Tag Archives: glycerol

Onerous ovens: why is cleaning the cooker such a chore?

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As I write Thanksgiving was a few days ago, when most Americans traditionally cook a very large meal based around roasted turkey. Most Brits – and other countries of course – have the same thing coming up soon in the form of Christmas, and there are lots of other celebrations around this time of year that seem to feature cooking and food quite heavily.

Whatever your traditions, then, it’s a time when many of us frown critically at the dark, sticky depths of our oven and wonder if, perhaps, we should attempt to give it a clean. Or at least pay someone else to come and clean it.

Why is oven cleaning such a difficult and unpleasant job, anyway? It’s not that hard to clean other surfaces, is it? Why are ovens so particularly awful?

Well, to explain this, we first need to understand fats.

Fats vaporise during cooking.

Most of the grime in your oven is fat, combined with the carbonised remains of… something or other. The sorts of fats that are common in animal and plant products have boiling points around the 300 oC mark (animal fats typically having higher values than plant oils), but they start to form vapours at much lower temperatures, and certainly at typical cooking temperatures there’s plenty vaporised oil around. Besides, under typical conditions most oils will “smoke” – i.e. start to burn – long before they get close to boiling.

We’re all familiar with the idea that fats don’t mix well with water, and herein lies the problem: all that fatty gloop that’s stuck to the inside of your oven just doesn’t want to come off with standard cleaning methods, particularly when it’s built up over time.

Can chemistry help us here? What are fats, chemically? Well, they’re esters. Which may or may not mean anything to you, depending on how much chemistry you can remember from school. But even if you don’t remember the name, trust me, you know the smell. In particular, nail polishes and nail polish removers contain the simple ester known as ethyl acetate, otherwise known as ethyl ethanoate. (Some people say this chemical smells like pear drops which… only really helps if you know what pear drops smell like. Look, it smells of nail polish, okay?)

Fats are esters (image source)

Anyway, the point is that esters have a particular sequence of atoms that has a carbon bonded to an oxygen, which is bonded to another carbon, which is in turn double-bonded to oxygen. This is a bit of a mouthful, so chemists often write it as COOC. In the diagram here, oxygen atoms are red while carbon atoms are black.

There are actually three ester groups in fat molecules – which explains why fats are also known as triglycerides.

In terms of general chemistry, esters form when a carboxylic acid (a molecule which contains a COOH group) reacts with an alcohol (a molecule that contains an OH group). And this is where it all starts to come together – honest – because you’ve probably heard of fatty acids, right? If nothing else, the words turn up in certain food additive names, in particular E471 mono- and diglycerides of fatty acids, which is really common in lots of foods, from ice cream to bread rolls.

Glycerol is a polyol — a molecule that contains several alcohol groups (image source)

Well, this reaction is reversible, and as a result fats (which are esters, remember) break up into fatty acids and glycerol – which is a polyol, that is, a molecule with several alcohol groups. Or, to look at it the other way around: fats are made by combining fatty acids with glycerol.

And the reason it’s useful to understand all this is that the way you break up esters, and therefore fat, is with alkalis. (Well, you can do it with acid, too, but let’s not worry about that for now.)

Strong alkalis break up fats in a chemical reaction called hydrolysis — the word comes from the Greek for water (hydro) and unbind (lysis) and so literally means “split up with water”. Humans have known about this particular bit of chemistry for a long time, because it’s fundamental to making soap. As I said a few months ago when I was banging on about hand-washing, the ancient Babylonians were making soap some 4800 years ago, by boiling fats with ashes – which works because alkaline compounds of calcium and potassium form when wood is burnt at high temperatures.

The grime in ovens is mostly fat.

The really clever thing about all this is that two things are happening when we mix alkali with fat: not only are we breaking up the fat molecules, but also the substances they break up into are water-soluble (whereas fats, as I said at the start, aren’t). Which makes them much easier to clean away with water. Obviously this is the very point of soap, but it’s also handy when trying to get all that baked-on gunk off your oven walls.

Now, in theory, this means you could get some lye (aka sodium hydroxide, probably), smear it all over your oven and voilà. But I don’t recommend it, for a few reasons. Firstly, it’s going to be difficult to apply, since sodium hydroxide is mostly sold as pellets or flakes (it’s pretty easy to buy, because people use it to make soap).

Sodium hydroxide, sometimes called lye, is often sold in the form of pellets.

But, you say, couldn’t I just dissolve it in water and spray or spread it on? Yes, yes you could. But it gets really, really hot when you mix it with water. So you need to be incredibly careful. Because, and this is my next point, chemically your skin is basically fat and protein, and this reaction we’re trying to do on oven sludge works equally well on your skin. Only, you know, more painfully, and with scarring and stuff. In short, if you’re handing lye, wear good nitrile on vinyl gloves and eye protection.

Actually, regardless of how you’re cleaning your oven you should wear gloves and eye protection, because the chemicals are still designed to break down fats and so… all of the above applies. It’s just that specially-designed oven cleaners tend to come with easier (and safer) ways to apply them. For example, they might come as a gel which you can paint on, and/or with bags that you can put the racks into, and may also be sold with gloves and arm protectors (but rarely goggles – get some separately). They might also have an extra surfactant, such as sodium laureth sulfate, added to help with breaking down grease. The main ingredient is still either potassium hydroxide or sodium hydroxide, though.

Well, possibly, but also not really, if you’re sensible.

As an aside, it makes me smile when I come across an article like this which talks about the “serious” chemicals in oven cleaners and more “natural” ways to clean your oven. The “natural” ways are invariably weak acids or alkalis such as lemon juice or baking soda, respectively. They’re essentially ineffective ways of trying to do exactly the same chemistry.

And okay, sure, the gel and the bag and so on in the modern kits are newer tech, but the strong alkali? Nothing more natural than that. As I said at the start, humans have literally been using it for thousands of years.

A point which really cannot be repeated enough: natural does not mean safe.

Fumes can be irritating to skin, eyes and lungs.

Speaking of which, you will get fumes during oven cleaning. Depending on the exact cleaning mixture involved, these will probably be an alkaline vapour, basically (haha) forming as everything gets hot. Such vapour is potentially irritating to skin, eyes and lungs, but not actually deadly toxic. Not that I recommend you stick your head in your freshly-scrubbed oven and inhale deeply, but you take my point. It might give food a soapy, possibly bitter (contrary to what’s stated in some text books, not all alkalis taste bitter, but do not experiment with this) taste if you really over-do it.

In short, if you’re cleaning your oven yourself: follow the manufacturer’s instructions, make sure your kitchen is well-ventilated, leave the oven door open for a while after you’ve finished and, to be really sure, give all the surfaces an extra wash down with plenty of water.

Put the cleaning off until January – after all, the oven’s only going to get dirty again.

And that’s… it, really. Whether you’re cleaning your own oven or getting someone else to do it for you, the chemistry involved is really, really old. And yes, the chemicals involved are hazardous, but not because they’re not “natural”. Quite the opposite.

Or you could just leave it. I mean, it’s only going to get dirty again when you cook Christmas dinner, right?

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!

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Do you really need to worry about baby wipes?

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Never mind ingredients, just give me a packet that's not empty!

Never mind ingredients, just give me a packet that’s not empty!

A little while back I wrote a post about shampoo ingredients, and in passing I mentioned baby wipes. Now, these are one of those products which you’ve probably never bought if you’re not a parent, but as soon as you are you find yourself increasingly interested in them. Yes, I know, reusable ‘wipes’ are a thing. But after dealing with a nappy explosion at 2am in the morning, I’m willing to bet that more than one parent’s environmental conscience has gone in the rubbish bin along with a bag of horror they never want to see again, at least for a little while.

But which wipes to buy? The cheapest ones? The nicest-smelling ones? The fragrance-free ones? The ones with the plastic dispenser on the top that allow you to easily grab one wipe at a time? Or not, because those bulky dispensers produce yet more plastic waste? Or just whichever brand you grabbed first at the all-night supermarket at some unpleasant hour that’s too late to be night yet too early to be morning?

All of the above at one time or another, probably. However, I’m going to suggest that one thing you can stop worrying about right now is whether or not your wipes are labelled ‘chemical-free’.

As I’ve explained before, everything is made up of chemicals. By any sensible definition, water is a chemical, and thus the claim that Water Wipes® (“the world’s purest baby wipe”) are “chemical free” is simply incorrect.

These wipes are not, actually, chemical-free.

These wipes are not, actually, chemical-free.

In fact, Water Wipes® aren’t even, as you might imagine, made of some sort of non-woven fabric impregnated with plain water. No, they contain something else: grapefruit seed extract.

Well, that sounds natural, I hear you say. It does, doesn’t it? Grapefruit, that sounds fresh. Seed, well seeds are healthy, aren’t they? And the word ‘extract’ is very natural-sounding. What’s the problem?

Let’s start with what grapefruit seed extract, also called GSE, actually is. It’s made from the seeds, pulp and white membranes of grapefruit. These ingredients are ground up and a drop of glycerin is added. Glycerin, by the way, is otherwise known as glycerol, or propane-1,2,3-triol. It’s naturally-occurring – it’s one of the molecules you get when you break up fats – and it’s usually made from plants such as soybeans or palm (uh oh…), or sometimes from tallow (oh dear…) or as a byproduct of the petroleum industry (yikes! – I wonder if the manufacturers of Water Wipes® enquired about the nature of the glycerin being added to their product…?)

But anyway, back to GSE. Like all plant extracts, grapefruit seed extract is stuffed full of other chemicals that occur naturally. In particular, flavonoids, ascorbic acid (vitamin C), tocopherols, citric acid, limonoids and sterols.

citric acid synthetic vs natural

Can you tell the difference?

So… in short, not chemical-free at all. Not even a bit. The problem here is that, in marketing, the term ‘chemical-free’ is used to mean something that only contains ingredients from ‘natural’ sources. But this is meaningless. Take citric acid, for example. (E330 by the way – E numbers don’t mean something’s deadly, either. In fact, quite the opposite.) There’s no difference between citric acid extracted from a grapefruit and citric acid prepared in a laboratory. They both have exactly the same atoms and the same molecular formula and structure. They both react in the same way.

They’d both be classified as corrosive in high concentrations, and irritant in low concentrations. This isn’t even “might” cause irritation. This is absolutely, definitely, positively WILL cause irritation.

Wait, hang on a minute! There’s a potentially corrosive chemical in the ‘chemical-free’ baby wipes, and unsuspecting parents are putting it on their baby’s skin?!

Yep.

But before anyone runs off to write the next Daily Mail headline, let’s be clear. It’s really not going to burn, alien acid-style, through a new baby’s skin. It’s not even going to slightly redden a baby’s skin, because the quantity is so miniscule that it quite literally has no corrosive properties at all. It’s the same logic as in the old adage that “the dose makes the poison“.

This is where we, as consumers, ought to stop and think. If a fraction of a drop of citric acid is harmless then…. perhaps that small quantity of PEG 40 hydrogenated castor oil or sodium benzoate in most (considerably less expensive, I’m just saying) other brands of baby wipes isn’t as awful as we thought, either…

Indeed, it’s not. But what sodium benzoate in particular IS, is a very effective preservative.

Grapefruit seed extract is marketed as a natural preservative, but studies haven't backed up this claim.

Grapefruit seed extract is allegedly a natural preservative, but studies haven’t backed up this claim.

Why does this matter? Well, without some sort of preservative baby wipes, which sit in a moist environment for weeks or months or even years, might start to grow mould and other nasties. You simply can’t risk selling packets of water-soaked fabric, at a premium price, without any preservative at all, because one day someone might open one of those packets and find it full of mould. At which point they would, naturally, take a photo and post it all over social media. Dis-as-ter.

This is why Water Wipes® include grapefruit seed extract, because it’s a natural preservative. Except…

When researchers studied GSE and its antimicrobial properties they found that most of their samples were contaminated with benzethonium chloride, a synthetic preservative, and some were contaminated with other preservatives, some of which really weren’t very safe at all. And here’s the kicker, the samples that weren’t contaminated had no antimicrobial properties.

In other words, either your ‘natural’ grapefruit seed extract is a preservative because it’s contaminated with synthetic preservatives, or it’s not a preservative at all.

If you're worried, just use cotton wool pads and water.

You can always use cotton wool pads and water.

If you’re worried that baby wipes may be irritating your baby’s skin – I’m not claiming this never happens – then the best, and cheapest, thing to do would be to simply follow the NHS guidelines and use cotton wool and water. It’s actually easier and less messy than you might imagine – packets of flat, cosmetic cotton wool pads are readily available (and pretty cheap). Simply dip one in some clean water, wipe and throw it away. It’s really no more difficult or messy than wipes.

But if you’re choosing a particular brand of wipes on the basis that they’re “chemical-free”, despite the fact that other types have never actually caused irritation, you can stop. Really. Buy the cheap ones. Or the nicest-smelling ones, or the ones that come out of the packet most easily. Because NONE of them are chemical-free, and it’s really not a problem.

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Basic Chemistry

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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.