Reaction ethylene chlorination

Then, as described in U.S. Patent 2,55416, the 2-acetylamido-5-mercapto-1,3,4-thiadiazole is converted to the sulfonyl chloride by passing chlorine gas into a cooled (5°-10°C) solution in 33% acetic acid (66 parts to 4 parts of mercapto compound) used as a reaction medium. Chlorine treatment is continued for two hours. The crude product can be dried and purified by recrystallization from ethylene chloride. The pure compound is a white crystalline solid, MP l94°C,with decomposition, when heated rapidly. The crude damp sulfonyl chloride is converted to the sulfonamide by addition to a large excess of liquid ammonia. The product is purified by recrystallization from water. The pure compound is a white, crystalline solid, MP 259°C, with decomposition. The yield of sulfonamide was 85% of theory based on mercapto compound. 

The HCl produced in this reaction is used in an oxychlorination reaction to chlorinate additional ethylene ... 

For example, the industrial synthesis of vinyl chloride involves a mixture of ethylene, chlorine and oxygen. This is carried out in such a way that hydrogen chloride which forms during the reaction keeps the ethylene/oxygen mixture outside the LEL - UEL range. 

Reaction of chlorine with ethylene to produce ethylene dichloride (EDC). 

Figure 9—2 shows the plant with its three reactors. The pyrolysis furnace is in the middle. At the top of the figure, the basic feeds, to the plant are shown—ethylene, chlorine, and oxygen. Ethylene and chlorine alone are sufficient to make EDC via the route on the left. The operation, call it Reaction One like Figure 9-1 does, takes place in the vapor phase in a reactor with a fixed catalyst bed of ferric (iron) chloride at only 100—125°F. A cleanup column fractionates out the small amount of by-products that get formed, leaving an EDC stream of 96—98% purity. 

The key intermediate in the preparation of bis(2-chloroethyl) ether from ethylene is 2-chloroethanol, formed from ethylene by reaction with chlorine in water. Heating 2-chloroethanol in acid gives the desired ether. 

Arnold WA, Roberts AL. Inter- and intraspecies competitive effects in reactions of chlorinated ethylenes with zero-valent iron in column reactors. Environ Eng Sci 2000 17 291-302. 

Figure 10.11 shows an integrated plant for producing EDC and vinyl chloride from ethylene, chlorine, and air. In this process, vinyl chloride (VCM) is produced by the thermal cracking of EDC. The feed EDC may be supplied from two sources. In the first source, ethylene and chlorine are reacted in essentially stoichiometric proportions to produce EDC by direct addition. In the second source, ethylene is reacted with air and HC1 by the oxychlorination process. Ideally, both processes are carried out in balance, and the oxychlorination process is used to consume the HC1 produced in the cracking and direct chlorination steps. The chemical reactions are... 

Direct chlorination of vinyl chloride generates 1,1,2-tnchloroethane [79-00-5] from which vinylidene chloride required for vinylidene polymers is produced. Hydrochlorination of vinylidene chloride produces 1,1,1-trichloroethane [71-55-6], which is a commercially important solvent. Trichloroethylene and perchloroethylene are manufactured by chlorination, hydrochlorination, or oxychlorination reactions involving ethylene. Aromatic solvents or pesticides such as monochlorobenzene, dichlorobenzene, and hexachlorobenzene are produced by reaction of chlorine with benzene. Monochlorobenzene is an intermediate in the manufacture of phenol, insecticide DDT, aniline, and dyes (see Chlorocarbons a>td Chlorohydrocarbons.)... 

Chlorohydrins and dichloroalkanes are formed in electrogenerative chlorination of olefins on platinum black (50). The former predominate at high currents and low anode potentials, with no side reactions of chlorides, such as chlorine evolution. From the identified products, the following tentative mechanism has been proposed for ethylene chlorination (50) ... 

It has been shown that by a proper choice of reaction conditions, chlorine substitution in (NPCl2)3 by sodium salts of poly(ethylene glycol)s can be achieved, to yield cis-non-geminal compounds N3P3Cl3(OR)3. The group R represents... 

It is obtained chiefly as a captive intermediate of vmyl chloride manufacture and, in the case of ethylene chlorination, it results from the foOowing exothermic reaction ... 

Recent applications of VTST/MT to polyatomic gas-phase reactions that illustrate the power of the theory include the reactions of chlorine atoms with hydrogen molecules [56] and the reactions of hydrogen atoms with ethylene [57,58] and methane [59], including kinetic isotope effects. 

Temperature and pressure can alter the course of a reaction as would be expected from thermodynamic considerations. The influence of temperature is shown in the reaction between chlorine and ethylene, which, in the presence of carbon, yields dichloro-ethylene at 120° to 125° C whereas higher temperatures favor the formation of hexachloroethane.49... 

Systematic attempts to improve the yield of y-isomer have been reported.123 Studies were made of the effect of adding compounds such as methyl chloride, chloroform, ethylene, and CS2 that undergo a chain reaction with chlorine, and of adding radical-formers such as... 

For example, the reaction of ethylene chlorination under the condition of significant excess of chlorine proceeds on such a scheme ... 

A balanced VCM process produces only vinyl-cloride by combining three reaction steps direct ethylene chlorination to 1,2-dichloroethane (DCE), cracking of DCE to VCM, and recovery of HCl by oxychlorination with ethylene. The global stoichiometry may be described by the simplified scheme ... 

The influence of hydrochloric acid concentration appeared to be similar to that in the case of aromatic compounds chlorination in the electrochemical system. While working with aphite electrodes in 27 - 30 hydrochloric acid solutions at the range of current density values from 1 to 4 IcA/m, and at the range of temperatures from 35 to 80°C, the dominating product of ethylene chlorination reaction was stated to be 1,2-dichloroethane. At 35°C, the yield of ethylene chlorination products is 68-8056 at rather low current densities. The increase in the temperature of chlorination process up to 50°C, at the same current densities cause the fiy-owth of the diohloroethane content in the mixture up to 77% - 92%. Though temperature growth to 65°C leads to some increase in total mixture mass of ethylene chlorination products, however, the substance yield of 1,2-diohloroethane is only 75-80%, as lateral processes take place. While temperature rises to SO C,... 

VInnollt GmbH CoKG Ethylene dichloride (EDC) via direct chlorination Ethylene, chlorine Direct chlorination process producess EDC cost-effectively with an exothermic reaction, heat integration with EDC purification, own catalyst based process 15 2010... 

Ethylene forms explosive mixtures in air the LEE and UEL values are 2.7% and 36% by volume of air, respectively. Its reaction with fluorine is explosively violent (AH = —112 kcal/mol), and violent with chlorine (AH = —36 kcal/mol). In the presence of sunlight or UV light, an ethylene-chlorine mixture will explode spontaneously. The reaction is explosive at room temperature over the oxides of mercury or silver (Mellor 1946, Suppl. 1956). Ethylene reacts vigorously with oxidizing substances. It reacts with ozone to form ethylene ozonide, H2C(03)CH2, which is unstable and explodes on mechanical shock. Acid-catalyzed addition of hydrogen peroxide may produce ethyl hydroperoxide, which is unstable and explodes on heat or shock ... 

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