Turning soap into oil and making french fries

in my last video I made soap from oil but while I was working on it I wondered if it was possible to do the reverse reaction as in make oil from soap I thought that the coolest thing I could do would be to take soap convert it back to oil and then cook some french fries in my little fantasy I imagined eating the fries but I knew that it probably wouldn't be a good idea anyway this video is mostly just for fun and to explore the science behind this conversion making so from oil is very straightforward and surprisingly easy but going backwards is a lot harder based on my research this process is more than possible to do but just as a disclaimer before we start I wasn't able to get it working however despite it feeling I still thought this whole concept of going in Reverse could make an interesting video I'm just going to do a quick recap of the normal soap making reaction that we saw in the last video it starts off with oil or fat both of which are made almost entirely of triglycerides the triglyceride molecule is composed of a glycerol backbone connected to three fatty acids the bonds between the fatty acids and the glycerol are known as ester bonds and they're somewhat sensitive if I mix a strong base with triglycerides the ester bonds can be broken releasing glycerol and salted fatty acids these salted fatty acids are pretty much what soap is if I want to do this reaction in Reverse I'm going to have to put the triglyceride back together and remake all of the ester bonds unfortunately as with most things putting it back together is a much harder task the sodium salted fatty acids are first converted back to regular fatty acids and then they're reacted with glycerol to remake the ester bonds when I word it like this it sounds relatively easy to do but it's actually a lot trickier anyway to get this project rolling the first thing that I'm going to need is some soap the biggest issue with most soaps including mine is that they're made from a mixture of oils so there's a lot of different fatty acids in there even if I were able to flawlessly attach all of the fatty acids back to glycerol I can't really control which fatty acids go where for example the major fatty acids that make up olive oil are oleic acid linoleic acid and palmitic acid the major ones that make up coconut oil our lower casted myristic acid pull Medic acid and a bunch of others the triglycerides that would form from the reaction would be a mixture of all of these fatty acids a lot of them would contain both lauric and delay ik acid so they'd be kind of a hybrid between the two oils this would make the final product very hard to predict and it would make things really messy and hard to purify so to make things reasonable I'm going to need to use a soap that's made from just one oil as I said before my soap is made from a mixture of coconut oil and olive oil so unfortunately I can't use it also most commercial soaps are a mixture or have a lot of additives with a little research though I managed to find a bar of soap that claims to be made from pure olive oil it also says that it has no additives colorants or anything so it seems to be ideal for my purpose okay to start things off I need to grind up the soap I decided to do it manually using a cheese grater but there's probably an easier and more automated method in the next step I need to dissolve all of the soap into water and powder izing it first makes it go way faster it is possible to just chop the soap up into smaller pieces but if you do this be prepared for a long and painful dissolving process after a lot of pain and effort this is what I'm eventually left with all the soap was then added to some distilled water I mix it around and let it stir on its own for about 10 minutes hoping that everything would dissolve all of the powdered soap disappeared pretty quickly but there were still some chunks floating around these were larger pieces that I wasn't able to grind up very well but I decided to include anyway in hindsight I probably should have just chucked them out but in any case I need to deal with them now at room temperature it was taking forever to dissolve so I heated it up a little in the microwave after a little bit of warming and a lot of stirring everything eventually dissolved and were ready to add the acid when the hydrochloric acid is added it immediately reacts with the salted fatty acids and converts them back to their unsalted form the sodium chloride side product is just going to dissolve into the water but the fatty acids are insoluble so they're going to separate and float to the top the idea here is to keep adding hydrochloric acid until I get to a pH of around 1 or 2 this is definitely overkill but by making things really acidic we can be sure that we've reacted everything after I got to my target pH I continued to let things stir for about 10 or 15 minutes when I come back and I take the beaker off the stir plate the fatty acids quickly start floating to the top adding the hydrochloric acid caused things to heat up a little so now it's time to wait for it to cool when the solution is warm most of the fatty acids are liquid but as it cools a lot of them will solidify when it gets to a round room temperature the entire beaker is placed in a fridge I left it in the fridge for a couple hours and when I take it out the fatty acids have completely solidified I take out the glass rod and then using a metal spatula I separate the fatty acids from the beaker it can be removed as one large chunk but I recommend cutting it into smaller pieces all of the fatty acids are then scooped out and dumped into another beaker the liquid that's left over contains excess hydrochloric acid and sodium chloride to get rid of it it can just be poured down the drain with a bunch of extra water if I were doing this with homemade olive oil soap the water would also contain glycerol however because it's a commercial soap the glycerol has been removed just to confirm this i boiled down all of the water and I was left with just some dirty sodium chloride when I first started this project I was really hoping that the glycerol would just magically still be in there even though it's not listed on the ingredients the idea of isolating both the glycerol and the fatty acids from the soap and then recombining them to make the oil seemed really cool to me but unfortunately I'm going to have to use store-bought glycerol anyway moving on these are the fatty acids that I've isolated in theory they should be colorless or white but for some reason they're green the label said there were no dyes or colorings present so I guess the olive oil that was used to make the soap was just not super pure this is not at all to say that the olive oil they used was bad it just means that it wasn't heavily refined anyway now I need to connect them to glycerol to make triglycerides the typical way to do this is to react the fatty acids with glycerol at a high temperature in the presence of a base or acid catalyst with a little bit of research I found a paper that described using zinc chloride as the acid catalyst and they tested a whole bunch of different reaction conditions it was really convenient for me and they gave the optimal conditions to make the triglycerides so to get things started I turn the hot plate to a low heat and I melt the fatty acids then when everything is a liquid I start to add the glycerol when I'm done adding the glycerol I dumped in the zinc chloride the amount of catalyst that I use is just based on the mass of the fatty acids but the amount of glycerol that I need is a little bit harder to calculate I have no idea the exact composition of fatty acids I have here so I had to assume that it was all oleic acid oleic acid is the most abundant fatty acid in olive oil but it definitely doesn't represent a hundred percent so the numbers are going to be a little bit skewed the amount of glycerol that I calculate is going to be slightly lower than it should be but this isn't really a problem for this reaction I actually want to use less glycerol than is needed to make sure that the fatty acids stay in excess this way we can really promote the formation of triglycerides over things like diglycerides or monoglycerides so on top of the already low glycerol estimate I knocked off another 10% anyway once everything is added I crank up the heat I start to get a little bit worried about splashing though so just to be safe I transfer everything to an Erlenmeyer flask the goal now is to heat everything to 195 C and to hold it there for a hundred minutes so in theory this is the reaction that should be going on in the presence of an acid catalyst the glycerol reacts with three fatty acids to form the corresponding triglyceride and water as a side product the one unfortunate thing is that acid-catalyzed ester formation is an equilibrium reaction so the water that forms can go back and hydrolyze the ester and take the reaction in the reverse direction the major way that we're getting around this is by doing the reaction at a really high temperature at nearly 200 degrees Celsius any water that forms will be almost immediately boiled off without the water the reaction can't go backwards and everything should slowly be funneled to the products so in terms of the mechanism it's a pretty typical acid-catalyzed ester formation and I'm just going to quickly cover what's going on in the first step the fatty acid is protonated by the acid catalyst the protonated intermediate is then attacked by glycerol a proton transfer occurs which leads the formation of a water group electrons on the oxygen move to reform the double bond and the water is kicked off the hydrogen on the oxygen is picked up we're generating the acid catalyst and the reaction is repeated two more times to form the triglyceride so I finally reach 195 CE and I turn on my timer for a hundred minutes the solution is giving off a lot of white vapor and at first I thought it was water but I think it's something much worse than that I don't really have a way to completely confirm this but I think it's a combination of smoking fatty acids as well as a Kirlian from the breakdown of glycerol so not only is it irritating to both the lungs and the eyes but the smoking fatty acids are technically a fire hazard anyway a hundred minutes later the reaction should be done the moment it finishes I take out the thermometer and I cover the top with some plastic wrap the entire flask is then placed into a fridge for a couple hours a few hours later I pull it out and I have this brown goopy liquid this was really promising for me because I started it with fatty acids that were solid at room temperature but now I have a liquid even at refrigerator temperatures so at the very least some sort of chemical reaction has occurred to find out if I've actually made any triglycerides though I'm going to have to process it a little the first thing to get rid of is the zinc chloride catalyst zinc chloride is very soluble in water so it should be pretty easy to wash out it's important to remember that this reaction is reversible so when water is added we could start to get some ester hydrolysis at room temperature and with such dilute conditions this shouldn't really be a problem but it's still best to go as fast as possible it was all transferred to a large separatory funnel and then I waited for the layers to separate the lower water layer which contains a zinc chloride is drained off and discarded all of the oil is transferred to a small flask and I set things up for a vacuum distillation in theory this can be done without a vacuum but the temperatures required are much higher i insulate the flask with a bunch of aluminum foil and I crank up the heating if I actually did make triglycerides in this reaction the major one should be try Olien however the boiling point of tri Olien even under my full vacuum is still above 400 C there are very few thermometers that will go this high and the one I have only goes up to 250 C so because of this I have to go without a thermometer and it makes things a little bit more difficult instead of identifying different fractions based on temperature I have to do it by appearance which isn't going to be super precise anyway the first thing that came over was clearly water and this was followed by something that's solidified immediately in the flask try Olien and the other triglycerides that make of olive oil don't freeze at around room temperature so I assumed this solid stuff was mostly just fatty acid for a while all of the stuff that I collected immediately solidified but eventually this yellow oily stuff started to come over when it cooled down to room temperature it still didn't solidify so I started to get really hopeful that this was the triglyceride eventually the oil stopped coming over even when I increase the temperature a little so I stopped the distillation in the flask I was left with this boiling black liquid which completely solidified when it cooled cleaning this up was a pretty big mess and I'll show you guys that later in the video this was the final yield of my oil and it honestly looked really promising to see if it is in fact triglyceride I'm going to have to do some testing a simple way to test it is to use copper salts usually copper acetate but I only had copper sulfate on me I made a concentrated solution of copper sulfate and then I added a little bit of my oil I quickly mix things around a little bit and I wait to see if a color change occurs unfortunately the oil very clearly takes on this green color which indicates the presence of fatty acids it doesn't say whether triglycerides are present or not but so far it doesn't look promising I looked around online a little bit but I couldn't find a distinctive test that would actually tell me if I have an ester containing compound all the ones that I found would give a false positive if fatty acids were present so in my case they were pretty useful Asst luckily a very nice friend of mine offered to run an IR analysis so I went over to his lab ran a sample and then proceeded to be sad for Ganic molecules iron analysis can help us identify the functional groups that are present in this case we're hoping to see ester bonds from the triglycerides and we're hoping not to see carboxylic acids from the fatty acids both of these groups contain a carbon oxygen double bond called a carbonyl which is detected around the 1700 area on my graph I have a peek at 1709 so there's some sort of carbonyl present to know which one it actually is we can refer to an IR table with the standard values so here's the carbonyl section and we can see the ranges of each type unfortunately carboxylic acids appear in the 1700 to 1725 range so this is probably what I have the range for esters is a little bit higher and they're usually between 1735 and 1750 so this is a little bit sad because there's really no detectable presence of an ester based on this I suspect that what I have is pretty much just oleic acid I found an IR graph of oleic acid online and the spectrums are very very similar one thing to keep in mind is IR alone is not enough to characterize a molecule but in my case it does seem very likely that it's just a lahic acid so in the end this preparation was pretty much a failure however I think this might be the first and only time that a failure is just as success in my mind the fact that it didn't work here really just highlights how hard it can be to go in the other direction making soap is super simple and we just throw some base and oil together and boom we get our salted fatty acids going backwards though the process is much more involved and it's clearly more difficult to get going according to the paper I followed this really should have worked but for whatever reason it didn't maybe my fatty acids weren't pure enough or my acid catalyst was a low-grade this paper is advertised to be used with waste fatty acids though so I'm really not sure based on my recovery of fatty acid most of it clearly didn't react so it might be possible that a lot of the glycerol just broke down under heat anyway all of this isn't to say that this reaction can't be done the estera fication of glycerol and fatty acids is actually done frequently in industry however they usually make mono or diglycerides because they have some unique properties if I was really dedicated to get my triglyceride project going I would have to tinker with a lot of reaction conditions and I don't really think it's worth it I could also try a different procedure like the one I found here instead of zinc chloride it uses para toluene sulphonic acid as the catalyst and it also uses t hf as a solvent and molecular sieves as a drying agent some of you might be wondering how animals or plants do it and it's a lot more complicated at least in humans this is the pathway that's used it's not exactly something simple to just carry out in a flask like I tried in this video anyway that's a little bit off-topic but if you guys are interested I would like to cover enzymatic processes in the future after it failed I was pretty sad because I wasn't able to make oil for my french fries however I decided I would just do it anyway with the fatty acids so I chopped up a potato heated my oleic acid and then tried to cook them the amount of fatty acid vapor and a Kirlian that was being led off was pretty obnoxious I had to wear a mask and keep things really well ventilated or else my eyes would start burning after cooking for a few minutes I took them out and they actually looked pretty good despite how good they looked though I knew they would taste horrible so there was no taste test as I mentioned earlier the cleanup was a huge pain and to get things out I had to blast it with a heat gun the footage here is kind of funny and I don't think I have to tell you what I think it looks like when I got out as much as I could I let it sit in a base bath for about a week and then I was able to rinse the rest out anyway that's about it for this failure of a video however let me know what you guys think about exploratory processes like these and if you'd like to see me post more in the future in my last video I had a contest to give away the soap that I made and here are the winners I've already gotten in contact with everybody and shipped out the prizes but I'd like to thank everyone for participating in the future whenever I can I'm going to try to give away the things that I make or some souvenirs from videos a big thanks goes out to all of my supporters on patreon anyone who supports me will see my videos 24 hours before I posted to YouTube and they'll also be able to directly contact me anyone who supports me with $5 or more will also get their name at the end of the video like you see here in my last video I asked you guys to submit music for my end screen here but I think my intentions weren't super clear I'm not looking for a permanent outro or anything and I'm going to be switching the music every single video a lot of people have already submitted their music to me and I'm going to start including it as of the next video

Channel: NileRed

Views: 1,120,243

Rating: 4.9357123 out of 5

Keywords: nile, red, chemistry, soap, french, fries, fatty acid, science, oil, nilered

Id: HAieBBeS7Ss

Length: 21min 45sec (1305 seconds)

Published: Sat Jun 10 2017