Divinylbenzene

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Divinylbenzene
Skeletal formulae of both isomers
Ball-and-stick model of m-Divinylbenzene
Ball-and-stick model of p-Divinylbenzene
Names
Other names
Diethylene benzene, DVB, Vinylstyrene
Identifiers
ChemSpider
  • 60033 (o-Divinylbenzene) N
  • 7653 (m-Divinylbenzene) N
  • 59432 (p-Divinylbenzene) N
ECHA InfoCard 100.013.932
EC Number 215-325-5
Properties
C10H10
Molar mass 130.19 g·mol−1
Appearance pale, straw-colored liquid[1]
Density 0.914 g/mL
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]
Hazards
Flash point 76 °C (169 °F; 349 K)
Explosive limits 1.1%-6.2%[1]
US health exposure limits (NIOSH):
PEL (Permissible)
none[1]
REL (Recommended)
TWA 10 ppm (50 mg/m3)[1]
IDLH (Immediate danger)
N.D.[1]
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] It is a colorless liquid 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]

Production and use[edit]

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 styrene-divinylbenzene, S-DVB or Sty-DVB. The resulting cross-linked polymer is mainly used for the production of ion exchange resin.[3]

Nomenclature[edit]

  • 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[edit]

  1. ^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0248". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ CRC Handbook of Chemistry and Physics 65Th Ed.
  3. ^ a b Denis H. James William M. Castor, “Styrene” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a25_329.pub2.