1.2- Dichloroethane, reaction with oxygen

Oxychlorination of Ethylene to Dichloroethane. Ethylene (qv) is converted to dichloroethane in very high yield in fixed-bed, multitubular reactors and fluid-bed reactors by reaction with oxygen and hydrogen chloride over potassium-promoted copper(II) chloride supported on high surface area, porous alumina (84) ... 

Epoxidation of olefins over Mo containing Y zeolites was studied by Lunsford et al. [86-90]. Molybdenum introduced in ultrastable Y zeolite through reaction with Mo(C0)g or M0CI5, shows a high initial activity for epoxidation of propylene with t-butyl hydroperoxide as oxidant and 1,2-dichloroethane as solvent [88]. The reaction is proposed to proceed via the formation of a Mo +-t-butyl hydroperoxide complex and subsequent oxygen transfer from the complex to propylene. The catalyst suffers however from fast deactivation caused by intrazeolitic polymerization of propylene oxide and resulting blocking of the active sites. 

Oxychlorination of Ethylene or Dichloroethane. Ethylene or dichloroethane can be chlorinated to a mixture of tetrachoroethylene and trichloroethylene in the presence of oxygen and catalysts. The reaction is carried out in a fluidized-bed reactor at 425°C and 138—207 kPa (20—30 psi). The most common catalysts ate mixtures of potassium and cupric chlorides. Conversion to chlotocatbons ranges from 85—90%, with 10—15% lost as carbon monoxide and carbon dioxide (24). Temperature control is critical. Below 425°C, tetrachloroethane becomes the dominant product, 57.3 wt % of cmde product at 330°C (30). Above 480°C, excessive burning and decomposition reactions occur. Product ratios can be controlled but less readily than in the chlorination process. Reaction vessels must be constmcted of corrosion-resistant alloys. 

Poly (vinyl chloride) prepared by the polymerisation of vinyl chloride. Vinyl chloride is a gas which is prepared by the reaction of ethylene with HC1 and oxygen to yield 1, 2-dichloroethane. The compound is then pyrolysed to yield vinyl chloride and HC1. 

The basic properties of the oxygen atoms in the nitrate ion seem to contribute to the formation of covalent nitrates, such as copper(II)-nitrate 31), as demonstrated by the reaction of the nitrate ion with boron(III) fluoride in dichloroethane 28) ... 

The reactions of ethyl hippurate 352 with l,2-diimidoyl-l,2-dichloroethanes 353 afforded 6-imino-6//-l,3-oxazines 354 by regioselective cyclization via the carbon and oxygen atoms of the dianion formed by the dilithiation of 352... 

In case of atomic oxygen reactions the formation of formaldehyde was found to be characteristic for all compounds studied (naturally except NH3 and CO). As a rule, but not always, the main reaction is the formation of formaldehyde. For example, for dichloroethane the reaction proceeds with scission of the carbon bond, but CH2O does not appear to be the main reaction product. As the dichloroethane molecule contains chlorine, the main product will be HC1. The formation of a... 

The first addition step—specifically, the direct catalytic chlorination of ethylene [Eq. (6.40)]—is almost always conducted in the liquid phase.188-190 272 273 1,2-Dichloroethane is used as solvent with ferric chloride, an efficient and selective catalyst. Ionic addition predominates at temperatures of 50-70°C. The conversion is usually 100% with 1,2-dichloroethane selectivity higher than 99%. The primary byproduct is 1,1,2-trichloroethane, believed to be formed by subsequent radical chlorination of 1,2-dichloroethane. A low amount of oxygen (below 1%), therefore, is added to the chlorine feed to suppress radical side reactions. 

The influence of solvents was extensively studied [38, 40b, 42], with reactions shown capable of being performed in neat, or, virtually in any polar medium. Whilst high dielectric constant oxygenated solvents such as tetrahydrofuran (THF), 1,4-dioxane, acetone (Et20), dimethyl sulfoxide (DMSO), and dimethyl-formamide (DMF) are used in non-asymmetric MBH reactions, dichloroethane (CH2C12) or acetonitrile are preferred for asymmetric transformations. MBH re-... 

Oxychlorination of hydrocarbons refers to a chemical reaction in which oxygen and hydrogen chloride react with a hydrocarbon in the vapor phase over a supported copper chloride catalyst to produce a chlorinated hydrocarbon and water. The oxychlorination of ethylene to produce 1, 2-dichloroethane (commonly, ethylene dichloride (EDC)) is of the greatest commercial importance. EDC is the precurser for vinyl chloride monomer, which when polymerized to polyvinyl chloride (PVC), becomes one of the most conunonly used commercial plastics. The overall oxychlorination reaction of ethane is given by... 

---