Synthesis and Chemiluminescence of Luminol

3-Nitrophthalhydrazide, prepared in a previous video, is reduced with a readily available reducing agent (thiourea dioxide, TUD) to luminol, which is obtained in 66% yield due to some minor complications with workup. A significantly higher yield would normally be expected based on a smaller batch run previously. The product is then used for two demonstrations of chemiluminescence: Potassium ferricyanide catalyzed light emission in water utilizing hydrogen peroxide and uncatalyzed light emission with NaOH in dimethyl sulfoxide using atmospheric oxygen. Note that the reaction mechanism is not given for the reduction. This is because I am led to believe that TUD functions by a single electron transfer mechanism, which is fairly confusing to draw out. The intro music clip is from "Stealing Fat" by The Dust Brothers. I believe this falls under fair use.

Category:

Science & Technology

Tags:

• make
• 3-aminophthalhydrazide
• aminophthalhydrazide
• 3-aminophthalylhydrazide
• dimethyl
• sulfoxide
• DMSO
• aminophthalylhydrazide
• synthesis
• preparation
• nitrophthalhydrazide
• 3-nitrophthalhydrazide
• organic
• chemistry
• hydrazide
• nitro
• 3-nitrophthalylhydrazide
• luminol
• chem
• chemiluminescence
• chemoluminescence
• chemoluminescent
• demonstration

[Phacias]

Bravo sir! I am addicted to Your channel :) Does Luminol emit light under UV?

[UC235]

@Phacias Luminol solutions will indeed fluoresce when exposed to UV light, but it's completely unrelated to the chemiluminescent reactions. In fluorescence, the high energy UV light excites the molecule, which relaxes and emits lower energy light, in this case in the visible range. The difference in energy ends up as heat. The luminol is unchanged. In the chemiluminescent reactions I have shown, the luminol is destroyed and the immediate reaction product is in an excited state.

[Phacias]

@UC235 I know how luminescence works sir. Just asking about a property of that compound :)

Thanks for Your precise answer.

[UC235]

@Phacias Just sayin' Other viewers might be interested in that info.

[aaronjhard]

Great work,!! What's up next ?????

[UC235]

@aaronjhard Something easy. Then I will go back to a longer project.

[staszek300]

Can you write the response patterns of sum scores and give the by one compounds name?

[Bilbo940]

A far better catalyst is actually Cobalt ions (in complex). I wrote an experimental essay on this reaction last fall so unfortunately I couldn't take help of your great video :) subscribed

[NurdRage]

nice work, much better than my approach with the aluminum and sodium metabisulfite.

[fmeriqui]

awesome

[ChemCrazy81]

Awesome! Do you think that hydrochloric acid could be used in place of acetic acid, with pH tested every mL or so added after the theoretical amount needed to neutralize the ammonia? (I'm cheap, and stingy with stuff I can't buy OTC)