Lab notes - Make Trimethyl Orthoformate Revisited With Sodium

https://youtu.be/XzaOhJv6go8 check out this video on sodium metal properties where u will find it

It forms sodium glycerate. That's true

Maybe reacting more sodium with methanol to make extra sodium methoxide would increase yield.

And another thing: It doesn't clean people's hands, unlike isopropanol. It definitely can't corrode stuff, like methanol can. And does it react with sodium to make something called sodium glyceroxide?

An Alcohol in chemistry is any molecule that contains an -OH (Hydroxyl) group bonded to a carbon atom.It doesn't imply that any alcohol is going to make you drunk, it's a notation for that "Molecular piece" so any molecule containing a hydroxyl group is considered to be an alcohol or to have an alcohol functional group. Glycerol has 3 hydroxyl groups so it has 3 alcohol functional groups. Ethanol is an Ethyl group (CH3-CH2-) bonded to a hydroxyl group (-OH) so it's CH3-CH2-OH . Note that chemical denomination is a thing and the possibility of something to make you drunk is another.

Also, Nurdrage, I saw your video on making formic acid from oxalic acid using glycerol. In that video, you said "glyceryl oxalate ester." Does this mean glycerol is an alcohol? Because I have not heard of glycerol suddenly being known as an alcohol, because it doesn't make people drunk, unlike ethanol.

Gotcha. Anyway, in terms of reacting it with methanol first to make sodium methoxide. According to the literature this doesn't increase yield. So i suspect the reaction with chloroform is slow enough not to be an issue.

NurdRage

I know, but still. Also, did I say 13%? I meant to say 13% extra. Yeah, a 13% extra yield.

I actually got around 33% yield. Still bad, but not 13%. Anyway, according to the literature, making sodium alkoxide separately gives very similar yield. Also, my 33% is consistent with literature. Xylene was dried with sodium. Not just water was removed, all reactive impurities that react with sodium were removed. Almost everything that reacts with TMOF also reacts with sodium so i suspect Xylene impurities to be a lesser problem.

NurdRage

NurdRage, the reason you only got a measly 13% extra yield is because chloroform reacts with sodium to make sodium formate and chloride. So you still have to make the sodium methoxide solution seperately and mix that with chloroform instead of doing them together. Additionally, you spent too long adding sodium; water reacts with trimethyl orthoformate to make methyl formate and methanol. Another problem is remaining impurities in your xylene. These impurities, even though they aren't water, are probably still reactive towards trimethyl orthoformate and therefore destroyed some of your product.