Carbocatalysis is a form of
catalysis
Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...
that uses heterogeneous
carbon
Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
materials for the transformation or synthesis of organic or inorganic substrates. The catalysts are characterized by their high surface areas, surface functionality, and large,
aromatic
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...
basal planes. Carbocatalysis can be distinguishable from supported catalysis (such as
palladium on carbon) in that no metal is present, or if metals are present they are not the active species.
As of 2010, the mechanisms of reactivity are not well understood.
One of the most common examples of carbocatalysis is the oxidative
dehydrogenation
In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...
of
ethylbenzene
Ethylbenzene is an organic compound with the formula . It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediat ...
to
styrene
Styrene is an organic compound with the chemical formula C6H5CH=CH2. Its structure consists of a vinyl group as substituent on benzene. Styrene is a colorless, oily liquid, although aged samples can appear yellowish. The compound evaporates easi ...
discovered in the 1970s.
Also in the industrial process of (non-oxidative) dehydrogenation of ethylbenzene, the
potassium
Potassium is a chemical element; it has Symbol (chemistry), symbol K (from Neo-Latin ) and atomic number19. It is a silvery white metal that is soft enough to easily cut with a knife. Potassium metal reacts rapidly with atmospheric oxygen to ...
-promoted
iron oxide
An iron oxide is a chemical compound composed of iron and oxygen. Several iron oxides are recognized. Often they are non-stoichiometric. Ferric oxyhydroxides are a related class of compounds, perhaps the best known of which is rust.
Iron ...
catalyst is coated with a carbon layer as the active phase. In another early example,
a variety of substituted
nitrobenzenes Nitrobenzenes are a group of nitro compounds consisting of one or more Nitro compound, nitro groups as substituents on a benzene core. They have the formula C6H6–''n''(NO2)''n'', where ''n'' = 1–6 is the number of nitro groups. Depending o ...
were reduced to the corresponding
aniline
Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
using
hydrazine
Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydraz ...
and graphite as the catalyst.
The discovery of nanostructured carbon
allotropes
Allotropy or allotropism () is the property of some chemical elements to exist in two or more different forms, in the same physical state, known as allotropes of the elements. Allotropes are different structural modifications of an element: th ...
such as
carbon nanotubes
A carbon nanotube (CNT) is a tube made of carbon with a diameter in the nanometre range (nanoscale). They are one of the allotropes of carbon. Two broad classes of carbon nanotubes are recognized:
* ''Single-walled carbon nanotubes'' (''SWC ...
,
fullerenes
A fullerene is an allotrope of carbon whose molecules consist of carbon atoms connected by single and double bonds so as to form a closed or partially closed mesh, with fused rings of five to six atoms. The molecules may have hollow sphere- ...
,
or
graphene
Graphene () is a carbon allotrope consisting of a Single-layer materials, single layer of atoms arranged in a hexagonal lattice, honeycomb planar nanostructure. The name "graphene" is derived from "graphite" and the suffix -ene, indicating ...
promoted further developments. Oxidized carbon nanotubes were used to dehydrogenate
n-butane to
1-butene
1-Butene (IUPAC name: But-1-ene, also known as 1-butylene) is the organic compound with the formula CH3CH2CH=CH2. It is a colorless gas, but easily condensed to give a colorless liquid. It is classified as a linear alpha-olefin (terminal alkene). ...
,
and to selectively oxidize
acrolein
Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat ...
to
acrylic acid
Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has ...
.
Fullerenes were used in the catalytic reduction of nitrobenzene to aniline in the presence of
H2.
was used as a carbocatalyst to facilitate the
oxidation
Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...
of
alcohols
In chemistry, an alcohol (), is a type of organic compound that carries at least one hydroxyl () functional group bound to a Saturated and unsaturated compounds, saturated carbon atom. Alcohols range from the simple, like methanol and ethanol ...
to the corresponding
aldehydes
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
/
ketones
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
(shown in the picture), the
hydration of
alkynes
\ce
\ce
Acetylene
\ce
\ce
\ce
Propyne
\ce
\ce
\ce
\ce
1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no ...
, and the oxidation of
alkenes
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins.
The Internationa ...
.
References
{{Reflist
External links
Carbon Materials for Catalysis
Catalysis