NileRed - 2014-05-29
In this video I will be making Wintergreen, or methyl salicylate, using methanol and salicylic acid. The reaction carried out is known as a Fischer esterification reaction Nile talks about lab safety: https://youtu.be/ftACSEJ6DZA -------------------------------- Patreon: https://www.patreon.com/nilered Youtube Membership: https://www.youtube.com/c/nilered/join NileRed Merch Store (NileRed Pin & Keychain): https://store.dftba.com/collections/nilered NileRed Website (Glassware & Beaker Mugs): https://nile.red -------------------------------- Instagram: https://www.instagram.com/nile.red Twitter: https://twitter.com/NileRed2 Discord: https://discord.gg/3BT6UHf
Thank you for taking the time to upload all of these videos. I suffered a stroke 2 years ago, and it lead me to be on long term disability. Basically means I am medically retired. I worked 37 years in IT, going back to mainframes in the 70's. I am also in the USA martial arts Hall of Fame. Then one day I have a stroke, and BAM...not working and struggling to regain my mental and physical capabilities. So I found myself looking for a purpose, still into marital arts, doing more teaching these days. But I have decided to go back to things that interested me in my youth, the sciences. I am bought chemistry sets, lab glassware, chemicals, and of course books. I stumbled onto your videos accidently, but I am happy I did.I appreciate the quality, the substance, the topics and experiments you have chosen. I appreciate the detail of the dialog, and the description of the tools / tubes you use. I see so many for sale on ebay, but was many of them don't have their correct names. So thank you, I have subscribed to you, and look forward to more experiments on video. Sincerely, David Fiscus
I am sorry to hear about the stroke, but it sounds like you are not letting that hold you back :). I am very happy to hear that you are enjoying them and finding them useful!
Weird flex but ok
Interesting story. Chemistry has always been in your blood but you pursued other paths.
Hey friend, just curious, but how has it gone these past few years? Gotten better with chemistry? Given up and gone to something else really cool? I’m just curious since you last posted 4 years ago, and would be interested in how you are now! Have a wonderful day
Any update these years later?
I'm not even a chemist and your videos are fascinating. Thanks mate!
Thank you!
"As a rule, you should never eat anything made in a lab"
Up Next: Making mint flavoring from aspirin | Edible Chem
LOL
Because every rule has exceptions. I expect for edible chem he's ensured that everything used and the environment is safe to ingest
As you were saying not to drink it but to smell it at the end, I thought of "inhale this but do not touch".
YES! I can finally make my own chewing tobacco!
"You should not fill your distillation flask more than halfway. However, I was too lazy to change to a bigger flask." #gradstudentproblems :) haha
This is my first video from your channel and I'm already subbed! Keep up the good work :)
Well, you will be happy then. I am re-making this video, except I will be producing some "food-grade" stuff and attempting to make some minty candies.
Great videos dude! I remember making this back in high school chemistry!
so... the algorithm has gathered us all here, I see. about time
can you link the video in which you made salicylic acid? (btw I love your videos! it goes really well with my high school organic chemistry)
I love your voice and accent 😍
you do alot of purefying
I accidentally dropped a vial of this stuff while I was at high school on myself; I smelt like spearmint for the next few days. The lab basically got a permanent smell of peppermint. High School... =)
"the purple box" i never thought i would have heard that from you.
The aroma is refreshing
It's bean fatal? Lol.
Great video!
I repeated a few of your procedures and I love your videos/technique. Keep the chemistry coming! By the way, the product after distillation of this video can reach >99% by GC/MS, I didnt run an NMR because I wasn't sure of the expected spectra.
Very nice work!
Thanks!
I love your videos! I just subscribed (especially loving your "how to make bromine" video!)
@krisma12234 Thanks!
That foam at the end was basically shaving cream right? Or close to it? I'm probably wrong lol
Very professional. Thank you!
i wish i am as good at chem as you
I love your channel.
Hi the name wintergreen actually comes from a small shrub called Gaultheria procumbens, which is also known as teaberry. Some birch trees also have this smell, like yellow birch (Betula alleghaniensis). Several different plants have this aroma. Methyl salicylate is used also in Listerine.
awesome video yet allot of work to achieve your end product.
This stuff actually occurs naturally and makes outright huge crystals. These crystals have two oxidation states, one brown, rough, state covering the whole crystal, and one slightly greener, more fluffy one. This greener state is actually edible (chewable) and tastes rather nice.
Interesting, we did this in our chem class in college like 20 years ago when we were making esters. I forget how we goofed it up exactly, but we ended up tossing the aqueous part, and got horrible yields. Imagine that, we threw out the good stuff...
Great video, thank you for the memories of that wonderful week, where someone always ended up spilling butryic acid and making the entire wing smell like barf for a month... lol!
Is this why Trident White stopped selling Wintergreen flavored gum? The reason you gave at the end where it can be toxic?
zingadooda no because the amount of wintergreen flavouring used in food products isn't enough to harm you. Dosage is a very important part of determining if something will harm you. Keep in mind that drinking too much water at one time can kill you too
that Dihydrogen Monoxide is evil stuff. The devils liquor, i tells ya!
(+Erwin Rommel) Water overdose is absolute hell. The fact that I can say that from personal experience shows that it really isn’t something that never happens. The dose makes the poison.
Of course the most common use that we will recognize of Wintergreen flavoring is Pepto Bismol.
Or Copenhagen
how much temperature do you carry out this reaction?
I have a friend who really likes your videos and he showed me this channel because I really love chemistry. I'll be majoring in chemical engineering when I enter college and I was wondering on an off note, for the sake of people like my friend who has hearing issues, have you thought of making accurate captions to your videos? I'd be happy enough to do it because I really believe you are making something accessible to all and you should keep up the awesome work! Loved your video on cellulose extraction, it was super interesting!
What would you recommend to use instead of plastic clamps?
Great video! I just had one question about tipping the balance of the equilibrium reaction. Because Methyl Salicylate is broken back down by water, would it be possible to add molecular sieves to prevent this from occurring? And as a more general follow-up, are there any reactions that might react with the sieves, making them obsolete?
If one uses e.g. anhydrous CaCl2 in the reflux stage, as to absorb water molecules - do you think it would increase the yield?
Ok, now you made mentos. :)
What kind of heating mantle do you use? Where did you get it?
Wintergreen.... Good enough for the aches and pains of my forefathers and foremothers and and good enough for me now I'm on the downhill slope to the assuming of room temperature. One of those rare traditional medicines that A) Is dirt cheap and B) Actually works.
where can I buy methanol locally? also could I busy acetone instead:
Hey Nile, maybe a dumb question, but why always round bottom and heating mantle instead of Erlenmeyer and hot plate?
What do you put between the hotplate and the flask?
+Slava Chebotaryov It is called a heating mantle.
+Nile Red Is a heating mantle necessary when heating a round bottom flask?
@Ac Hendrickson no but i prefer it because it heats up fast and you get good control. You can also use an oil or water bath
sand or crushed broken glass are not so bad either. to speed up the process I heat with the propane 1st
Thank You 🍃🌿🍃📖🌿🍃🌹🍃
What programs do you use to draw structures? The images look a little inconsistent with the fonts... Aside from that, I love your videos! It's a nice change from the milligram-scale reactions I usually deal with in lab, haha.
haha, I just copy paste them from Google images. I normally would use Chemdraw, but for some reason I didn't have it installed and I got too lazy to download it and register. I will however do that today though. It will make things a lot easier.
For this I believe that the Alcohol can react with the phenol to it ether! My method is
C6H4OHCOOCl + CH3ONa = C6H4OHCOOCH3 - NaCl. Water Free! Just to Distill it to Separate it. It Yield Will Be A little More
One question, what is the concentration of your sulfuric acid? 96 or 30 %
Wud you make a video of isolating salicylic acid from weeping willow
Question: Im trying to start my backyard lab, but am starting from scratch. Does anyone have any suggestions for getting cheap gear/reagents? How did y'all get started?
My advice is tread carefully and check up on local laws. In some places simply owning a flask can land you in prison for possession of drug production equipment. intent be damned. Welcome to the land of the free!
go to a used item store. the other day i found beakers and shit for like a buck each.
Dont cheap out on saftey equipment ok? Medical expenses are a pain in the butt.
Do you need to use Sulfuric acid as a catalyst or can i use another acid (like hydrochloric acid)
you should be able to use dry hydrogen chloride gas dissolved in methanol. However if you used aqueous HCl, the water would destroy the product.
Do a reaction of diazomethane and sharp glass!
I remember learning about triboluminescence when I went to a winter camp in 6th grade. We snowshoed onto a frozen lake in the dead of night just to stargaze and snap wintergreen lifesavers.
keep up the good work man. I'm absolute shit in my chemistry class but your videos are much more entertaining than a 75 year old woman who speaks in monotone. not to mention she's not a chemist she's a geologist
April Pendley - 2019-06-24
‘Don’t eat anything you make in the lab.’
Later: ‘Edible chemistry!’ 🙂😂
TVTV VTVT - 2020-12-12
"Don't eat anything you make in the lab! Hey by the way, always be sure to wear your chefs coat while in the lab!"