Ethyl benzene preparation

Note. Hydrocarbons such as ethyl-benzene can also be prepared by the Clemmensen reduction of the corresponding ketone. This is exemplified by the reduction of methylacetophenone (p. 290)]. 

Ethyl Benzene.h lttig s reaction, so-called fiom its (liscoveiei, is analogous to the synthetical method cin[iloycd by Wurt/ foi the prepar.ition of the aliphatic hydrocaibons, as in the foiiiiation of butane from ethyl bromide,... 

There is obtained from 4-[)3-[5-methyl-isoxazolyl-(3)-carboxamido]-ethyl]-benzene-sulfonamide (prepared from 5-methyl-isoxazole-(3)-carboxylic acid chloride and 4-()3-aminoethyl)-benzene-sulfonamide hydrochloride, MP 213° to 214°C in pyridine) and chloroformic acid methyl ester, in a yield of 69%, the compound N-[ [-4-[)3-[5-methyl-isoxazolyl-(3)-carbox-amido] -ethyl] ] -benzene-sulfonyl] ] -methyl-urethane in the form of colorless crystals of MP 173°C. 

To prepare multifunctionalized symmetric organosilicon compounds by the polyalkylation of benzene. (2-chloroethyi)trichlorosilane and (3-chloropropyl)tri-chlorosilane were reacted with benzene. Polyalkylations of benzene with (2-chloroethyl)silane and (3-chloropropyl)silane were carried out in the presence of aluminum chloride catalyst at a reaction temperature of 80 C. The reaction of benzene with excess (2-chloroethyI )trichlorosilanes afforded pcralkylated product, hexakis(2-(trichlorosilyl)ethyl)benzene in good yield (70%). ... 

The procedure described is essentially that of Ballard and Dehn.1 Stilbene has also been prepared by reduction of desoxy-benzoin,20 benzaldehyde,23 and benzil 2o-2c by dehydrogenation of ethyl benzene,30 toluene,30- 33- 3, and bibenzyl 33-3alkaline reduction of phenylnitromethane,40 phenylnitroacetonitrile,40 and desoxybenzoin 43 by distillation of benzyl sulfone,50 benzyl sulfide,60-63 calcium cinnamate,5 cinnamic acid,5d phenyl cinna-mate,6e-6/ and diphenyl fumarate ie by dehydrohalogenation of a,a -dichlorobibenzyl60 and benzyl chloride 63 by dehalogenation of a,a,c/,a -tetrachlorobibenzyl70 and benzal chloride 73 by the coupling of cinnamic acid and phenyldiazonium chloride 8 by de-... 

Another related process to prepare propylene oxide uses ethyl benzene as the peroxidizable species, and it produces a coproduct that is even more valuable than isobutylene. This process will be left for a homework problem. 

When sodium methylate or ethylate was prepared by direct reaction of sodium with an excess of alcohols and the resulting mixture was used as a dispersion in benzene to reduce aromatic nitro compounds, yields of azoxy compounds were quite low. With the higher alcohols, substantial production of azoxy compounds was observed. However, the reduction product mixture usually contained a 40 % yield of amino compounds. In a few examples, where benzyl alcohol was used to prepare sodium benzylate, only azoxy products and no amino by-products were formed. The scope of this preparation requires further study. 

This alkylation reaction is of great importance in the preparation of ethyl benzene, C6H5CH2CH3, because it can be dehydrogenated to produce styrene, C6H5CH=CH2. Styrene is polymerized to produce the enormous amounts of polystyrene and Styrofoam that are fashioned into a large number of familiar objects. 

The catalyst was prepared by treating a 37.33% solution of bis[2-(2-ethoxyethoxy)-ethanolato-(9,(9, (9"] barium dissolved in ethyl benzene with 50% tri-n-octyl aluminum in hexane so that the aluminum/barium ratio was 4 1, respectively. This mixture was then treated with sufficient 15% n-butyl lithium so that the lithium/barium ratio was 3 1, respectively. The catalyst was used immediately. 

TABLE 1. Physical properties of copolymers prepared by bulk polymerization using bis[2-(2-ethoxyethoxy)-ethanolato-0,0, 0"] barium, ethyl benzene, and tri-n-octyl aluminum as the high trans catalyst mixture. 

Preparative Methods the title compound can be prepared by reaction of (R)-2-[l-(dimethylamino)ethyl]phenyllithium with elemental sulfur (eq 1). A solution of pure (R)-2-[l-(dimethyl-amino)ethyl]phenyllithium in THF is slowly added at —50°C to a suspension of a stoichiometric amount of freshly sublimed sulfur. The solution is warmed to room temperature and quenched with an equimolar amount of a 10 M aqueous HCl solution. All volatiles are evaporated at reduced pressure and the residue is sublimed at 120 °C in vacuo (0.1 mmHg). The nitrogen-functionalized derivatives (R)-2-[l-(l-pyrrolidinyl) ethyljbenzenethiol and (R)-2-[l-(l-piperidinyl)ethyl]benzen-ethioP may be prepared in a similar way. It should be noted that reaction with MesSiCl instead of HCl after the sulfur insertion reaction affords the corresponding trimethylsilyl thio ether, which also is a valuable catalyst precursor. ... 

This is prepared similarly to tri-p-tolylarsine, the jp-bromotoluene being replaced by p-bromo-ethyl benzene. It melts at 78° C., is readily soluble in etlier, sparingly soluble in alcohol, and its mercurichloride melts at 182° C. 

The ethyl bromide thus obtained is contaminated with a small amount of ether. If it be desired to prevent this, the well-cooled crude ethyl bromide, contained in a flask surrounded by a freezing mixture of ice and salt, is treated, before drying with calcium chloride, with concentrated sulphuric acid, added drop by drop and with frequent shaking, until it separates out in a layer under the ethyl bromide. The acid containing the dissolved ether is then run off (in a separating funnel) from the ethyl bromide, which is shaken up several times with ice water, dried with calcium chloride, and redistilled as before. For the preparation of ethyl benzene (which see) the ethyl bromide thus purified cannot be used. 

Suppose it were possible to operate an ethyl benzene-dehydrogenation reactor under approximately isothermal conditions. If the temperature is 650°C, prepare a curve for conversion vs catalyst-bed depth which extends to the... 

Merrill and Unruh 35> described the preparation of azidophthalate esters of poly (vinyl alcohol). They found that the reaction of a nitrene with poly(vinyl toluene) was parallel to that of ethyl benzene in that side-chain hydrogen atom abstraction took place. -Carboxyphenylazide gave p, p -dicarboxyazobenzene and nitrogen on irradiation in the crystalline form 3S>. 

Sulfonal — Diethylsulfondimethylmetliane — qh / vIo c h . —is obtained by the oxidation of ethyl-mercaptol, prepared as above described, by potassium permanganate. It crystallizes in thick, colorless prisms, dilBcultly soluble in cold water or alcohol, readily soluble in hot water or alcohol, and in ether, benzene and chloroform. It fuses at 130"-131 (366°-267°.8 P.), and boils at 300° (572° F.), suffering partial decomposition. It dissolves in concentrated HjSOi, and is decomposed by the acid when heated, but may be precipitated from the cold solution unchanged bydilution with HjO. Nitric acid does not affect it, even when heated. It is not attacked bj Br, by caustic alkalies or by nascent H. 

A year later, MCM-41 was used to prepare a Cr(salpr)MCM-41 (salpr=Ar,Ai -bis(3-salicylidenaminopropyl)amine) catalyst for the benzylic oxidation of allqrl aromatics. Masteri-Farahani et al. used a chloropropyl-modified MCM-41 material that was mixed with a [Cr(salpr)(H20)Cl] complex to produce their chromium catalyst. Using tert-bulylhydroperoxide (TBHP) as an oxidant, a mixture of the catalyst and substrate in solvent (chloroform or the substrate itself) was reacted for 7 h to afford the oxidised product. The substrates tested were toluene and ethyl benzene, which showed high selectivity towards the oxidised product benzaldehyde or acetophenone, respectively. 

In the laboratory, styrene can be prepared by the decarboxylation of cinnamic acid, as shown in Reaction 1, using dry distillation. However, styrene is produced commercially from ethylene and benzene, two basic ingiedienis of the petrochemical industry. With electrophilic addition of ethylene to benzene, a mixture of ethyl benzene and diethylbenzene is obtained as own in Reaction 2. The dehydrogenation of these benzene derivatives produces slyrene and divinylbenzene, respectively (Reaction 3). A detailed synthesis of styrene is described by Berthelot et al (6). As mentioned earlier, styrene is an important monomer in many industrial polymers. Additionally, divinylbenzene which is produced as a by-product is an effective crosslinker for ion-exchange resins, polystyrene-based supported reagents and catalysts, and low profile additive in a number of liquid molding resin systems. 

A series of mono- and di-substituted carbonyl complexes of Ni(CO), Fe(CO)g, Cr(CO)g, Mo(CO)g and W(CO) with la have been prepared by refluxing stoichiometric quantities of ligand and metal carbonyl under nitrogen flush in ethyl benzene. The colorless diamagnetic complexes are soluble in acetone and chloroform. It is significant that the IR carbonyl stretching frequencies occur at relatively high values (ca, 2000 cm ). The... 

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