[Nvaus]

Hi all, I've been looking into the sulfonation reaction presented in this paper: https://doi.org/10.1016/j.carbpol.2010.10.038

The reaction uses sodium nitrite and bisulfite in solution to form the sulfonating compound N(SO3Na)3. This is done under highly acidic conditions contributed by the bisulfite, and then the solution is brought to about 11 pH prior to adding the polysaccharide for sulfonation.

Would you consider this reaction risky for the formation of nitrosamines?

This book mentions that sulfites are among the best nitrous acid scavengers in the prevention of nitrosamines, which is reassuring since the sodium bisulfite is used in excess: https://www.sciencedirect.com/topics/chemistry/nitrous-acid

However, in saying so the book also mentions that sulfites and nitrites produce hydroxylamine disulfonate, which seems like it could be further reduced to amines in solution... Another source confirms this, that hydroxylamine disulfonate may react further to form amine trisulfonic acid or amine disulfonate (https://www.osti.gov/biblio/6693469?utm_source=chatgpt.com pg.6)



That source seems pretty thorough in exploring the reaction possibilities between NOx and sulfites but makes no mention of nitrosamines. However, it also seems like health hazards were not their concern.

Any thoughts on this? Thank you

Edit: I just realized this should have probably been posted one level up in the general organic chemistry forum. Mods please move if appropriate. Thanks

[marquis]

One place for further investigation is in polymers, specifically, polyisoprene.  This polymer is often used in the production of baby bottle nipples.  And not does mines have been an issue with these products for many years.

The way the nitrosamines were detected was with a TEA (thermo energy analyzer detector) for a GC.  This has probably changed to some form of gc/ms.  While NOx was easily detected by these instruments, using different wavelengths would also allow the detection of phosphorous bonds and sulfur bonds.  The initial detectors were quite large, about the size of a phone booth.  The one we had was about 3feet by 2 feet by 2 feet.  And subject to many interferences.  The same technology could also detect nitrates, with appropriate modification.  The section limit for nitrosamines was in the ppb range.  The test methods were a pain, but you can look those up. The column used was a,wax column which also led to some problems.

If nothing else, this might give a lead on nitrosamine formation in sulfur environments.  Polymers usually have both sulfur and nitrogen accelerators present.

[Nvaus]

One place for further investigation is in polymers, specifically, polyisoprene.

That's a great lead, thanks!