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{{short description|1=Organic compound, C₆H₄(CH=CH₂)₂}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 299525301 |
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| Watchedfields = changed |
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| Name = Divinylbenzene |
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| verifiedrevid = 430950526 |
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| ImageFile = DVB.png |
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| Name = Divinylbenzene |
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| ImageSize = 200px |
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| ImageFile = Divinylbenzene (structural diagram).png |
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| ImageName = Skeletal formulae of both isomers |
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| ImageName = Skeletal formulae of both isomers |
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| ImageFileL1 = M-Divinylbenzene-3D-balls.png |
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| ImageSize = 220px |
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| ImageSizeL1 = 105 |
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| ImageFileL1 = M-Divinylbenzene-3D-balls.png |
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| ImageNameL1 = Ball-and-stick model of m-Divinylbenzene |
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| ImageNameL1 = Ball-and-stick model of m-Divinylbenzene |
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| ImageFileR1 = P-Divinylbenzene-3D-balls.png |
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| ImageFileR1 = P-Divinylbenzene-3D-balls.png |
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| ImageSizeR1 = 120 |
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| ImageNameR1 = Ball-and-stick model of p-Divinylbenzene |
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| ImageNameR1 = Ball-and-stick model of p-Divinylbenzene |
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| OtherNames = Diethylene benzene, DVB, Vinylstyrene |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| index2_label = ''m''- |
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| index3_label = ''p''- |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 1321-74-0 |
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| CASNo = 1321-74-0 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| EINECS = 215-325-5 |
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| CASNo2 = 108-57-6 |
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| CASNo3_Ref = {{cascite|correct|CAS}} |
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| CASNo3 = 105-06-6 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 60033 |
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| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID2 = 7653 |
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| ChemSpiderID3_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID3 = 59432 |
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| PubChem = 66666 |
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| PubChem2 = 7941 |
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| PubChem3 = 66041 |
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| EC_number2 = 203-595-7 |
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| RTECS2 = CZ9450000 |
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| UNII2 = 4S46QL2WFU |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| EC_number = 215-325-5 |
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| RTECS = CZ9370000 |
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| UNNumber = 3532 3534 |
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| UNII = IZ715T4SBU |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EC_number3 = 203-266-8 |
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| UNII3 = QN8RGZ4ML2 |
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| UNII3_Ref = {{fdacite|correct|FDA}} |
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| SMILES = C=CC1=CC=CC=C1C=C |
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| SMILES2 = C=CC1=CC(=CC=C1)C=C |
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| InChI3=1S/C10H10/c1-3-9-5-7-10(4-2)8-6-9/h3-8H,1-2H2 |
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| InChIKey3 = WEERVPDNCOGWJF-UHFFFAOYSA-N |
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| SMILES3 = C=CC1=CC=C(C=C1)C=C |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=10 | H=10 |
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| C =10 | H=10 |
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| MeltingPt = -66.9 to -52°C |
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| MeltingPtC = -66.9 to -52 |
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| BoilingPt = 195°C |
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| BoilingPtC = 195 |
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| Solvent = other solvents |
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| Solvent = other solvents |
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| Solubility = Insoluble |
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| Solubility = 0.005% (20°C)<ref name=PGCH/> |
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| SolubleOther = Insoluble in ]<br /> Soluble in ] and ] |
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| SolubleOther = Soluble in ] and ] |
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| Appearance = pale, straw-colored liquid<ref name=PGCH/> |
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| VaporPressure = 0.7 mmHg (20°C)<ref name=PGCH/> |
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| Density = 0.914 g/mL |
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}} |
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| Section7 = {{Chembox Hazards |
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| Section7 = {{Chembox Hazards |
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| FlashPt = 76°C |
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| FlashPtC = 76 |
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| PEL = none<ref name=PGCH>{{PGCH|0248}}</ref> |
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| ExploLimits = 1.1%-6.2%<ref name=PGCH/> |
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| REL = TWA 10 ppm (50 mg/m<sup>3</sup>)<ref name=PGCH/> |
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| IDLH = N.D.<ref name=PGCH/> |
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'''Divinylbenzene (DVB)''' consists of a ] ring ] to two ] groups. It is related to ] (vinylbenzene) by the addition of a second vinyl group.<ref name=crc>] 65Th Ed.</ref> Divinylbenzene, as it is usually encountered, is a 2:1 mixture of m- and p-divinylbenzene, containing also the corresponding ethylvinylbenzene isomers. It is manufactured by the thermal ] of isomeric diethylbenzenes. Under synthesis conditions, o-divinylbenzene converts to ] and thus is not a component of the usual mixtures of DVB.<ref name=Ullmann>Denis H. James William M. Castor, “Styrene” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.</ref> |
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'''Divinylbenzene''' ('''DVB''') is an ] with the ] {{chem2|C6H4(CH\dCH2)2}} and ] {{chem2|H2C\dCH\sC6H4\sHC\dCH2}} (a ] ring with two ]s as ]). It is related to ] (vinylbenzene, {{chem2|C6H5\sCH\dCH2}}) by the addition of a second vinyl group.<ref name=crc>] 65Th Ed.</ref> It is a colorless liquid manufactured by the thermal ] of isomeric diethylbenzenes. Under synthesis conditions, ''o''-divinylbenzene converts to ] and thus is not a component of the usual mixtures of DVB.<ref name=Ullmann>{{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}}</ref> |
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==Production and use== |
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==Applications== |
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It is produced by dehydrogenation of ]: |
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When reacted together with styrene, divinylbenzene can be used as a reactive ] in ]s. Styrene and divinylbenzene react together to form the ] styrene-divinylbenzene, S-DVB or Sty-DVB. The resulting ]ed polymer is mainly used for the production of ].<ref name=Ullmann/> |
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: C<sub>6</sub>H<sub>4</sub>(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub> → C<sub>6</sub>H<sub>4</sub>(C<sub>2</sub>H<sub>3</sub>)<sub>2</sub> + 2 H<sub>2</sub> |
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Divinylbenzene is usually encountered as a 2:1 mixture of ''m''- and ''p''-divinylbenzene, containing also the corresponding isomers of ethylvinylbenzene. |
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Styrene and divinylbenzene react to form the ] styrene-divinylbenzene, S-DVB or Sty-DVB. The resulting ]ed polymer is mainly used for the production of ] and ]s for peptide synthesis.<ref name=Ullmann/> |
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Density is 0.914 g/mL |
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==Nomenclature== |
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==Nomenclature== |
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* ]: variously known as 1,2-diethenylbenzene, 1,2-divinylbenzene, ''o''-vinylstyrene, ''o''-divinylbenzene |
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''See also'': ]'' |
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* ]: known as 1,3-diethenylbenzene, 1,3-divinylbenzene, ''m''-vinylstyrene, ''m''-divinylbenzene |
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Divinylbenzene can exist in the form of 3 structural ]s that differ with respect to the positioning of the vinyl groups. |
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* ''Ortho'': variously known as 1,2-diethenylbenzene, 1,2-divinylbenzene, ''o''-vinylstyrene, ''o''-divinylbenzene |
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* ]: known as 1,4-diethenylbenzene, 1,4-divinylbenzene, ''p''-vinylstyrene, ''p''-divinylbenzene. |
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These compounds are ] called diethenylbenzene, although this nomenclature is rarely encountered. |
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* ''Meta'': known as 1,3-diethenylbenzene, 1,3-divinylbenzene, ''m''-vinylstyrene, ''m''-divinylbenzene |
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* ''Para'': known as 1,4-diethenylbenzene, 1,4-divinylbenzene, ''p''-vinylstyrene, ''p''-divinylbenzene. |
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These compounds are ] called as diethenylbenzene, although this nomenclature is rarely encountered. |
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==References== |
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==References== |
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{{Hydrocarbons}} |
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