Divinylbenzene

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Divinylbenzene
Skeletal formulae of both isomers
Names
Other names
Diethylene benzene, DVB, Vinylstyrene
Identifiers
1321-74-0 (o-Divinylbenzene)(p-Divinylbenzene) YesY
108-57-6 (m-Divinylbenzene)
105-06-6 (p-Divinylbenzene)
EC Number 215-325-5
Properties
C10H10
Molar mass 130.19 g·mol−1
Appearance pale, straw-colored liquid[1]
Density 0.93 g/mL (20°C)[1]
Melting point −66.9 to −52 °C (−88.4 to −61.6 °F; 206.2 to 221.2 K)
Boiling point 195 °C (383 °F; 468 K)
0.005% (20°C)[1]
Solubility in other solvents Soluble in ethanol and ether
Vapor pressure 0.7 mmHg (20°C)[1]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Divinylbenzene (DVB) consists of a benzene ring bonded to two vinyl groups. It is related to styrene (vinylbenzene) by the addition of a second vinyl group.[2] Divinylbenzene, as it is usually encountered, is a 2:1 mixture of m- and p-divinylbenzene, containing also the corresponding ethylvinylbenzene isomers. It is manufactured by the thermal dehydrogenation of isomeric diethylbenzenes. Under synthesis conditions, o-divinylbenzene converts to naphthalene and thus is not a component of the usual mixtures of DVB.[3]

Applications

When reacted together with styrene, divinylbenzene can be used as a reactive monomer in polyester resins. Styrene and divinylbenzene react together to form the copolymer styrene-divinylbenzene, S-DVB or Sty-DVB. The resulting cross-linked polymer is mainly used for the production of ion exchange resin.[3]

Density is 0.914 g/mL.

Nomenclature

See also: Arene substitution patterns Divinylbenzene can exist in the form of 3 structural isomers that differ with respect to the positioning of the vinyl groups.

  • 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

  1. 1.0 1.1 1.2 1.3 Cite error: Invalid <ref> tag; no text was provided for refs named PGCH
  2. CRC Handbook of Chemistry and Physics 65Th Ed.
  3. 3.0 3.1 Denis H. James William M. Castor, “Styrene” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.