Making margarine from olive oil

margarine is an imitation butters bread that was invented in France in 1869 it was developed as a cheap substitute for butter and was made by churning beef tallow with skim milk the beef tallow which is a hard form of animal fat was a byproduct of meat production so it was both cheap and abundant when the hard fat was thoroughly mixed with the milk it resulted in a semi-solid spreadable material by the mid-1870s beef tallow based margarine was being sold across Europe and it even made it to the US however in 1902 the formula and the process changed when it was discovered that vegetable oils could be hydrogenated to form hard fats by 1910 most manufacturers were using a combination of hardened vegetable oils regular vegetable oils and animal fats and by the 1950s most US manufacturers had completely phased out the use of animal fats over the decades margarine has gone through quite a lot of development many brands no longer use hydrogenated oils or trans fats and a lot of them went completely dairy-free many brands also offer a whole array of variations that are supposedly healthier depending on the product the level of fat is also highly variable and it can apparently range from as low as 10% to as high as 90 in any case though the main idea across all margarine products is the same it's a combination of fat and water that has been thoroughly mixed together and allowed to solidify it solidifies due to the presence of hard fats which can be derived from natural sources like beef tallow or it can be made artificially by hydrogenation this hydrogenation process is what I'm going to be exploring in this video in particular I'll be hydrogenating vegetable oil which like other fats is made up of triglycerides in terms of structure this is what a typical triglyceride looks like we have a glycerol backbone and three fatty acid tails there are a lot of different fatty acids but in general there are two main types saturated and unsaturated in organic chemistry a saturated molecule is one that has only single bonds between the carbons and an unsaturated one has double or triple bonds in the world of fatty acids though it's pretty rare to get triple bonds what's important to notice is that the saturated fatty acid is very straight but the unsaturated one actually has a bend in it triglycerides that incorporate these bent ones don't pack as well together and they tend to be liquid at room temperature however we can actually change this by hydrogenation we can remove the double bonds and straighten out the molecules this allows the triglycerides to pack together more efficiently which both hardens the oil and increases the melting point with the oil now solid at room temperature it can be mixed with water and made into the spreadable margarine so for this little project I needed several different things from left to right I have aluminum foil palladium on carbon olive oil sodium hydroxide calcium chloride and methanol as we continue with the video you'll see exactly how each of these ingredients are used on a side note even though this is edible chem I'm not going to be tasting my product at the end because I filmed this before I came up with the idea for the series so yeah I still thought it was appropriate to label it as edible chem though because we are making a food product anyway I don't own a hydrogen tank so the first thing that I need to do is generate the hydrogen gas myself there are several different ways to do this but the method that I'll be showing is in my opinion the cheapest and uses the most easy to get supplies it's a pretty simple reaction between aluminum foil and a solution of sodium hydroxide but because I have to collect the gas and store it somehow it gets a little bit more complicated the setup that I'm using is just something I came up with using the glassware that I have but I'm sure there are many other ways to do this anyway this was the final setup at first it might look a little bit complicated but it's actually quite simple in the middle I have an addition funnel that I'll fill with a strong solution of sodium hydroxide when the salut allowed to drip in it will land on the aluminum and it will react to produce the hydrogen gas the gas will leave out the left arm and it will travel through the hosing to the trap all of the white stuff in there is calcium chloride which will pull out the water and dry the hydrogen as it passes through after the trap it will travel through another short section of hosing and it will make it to a balloon the balloon will fill up with hydrogen and this is what I'm going to use to temporarily store it okay so now that we understand what's going on I can actually start the reaction I made a really strong solution of sodium hydroxide and I filled up the addition funnel the concentration of the solution here really doesn't matter but it's probably around 50 percent or something I don't actually remember what I did I seal it with a stopper but I don't include a clip just in case there's a problem or something and the pressure builds up all of the other ones were clipped but I don't actually think it's that important the pressure inside a balloon really isn't that big and I don't think it's actually enough to pop the stoppers off one thing I did forget to mention though is that every single joint is sealed with a little bit of grease to make sure that hydrogen doesn't leak out anyway I'm ready to get things going now so I opened the funnel and I start to add it this reaction is extremely exothermic so the water quickly heats up and boils off if I keep adding it like this it's probably going to get out of control so I have to change a couple things I add a little bit of water enough to fill about half the flask and I also put it in an ice bath both of these things should slow down the reaction and make it not nearly as violent I let it cool down for a bit and this time when it's added it's much nicer it's important not to collect everything from the beginning because the stuff that initially comes out is just the air that was in the apparatus so I waited about thirty seconds or so before I attach the balloon when I feel like it's relatively full I take it off and I seal it by wrapping it around either a stopper or the plunger of a syringe then I attached another balloon and I started generating more hydrogen for now I only think I need two balloons so I close the addition funnel and I actually separate the hosing from the trap when I do this it's also important to close the valve that the balloons attached to otherwise I'll just lose all my hydrogen the reason to take this hosing off is it's going to be part of my actual hydrogenation setup okay so to get the reaction going I start by adding my oil that I want to hydrogenate which in my case is just olive oil in general oil is kind of messy so to clean things up and to complete the transfer I wash it with some methanol then I dump in my palladium on carbon catalyst and everything's topped off with more methanol I take away the funnel drop in a stir bar and then I attach this double adapter thing to the upper adapter I attach the hydrogen balloon and to the lower one I attach my vacuum pump I turn on the stirring in my vacuum pump and I pull as good of a vacuum as I can under the reduced pressure the methanol might start to boil a little but that's not a big problem once pretty much all the air has been taken out I closed the valve to my vacuum pump and I open the one to my hydrogen then I close it again and I repeat this evacuation cycle two more times the purpose of doing this multiple times is to just really make sure that the only gas in there is hydrogen hydrogen is the lightest gas so if there's any other gases present it's probably just going to sit on top and never make it to the reaction also for safety reasons we can't have any oxygen present because it's a pretty significant fire hazard anyway after the third cycle I'm ready to get the reaction going so I just open the valve to the balloon and this time I leave it open from this point on the reaction is pretty simple and we just have to wait for the hydrogen to be absorbed so what i'm doing here is hydrogenating the olive oil which is made almost entirely of tri Olien when the tri Olien is completely hydrogenated we'll get something called tri stearin which has no carbon-carbon double bonds hydrogen gas is diatomic which means that it doesn't exist as just hydrogen alone and it's paired with another one so it's h2 the bond between the two hydrogen's is relatively strong and it doesn't just like to spontaneously break apart if we were to mix hydrogen with just the oil not much would happen we really need the Palladium on carbon the Palladium on carbon is just very finely dispersed palladium that's supported on carbon powder which gives it a large surface area and makes it more reactive when the Palladium comes in contact with the hydrogen it can catalytically split it apart at the same time it also associated with the double bond and it mediates this addition of these individual hydrogen's to either side for most chemical reactions we do want to go to completion but oddly enough when it comes to making margarine we usually want to stop early this produces partially hydrogenated vegetable oils which you might have heard of before the idea here is that by only taking away some of the double bonds we can harden the vegetable oil but we don't make it too hard if we completely hydrogenated like what try stearin we're left with a very hard fat that is not going to spread very well unfortunately I don't know this process well enough to know when to stop and I was really afraid that I would stop too early so I decided I would just go all the way to completion and I accepted that my margarine would just be terrible there is a health benefit though of completely saturating everything because it means that I won't be making any trans fats when it comes to unsaturated fats there are two major configurations that we can have either sis or trans these terms refer to how the groups are oriented around the double bond insists the two non-hydrogen ones are on the same side and in trans they're on opposite sides in almost all natural fats so including things like vegetable oil it's almost exclusively sis double bonds however in the presence of a palladium catalyst it can undergo something called an isomerization and actually flip to become the trans over the years the trans fats have been associated with a lot of negative health outcomes so it's generally suggested to try to avoid them anyway it took about 40 minutes for all of the hydrogen in the first balloon to be absorbed during this time I started to see a bunch of solid forming in the flask and at some point a whole bunch of it got stuck on the side to get it all off I just blasted it with a heat gun and it very quickly melted away when the balloon was more or less empty I closed the valve and replace it with a fresh one I left for about an hour and when I came back the balloon had shrunk quite a bit and there was a whole bunch of white precipitate the white stuff is mostly try stearin along with other fully saturated triglycerides about an hour later this balloon is done as well I attach a fresh one and this one took about two and a half hours to disappear even though the balloon is shrinking I think the reaction is actually done and there's just a leak in the system because I plan for this reaction to go to completion this really isn't a big issue however if I wanted to partially hydrogenated and stop at a specific point I would need to measure exactly how much hydrogen I put in anyway now we need to separate off all of the saturated fat that I made the only problem though is that it's completely mixed in with all the Palladium on carbon so to fix this problem I just need to read azov' all the saturated fat by heating things up you can't see it in this shot but off screen I'm blasting it with my heat gun which is basically just a super-strong hairdryer as the solution heats up the fat will slowly melt and some of it will dissolve I eventually get to around the boiling point of methanol but there's still a bunch of stuff at the bottom this is fine though and purification will just take an extra step so while it's still hot I quickly filter it through some cotton and see light the stuff that filters through looks cloudy but it's just because the methanol is cooling down and some of the fat is precipitating the filtration was taking longer than I thought so I transferred everything from the round bottom flask to a beaker before the black stuff could solidify when everything passes through I do a quick washing with some hot methanol just to try to clean things up the methanol started to cool and some fat came out and started to plug the filter so I had to blast it with a heat gun ok so eventually everything is filtered and it's time to deal with that other black stuff by now it has completely solidified so the first thing I need to do is break it up into relatively small pieces then to separate the fat from the Palladium on carbon I add some dichloromethane I'm using dichloromethane here instead of methanol because the fat is much more soluble in it this way I can use a lot less solvent and I also won't have to heat things up I continued to stir things until the stir bar was relatively free then I place it on the stir plate for several minutes and all the fat dissolves to separate off the Palladium on carbon I do the same thing as before and I just filter it through some see light and cotton after everything passes through I wash it a few times with a little bit of dichloromethane as the Palladium on carbon dries it probably won't be a problem but it can sometimes burst into flames so keep this in mind dichloromethane evaporates really quickly so by the time the filtration is over you can already see some of the fat precipitating at the top to get rid of the rest I place a fan off screen and over the course of about an hour it completely dries up one important safety note though is that when evaporating solvents you have to be careful and do it in a well-ventilated area because it is a fire hazard on top of this dichloromethane isn't great to breathe in either so it's also a health hazard anyway it's eventually pretty much all gone and I'm left with this pasty fat now going back to my other batch which has the methanol I place it in the freezer for about a day to precipitate as much as possible then to isolate it I just filter it through a coffee filter I place it on some paper towel and over the course of a day or so it completely dries up I combine everything that I have and I turn the hot plate on to a medium heat everything that I have here should melt in a range of about 50 to 70 see the major component that I have here is try stearin but there are a lot of other triglycerides present so the melting point is going to have a pretty wide range I crank the heat up a little bit higher maybe to around 90 or 100 C just to really make sure that I get rid of all the methanol and dichloromethane it eventually pretty much stops bubbling so I take it off the hot plate and I let it cool over the course of about 10 minutes or so it completely solidified again I somehow lost the footage but to get it out I had to crack it into a few pieces my final yield of the saturated fat was 13 grams I'm not sure exactly which fat's I started with but if I assume i started with tri Olien and went completely to try stearin this represents about an 86 percent yield the two are so grams that I'm missing are probably still either just in the methanol or we're lost in washing and transfer steps anyway he'll decide it's time to make my terrible margarine right off the bat though there are going to be two major problems with my preparation first of all the fat I'm using is fully hydrogenated and not partially so it's really hard fully hydrogenated fats are normally used for shortening and I'm kind of forcing things to make it into a margarine and secondly I don't have a proper set up to mix things so even if I had all the right ingredients it probably wouldn't turn out great anyway on top of this I wasn't able to find any actual margarine recipe so I kind of had to make it up myself so what I ended up doing was using a combination of the fat I made regular olive oil lecithin and water if you want to know more details on how real margarine is made I've provided a link to another video in the description ok so the first thing to do is melt some of the saturated fat I break up an arbitrary amount and then I just blast it with the heat gun it can also be melted by either a hot water bath or a microwave but I actually found that this was faster when it's nice and liquid I added some olive oil I add the olive oil because I'm trying to balance the saturated fat with unsaturated fat and I'm hoping that this would kind of mimic a partially hydrogenated oil this mixture should have a lower melting point and when it solidifies it should be a little bit softer the next thing to add is some distilled water margarine is an emulsion between water and oil and the usual content is around 20% water because my mixing here is terrible you can see all the water droplets just sitting at the bottom the next thing that I add is lecithin which acts as an emulsion stabilizer so once I mix everything up and have a decent emulsion it should help to keep it like that so now with an arbitrary amount of all the ingredients added I stir things as quickly as I can at the same time I let it cool and I pretty much just keep mixing things until it's more or less solid it eventually gets quite thick so I just wait for it to fully cool down once it's at room temperature I try to take a little bit off using a knife but it's clearly still way too hard obviously I need to re tweak my recipe a little bit so I just go ahead and remelt it to try to soften it up I add a bunch more oil lecithin and water I do a quick rough mix then I blasted with the heat gun to liquify it and then I mix it thoroughly this time it didn't completely harden like before but it looked pretty disgusting at least now though it's something that's spreadable however it really did look and feel like I was just spreading plastic in any case though I did give it a try and it practically had no flavor at all and was definitely not something I'd want to eat anyway that's about it for this video I hope you guys enjoyed it and I'll see you on the next one a big thanks goes out to all of my supporters on patreon everyone who supports me will see my videos 24 hours before I post it to YouTube and they can also directly message me anyone who supports me with five dollars or more will also get their name at the end like you see here [Music]

Channel: NileRed

Views: 1,706,690

Rating: 4.921452 out of 5

Keywords: nile, red, chemistry, margarine, science, olive, oil, hydrogenation, edible, chem, food, trans, cis, vegetable oil, shortening, tallow, nilered

Id: drIm8_1CvjQ

Length: 20min 52sec (1252 seconds)

Published: Tue Aug 08 2017

Reddit Comments

[u/furryscrotum]

Why not just hydrogenate the oil itself at ~80 °C? Spreadibility only comes at around 50% oil/water and far less lecithin should be necessary. Flavour could be enhanced by addition of salt.