How to make Phthalic acid and Phthalic Anhydride
Вставка
- Опубліковано 18 гру 2024
- This method was borrowed from both UA-camr users NurdRage and UC235.
In this video we will be extracting DEHP from vinyl gloves, and then cleaving the ester bonds to form alcohols and phthalic acid. The phthalic acid is then converted to phthalic anhydride by dehydration and sublimation.
This phthalic anhydride will be used in further synthesis to make phenolphthalein and phthalimide (precursor to anthranilic acid).
-------------------------------------------------------------------------------
Merch - nilered.tv/store
-------------------------------------------------------------------------------
■ NileRed is now available on Nebula! go.nebula.tv/n...
(when signing up with this link, a portion of your membership directly supports the channel)
Join the community:
Patreon - / nilered
Discord - / discord
NileRed Newsletter - nile.red/home#...
You can also find me here:
Facebook - / nilered2
Instagram - / nile.red
Twitter - / nilered2
Nile talks about lab safety: • Chemistry is dangerous.
This guy is gonna turn vinyl gloves into grape KoolAid.
TheToemeister My mom used to make Kool-Aid for us this way. I still remember her saying, "Kevin, ride your bike down to the hardware store and buy mommy some vinyl gloves. Then I'll make you some Kool-Aid !"
Other kids' moms had pantries filled with flour, sugar, baking powder, ... My mom kept phthalic anhydride, methyl anthranilate, ... Good ol' mom. A little weird, but a great cook.
Kevin Byrne LOL
WHAT THE ACTUAL FUCK YOU PREDICTED IT
0:41 he kinda implied that
@@davidrobbers5787 Yeah true but before I got there I saw the comment and was like holy shit lol
I worked in a plant. We used ortho-Xylene vapor oxidised with air over a catalyst at 400C. produced enough heat to run our power station. Made about 100 tonnes a day. then we esterified the phthalic anhydride with 2-ethyl hexanol, or decanol, or nonanol to make plasticisers.
How do you perform esterification? Just sulfuric acid and maybe azeotroping agent?
Only a chemist would talk about 50g of gloves instead of pairs or pcs...
Gloves come in different sizes
@@hunterellis9319 touche
Great job Nile. I'm an organic chemist myself and enjoy watching your videos. However, It would be great if you put the links of the previous videos that your are referencing during your talk in the description. TNX
why..WHY? Why do I love this channel and love these types of videos? I have no idea about 90 percent of it. I am no chemist and I know very little about any of what is being done or talked about...yet I find it fasinating and love watching it. LOVE it.
"I used 50 grams of vinyl gloves" lol
Same here
There is another way of makiing Phtalic acid and it is cheap. Oxidation of Naphthalene (mothballs) using acidified permanganate or chromic acid. What do you think?
Would also be interested in knowing?
SUCCESS! I picked up a 10 pack of "Mr. Clean" brand gloves at Dollar General. Weight was 41.19g. I did this in three days. First day, extraction. Second day, NaOH and reflux. Excellent phase separation. Put in freezer overnight. Day three, did sublimation, not quite a gram, but at least it worked! PS-used 1L flask in mantle/stirrer from Cynmar; nice units.
I am definitely going to recommend your videos to my students !
am I the only one who feels like eating the Phthalic Anhydride crystals
Yes. Yes you are.
+Riley Crocker i cant even think of bringing them near my mouth, fear of breathing them in... looks too much like asbestos
they look delicious! I hope it tastes like grapes!
Looks like candy floss
For anyone thats running this synthesis, if you instead use just 100mL IPA in the soxhlet extractor (instead of the 250mL), and also dissolve the NaOH in just 100mL of H2O (instead of 250mL), then you will get more phthalic acid crystals, some will crystalize out of solution before you even put it in the freezer. Just a suggestion.
I followed the steps listed here almost exactly, and while it worked ok, I had to boil off a lot of the solution to get a decent return of phthalic acid crystals. Just using less IPA and H2O made a world of difference.
perfect video as always :)
thanks!
is there a particular brand of gloves that you found to work the best?
Hi Nile,
I am a young Czech chemist and also your fan. I rly like your videos, because, they are interesting, exciting and help me to unite my teoretical and practical knowlage. Last week we decided to extracte few grams of phtalic anhydride, but we failed. After the ester hydrolysis and boiling the solution under refluxe, we left it cool for one day, but the solution didnn’t separate in two layers. We looked in chemistry text book and we found out, that isopropyl alcohol is miscible soluable in water and there is no reason, why the two layers should separate. I will be greatful, if you tells me, where we actualy made mistake and what is the uper organic layer? Thanks for your answer.
With sincerely Kamil - Lukáš Zach
maybe a bit late but, adding a salt to the water wil make te isoprpyl alchol less soluble in water, resulting in 2 layers.
Nice to see you're going to make the triarylmethane dyes ;) They're really fun to make :)
Your videos are awesome! Keep up the good work! :)
50 grams of gloves. XD
I'm still chucking at the phrase "filter off the gloves". It makes sense, but imagine being left with full pairs of gloves in your filter paper :D
*chuckling
I just 3D printed a keck clip for my 24/40 glassware. I noticed you were not using any clips. Did you use any grease?
You have a 3D printer? That's pretty cool! I noticed 3D printers were coming up often on your google+ page. What model is it?
I only use keck clips if my apparatus is going to have trouble staying together and I really only use grease when I do something under vacuum. For the most part, the ground glass joints stick together pretty well.
Wow, thats good news for me because I don't have any grease lol! My printer is a Da vine 1.0. It is very cool.
JMAPScience wow! You should make a video on it. One question: Is the printer limited to one plastic or can it use many?
TheKingOfChem No you can use every thing from ABS to bronze and glow in the dark. Even nylon.
Does the base ester hydrolysis also hydrolyze the alcohols to form ethanol and hexanol instead of 1-ethyl hexanol?
Good vids.
(1) How many cycles through the Soxhlet extractor is sufficient for full extraction of DEHP? I figured no more than 4.
(2) My proportions are a bit different. How do I know I got enough NaOH and HCl?
(3) Is there a way to detect whether I have DEHP before running the entire experiment?
(4) Do the acid and/or alkali react to the propanol?
(5) What are the side products? Would they be useful?
[I moved this from Facebook to here.
What brand of gloves did you use in this demo?
acetic anhydride synthesis?
I he has a video on that already.
TheKingOfChem I have made acetic acid, but not acetic anhydride! The synthesis of that is going to have to wait until the summer probably.
nono thermal decomp of acetone into keten and methane bubbled into GAA until waight gain is reached. no orto notrate some toluene and reduce it. and you can bake qualuudes
Am I correct in thinking that the PVC insulation from small wires would work instead of vinyl gloves? I'm assuming that my insulation contains DIDP instead of DEHP.
May I ask where you purchase you equipment and chemicals? Good, informal video by the way.
Mist of my stuff I got from eBay.
Is IPA only used for extract DEHP?
And other alcohols like n-propyl alcohol can be also work?
I think you can probably use ethanol or n-propyl alcohol. You would have to test that yourself though. Soak a piece of glove in the solvent. Remove it and see if it has become rigid.
Nile Red thank you for advise! I'll try it :)
Nile Red does IPA forms peroxides on prolonged storage?
I actually did not know this, but IPA does tend to form peroxides with prolonged storage. You need to be careful when distilling old IPA.
I never knew that.
Nile Red
Yes, I remember reading that somewhere but I wasn't sure. Thank you.
hello,would you make degradation of plastics to obtain monomers?
Do you know if DEHP is commonly used for nitrile gloves aswell?
Thanks! We have lots of it.
My reflux mixture didn't separate. Any suggestions?
Rsaramallac are you sure your gloves contain dehp
Thanks hopefully u r going to post next video soon ! Pls post a video for synthesis and crystallisation of Phenolphthalein or Phthalimide in next few weeks.
I have made phthalimide already and filmed it, so it should be up by the end of the week. I plan to get the phenolphthalein filming done today or tomorrow!
Glad to listen that. Pls check my comment on synthesis of p- nitro Aniline, i would like to know your opinion on my suggestion ! My knowledge is much based on theoretical foundation becos we are not much availed with facilities to carry out multistep synthesis, would like to know your suggestions to make such experiments comparatively easier
I think I commented on it!
Proforce vinyl gloves £60 amazon uk. 10 times more than regular gloves. Great vid😃
I have the same soxhlet extractor, how the heck did you fit 50g of cut up gloves into that? They must have been packed tight. I tried it now and it was close to 30g before I stopped packing in more.
What was the yield for this reaction
what kind of experiments can be done on nitrile gloves?
What concentration of isopropyl alcohol should be used?
Aren't pthalates endocrine disruptors? Shouldn't you be taking more precautions when sublimating them off and things of that nature?
It's more likely you get cancer from the gasoline vapors at the gas station than short exposure to phthalates in solution
Never knew phthalic was organic I use it at work on the daily
can vinyl gloves be substituted into PVC tubes?
My professor told me to add acetyl chloride and heat with pthalic acid to make pthalic anhydride. Is it right?
can ethanol be used as a solvent instead of isopropanol?
Here in Italy is VERY difficult to get isopropanol...
great video however!
Rubbing alcohol is usually 92% or 98% Isopropanol (also Propan-2-ol or Isopropyl Alcohol).
It is readily available from Oil and Gas companies as well as chemical suppliers from the internet. Electronics stores also sell it.
In the UK, it's the other way around. You need a license for ethanol, and getting absolute ethanol is almost impossible, unless you run a factory.
+Mao Zedong i live in italy, and here ethanol is sold just like isopropanol. just want to know i it is possible to extract it with it instead of isopropanol
Giampiero Baggi
Possibly. I know 1 litre of Propan-2-ol is about 10 Euros, 15 euros with shipping.
If you can get Propan-2-ol/Isopropyl Alcohol then I suggest that instead. Considering they're only used as a solvent you can probably get away with using it.
Check the MSDS or Pubchem or Sigma Aldrich information on it to see if it's soluable. Wikipedia might tell you if it's soluable or miscible.
Isopropyl Alcohol is a good reagent and solvent to have at hand. Brilliant at cleaning PCBs, electronics and glue as well as inks.
Its possible to make pure ethanol by oneself but its probably not legal in the UK.
fpuGermany
It's not. But it's not really enforcable.
Making Ethanol for chemical/non-edible purposes does exempt it from tax though.
You can apply for an IDA (Industrial Denatured Alcohol) License for free, like I have, and you can buy 20 litres of 98.5% or less concentrate alcohol a year.
You can recrystalise the alcohol to purify it and make it anhydrous, but if you want to by anhydrous out right, then you need a TCA (Total Concentrate Alcohol) License. You can only get that if you have a Public/Private Limited Company with a VAT number.
you should do a video on caffenol homemade film developer!
Why i always end up with a milk like liquid each time i poor the HCl in the heavy phase? 🙈
If no extractor is used, how much isopropyl alcohol should be used in the boiling step?
about a liter (at least that much was used in the capsaicinoids video). I tried my luck with the capsaicinoids using 200 ㎖ of acetone instead of a liter in a lab bottle, leaving it on the radiator for about 5 days and i got a nice goopy extract after evaporating it off
I got a white substance when the concentrated HCl is added, its so thick that it looks like milk or maybe even paint.
can someone guide at what temperature should I make phthalic acid to convert it to phthalic anhydride?
Awesome video as always Nile. Quick question, if I went the route without the soxhlet extractor, and used the iso and glove boiling, would it be better if I refluxed the solution using idk say a allihn condenser and reflux the solution, or would just boiling the gloves in the isopropanol be a better way of doing it? If anyone could leave some input it would be greatly appreciated
I believe refluxing is a better choice, as leaving the beaker open would result to a great solvent loss.
What is the software that you use on the video to animate the laboratory part
yeison sanabria I use sony vegas to edit everything
Can you use ethanol?
can i do this synthesis in a cours of 7 days ?
can someone guide at what temperature should my phthalic acid to convert it to phthalic anhydride?
i just tried again and struck out again. back to the drawing board!
Is the Soxhlet 250mL or 500mL? Also, is the RB flask 500mL or 1L? Will a heater/stirrer with a capacity of 500mL be strong enough for use with the water bath ? It has a 4.5" square base Thanks.
(I think I sent a message earlier, but I don't know where it went...).
***** I don't get the notification for messages so I never seen them... RBF is 500 and I believe the soxhlet is 250mL. I am not sure what you are asking about whether it will be strong enough.
Can you use ethanol for the isopropyl alcohol
+harsowutaq I recently carried out this experiment using ethanol. It seemed to work fine.
+Nick Beck Thank you
FYI: Vinyl gloves from Rite Aid Rx will not work. I got through fine, and after three hours, the refluxed liquid was yellow. Six hours later, there was no phase separation, thus the conclusion. Also, don't waste money on one of those $130.00 heat/stir units with the blue front panel. They will burn up regardless of what the manual says about cutoff, etc. Go for a better commercial unit!
Can you do something cool using antacid tablets?
+Matthew Ferrie What would you like to see?
+Nile Red extraction of the calcium carbonate, preferably using the fruit flavored ones (I have those.)
Matthew Ferrie If i end up needing CaCO3, Ill do it!
+Nile Red Hey man i recently did this on 80g of vinyl gloves only instead of using a soxhlet extractor i just refluxed it in 600ml of isopropanol, this went well and the gloves left over appear to have lost there plasticizer, but when i did the ester hydrolosis it started out alright, i added my hydroxide solution and there was a phase separation there, i then had it on reflux for 3 and a half hours and the solution changed from a milky white to a dark yellow almost orange color there was alot of white precipitate at the bottom so i added 250mls of water and dissolved the majority of it, however i have failed to get a phase separation and the entire solution just remains that color. its strange because everything seemed to be going perfectly up to this point. Would it be a good idea to simply add the hydrochloric acid and filter off the precipitate and recrystalize?
jared garden I would just try and see what happens. I had to try a few different brands before I got one that worked well. It is a pretty annoying process honestly
ive tried this before and failed, i believe the gloves i chose didnt contain the DEHP. I was wondering if anyone can suggest a brand that works. Im in the pacific nw of the usa if that helps. thanks.
You will have to try a bunch and see. I did it with a random brand I can't remember and it worked. Tried again with my local pharmacy brand and got some unknown white precipitate that wasn't phthalic acid.
how much yield did you get in this one ¿
+kshitij Ranganekar he doesn't know the initial quantity of plasticizer used in the gloves so i don't think he can get a yield value.
can I make phthalic acid from Terephthalic acid??
I dont think so
hello guy i am interested in the reaction of the anhydrid to the acid becouse i have a problem with this reaction in my company so you can coment me about this reaction ?
yeison sanabria is the reversible reaction my problem XD
To go from anhydride to acid, all it should take is mixing it with water.
can i use ethanol?
Lmao still wondering if I can
✨Scoopula✨
This process seems extremely wasteful, wasn't there a lot of the phthalic salt left in solution? couldn't you have added sulfuric acid instead to precipitate the less soluble sodium sulfate? That would free up the solution to be concentrated and hopefully precipitate more product. That or an extraction?
I think you mean calcium sulfate because sodium sulfate is water soluble
I want to make fluorescein which requires phthalic anhydride which requires other stuff which requires other stuff! wtf chemistry? How the heck I can get my thing done?...
Couldn't you have made this from glow sticks?
Knock Tzu ya Obito uchiha
Have you made phallic symbols?Ph?
My phallus is dehydrated.
How about methaqualone? haha
I never thought that there was so much plastisizer in vinylgloves. Yuck!
The capsaicinoid video: ua-cam.com/video/cQIMLEwQWL0/v-deo.htmlsi=SfmYosb6EzcUNpzO
shouldn't this be called 'extracting and converting phthalic anhydride' you're not exactly making it from raw materials. i supposed you'd need specialised equipment to actually make phthalic anhydride/acid though
can someone guide at what temperature should I make phthalic acid to convert it to phthalic anhydride?
+Namit Chhatbar as he said, only 30s to 60s heating is needed at one time, so just set the hot plate to high, it wouldn't do any harm