Nitrite degradation

The initial observation that menthone reacts with amyl nitrite in the presence of base to give a good yield of an open-chain oximino ester was not expanded for synthetic purposes until Woodward almost forty years later utilized this reaction for the cleavage of a 7-keto-decahydroisoquinoline in the course of his total synthesis of quinine. 

In the one application reported for the conversion of the 17jff-acetyl side-chain to the 17-ketone, the intermediate oxime was not isolated, but hydrolyzed in situ with acid in an overall yield of about 20 %. In the case of 17jff-acetyl-D-norandrostanes, which are particularly difficult to degrade to D-norandrostanes, the nitrite procedure proved the most convenient method. The yield is 25 %, nowhere near the much higher yield obtained by a Baeyer-Villiger reaction which, however, must be allowed to proceed for one month at 0°.  

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UK certoparin sodium anticoagulant Alpha parin Troparin Product from isoamyl nitrite degradation of porcine heparin. Relative molecular masses range from 5—7 kDa DVT anticoagulant... 

Kocuria varians Reduction of nitrite Degradation of reactive oxygen compounds Degradation of peptides and amino acids formation... 

When organics containing reduced nitrogen are degraded, they usually produce ammonium, which is in equilibrium with ammonia. As the pK for NH3 NH4" is 9.3, the ammonium ion is the primary form present in virtually all biological treatment systems, as they operate at pH < 8.5 and usually in the pH range of 6.5-7.5. In aerobic reactions, ammonium is oxidized by nitrifying bacteria (nitrosomonas) to nitrite... 

A unique method for the degradation of 17-hydroxy-20-oxygenated pregnanes to 17-ketoandrostanes involves the photolysis of the corresponding nitrite esters.While this generally is equivalent to bismuthate or periodate oxidations, it is the only mild method for the conversion of a 17-hydroxy-... 

It is not usual for unopened drums of nitrite-based chemical to degrade, and the product should remain in good condition for several years. However, it is possible for tannin-based corrosion inhibitors to degrade, even in unopened drums. Under warm conditions (such as storage in a boil-erhouse) and in the absence of a small amount of suitable microbiocide in the formulation, plastic drums containing tannin products may swell considerably because of microbiological degradation and gas formation. Care is needed to avoid accidents. 

Hofmann KW, H-J Knackmuss, G Heiss (2004) Nitrite elimination and hydrolytic ring cleavage in 2,4,6-trinitrophenol (picric acid) degradation. Appl Environ Microbiol 70 2854-2860. 

The degradation of 3-nitrobenzoate by Pseudomonas sp. strain JS51 and Comamonas sp. strain JS46 is initiated by dioxygenation to 3,4-dihydroxybenzoate with loss of nitrite (Nadeau and Spain 1995) (Figure 9.53b). 

Simultaneous degradation of 2,4- and 2,6-DNT has been achieved in a fluidized-bed biofilm reactor (Lendemann et al. 1998) that was successfully operated with contaminated groundwater containing 2- and 4-nitrotoluenes and 2,4- and 2,6-DNTs. The nitrite that was produced during degradation was recovered as nitrate. 

Sodium nitrite with sulphuric acid (this carries a danger of fibre degradation)... 

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