Divinylbenzene (DVB) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

and

structure A structure is an arrangement and organization of interrelated elements in a material object or system, or the object or system so organized. Material structures include man-made objects such as buildings and machines and natural objects such as ...

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

ring with 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 contai ...

s as

substituents In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety (chemistry), moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that conta ...

). It is related 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 ...

(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 105th edition, published in 2024. It is known colloquially among chemists as ...

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 Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...

and thus is not a component of the usual mixtures of DVB.

Production and use

It is produced by dehydrogenation of diethylbenzene: : C₆H₄(C₂H₅)₂ → C₆H₄(C₂H₃)₂ + 2 H₂ 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 som ...

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 An ion-exchange resin or ion-exchange polymer is a resin or polymer that acts as a medium for ion exchange, that is also known as an ionex. It is an solubility, insoluble matrix (or support structure) normally in the form of small (0.25–1.43&nbs ...

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 is used in solid-phase synth ...

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 Phenylene compounds