Rapid formation of N-nitrosamines from nitric oxide in the presence of silver(I) salts

Abstract

N-Nitrosamines form rapidly from NO and secondary amines in the presence of AgI salts via amino radical cation intermediates derived from AgII-amine complexes.WE have shown1 that NO is an ineffectual reagent for the N-nitrosation of amines in the absence of either oxygen or iodides including iodine itself. Activation by oxygen results from the formation of either N,O, or N,O,la and by iodides from the formation of NOI.l1, Other work has shown that the N-nitrosation of amines by NO may also be catalysed by CuII and FelII salts., These reactions, which

Ammonia Retention in Biowaste via Low-Temperature-Plasma-Synthesized Nitrogen Oxyacids: Toward Sustainable Upcycling of Animal Waste

“…This is possible from a stoichiometric standpoint because there was approximately twice as much NO as NO 2 in the inlet stream and approximately twice as much NO as NO 2 in the outlet stream. Both species are very reactive. , It could be that the NO x species react quickly in a thin film at the liquid surface in accordance with eq , as suggested previously . This transport limitation would further reduce the likelihood to react with other species to form compounds like nitrosamines .…”

“…Both species are very reactive. , It could be that the NO x species react quickly in a thin film at the liquid surface in accordance with eq , as suggested previously . This transport limitation would further reduce the likelihood to react with other species to form compounds like nitrosamines . Compared to previous reports, it is notable that there is no hydrogen peroxide or ozone observed in the air–plasma effluent in this work; hydrogen peroxide could oxidize nitrite to nitrate, which can explain the lack of nitrate.…”

Pathways for N-Nitroso Compound Formation: Secondary Amines and Beyond

“…102 Copper and silver salts have also been observed to promote the Nnitrosation of secondary amines with NO. 16,17,103 Alternatively, Nudelman and Bonatti reported the synthesis of nitrosamines with NO (g) at atmospheric pressure. The Nnitroso dialkyl amine formation is affected by the temperature, with the highest yields being obtained at the lowest temperature of −78 °C (Scheme 63).…”

“…Although water increases the amount of HI formed, it also inhibits the iodine-promoted nitrosamine formation by hydrolysis of the active nitrosyl iodide to nitrous acid and hydroiodic acid . Copper and silver salts have also been observed to promote the N -nitrosation of secondary amines with NO. ,, …”

Copper(ii)-catalyzed oxidative N-nitrosation of secondary and tertiary amines with nitromethane under an oxygen atmosphere

“…1 The nitrosation of amines with nitrous acid that is generated from sodium nitrite and an acid represents a classic approach to the synthesis of N-nitrosamines. 2 In addition to this procedure, others have been reported using a nitroso source involving alkyl nitrites (RO-NQO), 3 nitrosyl chloride (Cl-NQO), 4 nitrosonium tetrafluoroborate (NOBF 4 ), 5 thiol-N 2 O 4 , 6 nitrogen oxides (N 2 O 3 or N 2 O 4 ), 7 oxyhyponitrite (N 2 O 3 2À ), 8 NO under an O 2 atmosphere, 9 Fremy's salt, 10 LiNH 2 -NO, 11 [NO + -18-crown-6-H(NO 3 ) 2 ], 12 NaNO 2 -SnCl 4 , 13 NO-AgNO 3 , 14 and bromonitromethane (BrCH 2 NO 2 ). 15 Also during the last decade, a heterogeneous catalytic system has been widely developed using a combination of either sodium nitrate or nitrogen tetroxide and a catalyst support: NaNO 2 -SiO 2 -trichloroisocyanuric acid, 16 NaNO 2 -SiO 2 -OSO 3 H on SiO 2 , 17 NaNO 2 -Nafion-H on SiO 2 , 18 N 2 O 4 supported on PVP, 19 N 2 O 4 -charcoal, 20 nitrite ionic liquid, 21 and NaNO 2 -molybdate sulfuric acid.…”