Divinylbenzene (DVB) consists of a
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
ring
bonded to two
vinyl group
In organic chemistry, a vinyl group (abbr. Vi; IUPAC name: ethenyl group) is a functional group with the formula . It is the ethylene (IUPAC name: ethene) molecule () with one fewer hydrogen atom. The name is also used for any compound contain ...
s. It is related to
styrene
Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concen ...
(vinylbenzene) by the addition of a second vinyl group.
CRC Handbook of Chemistry and Physics
The ''CRC Handbook of Chemistry and Physics'' is a comprehensive one-volume reference resource for science research. First published in 1914, it is currently () in its 103rd edition, published in 2022. It is sometimes nicknamed the "Rubber Bible ...
65Th Ed. It is a colorless liquid manufactured by the thermal
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 isomeric diethylbenzenes. Under synthesis conditions, ''o''-divinylbenzene converts to
naphthalene
Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...
and thus is not a component of the usual mixtures of DVB.
Production and use
It is produced by dehydrogenation of
diethylbenzene:
: C
6H
4(C
2H
5)
2 → C
6H
4(C
2H
3)
2 + 2 H
2
Divinylbenzene is usually encountered as a 2:1 mixture of ''m''- and ''p''-divinylbenzene, containing also the corresponding isomers of ethylvinylbenzene.
Styrene and divinylbenzene react to form the
copolymer
In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are some ...
styrene-divinylbenzene, S-DVB or Sty-DVB. The resulting
cross-link
In chemistry and biology a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural ...
ed polymer is mainly used for the production of
ion exchange resin and
Merrifield resin Merrifield Resin is a cross-linked polystyrene resin that carries a chloromethyl functional group. Merrifield resin is named after its inventor, Robert Bruce Merrifield (1984 winner of the Nobel Prize in Chemistry), and used in solid-phase synthesi ...
s for peptide synthesis.
[
]
Nomenclature
* ''Ortho'': variously known as 1,2-diethenylbenzene, 1,2-divinylbenzene, ''o''-vinylstyrene, ''o''-divinylbenzene
* ''Meta'': known as 1,3-diethenylbenzene, 1,3-divinylbenzene, ''m''-vinylstyrene, ''m''-divinylbenzene
* ''Para'': known as 1,4-diethenylbenzene, 1,4-divinylbenzene, ''p''-vinylstyrene, ''p''-divinylbenzene.
These compounds are systematically called diethenylbenzene, although this nomenclature is rarely encountered.
References
{{Hydrocarbons
Vinylbenzenes
Monomers
C4-Benzenes