Today we're going to explore a chemically urban legend.

Is it possible to make acetic anhydride from a reaction between sodium acetate and nitrogen dioxide?

We're determined to find out.

Before we start though, a few words of caution.

Nitrogen dioxide is highly toxic and unpleasant, so make sure you use very good ventilation.

In addition we strongly recommend not attempting to distill the intermediate as it could explode.

Watch the video and see the results.

And then make your mind up if it's worth it.

Okay, let's get started.

We've weighed out 30 grams of anhydrous sodium acetate into a dry 250 ml flask.

It's a dry fine loose fluffy powder as you can see.

Let's get the flask attached to the apparatus and take you on a quick tour.

The nitrogen dioxide generation is going to be similar to the one we showed in a previous video.

So how?

Have a look at that for more information.

Here's a 500 ml flask in a water bath.

The large neck of this is stoppered so we can add reactants.

Then in the small neck we've constructed a calcium chloride drying tube for the gas using some cotton wool to keep the granules in place in the adapters.

Then we've got a still head which leads the gas to a small condenser.

And then a resurfing adapter with a gas takeoff which takes the gas.

And then we've got a flask to our ventilation unit.

And whatever condenses is going to drip down and into our flask containing our anhydrous sodium acetate.

Let's get a good ice bath set up so it's kept cool.

Our cooling water for the condenser is also super cool with a lot of ice and bags of ice in here.

Okay, let's start this baby up.

We'll let this cool for a few minutes.

You can see the condensation appearing on the outside already.

To make the nitrogen dioxide we've got just over 100 ml of 68% concentrated nitric acid here.

Let's get this in the gas generation flask.

And stoppered up ready.

Well in the last experiment we didn't use up our spare cupro-nickel change.

So we figured this would be a worthwhile cause for it.

We'll do our bit to help deflation along.

We're all set up so let's drop in some change.

It's beautiful to watch, but the NO2 is pretty deadly so you want to get your ventilation started about now.

We slowly rotate the flask around so that the condensed nitrogen dioxide can soak into the sodium acetate nicely.

The blue-green color seems to be due to the presence of nitrogen trioxide in the condensed liquid.

As the reaction is slower, the nitrogen dioxide will be absorbed into the sodium acetate.

And this keeps the beast alive.

The overall process takes about 30 minutes to complete.

There's a bit of NO2 escaping so in hindsight we should have probably used a larger more efficient condenser.

We'll let you watch the end of the reaction.

We've gambled all our spare change now and the reaction is pretty much over with no more liquid condensing.

We've got a fair bit of nitrogen dioxide liquid in here now as you can see.

So we carefully dismantle the apparatus.

There's a residual yellow-green color in the receiving flask.

And we allow this to chill in the fridge for an hour in order to allow any reaction to complete.

We decided to first try and see if this mix would work.

The mixture could be distilled.

We don't recommend you try this.

And skip to the next step.

But we'll show you what happened.

We're going to have to be a bit careful now because organic material in the presence of nitrogen dioxide.

And maybe even sodium nitrate or nitrite as by-products in the flask could create some fairly extreme fireworks.

What we noticed was that on heating, a lot of nitrogen dioxide was given off.

Even after 30 minutes.

After the flask had warmed above the boiling point of NO2.

So it's definitely formed some sort of unstable intermedia in the flask.

On gently heating there's also a very intense yellow colored vapor coming off.

More yellow than the brown NO2.

This starts to distill and condense at quite a low temperature.

And we've got a lot of nitrogen dioxide being emitted.

Once the vapor got up to the thermometer we could see the temperature of the condensing liquid.

This was around 50 degrees C.

Well we have no idea what's going on how.

And we weren't counting on this much NO2 being generated.

With organic matter this is now a potentially very dangerous situation.

So we stop heating and cool the flask down.

On dismantling the apparatus.

The first thing we noticed was a very positive reaction.

A very pungent, irritating and distinctive aroma.

That's acetic and hydride sun.

Nothing else in the world smells like that.

Smells like...

Victory.

So let's see if we can get it out.

We'll use 25 ml of DCM to start with to see if we can dissolve what's in the flask.

We added a little bit more until we had a suspension.

Excess sodium acetate or inorganic salts should be left.

And any acetic acid or acetic anhydride will hopefully now be dissolved in the DCM.

We've got a clean dry filter set up.

So let's filter the DCM solution.

Here's the DCM filtrate.

Now we'll distill off the DCM and we'll see what's left behind.

DCM boils at a low temperature.

So this is pretty quick and easy.

Once the temperature starts to rise.

We've got a nice, clean, clean flask.

We've got rid of all the DCM.

So we switch off heating and allow the flask to cool down.

After all that.

This is what we ended up with.

A slightly pale yellow colored oily liquid.

And it's definitely acetic and hydride.

The smell is unmistakable.

Well we've got 1.6 grams of product here.

But we're not sure how pure is.

This preparation isn't going to win any awards for efficiency that's for sure.

Let's drop some into water and see if it behaves like acetic anhydride.

Here's a little cold water.

That nice round denser than water block with the oxygen bubble on top.

That's very distinctive and again it looks like what we've got here really is relatively pure acetic anhydride.

It very slowly hydrolyzes and we've got an acetic acid aroma produced.

So the legend is confirmed.

Acetic anhydride is produced by the reaction of nitrogen dioxide with sodium acid.

But it's not a viable synthetic method.

Due to both the toxicity of the nitrogen dioxide.

And the seemingly very small yields.

But it was fun to try out.

Thanks to all our Patreon supporters to date who have supported us and should have received the Kimpler index.

We hope you find it useful.

Stay tuned for more reactions.

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See you next time.