we've got a fun packed video today we recently prepared some nitromethane so

experiments condensing this with some aromatic aldehydes first up we're going

to use panel in we weighed out 10 grams of our 99% food grade synthetic panel

in we know from experience that it's not completely dry but we don't think this

will affect the reaction we transferred this into a 100 mil

flask equipped with a magnetic stir bar

now for our nitromethane we prepared this in the previous video so click on

the link below if you want to see how we did this we've got ours stored on some

anhydrous calcium chloride granules to keep it nice and dry as you can see we

weighed out 4.4 grams which is a 1.1 molar ratio to the panel theme and

then we're going to add our nitromethane to the pan and then we're going to add our

and then measured out 15 mils of absolute ethanol we added the ethanol to

the nitromethane to form a solution then we added this solution to the

aniline in the flask and then got it stirring to dissolve there was no color

change observed this reaction needs a catalyst and we wanted to experiment

with using methylamine we prepared methylamine hydrochloride in a previous

video so we use this to start with this is about a gram of slightly damp slushy

methylamine hydrochloride we measured out 10 mils of absolute ethanol and

added this to the methylamine salt in order to dissolve it this dissolved okay

but with a small amount of insoluble crystals on the bottom which we assume is a methyl hypochlorite solution

we're going to add 5 mils of absolute ethanol to the methylamine as an impurity

ok now we need to convert our methylamine into the free base form which we need as

our catalyst so we weighed out 0.5 grams of solid potassium hydroxide and we

added five mils of absolute ethanol again this took a few minutes of

crushing and mixing in order to get it into solution most of its in now so this

do. We added the ethanolic potassium hydroxide solution to our methylamine

hydrochloride solution. A white precipitate of potassium chloride, which

is insoluble in ethanol, was formed. We left this for a few minutes to settle.

And the clear supernatant liquid on the top is our methylamine solution, which is

our catalyst. All of aniline has dissolved in the ethanol and

nitromethane now, but there's still no sign of a color change as you can see.

Let's add about one mil of our catalyst to the mixture. The mixture quickly

starts to turn yellow, and in about two minutes looks like this.

We set the flask up on a hotplate and with a condenser attached so we can re-flux the

mixture. Pretty soon on heating the mixture turnsablous

of an orange color. And then starts to turn red. We heat it

to a gentle reflux. And the mixtureMS turns red.

turn the beautiful cherry red color as you can see. We reflux for two hours and

then for a further 30 minutes we removed the condenser in order to allow some

ethanol and water to evaporate. Then we switched off the heat and allowed the

flask to cool slightly. We prepared a little cold water in a small beaker with

a pipette and we added this dropwise to the warm reaction mixture as it was

cooling. After about one mil of water was added the mixture started to crystallize

and solidify. At this point we then placed it into the fridge and chilled it

down for a few hours in order to ensure complete crystallization. Here's our

chilled crystallized reaction mixture.

It's pretty solid as you can see, so we set up for vacuum filtration and

scraped the solid into the center.

We washed the reaction flask out with about 30 mils of cold methadone and then

used this to thoroughly wash the mixture.

Wash the yellow solid

and then dried the yellow product thoroughly on the pump.

Here's our crude product. 7.9 grams of a bright yellow solid with a slightly orange tint.

Since the filtrate was bright red in color, it's possible that the orange color is due to

impurity.

As a crude product, this is a 61% yield on starting panel in.

We mixed the bright red filtrate we obtained with some cold water in a beaker to see if

we could get any more precipitate.

The result was an orange cloudy mixture with some brown goo which sank to the bottom.

We don't know what this is, but it doesn't resemble our product, so we discarded all

of this.

To recrystallize our crude product we used methanol.

We started with about 50 ml of hot methanol in a beaker, and added the crude product.

We kept adding methanol and heating the mixture around boiling point.

.

Nearly there.

It took about 150 ml to dissolve all the solid, at which point we then covered the beaker

and then let it to cool down.

Here's the result an hour later.

A mass of yellow crystal in the liquid.

Very pretty indeed.

We set up for filtration once again, and filtered the crystals.

We left them on the pump drying for about 30 minutes to make sure that they were completely

dry.

Here's the final product.

6.5gr of bright yellow fluffy crystals with the texture of a fine sugar floss.

They fluff up and soak safely in the

The volume is large compared to the actual weight of solid.

This is a final yield of 51% which is on the low side, but is comparable to some of the

more reputable reports we could find.

During the workup and both filtrations, we noticed a large amount of red filtrate, and

generally everything turned red.

We wanted to know if this was a reaction by product, or something else.

Here's some ice water.

And a small amount of the yellow crystalline product.

There's no color change.

And the yellow crystals are insoluble, just floating around in the mixture.

Now here's some hot water at about 60 degrees C.

And some more product.

Okay.

This time we've got the red color.

The yellow crystals seem to be slowly dissolving and creating a very intense red color in solution.

We're going to take a guess here and suggest that the red color is actually a decomposition

product, and that water is reacting.

One final test.

Here's a little acetone in a small beaker.

We dissolve a little of our acetone.

We put the product in it.

And it forms a nice yellow solution.

Now here's some ice water.

Let's add the acetone solution of the product.

No yellow precipitate, but an intense red colored solution again.

We're not sure, and this could just be some bizarre solubility behavior, but it seems

that the product is quite unstable, especially in contact with water, and especially when

in an organic solution.

This could explain why our yield is low, and give some clues as to how could work the reaction

of to give a better yield.

Just in case, we're going to keep our product very dry and store it in the fridge until

we find a future use for it.

Stay tuned for more videos.

Thanks for watching.