The Organic Chemistry of <i>N</i>-Nitrosamines: A Brief Review

Anselme, J.‐P.

doi:10.1021/bk-1979-0101.ch001

Cited by 14 publications

(21 citation statements)

References 7 publications

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“…The equations of the metal-nirosyl complexes formed in water samples have been reported by Anselme [36], Rose and Jurs [37] Kumar et al [25] and Wang and Mitch, [26].…”

Section: π-Bond Formationmentioning

confidence: 96%

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Application of chromatographic techniques in the analysis of total nitrosamines in water

Yahaya

Babatunde

Olaniyan

et al. 2020

Heliyon

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The use of ozone, chloramine and chlorine dioxide for water treatment results in the formation N-nitrosamines in the treated water. These groups of chemicals and other nitrogen-containing compounds have been described as disinfection by-products (DBPs) which are known for their toxicity. Nitrosamines are a potential source of nitric oxide (NO) which can bind with metals present in the sample matrix leading to formation of metalnitrosyl complexes and dissolved metals have the potential to increase the total nitrosamines in water. This phenomenon has not received the desired attention and determination of metal-nitrosyl complexes lack standard analytical technique. Chromatography linked to various detectors is the commonest of the techniques for nitrosamine analysis but it is beset with reduced sensitivity as a result of inappropriate choice of the column. Incidentally, chromatographic techniques have not been really adapted for the analysis of metal-nitrosyl complexes. Therefore, there is need for the survey of existing techniques vis-a-vis metal-nitrosamine analysis and to suggest possible areas for method optimization.

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“…The equations of the metal-nirosyl complexes formed in water samples have been reported by Anselme [36], Rose and Jurs [37] Kumar et al [25] and Wang and Mitch, [26].…”

Section: π-Bond Formationmentioning

confidence: 96%

“…For instance, addition of NO ligand to metals lead to complexes reaction of NDMA with phenylcopper gives NDMA complex (Figure 15) [36,37].…”

Section: π-Bond Formationmentioning

confidence: 99%

Application of chromatographic techniques in the analysis of total nitrosamines in water

Yahaya

Babatunde

Olaniyan

et al. 2020

Heliyon

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“…Synthesis can be accomplished in both acid and basic media and in organic solvents . However, the nitrosation of secondary amines with sodium nitrite in the presence of acids is the most widely used method for the preparation of n -nitrosamines …”

Section: Ash-less Octane Enhancer Additives (<2 Vol %)mentioning

confidence: 99%

“…246 However, the nitrosation of secondary amines with sodium nitrite in the presence of acids is the most widely used method for the preparation of n-nitrosamines. 247 More recently, alternative synthesis methods have been reported, such as the iodide-catalyzed process to obtain nnitrosamines from amines and nitromethane using tertbutylhydroperoxide (TBHP) as the oxidant, which is operated under mild conditions and has operational simplicity. Commercially available and inexpensive catalysts and oxidants are used in this method.…”

Section: An-vv-f-748amentioning

confidence: 99%

New Octane Booster Molecules for Modern Gasoline Composition

et al. 2021

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In the framework of reducing GHG emissions and accelerating the decarbonization of the road transport sector, vehicle efficiency is a key factor for competitiveness. In this sense, the refining industry can make its contribution by reformulating high-octane petrol fuel. The impact of this type of gasoline from CO2 emission balance, technical feasibility, and economics standpoints has recently been assessed by the petroleum industry with promising results, and new potential boosters that could improve the octane number of standard gasoline are more needed than ever. The present work summarizes a comprehensive review aimed at collecting available data regarding chemical molecules that can be used in advanced gasoline formulations for modern spark-ignited car engines focusing on ash-free technologies. Potential boosters are divided into two categories: high-octane gasoline components and octane enhancer additives, with 2 vol % the considered frontier concentration between them. Targeted chemical compounds examined in the screening for high-octane components include isoparaffins, olefins, aromatics, alcohols, ethers, esters, ketones, furans, and carbonates. Chemical families assessed as additives were anilines, hydrazines, amines, pyridines, quinolines, indoles, N-nitrosamines, iodine compounds, selenium compounds, phenols, formates, oxalates, and, in lesser extension, other families. The scope of the analysis includes not only anti-knock effectiveness but also associated side effects for the engine, possible effects on both human health and the environment, current applications, and compatibility with existing infrastructure, among others. Promising opportunities in the medium- and long-terms for every family of chemical compounds that can potentially improve the anti-knock character of modern gasolines well beyond current specifications worldwide are presented. Furthermore, a few chemical families are identified as the most promising ones to be used in future gasoline formulations, either as high-octane components (such as ethers, ketones, and esters) or as octane booster additives (such as anilines, N-nitrosamines, and phenols).

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“…In order for a nitrosamine to form, a suitably reactive secondary or tertiary amine must be present together with a nitrosation source, and although 1 does contain a tertiary amine, it does not contain an obvious nitrosation source given that the nitro group is in a higher oxidation state; therefore, the formation of NDMA from ranitidine was not reasonably predicted via a favorable mechanistic reaction pathway. We have undertaken an in-depth scientific evaluation to determine the root cause for the presence of NDMA in ranitidine and associated drug products using contemporaneous, highly sensitive, and specific analytical methodologies with the results described below.…”

Section: Introductionmentioning

confidence: 99%

Ranitidine—Investigations into the Root Cause for the Presence of N-Nitroso-N,N-dimethylamine in Ranitidine Hydrochloride Drug Substances and Associated Drug Products

King

Searle

Urquhart

2020

Org. Process Res. Dev.

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The presence of low levels of N-nitroso-N,N-dimethylamine (NDMA) in ranitidine hydrochloride drug products has been reported by regulatory agencies. GlaxoSmithKline undertook a root cause analysis to investigate this observation using contemporaneous, highly sensitive analytical methodologies. The root cause analysis suggested that the presence of NDMA results from a slow degradation of the ranitidine molecule. Analysis using suitably isotopically labeled ranitidine hydrochloride confirmed the formation of NDMA solely from an intermolecular reaction of ranitidine hydrochloride without involvement of impurities. Factors that influence the rate of degradation include heat, humidity, and the crystal morphology of ranitidine hydrochloride with the material exhibiting a columnar habit showing a slower rate of degradation.

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The Organic Chemistry of N-Nitrosamines: A Brief Review

Cited by 14 publications

References 7 publications

Application of chromatographic techniques in the analysis of total nitrosamines in water

Application of chromatographic techniques in the analysis of total nitrosamines in water

New Octane Booster Molecules for Modern Gasoline Composition

Ranitidine—Investigations into the Root Cause for the Presence of N-Nitroso-N,N-dimethylamine in Ranitidine Hydrochloride Drug Substances and Associated Drug Products

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