Ethyl chloride ethylbenzene

In the presence of Eriedel-Crafts catalysts, gaseous ethyl chloride reacts with ben2ene at about 25°C to give ethylben2ene, three diethylben2enes, and other more complex compounds (12) (see Xylenes and ethylbenzene). Aromatic compounds can generally be ethylated by ethyl chloride in the presence of anhydrous aluminum chloride (see Eriedel-Crafts REACTIONS). Ethyl chloride combines directly with sulfur trioxide to give ethyl chlorosulfonate,... 

Addition. Addition reactions of ethylene have considerable importance and lead to the production of ethylene dichloride, ethylene dibromide, and ethyl chloride by halogenation—hydrohalogenation ethylbenzene, ethyltoluene, and aluminum alkyls by alkylation a-olefms by oligomerization ethanol by hydration and propionaldehyde by hydroformylation. 

Obtain samples of the following 11 organic liquids contained in individual small dropper bottles n-hexane (or other alkane), acetonitrile, methylene chloride, acetone, toluene, methanol, diethyl ether, ethyl acetate, ethylbenzene, ethanol, and chloroform. Then label each of the test tubes from step 1 with the names, or an abbreviation of the names, of these liquids. 

Ethyl sec-amyl ketone, see 5-Methyl-3-heptanone Ethylbenzol, see Ethylbenzene Ethyl butyl ketone, see 3-Heptanone Ethyl n-butyl ketone, see 3-Heptanone Ethyl carbinol, see 1-Propanol Ethyl cellosolve, see 2-Ethoxyethanol Ethyl chloride, see Chloroethane Ethylcyclopentan, see Ethylcyclopentane Ethyldimethylmethane, see 2-Methylbutane Ethylendiamine, see Ethylenediamine Ethylene aldehyde, see Acrolein Ethylene bromide, see Ethylene dibromide Ethylene bromide glycol dibromide, see Ethylene dibromide... 

Ethylbenzene under Benzene and Monosubstituted Benzene Hydrocarbons Ethyl Chloride Chloroethane under Saturated Alkyl Halides Ethyl Lactate Hydroxypropanoic Acid, Ethyl Ester under Esters Ethylene under Alkenes, Cyclic Alkenes, and Dienes... 

Even (hough there are few direct end-uses foe ethylene, it is probably the most important petrochemical feedstock, both in terms of quantities used and economic value. Ethylene is the feedstock for ethylene oxide, ethylbenzene, ethyl chloride, elhylene dichloride, ethyl alcohol, and polyethylene, most of which, in turn, are used to produce hundreds of other end-products. Most elhylene is produced by sleam cracking of ethane or propane. 

Ethylbenzene was the first petrochemical to be produced by petroleum refiners in large quantities. It is made by the alkylation of benzene by ethylene. Aluminum chloride promoted with ethyl chloride was originally the predominant catalyst used for the reaction, but solid phosphoric acid has been used more recently and is becoming more popular. Some of the newer fluoride-type catalysts are expected to become quite popular. 

Ethylbenzene is manufactured by the alkylation process from ethylene and benzene feeds. The catalyst employed has mostly been aluminum chloride with a small addition of ethyl chloride promoter. Normally, aluminum chloride is somewhat corrosive and causes relatively high maintenance on the equipment. 

Fittig and Tollens [27] obtained ethylbenzene by synthesis from chlorobenzene and ethyl chloride. At first they believed it was xylene (basing their view on its boiling point). However, the substance did not yield a crystalline product when nitrated, as in the case of xylene, but an oily one, from which they inferred that the ethylphenyl they had obtained was not xylene. 

Limitation 3 Because alkyl groups are activating substituents, the product of the Friedel-Crafts alkylation is more reactive than the starting material. Multiple alkylations are hard to avoid. This limitation can be severe. If we need to make ethylbenzene, we might try adding some A1C13 to a mixture of 1 mole of ethyl chloride and 1 mole of benzene. As some ethylbenzene is formed, however, it is activated, reacting even faster than benzene itself. The product is a mixture of some (ortho and para) diethylbenzenes, some triethylbenzenes, a small amount of ethylbenzene, and some leftover benzene. 

The problem of overalkylation can be minimized by using a large excess of benzene. For example, if 1 mole of ethyl chloride is used with 50 moles of benzene, the concentration of ethylbenzene is always low, and the electrophile is more likely to react with benzene than with ethylbenzene. Distillation separates the product from excess benzene. This is a common industrial approach, since a continuous distillation can recycle the unreacted benzene. 

Use Ethylbenzene catalyst, dyestuff intermediate, detergent alkylate, ethyl chloride, pharmaceuticals and organics (Friedel-Crafts catalyst), butyl rubber, petroleum refining, hydrocarbon resins, nucleating agent for titanium dioxide pigments. 

Friedel-Crafts reaction. A type of reaction involving anhydrous aluminum chloride and similar metallic halides as catalysts, discovered in 1877 by Charles Friedel, a French chemist (1832-1899), and James Mason Crafts, an American chemist (1830-1917), during joint research in France it has been developed since then for many important industrial uses, exemplified by the condensation of ethyl chloride and benzene to form ethylbenzene and the manufacture of acetophenone from acetyl chloride and benzene. The name is now applied to a wide variety of acid-catalyzed organic reactions. 

Benzene, (2-chloro-1,1-dimethylethyl)- (p-Chloro-a,a-dimethyl)ethylbenzene (p-Chloro-t-butyl)benzene (2-Chloro-1,1-dimethylethyl)benzene p,p-Dimethylphen-ethyl chloride EINECS 208-197-7 2-Methyl-2-phenyl-propyl chloride Neophyl chloride NSC 54159. Liquid bp = 223 , bpi8 = 105" very soluble in EtOH, EtzO, MezCO, CeHe. 

A continuous process for ethylbenzene is shown by Fig. 14-8. Anhydrous conditions must prevail hence the 99- - per cent purity benzene is pumped through an azeotropic drying colunm from which benzene with less than 30 ppm water is withdrawn. This benzene is mixed with recirculated catalyst complex and fresh catalyst (anhydrous Aids). The hydrogen chloride which serves as a promoter is furnished indirectly from the ethyl chloride previously mixed with the ethylene (90-95 mole per cent purity). 

Fig. 2. Annual anhydrous aluminum chloride market, 1984, 10 t/yr (10). H, Dyestuffs , ethylbenzene , ethyl chloride E...

Ammonium citrate tribasic Ammonium fluoborate Ammonium-12-molybdosilicate Ammonium phosphomolybdate Basic blue 9 Bromodichloromethane t-ButyIdimethylsilyl imidazole Chromium chloride (ous) Dimethyl acetamide Dimethyl formamide Ethoxydiglycol acetate Ethyl acetate Ethylbenzene Ethyl formate Ferric sulfate Formic acid Heptane Hexamethylenetetramine Isopropyl ether Methyl cyclohexane 2,7-Naphthalenediol ... 

First, Monsanto Chemical Co. developed an ethylbenzene process that used (C2H5)3—C6H4+Al2Cl7 as the catalyst (40-42). This compound is dissolved in the hydrocarbon phase in the cylindrical reactor. A mixture of ethylene and a small amount of promoter (HCl or ethyl chloride) is bubbled upward through the liquid phase in the reactor maintained at about 150-180°C. The molar ratios of benzene to ethylene are controlled at about 1.5-2.5 to minimize the production of overalkylated benzenes. The sparger design used to introduce ethylene is of importance to produce relatively small droplets of ethylene in the bottom portion of the reactor and to promote rapid transfer of ethylene to the liquid phase. High rates of the reaction occur since ethylene conversions are complete. 

As seen in the fifth example of Table 6.12, and in more detail in Scheme 6.85, when a cold solution of benzene (CeH ) is treated with chloroethane (ethyl chloride, CH3CH2CI) in the presence of a Lewis acid (such as aluminum trichloride, AICI3), phenylethane (ethylbenzene, C6H5CH2CH3) is formed. 

Scheme 6.85. A representation of the Friedel-Crafts reaction between chloroethane (ethyl chloride, CH3CH2CI) and benzene (CeHe) in the presence of aluminum trichloride (AICI3) to produce ethylbenzene (C6H5CH2CH3). A complex between chloroethane (CH3CH2CI) and aluminum trichloride (AICI3) is suggested as the species being attacked by the electron-rich aromatic ring.

In the first stage, a Friedel-Crafts reaction is carried out by treating benzene with ethylene in the liquid phase at 90—100°C at slightly above atmospheric pressure. The catalyst is aluminium chloride (with ethyl chloride as catalyst promoter). A molar excess of benzene is used to reduce the formation of poly ethylbenzenes the molar ratio of reactants is generally about 1 0.6. The reactants are fed continuously into the bottom of a reactor whilst crude product is removed from near the top. The product is cooled and allowed to separate into two layers the lower layer, which consists of an aluminium chloride-hydrocarbon complex, is removed and returned to the reactor. The remaining ethylbenzene is then separated by distillation from polyethylbenzenes and benzene, which are recycled. 

Ethylaniine Ethylbenzene Ethyl Butanoaie Ethyl Butanol 2-Ethyl-1-Butanol 2-Ethylbutyl Alcohol Ethyl Butyrate 2-Ethylcaproaldehyde Ethylcarbinol Ethyl Carbonate Ethyl Chloracetate Ethyl Chloride... 

Compound Name Ethoxylated Pentadecanol Ethoxylated Tetradecanol Ethoxylated Tetradecanol Ethoxylated Tridecanol Ethoxylated Tridecanol Ethoxy Triglycol Ethoxy Triglycol Ethyl Acetate N-Butyric Acid Ethyl Acetoacetate Ethyl Acrylate Ethyl Alcohol Acetaldehyde Ethylaluminum Dichloride Ethylaluminum Sesquichloride Ethylaniine Ethylbenzene Ethyl Butyrate Ethyl Butanol Ethyl Butanol Ethyl Butanol Ethyl Butyrate Ethylhexaldehyde N-Propyl Alcohol Diethyl Carbonate Ethyl Chloracetate Ethyl Chloride Ethyl Chloroacetate Ethyl Chloroformate Ethyl Chloroacetate Ethyl Chloroacetate Ethyl Phosphorodi-chloridate Ethyldichlorosilane Ethylene Ethylene Glycol Diacetate... 

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