Divinylbenzene

Divinylbenzene (DVB) is an organic compound with the chemical formula C6H4(CH=CH2)2 and structure H2C=CH−C6H4−HC=CH2 (a benzene ring with two vinyl groups as substituents). It is related to styrene (vinylbenzene, C6H5−CH=CH2) by the addition of a second vinyl group.[2] It is a colorless liquid 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]

Divinylbenzene
Skeletal formulae of both isomers
Ball-and-stick model of m-Divinylbenzene
Ball-and-stick model of m-Divinylbenzene
Ball-and-stick model of p-Divinylbenzene
Ball-and-stick model of p-Divinylbenzene
Names
Other names
Diethylene benzene, DVB, Vinylstyrene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.932
EC Number
  • 215-325-5
  • m-: 203-595-7
  • p-: 203-266-8
RTECS number
  • CZ9370000
  • m-: CZ9450000
UNII
UN number 1993
  • p-: InChI=1S/C10H10/c1-3-9-5-7-10(4-2)8-6-9/h3-8H,1-2H2
    Key: WEERVPDNCOGWJF-UHFFFAOYSA-N
  • C=CC1=CC=CC=C1C=C
  • m-: C=CC1=CC(=CC=C1)C=C
  • p-: C=CC1=CC=C(C=C1)C=C
Properties
C10H10
Molar mass 130.190 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]
NIOSH (US health exposure limits):
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

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

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
  1. 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. 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.
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