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This beautiful molecule to the left is a triglyceride. It is a molecule with a glycerol (or glycerine) backbone and three fatty acids attached to it. If you look at this molecule -‐ around the middle, before the OH bonds -‐ you'll see a double line. This is a double bond, which means this is an unsaturated molecule. In a saturated triglyceride, the carbons are single bonded, which are hard to break. (You can tell there are no double bonds in this triglyceride because it doesn’t have those double lines!) They are stable over long periods of time because there isn't going to be oxidation. Most of these are buttery fats like coconut oil, babassu oil, palm oil, and animal oils. Oils like beeswax and candelilla wax are also saturated (yep, I don't think of beeswax as an oil either, but it fits the description!) Jojoba is another saturated triglyceride, which explains its long shelf life. You can tell a single bond by the name "-‐ane". Squalane, for example, contains only single bonds, which means it is more resistant to rancidity. "-‐ene" means there are double bonds in the molecule. And "-‐yne" means triple bonds! These are going to have shorter shelf lives! In an unsaturated triglyceride, these double bonds can be broken easily and oxidation occurs. The more double bonds, the more potential for oxidation. This explains the shelf life of something like grapeseed oil. It has 3 double bonds in the chain (it is a C18:3 triglyceride, meaning is has 18 carbon bonds and 3 double bonds), which means it has three places where the bonds can be broken and the oxidation can occur! Most of the oils we use are "class 5: plant derived products, C18, unsaturated" meaning they contain 18 carbon atoms in those long chains. The unsaturated part means they have double bonds. Some of our oils have more than 18 carbon molecules -‐ like meadowfoam (C20:1) and jojoba -‐ but what's really important is the number of double or triple bonds when it comes to
you're familiar with stearic acid as a thickener. safflower. we'd have a saturated glyceride. sunflower. so they connect with other atoms to make up 8 electrons. meaning it has 18 carbon molecules and 1 double bond. it connects with another carbon in a double bond. the carbon doesn't connect with a hydrogen. and wheat germ. and one with a great shelf life! . In the case of a double bond in a fatty acid. so it's a long chain saturated fatty acid.blogspot. and it is easily broken so something else can get in that place of the missing hydrogen. avocado oil. A QUICK ASIDE ABOUT BONDING! Carbon has 4 electrons that want to connect with other atoms (the blue dots).THE CHEMISTRY OF OILS from http://swiftcraftymonkey. carbon likes to be surrounded by 4 hydrogen atoms to make up this 8 electron configuration. Sweet almond oil is a C18:1 triglyceride. Other C18:1 oils are olive oil. hazelnut oil. Normally when we look at a fatty acid chain. Atoms really like to have 8 electrons. FATTY ACIDS! If you're a lotion maker. Stearic acid is a C18 fatty acid. rice bran oil.com 2 rancidity. So we know these oils are going to last longer than the C18:2 oils like soybean. If we put three of these fatty acids together with a glycerol molecule. If you look at the unsaturated fatty acid chain. then a row of carbons. leaving the hydrogen out in the cold. And these oils will last longer than the C18:3 oils like grapeseed and borage. and cocoa butter. Hydrogen has 1 electron that wants to connect with other atoms (the red dots). then a row of hydrogens. As you can see from this picture. Atoms are so desperate to make up this 8 electron configuration. which means it is a long chain (C18) fatty acid without any double bonds. This would be a single bonded or saturated fatty acid because there are double bonds. sometimes they will bond doubly or triply with another atom to get to that number. we see a top row of hydrogen atoms. there are missing hydrogen atoms where the carbon atoms are double bonded! This the double bond.
com 3 But it's fairly uncommon for an oil to have three of the same fatty acids. And C18:3 is linolenic acid.6% linoleic acid. we are going to see an oil that is less likely to go rancid than one that is filled with linoleic acid (2 double bonds). so this is fascinating and all. They can also have different configurations (trans fats -‐ you've heard about those!) that determine if an oil is liquid or solid. In the picture to the left. and sometimes three. linoleic acid (C18:2 -‐ 2 double bonds). C18:1 is called oleic acid. and a C18:3 chain.THE CHEMISTRY OF OILS from http://swiftcraftymonkey. the three fatty acids attached to the glycerol backbone are different. but what does this mean for bath & body makers? Olive oil is a liquid oil that is unlikely to go rancid quickly.9% palmitic acid.3% stearic acid. as indicated by the double bonds. cottonseed. In this sample molecule. but it will go rancid eventually. one has 1 set of double bonds. it's called polyunsaturated!) can go rancid quite easily! What this means in terms of making lotions or other creations is this molecule has THREE double bonds on that last fatty acid. Olive oil has between 55 and 85% oleic acid. a C18:1 chain. It also indicates it's a liquid oil. 6.blogspot. and palmitic acid (C16 -‐ no double bonds). One is a single bonded fatty acid. 4. or palm oil molecule. . and because there's more than 1. and 2. The fatty acids can have differing carbon chain lengths and different types of bonding. and the other has three sets of double bonds! The fatty acids connected to the glycerol backbone determine what the kind of oil or butter. it looks like this triglyceride is composed of a C16 chain. we see a triglyceride with an oleic fatty acid (C18:1 -‐ 1 double bond). If oleic acid makes up the bulk of the fatty acids with its 1 double bond. I know C16 is palmitic acid. so it may go rancid more quickly than something like olive oil below. For instance. This could be a corn. which means it is unsaturated. The polyunsaturated chain (the C18:3 or linolenic fatty acid has more than 1 double bond. They tend to have at least 2 different kinds. Okay. as you'll see below with sunflower and olive oil.
It will still go rancid more quickly than a saturated oil.THE CHEMISTRY OF OILS from http://swiftcraftymonkey.blogspot. 2% stearic (C18).6% palmitic (C16). but I'll get into that in the sunflower oil post shortly! So what does this all mean? By looking at a oils and butter property chart you can figure out which oils will go rancid more quickly than others. and 5. Hydrogenation is the process of breaking those double bonds in advance and inserting hydrogen into the open spaces. You've turned an unsaturated fat (one with at least 1 double bond) into a saturated fat (one This is a high oleic sunflower oil molecule. with some stearic and palmitic fatty acids thrown in (less palmitic -‐ about 5. The high oleic sunflower oil will last longer than the regular sunflower oil because there are fewer double bonds to break. The down side to the high oleic sunflower oil is you are losing the linoleic fatty acid that can be beneficial to your skin. but fewer polyunsaturated fatty acids and more monounsaturated fatty acids (ones with 1 double bond) means you're going to have a longer shelf life oil. that double bond can be broken and the fatty acid now reacts chemically with oxygen to produce all kinds of molecules we don't want in our lotions that have horrible smells. 66% linoleic (C18:2). HYDROGENATION OF OILS When a molecule has double bonds. as it were. This makes an oil less likely to go rancid because you've pre-‐oxidized it. but it tends to go rancid far too quickly for my tastes! .6%). so it's going to go rancid quickly. You can look for specific properties the fatty acids can offer to your product. A high oleic sunflower oil is composed of 80-‐ 92% oleic acid (C18:1) and 3 to 10% linoleic acid (C18:2). I love sunflower oils in my lotions and other creations.com 4 Normal sunflower oil will have about 25% oleic acid (C18:1). What this means is about 91% of the sunflower oil is composed of fatty acids with 1 or 2 double bonds.
blogspot. Saturated fats lie in a straight line (more about this below). so they are more resistant to rancidity. And they have longer shelf lives because the double bonds have been eliminated. Oils can be saturated without the help of processing -‐ animal fats.THE CHEMISTRY OF OILS from http://swiftcraftymonkey. and illipe butter are all naturally occurring saturated fats.com 5 with no double bonds). so they pack together more easily. shea butter. eh? . You can see why this has some appeal. When triglyceride molecules are packed together well. they become a solid oil with a higher melting point.
which means they go rancid less quickly than the lighter oils. So what does this mean for us? A double bond makes the fatty acid kinky. So the heavier oils have fewer double bonds. and rice bran oil have fewer double bonds and are heavier. to the kinky line you see in the oleic acid (C18:1 -‐ 1 double bond) and erucic acid (C22:1 -‐ 1 double bond.blogspot. If you look at the oils with more double bonds -‐ grapeseed. an omega-‐6 fatty acid).THE CHEMISTRY OF OILS from http://swiftcraftymonkey.. or safflower oils -‐ you'll notice they are considered "light" oils. it can make the fatty acid contort in all kinds of ways. sunflower. (I'm not talking about fractionated oils here. as we see in the linoleic acid (C18:2) or arachidonic (C20:4 -‐ 4 double bonds.) The butters will go rancid in the distant future because they don't have any double bonds at all! . So we get a liquid oil.more on this in another post. avocado oil.com 6 FATTY ACID SHAPES Double bonds in a fatty acid shape can make it go from the lovely straight line we see in the saturated fatty acids like stearic and palmitic acid. When we add another double bond. which means it can't pack in as tightly as those without double bonds. Whereas oils like olive oil. found in rapeseed and mustard seed)..
RANCIDITY! The main destructors of our oils are heat. the chemical process speeds up.THE CHEMISTRY OF OILS from http://swiftcraftymonkey. water can also be our enemy. Put a bunch of these together and you have a liquid oil! In the trans configuration. and is cheaper than saturated oils like coconut or palm oil. resulting in an oil that behaves as a solid saturated oil instead of a liquid oil. Every chemical reaction has a rate of reaction. What exactly does this mean? In the cis configuration. Let's say it take 6 months for an oil to go rancid. In lotions. the missing hydrogen atoms are on the same side of the double bond (cis means "same"). You are unlikely to find a trans configuration in the oils we use in bath & body products as it usually arises out of processing and would likely cost more than a regular vegetable oil. so they have a straighter shape. When we heat it. doesn't need refrigeration. The molecules bend at the site of the double bond. the missing hydrogen atoms are on the opposite sides of the double bonds. it can be in either the cis-‐ or trans-‐ configuration. When we heat up a chemical . The double bonds are broken. Heat and time are pretty basic concepts. It has a higher melting point. then re-‐formed in the trans configuration. which is determined by various factors. The process of partial hydrogenation can force the hydrogen atoms in a normal cis configuration to become a trans configuration. dense lines like the saturated fatty acids. we reduce that time dramatically.com 7 CIS AND TRANS FATS When we have a double bond on a fatty acid. Meaning they can pack in more densely.blogspot. It can take a few hours instead of months! This is attributed to the rate of reaction. giving us a kinky molecule that won't pack in nice straight. The chain doesn't bend much. When we heat anything. and time. exposure to light. exposure to air.
isn't it? Time is what makes our oils go rancid. which means more possibility of colliding into a free radical. the faster the reaction. MECHANISMS OF RANCIDITY There are different ways by which our oils can become rancid. more about this later). even slightly.blogspot. even if we have stored them in a cool. The more bouncing molecules. dark place to avoid sunlight and heat! The main culprit in rancidity is the free radical. but it's such a nuisance! OXIDATIVE RANCIDITY The double bonds of the fatty acid react chemically with oxygen. at least with oils. So when we heat up an oil. So they are highly reactive. dark place with a wonderful bottle and seal! (Time is really not accurate as it is really the chemical reaction happening over time. Most chemical reactions are rated at SATP -‐ standard atmosphere (1 atm. which can cause oxidation. but it is still our enemy!) If heat can speed up a chemical reaction. And the oxidative process is pretty much the main cause of rancidity (with the possible exception of microbial contamination). I know we need it to live. it's the enemy of all things. Hence the suggestion to keep your oils in a cool. The free radicals that we worry most about are O2 (oxygen.. A free radical is an atom. or sea level) and temperature (25C). When these free radicals are involved in rancidity.. logically. molecule. but can be found alone in O form). looking for electrons to make up that complete valence shell. and OH-‐ (hydroxide).THE CHEMISTRY OF OILS from http://swiftcraftymonkey. This turns the fatty acid molecules into other molecules that smell awful! .com 8 reaction. And time. then. cold can slow down a chemical reaction. atoms really like to have 8 electrons and will do just about anything -‐ no matter how foolhardy! -‐ to get those 8 electrons.well. H2O2 (hydrogen peroxide. the molecules bounce around more. we call it an oxidative process (because of the oxygen atoms). or ion with unpaired electron. we increase the bouncing around of the molecules. As you might remember. most of them involving oxygen. the more collisions. which increases the number of collisions (this is called collision theory).
and most of them contain at least a few to fight rancidity! AUTO-‐OXIDATION Even in the absence of air. it's a really fast process and takes very little time at all if the oil is heated as well. ketones. we find oxygen. as well as beta-‐carotene -‐ and many oils contain these ingredients. Oh oxygen. which can increase the process of photo-‐ oxidation. you are so necessary but so annoying! Through the breaking of the double bonds. some of which are smelly ingredients! This process is a slow one when anti-‐oxidants are found in the oils. When the anti-‐oxidants are gone. This is why we use chelating agents (also called sequestering agents) like citric acid and EDTA to bind the metals so they won't be a nuisance in our lotions.THE CHEMISTRY OF OILS from http://swiftcraftymonkey. This is a much faster process than auto-‐oxidation. The process is even quicker when you introduce sensitizers like chlorophyll and various other organic substances (like blood. bile. and alcohols. but those shouldn't be issues for lotion makers -‐ I hope!) This is why we try to keep our oils away from strong light -‐ bright light can produce more oxygen in the bottle. PHOTO-‐OXIDATION The double bond interacts with a singlet oxygen (1O2). These are natural anti-‐oxidants found in our oils. epoxides. and neoxanthin. violaxanthin. and the process can be speeded up by exposure to light. HYDROLYTIC RANCIDITY Hydrolysis is a chemical reaction in which a molecule is cleaved into two parts by the addition of a water molecule ("hydro" is water. aldehydes. It is highly reactive with unsaturated lipids.com 9 This can be a result of photo-‐oxidation or auto-‐oxidation. the oxygens helps the the fatty acids break down into hydrocarbons (the H-‐C-‐H chains you see. Various carotenoids in our oils can slow this process -‐ derivatives of lycopene. and riboflavin. which is produced by the light. 4 hydrogens -‐ or ethane -‐ 2 carbons. (Which gives you a good reason to get some Vitamin E into your oils when you get them from the supplier!) Metal ions in the water at low levels can promote auto-‐oxidation. "lysis" is splitting"). and the water is split . The fatty acids are split away from the glycerol backbone. (And why we use distilled water that should not contain these metals!) The main culprit is iron. which can be methane -‐ 1 carbon.blogspot. 6 hydrogens). like lutein.
com 10 into H (hydrogen) or OH (hydroxide) ions. results in rancidity. Fortunately. our lovely fatty acid molecules are morphed into a new molecule and we have rancidity.THE CHEMISTRY OF OILS from http://swiftcraftymonkey. Interestingly enough. Glycerol (or glycerine) is formed as the fatty acids are removed from the triglyceride form and converted into salts! So hydrolysis can be a benefit for soap makers and a bane to lotion makers! MICROBIAL RANCIDITY Yes. when you consider how many ways a lotion can go wrong -‐ between rancidity and flocculation and separation and so on -‐ it's a wonder we can make them at all. Saponification is the hydrolysis of a fat and an aqueous base like sodium hydroxide or potassium hydroxide.blogspot. When this happens. our little beastie friends can cause rancidity in our lotions! (Which is why you must ALWAYS use a preservative!) Microorganisms use their little enzymes (usually lipases) to break down the chemical structure in the fat. we have anti-‐oxidants ready and waiting to stave off rancidity as long as possible! . Which. this process -‐ the hydrolysis. Wow. again. not the rancidity part -‐ is saponification or soap making.
seeking out electrons to fill its valence shell. I like to use it at 1% because it has such wonderful qualities for skin. specifically converting Fe(III) to Fe(II). be gone scurvy!). It comes in four varieties of tocopherols and four varieties of tocotrienols. When we add an anti-‐oxidant. it gets its electron back. so the cycle continues again. it's not very stable and can be esterified with phosphates. but anti-‐oxidants are huge weapons in our fight on ickiness! Free radicals are constantly running around in our lotions. Studies have demonstrated -‐ at least on lab rodents -‐ that it sinks readily into our skin and can inhibit lipid peroxidation. is one of the most common hydrophilic anti-‐ oxidants. Vitamin E is found in our stratum corneum and is secreted by our sebaceous glands to the surface of our skin. For our purposes. The interesting thing about Vitamin E is it can lose its anti-‐oxidating power. We will be focusing mainly on the alpha tocopherol. or ascorbic acid. The radical is content with its electron shell and bothers us no more! How awesome is that? VITAMIN E is one of the main lipophilic anti-‐oxidants you'll find for bath and body products. Unfortunately. and it's the most commonly used by homecrafters. VITAMIN C. you have to love chemistry! You can use it at rates as low as 0.THE CHEMISTRY OF OILS from http://swiftcraftymonkey. giving them a longer shelf life in our products. but you can use lower amounts.blogspot. But in an exciting redox process.05% in your creations or oils. .com 11 ANTI-OXIDANTS! Anti-‐oxidants can stave off rancidity in our oils.01 to 0. so it's unable to contribute an electron to the free radical. Ah. it works well with iron found in our water. and it can chase away scurvy (arrr. we provide that free radical with those electrons. It's present in high amounts in our skin. Nothing can make the possibility of rancidity go away completely. which is like oxidiation of the oils on our skin! It has also been shown to reduce sunburn irritation in mice (which just shows you albino creatures and sunlight don't mix!). which is the one you're most likely to see in suppliers' shops.
which increases the penetration of the other anti-‐microbial preservatives into the bacterial cell! EDTA is found in a salt form when we buy it from our suppliers -‐ either calcium or sodium -‐ to increase solubility in our creations.0 to 9.THE CHEMISTRY OF OILS from http://swiftcraftymonkey. meaning it's going to hang out mostly in the water section of the lotion. and rancidity takes place in the oil part of our lotion. We can use it in lotions and surfactant based creations at up to 0. These metal ions can precipitate in our creations.20% to get maximum benefits in our lotions and surfactant based products! What exactly is a chelating or sequestering ingredient? EDTA binds with metal ions (mostly calcium and iron ions) and keeps them from being reactive with our various ingredients. We know auto-‐oxidation of metals in the oils and water can promote rancidity. There's always a chance a beastie will adapt to the preservative in our lotion and learn to live there -‐ eek! -‐ but the chelating agent disrupts the outer lipid layer of the microbes (where stability is calcium and magnesium ion dependent). given its instability. . EDTA – CHELATING INGREDIENT EDTA (or ethylenediaminetetra acetic acid) is a wonderful polyamino carboxylic acid that has the ability to chelate. (Which is also another reason to use purified or distilled water -‐ get rid of those naughty metal ions!) On top of all of this metal binding goodness. and offer anti-‐ oxidizing properties to our lotions. And we only need to use 0. so adding EDTA to our creations will bind those metals to the EDTA and slow down the auto-‐oxidation process. although Vitamin C does have some nice properties for skin.0. As well. and can remove the scum that builds up on the tub after a bath. It is suggested you use tetrasodium EDTA for alkaline products (pH over 7) and disodium EDTA for products in the pH range of 3. it's probably not the anti-‐oxidant to use most in a lotion. forming a metallic solid that is really unpleasant. sequester.blogspot.20%. And the metal ions can keep our surfactant mixes from foaming as well as they should. EDTA can behave as an auxiliary preservative to kill off those nasty microbes. which is enough to do the job (but check your suppliers' recommendations). Add it to your water phase. it's hydrophilic.com 12 Honestly.
makes bath bomb creation a far easier process than using the monohydrate. which we can use to bind metal ions like calcium. which means you can use it in bath bombs even when its damp outside! (I used to get mine at Voyageur. Ask your supplier which one you have!) For other applications. It's also a key ingredient in bath bombs. which means it has a pH less than 7 (it ranges between 3. Including too much citric acid in something like a shampoo can change your hair colour! Remember "Sun In"? (It was all the rage when I was a teenager -‐ eek.5. anti-‐oxidizing. for me. The anhydrous is much less likely to fizz in high humidity.6 to 6. but they've stopped carrying the powder form. help prevent rancidity. which I've noticed tends to be more like a grain.com 13 CITRIC ACID – CHELATING INGREDIENT Citric acid (or 2-‐hydroxy-‐1. zinc. and cobalt to keep our products from experiencing auto-‐oxidation. There are two types of citric acid we can buy -‐ anhydrous (water free) and monohydrate (contains water). so the 0.13 to 6.2. I have found the anhydrous citric acid I've bought tends to be a powder and. nickel. we want a pH around 5 to 6 -‐ our skin is about 5. Citric acid is a weak organic acid. By binding these metals. magnesium. but as I've not used it in that context before. it can change the pH of our product. 2.4 depending upon the concentration). For something like a hair care product. For a lotion. so I get it at Aquarius.THE CHEMISTRY OF OILS from http://swiftcraftymonkey. we want a pH around the pH of our hair.1% suggested below should be fine!) Citric acid can be used as an AHA type acid in facial products. The difference in using citric acid as your chelating or sequestering agent is the pH changes you might find with it. It can also be used as a buffer (something that maintains the pH of a . I'm not comfortable making any suggestions for use. copper. It is a chelator like EDTA. and alter the pH of our lotions and surfactant mixtures. it also keeps surfactant mixes nice and clear! It also helps to boost the efficacy of your preservative. When we add it to a lotion or surfactant mix. it's irrelevant which one you choose.blogspot. 3-‐ propanetricarboxylic acid) is a chelating. I'm dating myself here!) It can lighten your hair if you're using too much of it! (You do have to use a decent amount -‐ say 1% or more. which is 5. and pH altering ingredient that can bind metal ions.
I'd suggest getting a pH meter (it's on my Christmas list) or using those pH strips. How much to add? You only want a titch when you're using it as a chelator and anti-‐oxidant -‐ 0. .blogspot.com 14 product) with sodium citrate if you're using things like AHA or Multifruit or Phytofruit or another acidic ingredient.THE CHEMISTRY OF OILS from http://swiftcraftymonkey.1% or so -‐ and this shouldn't be enough to change the pH dramatically. If you're using citric acid at higher levels.
We offer craft groups to teens. That would be great! If you really like this little tutorial thingie. two video game clubs.blogspot. body wash. please consider donating a few dollars to the Chilliwack Youth Library program fund (Our programs are collectively called Rated T for Teen).com sjbarclay@telus. We also offer parent-‐child crafting programs. If the idea of a young woman taking chemistry so she can learn more about bath and body products makes you smile…if the idea of youth enjoying the library and getting their own cards makes you happy…or if seeing a young person make her own purse and crochet scarves for Christmas presents. I promise! Happy formulating! Susan Barclay-‐Nichols http://swiftcraftymonkey. applying make-‐up. mineral make-‐up. Okay. students in alternate schools. We have had over 7. We’ve made packages for women in transition houses and collected for the food bank. you can reach me at sjbarclay@telus. and a Japanese pop culture program. please give credit to Swift or Susan Barclay-‐Nichols and note my blog (http://swiftcraftymonkey. the mooching really ends now. and pregnant and parenting teens. We’ve done so many bath & body projects -‐ hair care products. B. the mooching ends here…but they are pretty awesome programs. If you want to donate.C. Canada) and most of the funding comes from the volunteers’ pockets. tweens. We provide two card and board game clubs. We average 15 to 20 youth per group from every part of the community – foster children. Feel free to share these recipes with whomever you choose.com) or e-‐mail at sjbarclay@telus. If you can donate a little to our groups.net through hyperwallet (Canada) or through PayPal. home schooled youth. We provide different programs to youth at the Chilliwack and Yarrow Libraries (in Chilliwack. and so on. then please consider donating a little. bubble bath.blogspot. pregnant and parenting teens.. They really are amazing kids and so enthusiastic.THE CHEMISTRY OF OILS from http://swiftcraftymonkey.000 youth participate in our programs since 2005. we’d be incredibly grateful! Okay. and so on – which is a fantastic opportunity to share thoughts and discuss self-‐esteem. personal hygiene. and everyone in between. and we would love to be able to continue the programs and expand to other communities. All of our programs are free of charge and we provide all supplies for all craft projects free so no one is left out. as well.com 15 I hope you’ve enjoyed this little tutorial thingie on the chemistry of oils.blogspot.net.net . but if you are posting it on a website.
THE CHEMISTRY OF OILS from http://swiftcraftymonkey.blogspot.com 16 .
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