4-Vinylbenzyl chloride

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4-Vinylbenzyl chloride
4-vinylbenzyl chloride.svg
Names
Preferred IUPAC name
1-(Chloromethyl)-4-ethenylbenzene
Other names
1-(Chloromethyl)-4-vinylbenzene
α-Chloromethylstyrene
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 250-005-9
PubChem CID
UNII
  • InChI=1S/C9H9Cl/c1-2-8-3-5-9(7-10)6-4-8/h2-6H,1,7H2
    Key: ZRZHXNCATOYMJH-UHFFFAOYSA-N
  • C=Cc1ccc(cc1)CCl
Properties
C9H9Cl
Molar mass 152.62
Appearancecolorless liquid
Density 1.083
Boiling point 229 °C (444 °F; 502 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
alkylating agent
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

4-Vinylbenzyl chloride is an organic compound with the formula ClCH2C6H4CH=CH2. It is a bifunctional molecule, featuring both vinyl and a benzylic chloride functional groups. It is a colorless liquid that is typically stored with a stabilizer to suppress polymerization.

In combination with styrene, vinylbenzyl chloride is used as a comonomer in the production of chloromethylated polystyrene. [1] It is produced by the chlorination of vinyltoluene. Often vinyltoluene consists of a mixture of 3- and 4-vinyl isomers, in which case the vinylbenzyl chloride will also be produced as a mixture of isomers. [2]

Related Research Articles

Alkene Type of chemical compound

In chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.

In chemistry, a monomer is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization.

Vinyl group Organic chemistry functional group

In chemistry, vinyl or ethenyl (abbreviated as Vi) is the functional group with the formula H-C=CH2. It is the ethylene (IUPAC ethene) molecule (H2C=CH2) with one fewer hydrogen atom. The name is also used for any compound containing that group, namely R−CH=CH2 where R is any other group of atoms.

Petrochemical Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

Vinyl chloride is an organochloride with the formula H2C=CHCl that is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC). About 13 billion kilograms are produced annually. VCM is among the top twenty largest petrochemicals (petroleum-derived chemicals) in world production. The United States currently remains the largest VCM manufacturing region because of its low-production-cost position in chlorine and ethylene raw materials. China is also a large manufacturer and one of the largest consumers of VCM. Vinyl chloride is a gas with a sweet odor. It is highly toxic, flammable, and carcinogenic. It can be formed in the environment when soil organisms break down chlorinated solvents. Vinyl chloride that is released by industries or formed by the breakdown of other chlorinated chemicals can enter the air and drinking water supplies. Vinyl chloride is a common contaminant found near landfills. In the past VCM was used as a refrigerant.

1,3-Butadiene is the organic compound with the formula (CH2=CH)2. 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.

Dicyclopentadiene Chemical compound

Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12. At room temperature, it is a white brittle wax, although lower purity samples can be straw coloured liquids. The pure material smells somewhat of soy wax or camphor, with less pure samples possessing a stronger acrid odor. Its energy density is 10,975 Wh/l. Dicyclopentadiene is a co-produced in large quantities in the steam cracking of naphtha and gas oils to ethylene. The major use is in resins, particularly, unsaturated polyester resins. It is also used in inks, adhesives, and paints.

<i>n</i>-Butyllithium Organolithium reagent

n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry.

Anionic addition polymerization is a form of chain-growth polymerization or addition polymerization that involves the polymerization of monomers initiated with anions. The type of reaction has many manifestations, but traditionally vinyl monomers are used. Often anionic polymerization involves living polymerizations, which allows control of structure and composition.

Vinyl polymers are a group of polymers derived from substituted vinyl monomers of the type CH2=CHR. Their backbone is an extended alkane chain ...-CH2-CHR-CH2-CHR-..). In popular usage, "vinyl" refers only to polyvinyl chloride (PVC).

1,2-Dichloroethene, commonly called 1,2-dichloroethylene or 1,2-DCE, is an organochloride with the molecular formula C2H2Cl2. It is a highly flammable, colorless liquid with a sharp, harsh odor. It can exist as either of two geometric isomers, cis-1,2-dichloroethene or trans-1,2-dichloroethene, but is often used as a mixture of the two. They have modest solubility in water. These compounds have few industrial applications, although they are fundamental given their simple stoichiometries.

Methyl vinyl ketone Chemical compound

Methyl vinyl ketone (MVK, IUPAC name: butenone) is the organic compound with the formula CH3C(O)CH=CH2. It is a reactive compound classified as an enone, in fact the simplest example thereof. It is a colorless, flammable, highly toxic liquid with a pungent odor. It is soluble in water and polar organic solvents. It is a useful intermediate in the synthesis of other compounds.

Divinylbenzene Chemical compound

Divinylbenzene (DVB) consists of a benzene ring bonded to two vinyl groups. It is related to styrene (vinylbenzene) by the addition of a second vinyl group. 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.

In polymer chemistry, a repeat unit or repeating unit is a part of a polymer whose repetition would produce the complete polymer chain by linking the repeat units together successively along the chain, like the beads of a necklace.

Polyvinyl toluene

Polyvinyltoluene is a synthetic polymer of alkylbenzenes with a linear formula [CH2CH(C6H4CH3)]n. Commercial vinyl toluene is a mixture of methyl styrene isomers

Living cationic polymerization is a living polymerization technique involving cationic propagating species. It enables the synthesis of very well defined polymers and of polymers with unusual architecture such as star polymers and block copolymers and living cationic polymerization is therefore as such of commercial and academic interest.

2-Vinylpyridine Chemical compound

2-Vinylpyridine is an organic compound with the formula CH2CHC5H4N. It is a derivative of pyridine with a vinyl group in the 2-position, next to the nitrogen. It is a colorless liquid, although samples are often brown. It is used industrially as a precursor to specialty polymers and as an intermediate in the chemical, pharmaceutical, dye, and photo industries. Vinylpyridine is sensitive to polymerization. It may be stabilized with a free radical inhibitor such as tert-butylcatechol. Owing to its tendency to polymerize, samples are typically refrigerated.

Vinylsulfonic acid Chemical compound

Vinylsulfonic acid is the organosulfur compound with the chemical formula CH2=CHSO3H. It is the simplest unsaturated sulfonic acid. The C=C double bond is a site of high reactivity. Polymerization gives polyvinylsulfonic acid, especially when used as a comonomer with functionalized vinyl and (meth)acrylic acid compounds. It is a colorless, water-soluble liquid, although commercial samples can appear yellow or even red.

4-Vinyltoluene Chemical compound

4-Vinyltoluene is an organic compound with the formula CH3C6H4CH=CH2. It is derivative of styrene and is used as a comonomer in the production of specialized polystyrenes. It is produced by the dehydrogenation of 4-ethyltoluene.

4-Ethyltoluene Chemical compound

4-Ethyltoluene is an organic compound with the formula CH3C6H4C2H5. It is one of three isomers of ethyltoluene, the other two isomers being 3-ethyltoluene and 2-ethyltoluene. All are colorless liquids and all are used for the production of specialty polystyrenes.

References

  1. Montheard, Jean Pierre; Jegat, Corinne; Camps, Marcel "Vinylbenzylchloride (chloromethylstyrene), polymers, and copolymers. Recent reactions and applications" Journal of Macromolecular Science, Reviews in Macromolecular Chemistry and Physics 1999, volume C39, pp. 135-174.
  2. Denis H. James; William M. Castor (2007), "Styrene", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 1, doi:10.1002/14356007.a25_329.pub2, ISBN   978-3527306732