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ethylbenzene

Product name ethylbenzene
GOST 9385-77
CAS 100-41-4

Ethylbenzene C6H5CH2CH3 is a clear, colorless, flammable liquid with a benzene-like odor. It is fully miscible with benzene, toluene, hexane, petroleum ether, chloroform, carbon tetrachloride and many other organic solvents. It is almost insoluble in water - 0.014% wt at 15°C.

Ethylbenzene possesses chemical properties of aromatic compounds. It reacts with chlorine or bromine in gaseous phase at higher temperature or under light to form 1-halogenethyl and 2-halogenethylbenzenes. The reaction mechanism has a free-radical nature. The interaction with halogens in liquid phase occurs under more soft conditions and leads to ring-substituted adducts (the set of ortho- and para- derivatives). The nitration of ethylbenzene results in mono-, di- and tri- substituted derivatives.

The oxidation of ethylbenzene may result in different product depending on the nature of oxidizing agent and reaction conditions:

ethylbenzene oxidation


Thus, reaction with chromium(VI) oxide CrO3 or diluted nitric acid leads to acetophenone and benzoic acid. Treatment of ethylbenzene with sodium dichromate Na2Cr2O7 in autoclave at 250°C during 1 hour gives phenylacetic acid sodium salt with 89% yield. Liquid phase oxidation of ethylbenzene in the presence of magnesium acetate results in α-phenylethanol. Oxidation with oxygen of air at 130°C gives hydroperoxide. This reaction is used in chemical industry for propylene oxide and styrene manufacturing in SM/PO process.

Ethylbenzene is dehydrogenated at 580-650°C in vacuum in the presence of catalyst (Fe2O3 promoted with CrO3, V2O5 or KOH) to obtain styrene. This process is reversible and endothermic (ΔH=124KJ/mol).

C6H5CH2CH2 ⇄ C6H5CH=CH2 + H2

Production.

Although often present in small amounts in crude oil and in products of oil fractions reforming, ethylbenzene is produced in bulk quantities by alkylation of benzene with ethylene. This reaction is conducted at 450-500°C and is catalyzed by acidic catalysts such as aluminum chloride AlCl3:

C6H6 + CH2=CH2 → C6H5CH2CH3

By-products of this reaction are ortho-, meta-, para- diethylbenzenes and small amount of triethylbenzenes.

Uses.

  • Main application of ethylbenzene in industry is as styrene precursor;
  • Some amounts are used in propylene oxide making via SM/PO process;
  • in α-phenylethanol synthesis via SM/PO process. This compound is used in perfumery;
  • as a non-polar inert solvent, e.g. in paints;

Manufacturer(s) JSC "Nizhnekamskneftekhim" Inc.
SIBUR-CHEMPROM
Chemical structure of ethylbenzene

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