NurdRage - 2011-03-07
In this video we make luminol from domestically available chemicals. The process pretty complicated and dangerous at parts and so should only performed by, or under the direct supervision of, an experienced chemist. First we obtain diethylhexyl phthalate by refluxing 50g of finely cut vinyl gloves in enough isopropanol to completely cover them for at least one hour, preferably three to four. The alcohol solution of diethylhexyl phthalate is filtered and the supernatant is boiled until it reduces to half its volume. An equal amount of water along with 10g of sodium hydroxide is added and the mixture boiled for an hour. This causes the diethylhexyl phthalate to hydrolyze into phthalic acid and 2-ethylhexanol. After the solution cools it will phase separate into an aqueous layer containing disodium phthalate and an organic layer containing the alcohols. Retaining just the aqueous layer, 25mL of 12 molar hydrochloric acid is added to precipitate the phthalic acid. Chilling may be necessary. The supernatant is discarded and the residue of wet phthalic acid is purified and converted into phthalic anhydride by heating it to 300 Celsius. First the water boils off and then the phthalic anhydride evaporates and condenses on the sides of the beaker. At this point a flask of cold water is placed over the beaker to allow the phthalic anhydride to deposit on it. Periodically the phthalic anhydride deposits are harvested until no more can be obtained. 45mL of sulfuric acid along with 13g phthalic anhydride and 19g of sodium nitrate are stirred together with the temperature slowly ramped up to 110 celsius. Once the temperature is reached the reaction is held for one hour to nitrate the phthalic anhydride to 3-nitrophthalic anhydride. Heating is then removed and the mixture allowed to cool back to room temperature. The gelled mixture is then transferred into 150mL of ice-cold water and vigorously stirred until all the chunks are broken up and nitrogen dioxide gas is no longer produced. Then the mixture is allowed to settle overnight. Then it is vacuum filtered and washed with two 50mL portions of water and allowed to dry under the forced air stream. 1g of the 3-nitrophthalic acid is combined with 616mg hydrazine sulfate and 1.4 sodium acetate trihydrate and 1mL of water. The mixture is boiled with a heat gun until dry. Then 4mL of polyethylene glycol (dot 3 brake fluid) with a boiling point higher than 230 celsius is added. The mixture is heated to 220 Celsius for ten minutes. The mixture is allowed to cool to below 80 Celsius and then transferred into a large beaker with 100mL of water. 10g sodium hydroxide and 13g sodium metabisulfite are dissolved into the mixture. 5g of torn aluminum foil is then jammed into the beaker and held down with a flask while another flask of cold water is placed on top. Vigorous hydrogen evolution and self-heating will occur as the aluminum foil reacts. The mixture is allowed to reflux until it stops on its own. Additional aluminum foil is added and the process repeated until the mixture has no further change in color. The mixture is filtered and the residue washed with an additional 50mL of water. The filtrate is then separated from any floating organic products. In a separate container a solution of 200mL of water and 25g of sodium bisulfate is prepared. 100mL of acetone is added and the filtrate is directly added to the mixture with vigorous stirring. Stirring is continued until there is no further change in the consistency or volume of the slurry. The supernatant is decanted off and allowed to evaporate. The cake of luminol is mixed with 100mL of water and thoroughly washed to remove any remaining salts. The mixture is vacuum filtered and allowed to dry. The Luminol can be tested by reacting an alkaline solution of it with bleach.
wow O_O that... was epic. no idea how you'll top that but great video.
I'd say you've done some things that at least equal this a decade later :)
Congratulations on an excellent demo. Both very entertaining and informative! Keep up the great work guys
I love this experiment! I would love to see this done with lab grade chemicals.
7 years ago, this video inspired me to be a chemist. In three days I will be graduated in Bachelor's degree of chemistry. Thank you very much NurdRage :)
this is an experiment in every microchem lab, but I love the fact that you show us how to do it with domestically available chemicals! Awesome :)
Wonderful to have you back where we need you the most!! I have missed these tutorials so much that you would not believe it. You have my full support :) And do I have to mention: Perfect video once again!
I am in college and my chemistry teacher was so impressed when I demonstrated the process to the whole class. She though I couldn't do it! I love your work and I hope I become like you in the future, a great chemist.
btw, the luminol here made is actually CHEAPER than buying it, 1g→20$
I make 100g of luminol for a total of 540$
and, even if it took some time, i love it and my quantum cola will finally be "BIO"
I’ve gotten it 10$ for 2g, or 5 for 1.
@ThisThat BullShat where did you buy it?
@vio tato likely ebay
That's awesome nurdrage. As a chemist I really find your videos entertaining and scientifically interesting. How did you come up with this synthetic strategy?
As always a genuinely epic video which is a huge commitment in terms of cost, time and your clear & serious love of chemistry. Thank you so much it is hugely appreciatted and a wonderful project for those interested in exploring organic chemistry but with household products! :D
This is an incredible video. What an accomplishment, NurdRage! It's awesome that you put so much time and effort into this, and it really made a fantastic video.The process was really well described and I liked seeing the illustrations of all the intermediate compounds. It made it really easy to follow. This is why I love chemistry!
hi NurdRage. Great video! I just have two questions: can methanol (or ethanol) be used instead of isopropanol (for the extraction step) and can potassium metabisulfite be used instead of sodium?
The first step describes exactly the work of hobbychemists! Great work! One question: Why you decided to perform the reduction of the nitro-group with metabisulfite, the hydrochloric acid/iron-methode (Bechamp reduction) could be possible as well, isn't it?
Hi! I really love your videos! I'm planning to be a chemist, and I would like to know where you have learned all these technics... or, where should I look for all this information? Congratulations! You are a really good Chemist! Sorry about any Englsih mistakes. Thanks!
Hello, great vids you make here! I wanted to ask, do you have any resources/guides on how to read those synthesis diagrams? I'd like to look abit into that in my spare time :)
6:50 It's wierd how diffferent the process of separating constitutional isomers can be for different compounds. In your pyramethamine series, the separation of 2-chlorotoluene and 3-cholorotoluene seemed like kind'o a nightmare, where you had to take advantage of steric hindrance to selectively sulfonate the 2-isomer. But in this video with the 3-nitrophthalic acid and 4-nitrophthalic acid, it's just "eeh, just mix it in some water, the 4-isomer will the dissolve, the 3-isomer won't".
I love the fact you end with "This is as basic as it gets it only gets harder from here " very motivating lol thanx for another great vid!!
Wow, I watched this video when it initially went up and now watching it again, I actually understand what's going on and why. That makes me really happy haha. Keep up the great work! Hope to see more from you soon.
I have a question. Is there a steadfast rule for nitration reactions in regards to the stoichiometry of the reactants? I noticed that your mole ratios of phthalic anhydride:nitrate salt:sulfuric acid was 1:2.5:10
I just love organic chemistry :) Anyways, basic hydrolysis of the ester does not produce phtalic acid, but instead it will yield directly into deprotonised phtalate. Since hydroxide ions act as the nucleophyle. In basic conditions, carbonyl-groups are not strongly electrophylic so a stronger base then H2O is needed to act as the nucleophyle. No neutralisation takes place.
Hello NurdRage! Great Job as always! I have a question: why did you dehydrate to phthalic anhydride? If the molecule is not dehidride the wouldn't the (H2O-NO2)+ attack at the same spot? Thanks!
You make it look so easy. I have chemistry practicals on Tuesdays and each time, no matter how thoroughly prepare, it ends up with me running around and panicking whilst my stuff is exploding/on fire. I enjoy chemistry a lot but i'm glad that i only have it for two more semesters :S.
Very nicely done! A completely OTC synthesis! I also did this at home (Jor from sciencemadness), but I did not do a complete OTC synthesis. I nitrated phthalic anhydride, reacted this with hydrazine hydrate in glycerin, and reduced this with dithionite in ammonia :)
Absolutely stunning work! Like a boss!
Wow, this is great for people who might want to go for a career in organic chemistry (like me!). Thank you for the awesome video!
Wow I learnt more watching this than I did taking organic in Uni. Although I was an engineering student and it wasn't necessarily my major.
For the testing I recommend dissolving Luminol in sodium-hydroxide and add some hydrogen-peroxide together with a catalyst like Caliumhexacyanoferrat(III) or Hemine. The bigger the Hemine contentration the more intense and the longer the reaction (to some degree). The bigger the hydrogen-peroxide concentration the more intense but shorter the reaction. Now I wonder if Caliumhexacyanoferrat(III) or Hemine really are catalysts, because the reaction is prolonged and more intense. Anyone knows?
Nice one Nurdrage, too complicated for me to have a go at, but now that I have seen you do it, I don't have to!! Keep up the good work.
great video!! is there an easier and less complicated way to extract luminol for instance the glow stick that you showed on your video? because as much as i would love to, i am not a chemistry genius like you
Your videos are awesome! Keep them coming!
Neat stuff. Sure, I'll probably never actually need to make luminol from scratch, but hey, still neat to watch and learn.
What software do you use for the diagrams and the showing of reactions (in blue)?? Great video by the way . . . . . if I had as much equipment as you I'd never be bored!!
@NADHHH Yield and recovery are quite variable and some gloves do better than others. As mentioned in the video if you need more you'll need to repeat the process until you get enough for the nitration step. Variability was anticipated and built into the procedure.
Very nice protocol. I'm pretty sure column chromatography at several points along the way would improve yield and simplify purification. While it is the bane of my existence, column chromatography is the most important tool in multistep synthesis.
This is pretty much your youtube magnum opus! You've been an inspiration nurdrage, you and all others like you!
This would be awesome to do. I hope someday I will be good enough at chemistry to do this.
Chemistry question: Im sorta learning about chemistry, I'd like to know some things Why not stick an amine on phthalic anhydride using ammonia/ammonium? Does it affect the yield or affect the product? Thanks ~Iso.
this looks like it took a very long time and lots of effort, good job!
Deviating from the whole home-chemistry set, would reducing the nitro group to an amine be possible using sodium borohydride insead of the metabisulfate-catalyzed hydrogenation?
Can you explain the reactions occurring at the end when you are converting the Nitro group into an Amine group on the 3-Nitrophthalhydrazine?
If I had all of the equipment you have I would never be bored!
Wow, awesome! I've made it once starting from phtalic anhydride. Starting from rubber gloves is much cooler! I have to do a Strecker synthesis in a few weeks, you should demonstrate that some time :P
Great video! Can 91% drugstore isopropanol be used? Or, could isopropanol gas-line antifreeze (Iso-Heet) be used?
I think I missed my lifes calling. :-)
I know nothing of chemistry but I can watch you do these for days. amazing interested
right? this shit is so cool. if i could go back and start over i would have totally became a chemist!
@NurdRage Thank you for all the time you put into these video! They are amazing!
Hello NurdRage! As a senior chemistry student who loves org.chem I have 2 questions: Do you know where I can find the mechanisms for the hydrazine condensation and the Al/ NaOH reduction steps? Also in the step of nitrating the benzene ring, isn't possible for the sulfuric acid to hydrolyze the anhydride instead of reacting with sodium nitrate? Kudos for your videos!
Nice one because although I'm fairly intelligent, I've never been as natural at a science as you guys!
@0adireita Thanks! I hoped to show in this video that with enough brute-force knowledge and understanding even domestically available chemicals can be made into something awesome :)
@NurdRage Is there any chance you could release videos on a more frequent basis? This higher-level chemistry interests me, but the delay between your videos is far too long to keep my interesting going for long periods.
Spy Dolphin - 2019-07-31
After years I realize how this video impacted my life so dramatically. As a freshman in highschool i knew just some basic chemistry and this video completely blew my little brain off. Seeing the whole process and the final results was something i had never seen before nor imagined whatsoever. The synthesis screen at 14:10 is something i remember since that day, thinking - one day i'll understand all of this. And so here I am today in my last college year, completely in love with organic chemistry since that day, starting to get into the research world as deeply as i can and with the firm will to make this subject my life. In this sad day when we loss The King Of Random I felt the urge to communicate how grateful I am to you for this video and for your entire work on youtube, hoping one day you can read this.
Thank you from the bottom of my heart NurdRage, you are loved.
Master of the Universe - 2020-09-29
Why sad? That guy was a pr!ck and a con.
Jeremy McAdams - 2021-08-08
@Master of the Universe What exactly happened both death and con? I didn't even know he died but I haven't really watched any of his stuff in years.