Adipic Acid: Formula, Structure & Properties

Instructor: Darla Reed

Darla has taught undergraduate Enzyme Kinetics and has a doctorate in Basic Medical Science

In this lesson you will discover what adipic acid is, what it is composed of and what it looks like. You will also learn a little about what it can do and some of its uses.

Formula and Structure of Adipic Acid

Mom, dad, racecar, kayak, radar, sagas - can you guess what these words have in common? They are palindromes. Palindromes are words that can be read the same way backward as forward. What these words have in common with adipic acid is simple - the structural formula of adipic acid is like a palindrome.

Adipic acid is composed of carbon, hydrogen and oxygen. Its basic formula is C6H10O4. This means it has a total of 6 carbons, 10 hydrogens and 4 oxygens. If you write it as a basic formula, it doesn't look much like a palindrome, but how about if it was written like this: HOOCHCHHCHHCHHCHCOOH.

You'll notice at the beginning and the end there is a HOOC. This group is known as a called a carboxyl group.

carboxyl group/carboxylic acid
Carboxyl group structure

When attached to other groups in chemistry it is referred to as a carboxylic acid. A carboxyl group makes up both ends of adipic acid, and since there are two of them, adipic acid is categorized as a dicarboxylic acid (di meaning 2). Adipic acid isn't its only name, but it's the one most commonly used.

Stuck in the middle of the two carboxylic acids is a group of four carbons with two hydrogens that is often abbreviated (CH2)4. Thus the structure of adipic acid is a 6 carbon chain with two carboxylic acid groups at each end.

Structure of adipic acid.
adipic acid structure

Properties of Adipic Acid

So now we know the formula and structure adipic acid, what are some of its properties? What does it look like? What is known about it? Well, for one it is a white crystalline solid at room temperature - this means it kinda looks like salt or white sand. It's also slightly flammable. This means if you add a little heat you might get a fire. If you add extremely high heat you may even get a little bit of an explosion!

Apparently someone thought it would be a good idea to taste it, so we know adipic acid has a tart taste, though I wouldn't recommend eating it, since it'll mess with your digestive system. Also, it's not called an acid for nothing. If you add it to water solutions, it becomes corrosive and can act just like the name suggests - an acid. In fact, because it has two carboxylic acids attached at the ends, it can react with two bases. Thus it is known as a dibasic acid.

Just in case you're thinking of inhaling the lovely white crystalline solid, it's definitely not recommended, since it irritates your lungs and can make you sneeze, cough, cough up blood, or can even cause asthma.

Although adipic acid is biodegradable, its formation can have environmental consequences. One of the byproducts of adipic acid formation from benzene is nitrous oxide (N2O), a greenhouse gas. Scientists however are working on environmentally friendly ways of producing adipic acid.

Uses of Adipic Acid

All that being said, adipic acid has a wide variety of uses and over 4.4 billion pounds of it has been produced worldwide. So what kind of uses does it have?

It can be combined with other molecules or some chemical groups can be added to the four middle carbons to make a useful product. For example, when it is combined with hexamethylenediamine - yeah it's a long, complicated name - but when you put that with adipic acid it makes a form of nylon called nylon 6,6.

Adipic acid is used to make Nylon 6,6.
Nylon 6,6 formation

Nylon 6,6 is used in carpeting, clothing, cords and mechanical parts.

In addition, adipic acid is useful for making plastics or polyesters. In particular, it has been used in food wrap and blood bags. Forms and derivatives of adipic acid are also used as a vehicle for pharmaceutical drugs - this means it helps the drug get into your body when you're sick.

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