> chemistry > divers > pyrolyse > deacidifying-pyrolysis-oil-extraction-of-naphthenic-acid-from-synthetic-oil-hazel-chem

deacidifying pyrolysis oil / extraction of naphthenic acid from synthetic oil

Hazel Chem - 2019-11-02

hello you all in this video we will be working with the previously made pyrolysis oil 
to make the pyrolysis oil more usable we need to get rid of the acidic compounds that were formed during the pyrolysis process. Therefore we perform a simple extraction with sodium hydroxide and regenerate the naphthenic acids by reacting the sodium slats formed in the extraction with hydrochloric acid

Hazel Chem - 2019-11-02

hello you all in this video we will be working with the previously made pyrolysis oil
to make the pyrolysis oil more usable we need to get rid of the acidic compounds that were formed during the pyrolysis process. Therefore we perform a simple extraction with sodium hydroxide and regenerate the naphthenic acids by reacting the sodium slats formed in the extraction with hydrochloric acid
so now lets dive straight into the fun. To get started we prepare a alkaline solution by dissolving 25 grams of sodium hydroxide in 250 milliliters distilled water
it is important to use distilled water to avoid contamination with other ions furthermore the method I chose here is not the best … It is saver to add some water into the vessel before you add the hydroxide which will prevent the hydroxide from overheating when you fill up to 250 milliliter line
the solution we are making is around 10 percent sodium hydroxide. I am working with this exact concentration because in several papers I read on the extraction of naphthenic acids all agreed on around 10 percent base concentration and some hinted that a higher concentration will lead to unwanted sideractions or the formation of a emulsion that will prevent the phase separation which will make it impossible to separate the organic from the water layer
to perform the extraction we add 50 milliliters of the ten percent sodium hydroxide solution to 100 milliliters of the pyrolysis oil. This sample of oil I am using was stored for around 2 months to give the oil time to stabilize. This means that compounds like styrene and other reactive monomers had time to polymerize and yield a stable oil
after we added the hydroxide solution I am adding a stir bar and closing of the top of the Erlenmeyer flask to prevent crude oil from splashing out during the vigorous stirring. You can´t smell it through your screen but the pyrolysis oil smells really bad …. Plus it is has a lot of aromatic hydrocarbons in it which make it toxic and carcinogenic …. So even if it smelled like roses you would not like to smell it and that’s why I am working in my fume hood
so now back to our Erlenmeyer flask. As you can see the vigorous stirring forms a fine emulsion of the alkaline solution and the organic phase which is the oil. This allows us to react nearly all of organic acids in the oil and form their sodium salts which then dissolve into the water layer
I continued the stirring for 30 minutes to hopefully react all of the acidic compounds in the oil
after the reaction was done I stopped the stirring and prepared a separatory funnel to separate the water and the organic phase. But as usual something had to go wrong and I forgot to close the valve which lead to a spill out. When all the reaction mixture was transferred into the funnel some black carbon precipitate was left in the Erlenmeyer flask. So now we come to the second problem we encounter in this process. In the funnel an emulsions was formed which made it impossible to cleanly separate the layers. To overcome this I added more water and shook the mixture in the funnel. My guess is that this should work by reducing the concentration of base in the mixture thus reducing the emulsifying effect and yielding us two clean layers
And it worked the reaction mixture separated into two clean layers with the top one being our mostly deacicified pyrolysis oil and the bottom one water with sodium hydroxide alkali salts of different organic compounds and some pollutants which dissolved into the water. But what would such a workup be without yes you guessed it another problem. Remember the carbon precipitate in the Erlenmeyer flask turns out that the whole mixture is full of fine carbon particulate that clocks the valve of the separatory funnel which left me with the most undesirable option…. separating by hand with a pipette.

While I am pipetting of the water layer there are some things I want to discuss. I will redo this experiment because it is an important analysis step by determining the percentage of acidic compounds in the oil but the next time I will distill the oil first before performing the extraction. A distillation reduces the viscosity of the oil by separating the lower boiling fractions in the oil from the paraffin’s which make the oil that viscous. The other thing is that the carbon particulate is left in the distillation flask thus making it easier to work with the oil. The high boiling paraffin´s can then be dissolved in chloroform and their acidity can then be easily determined.
So now back to our naphthenic acids. After the separation the water layer is filtered to get rid of the fine carbon particulate. I used a vacuum filtration but a simple gravity filtration works as well. I don’t know how all of this carbon gets into the oil but my guess is that unstable compounds formed in the pyrolysis brake down under the elimination of nitrogen water carbon dioxide and carbon. The carbon particles then sticks together to form bigger carbon lumps that make the oil this hard to work with. After the filtration the now cleaner filtrate is transferred into a beaker to perform the precipitation of the naphthenic acids. Interestingly the water layer is now pitch black which could be due to very small carbon particles that were not filtered out or the dissolved compounds give that color to water phase.
Anyhow we want the free naphthenic acids therefore we add a stir bar to our filtered water layer. To regenerate the in water insoluble naphthenic acids we need to lower the ph into a highly acidic region where the sodium salts convert into the free carbonic acids. For this I am using concentrated hydrochloric acid because it has a low boiling point is easily washed away with water and has no oxidizing effect like sulfuric acid. When the acid is added you can see white clouds of naphthenic acid that form but are quickly dissolving back into the still alkaline solution. This happens because the hydrochloric acid first has to react all the hydroxide ions into water before it can react with the sodium naphthenate to regenerate the free organic acid and sodium chloride
So you might have noticed that I am using my real voice for this video and I want to know what you my viewers think about this choice which one do you like better? The robotic voice or my one. Please leave a comment to tell me your opinion so I can go on with the way that you like the most. Secondly we are now nearly at 6 thousand subscriber and I wanted to thank you all for your support comments and interest in my work despite the long time between my videos.
When you think no more naphthenic acid is crashing out you can check the ph using an indicator paper in my chase the red shows that the solution is now highly acidic just how it needs to be. An interesting fact about naphtanates is that the aluminum salts of naphthenic acids are used to produce napalm. Which I will explore in a future video just because it is too much fun to make your own real napalm. After the conversion into free carbonic acids is done the stirring is stopped and the naphthenic acid is filtered off. Again I am doing this with vacuum filtration but you can also use a simple gravity filtration. To get rid of any salts and hydrochloric acid the precipitate is washed several times with distilled water. After this the acids are dried on the pump for 3 minutes to get rid of as much water as possible
It is important to note that the filtrate has to be disposed of properly because there are still traces of many pollutants in it that are harmful to microorganism fish and plants. The Canadian oil sand industries biggest waste output is such water that is polluted with traces of hydrocarbons aromatic compounds and naphtanates. Over the years there have been several studies linking this cocktail of pollutants to cancer and other illnesses in humans. This information is to underline the importance that such chemical waste isn’t just poured down the drain.

I will repeat this process on a larger scale and work up the produced naphthenic acid analyze its properties and synthesize some aluminum nahptenate to make some napalm but for now that’s it
The next video is already filmed and is about the further insulation of the pyrolysis reactor to make it more efficient so have fun and don’t kill your self

miguel castelo - 2019-11-02

Keep your voice

marcofico1 - 2019-11-12

Could you next time also recristallyze them just to see how it looks when purified?

sushiquad - 2020-04-29

you should pin this comment to the top!

Paul Davey - 2021-02-01

I despise robotic voices. It's good to hear you!

MrMidnight - 2021-02-18

You could have filtered the solution before seperating the layer, often solids encurage the formation of an emulsion.
Sometimes it helps to add CaCl2 to the aqueous phase to make it more polar.

RICHARD SMITH - 2019-11-02

keep your voice over, dont use the terrible robotic grammar ignoring voice

Daniel Pache - 2019-11-02

Own voice is fine!

Eric Lotze - 2020-05-17

Another option is text on screen with no voice. Also some ai based TTS systems may exist that sound much better. Or just keep doing it like this video. Either way you're fine

Norm Hoback - 2021-03-02

kinda late to the party, just found the channel. Please keep your voice.

Bruno Esomonu - 2019-11-02

Please keep ur voice thank God I thought you would never speak

Eric Lotze - 2020-05-17

Another option is text on screen with no voice. Also some ai based TTS systems may exist that sound much better. Or just keep doing it like this video. Either way you're fine.

Ryan ._. - 2019-11-02

Finally after 3 months .
Its 3 am and your channel just popped in my mind.

piranha031091 - 2019-11-02

Great content! I prefer quality over quantity. ^^
(And I prefer your real voice over the robot one too!)

Danielle Spargo - 2019-11-02

i'm so glad to finally see the continuation of this series! i definitely prefer your real voice, to be honest. i like your accent a lot too :)

Hazel Chem - 2019-11-03

thx :D then it will be the real voice from now on

mfg hazelChem

Raj Odedara - 2019-11-05

Simply you are amazing...
You are doing a great work, kind of your fan.....
And yeah i won't die just yet ofc...

H M Silva António - 2020-02-17

Keep up with using your own voice, good job!

Haidar Bilal - 2020-12-05

Professor, you went back to the names of the materials you used in the reaction.

science_and_anonymous - 2019-11-04

Absolutely great video once again. I'll add this to my notification reminder so I see it early next time.

Stonehawk - 2019-12-10

i prefer your natural voice :D it feels MUCH more personal!

adrianpip2000 - 2019-11-04

I find the robotic voice very entertaining, tbh (reminds me of ChemPlayer), but your voice is fine too

Lars de Waardt - 2021-03-01

I generally check out when hearing the robot voice but as the subject of the video is interesting I kept watching.

Александр Агеев - 2019-12-22

You voice is good ! ))

Wallace Shao - 2020-11-27

use your regular voice. it matches well doing science explanations

Rob P - 2021-02-27

I'm waiting for the post explosion fallout video where you have no eyebrows.
Oh and your voice is great, keep up the good work 👍

sushiquad - 2020-04-29

thanks for the videos! i like them better with your real voice haha. i am studying pyrolysis of plastic to fuel for my phd so it is helpful to see videos of it being done at a bench scale (i think this would be considered bench scale??) . I'll be using a micro-reactor, but im interested in seeing how this can be done at an industrial level.

miguel castelo - 2019-11-02

Great video: but what if I just distill the pyrolysis oil to make a specific product/fuel

Hazel Chem - 2019-11-03

when you distill it there are still acidic compounds in the oil !

mfg hazelChem

Jonathan Moore - 2020-07-07

Your voice is wonderful. Keep using it for your videos!

CaliforniaCarpenter7 - 2020-12-28

I prefer your voice, dude. Do you have a video of turning pyrolysis oil to useable diesel?

Mihir Bendre - 2019-11-24

Please reply and let me know what you think I should do!

Lars Schönebaum - 2019-11-03

I know this Place

Thunderman Dead End Scribes - 2020-01-24

Humans voice are always easier to listen to because you can naturally emphasize.

Jamson - 2021-02-22

Great stuff!

PsychoToys - 2020-08-02

At what point of breaking down my plastics in to fuel can I find a buyer to refine it like you are doing?

Anthony Silva - 2021-03-01

Much prefer hearing your voice. My location:Arkansas USA


COOL VIDEO...........I did not even know what naphthenic acids were before this video. ALSO your voice is a LOT better than the computer voice

Mobeen Ahmed - 2019-11-09

You have a beautiful voice why wasting it. Also last sentance of the video was vary good you can make it a slogan of your channel. When your channel will grow you can also merchandise this sentence. Hehehe a kind advice.😅😁

Ahsim Iksnabac - 2021-02-23

I think you should use both voices, you could do a sort of conversation between the 2 voices.

Ross - 2020-11-30

Your own voice mate, it makes it far easier to understand.

Cory Milbury - 2021-02-27

Real voice!

bellybutthole - 2020-05-03

Your voice definitely.

dempa3 - 2021-02-23

Very interesting! Do you know if it is possible to DIY hydrotreated vegetable oil (hvo) as a diesel substitute? Maybe waste vegetable oil from restaurants could be used, abd if we could reduce the viscosity by hydrotreatinc it, it could be easier to use as a fuel in diesel engines. Additionally, did I understand correctly that one could use wood for pyrolisis, instead of plastic?

Eric Lotze - 2020-05-17

2:20 Smells bad...and toxic...and carcinogenic...and it's in a fume hood...and i'm wearing my gas mask


Mihir Bendre - 2019-11-24

Thanks so much sir

Dane - 2020-03-03

Hello, love your stuff. Can these products be made out charcoal/wood/dead animals?

riven main - 2021-02-15

this whole proccess looks like the worst nightmare of any chemist hahaha
they always hate polymerized crap and this project has so much of it

Y E B O I - 2019-11-21

You can narrate the work yourself... its cool

Ian Malcolm - 2021-02-25

Great accent Hazel! Keep your voice

ThePurpleRider - 2020-04-03

Very nice. As much as I liked the Robo-Voice, yours is much easier to listen to.

slamon ̇ ̇ - 2021-03-01

I like your voice, it's cool

حسن العراقي - 2020-10-30

Hello ... Thanks for the explanation .. I want to communicate with you via WhatsApp, is that possible?

Hazel Chem - 2020-11-01

hey you can absolutely write me an mail. my address is hazelchemistry@gmail.com

mfg hazelChem

mustafa atatuzun - 2019-12-13

your voice.

PsychoToys - 2020-08-02

If I had the intelligence I would be working with you on this. The world desperately needs this. Thank you.

Andreas Martin - 2021-02-08

good to see some people use the good old stuff from former east germany 👍👍👍

Ketus - 2020-02-09

The robotic voice sounds more dangerous and your voice sounds more scientist (y) (y)

danear2 - 2020-11-24

I sent you an email 🙏

Francesco Gabba - 2020-04-26

Hey Man, Good on you,,, i have really loved your videos so far,,, i was looking to build a pyro-still for wood and i ended un in your channel,, Bravo!... This process you are doing in this video, looks like what im after.. to be more precise, i would like to use the light fraction oils from wood pyro's in order to get phenols from them... could you give me any suggestions? or do you have any video about it? in the process i would like to use the least amount of external chemicals,,, i have a book that talks about it, but there are too many ways he is describing, also, the processes mentioned in that book are for very large mass of material, and i will be working with probably 2/3kg of wood,,,, Thanks a lot Brother,, keep it up!

Hazel Chem - 2020-04-26

thx for the postitve feeback. You can run wood through the same process and fractionally distill the product this should yield phenoles. This is how they did it historically. I hope this helps you

mfg hazelChem

brijesh kumar - 2019-11-19

Own voice

Trenton Markham - 2021-01-13

Any updates on the pyrolysis