Divinylbenzene

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Divinylbenzene
Divinylbenzene (structural diagram).png
Ball-and-stick model of m-Divinylbenzene M-Divinylbenzene-3D-balls.png
Ball-and-stick model of m-Divinylbenzene
Ball-and-stick model of p-Divinylbenzene P-Divinylbenzene-3D-balls.png
Ball-and-stick model of p-Divinylbenzene
Names
Other names
Diethylene benzene, DVB, Vinylstyrene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.932 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 215-325-5
  • m-:203-595-7
  • p-:203-266-8
PubChem CID
RTECS number
  • CZ9370000
  • m-:CZ9450000
UNII
UN number 1993
  • p-:InChI=1S/C10H10/c1-3-9-5-7-10(4-2)8-6-9/h3-8H,1-2H2
    Key: WEERVPDNCOGWJF-UHFFFAOYSA-N
  • C=CC1=CC=CC=C1C=C
  • m-:C=CC1=CC(=CC=C1)C=C
  • p-:C=CC1=CC=C(C=C1)C=C
Properties
C10H10
Molar mass 130.190 g·mol−1
Appearancepale, straw-colored liquid [1]
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)
0.005% (20°C) [1]
Solubility in other solventsSoluble in ethanol and ether
Vapor pressure 0.7 mmHg (20°C) [1]
Hazards
Flash point 76 °C (169 °F; 349 K)
Explosive limits 1.1%-6.2% [1]
NIOSH (US health exposure limits):
PEL (Permissible)
none [1]
REL (Recommended)
TWA 10 ppm (50 mg/m3) [1]
IDLH (Immediate danger)
N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

Contents

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

These compounds are systematically called diethenylbenzene, although this nomenclature is rarely encountered.

Related Research Articles

<span class="mw-page-title-main">Styrene</span> Chemical compound

Styrene is an organic compound with the chemical formula C6H5CH=CH2. Its structure consists of a vinyl group as substituent on benzene. Styrene a colorless, oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concentrations have a less pleasant odor. Styrene is the precursor to polystyrene and several copolymers, and is typically made from benzene for this purpose. Approximately 25 million tonnes of styrene were produced in 2010, increasing to around 35 million tonnes by 2018.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

<span class="mw-page-title-main">Butadiene</span> Chemical compound

1,3-Butadiene is the organic compound with the formula CH2=CH-CH=CH2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two vinyl groups. It is the simplest conjugated diene.

<span class="mw-page-title-main">Dicarbonyl</span> Molecule containing two adjacent C=O groups

In organic chemistry, a dicarbonyl is a molecule containing two carbonyl groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.

A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.

In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At its simplest, it is useful way of converting alkanes, which are relatively inert and thus low-valued, to olefins, which are reactive and thus more valuable. Alkenes are precursors to aldehydes, alcohols, polymers, and aromatics. As a problematic reaction, the fouling and inactivation of many catalysts arises via coking, which is the dehydrogenative polymerization of organic substrates.

Arynes and benzynes are highly reactive species derived from an aromatic ring by removal of two substituents. Arynes are examples of didehydroarenes, although 1,3- and 1,4-didehydroarenes are also known. Arynes are examples of strained alkynes.

In organic chemistry, hydrocyanation is a process for conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst. This conversion is conducted on an industrial scale for the production of precursors to nylon.

In polymer chemistry, a structural unit is a building block of a polymer chain. It is the result of a monomer which has been polymerized into a long chain.

<span class="mw-page-title-main">Vinylacetylene</span> Chemical compound

Vinylacetylene is the organic compound with the formula C4H4. The colourless gas was once used in the polymer industry. It is composed of both alkyne and alkene groups and is the simplest enyne.

<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.

<span class="mw-page-title-main">1,4-Benzoquinone</span> Chemical compound

1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

<span class="mw-page-title-main">1,4-Dihydropyridine</span> Chemical compound

1,4-Dihydropyridine (DHP) is an organic compound with the formula CH2(CH=CH)2NH. The parent compound is uncommon, but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors NADH and NADPH are derivatives of 1,4-dihydropyridine. 1,4-Dihydropyridine-based drugs are L-type calcium channel blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.

<span class="mw-page-title-main">1,2-Dichlorobenzene</span> Chemical compound

1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an organic compound with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.

α-Methylstyrene (AMS) is an organic compound with the formula C6H5C(CH3)=CH2. It is a colorless oil.

<span class="mw-page-title-main">Xylylene</span>

In organic chemistry, a xylylene (sometimes quinone-dimethide) is any of the constitutional isomers having the formula C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms by CH2 groups. ortho- and para-xylylene are best known, although neither is stable in solid or liquid form. The meta form is a diradical. Certain substituted derivatives of xylylenes are however highly stable, such as tetracyanoquinodimethane and the xylylene dichlorides.

In organic chemistry, transalkylation is a chemical reaction involving the transfer of an alkyl group from one organic compound to another. The reaction is used for the transfer of methyl and ethyl groups between benzene rings. This is of particular value in the petrochemical industry to manufacture p-xylene, styrene, and other aromatic compounds. Motivation for using transalkylation reactions is based on a difference in production and demand for benzene, toluene, and xylenes. Transalkylation can convert toluene, which is overproduced, into benzene and xylene, which are under-produced. Zeolites are often used as catalysts in transalkylation reactions.

<span class="mw-page-title-main">Diethylbenzenes</span> Chemical compound

Diethylbenzene (DEB) refers to any of three isomers with the formula C6H4(C2H5)2. Each consists of a benzene ring and two ethyl substituents. The meta and para have the greater commercial significance. All are colorless liquids.

C<sub>4</sub>-Benzenes Index of articles associated with the same name

The C4-benzenes are a class of organic aromatic compounds which contain a benzene ring and four other carbon atoms. There are three tetramethylbenzenes, six dimethylethylbenzenes, three diethylbenzenes, three isopropylmethylbenzenes, three n-propylmethylbenzenes and four butylbenzenes. The saturated compounds have formula C10H14 and molecular weight 134.22 g/mol. C4-benzenes are found in petroleum. Petrol (gasoline) can contain 5-8% C4-benzenes.

The chemical compound xylylene dichloride (C6H4(CH2Cl)2) is a white to light yellow sandlike solid. This compound can be classified as a benzyl halide. Xylylene dichloride is used as a vulcanizing agent to harden rubbers. It catalyzes the crosslinking of phenolic resins.

References

  1. 1 2 3 4 5 6 7 NIOSH Pocket Guide to Chemical Hazards. "#0248". National Institute for Occupational Safety and Health (NIOSH).
  2. CRC Handbook of Chemistry and Physics 65Th Ed.
  3. 1 2 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.