Dear all,
I am working on a risk analysis of nitrosamines in some liquid products.
Would you consider that saccharin sodium could form nitrosamines?
Thanks in advance!
Laura Parra
Saccharin is a sulphonamide, not an amine. The nitrogen is not basic, because there are two strong EWG which delocalize the nitrogen pair. I never found reactions with nitrous acid or sodium nitrite.
A nitroso derivative of Saccharin has been reported after reaction with tert-butyl nitrite:
Artificial sugar saccharin and its derivatives: role as a catalyst
However, this compound has been supposed as intermediate; it was not isolated, nor characterized.
Also in another article, the same reaction has been reported and also in this case the intermediate (N-nitroso saccharin) was not isolated.
Arene diazonium saccharin intermediates: a greener and costeffective alternativ e alternative method for the pr e method for the preparation of ar ation of aryl iodide
I don’t think that this puculiar reaction should be considered as representative,
kind regards
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What I could add here is that yes, the nitrosation of saccharin do not arrives to a nitrosamine that is the purpose of the guideline. In a common finished product manufacturing process I do not see the possibility of the nitrosation of this sulfonamide.
Also, is that for forming saccharin you can use a diazotation reaction (nitrosation of a primary amine). Therefore, it would be worth asking the manufacturer a synthesis diagram and if they use the di-azo reaction unless there is a nitrite scavenger somewhere in the synthesis, quite a bit of nitrite content per mg of sweetener could be present.
- Considering that is very important that no cross-contamination with presence of secondary amines is there. As the nitrite salt used for the diazo coupling is normally in excess and will for sure nitrosate any low content of secondary amine. Supplier qualification is key.
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