divinylbenzene
{{short description|1=Organic compound, C₆H₄(CH=CH₂)₂}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 430950526
| Name = Divinylbenzene
| ImageFile = Divinylbenzene (structural diagram).png
| ImageName = Skeletal formulae of both isomers
| ImageSize = 220px
| ImageFileL1 = M-Divinylbenzene-3D-balls.png
| ImageNameL1 = Ball-and-stick model of m-Divinylbenzene
| ImageFileR1 = P-Divinylbenzene-3D-balls.png
| ImageNameR1 = Ball-and-stick model of p-Divinylbenzene
| OtherNames = Diethylene benzene, DVB, Vinylstyrene
| Section1 = {{Chembox Identifiers
| index2_label = m-
| index3_label = p-
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1321-74-0
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 108-57-6
| CASNo3_Ref = {{cascite|correct|CAS}}
| CASNo3 = 105-06-6
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 60033
| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID2 = 7653
| ChemSpiderID3_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID3 = 59432
| PubChem = 66666
| PubChem2 = 7941
| PubChem3 = 66041
| EC_number2 = 203-595-7
| RTECS2 = CZ9450000
| UNII2 = 4S46QL2WFU
| UNII2_Ref = {{fdacite|correct|FDA}}
| EC_number = 215-325-5
| RTECS = CZ9370000
| UNNumber = 3532 3534
| UNII = IZ715T4SBU
| UNII_Ref = {{fdacite|correct|FDA}}
| EC_number3 = 203-266-8
| UNII3 = QN8RGZ4ML2
| UNII3_Ref = {{fdacite|correct|FDA}}
| SMILES = C=CC1=CC=CC=C1C=C
| SMILES2 = C=CC1=CC(=CC=C1)C=C
| InChI3=1S/C10H10/c1-3-9-5-7-10(4-2)8-6-9/h3-8H,1-2H2
| InChIKey3 = WEERVPDNCOGWJF-UHFFFAOYSA-N
| SMILES3 = C=CC1=CC=C(C=C1)C=C
}}
| Section2 = {{Chembox Properties
| C =10 | H=10
| MeltingPtC = -66.9 to -52
| BoilingPtC = 195
| Solvent = other solvents
| SolubleOther = Soluble in ethanol and ether
| Appearance = pale, straw-colored liquid
| VaporPressure = 0.7 mmHg (20°C)
| Density = 0.914 g/mL
}}
| Section7 = {{Chembox Hazards
| FlashPtC = 76
| PEL = none{{PGCH|0248}}
}}
}}
Divinylbenzene (DVB) is an organic compound with the chemical formula {{chem2|C6H4(CH\dCH2)2}} and structure {{chem2|H2C\dCH\sC6H4\sHC\dCH2}} (a benzene ring with two vinyl groups as substituents). It is related to styrene (vinylbenzene, {{chem2|C6H5\sCH\dCH2}}) by the addition of a second vinyl group.CRC Handbook of Chemistry and Physics 65Th Ed. 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.{{Cite book|title=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}}
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.
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.