Hydrodealkylation
Encyclopedia
Hydrodealkylation is a chemical reaction that often involves reacting an aromatic hydrocarbon
Aromatic hydrocarbon
An aromatic hydrocarbon or arene is a hydrocarbon with alternating double and single bonds between carbon atoms. The term 'aromatic' was assigned before the physical mechanism determining aromaticity was discovered, and was derived from the fact that many of the compounds have a sweet scent...

, such as toluene
Toluene
Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...

, in the presence of hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

 gas to form a simpler aromatic hydrocarbon devoid of functional group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...

s. An example is the conversion of 1,2,4-trimethylbenzene
1,2,4-Trimethylbenzene
1,2,4-Trimethylbenzene is a colorless liquid with chemical formula C9H12. It is a flammable aromatic hydrocarbon with a strong odor. It occurs naturally in coal tar and petroleum . It is nearly insoluble in water, but well-soluble in ethanol, diethyl ether, and benzene.Industrially, it is...

 to xylene
Xylene
Xylene encompasses three isomers of dimethylbenzene. The isomers are distinguished by the designations ortho- , meta- , and para- , which specify to which carbon atoms the two methyl groups are attached...

. This chemical process usually occurs at high temperature, at high pressure, or in the presence of a catalyst. These are predominantly transition metal
Transition metal
The term transition metal has two possible meanings:*The IUPAC definition states that a transition metal is "an element whose atom has an incomplete d sub-shell, or which can give rise to cations with an incomplete d sub-shell." Group 12 elements are not transition metals in this definition.*Some...

s, such as chromium
Chromium
Chromium is a chemical element which has the symbol Cr and atomic number 24. It is the first element in Group 6. It is a steely-gray, lustrous, hard metal that takes a high polish and has a high melting point. It is also odorless, tasteless, and malleable...

 or molybdenum
Molybdenum
Molybdenum , is a Group 6 chemical element with the symbol Mo and atomic number 42. The name is from Neo-Latin Molybdaenum, from Ancient Greek , meaning lead, itself proposed as a loanword from Anatolian Luvian and Lydian languages, since its ores were confused with lead ores...

.

Examples

  • Toluene hydrodealkylation to benzene
  • Transalkylation
    Transalkylation
    Transalkylation is a chemical reaction of transfer of an alkyl group from one organic compound to another. Zeolite catalysts are often used. The reaction is widely used in the petrochemical industry to manufacture p-xylene, styrene, and other aromatic compounds....

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