> chemistry > agents-acylants > anhydride-acétique > acetic-anhydride-from-vinegar-the-sulfur-chloride-route-otc-acetic-anhydride-synthesis-labcoatz

Acetic Anhydride from Vinegar: The Sulfur Chloride Route | OTC Acetic Anhydride Synthesis

LabCoatz - 2023-01-02

Acetic anhydride is one of those useful chemicals that home chemists just can't seem to get ahold of. In the United States, it's not illegal to own, but it's also not carried by most online stores like Amazon or eBay. And unfortunately, there aren't many published synthesis routes that people can (or should) try at home. The acetyl chloride route requires inaccessible acetyl chloride, and the ketene lamp method produces highly toxic ketene gas. And then, there is my route: the sulfur chloride route! It may stink (literally), but it only requires a distillation setup, vinegar, baking soda, and a few milliliters of easy-to-produce sulfur monochloride! 

A special thanks to @BackYardScience2000 for donating some of his chemicals to my channel! If you ever need specialty reagents, like acetic anhydride or phosphorus pentoxide, be sure to check out his eBay store:
https://www.ebay.com/str/backyardscience2000

Official inventory list:
https://docs.google.com/spreadsheets/d/1rCVAw273OwY7_gYJlgQ2q1RvEElIIN91y0Is0QkdxjI/edit?usp=drivesdk

EDIT: Backyard Science 2000 seems to be closing down operations, so if you want acetic anhydride, you'll either have to make it or buy from another seller like www.chemsavers.com

I included clips in this video by @THYZOID and @DougsLab, so be sure to go and check out their acetic anhydride syntheses as well!

WARNING: acetic anhydride and sulfur chloride are both corrosive liquids that produce irritating fumes. Proper safety equipment must be implemented. These chemicals might also be restricted in your area, so be sure to check your local laws before attempting this procedure. This reaction also produces sulfur dioxide gas, which is highly irritating to the respiratory system, so be sure to work outside or in a well-ventilated area.

0:00 Warning and intro
0:32 About acetic anhydride
1:02 OTC reagents
1:11 Making the sodium acetate
2:08 Drying the sodium acetate
2:52 Mixing the reagents
3:47 The main reaction
4:09 Observations...and a smell...
5:02 Distilling off the acetic anhydride
5:29 A second distillation w/permanganate
6:06 Burn test
6:36 Reaction with water
7:06 Neutralization: the circle of life continues
7:21 WHY WASTE IT???
7:37 BackYard Science 2000 promotion!
8:08 Conclusion and outro

@IdiotWithEducation - 2023-01-03

I love how many chemistry channels are popping up, it was about time to give a second wind to a newer and more advanced generation!

@BillAnt - 2023-09-10

Another good one is Chemdelic ... it's psychedelic and funny AF. ;)
My pet monkey told me that AA is a good potentiator for Mitragynine for passing the B2BB easier. You crazy monkey! lol

@jhyland87 - 2023-01-01

Your video quality is getting pretty awesome man.

@LabCoatz_Science - 2023-01-01

Thanks man, glad you enjoyed the video!

@superman9693 - 2023-08-28

Awesome! Now I can make my own H! 👍

@THYZOID - 2023-01-02

Nice! Didn't know this route would even be useful in an amateur setting but you proved it is.

@no_w4y - 2023-11-15

What an amazing route and the quality of the video is amazing, too. I always wanted to make Aspirin with my students but it is not worth the paper work to get acedic anhydride in Europe. thanks for the work putting in on YouTube. I am impressed!

@totalsynthesis - 2023-01-02

I've never seen such a unique and cool sponsor for a video - and even funnier he does ASMR videos, lol.
What a world we live in 🤔

@marcosazzi7788 - 2023-01-21

This is actually an extremely helpful way on how to make acetic anhydride and very easy and cost effective

@Dan-vq4pz - 2023-01-23

Extra props to backyardscience 2000!!! Solid seller. Bought like 3 helpings of his aminoguanadine bicarbonate when I was messing about with tetrazoles

@cooperpanasiuk5907 - 2023-01-02

I tried this procedure a while back and failed, it's good to see a video on this route to acetic anhydride. Good job!

@chemistryofquestionablequa6252 - 2023-01-02

Awesome video! I'd seen this prep on paper, but wasn't sure if it actually worked. Hell, there's a REALLY long thread on sciencemadness where people were trying literally everything else, I guess they didn't think it was worth trying on a small scale, you proved us wrong.

@BackMacSci - 2023-01-02

Awesome video! The production quality was top notch!

@LabCoatz_Science - 2023-01-02

Thanks man, glad you liked it!

@jamesg1367 - 2023-01-02

I'm struggling to decide whether death by ketene is worse than death by organo-sulfurous stench overwhelm.

@Blakearmin - 2023-01-02

Yeah, I'm saving this one.

@koreaface - 2023-01-03

Okay WAIT, this is so helpful. I have been trying to research how to make acetic anhydride because I was trying to synthesize paracetamol, and I couldn't figure anything out. I don't know how I haven't come across this method but thank you. I sorta gave up on doing a paracetamol lab and moved on to doing testosterone, but now I will do it next thanks to you.

@michaelknight4041 - 2023-01-16

Hello 👋 might I ask if you're trying to synth just the constituents of Paracetamol or the whole compound? I suppose you know that acetaminophen is pretty bad for the liver and can be separated from most opioid/apap combo pills with a simple cold water extraction since the acetaminophen is not water soluble but the opioid is. Good luck in your results.

@Sniperboy5551 - 2023-01-20

Acetic anhydride is more useful for an aspirin (or heroin) synthesis

@billynomates920 - 2023-01-20

@@Sniperboy5551 i've heard it can double or quadruple the strength of cannabis too although, of course, that would be a waste. i'd be using it for 'asprin' like you said. 😉

@jaredgarden2455 - 2023-01-23

You sound inexperienced, this advice is necessary.
Sulfur chlorides are nasty as all hell, not quite 'if you smell it your gonna die' kind of nasty but nasty enough to REQUIRE a fume hood and give you a really bad time, maybe even a headache.

Sulfur bromides might be preferable as they are less unwieldy and less volatile, however bromine itself can be a little nasty as well.

@chemistryofquestionablequa6252 - 2023-05-31

​@@michaelknight4041 lol,cold water extraction, that brings me back in time. Figured it out from a Merck index in my high school library. Btw, unless it was on the internet before 1996 or 1997 I might have been the first to upload the process.

@user-kd7to5xf9e - 2023-12-13

This was amazing

@felixer80 - 2023-03-19

thinks back to chemistry class being 95% book work

There are so many cool things you can make with basic chemistry. Thanks for sharing your experiences and experiments!

@jerrysanchez5453 - 2023-01-02

Great video.also a cool sponsor to have

@137bob3d - 2023-01-03

superb job. you get my vote

@sachabinky2915 - 2023-09-20

You are THE MAN!!!

@brannonmcclure6970 - 2024-02-10

Chemistry was the hardest science branch I studied at university. I learned a lot.👨‍🎓

@marconiandcheese7258 - 2023-01-03

You can be the next nile red! You are great.

@TOXXIE - 2023-01-03

A really good video! Keep it up!
Not looking forward to working with S2Cl2 again

@LabCoatz_Science - 2023-01-03

Gotta hate the sulfur chlorides man! They stink worse than thioacetone, imo!

@noviceartisan - 2023-01-02

Wow, that was an interesting way to do it. Get the feeling you picked it just so the contaminated sulphur dichloride didn't go to total waste haha xD Loved the gratuitous volcano at the end :)

@LabCoatz_Science - 2023-01-02

Yeah, the sulfur chlorides had to go, lol

@yellowflowerorangeflower5706 - 2023-01-19

New sub. I just like listening to you talk.

@arya6085 - 2023-01-02

This stuff smells so good. Its a bit of a shock the first few times but god I love vinegarish smells

@russellhamner4898 - 2024-01-18

Nauseating to me. I think it has to do with interacting with acetylcholine in the brain, and it may be a genetic susceptibility - vinegar smells absolutely repellant to me, and I don't even like to consume condiments that contain it other than barbecue sauce, but some people love it. The chemicals used to vulcanize the rubber in tires smell delightful to me, as bad as they are for my body, but some people gag when they walk into Discount Tire.

@pucktf - 2023-01-02

I almost fainted when I saw you drop your hole yield into water.
But I was laughing when you talked about been surprised when it formed a blob on the bottom of the flask. Had exactly the same experience when I dropped some into water and had drops at the button...

@russellhamner4898 - 2024-01-18

That's how you know it's legit! Not the most practical way to make vinegar though.

@ZZAZZZOZZZOZZZZLLZZZZ - 2023-01-02

gotta love acetic anhydride

@That_Chemist - 2023-03-01

this is actually a pretty good way to generate SO2 as well - if you don't have any bisulfite for some reason

@midwestchem368 - 2023-01-02

Dude another killer video! You're dishing out some great ones! Any chance your organosulfur compound is thioacetic acid(B.P. of 93C)? Or perhaps even the anhydride of thioacetic acid?

@LabCoatz_Science - 2023-01-02

It's very possible, good thought!

@alllove1754 - 2023-01-08

This was a new one for me. Clean, simple, surely still dangerous given the chems (if one does it without wisdom) but you definitely schooled us. Now, make a laser diode out of it (or a magnet)😊

@williamackerson_chemist - 2023-01-21

Omg I've done this before!! I stumbled onto some Wikipedia entry and decided it was possible and made a shtload of sulfur chloride and made about a hundred mLs of Acetic anhydride.

I never did test it only observed Acetic anhydrides boiling point and wasn't sure if I did it or not. Now I'm thinking it definitely worked. Thanks for your videos man your channel is very well done.

@williamackerson_chemist - 2023-01-21

Oh and my plastic lid did the exact same thing as yours. You cannot just store sulfur monochloride outside an ampule despite what it may tell you

@tayday424 - 2023-06-29

I know how bad that vinegar smelled as it boiled. Cool video!!

@ElGatoLoco698 - 2023-01-17

You're going to bet at 100 thousand subs in no time.

@upholdjustice372 - 2024-01-28

I wished you showed diagrams of the compounds and how they are reacting at a given moment at that temperature, would've helped in understanding......

Otherwise, great explanation, nice narration and quite encouraging to watch!

@rusty-dy3gz - 2023-09-12

It's crazy what you can buy if you don't mind being on a list.

@justinbanks2380 - 2023-01-10

So awesome! Love the videos and information.

Man I wish my science classes in high school and college were more hands on/experimental instead of mainly theoretical.

Definitely probably would've been safer/on less lists than doing practical experiments on my own at home.

Oh well, lol

@theeturnone - 2023-01-02

oh wow, a reaction we def made , a bunch of, in the 90s. and probably why it is on the watch list now. . LOL

but very nice. . @ 02:35 . . i seen that dark liquid, i thought it was starting to tar up or something.
However;
I was very impressed , that by the next shot, it was that half beaker full of pretty darn clean looking Sodium Acetat



*new sub to your channel. very cool projects you have going on for all ages. from high school organic chem students to people like me (45 year olds that have had chem synths in their past lives :)

peace,Eurn

@LabCoatz_Science - 2023-01-02

Glad you enjoyed it! Yeah, I'm happy to say the darkening of the sodium acetate wasn't too significant, although if I were doing this on a larger scale, I would do what Doug's Lab did and just toss the acetate into the oven, haha!

@billynomates920 - 2023-01-20

i would have given my eye-teeth for this video a few years ago but i'm a good boy now!

@OP-do7rt - 2023-01-04

lovely

@barfbot - 2023-09-21

i think my brain paused in crushed expectations there was no cod hitmarker on the drop spilled at 6:49 lol

@stephshighvoltagelab - 2023-01-17

interesting route to synthesis acetic anhydride, but I HATE working with sulfur compounds 😅(btw I am proud cuz subscribed you when you only have 900 subs)

@ZoonCrypticon - 2023-01-19

Could you please also synthesize phthalic acid (and then phthalic anhydride) from naphthalene ?

@Refertech101 - 2023-01-02

to really purify the sodium acetate it can be recrystallized in methanol hydrate, I have done this multiple times for making glacial acetic acid.

@f800gt76 - 2023-04-15

When I was studying in University, my friend want to perform one synthesis on organical chemistry class, but it required acetic anhydride. Book with method was soviet and everything was changed. In modern day Russia acetic anhydride is in List 1 or List 2 as precursor and making it (you cannot obtain legally) could cause some severe problems. He had to switch his efforts to a luminol synthesis

@kallah4999 - 2023-03-08

Blaming your eggy farts on the sulfure chlorides. Nice one, bro. Not many have this kind of logical inputs in their productions!

@Ecksterphono - 2023-01-02

I've made it. Good for polymers. Yup don't overheat, or you'll get sodium triacetate.

@killpidone - 2023-01-02

The forbidden salt and vinegar chip flavor

@jogandsp - 2023-01-03

Cackled at the circle of life audio

@jean-sebastienarteau7142 - 2023-01-02

Backyardscience 2000 gigachad

@papamidnightfpv - 2023-09-20

Convenient starting point to get sodium acetate without the day of boiling is to open an instant heat pack, the kind you snap to activate.

@LabCoatz_Science - 2023-09-20

True, although you'd still need to melt it down to drive off the water. Most instant hot packs use sodium acetate trihydrate, and this react is fairly particular about having anhydrous conditions!

@papamidnightfpv - 2023-09-20

True. The volume of vinegar I had to boil was ridiculous for the yield. I really like how you melted it, that was a gold nugget. I was considering acetyl chloride and acetic acid + ∆ = acetic anhydride + NaCl when I found this vid. There are some S and P compounds I would like to have but I would rather produce than purchase and I have neither element in hand. I have to go back and see how you produced your sulfur chloride.