Divinylbenzene

Divinylbenzene
Ball-and-stick model of m-Divinylbenzene	Ball-and-stick model of p-Divinylbenzene
Names
	Other names Diethylene benzene, DVB, Vinylstyrene
Identifiers
CAS Number	1321-74-0 ; m-: 108-57-6 ; p-: 105-06-6 ;
3D model (JSmol)	Interactive image; m-: Interactive image; p-: Interactive image;
ChemSpider	60033 ; m-: 7653 ; p-: 59432 ;
ECHA InfoCard	100.013.932
EC Number	215-325-5; m-: 203-595-7; p-: 203-266-8;
PubChem CID	66666; m-: 7941; p-: 66041;
RTECS number	CZ9370000; m-: CZ9450000;
UNII	IZ715T4SBU ; m-: 4S46QL2WFU ; p-: QN8RGZ4ML2 ;
UN number	3252 3254 (stabilized chemical)
CompTox Dashboard (EPA)	DTXSID2025216 ;
	InChI p-: InChI=1S/C10H10/c1-3-9-5-7-10(4-2)8-6-9/h3-8H,1-2H2 Key: WEERVPDNCOGWJF-UHFFFAOYSA-N;
	SMILES C=CC1=CC=CC=C1C=C; m-: C=CC1=CC(=CC=C1)C=C; p-: C=CC1=CC=C(C=C1)C=C;
Properties
Chemical formula	C10H10
Molar mass	130.190 g·mol−1
Appearance	pale, straw-colored liquid
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)
Solubility in water	0.005% (20°C)
Solubility in other solvents	Soluble in ethanol and ether
Vapor pressure	0.7 mmHg (20°C)
Hazards
Flash point	76 °C (169 °F; 349 K)
Explosive limits	1.1%-6.2%
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 10 ppm (50 mg/m3)
IDLH (Immediate danger)	N.D.
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

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

^ ^a ^b ^c ^d ^e ^f ^g NIOSH Pocket Guide to Chemical Hazards. "#0248". National Institute for Occupational Safety and Health (NIOSH).
^ CRC Handbook of Chemistry and Physics 65Th Ed.
^ ^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.

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f ^g NIOSH Pocket Guide to Chemical Hazards. "#0248". National Institute for Occupational Safety and Health (NIOSH).

[crc-2] CRC Handbook of Chemistry and Physics 65Th Ed.

[Ullmann-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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