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Making Vanilla from Wood (Lignin)
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- Опубликовано: 12 май 2022
- It's finally here. In this video I will be using wood lignin to make various aromatic molecules like vanillin. Vanillin's structure is naturally found within lignin, and can thus be made when lignin is broken down.
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Years ago, a pilot plant was built in Seattle to make vanilla-related compounds for a paving project.
It was to be a catalyst for a resin; bonding fabric/gravel layers to construct roads, rather than using hot tar and asphalt.
Yes, the area around the plant smelled amazing at times.
Yes, everyone in the area grew to hate the smell of vanilla.
The project was dropped, the roadways materials didn't hold up to soil bacteria!
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.
I like nile red but sometimes I really don't need an hour and a half of "I need to stir the solution, so the first step is to put a stir bar in the flask, then with that done, the stir plate needs to be plugged in, after that I need to turn on the stir plate, at first I thought it was a disaster and didn't work, but then the stir bar started rotating, now, all I have to do is wait for the motion of the stir bar to start rotating the liquid in the flask....." 😑 So videos like this are really good.
Problem is, for actual chemistry work, papers DO want you to be that annoyingly exhaustive in your procedures and descriptions.
THANK YOU! THANK YOU! JUST WOW.
I was in a chem related server, asking around a year ago if someone could give me a paper on how to turn wood into vanilline, but you just spoonfed me :D
Thank you, awesome video :D
You might get more products if you control the oxidation time. Vanillin is sensitive to heat above 60C and will break down readily. As for the separation, you can try copying the bisulphitation that Borregaard uses, or use chromatography. Separating vanillin, p-hydroxybenzaldehyde, and syringaldehyde is rather tricky
you can purify aldehydes as their bisulfite adducts
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
Thanks for the video I was wondering how the artificial vanilla flavorings are made when I ate an ice cream few minutes ago. Searched the internet they told that it can be made from wood pulp, coal tar, cow poop, clove oil, castor, tree bark, and fermented bran. Now, nobody explained how the process turning them into the flavoring tho. At least now I know how it's made from wood pulp. Still 6 mysteries left to find out.
It turns out that cow dung contains a lot of lignin. That makes sense. Lmao.
Very nice! If you have some pyrrole you can make tretravanillin porphyrin. For separation the only think I can suggest is chromatography. Other than that distillation. Perhaps with vacuum.
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
Goeie shit. Nigel uploadt de laatste tijd weinig en jouw content vult die leegte perfect aan. Chapeau!
This was quite interesting, I went from being in the food industry (16 years) to now being in soaps and beauty products (3 years) , I make hard soaps, body butters, shampoos, moisturizers etc. etc. so I use a hell of a lot of ingredients that are used in both industries, I often wonder though what is in the perfume oils and hydrosols I have to use daily, some of the time I use straight up essential oils but most of the time the perfumes are chem based, the ingredients are listed on the barrels but it is all mind boggling names you would understand lol
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.
Thank you so much for not just cutting away from the pestle and mortar
Nice video ! I already made this project a year ago, but with low yield. I really love your channel !!
And no ones gonna talk about his accuracy in pouring from a beaker into a round bottom flask with such a small neck?
I'll definitely see you in the next one too. It's so cool that you can get flavors and scents from the most mundane objects. ☺️
I just love this channel
Lignosulfonates bought from ligma aldrich... How appropriate xD
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.
yours videos are awsome! I love watching them
You should do the process starting from wood, you can get DMSO too!
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
Just looking at melting and boiling points it should be very easy to separate these mixed carbonyls by steam distillation
I understand nothing, but when you added the acid I understood the fact that it resembled putting cream in coffee 👍👍👍
I love the Shrek heating mantle
No wonder you showed us that chemical cookie as a sneak peak for this vanillin
Funnily enough I was looking for ways to get vanillin (couldnt find vanilla sugar) but I ended up buying vanilla extract, might try this if isolating it from the extract doesn't work
Must have had a lot of aniline co-precipitating during that neutralization step. That and leftover nitrobenzene probably make your mixture very much not food safe.
I had this same thought immediately after he said "food safe". Nitrobenzene is a big no no.
At this scale you probalby can just go for a column chromatography to get vanilin if you have everything required for it.
Lignins can also be produced by gasification of wood, leaving charcoal as a by product, which with super heated steam treatment results in activated charcoal, another commercially valuable product!
Thank you for this video (and all of your other videos)
This is wild, I did not know it could be extracted from wood.
Now I understand why alcohol can also be made from wood, all we need is breaking down the polymer chains to simplier glucose melecules, very much like extracting vanilin.
What else could also be extracted from wood at this point?
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
2:07 yes i would like to drink the forbidden coffee ☕
Fantastic vid
Liked the presentation. Thanks. There are many ways to Vanillin; one is starting with clove oil (euganol) --- while I haven't looked this one up in a while, I think that the idea is to heat with a strong base, maybe NaOH? While I am not an accountant, it seems that Chemistry can be a business? Clove oil is sort of expensive, there in lies the rub. Maybe that is why most chemist end up in pharma?
This is cool, but I gotta say it looks like:
Tar -> Tar -> Tar -> Tar -> Tar -> Tar.
I'm actually interested in trying to replicate this myself. Do you think you could use a harsher oxidizer than nitrobenzene? I have some but its optical grade and was really expensive. (used for making Kerr cells)
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
Aw man I wanted to see the pulping process
What about leftover nitrobenzene? It is toxic, is it destroyed completely in the process? Or there can be some leftovers?
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.
Aah nice. The forbidden cookies
Hi, by any chance could I get the proportions and measurements you used for this experiment? I would love to replicate this experiment for my lab project and it would be extremely nice if you could send me the measurements. Thank you for the video and the information.
This channel is basically Nile Red but newer. Like it.
less cringe
Where specifically did you get the small container of lignosulfonate?
Question, at the end of the video, when you say you tried to separate them, what did you try? Are they difficult to seperate with column chromatography?
in some other universe:
Making designer drugs using trees cuz I SMOKE TREES.
Can u mention the amounts and concentrations?
I think if you put this brown powder in vodka will taste nice
Try doing TLC then do column chromatography to separate the products :)
Now give this to nilered to turn the vanillin and a box of plastic gloves into hot sauce
4:03 Forbidden coffee
Wood alcohol would be a great
bio fuel if mixed with sugar
cane alcohol + corn alcohol
or ethanol.
beautiful
4:04 (time not found; sorry, couldn't stop myself...)
Almost looks like a flame in the liquid for a sec, as you start adding the acid.
And from there you can convert vanillin to piperonal and use it to produce MDMA.
Hello, Im doing a school project and I would like to do different syntheses of vanillin and this version seems very interesting. Unfortunately I havent found good instructions on how to do this. Did you follow a certain paper here?
Would be nice to start with wood.
I have some doubt plz anyone tell the answer
Plz tell the quantity of nitrobenzene, calcium chloride, NaOH.
And what is DCM here?
Maaan I would have loved to see the whole process starting from wood :(
Was the choice of a Dimroth condenser a deliberate one?
no i just like this piece of glassware :)
Ah yes…the forbidden chai tea
Adding the acid into the dark solution really looks like adding milk to coffee
Wait, woody and vanilla aroma you say? It sounds like something that aged whiskey would have... Maybe this brown powder could be organoleptically tested while mixed with alcohol? As you said, these things appear in nature and I don't think they are toxic.
Syringaldehyde is a predominant component in aged whiskey from oak barrels
Need to invest in a funnel or two!
How dis, you clean the sintered glass funnel.
Super
Awesome!
What about column chromatography to extract the vanillin?
Cheers!!
I'm waiting for the video on making nitro musk
Who do you think you are? @nilered ?
Why not using column chromatography to separate the components?
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.
The sulfite pupling is to boil wood in the sulphuric acid? Just asking because I used to be living next to the paper producing company ... and the smell was terrible.
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
Column chromatography? Also I loved the multiple lignins you made
a thicc red liquid
a res thiquid
wait why tf are you not wearing gloves!
"Vanilla scent and flavouring from Sigma"
lignin? more like ligma!
Not only can you eat the popsicle, you can eat the stick. Total recycling.
Nice try but bad result. I expect better from your attempt.
Do you know Arboform?
en.m.wikipedia.org/wiki/Arboform