Hydroxylamine reaction with nitrous acid

Production of hyponitrous acid and sulfates from the reaction of hydroxylamine monosulfonate with nitrous acid. 

If primary or secondary amines are used, A/-substituted amides are formed. This reaction is called aminolysis. Hydra2ines yield the corresponding hydra2ides, which can then be treated with nitrous acid to form the a2ides used in the Curtius rearrangement. Hydroxylamines give hydroxamic acids. 

Laboratory syntheses of nitrous oxide include the decomposition of hyponitrous acid (236) or nitramide (314), the reaction of nitrous acid with hydroxylamine (146) or hydrazoic acid, (147) and the reaction of amidosulfonic acid with concentrated nitric acid (148) ... 

Reaction of hydroxylamine with nitrous acid has been the subject of kinetic - " and isotopic-tracer " ° studies. In addition to formation of nitrous oxide (2), there is a minor reaction (3) forming hyponitrous acid. 

I,2,3-Benzotriazin-4-ones are useful reagents in peptide synthesis and may be synthesized from the anthranilic acid by successive reaction with thionyl chloride (which forms an unstable sulphinamide anhydride), O-(trimethylsilyl)hydroxylamine and a nitrous acid-hydrochloric acid mixture at low temperature. 

Formation of Hydroxylamine Disulfonate by Reaction of Nitrous Acid with Bisulfite Ion. Hydroxylamine disulfonate (HADS) is formed according to the following net reaction ... 

Reaction of hydroxylamine with nitrous acid to yield hyponitrous acid or N2O. 

Good examples to start with are ammonia, the simplest amine, and its hydroxy derivative, hydroxylamine. Both react readily with nitrous acid in acidic aqueous solution, as shown in Schemes (3-1) and (3-2) ammonia yields molecular nitrogen. This method was used as a preparative process for N2 decades before fractionation of air became commercially available. The product of the corresponding reaction of hydroxylamine is dinitrogen oxide (originally called nitrous oxide). 

What is the reaction of hydroxylamine with nitrous acid ... 

In the reactions with hydroxylamine and its methyl derivative and with nitrous acid there is no evidence for complex formation, and six... 

Hydrazine is also used in conjunction with HNA to impede hydroxylamine oxidation by nitrous acid, always present in nitric acid media, which increases the HNA availability for the plutonium reduction. Both hydrazine and HNA interact with nitrous acid (HNO2), but the hydrazine oxidation is much faster. On the other hand, the use of HAN in conjunction with nitric acid introduces the possibility of an autocatalytic reaction resulting in the overpressurization of the system or explosion in a reprocessing facility as pointed out in Barney s report (Barney, 1998). The main function of HNA is to reduce plutonium from the tetravalent state to the trivalent state and, thus, separate the plutonium from the uranium, which is retained in the hexavalent oxidation state and, hence, in the organic phase. The reduction reaction by HNA is the result of two irreversible reactions (Equations 14.10 and 14.11) ... 

Sulfur dioxide or bisulfites are rarely used in combination with nitrites, because their reactions in acidic media yield sulfonates of either hydroxylamine or ammonia, which destroys the preservative activity of the individual additives. The reaction of alkali metal nitrites with bisulfite at lower temperatures leads to the formation of hydroxylamine N, JV-disulfonate, H0N(S03)2, which is hydrolysed to hydroxylamine JV-sulfonate, HONHSOj and further to hydroxylamine (H2NOH). At elevated temperatures complete substitution proceeds with the formation of ammonia JV-trisulfonate, N(S03)j , which is hydrolysed to sulfa-mate, H2NSOj . Subsequent reaction of sulfamate with nitrous acid leads to production of bisulfate ion and nitrogen gas ... 

Accordingly, diazobenzene and nitrous acid are related to each other in the same way as are phenylhydrazine and hydroxylamine the latter two substances, in fact, yield the same reaction products with carbonyl compounds as the former two do with the corresponding methylene derivatives. 

S-Nitrososulphinates can be made by treating sulphinic acids with N2O4 at about —20 °C in ether (equation 32)76. Use of nitrous acid on alkyl nitrites leads to the formation of the corresponding hydroxylamines (equation 33) in a reaction where it is believed that the first formed nitrososulphinate nitrosates another molecule of the reactant sulphinic acid77. 

Nitrous acid can substitute the more reactive aromatic derivatives by attack of NOeon the ring and form Ar—N=0 compounds. A product obtained from benzenol by this kind of reaction has the formula C6H502N. Exactly the same substance is formed from treatment of one mole of 1,4-benzenedione with one mole of azanol (hydroxylamine Section 16-4C). On the basis of the reactions by which it is formed, write two likely structures for this substance and explain how you would decide which one was correct on the basis of chemical and spectroscopic tests. 

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