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

| Solubility = 0.005% (20°C)

| 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}}

| ExploLimits = 1.1%-6.2%

| REL = TWA 10 ppm (50 mg/m3)

| IDLH = N.D.

}}

}}

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.

References