuel cells, solar cells, lithium-ion batteries etc.) – Green chemical engineering processes (process integration, -
Vapor Phase Photochemistry of Cyanopyridines and Pyridine
VAPOR PHASE PHOTOCHEMISTRY OF CYANOPYRIDINES AND PYRIDINE. DEUTERIUM LABELING STUDIES by Somchoke Laohhasurayotin A Dissertation Submitted to the Faculty of the WORCESTER POLYTECHNIC INSTITUTE in partial fulfillment of the requirements for the Degree of Doctor of Philosophy in Chemistry by ____________________________________________ April, 2005 APPROVED: Examining Committees ________________________________ __________________________________ Professor James W. Pavlik, Advisor Professor W. Grant McGimpsey __________________________________ Professor Venkat R. Thalladi __________________________________ Professor Richard P. Johnson University of New Hampshire ABSTRACT The vapor phase photochemistry of the three isomeric cyanopyridines and the three methylpyridines was studied by irradiating their vapors at 254 nm. It was found that direct irradiation of any one cyanopyridine isomer resulted in the formation of the other two isomers of cyanopyridine or methylpyridines respectively. The reactivity of each isomer was found to be different. This was suggested to be based on the stability of their azaprefulvene intermediates formed during interconversion. The phototransposition of these molecules was suggested to result from 2,6-bonding, nitrogen migration around the five sides of cyclopentenyl ring followed by rearomatization. This mechanism was found to be consistent with the results of deuterium labeling studies of cyanopyridines These result suggest that cyanopyridines undergo phototransposition via the intermediacy of azaprefulvenes instead of Dewar-pyridine and azaprismane. Thus, photochemical studies showed that the six trideuteriopyridine isomers constitute two separate photochemical triads. Each triad consists of three isomers that are photointerconverting upon irradiation at 254 nm in the vapor phase. Similary, it was found that the three isomeric tetradeuteriopyridine isomers also constitute a photochemical triad and are interconverting upon irradiation at 254 nm in the vapor phase.