Hexane/ C6H14: A Complete Amazing Overview

Hexane is an organic substance that falls under the category of an alkane, a form of hydrocarbon with only one covalent connection between the carbon atoms. It is a liquid that has the molecular composition C6H14 and has neither colour nor smell. Hexane’s distinctive structure is one of its most important qualities. It is made up of 14 hydrogen atoms coupled to six carbon atoms that are organized in a straight chain. It gets its name from this linear structure because the word “hex” alludes to the chain’s six carbon atoms. It is a volatile chemical since it is very flammable and has a low boiling point.

It is a naturally occurring substance that is present in trace concentrations in some natural gas and crude oil reserves. Additionally, it can be found in trace levels in some plants and essential oils. There are traces of it in several fruits, vegetables, and nuts. However, petroleum refinement is the main method of production.

Due to its low polarity and capacity to dissolve a variety of non-polar substances, it is frequently used as a solvent. It is non-polar, which renders it largely insoluble in water, which is a polar solvent. Hexane is far more soluble in non-polar solvents, such as those found in other hydrocarbons and organic substances. It is a useful solvent because of its feature in a variety of industrial and laboratory operations where non-polar compounds need to be dissolved or extracted.

It is frequently used to extract oils from seeds and nuts, including soybeans, peanuts, and sunflower seeds. The procedure entails dissolving the oil in hexane, removing the oil from the solid components, and then letting the it evaporate, leaving behind the oil that was extracted. It is widely used, however because of its flammability and because of associated health risks, it should be handled carefully.

Polar or Non-polar?

The chemical hexane is non-polar. It is made up of a straight chain of six carbon atoms, each of which is joined to two hydrogen atoms. Since all the atoms in the molecule have equal electronegativities and the carbon-hydrogen bonds are non-polar, there are no discernible changes in the distribution of electrons inside the molecule.

Since the electron density is uniformly distributed across the molecule, hexane has a symmetrical and linear structure. It is non-polar due to its symmetry and uniform electron density distribution. There are no permanent dipoles and no net charges in non-polar molecules.

Hexane Physical Properties:

  1. Molar mass: 86.18 g/mol
  2. Density: It has a density of approximately 0.659 g/cm3.
  3. Boiling Point: It has a boiling point that is rather low, at about 68.7°C.
  4. Melting Point: The melting point is approximately -95°C.
  5. Flash Point: Hexane is extremely combustible and has a comparatively low flash point of -22°C.
  6. Solubility: In nonpolar organic solvents like benzene, ether, and chloroform, it is quite soluble. It is extremely soluble in lipids due to its non-polarity and low molecular weight. It is frequently used as an extraction solvent for oils from plant sources since it can easily breakdown lipids and fats.
  7. Viscosity: It flows freely because of its low viscosity.

Hexane Chemical Properties:

  1. Hexane is very flammable and easily starts to burn when it encounters an ignition source, like an open flame or spark.
  2. It is an alkane hydrocarbon, which means that all its atoms—carbon and hydrogen—are joined by a single covalent bond.
  3. Due to its non-polar structure, hexane normally has little reaction with most common compounds and reagents. In the presence of oxygen or air, it can take part in radical processes and is vulnerable to oxidation.
  4. It’s outstanding non-polar solvent properties make it a popular choice for extraction and purification procedures in labs and businesses.
  5. It is thought to be neutral and does not have any acidic or basic characteristics in water.

Synthesis/ Production:

It can be made in a variety of ways, although the most popular ones involve hydrogenating certain hydrocarbons. While these techniques are employed to create hexane, industrial-scale production frequently depends on petroleum fractional distillation.

Catalytic Hydrogenation of Alkenes:

The catalytic hydrogenation of alkenes is one of the main processes used to make hexane. Unsaturated hydrocarbons having double bonds between carbon atoms are alkenes. Alkenes can be changed into alkanes by adding hydrogen atoms to the double bond in the presence of a suitable catalyst and hydrogen gas. For instance, 1-hexene (C6H12) can be hydrogenated using a suitable catalyst, such as palladium (Pd) or platinum (Pt), while being exposed to high temperatures and pressures of hydrogen gas.

C6H12 + 3H2 → C6H14

Hydrogenation of Alkynes:

The hydrogenation of alkynes is another process used to make hexane. Unsaturated hydrocarbons having triple bonds between carbon atoms are alkynes. Similar circumstances can be used for hydrogenating alkynes as they are for hydrogenating alkenes to make alkanes. For instance, with a suitable catalyst and hydrogen gas, 1-hexyne (C6H10) can be hydrogenated.

C6H10 + 4H2 → C6H14

From Fractional Distillation of Petroleum:

Additionally, It is produced as a byproduct of petroleum fractional distillation. Varying hydrocarbons with differing boiling points make up crude oil. Crude oil is heated and distilled throughout the refining process to split it into several fractions according to their boiling points. The petrol fraction contains hexane, which can be further refined through further distillation procedures.

From Cracking of Longer Hydrocarbons:

In the petrochemical industry, cracking is a method used to split longer hydrocarbon molecules into smaller ones. This method is frequently used to convert bigger hydrocarbons found in crude oil or natural gas into smaller hydrocarbons, such as hexane. Longer hydrocarbon molecules are heated to high temperatures during the cracking process, which causes them to split into smaller molecules. By controlling the cracking conditions, hexane can be produced along with other smaller hydrocarbons.

Laboratory Synthesis:

Hexane can be produced in a laboratory setting by reducing appropriate alkyl halides with reactive metals like lithium or sodium in anhydrous ether as a solvent. For instance, utilizing lithium metal to reduce 1-chlorohexane can result in the synthesis of n-hexane.

CH3(CH2)4Cl (1-chlorohexane) + 2Li → CH3(CH2)5CH3 (n-hexane) + 2LiCl

Chemical Reaction:

Hexane experiences several chemical processes that are common to alkanes because it is an aliphatic hydrocarbon. In these processes, bonds between carbon atoms and hydrogen atoms are either broken or formed. Instead of being a significant industrial activity using hexane, most of the chemical reactions involving hexane take place in laboratories or in the synthesis of other chemicals. Due to hexane’s high reactivity and volatility, many of these reactions are also impractical to perform on a wide scale.

  1. Combustion: Alkanes and oxygen frequently combine during combustion to produce carbon dioxide (CO2) and water (H2O). Hexane burns with a strong exothermic reaction that generates a lot of heat.

19/2 O2 + C6H14 → 6CO2 + 7H2O

  1. Halogenation: A halogen atom (iodine, bromine, or chlorine) is substituted for a hydrogen atom in an alkane in a process known as halogenation. Hexane can be halogenated in the presence of heat or UV with Cl2 or Br2.

C6H14 + Br2 → C6H13Br + HBr

  1. Nitration: A nitronium ion (NO2+) and an alkane undergo a substitution reaction known as nitration. A nitro group (-NO2) is added to the hydrocarbon chain because of this reaction. Hexane’s relatively low reactivity makes the nitration reaction uncommon.
  2. Free Radical Substitution: It can experience free radical substitution reactions under specific circumstances, such as when light or heat are present. In these reactions, carbon-hydrogen bonds are broken, and a hydrogen atom is changed for a different radical group. When hexane is chlorinated in the presence of light, for instance, a variety of chlorinated hexane isomers might result.

C6H14 + Cl2 → C6H13Cl + HCl

  1. Dehydrogenation: Alkanes lose hydrogen atoms during the dehydrogenation reaction, resulting in the formation of alkene. High temperatures are needed for the reaction, which frequently takes place in a controlled environment. Dehydrogenation of hexane can result in the production of hexenes.

C6H14 → C6H12 + H2

Applications:

It is a flexible organic solvent with several uses across numerous industries. Due to its special characteristics, including low polarity, low boiling point, and high volatility, it can be used for a variety of things.

  1. Effect on Insects: It is sometimes applied in agricultural settings to extract insect pheromones for pest management. These pheromones can be utilized to interfere with an insect pest’s mating behaviour and stop it from reproducing.
  2. Solvent in Industrial Processes: It is frequently utilized as a solvent in industrial processes, particularly when removing vegetable oils from seeds and nuts. It is a perfect solvent for oil extraction in sectors like food processing and biofuels since it is very successful at liquefying fats, oils, and other organic molecules.
  3. Laboratory Solvent: It is frequently employed as a non-polar solvent in laboratories for a variety of purposes. It is frequently employed to dissolve and extract chemical substances, to divide mixtures, and to carry out chromatography procedures. Working with non-polar substances is made easier by its non-polar character.
  4. Cleaning Agent: It is used as a cleaning agent in a variety of industries, including optics and electronics. It is useful for precision cleaning since it removes oils, grease, and other impurities from surfaces effectively. 
  5. Adhesive and Rubber Industry: It is a crucial ingredient in the manufacturing of rubber and adhesive goods.  Due to its capacity to simplify the mixing and processing of these components, it is utilized to dissolve and process various rubber compounds and adhesives.
  6. Paints and Coatings: It is a solvent that is used in the paints and coatings industry to disperse pigments and resins. It is frequently used in spray paints and aerosol coatings and aids in the creation of homogeneous mixes.
  7. Alternative to Chlorinated Solvents: It is occasionally used in laboratories in place of chlorinated solvents because it is less hazardous and less harmful to the ozone layer.
  8. Fuel Blend: It can be added to petrol mixes to raise the octane level. By lowering knocking and raising engine performance, it improves petrol performance.
  9. Pharmaceutical and Cosmetic Industries: It is used as a solvent in the manufacturing of pharmaceuticals and cosmetic items for the extraction, purification, and formulation procedures.
  10. Food firm: It is crucial in the food business for obtaining vegetable oils that are frequently used for cooking, baking, and food preparation, even though it is primarily employed to extract oil from plants.

Safety Considerations:

  1. Hexane is highly flammable due to its low flash point and high volatility. To prevent fire hazards, proper handling, handling, and storage must be used.
  2. Long-term, high-concentration inhalation of hexane vapor might irritate the respiratory system and result in nausea, dizziness, and vomiting. Working with hexane must be done in well-ventilated environments or beneath a fume hood.
  3. It exposure can dry up and irritate the skin. When handling this chemical, it is important to put on the proper protective clothing, such as gloves and lab coats.
  4. Prolonged exposure to hexane vapor can harm and depress the central nervous system. Limit your time spent in high concentrations.

What is the toxic effect of Hexane?

Both people and animals are susceptible to the neurotoxic effects of hexane. Long-term exposure to hexane vapors at high concentrations can harm the peripheral nerve system, resulting in symptoms like tingling, numbness, and weakening in the extremities.

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