Paracetamol is converted to p-aminophenol in a process called base hydrolysis using sodium hydroxide. That's what is used in Parodinal.I can't help you much with the specifics but acetominophen (paracetamol) is not the same as para-aminophenol (real Rodinal) and may react differently to different alkalis
I can relate to the carbonate 'reducing' the alkalinity in view of the sodium hydroxide. - David LygaIn Parodinal, the sodium hydroxide also manages the conversion of n-acetyl-p-aminophenol (paracetamol, acetaminophen) into p-aminophenol (our intended developing agent). Sodium carbonate won't do that job; as I understand it (as a non-chemist) it takes a high enough pH to cleave the acetyl group off the original molecule. Further, sodium carbonate will reduce the activity (by buffering down the pH) and may allow recombination of the acetyl with the p-aminophenol (not sure about that last).
If one wants it badly enough, it ought to be possible (no, I don't know how) to separate out the p-aminophenol from the Parodinal, or produce it with fewer hangers-on, and convert it to n-methyl-p-aminophenol sulfate, aka metol.
....isn't sodium hydroxide simply sodium carbonate "on steroids"....
OK, this is exceptionally well defined and I thank you, except for the fact that you should be aware that sodium hydroxide RAISES the pH, not lowers it. -David Lygain a very limited sense, I guess that's true but...
They're like totally different molecules, man (think Jeff Bridge's character, The Dude in The Big Lebowski )
I mean, for example, Sodium carbonate has a carbon atom where as Sodium hydroxide has no Carbons...and Sodium hydroxide has a Hydrogen atom!
Just think of the difference between water (H2O) and hydrogen peroxide (H2O2)...chemically the only difference is one oxygen atom...but you'd be in a world of hurt if you drank a liter of hydrogen peroxide.
In a nutshell, and as others have said, the Sodium Hydroxide is doing more than just lowering the PH of the solution. It is actually necessary to convert the available-over-the-counter, slow acting, self administered human poison to a chemical that can be used to develop film (by reducing silver?) .
OK, this is exceptionally well defined and I thank you, except for the fact that you should be aware that sodium hydroxide RAISES the pH, not lowers it. -David Lyga
Hopefully someone can expand on what the phrase "attack the base" actually means in this case, as I'm also curious about learning more details on the chemistry we're using.
Is this referring to 'attacking the core of the chemistry we need for photo-development reactions', or does sodium carbonate react with other more alkali entries on the ingredients list to do unhelpful things?
Another point that might be helpful, being able to explain why Na2CO3 [Sodium carbonate] is the less 'aggressive' compound than NaOH [Sodium hydroxide] given that NaOH has less sodium for reactions to play with.
But there is some left unionized. (The power of collective bargaining agreements!)
Adding acid to PaRodinal (Don't try this at home) does produce a precipitate, very likely p-aminophenol.In Parodinal, the sodium hydroxide also manages the conversion of n-acetyl-p-aminophenol (paracetamol, acetaminophen) into p-aminophenol (our intended developing agent).
If one wants it badly enough, it ought to be possible (no, I don't know how) to separate out the p-aminophenol from the Parodinal, or produce it with fewer hangers-on, and convert it to n-methyl-p-aminophenol sulfate, aka metol.
You are beginning to clarify this. However, it has been my observation that adding sodium bicarbonate to a MQ developer with sodium carbonate always slows down the development. Perhaps this is because the baking soda is a weaker form of alkaline than is the sodium carbonate??? Somewhat like sodium carbonate is a weaker form of alkaline than is sodium hydroxide? - David LygaOkay, I am not PE, nor a chemist, but will attempt to explain.
Acids and bases are strong or weak depending on how completely they ionize in water, producing a lot of free H+ or OH- ions (for acid and base respectively). Sodium hydroxide, NaOH, is a strong base because it ionizes completely. Thus NaOH solution alone has a high pH. It's the amount of OH- produced by reactions of the ions with water that makes the alkaline solution, not the amount of sodium.
A weaker acid or base can be used to "buffer" the pH of a solution. This is because it doesn't ionize completely and make hydroxides by reacting with the water, so effectively it has some reserve capacity. If you put a weak base like sodium bicarbonate (NaHCO3) in water, some of the bicarbonate ionizes to make HCO3- ions. But there is some left unionized. (The power of collective bargaining agreements!)
That means that if you put either a little bit of acid or of base into the bicarbonate solution, some of the bicarbonate will react with the newly introduced H+ or OH-, and it will go back to the equilibrium of a weak base. That's buffering. For more technical information, https://en.wikipedia.org/wiki/Buffer_solution and https://en.wikipedia.org/wiki/Buffering_agent
The net effect of this is that if you add a weak base to a strong base, you don't get an even stronger alkalinity. You are likely to get a weak alkaline, unless you overwhelm the buffer by dumping in a lot of strong base, in which case the weak base is irrelevant. Sodium carbonate is stronger than bicarbonate but much weaker than sodium hydroxide (also why sodium carbonate is less caustic and safer to handle). So it does not add to the alkalinity of the NaOH solution and will likely weaken it.
You are beginning to clarify this. However, it has been my observation that adding sodium bicarbonate to a MQ developer with sodium carbonate always slows down the development. Perhaps this is because the baking soda is a weaker form of alkaline than is the sodium carbonate??? Somewhat like sodium carbonate is a weaker form of alkaline than is sodium hydroxide? - David Lyga
You are beginning to clarify this. However, it has been my observation that adding sodium bicarbonate to a MQ developer with sodium carbonate always slows down the development. Perhaps this is because the baking soda is a weaker form of alkaline than is the sodium carbonate??? Somewhat like sodium carbonate is a weaker form of alkaline than is sodium hydroxide? - David Lyga
The standard literature for Rodinal states that no sodium carbonate can be added to Rodinal because doing so will "attack the base"
I remember some discussion how original formula was meant to have no hydroxide excess, only remaining p-aminophenol and sulphite, and hydroxide excess is modern formulas etc.
will "attack the base"
I am a chemist, so maybe I can say a few words that might help.
[snip]
Anyway, shifting gears a bit, if you add an acid to a solution of sodium hydroxide and para aminophenol, you will eventually drop the pH of the solution enough so that the para aminophenol (which is a negative ion in highly basic solution) becomes a neutral molecule. The neutral molecule is less soluble than the ionic form, and you may get precipitation of the para aminophenol. Adding more acid will eventually convert para aminophenol to positive ions, and then it will dissolve again.
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