Attempting to make oil from soap

this was quite interesting actually! I think cooking with fatty acids is quite interesting. You should make clean fatty acid and cook with it. It will probably taste a bit like acetic acid/citric acid, so not much enjoyable. Can you try to make mono- and di- versions with partial hydrolysis and then remove the soap? The result should be interesting and probably make good French fries too.

Adam Rak

Nope, just plain old Pd/C

Nile Red

Cool. Did you use Urushibara nickel for catalyst?

Silviu T

I also hydrogenated vegetable oil, ill post that later. Too many oil videos so far. I have made glycerin in the past using that method. I will revisit it to make biodiesel though. Eventually.

Nile Red

That sounds like it'd be cool to see. More importantly though you should talk to the producers at Modern Marvels about that piece of art you recorded. Im sure they'd pay you for that footage.

The Gayest Person on Patreon

Yes, methoxide is the intermediate that forms. Works as well with other alcohols - I have done this reaction with ethanol/ethoxide and isopropanol/isopropoxide too.

Silviu T

On a related note, I know that biofuel is made from vegetable oils by methanolysis. The triglycerides are cooked with (maybe?) methoxides. The methyl esters so formed are the fuel. That experiment might make an interesting supplement to the oil-soap-oil sequence you've got going here. Very nice. Thank you.

mrkhrdr@gmail.com

Nice video! I would definitely like to see you try enzymatic reactions. Trying a sequence or reactions as a biosynthesis would also be interesting.

Xekri

The amount of acrolein that was made was very bad.

Nile Red

Hm I had two years of chemistry in high school in the US but the only organic we did was a bit of nomenclature plus the general chem which ends up being relevant like electronegativity and the like.

David Abramovitch

Huh interesting. These days organic chemistry is confined to college and above? In my time (what? get off my lawn) we had 3 years of organic chemistry in high school.

Silviu T

Also, at around 280C glycerol suffers an internal dehydration with formation of acrolein. If (as you suspect) you went over this temperature, most of the glycerol may have been lost due to this parasitic reaction.

Silviu T

You may have better success with shorter chain fatty acids. Also saturated acids may behave better, and be less prone to degradation. If what you ended up with is just fatty acid, it's probably not oleic but elaidic (or a mixture of the two)

Silviu T

I have a 500 degree thermometer, if you want it I'll send it to you.

Silviu T

Still fun, regardless of the result.

jason black

someone mentioned the idea that if i did just purify oleic acid, I could try to make triglycerides again using a different method. I think i will use the one i mentioned in the video

Nile Red

haha thanks. As far as i know, It is the first recorded instance of glassware defication.

Nile Red

Very cool! I like the idea behind it, and even if it was a "failure" it still was a success. Just think, if you didn't make this video, the world may have not seen that Erlenmeyer flask take a shit on your bench - and that is a world I just don't want to live in. I'm just one guy but I do like the idea of trying this out with different reactions. Looking forward to whatever comes next either way!

The Gayest Person on Patreon

I am glad you found it interesting!

Nile Red

Im glad you liked it!

Nile Red

man, i didnt even think of that. Doh! I still have the stuff though, so maybe that might be worth a followup. I could try the other method, which is done at a lower temp and I think might be cleaner!

Nile Red

I like this kind of video too. It was really interesting talking about reaction mechanisms and techniques to try to make it work and also the IR spectroscopy. I'm just entering college so I haven't done o chem so I think this sort of stuff is a neat preview.

David Abramovitch

I really like this type of video. The fact that it goes in-depth into what you're trying to do really helps me in experimenting with organics.

Roger Lee

I feel that you just made super pure oleic acid now, contrary to what you started with (because you can never be sure what they put in soaps). Now with this pure stuff it maybe easier to make the triglycerides. Would doing the reaction again change anything?