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Divinylbenzene: Difference between revisions

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Revision as of 02:45, 26 May 2011 editZéroBot (talk | contribs)704,777 editsm r2.7.1) (robot Adding: fr:Divinylbenzène← Previous edit Latest revision as of 02:27, 10 January 2025 edit undoKappa winter 9 (talk | contribs)4 edits UN number according to CINS report and M.V. "MSC Flaminia " accident.Tag: Visual edit 
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{{short description|1=Organic compound, C₆H₄(CH=CH₂)₂}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 299525301
| Watchedfields = changed
| Name = Divinylbenzene
| verifiedrevid = 430950526
| ImageFile = DVB.png
| Name = Divinylbenzene
| ImageSize = 200px
| ImageFile = Divinylbenzene (structural diagram).png
| ImageName = Skeletal formulae of both isomers | ImageName = Skeletal formulae of both isomers
| ImageFileL1 = M-Divinylbenzene-3D-balls.png
| ImageSize = 220px
| ImageSizeL1 = 105
| ImageFileL1 = M-Divinylbenzene-3D-balls.png
| ImageNameL1 = Ball-and-stick model of m-Divinylbenzene | ImageNameL1 = Ball-and-stick model of m-Divinylbenzene
| ImageFileR1 = P-Divinylbenzene-3D-balls.png | ImageFileR1 = P-Divinylbenzene-3D-balls.png
| ImageSizeR1 = 120
| ImageNameR1 = Ball-and-stick model of p-Divinylbenzene | ImageNameR1 = Ball-and-stick model of p-Divinylbenzene
| OtherNames = Diethylene benzene, DVB, Vinylstyrene
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| index2_label = ''m''-
| index3_label = ''p''-
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1321-74-0 | CASNo = 1321-74-0
| CASNo2_Ref = {{cascite|correct|CAS}}
| EINECS = 215-325-5
| 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 | Section2 = {{Chembox Properties
| C=10 | H=10 | C =10 | H=10
| MeltingPt = -66.9 to -52°C | MeltingPtC = -66.9 to -52
| BoilingPt = 195°C | BoilingPtC = 195
| Solvent = other solvents | Solvent = other solvents
| Solubility = Insoluble | Solubility = 0.005% (20°C)<ref name=PGCH/>
| SolubleOther = Insoluble in ]<br /> Soluble in ] and ] | SolubleOther = Soluble in ] and ]
| Appearance = pale, straw-colored liquid<ref name=PGCH/>
| VaporPressure = 0.7 mmHg (20°C)<ref name=PGCH/>
| Density = 0.914 g/mL

}} }}
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
| FlashPt = 76°C | FlashPtC = 76
| PEL = none<ref name=PGCH>{{PGCH|0248}}</ref>
| ExploLimits = 1.1%-6.2%<ref name=PGCH/>
| REL = TWA 10 ppm (50 mg/m<sup>3</sup>)<ref name=PGCH/>
| IDLH = N.D.<ref name=PGCH/>
}} }}
}} }}


'''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> '''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>


==Production and use==
==Applications==
It is produced by dehydrogenation of ]:
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/>
: 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>
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 ] 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/>
Density is 0.914 g/mL


==Nomenclature== ==Nomenclature==
* ]: variously known as 1,2-diethenylbenzene, 1,2-divinylbenzene, ''o''-vinylstyrene, ''o''-divinylbenzene
''See also'': ]''
* ]: known as 1,3-diethenylbenzene, 1,3-divinylbenzene, ''m''-vinylstyrene, ''m''-divinylbenzene
Divinylbenzene can exist in the form of 3 structural ]s that differ with respect to the positioning of the vinyl groups.
* ''Ortho'': variously known as 1,2-diethenylbenzene, 1,2-divinylbenzene, ''o''-vinylstyrene, ''o''-divinylbenzene * ]: known as 1,4-diethenylbenzene, 1,4-divinylbenzene, ''p''-vinylstyrene, ''p''-divinylbenzene.
These compounds are ] called diethenylbenzene, although this nomenclature is rarely encountered.
* ''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 ] called as diethenylbenzene, although this nomenclature is rarely encountered.


==References== ==References==
<references/> <references/>


{{Hydrocarbons}}
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