Confusing chemical names: why do some sound so similiar?

It’s the end of March as I write this and, here in the UK at least, things are starting to feel a little bit hopeful. We’ve passed the spring equinox and the clocks have just gone forward. Arguments about the rights and wrongs of that aside, it does mean daylight late into the day, which means more opportunities to get outside in the evenings. Plus, of course, COVID-19 vaccines are rolling out, with many adults having had at least their first dose.

Some COVID-19 vaccines contain polyethylene glycol (PEG), a safe substance found in toothpaste, laxatives and other products, according to Science magazine and health expertsAh, yes. Speaking of vaccines… a couple of weeks ago I spotted a rather strange item trending on Twitter. The headline was: “Some COVID-19 vaccines contain polyethylene glycol (PEG), a safe substance found in toothpaste, laxatives and other products, according to Science magazine and health experts.”

Apart from being a bit of mouthful, this seemed like the most non-headline ever. And also, isn’t it the kind of thing that might raise suspicions in a certain mind? In a, “yeah, and why do they feel the need to tell us that, huh” sort of way?

Why on earth did it even exist?

A little bit of detective work later (by which I mean me tweeting about it and other people kindly taking the time to enlighten me) and I had my answer. The COVID-19 sceptic Alex Berenson had tweeted that the vaccine(s) contained antifreeze. Several people had immediately responded to say that, no, none of the vaccine formulations contain antifreeze. Antifreeze is ethylene glycol, which is definitely not the same thing as polyethylene glycol.

I’m not going to go much further into the vaccine ingredients thing, because actual toxicologists weighed in on that, and there’s nothing I (not a toxicologist) can really add. But this did get me thinking about chemical names, how chemists name compounds, and why some chemical names seem terrifyingly long while others seem, well, a bit silly.

A lot of the chemical names that have been around for a long time are just… names. That is, given to substances for a mixture of reasons. They do usually have something to do with the chemical makeup of the thing in question, but it might be a bit tangential.

formic acid, HCOOH, was first extracted from ants

For example, formic acid, HCOOH, takes its name from the Latin word for ant, formica, because it was first isolated by, er, distilling ant bodies (sorry, myrmecologists). On the other hand limestone, CaCO3, quicklime, CaO, and limewater, a solution of Ca(OH)2, all get their names from the old English word lim, meaning “a sticky substance,” which is also connected to the Latin limus, from which we get the modern word slime — because lime (mostly CaO) is the sticky stuff used to make building mortar.

The trouble with this sort of system, though, is that it gets out of control. The number of organic compounds listed in the American Chemical Society‘s index is in excess of 30 million. On top of which, chemists have an annoying habit of making new ones. Much as some people might think forcing budding chemists to memorise hundreds of thousands of unrelated names is a jolly good idea, it’s simply not very practical (hehe).

It’s the French chemist, Auguste Laurent, who usually gets most of the credit for deciding that organic chemistry needed a system. He was a remarkable scientist who discovered and synthesised lots of organic compounds for the first time, but it was his proposal that organic molecules be named according to their functional groups that would change things for chemistry students for many generations to come.

Auguste Laurent (image source)

Back in 1760 or so, memorising the names of substances wasn’t that much of a chore. There were half a dozen acids, a mere eleven metallic substances, and about thirty salts which were widely known and studied. There were others, of course, but still, compared to today it was a tiny number. Even if they were all named after something to do with their nature, or the discoverer, or a typical property, it wasn’t that difficult to keep on top of things.

But over the next twenty years, things… exploded. Sometimes literally, since health and safety wasn’t really a thing then, but also figuratively, in terms of the number of compounds being reported. It was horribly confusing, there were lots of synonyms, and the situation really wasn’t satisfactory. How can you replicate another scientist’s experiment if you’re not even completely sure of their starting materials?

In 1787 another French chemist, Guyton de Morveau, suggested the first general nomenclature — mostly for acids, bases and salts — with a few simple principles:

  • each substance should have a unique name, as short and specific as possible
  • the name should reflect what the substance consisted of, that is, describe its “composing parts”
  • unknown substances should be assigned names with no particular meaning, being sure not to suggest something false about the substance (if you know it’s not an acid, for example, don’t name it someinterestingname acid)
  • new names should be based on old languages, such as Latin

His ideas were accepted and adopted by most chemists at the time, although a few did attack them, claiming they were “barbarian, incomprehensible, and without etymology” (reminds me of some of the arguments I’ve had about sulfur). Still, his classification was eventually made official, after he presented it to the Académie des Sciences.

Chemists needed a naming system that would allow them to quickly identify chemical compounds.

However, by the middle of the 1800s, the number of organic compounds — that is, ones containing carbon and hydrogen — was growing very fast, and it was becoming a serious problem. Different methods were proposed to sort through the messy, and somewhat arbitrary, accumulation of names.

Enter Auguste Laurent. His idea was simple: name your substance based on the longest chain of carbon atoms it contains. As he said, “all chemical combinations derive from a hydrocarbon.” There was a bit more to it, and he had proposals for dealing with specific substances such as amines and aldehydes, and of course it was in French, but that was the fundamental idea.

It caused trouble, as good ideas so often do. Most of the other chemists of the time felt that chemical names should derive from the substance’s origins. Indeed, some of the common ones that chemistry professors are clinging onto today still do. For example, the Latin for vinegar is acetum, from which we get acetic acid. But, since organic chemistry was increasingly about making stuff, it didn’t entirely make sense to name compounds after things they might have come from, if they’d come from nature — even when they hadn’t.

So, today, we have a system that’s based on Laurent’s ideas, as well as work by Jean-Baptiste Dumas and, importantly, the concept of homology — which came from Charles Gerhardt.

Homology means putting organic compounds into “families”. For example, the simplest family is the alkanes, and the first few are named like this:

Like human families, chemical families share parts of their names and certain characteristics.

The thing to notice here is that all the family members have the same last name, or rather, their names all end with the same thing: “ane”. That’s what tells us they’re alkanes (they used to be called paraffins, but that’s a name with other meanings — see why we needed a system?).

So the end of the name tells us the family, and the first part of the name tells us about the number of carbons: something with one carbon in it starts with “meth”. Something with five starts with “pent”, and so on. We can go on and on to much bigger numbers, too. It’s a bit like naming your kids by their birth order, not that anyone would do such a thing.

There are lots of chemical families. The alcohols all end in “ol”. Carboxylic acids all end in “oic acid” and ketones end in “one” (as in bone, not the number). These endings tell us about certain groups of atoms the molecules all contain — a bit like everyone in a family having the same colour eyes, or the same shaped nose.

A chemist that’s learned the system can look at a name like this and tell you, just from the words, exactly which atoms are present, how many there are of each, and how they’re joined together. Which, when you think about it, is actually pretty awesome.

Which brings me back to the start and the confusion of glycols. Ah, you may be thinking, so ethylene glycol and polyethylene glycol are part of the same family? Their names end with the same thing, but they start differently?

Well, hah, yes and no. You remember a moment ago when I said that there are still some “common” names in use, that came from origins — for example acetic acid (properly named ethanoic acid)? Well, these substances are a bit like that. The ending “glycol” originates from “glycerine” because the first ones came from, yes, glycerine — which you get when fats are broken down.

Polyethylene glycol (PEG) is a polymer, with very different properties to ethylene glycol (image source)

Things that end in glycol are actually diols, that is, molecules which contain two -OH groups of atoms (“di” meaning two, “ol” indicating alcohol). Ethylene glycol is systematically named ethane-1,2-diol, from which a chemist would deduce that it contains two carbon atoms (“eth”) with alcohol groups (“ol”) on different carbons (1,2).

Polyethylene glycol, on the other hand, is named poly(ethylene oxide) by the International Union of Pure and Applied Chemistry (IUPAC), who get the final say on these things. The “poly” tells us it’s a polymer — that is, a very long molecule made by joining up lots and lots of smaller ones. In theory, the “ethylene oxide” bit tells us what those smaller molecules were, before they all got connected up to make some new stuff.

Okay, fine. So what’s ethylene oxide? Well, you see, that’s not quite a systematic name, either. Ethylene oxide is a triangular-shaped molecule with an oxygen atom in it, systematically named oxirane. Why poly(ethylene oxide), and not poly(oxirane), then? Mainly, as far as I can work out, to avoid confusion with epoxy resins and… look, I think we’ve gone far enough into labyrinth at this point.

The thing is, polyethylene glycol is usually made from ethylene glycol. Since everyone tends to call ethylene glycol that (and rarely, if ever, ethane-1,2-diol), it makes sense to call the polymer polyethylene glycol. Ethylene glycol makes polyethylene glycol. Simple.

Plastic bags are made from polythene, which has very different properties to the ethene that’s used to make it.

Polymers are very different to the molecules they’re made from. Of course they are, otherwise why bother? For example, ethene (also called ethylene, look, I’m sorry) is a colourless, flammable gas at room temperature. Poly(ethylene) — often just called polythene — is used to make umpteen things, including plastic bags. They’re verrrrry different. A flammable gas wouldn’t be much use for keeping the rain off your broccoli and sourdough.

Likewise, ethylene glycol is a colourless, sweet-tasting, thick liquid at room temperature. It’s an ingredient in some antifreeze products, and is, yes, toxic if swallowed — damaging to the heart, kidneys and central nervous system and potentially fatal in high enough doses. Polyethylene glycol, or PEG, on the other hand, is a solid or a liquid (depending on how many smaller molecules were joined together) that’s essentially biologically inert. It passes straight through the body, barely stopping along the way. In fact, it’s even used as a laxative.

So the headlines were accurate: PEG is “a safe substance found in toothpaste, laxatives and other products.” It is non-toxic, and describing it as “antifreeze” is utterly ridiculous.

In summary: different chemicals, in theory, have nice, logical, tell-you-everything about them names. But, a bit like humans, some of them have obscure nicknames that bear little resemblance to their “real” names. They will insist on going by those names, though, so we just need to get on with it.

The one light in this confusingly dark tunnel is the internet. In my day (croak) you had to memorise non-systematic chemical names because, unless you had a copy of the weighty rubber handbook within reach, there was no easy way to look them up. These days you can type a name into Google (apparently other search engines are available) and, in under a second, all the names that chemical has ever been called will be presented to you. And its chemical formula. And multiple other useful bits of information. It’s even possible to search by chemical structure these days. Kids don’t know they’re born, I tell you.

Anyway, don’t be scared of chemical names. They’re just names. Check what things actually are. And never, ever listen to Alex Berenson.

And get your vaccine!


If you’re studying chemistry, 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! If you happen to know a chemist, it would make a brilliant stocking-filler! As would a set of chemistry word magnets!

Like the Chronicle Flask’s Facebook page for regular updates, or follow @chronicleflask on Twitter. Content is © Kat Day 2021. You may share or link to anything here, but you must reference this site if you do. If you enjoy reading my blog, and especially if you’re using information you’ve found here to write a piece for which you will be paid, please consider buying me a coffee through Ko-fi using the button below.
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Want something non-sciency to distract you from, well, everything? Why not check out my fiction blog: the fiction phial.

 

Easy Indicators

Indicator rainbow, reproduced with kind permission of Isobel Everest, @CrocodileChemi1

Recently on Twitter CrocodileChemist (aka Isobel Everest), a senior school science technician (shout out to science technicians, you’re all amazing) shared a fabulous video and photo of a “pH rainbow”.

The effect was achieved by combining various substances with different pH indicators, that is, substances that change colour when mixed with acids or alkalis.

Now, this is completely awesome, but, not something most people could easily reproduce at home, on account of their not having methyl orange or bromothymol blue, or a few other things (that said, if you did want to try, Isobel’s full method, and other indicator art, can be found here).

But fear not, I’ve got this. Well, I’ve got a really, really simple version. Well, actually, I’ve got more of an experiment, but you could make it into more of a rainbow if you wanted. Anyway…

This is what you need:

  • some red cabbage (one leaf is enough)
  • boiling water
  • mug
  • white plate, or laminated piece of white card, or white paper in a punched pocket
  • cling film/clear plastic wrap (if you’re using a plate)
  • mixture of household substances (see below)
  • board marker (optional) or pen
  • plastic pipettes (optional, but do make it easier – easily bought online)

First, make the indicator. There are recipes online, but some of them are over-complicated. All you really need to do is finely chop the red cabbage leaf, put it in a mug, and pour boiling water over it. Leave it to steep and cool down. Don’t accidentally drink it thinking it’s your coffee. Pour off the liquid. Done.

If you use a plate, cover it with cling film

Next, if you’re using a plate, cover it with cling film. There are two reasons for this: firstly, cling film is more hydrophobic (water-repelling) than most well-washed ceramic plates, so you’ll get better droplets. Secondly, if you write on a china plate with a board marker it doesn’t always wash off. Ask me how I know.

Next step: hunt down some household chemicals. I managed to track down oven cleaner, plughole sanitiser, washing up liquid, lemon juice, vinegar, limescale remover and toilet cleaner (note: not bleach – don’t confuse these two substances, one is acid, one is alkali, and they must never be mixed).

Label your plate/laminated card/paper in punched pocket with the names of the household substances.

Place a drop of cabbage indicator by each label. Keep them well spaced so they don’t run into each other. Also, at this stage, keep them fairly small. Leave one alone as a ‘control’. On my plate, it’s in the middle.

Add a drop of each of your household substances and observe the colours!

Red cabbage indicator with various household substances

IMPORTANT SAFETY NOTE: some of these substances are corrosive. The risk is small because you’re only using drops, but if working with children, make sure an adult keeps control of the bottles, and they only have access to a tiny amount. Drip the more caustic substances yourself. Take the opportunity to point out and explain hazard warning labels. Use the same precautions you would use when handling the substance normally, i.e. if you’d usually wear gloves to pick up the bottle, wear gloves. Some of these substances absolutely must not be mixed with each other: keep them all separate.

Here’s a quick summary of what I used:

A useful point to make here is that pH depends on the concentration of hydrogen ions (H+) in the solution. The more hydrogen ions, the more acidic the solution is. In fact, pH is a log scale, which means a change of x10 in hydrogen concentration corresponds to a change of one pH point. In short, the pH of a substance changes with dilution.

Compound Interest’s Cabbage Indicator page (click image for more info)

Which means that if you add enough water to acid, the pH goes up. So, for example, although the pH of pure ethanoic acid is more like 2.4, a dilute vinegar solution is probably closer to 3, or even a bit higher.

Compound Interest, as is usually the case, has a lovely graphic featuring red cabbage indicator. You can see that the colours correspond fairly well, although it does look like my oven cleaner is less alkaline (closer to green) than the plughole sanitiser (closer to yellow).

As the Compound Interest graphic mentions, the colour changes are due to anthocyanin pigments. These are red/blue/purple pigments that occur naturally in plants, and give them a few advantages, one of which is to act as a visual ripeness indicator. For example, the riper a blackberry is, the darker it becomes. That makes it stand out against green foliage, so it’s easier for birds and animals to find it, eat it and go on to spread the seeds. Note that “unripe” colours, yellow-green, are at the alkaline end, which corresponds to bitter flavours. “Ripe” colours, purple-red, are neutral to acidic, corresponding with much more appealing sweet and tart flavours. Isn’t nature clever?

You can make a whole mug full of indicator from a single cabbage leaf (don’t drink it by mistake).

Which brings me to my final point – what if you can’t get red cabbage? Supermarkets are bit… tricky at the moment, after all. Well, try with some other things! Any dark-coloured plant/fruit should work. Blueberries are good (and easy to find frozen). The skins of black grapes or the very dark red bit of a rhubarb stalk are worth a try. Blackberries grow wild in lots of places later in the year. Tomatoes, strawberries and other red fruits will also give colour changes (I’ve talked about strawberries before), although they’re less dramatic.

For those (rightly) concerned about wasting food – you don’t need a lot. I made a whole mug full of cabbage indicator from a single cabbage leaf, and it was the manky brown-around-the-edges one on the outside that was probably destined for compost anyway.

So, off you go, have fun! Stay indoors, learn about indicators, and stay safe.

EDIT: after I posted this, a few people tried some more experiments with fruits, vegetables and plants! Beaulieu Biology posted the amazing grid below, which includes everything from turmeric to radishes:

Image reproduced with kind permission of Beaulieu Biology (click for larger version)

And Compound Interest took some beautiful photos of indicator solutions extracted from a tulip flower, while CrocodileChemist did something similar and used the solutions to make a gorgeous picture of a tree. Check them out!


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!

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 couple of poems. Enjoy!

Like the Chronicle Flask’s Facebook page for regular updates, or follow @chronicleflask on Twitter. Content is © Kat Day 2020. You may share or link to anything here, but you must reference this site if you do. If you enjoy reading my blog, please consider buying me a coffee through Ko-fi using the button below.
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Let’s change the way we talk about changes

It’s nearly the end of the school year here in the U.K., traditionally a time for reflecting on what’s gone before and planning ahead for the shiny, new September coming in a mere nine weeks (sorry, teachers!). With that in mind, let’s talk about something that comes up early in most chemistry syllabuses, and which bothers me a little more each time I think about it.

Chemical reactions occur when a match burns.

It’s the concept of chemical and physical changes. For those who aren’t familiar, this is the idea that changes we observe happening to matter fall into two, broad categories: chemical changes, where new substances are made, and physical changes, where no new substances are made.

Examples of chemical changes include things like burning a match, cooking an egg, or the reaction between vinegar and baking soda. Physical changes are largely changes of state, such as melting and boiling, but also include changes such as dissolving salt in water, or grinding limestone chips to powder.

So far, so good. Except… then we start to put descriptors on these things. And that’s when the trouble starts.

multiple choice exam questionThe first problem comes with the idea that “chemical changes are irreversible.” This is often taught in early secondary science as a straight-up fact, and is so pervasive that it’s even appeared in multiple choice exam questions, like the one shown here. The student, for the record, was expected to choose option C, “the change is irreversible.”

Except. Argh. I can tell you exactly why the student has opted for D, “the change is reversible,” and it’s not because they haven’t done their revision. Quite the opposite, in fact. No, it’s because this student has learned about weak acids. And in learning about acids, this student met this symbol, ⇌, which literally indicates a reversible chemical reaction.

Yes, that’s right. Not too long after teaching students that chemical reactions are not reversible, we then explicitly teach them that they are. Indeed, this idea of chemical reversibility is such a common one, such an important concept in chemistry, that we even have a symbol for it.

Now, of course, I can explain this. When we say chemical reactions are irreversible, what we mean is “generally irreversible if they’re carried out in an open system.” In other words, when the wood in that match burns out in the open, the carbon dioxide and water vapour that form will escape to the atmosphere, never to return, and it’s impossible to recover the match to its original state.

The problem is that many chemical reactions occur in closed systems, not least a lot of reactions that happen in solution. Hence, the whole acids thing, where we talk about weak acids “partially dissociating” into ions.

Then there’s that entire topic on the Haber process…

Can I be the only one to think that this is rather a lot of nuance to expect teenagers to keep in their head? It’s nothing short of confusing. Should we really be saying one thing in one part of a course, and the literal opposite in another? To be clear, this isn’t even a GCSE vs. A level thing – these ideas appear in the same syllabus.

Melting is a change of state, in this case from (solid) ice to (liquid) water.

All right, okay, let’s move along to the idea that physical changes are reversible. That’s much more straightforward, isn’t it? If I melt some ice, I can re-freeze it again? If I boil some water, I can condense it back into the same volume of liquid… well… I can if I collect all vapour. If I do it in a closed system. The opposite of the condition we imposed on the chemical reactions. Er. Anyway…

We might just about get away with this, if it weren’t for the grinding bit. If physical changes are truly readily reversible, then we ought to be able to take that powder we made from the limestone lumps and make it back into a nice single piece again, right? Right?

See, this is the problem. What this is really all about is entropy, but that’s a fairly tricky concept and one that’s not coming up until A level chemistry.

Okay. Instead of talking about reversible and irreversible, let’s talk about bond-breaking and bond-forming. That’s fine, isn’t it? In chemical changes, bonds are broken and formed (yep) and in physical changes, they aren’t.

Except….

Let’s go back to water for a moment. Water has the formula H2O. It’s made up of molecules where one oxygen atom is chemically bonded to two hydrogen atoms. When we boil water, we don’t break any of those bonds. We don’t form hydrogen and oxygen gas when we boil water; making a hot cup of tea would be a lot more exciting if we did. So we can safely say that boiling water doesn’t involve breaking any bonds, right? We-ell…

Water molecules contain covalent bonds, but the molecules are also joined by (much weaker) hydrogen bonds.

The trouble is that water contains something called hydrogen bonds. We usually do a bit of a fudge here and describe these as “intermolecular forces,” that is, forces of attraction between molecules. This isn’t inaccurate. But the clue is in the name: hydrogen bonds are quite, well, bond-y.

When water boils, hydrogen bonds are disrupted. Although the bonds in individual H2O molecules aren’t broken, the hydrogen bonds are. Which means… bonds are broken. Sort of.

But we’re probably on safe ground if we talk about the formation of new substances. Aren’t we?

Except….

What about dissolving? If I dissolve hydrogen chloride gas, HCl, in water, that’s a physical change, right? I haven’t made anything new? Or… have I? I had molecules with a covalent bond between the hydrogen and the chlorine, and now I have… er… hydrochloric acid (note, that’s a completely different link to the one I used back there), made up of H+ and Cl- ions mingled with water molecules.

So… it’s…. a chemical change? But wait. We could (I don’t recommend it) evaporate all that water away, and we’d have gaseous HCl again. It’s reversible.

Solid iodine is silvery-grey, but iodine vapour is a brilliant violet colour.

Hm. What about the signs that a chemical change is occurring? Surely we’re all right there? Fizzing: that’s a sign of a chemical change. Except… are you sure you know the difference between boiling and fizzing? It’s basically all bubbles, after all. Vapour? But, steam is a vapour, isn’t it? Although, on the other hand, water is a product of several chemical reactions. Colour changes? Check out what happens when you heat a small amount of solid, silvery-grey iodine so that it sublimes (spoiler: there’s a colour change).

Is anyone else really confused by now?

You should be. Your students almost certainly are.

There are, in short, more exceptions to every single one of these rules that there are for that “i before e” thing you learned in English (a rule, incidently, which is particularly galling for scientists who constantly have to deal with weights and heights).

Where do we go from here? I think it’s probably time we asked ourselves why we’re even teaching this concept in the first place. Really, it’s there to get students to think about the difference between changes of state and chemical reactions.

I suspect we need to worry about this rather less than we are: most children are very good at identifying changes of state. They do it instinctively. They only start getting confused about it when we teach them a lot of rules which they then try to apply. I’m pretty sure that’s not the way teaching is supposed to work.

A complicated arrangement of chemical glassware

This could definitely be simpler.

If I had my way, I’d ditch the physical and chemical change labels altogether and, instead, just talk about changes of state and chemical reactions. There is precisely one differentiator between these two, and it is: have we made any new stuff? If the answer is no, it’s a change of state. If the answer is yes, then a chemical reaction has occurred. Job done. (And yes, this would squarely define gaseous hydrogen chloride dissolving in water to form hydrochloric acid as a chemical reaction, and I have no problem at all with that.)

I say we change the way we talk about changes: chemistry has a reputation for being tricky, and this sort of confusing, contradictory thing is part of the reason why.


Like the Chronicle Flask’s Facebook page for regular updates, or follow @chronicleflask on Twitter. Content is © Kat Day 2019. You may share or link to anything here, but you must reference this site if you do. If you enjoy reading my blog, please consider buying me a coffee through Ko-fi using the button below.
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Buffers for bluffers

buffering

No, not that kind…

A little while ago now I wrote a post entitled Amazing Alkaline Lemons?. It’s been very popular, sort of. Well, it’s elicited an awful lot of comments anyway. Quite a few have mentioned buffers, which are jolly important things. They also seem to be somewhat misunderstood. So here we go, buffers 101:

Buffers regulate pH (remember that pH is the scale that measures how acidic, or basic, a solution is), and they’re essential in the body. Without them, your blood pH would fluctuate, and that that would be a very bad thing indeed. Outside a very narrow pH range (7.38 to 7.42, which is essentially neutral) proteins are denatured and enzymes stop working. In short, your body would quickly stop functioning in a really quite fatal way.

So what is a buffer? A buffer is actually a mixture, of a weak acid and its salt. Or, as chemists would say, its ‘conjugate base‘. (I’m deliberately avoiding the word ‘alkali’, because alkali has a specific meaning and it would be wrong to use it in this situation – I mention this because the word ‘alkalising’ has come up more than once).

The main buffer system in the blood is the bicarbonate buffering system. We need it because our blood has to transport carbon dioxide out of our bodies, and when carbon dioxide is dissolved in solution it forms an acid called carbonic acid. If this weren’t somehow controlled, our blood pH would quickly plummet and, as I’ve already mentioned, we’d die. This would obviously be something of an evolutionary dead-end.

Chemistry to the rescue! Carbonic acid (H2CO3) forms, but it also breaks apart again to form hydrogen ions (H+) and bicarbonate ions (HCO3) producing something chemists call an equilibrium (symbolised by the funny two-way arrow you can see below).

H2CO3 ⇌ H+ + HCO3

Equilibria have a way of balancing themselves out, and this is key to how buffers work. If you add some extra hydrogen ions to a buffer system the equilibrium shifts to absorb those hydrogen ions, keeping the pH constant. Likewise, if an alkali (or base) is added, it goes the other way and actually causes more hydrogen ions to be released. This is remarkably difficult to budge, unless you swamp it with a really strong acid (or base).

As a result, your blood pH stays perfectly balanced, and a good thing too. And all you need for it to work is to breathe. I recommend that if you want to stay healthy you don’t stop doing that.

There are other important buffer systems in the body. One that gets mentioned quite a lot is the phosphate buffer system. This plays a relatively minor role in controlling blood pH, but it is pretty important for your cells. This buffer is made up of dihydrogen phosphate ions and hydrogen phosphate ions. Phosphate plays an important role in bone health, not to mention your body’s ability to use energy effectively. Fortunately, unless you have some kind of fairly serious health problem your kidneys do a cracking job of controlling phosphate levels, so there’s no need to worry too much about it, beyond aiming, as we all should, for a generally healthy diet.

So there we are. Buffers are a mixture, they form naturally in the body, you don’t really need to do anything to help them along, and they quietly keep you alive. Pretty cool bit of everyday chemistry really.


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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.