Making Vanilla from Wood (Lignin) 

the bacteria ate our road 🤣🤣

Few million years too late! In the Carboniferous period there were no lignin eating bacteria, so wood and similar materials were not recyclable. Those roads would have been excellent in that period!

And those roads were probably still better than the road where my parents live. That road literally fell apart in a few months after reconstruction, and turned into gravel.

Problem is, for actual chemistry work, papers DO want you to be that annoyingly exhaustive in your procedures and descriptions.

Nice to see you here. 🙂

How does that work? Also How does a bisulfite adduct onto an aldehyde to make a sulfonate? Where’s the hydrogen atom from the bisulfite go?

It doesn't go anywhere. Every atom in the aldehyde molecule and every atom in the bisulfite become part of the adduct. If you're curious the sulfur bonds to the carbonyl carbon as well as the carbonyl oxygen as a hydroxy group, and the sulfonate and sodium charges form the ionic bond.

to clarify, the carbonyl carbon retains a single bond with the carbonyl oxygen, and the free bisulfite hydrogen forms a bond to the oxygen, which is not bonded to sulfur in any way

This was a mixture of aldehydes though

It turns out that cow dung contains a lot of lignin. That makes sense. Lmao.

What a lame job for a chemist

You would be amazed to see the proper name of those essential oils. Some are more complex and have longer winded names than fully synthetic oils.

Do you have a paper/prep about this compound? It sounds really interesting and I'd like to read it and look on its properties

Somehow i could only find easy to buy lignosulfonates on Ligma Balldrich, even though the material is so common and supposed to be dirt cheap, there’s not a lot of sellers. I suppose they normal sell this in 1000s of kilo’s at a time, or even the raw unpurified ‘liquor’ from the paper producers. Guess i’ll have to do with Ligma scam prices🤷🏻‍♂️

I was able to find suppliers of the sodium lignosulfonate, but only in 75 lb quantities for around $200. It's a great deal if you want to make a lot of vanillin. A better deal though might be to just buy sawdust and sodium metabisulfite and make your own. As I understand it, you pretty much just mix those with water and boil for an hour or so, then filter off the cellulose.

You can make DMSO if you're exceptionally stubborn and risk-tolerant, otherwise you should definitely just buy it lol

@@Alex-ee5pl DMSO is almost impossible to buy here, I like to watch videos that use things I can buy to make things I can't

You should be far away from civilization if you plan on messing with organic sulfides. Not only are the processes and materials very toxic, you could incite mass panic by making the whole block smell like a gas leak

I had this same thought immediately after he said "food safe". Nitrobenzene is a big no no.

Nilered did an ethanol from toilet paper video. Toilet paper = cellulose from wood.

You can use wood as a feedstock for all manner of things if the alternatives are more expensive, (somebody correct me if I'm wrong here) a few examples are as follows: - You can heat or steam distill the raw wood in chip form directly it to drive off and collect useful volatile components - You can destructively distill wood (with the product differing depending on the type of wood) or wood resin (which in itself can be refined into many useful products) to create wood tars which you could treat similarly to coal tar. - You can heat it in a reduced oxygen atmosphere to collect carbon monoxide/wood gas to use to make simple chemical compounds to feed into other processes, for example the water gas shift reaction which turns carbon monoxide and water into carbon dioxide and hydrogen which produces a useful amount of hydrogen gas - Mixtures of carbon monoxide and hydrogen can be used to create more complex liquid hydrocarbons via gas-to-liquids processes like the Fischer-Tropsch process, or the hydrogen and carbon monoxide can be used to synthesise methanol (which is industrially very important itself) that can be used in the Mobil process, methanol-to-olefin or other similar processes - Wood gas can otherwise be filtered and then burned in a four-stroke gasoline engine (with only very minor modification) or a furnace - The remainder left after heating wood in an oxygen excluded atmosphere is charcoal which you can steam treat to produce activated charcoal

@@CATASTEROID934 An excellent list; but not only that you can have potassium carbonate from the ashes, acetone, methanol and acetic acid from the distillate; its amazing how much you can do with it.

I hear you can even build houses out of it and cook food with it.

Not extraction - derivitization

less cringe

You will have to look in literature for the specific oxidizer you want to use. Selection for vanillin could be terrible for some.

I wonder if hydrogen peroxide could work in these conditions, particularly from sodium percarbonate? In literature the main alternative is to use oxygen gas with copper hydroxide catalyst in strongly basic conditions, but it usually requires high temperatures and pressures

Nitrobenzene smell is really strong and it wasn't present after the crystallization, so i don't think there is any significant amount left. I can't find any info about miscibility of nitrobenzene and DCM, so i don't know if part of it is extracted. It had dried for a decent time so if any was left it might have slowly evaporated off.

no i just like this piece of glassware :)

Syringaldehyde is a predominant component in aged whiskey from oak barrels

No they use sodium sulfide, base and heat usually. Sulfite pulping is known to stink and be a more dirty method. Sulfuric acid wouldn’t really produce a smell. I believe sulfite pulping is mostly being phased out though, since improved Kraft pulping methods are more efficient. There are methods which do use sulfuric acid (like organosolv) but i believe not for sulfite pulping.

@@Chemiolis the improve kraft processes are more about reducing sulfurous off gas and producing a less acidic pulp to produce acid free paper while keeping the cellulose as intact as possible. It still uses sodium sulfide.

@@Chemiolis Aha. Thank you

Everyone hates column chromatography ;). But in all realness i couldn't really find a reliable source for the solvent system and i assumed it would be some annoyingly large column packing length to get decent separation with such similar compounds.