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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
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Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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In mass spectrometry, cycloalkanes exhibit distinct fragmentation patterns due to the inherent stability of their molecular ions compared to linear or branched alkanes. The ring structure of cycloalkanes provides additional stability to the molecular ions, often resulting in prominent ion peaks in the mass spectrum.
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Separation of Benzene and Cyclohexane Using Eutectic Solvents with Aromatic Structure.

Mohamed K Hadj-Kali1, M Zulhaziman M Salleh2, Irfan Wazeer1

  • 1Chemical Engineering Department, King Saud University, Riyadh 11421, Saudi Arabia.

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Summary

This study explores eutectic solvents (ESs) for separating benzene and cyclohexane, crucial petrochemicals with similar boiling points. Aromatic-based ESs show promise for efficient extractive separation, offering an alternative to traditional methods.

Keywords:
COSMO-RSLLEbenzenecyclohexaneeutectic solventsionic liquids

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Area of Science:

  • Petrochemical Engineering
  • Separation Science
  • Green Chemistry

Background:

  • Benzene and cyclohexane separation is difficult due to close boiling points.
  • Effective extractive solvents are needed for this petrochemical process.
  • Eutectic solvents (ESs) offer potential as novel separation media.

Purpose of the Study:

  • To screen and evaluate aromatic-based eutectic solvents (ESs) for benzene-cyclohexane extractive separation.
  • To compare the performance of selected ESs against conventional solvents and other ESs.
  • To validate computational predictions with experimental liquid-liquid equilibrium data.

Main Methods:

  • Screening of 23 aromatic-containing eutectic solvents (ESs) using COSMO-RS predictive model.
  • Experimental liquid-liquid equilibrium (LLE) studies for three promising ESs with benzene and cyclohexane.
  • Comparative analysis of ES performance against literature data for organic solvents and ionic liquids.

Main Results:

  • COSMO-RS screening identified several promising aromatic-based ESs.
  • Experimental LLE data confirmed the extractive potential of selected ESs.
  • The studied ESs demonstrated competitive or superior performance compared to existing solvents.

Conclusions:

  • Aromatic-containing eutectic solvents (ESs) are effective for benzene-cyclohexane separation.
  • ESs offer a viable and potentially improved alternative for this challenging petrochemical separation.
  • This research highlights the utility of predictive modeling and experimental validation in solvent discovery.