Is fluorocarbon biodegradable? (3 categories of fluorocarbons)

This article shall answer the question of the biodegradability of fluorocarbons.

It shall further delve into other areas such as:

  • Types of fluorocarbons.
  • Properties and applications of fluorocarbons.
  • Toxicity of fluorocarbons.
  • Eco-friendliness of fluorocarbons.

Is fluorocarbon biodegradable?

No, fluorocarbon molecules are not biodegradable. The organofluorine compounds contain some plastic properties which render them unsusceptible to microbial degradation.

The process of biodegradation takes place in the organic compounds that are derived from plants and animals.

What is biodegradation?

Biodegradation is the process by which naturally occurring organic materials are broken down by microorganisms such as bacteria and fungi into small particles which are not harmful to the environment.

Biodegradation is carried out by different agents such as UV radiation, light, wind, and water but the most effective agents of biodegradation are bacteria and fungi.

Biodegradation occurs in three distinct stages: biodeterioration, bio-fragmentation, and assimilation.

The biodeterioration process loosens up the structure of the organic substance. For instance, the cell wall of plants is weakened by light, wind, water, and UV radiation.

Bio-fragmentation involves the breakdown of organic matter into smaller, nontoxic particles by bacteria and fungi, releasing water and carbon dioxide in the process.

Assimilation is the last stage of biodegradation and it involves the microorganisms taking up the products of bio-fragmentation into their biological machinery to be used to make energy.

Biodegradation can either involve the microorganisms using oxygen, aerobic biodegradation or it can involve the microorganisms which do not use oxygen, anaerobic biodegradation.

Aerobic biodegradation breaks down organic matter into small biomass, producing carbon dioxide and water.

Anaerobic biodegradation breaks down organic matter into small biomass and in the process carbon dioxide and methane gases are produced.

Aerobic biodegradation occurs at a faster rate than anaerobic biodegradation whereas anaerobic respiration is more efficient and produces more gases and other products.

What are fluorocarbons?

These are organofluorine compounds with the formula CxFy. They are made of only carbon and fluorine elements.

They are also called perfluorocarbons.  They are classified into four categories:

  • Perfluoroalkanes.
  • Fluoroalkenes.
  • Fluoroalkynes.
  • Perfluoro Aromatic compounds

Fluorocarbons and their derivative compounds such; as perfluorinated compounds are used as fluoropolymers l, refrigerants, solvents, and anesthetics.

Perfluoroalkanes.

These compounds are very stable because of their carbon-fluorine bonds. 

Properties of perfluoroalkanes.

The following are the properties of perfluoroalkanes.

  • They are colorless.
  • They have a high density.
  • They are immiscible with most organic solvents like acetone, ethyl acetate, ethanol, and chloroform.
  • They are miscible with some hydrocarbons such as hexane
  • They are less soluble in water.
  • They have a low refractive index.
  • They are hydrophobic, lipophobic, and non-polar.
  • They have a low heat of vaporization, low viscosity, and low surface tension.
  • They dissolve gases easily.
  • They are highly compressible.

Examples of perfluoroalkanes.

The following are examples of perfluoroalkanes.

Hexafluoroethane.

This molecule resembles ethane in the alkane group. It is a non-flammable gas that is slightly soluble in water.

Properties of hexafluoroethane.

The following are the properties of hexafluoroethane.

  • In its solid phase, it occurs in 2 forms.
  • It has different transition temperatures.
  • Low flammability.

Applications of hexafluoroethane.

The following are the uses of hexafluoroethane.

  • It is used as an etchant in semiconductor manufacturing.
  • It is used in refrigerants together with trifluoromethane.

Perfluoropentane.

This is the fluorine analog of the pentane molecule. It is a liquid compound that boils at almost room temperature.

It is used in the biomedical field as a propellant for pressurized metered-dose inhalers, gas core in microbubble ultrasound contrast agents, and occlusion therapy.

Perfluoromethylcyclohexane.

This is a liquid molecule derived from methylcyclohexane.

It is an inert compound.

It is stable at high temperatures. It is a colorless liquid with high density, low viscosity, and low surface tension.

It dissolves gases but does not dissolve solids. It is immiscible in most liquids.

It is used as a heat transfer agent, a dielectric fluid, and as a perfluorocarbon tracer.

Perfluorodecalin.

It is a derivative of decalin alkane.

It is stable under high temperatures.

It is chemically and biologically inert.

It can easily dissolve gases.

Applications of perfluorodecalin.

It is used:

  • Making artificial blood, fusol.
  • In liquid breathing.
  • As a tissue preservative for pancreas transplants.
  • Used for oxygen delivery during cell culture.
  • It is used to dissolve Teflon AF.

Fluoroalkynes and fluoroalkenes.

These are unsaturated fluoro compounds. They are more reactive than fluoroalkanes.

They include the following compounds.

  • Perfluoroisobutene-  this is a molecule that resembles isobutene. It is a colorless alkene gas that is highly toxic.
  • Tetrafluoroethylene- This is the simplest compound in the perfluorinated alkene group. It is a gas that is highly used in fluoropolymers.

It is colorless and odorless and is susceptible to nucleophilic attacks.

It can easily decompose into carbon and carbon tetrafluoride. It easily explodes when in contact with air.

It is used in the production of Teflon and fluon polymers. It is also used to make fluoroplastics.

The compound has been categorized as carcinogenic.

  • Hexafluoropropylene- this is a compound that resembles propylene.

It is mainly used as a chemical intermediate such as producing copolymers when used with tetrafluoroethylene.

  • Hexafluoro-2- butyne- is an electrophilic acetylene derivative and therefore a good dienophile for Diels-Alder reactions.

It is produced by reacting sulfur tetrafluoride with acetylene dicarboxylic acid or by reacting potassium fluoride with hexachlorobutadiene.

Perfluoro aromatic compounds.

These are compounds that contain carbon-fluorine, and an aromatic ring.

They are relatively volatile, have high density, and are non-flammable. They are colorless liquids that are miscible with most solvents.

The compounds in this category include:

Hexafluorobenzene.

This compound is also called perfluorobenzene. It is an aromatic compound that contains a benzene ring.

The uses of hexafluorobenzene include:

  • It is mostly used as a solvent in photochemical reactions.
  •  In UV/vis and fluorine-19 spectroscopy. 
  • Nuclear magnetic resonance (NMR).
  • The solvent in the study of the IR spectrum.
  • Used in the investigation of tissue oxygenation.

The molecule can cause skin and eye irritation, respiratory and digestive tract irritation, and depression of the central nervous system. It is listed as a neurotoxicant. 

The molecule is synthesized from alkali-fluorides with halogenated benzene.

What are fluoropolymers?

These are polymer compounds that are derived from fluorocarbons. They have high resistance to solvents, acids, and bases. They are characterized as thermoplastic or thermosetting plastics.

The most popular type of fluoropolymer is polytetrafluoroethylene, also known as Teflon.

Fluoropolymers are made from the following monomers.

  • Perfluoro Cycloalkene.
  • Ethylene.
  • Vinyl fluoride (fluoroethylene).
  • Vinylidene fluoride.
  • Tetrafluoroethylene.
  • Chlorotrifluoroethylene.
  • Propylene.
  • Hexafluoropropylene.
  • Perfluoropropyl Vinyl Ether.
  • Perfluoromethyl Vinyl Ether.

What is Teflon?

This is a polymer of fluorocarbon tetrafluoroethylene. 

The chemical name is polytetrafluoroethylene (PTFE). It has common trade names such as Teflon and spin-off.

Properties of Teflon.

The following are the properties of Teflon.

  • It is a solid molecule.
  • It is hydrophobic.
  • It is inert.
  • It has high strength and is durable.
  • It has good flexibility at high temperatures.
  • It is affected by alkali metals.
  • It is thermoplastic.

Applications of Teflon.

The following are the uses of Teflon.

  • It is used as a wire and electronic insulator.
  • It is used for plain bearings, gears, seals, gaskets, and bushings.
  • It is used to make electrets.
  • Used in the production of fiberglass and carbon fiber components.
  • Used in making chemically inert liners.
  • Used to make lubricating oil for musical instruments.
  • Used to coat kitchenware.

Are fluorocarbons toxic?

According to a study report, Fluorinated alkene and alkynes such as perfluoroisobutene are toxic. The chemicals can bioaccumulate in the bodies, causing several infections.

Hexafluorobenzene can cause skin and eye irritation, respiratory and digestive tract irritation, and depression in the central nervous system. It is listed as a neurotoxicant. 

Tetrafluoroethylene has been listed as a potential carcinogen.

Are fluorocarbons eco-friendly?

Due to their inert and highly dense nature, fluorocarbons accumulate in the environment causing pollution.

Fluoropolymers are very reactive and they produce fluorocarbon gases that are potent greenhouse gases, which deplete the ozone layer, causing global warming.

Tetrafluoroethylene is a very reactive compound that can easily explode when it comes into contact with air, it should be handled with a lot of care.

Conclusion.

This article has answered the question of the biodegradability of fluorocarbons.

It has also covered other areas such as:

  • Types of fluorocarbons.
  • Properties and uses of fluorocarbons.
  • Fluorocarbon toxicity.
  • Eco-friendliness of fluorocarbons.

For any questions or comments please use the comment section below.

Frequently Asked Questions (FAQs): is fluorocarbon biodegradable? 

Why are fluorocarbons harmful?

Fluorocarbon gases are potent greenhouse gases and may cause global warming.

Some fluorocarbons such as tetrafluoroethylene are carcinogenic. Some fluorocarbons also are said to cause skin and eye irritation.

Is fluorocarbon a plastic?

Some fluorocarbons are thermoplastic. An example is Teflon which is applied in industries.

What is fluorocarbon material?

This is an organofluorine compound that contains carbon and fluorine in its structures.

Citations.

O’Hagan D (February 2008). “Understanding organofluorichemistry. An introduction to the Cā€“F bond”. Chem. Soc. Rev. 37 (2): 308ā€“19. doi:10.1039/b711844a

Kiplinger JL, Richmond TG, Osterberg CE (1994). “Activation of Carbon-Fluorine Bonds by Metal Complexes”. Chem. Rev. 94 (2): 373ā€“431. doi:10.1021/cr00026a005.

Liu, Y., Miyoshi, H., and Nakamura, M. Encapsulated ultrasound microbubbles: Therapeutic application in drug/gene delivery. J. Controlled Release 2006, 114, 89āˆ’ 99

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