Technique Series: Recrystallization (urea as an example)

This is a technique video that I have been asked to do for a while. I wanted to go over the basics. I might explore it a bit more in the future.
I hope you guys like it. The introduction video is mostly from my video of converting sodium benzoate to benzoic acid. That is filmed in 4K and will be uploaded later.
I plan to do an Q and A video, so if you have any questions you'd like me to address in the video, leave them in the comments.
Music by Kevin Macleod - Music for Manatees
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Nile talks about lab safety: • Chemistry is dangerous.

[@oscill8ocelot]

I'd be okay with a thousand-minute chemistry video...

[@NileRed]

+dzScritches okay, coming right up!

[@oscill8ocelot]

Nile Red

[@Atomos95]

+Nile Red The video is very interesting and useful but... too long. In you tube never go up 12 mins.

[@oscill8ocelot]

RealChemistry No way. The longer the better, I say. =)

[@Atomos95]

+dzScritches For me too. But it can be lazy

[@LENA.HA10]

watched his videos for entertainment 3 years ago. now watching him to learn the procedures for my orgo lab. love it here

[@harpsarp66]

same!!!!!!!

[@BrentKruegerZapperz]

Great demonstration, actually all your videos are well done, seeing all the correct glassware function so efficiently makes a little investment much easier to justify. 👍

[@lightvsdark21]

Really good info. Very well planned out! Thanks!

[@bigge1002]

Dude, not only do you make Hella entertaining videos but you also make great educational videos especially for us trying to do homebrews.

[@caseypfost5361]

i love watching these videos even if ive never taken a chemistry class

[@origamigek]

Those urea crystals look incredibly tasty~

[@Antonio-wh8lh]

In reality, you would probably find the experience rather unpleasant Since you are basically forming urea solution in your mouth when the crystals dissolve in saliva It would probably taste like piss Not that I know what piss tastes like

[@BalticLab]

Everything is edible chemistry if you're brave enough...

[@hypnotist1200]

​@@Antonio-wh8lhyes you do

[@WhyPhi]

Hi, I really enjoy your videos. Very good explanation/ overviews of your experiments, and I like how you show the mechanisms. Would it be possible to make albuterol? lol I'm just curious about how it's made because I have asthma.

[@nashtrall]

Came hoping to see liquid-liquid diffusion, still was not disappointed! Great job :)

[@Bananakid11]

chromatography would be really nice

[@hcn6708]

I hope he does Uranium Enrichment.

[@aeriumsoft]

Colorimetry??

[@finchisneat]

And expensive.

[@karlbergen6826]

I agree. Separating a mixture of lanthanide salts is something I've always wanted to try. As many if them are colored this will help check the progress. You can buy a mixed lanthanide oxide as a commercial product. Another thing you could discuss is fractional crystalization. Though not used much today. Its a forerunner to chromatography.

[@karlbergen6826]

@@hcn6708 Uranium enrichment involves isotope separation and makes fissionable material Bad idea.

[@comradegarrett1202]

are you ever going to do more of this series because watching your videos makes me feel not totally lost in organic chem

[@fanlixia5d113]

Yes

[@markolazarevic4209]

Awesome!!! Thanks a lot.

[@mangofrappucino]

I looooove watching your videos!! :)

[@D3lor34n]

Hey Nile, i've been watching through your backlog of videos in a somewhat random fassion and just stumbled upon your technique series. I love your content and it's as calming as it's interesting and very well presented. It makes me marvel at our universe while watching you perform "magic tricks" as you combine and extract stuff in various ways. I even started reading up on some things as i got really interested in chemistry, little did i know you made this series all those years ago. Since it doesn't seem to be a dedicated playlist either, would you consider a short series about the very basics and goals of chemistry in general? I think you old videos hold up pretty well, but there also is much improvement over the years for sure. So an updated series would also fit. I take it you are not that kind of educational channel, explaining everything for complete laymen, but if you threw an old fart like myself a bone to spread knowledge about chemisty i would really dig it. I was so very concerned when you tasted things which went through multiple steps getting dissolved in nasty stuff and to my uneducated eyes barely "cleaned", but as i start to make more sense of these processes it's fascinating to unterstand more about whats happening and why it's pretty much guaranteed to be pure at that point. If you read this, thank you for your inspiring work on this channel. You deserve every praise you receive and more.

[@JohnyPaprikas]

Incredible channel. Keep up the good work man!

[@agent475816]

In my organic chem. lab, we practiced recrystallization by recrystallizing benzoic acid contaminated with charcoal using water. When left to crystallize, the stir rod was left in the solution for a surface for the crystals to form. That's maybe better than damaging the beaker. Well not really damaging it, just a little scraping.

[@samodom3396]

Do u know how to make flakka

[@Blu702]

Do a video on column chromatography! You're the man BTW, thanks for all your videos!

[@nugboy420]

I like the manipulation of solubility dude that’s a good way to put it! And yeah a chromatography overview would be awesome cuz that sounds interesting!

[@fireandcopper]

seriously, I loved this. do you have the capacity to shoot in 60FPS?

[@NileRed]

+fireandcopper Actually yes. My GH4 can shoot 1080p 96fps, but i am mostly doing 4K/24fps

[@NeonKue]

Thanks, needed this to recrystallize a lido caine 😎👌

[@vladimirrienas5546]

I recently started working at a cannabis extraction lab doing hydrocarbon extractions these videos are great to help me under stand certain chemical processes going on at work and lab stuff in general this is a lot of good info that will carry over to crashing diamonds

[@chrismoniaci]

How do you get into something like that?

[@danielaustin7643]

my favourite technique is to heat up the solvent on a hot plate and add it slowly to my product when it is about 50% dissolved. (and it dependswhat solvent you are using) with solvent i put it on the hotplate as well to prevent it from cooling too early, when the solid has dissolved i take it of and let it cool really slowly, when it is at room temp i put it on ice to get the last crystals to form. it works really well but you must be careful that your product doesn't burn or melt.

[@nicks6980]

I'm amazed by that spinning thingy

[@somefool6409]

I'd be even more amazed by someone who could stir a reaction that could take days

[@danielaustin7643]

i think one of the biggest problems is having impurities that does not dissolve in the solvent and no knowing that they are not product which means you can add far too much solvent to try to get them dissolved, this can badly effect yield or may mean you have to add a second solent to get the crystals to crash out of solution.

[@rafael53461]

Nice music touch and great video quality! I wish I could help you with Patreon, you deserve it!

[@bobthornton8282]

some good stuff to study for organic on the mcat on this channel

[@leonardogyn]

I'd love to see the acid burn and cleaning mercury as next videos!!

[@chemicalaffair.]

i only use gravity filtration with hot solutions - that's way less work than heating up a buchner and do a vacuum filtration

[@stevewright8787]

Could you do a lab tour or glassware and chemicals you need?

[@NileRed]

+Steve Wright I am making the glassware video right now :)

[@jhyland87]

7:15 I've been waiting for you (or one of the other cool chem channels, DougsLab, NurdRage, Extractions&Ire, CodysLab, etc) to do a basic _chromatography_ video, and nobodys done it. I see a bunch of the University managed channels do them, but you should still do one! Its an awesome technique.

[@fsen1999]

depending on the type of chromotagrophy, the equipment requred to carry it out can be quite expensive. obv TLC isnt all that hard to do, but thats only a qualitative analysis technique, not a seperating technique

[@jhyland87]

@@fsen1999 i just mean column chromotography (vacuum, positive pressure, or just good ol gravity). Thats not exceedingly expensive. Definitely in the reach of NileRed.

[@Savage1872All]

Whats the advantage and/or difference between glass butch funnel top or ceramic? What is most all around useful size glass filter top to buy? Thanks

[@michalcarsky4546]

Hey bro, please can you Give me some good quality websites where to look for solubility and more details about substances ? Thank you really much. And I really appreciate your content and the way how you do that

[@SamTornado1701]

These are the most comprehensive Chemistry videos on KZbin.

[@user-ys3ls1ww8d]

.

[@acceptthetruthitwillsetyou2598]

Are you able to use an impure crystal to seed more uniform crystals in the same solution

[@mrwoodchuck94]

now i want a thausend min vid

[@teyrasiridae4704]

How do you pull a vacuum to remove the ethanol from the ethanol/water mixture? Won’t your solvent bump like crazy when under a direct vacuum?

[@bigguy8586]

Hi, I have a question about when do you use crystallization over distillation? Why? How do you choose the best solvent? Is water a good choice most of the time? Hexane? Naptha?

[@combustiblelemons9346]

Could it be possible to separate racemic methamphetamine from subisomer cuts that have say 10-15 C lower boiling point for the subisomer cuts (160 C) and then 170-175 C for racemic methamphetamine? The presumed cut is isopropylbenzylamine. An adulterant of methamphetamine added to give the appearance of large fake crystaline methamphetamine hcl. I doubt you know or if these subisomers cuts are possible or can even be removed this way since the boiling point is so similar but it's always something I've wondered about since users of the drug claim it is being cut this way and that a drop in potency occured in 2015-2017. DEA says they see it occasionally at their dedicated methamphetamine analysis only sees it occasionally. In 2008 the agency moved to not control it and decided it was just visually similar to methamphetamine Crystals. The full report requested in the "NFLIS 2007 annual report" on page 25 in paragraph one and two. I believe this was before the agency had a analysis lab dedicated to the stuff.

[@yazadtafti3224]

how do you know your chemistry so well? did you just do under grad or some post graduate studies or pharmaceutical school?

[@bonbadilmoi9325]

i would love to see an acid citric extraction and cristalisation.

[@bonbadilmoi9325]

***** from citrus juice......anything can be found pure in shops, i just want to do it myself, anyway it's the main purpose of the channel.

[@henryjensen2741]

Great videos! question, explain crashing out of solution

[@henryjensen2741]

not really a question, but who cares

[@NileRed]

+Henry Jensen It means that the thing dissolved doesnt have time to form nice uniform crystals. The solubility in the solution decreases faster than the crystals can form and it is kind of just pushed out of solution instead of coming out nicely. Not sure how good of an explanation that is.

[@henryjensen2741]

+Henry Jensen no, it makes sense. I'm a budding chemistry/biology enthusiast and I love the videos, keep it up!

[@tomasnavarrofebre5876]

Hi! Could you show us how to build an ion exchange chromatographic column with a cellulose matrix and an easy funding ionic resin to separate small carbohydrates? And cheap if it possible... :) I really enjoy your videos, thank you for your work!

[@mathewjoshy9774]

How is this project coming along?

[@5thDragonDreamCaster]

I'm trying to find a quicker way of separating silver nitrate and copper nitrate. I've made them both from sterling silver. In the past I added pieces of copper to the solution to crystallize pure silver then used that to make nearly pure silver nitrate. I looked around and found out that silver nitrate is not very soluble in ethanol but all I've found is that copper nitrate is soluble in ethanol but I couldn't find any numbers on it.

[@marnuel2944]

what are the impurities that can be rid of when doing urea recrystallization?

[@DEATH_TO_TYRANTS]

Would this be the same process that you would use to crystalize methamphetamine?

[@Doctorul]

I'm of watchlist now

[@Palerider1942]

i would love to see that denatonium benzoate one. i just wish you would be able to do it food grade and get some poor sucker to taste it XD

[@NileRed]

+Palerider1942 Poor sucker indeed.

[@glorky70]

Where do you get all of your glassware, and how much does it all cost you? Also, I'd like to see the effect of common acids on skin.

[@NileRed]

+lucas crow I am making a video on your first question as we speak... The video for the acids on skin will be uploaded soon. I just finished editing it.

[@barrysears510]

My cold packs nitrate is damp and the water bag is intact, the pack says a mixture of intravenous salts what do you think I have in it.

[@mattw3340]

Are there any exceptions to wanting the temperature to reduce slowly? Now I realize why my recrystallizations were always so excellent in the university lab and so terrible replicating at home. I couldn't let my impatience result in trying to speed things up by putting sodium acetate recrystallations in the fridge. And what about with respect to heating the mixture? Does it matter if we start by adding the compound to hot solvent, rather than to cold solvent then heating?

[@bigguy8586]

Good questions. If you find the answers can you let me know? I also tried to crystallize using freezer which has worked pretty good, but my choice of solvent is making residue which I need to purify through recrystallization. I failed my first attempt and lost almost all of my target chem.

[@adelinyoungmark1929]

I once tried recrystallizing urea with water as my solvent of choice, I failed to check solubility tables, suffice to say it never crystalized out and I still have a saturated solution of it sitting on a shelf in my lab. I really should put it in a desiccator.

[@kristinecarla6872]

what if you accidentally mixed benzoic acid with it? will it affect the product you assume it would be?

[@KimKim565]

Fully dissolving lidocaine in ethanol, and then letting the ethanol just vaporize off, will this cause recrystallization?Of course this will not get rid of impurities, im just curious..

[@nicougrikify]

Where do you do your research for experiments on things like chemical properties (eg solubility, etc) ? thanks

[@NileRed]

+nicougrikify Google! I dont really have a go to resource.

[@nicougrikify]

i find google sucked, so i got a CRC :p

[@youtubecomenter3655]

What's the worst chemistry mistake you have made? Will you ever do a lab tour?

[@NileRed]

+KZbincomenter365 Maybe not lab tour, but i will answer your first question when i eventually do my Q and A.

[@gauthtp]

Can you create crystals in supercool solvents like liquid nitrogen or argon?

[@Djoodibooti]

That chipped glassware tho.👀👀👀

[@SamTornado1701]

Sorry for my noob question, but temperature isn't the only thing that makes a compound more or less soluble in solution, right? BTW I vote for more "Technique Series"

[@g00gdobb3ers7]

the solubility of a liquid or solid increase with the increase of temperature, agitation such as stirring for example, and the addition of more solvent.

[@liamblackmore6688]

You probably got those accidentally when you wanted the ammonium nitrate ones right? For your potassium nitrate video, I also have been wondering what I should do with it. fertilizer maybe?

[@NileRed]

+Liamthepyro haha that is exactly where i got them. It turned out to be useful though. I used the stuff i recrystallized in this video to make hydrazine sulfate (luminol precursor)

[@TheZabbiemaster]

YAY long video's!

[@abhinilbose24]

I have a lot of calcium nitrate which is very wet after capturing water from atmosphere. I want to make dry. Can I follow this process for the same?

[@danielpascoa7203]

Can I use this methodology to create cannabis cbd or thc crystals? Or diamonds 💎?

[@jannikelspa8511]

I want to separate 2 salts. 1 with approx. 1000g/L (at 20°C) the other one with approx. 350g/L (at 20°C). I can't find literature for the solubility at higher temperatures. I want the more soluble one as clean as possible. I got quite a high amount of the less soluble salt in a very pure form. I repeated the process 6 times and still get every time a small amount of my less soluble salt. I dryed the rest to check the quality and it still has a lot of the less soluble salt in it.

[@Noah-hz5ll]

I have to ask... Top left corner. "Generic footage for intro." Editing error?

[@NileRed]

+Noah Alonge haha no. I put that there because i meant that the footage doesnt correlate to what i am saying. I wasnt very clear though. After i uploaded it i regretted it because i figured nobody would even know what i meant.

[@sarkar506]

hi nile myself prashant thorat from India, i made benzoic acid from sodium benzoate but i cant get needles on recrystalisation. can u answer the reason.

[@rooftopwarriorstv1453]

Need to find a way to do this rapidly at a huge scale

[@55editA]

Next one published should be Denatonium Benzoate :)

[@tmkhanh1503]

Just messed up this part in the iCho TST and now youtube recommend me this video. Im i being watched lol

[@ummuatiqahmaisaraismail6386]

How do you know for how many gram of solute need to put making it solve in the solvent? Any calculation or formula?

[@Enderbro3300]

You generally use excess solvent but you can look up the solubility of things in common solvents on Wikipedia

[@andrewlorick166]

Luminol!!!!!!!!!!!!!!!

[@dstnlockwood77]

Cleaning potassium metal next!!

[@dol--lod282]

Not gonna cover this in this video.. But the basic answer is.. WE'RE SCREWED!!

[@DROWXXI]

😂😂something heard in chemistry alot

[@sinenomine7405]

How about water soluble substances already disolved that you want to recrystalize Without impurities besides coloring agent

[@darrylwood2927]

Is there anything that is impossible or notoriously difficult to purify?

[@DeDraconis]

Hey, I might have just missed it but curious about something. So, you recrystallized urea pellets. What were they mixed with/what were the impurities? Or were you just showing us the method with a product that started out pure so you didn't have to worry about how impurities might mess with the demonstration?

[@user-fe3ty3ih5y]

What is this compound that is prepared?

[@fiacradoyle7474]

Can this be done with ammonium nitrate

[@dots5641]

And to think. We pee this stuff constantly 😂

[@christopherwellman2364]

Can fire blow backwards through a cylinder?

[@MrSmokingHott]

one more question!! what is ur job?

[@simontimon2]

Make a video on extracting Urea from urine

[@maxrr2609]

Make a long detailed video on your equipment -all - to teach my professor

[@shhhshhhh9201]

What liquid did you use

[@KingKillaL]

can somebody tellmy how to identify if i have urea or ammonia nitrate

[@computercat8694]

You have urea if you pissed in it and you have ammonia nitrate otherwise.

[@kemalk-gt7cu]

If we add nitric acid and ammonia to ammonium sulfate, won't it turn into ammonium nitrate?

[@James-co3os]

can you use denat ethanol?

[@TheSnakeboy11]

I'm procrastinating my trig homework by watching this #sendhelp

[@user-vx6ue1ew1q]

Same.

[@ajuntey83]

Can i use ethanol to recrystallize

[@mansoorramizy9801]

wow I didn't know that

[@aquaregia7004]

I'm trying to purify Ammonium nitrate fertilizer using recrystalization and need someone to help .I boiled off water until some AN crystal Precipitate out, then added a little amount of water to dissolve again, then I cooled it down to temperature about 1degree. In theory I should get 90 percent of AN but what I got was actually about 10%. I repeated the process for several times, every time was almost the same.Actually I did succeed once, that time I left the solution in the fridge for more than a week, perfect nitrate crystals were grown. I tried to recreate it but has also failed.

[@JohnDoe-pd2lh]

Ever have any luck?

[@KowboyUSA]

I store my urea crystals in my foot.

[@neonred7985]

can you use 100% ethanol

[@aajjeee]

That third one could be made in a rota vap

[@messiahyah]

other than chemistry what do you enjoy to do?

[@vapenation7061]

More chemistry.

[@erick5691]

Quick Question @nilered - What part of the re crystallization process determines the size of the crystals? Is there a way to control how the crystals actually form in terms of size? I've never really understood this, and in my experience, it seems thats agitation develops smaller (but more pure) crystals, while as less agitation creates large "chunks", but can have more impurities trapped. Is there a specific part of the process that can be controlled to create larger crystals, but also have impurities precipitate out in the same levels as agitation would after the first evap? I've yet to find an answer to this, so any insight that you could provide on this would be greatly appreciated!

[@TheDuckofDoom.]

Speed of cooling and quantity of nucleation points. slow and few=large ; fast and many =small, there is little that would make large crystals less pure by mass. Maybe you are not really crystallizing and just solidifying a large blob? Many variables, very generic. This is the basis for cooking fudge and heat treating steel where nucleation points and very particular cooling rates are used to control the crystal sizes.

[@rubenss25]

My personal suggest is to carry out two crystallization process. The first one as a normal crystallization, to get rid off the impurities, and then another one with a very slow cooling process to form nice crystals. This way you will lose some of your product, but if you only want to have nice crystals, it worths it.

[@SiexChannel]

Yeah here we go again

[@MrSmokingHott]

what is ur educational background? what university did you go to?

[@Hansulf]

None of them needed... Any Chem Grade teach you this.

[@jasonbourne7179]

You want my savings account details too?

[@christophereatmon8510]

Is that beaker broken

[@dots5641]

Lol. Here's a complicated crystallization. Crystallize chlorophyll

[@tdoge]

+Dan Swoboda The stuff in plants? That's everywhere. I wonder if chlorophyll still looks green in its crystal form, assuming it can actually form crystals.

[@dots5641]

+ShroudedPanda yes it can crystallize. Just extremely difficult

[@benthemusicalchemist]

+Dan Swoboda I'm guessing mixed solvent?

[@Gameboy2218]

Ben Canon There are different kinds of chlorophyll, a and b. Different yet they contain a different build carbon chain going off of it. So I'd say radiocrystolography as well as chromatography are needed to get both separated. But I doubt it would be worth it all that much.

[@GR3YS0RG4N1CS]

Ok I've got a little science project somewhat related to this, how would you best isolate and extract chlorophyll as a contaminant from an extraction of lipids with ethanol as the solvent in a fashion that is both highly effective and nontoxic? I've thought about using hexane as the starting solvent in a lipid extraction using the soxhlet extraction technique. I've read that hexane is excellent at dissolving lipids without extracting nearly as much chlorophyll or other water soluble undesirables (practically none) but it also only has a Recommended Exposure Level of only 80ppm. How close to 0ppm of hexane could one get in an extraction where the plant matter is processed in a Soxhlet extractor using hexane and then said hexane was distilled off and the hexane contaminated extract was then "washed" using some anhydrous ethanol at least 3x then vacuum purged for a couple hours? The reason why I ask the initial question about an ethanol extraction is because, if my preferred method of hexane extraction is unsafe no matter what methods are used to extract the hexane afterwards, I would like to find a method that 1. Can be done at home 2. Uses a relatively safe solvent, in this case ethanol (the hexane extraction would be conducted outside and under vacuum for hopefully obvious safety reasons) 3. Is at least semi automated and 4. Can produce an end product that contains little to no chlorophyll So basically my questions are, would the hexane extraction method I outlined be safe for human consumption, and if not how would you go about isolating and removing chlorophyll contamination from an ethanol extraction meant for human consumption?

[@nicks6980]

have you ever got a chemical burn