Cleaning chemistry – the awesome power of soap

Well, times are interesting at the moment, aren’t they? I’m not going to talk (much) about The Virus (there’s gonna be a movie, mark my words), because everyone else is, and I’m not an epidemiologist, virologist or an immunologist or, in fact, in any way remotely qualified. I am personally of the opinion that it’s not even especially helpful to talk about possibly-relevant drugs at the moment, given that we don’t know enough about possible negative interactions, and we don’t have reliable data about the older medicines being touted.

In short, I think it’s best I shut up and leave the medical side to the experts. But! I DO know about something relevant. What’s that, I hear you ask? Well, it’s… soap! But wait, before you start yawning, soap is amazing. It is fascinating. It both literally and figuratively links loads of bits of cool chemistry with loads of other bits of cool chemistry. Stay with me, and I’ll explain.

First up, some history (also not a historian, but that crowd is cool, they’ll forgive me) soap is old. Really, really, old. Archaeological evidence suggests ancient Babylonians were making soap around 4800 years ago – probably not for personal hygiene, but rather, mainly, to clean cooking pots. It was originally made from fats boiled with ashes, and the theory generally goes that the discovery was a happy accident: ashes left from cooking fires made it much easier to clean pots and, some experimenting later, we arrived at something we might cautiously recognise today as soap.

Soap was first used to clean pots.

The reason this works is that ashes are alkaline. In fact, the very word “alkali” is derived from the Arabic al qalīy, meaning calcined ashes. This is because plants, and especially wood, aren’t just made up of carbon and hydrogen. Potassium and calcium play important roles in tree and plant metabolism, and as a result both are found in moderately significant quantities in wood. When that wood is burnt at high temperatures, alkaline compounds of potassium and calcium form. If the temperature gets high enough, calcium oxide (lime) forms, which is even more alkaline.

You may, in fact, have heard the term potash. This usually refers to salts that contain potassium in a water-soluble form. Potash was first made by taking plant ashes and soaking them in water in a pot, hence, “pot ash”. And, guess where we get the word potassium from? Yep. The pure element, being very reactive, wasn’t discovered until 1870, thousands of years after people first discovered how useful its compounds could be. And, AND, why does the element potassium have the symbol K? It comes from kali, the root of the word alkali.

See what I mean about connections?

butyl ethanoate butyl ethanoate

Why is the fact that the ashes are alkaline relevant? Well, to answer that we need to think about fats. Chemically, fats are esters. Esters are chains of hydrogen and carbon that have, somewhere within them, a cheeky pair of oxygen atoms. Like this (oxygen atoms are shown red):

Now, this is a picture of butyl ethanoate (aka butyl acetate – smells of apples, by the way) and is a short-ish example of an ester. Fats generally contain much longer chains, and there are three of those chains, and the oxygen bit is stuck to a glycerol backbone.

Thus, the thick, oily, greasy stuff that you think of as fat is a triglyceride: an ester made up of three fatty acid molecules and glycerol (aka glycerine, yup, same stuff in baking). But it’s the ester bit we want to focus on for now, because esters react with alkalis (and acids, for that matter) in a process called hydrolysis.

Fats are esters. Three fatty acid chains are attached to a glycerol “backbone”.

The clue here is in the name – “hydro” suggesting water – because what happens is that the ester splits where those (red) oxygens are. On one side of that split, the COO group of atoms gains a metal ion (or a hydrogen, if the reaction was carried out under acidic conditions), while the other chunk of the molecule ends up with an OH on the end. We now have a carboxylate salt (or a carboxylic acid) and an alcohol. Effectively, we’ve split the molecule into two pieces and tidied up the ends with atoms from water.

Still with me? This is where it gets clever. Having mixed our fat with alkali and split our fat molecules up, we have two things: fatty acid salts (hydrocarbon chains with, e.g. COONa+ on the end) and glycerol. Glycerol is extremely useful stuff (and, funnily enough, antiviral) but we’ll put that aside for the moment, because it’s the other part that’s really interesting.

What we’ve done here is produce a molecule that has a polar end (the charged bit, e.g. COONa+) and a non-polar end (the long chain of Cs and Hs). Here’s the thing: polar substances tend to only mix with other polar substances, while non-polar substances only mix with other non-polar substances.

You may be thinking this is getting technical, but honestly, it’s not. I guarantee you’ve experienced this: think, for example, what happens if you make a salad dressing with oil and vinegar (which is mostly water). The non-polar oil floats on top of the polar water and the two won’t stay mixed. Even if you give them a really good shake, they separate out after a few minutes.

The dark blue oily layer in this makeup remover doesn’t mix with the watery colourless layer.

There are even toiletries based around this principle. This is an eye and lip makeup remover designed to remove water-resistant mascara and long-stay lipstick. It has an oily layer and a water-based layer. To use it, you give the container a good shake and use it immediately. The oil in the mixture removes any oil-based makeup, while the water part removes anything water-based. If you leave the bottle for a minute or two, it settles back into two layers.

But when we broke up our fat molecules, we formed a molecule which can combine with both types of substance. One end will mix with oily substances, and the other end mixes with water. Imagine it as a sort of bridge, joining two things that otherwise would never be connected (see, literal connections!)

There are a few different names for this type of molecule. When we’re talking about food, we usually use “emulsifier” – a term you’ll have seen on food ingredients lists. The best-known example is probably lecithin, which is found in egg yolks. Lecithin is the reason mayonnaise is the way it is – it allows oil and water to combine to give a nice, creamy product that stays mixed, even if it’s left on a shelf for months.

When we’re talking about soaps and detergents, we call these joiny-up molecules “surfactants“. You’re less likely to have seen that exact term on cosmetic ingredients lists, but you will (if you’ve looked) almost certainly have seen one of the most common examples, which is sodium laureth sulfate (or sodium lauryl sulfate), because it turns up everywhere: in liquid soap, bubble bath, shampoo and even toothpaste.

I won’t get into the chemical makeup of sodium laureth sulfate, as it’s a bit different. I’m going to stick to good old soap bars. A common surfactant molecule that you’ll find in those is sodium stearate, which is just like the examples I was talking about earlier: a long hydrocarbon chain with COONa+ stuck on the end. The hydrocarbon end, or “tail”, is hydrophobic (“water-hating”), and only mixes with oily substances. The COONa+ end, or “head”, is hydrophilic (“water loving”) and only mixes with watery substances.

Bars of soap contain sodium stearate.

This is perfect because dirt is usually oily, or is trapped in oil. Soap allows that oil to mix with the water you’re using to wash, so that both the oil, and anything else it might be harbouring, can be washed away.

Which brings us back to the wretched virus. Sars-CoV-2 has a lipid bilayer, that is, a membrane made of two layers of lipid (fatty) molecules. Virus particles stick to our skin and, because of that membrane, water alone does a really bad job of removing them. However, the water-hating tail ends of surfacant molecules are attracted to the virus’s outer fatty surface, while the water-loving head ends are attracted to the water that’s, say, falling out of your tap. Basically, soap causes the virus’s membrane to dissolve, and it falls apart and is destroyed. Victory is ours – hurrah!

Hand sanitisers also destroy viruses. Check out this excellent Compound Interest graphic (click the image for more).

Who knew a nearly-5000 year-old weapon would be effective against such a modern scourge? (Well, yes, virologists, obviously.) The more modern alcohol hand gels do much the same thing, but not quite as effectively – if you have access to soap and water, use them!

Of course, all this only works if you wash your hands thoroughly. I highly recommend watching this video, which uses black ink to demonstrate what needs to happen with the soap. I thought I was washing my hands properly until I watched it, and now I’m actually washing my hands properly.

You may be thinking at this point (if you’ve made it this far), “hang on, if the ancient Babylonians were making soap nearly 5000 years ago, it must be quite easy to make… ooh, could I make soap?!” And yes, yes it is and yes you can. Believe me, if the apocolypse comes I shall be doing just that. People rarely think about soap in disaster movies, which is a problem, because without a bit of basic hygine it won’t be long before the hero is either puking his guts up or dying from a minor wound infection.

Here’s the thing though, it’s potentially dangerous to make soap, because most of the recipes you’ll find (I won’t link to any, but a quick YouTube search will turn up several – try looking for “saponification“) involve lye. Lye is actually a broad term that covers a couple of different chemicals, but most of the time when people say lye these days, they mean pure sodium hydroxide.

Pure sodium hydroxide is usually supplied as pellets.

Pure sodium hydroxide comes in the form of pellets. It’s dangerous for two reasons. Firstly, precisely because it’s so good at breaking down fats and proteins, i.e. the stuff that humans are made of, it’s really, really corrosive and will give you an extremely nasty burn. Remember that scene in the movie Fight Club? Yes, that scene? Well, that. (Follow that link with extreme caution.)

And secondly, when sodium hydroxide pellets are mixed with water, the solution gets really, really hot.

It doesn’t take a lot of imagination to realise that a really hot, highly corrosive, solution is potentially a huge disaster waiting to happen. So, and I cannot stress this enough, DO NOT attempt to make your own soap unless you have done a lot of research AND you have ALL the appropriate safety equipment, especially good eye protection.

And there we are. Soap is ancient and awesome, and full of interesting chemistry. Make sure you appreciate it every time you wash your hands, which ought to be frequently!

Stay safe, everyone. Take care, and look after yourselves.


Want something non-sciency to distract you? Why not check out my fiction blog: the fiction phial. There are loads of short stories, and even (recently) a poem. Enjoy!

If you’re studying from home, have you got your Pocket Chemist yet? Why not grab one? It’s a hugely useful tool, and by buying one you’ll be supporting this site – it’s win-win!

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Are you ok? You look a little flushed.

PrintYesterday was World Toilet Day (yes, really). This is actually an admirable campaign by WaterAid to raise awareness of the fact that one in three people around the world don’t have access to a safe and private toilet. This, of course, leads to unsanitary conditions which results in the spread of infection and disease. You’ve probably never given it a second thought, but loos literally save lives.

portaloo

Has the TARDIS’ replicator function gone funny?

So, with the topic of toilets in mind, I started thinking about chemical loos. If you live in the UK, the name Portaloo ® will probably spring to mind. This has practically become a generic word for a portable toilet, but it is (like Hoover, Sellotape and others) actually a brand name. I’m told that in America they call them porta-pottys or honey-buckets, which I rather like. In any case, all the chemicals and plastic make them seem like modern inventions, surely?

Actually, not at all. The idea of a self-contained, moveable toilet that you can pick up and take from place to place may be newer, but people have been using chemical toilets for hundreds of years. For example after, ahem, ‘business’ had been completed in an an old-fashioned wooden outhouse – basically a tall box built over a hole in the ground – the user would sprinkle a little lye or lime down the hole to help with the smell.

SodiumHydroxide

Don’t get sodium hydroxide on the toilet seat.

Both of these are strongly basic chemicals. Lye is either sodium hydroxide or potassium hydroxide, and lime is calcium oxide. Both mix with water to form extremely corrosive, alkaline solutions and, incidentally, give out a lot of heat in the process. Both are very damaging to skin. These were the days before health and safety; whatever you did, you had to try not to spill it on the seat.

Urea, a key chemical in urine, reacts with strong alkalis in a process known as alkaline hydrolysis. This produces ammonia, which is pretty stinky (if rather tough on the lungs), so if nothing else that helped to cover up other smells. Ammonia also kills some types of bacteria (which is one reason it’s popular in cleaning products). Flies generally don’t like high concentrations of it either, so that’s another plus.

Alkalis also have another effect in that decomposition of human waste is pH dependent; it works better in acidic conditions. Adding lye or lime raises the pH and slows down this decomposition. On top of this (literally) both lime and lye are hygroscopic: they absorb water. This keeps moisture down and allows a solid ‘crust’ to form on the surface of the waste, making it difficult for any volatile, smelly chemicals to escape. Lovely.

Bleach and ammonia could result in a rocket up your...

Bleach and ammonia could result in a rocket up your…

One word of caution: it’s very, very important you don’t try to clean such an outhouse with any kind of bleach. Bleach, which contains sodium hypochlorite, reacts with ammonia to form hydrogen chloride, chlorine gas and chloramine. None of which are good for your health. Even more dramatically (if this is more dramatic than death – you decide) if there’s lots of ammonia you might get liquid hydrazine, which is used in rocket fuels because it’s explosive. Who knew that toilet chemistry could also be rocket science?

But you don’t find buckets of lye in modern chemical toilets (although, apparently, there are still some people out there using it). So what’s in there? At one time, formaldehyde, otherwise known as methanal, was common. You probably recognise it as embalming fluid; the stuff that Damien Hirst floated that shark in. It’s an extremely effective preservative. Firstly, it kills most bacteria and fungi and destroys viruses, and secondly it causes primary amino groups in proteins to cross-link with other nearby nitrogen atoms, denaturing the proteins and preventing them from breaking down.

shark

Don’t worry, this won’t appear in your chemical toilet.

Interestingly, whilst definitely toxic in high concentrations, formaldehyde is a naturally-occuring chemical. It’s found in the bloodstream of animals, including humans, because it’s involved in normal metabolism. It also appears in fruits and vegetables, notably pears, grapes and shiitake mushrooms. The dose, as they say, makes the poison. I mention this because there are certain campaigners out there who insist it must be completely eliminated from everything, something which is entirely unecessary not to mention probably impossible (just for the hell of it, I’m also going to point out here that an average pear contains considerably more formaldehyde than a dose of vaccine).

All that said, because formaldehyde is extremely toxic in high concentrations, and because it can interfere with the breakdown processes in sewage plants (because it destroys bacteria), formaldehyde isn’t used in toilets so much anymore. In fact, many of the mixtures on sale are explicitly labelled “formaldehyde-free”. Modern formulations are enzyme-based and break down waste by biological activity. They are usually still dyed blue (if you work your way though the colour spectrum, it’s probably the least offensive colour), but usually using food-grade dye. As a result, what’s left afterwards is classed as sewage rather than chemical waste, making it easier to deal with.

Toilet twinning So, this has been brief tour around the fascinating world of toilet chemistry. You’d never have guessed there was so much to it, would you? Now, have you considered twinning your toilet?

Basic Chemistry

basic

The other end of the pH scale.

When you start writing a blog it’s hard to predict what people will find most interesting. Inevitably, it’s not what you expected. For example, two of The Chronicle Flask’s most-read posts are about rhubarb and lemons. Perhaps people are more interested in fruit than I ever imagined. Or perhaps I’m getting a lot of hits from people mistakenly looking for recipes.

Or maybe it’s because both feature the ever-interesting topic of acids. In which case, I should probably write something else about acids.

So, this is a post about bases.

Just in case this spectacular bit of contrariness isn’t immediately obvious, bases – some of which are called alkalis (I’m coming to that in a minute) – are at the other end of the pH scale to acids. Acids are the things with a pH value of less than 7, and bases have pH values of more than 7. So basically (hoho), they’re the opposites of acids.

whysoblueI’m using the word base deliberately, and not just because of all the brilliant chemistry puns you can make with it. The more familiar word is probably alkali, but while all alkalis are bases, not all bases are alkalis.

Alkalis are often described as soluble bases. More precisely, alkalis are produced from the metals in group 1 (the ‘alkali’ metals) and group 2 (the ‘alkaline earth’ metals) of the periodic table. The more general term, base, applies to anything that can neutralise an acid. Chemists have another definition: a base is a proton (H+ ion) acceptor, while acids are proton donors (actually chemists have yet another definition, but the proton acceptor one is the one that gets trotted out most often).

The distinction between alkalis and bases does matter to chemists and the two types of substance usually look quite different – bases tend to come in solid lumps or powders (baking soda, for example) and alkalis are more likely to arrive as a solution in a bottle – but in terms of chemistry they both get involved in the same type of chemical reaction, which is neutralising acids.

Indigestion tablet advertWe make use of this all the time, whether we realise it or not. For example if you’re suffering from acid indigestion you probably reach for the indigestion tablets. An advertising campaign for a particular brand of these says that they “turn excess acid into water and other natural substances”. Those ‘natural substances’ are salts – presumably it was decided that the word ‘salt’ had too many negative connotations (which is probably true: how many people would pop a pill that promised to turn into salt in their tummy?) The main ingredient in the tablets in question is calcium carbonate; a base that reacts with stomach acid to produce calcium chloride. Which is definitely a salt, if not the one most people think of when they hear the word.

Tangentially, calcium chloride is also a food additive with the E number E509. It falls into the category of anti-caking agents, which is sort of funny when you think about it.

Anyhoo, that’s one place you use a base (rhyming now as well as punning, sorry). You’re actually making one yourself every time you eat, because your liver produces a substance called bile (bloggers love bile) which helpfully neutralises the acid your stomach produces. If it didn’t, your intestines would get damaged by that acid, so it’s important stuff.

Interestingly, in a lot of the older medical traditions (you know, swallow three leeches with meals, turn around three times under a full moon and bury a toad under a horseradish in a mock turtle) the body’s health depended on the balance of four ‘humors’, or vital fluids: blood, phlegm, ‘yellow bile‘ (choler), and ‘black bile‘. If you had too much of the last two, it was supposed to cause aggression and depression, and in fact the Greek names for them are the root of the words cholera and melancholia.

It’s interesting that in the 21st century many people are obsessed with ‘alkalinizing‘ the body (just check out the comments on that lemons post) when for thousands of years people have understood that too much alkali is probably a bad thing. Public understanding of science has really moved on hasn’t it?

soapBile does something else that’s really quite important in the body, it helps you to digest fats. Bases are generally really good at breaking down fats. This is another thing that’s been known for quite a while, ever since soap was first discovered about (sources vary quite considerably on this) six thousand years ago. Soap is made by a process of saponification, in which fats react with a strong base, usually sodium hydroxide (otherwise known as caustic soda, or sometimes lye). This breaks apart the fat molecules to make glycerol and carboxylate salts (they’re the soap bit). Because of this use, sodium hydroxide features in a famous, and rather gruesome scene, in the film Fight Club.

firediamondNaOH

The fire diamond for NaOH

Because bases are so good at breaking down fats they’re actually surprisingly (or not, if you’ve just watched that Fight Club clip)dangerous, especially because they’re also quite good at breaking down proteins. Your skin is mostly fat and protein, so they can do quite a bit of damage. Remember fire diamonds? The one for sodium hydroxide has a 3 in the blue box, which means that short exposure could cause ‘serious temporary’ or ‘moderate residual’ injury – yikes.

Corrosive hazard symbol

Corrosive hazard symbol

The European hazard symbol is even more alarming, featuring a hand with holes being burned through it. Of course, acids have symbols like these too, but people sort of expect acids to do this kind of stuff. Whereas they’re often (unless they’re chemists) strangely unaware of the dangers of alkalis. For example there’s the a famous, and gruesome, story of the serial killer John George Haigh, who famously dissolved the bodies of his victims in oil drums full of concentrated sulfuric acid. It worked quite well, but he was caught eventually when the police searched his workshop and found sludge containing three human gallstones and part of a denture.

Sulfuric acid is a particularly powerful acid, and is undoubtedly incredibly dangerous stuff, but sodium hydroxide is not much safer. It will cause instantaneous and serious burns, and solid sodium hydroxide gets incredibly hot if it’s added to water. In fact, the water will quickly boil if you’re not careful.

In May last year American Carmen Blandin Tarleton was in the news because she had just received a face transplant. She needed it because her estranged husband had doused her with concentrated sodium hydroxide six years previously. She had undergone fifty-five operations before she made the decision to get the transplant. The pictures are really quite horrific. I won’t reproduce one here; you can see the result of the attack if you follow the link above. Tarleton has also written a book about her experiences. She was left blind and horribly disfigured, with burns to 80% of her body. Doctors described it as “the most horrific injury a human being could suffer”. Sodium hydroxide is not nice stuff.

It’s surprisingly, shockingly, easy to buy sodium hydroxide. Because it’s used in soap-making, you can get it quite easily. It’s even available on Amazon. And of course it’s an ingredient in lots of drain cleaners available in supermarkets. When they say you should wear gloves to handle this stuff, it’s definitely not health and safety gone mad. You really should. Even I would (and I’m really bad about wearing gloves).

So spare a thought for bases. They’re just as interesting, and certainly no nicer or safer than their acidic cousins. In fact, they’re so good at breaking down fat and protein that they could arguably be more dangerous. And next time you’re cleaning out your oven, do remember to wear your gloves.