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