chemistry

Perfluorodecanoic acid

Perfluorodecanoic acid is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Perfluorodecanoic acid rather than just read about it. In short: Perfluorodecanoic acid (PFDA) is a fluorosurfactant and has been used in industry. PFDA is a member of the group of polyfluoroalkyl substances (PFAS), more specific is it also a perfluoroalkyl acid (PFAA).

Key takeaways

Perfluorodecanoic acid belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Perfluorodecanoic acid to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Perfluorodecanoic acid from memory before moving on to harder problems.

Reference excerpt

Perfluorodecanoic acid (PFDA) is a fluorosurfactant and has been used in industry. PFDA is a member of the group of polyfluoroalkyl substances (PFAS), more specific is it also a perfluoroalkyl acid (PFAA). PFAS, like PFDA, are man-made and are not naturally occurring in nature. Over the last decades they have been used in consumer products and industrial applications. It is a fluorosurfactant with a unique hydrophobicity and oleophobicity. PFDA is well resistant to heat, oil, stains, grease and water, therefore it has been used in stain and greaseproof coating for furniture, packaging and carpet. Next to that, PFDA has also been found in nano-and impregnation-sprays, outdoor textiles, gloves, ski wax, leather, cosmetics, medical equipment and paper-based food containers. PFDA has a relatively high toxicity and can promote tumor growth. It was recently linked to health concerns, like other fluorosurfactants, leading to proposed restrictions on its use. In 2020, a California bill banned its use as an intentionally added ingredient in cosmetics. It has been proposed as a chemical probe to study peroxisome proliferation.

Structure and reactivity Perfluorodecanoic acid is a compound with a carbon chain of 10. At 9 of the carbons the hydrogens are replaced by all fluorine atoms, the last carbon is the carboxylate group. The length of the PFDA carbon chain is greater than that of PFOAs (perfluorooctanoic acids) and PFOS (perfluorooctane sulfonic acid) indicating that it is possibly more toxic. Perfluorodecanoic acid is a chemically inert due to relatively high organic bond strength and fluorine's electron negativity, which makes it resistant to advanced oxidation processes. It is also resistant to hydrolysis and has thermal and photochemical stability unless certain reaction conditions are introduced, e.g., PFDA can be decomposed in hot water in the presence of S2O82-. Photochemical decomposition with Na2S is another way of breaking up PFDA molecules.

Synthesis and reactions The first main road of perfluorochemicals (to which PFDA belongs) is electrochemical fluorination (ECF). This reaction occurs during an electrochemical hydrolysis of hydrofluoric acid (anhydrous) at a cell potential of 4.5 to 7 V. Several compounds can be used as starting material, for example, carboxylic acids (RCOOH), acyl chlorides (RCOCl) or sulfonic acid chlorides (RSO2Cl). The second step of the reaction is hydrolysis (addition of NaOH) to obtain the final products:

The second main synthesis road for perfluorodecanoic acid used commercially is telomerization. Since PFDA has an even number of carbons, the starting material should be pentafluoroethyl iodide. The process follows the general scheme:

Telomerization Tetrafluoroethylene ↓ Perfluoroalkyl iodide ↓ Fluorotelomer alcohols (FTOH) ↓ Perfluorochemicals (e.g. PFDA)

Biochemical effects Via contaminated water or soil, plants can take up PFDA. This may lead to exposure and accumulation of PFDA in humans and other organisms. In addition, exposure is possible via inhalation of indoor and outdoor air and ingestion of drinking water and food. Direct dermal contact with PFDA-containing products is the main route of exposure. PFDA has been shown to increase the expression of two cytochrome P450 enzymes, namely Cyp2B10 and 4A14 in mouse liver. In addition, it has been shown to activate the peroxisome proliferator-activated receptor alpha (PPARα). This receptor regulates lipid metabolism. A study looked at the harmful effects of PFDA on the antioxidative defense system in erythrocytes (red blood cells). Their results indicated that PFDA could influence the contents and activity of the biomolecules: GSH, MDA, SOD, CAT and GPx. This can lead to lipid peroxidation and oxidative injury of erythrocytes. The carbon chain length plays an important role, exposure to PFDA resulted in more obvious alterations of these biomolecules than shorter carbon chains of PFAA's. Further, has merging evidence showed that PFDA exposure can be associated with higher plasma triglyceride concentration in humans. It is however unknown how PFDA might affect adipogenesis. HepG2 cells and 3T3-L1 differentiation model were used to detect the effects and mechanism of PFDA on lipid metabolism. PFDA showed to promote cellular triglyceride accumulation and triglyceride content in a concentration dependent manner. It also activated the NLP3 inflammasome. The inflammasome is crucial for induction of lipogenic genes expression in fatty acid synthase (FAS), hydroxymethyl glutaryl coenzyme A synthase (HMGCS) and stearoyl-CoA desaturase 1 (SCD1). Besides, a suggestion can be made that PFDA may promote adipogenesis via an NLRP3 inflammasome-mediates SREBP1 pathway. Also, the expression of SREBP1, which is an important regulator of lipid metabolism, and its target genes were increased after PFDA treatment. The PFDA-induced SREBP1 enhanced expression can be terminated by caspase-1 inhibitor and by siNLRP3.

Degradation PFDA is resistant to hydrolysis, photolysis and biodegradation, this causes persistence of the compound in the environment. With its long carbon chain and carboxylate group, PFDA has some similar structure to amino acids. But it does not biodegrade according to the route of fatty acid metabolism.

Human exposure Studies have shown that there is a decreasing trend in the concentration of PFDA in Danish pregnant women from years of 2008–2013. Germany also follows this trend, while the concentration of this chemical is growing in Japan, Korea, Greenland, and Northern Norway. Under normal conditions, the amount of PFDA in European individuals was 0.8 ng/mL in 2013.

… excerpt ends here. Continue reading the full article.

Worked examples

Example 1 — a first encounter with Perfluorodecanoic acid

Start with the simplest possible case. Write down what Perfluorodecanoic acid claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Perfluorodecanoic acid before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Perfluorodecanoic acid ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Perfluorodecanoic acid

In research: Perfluorodecanoic acid appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Perfluorodecanoic acid in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Perfluorodecanoic acid is common in secondary-school and first-year university syllabi. It links to neighbouring topics Anionic surfactants, Perfluorocarboxylic acids, Persistent organic pollutants under the Stockholm Convention, so understanding it makes those chapters shorter.
In everyday life: Look for Perfluorodecanoic acid outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Perfluorodecanoic acid in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Perfluorodecanoic acid means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Perfluorodecanoic acid out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Perfluorodecanoic acid in simple terms?

Why does Perfluorodecanoic acid matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Perfluorodecanoic acid?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Perfluorodecanoic acid.