Volitox Ignis
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Saccharide (?) Synthesis
I was reading about the salt known as Denatonium Benzoate, one of the most bitter substances known to man and also used as a bittering agent. However,
there is another, more bitter salt, known as Denatonium Saccharide. It is a salt of Denatonium and an ion closely resembling Saccharin in structure,
although not quite identical. The SMILES code for the ion would be C1=CC=C2C(=C1)C(=N[S]2(=O)=O)[O-]
The full image of the molecule can be found here https://pubchem.ncbi.nlm.nih.gov/compound/Denatonium_sacchar...
The "Saccharide" ion differs from that of Saccharin in that the oxygen is bonded to the carbon atom with a single bond in "Saccharide" as opposed to a
double bond in Saccharin, and that the nitrogen is double-bonded to the carbon atom. It is this "Saccharide" that is needed for the synthesis of
Denatonium Saccharide.
I wish to make Denatonium Saccharide. There is a video on Youtube on how to make Denatonium Benzoate by first making Denatonium Hydroxide and then
reacting that with Benzoic acid. I figure that the same procedure could be done for DS, but using the free acid of "Saccharide" instead of Benzoic
acid.
How can this "Saccharide" and the free acid thereof be prepared?
[Edited on 20-4-2019 by Volitox Ignis]
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UC235
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It's just the salt of saccharin. They just show the anion as an enolate-type resonance structure there, though I'm not sure which is actually
preferred.
Saccharin free acid can be readily prepared by dissolving bulk store brand saccharin sweetener in a minimum of water and adding HCl. The free acid has
poor solubility and crystallizes out.
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Volitox Ignis
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Could I expect any impurities from doing the extraction with HCl?
Also, around what percentage by mass could I expect store-brand Saccharin sweetener to actually consist of Saccharide salt, as opposed to filler?
[Edited on 23-4-2019 by Volitox Ignis]
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UC235
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As long as your HCl is clean, it shouldn't contaminate the product in any way. I diluted 31.45% pool grade stuff down to 20% with distilled water and
then distilled it. This gives you azeotropic 20.2% HCl free of metal contamination.
You can buy and tear open hundreds of little packets or opt for the bulk sweet n' low. The stuff is essentially sodium saccharinate sprayed onto
glucose with a little anticake. It's about 3% sodium saccharinate.
Basically, weigh out your powder. Dextrose monohydrate has a solubility of 54g/100g H2O at 0C. You want to exceed this so sugar doesn't also
crystallize out, but you're losing saccharin as you add any extra water. Work out how many grams of dextrose are in your powder. If you use 100g, you
have 97g dextrose. We want the final volume of water to be 97/(54/100) = 180ml. You're going to add 5ml of 20% HCl per gram of sodium saccharinate (4x
excess). So dissolve your powder in 165ml of water, filter if you see anticake clouding the solution, and add 15ml of HCl. Chill in the fridge or on
ice for a while. Filter. Wash with ice water. It can be readily dried in air.
I used walmart brand packets. A box of 250 got me 321g of powder and about 6g of saccharin free acid.
[Edited on 23-4-2019 by UC235]
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