Dichloroethane, EDC

The EDC belongs to the chemicals with the highest production rates, the annual production was about 14 million tonnes in 1998, the demand is still rising. It is the biggest single consumer for chlorine. 

Industrially it is produced by the chlorination of ethene, either by the direct chlorination process using chlorine or by the oxychlorination with hydrogen chloride as 

In practice, both processes are carried out together and in parallel because most EDC plants are connected to vinyl chloride monomer (VCM) units, and the oxychlorination process is used to balance the hydrogen chloride from the VCM production. 

In the direct chlorination process ethene and chlorine are reacted most commonly in the liquid phase of 1,2-dichloroethane in the presence of a catalyst, primarily iron(III) chloride. 

In the low-temperature chlorination the heat of the exothermic reaction is removed by indirect cooling of the reactor to temperatures below the b.p. of EDC, e.g.20 - 70 °C. The advantages are low formation of byproducts and less problems with construction materials, the disadvantage is the high energy input for the rectification of the EDC. 

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In the production of dichloroethane (EDC) by oxyhydrochlorination of ethylene, the products from the reaction are quenched by direct contact with dilute HC1 in a quench tower. The gaseous stream from this quench tower is fed to a condenser and the uncondensed vapours recycled to the reactor. A typical composition for this stream is shown in the diagram below operating pressure 4 bar. Calculate the outlet stream compositions leaving the condenser. 

This example illustrates the use of liquid-liquid phase equilibria in material balance calculations. The condensate stream from the condenser described in Example 4.2 is fed to a decanter to separate the condensed water and dichloroethane (EDC). Calculate the decanter outlet stream compositions. 

Hee SSQ, Igwe OJ, Boyle JR. 1988. Elemental alterations during the exposure of 1,2,-dichloroethane (EDC), disulfiram (DSF), and EDC-DSF to male Sprague-Dawley rats. Biol Trace Elem Res 18 61-80. 

Example 4.28 Assessment of separation section of vinyl chloride monomer (VCM) plant VCM is produced by the pyrolysis of 1,2-dichloroethane (EDC) at 483°C and 26.5 atm with a conversion of 55%. The pure EDC is fed to the reactor with a flow rate of 909.1 kmol/h. The feed is at21°Cand26.5 atm. The reactor outlet is cooled to 47.6°C. The first column operates at 25 atm with 15 stages. The feed is introduced at stage 8. The top product is anhydrous... 

The chirality of the pretransition liquid crystal is the same as that of the dilute solution of the respective polymer. As the temperature is increased, the optical activity is reduced in a continuous fashion to that observed in dilute solution, without change of sign. This effect is observed in CH2CI2, 1,2-dichloroethane (EDC), pyridine, and 2-chloropyridine. 

ELECTRON MICROSCOPY. The samples were prepared for electron microscopy as follows. The test materials with the adsorbed protein were placed in a vacugm evaporator (2 ). The specimens were dehydrated in vacuo (10 Torr) for 60 min., shadowed with tungsten, and carbon coated. The plastic substrates were dissolved in an appropriate solvent, either 1,2-dichloroethane (EDC), or N,N-dimethylacetamide (DMAC). The carbon replica, mounted on an microscope grid, was examined in the electron microscope. For observation, we used a Philips 300 electron microscope operated at 80 kV with a 50 micron objective aperture. 

In the company Aerojet, based on the TerMeer method [37], DNPOH was synthesized from as the starting material nitroethane in dichloroethane (EDC), through the chlorification with sodium chloride, substitution of chlorine atom with nitro, and finally reaction with formaldehyde under the action of sulfuric acid. The reaction mechanism is ... 

Vinyl chloride monomer (VCM) is produced by the pyrolysis of 1,2-dichloroethane (EDC) at around 483 °C and 26.5 atm with a conversion of 55%. The figure below shows the process flow diagram. 

After keeping this reaction mixture in sunlight for 4 days, a white powder, PVC, was formed. Although chemists [293-296] continued investigations on the syntheses and properties of the monomer and polymer, full-scale commercial production of PVC started not before 1930. Today, the technical preparation of VC [297-299] is mainly based on the thermic fission of 1,2-dichloroethane (EDC) ... 

Chlorinated by-products of ethylene oxychlorination typically include 1,1,2-trichloroethane chloral [75-87-6] (trichloroacetaldehyde) trichloroethylene [7901-6]-, 1,1-dichloroethane cis- and /n j -l,2-dichloroethylenes [156-59-2 and 156-60-5]-, 1,1-dichloroethylene [75-35-4] (vinyhdene chloride) 2-chloroethanol [107-07-3]-, ethyl chloride vinyl chloride mono-, di-, tri-, and tetrachloromethanes (methyl chloride [74-87-3], methylene chloride [75-09-2], chloroform, and carbon tetrachloride [56-23-5])-, and higher boiling compounds. The production of these compounds should be minimized to lower raw material costs, lessen the task of EDC purification, prevent fouling in the pyrolysis reactor, and minimize by-product handling and disposal. Of particular concern is chloral, because it polymerizes in the presence of strong acids. Chloral must be removed to prevent the formation of soflds which can foul and clog operating lines and controls (78). 

By-products from EDC pyrolysis typically include acetjiene, ethylene, methyl chloride, ethyl chloride, 1,3-butadiene, vinylacetylene, benzene, chloroprene, vinyUdene chloride, 1,1-dichloroethane, chloroform, carbon tetrachloride, 1,1,1-trichloroethane [71-55-6] and other chlorinated hydrocarbons (78). Most of these impurities remain with the unconverted EDC, and are subsequendy removed in EDC purification as light and heavy ends. The lightest compounds, ethylene and acetylene, are taken off with the HCl and end up in the oxychlorination reactor feed. The acetylene can be selectively hydrogenated to ethylene. The compounds that have boiling points near that of vinyl chloride, ie, methyl chloride and 1,3-butadiene, will codistiU with the vinyl chloride product. Chlorine or carbon tetrachloride addition to the pyrolysis reactor feed has been used to suppress methyl chloride formation, whereas 1,3-butadiene, which interferes with PVC polymerization, can be removed by treatment with chlorine or HCl, or by selective hydrogenation. 

Chlorination of various hydrocarbon feedstocks produces many usehil chlorinated solvents, intermediates, and chemical products. The chlorinated derivatives provide a primary method of upgrading the value of industrial chlorine. The principal chlorinated hydrocarbons produced industrially include chloromethane (methyl chloride), dichloromethane (methylene chloride), trichloromethane (chloroform), tetrachloromethane (carbon tetrachloride), chloroethene (vinyl chloride monomer, VCM), 1,1-dichloroethene (vinylidene chloride), 1,1,2-trichloroethene (trichloroethylene), 1,1,2,2-tetrachloroethene (perchloroethylene), mono- and dichloroben2enes, 1,1,1-trichloroethane (methyl chloroform), 1,1,2-trichloroethane, and 1,2-dichloroethane (ethylene dichloride [540-59-0], EDC). 

The chemistry of side reactions and by-products may also offer opportunities for increasing the inherent safety of a process. For example, a process involving a caustic hydrolysis step uses ethylene dichloride (EDC 1,2-dichloroethane) as a solvent. Under the reaction conditions a side reaction between sodium hydroxide and EDC produces small but hazardous quantities of vinyl chloride ... 

Synonyms AI3-01656 1,2-Bichloroethane Borer sol BRN 605264 Brocide Caswell No. 440 CCRIS 225 1,2-DCA 1,2-DCE Destruxol borersol Dichloremulsion 1,2-Dichlorethane Dichlormulsion a,p-Dichloroethane sjm-Dichloroethane Dichloroethylene Dutch liquid Dutch oil EDC EINECS 203-458-1 ENT 1656 EPA pesticide chemical code 042003 Ethane dichloride Ethene dichloride Ethylene chloride Ethylene dichloride 1,2-Ethylene dichloride Freon 150 Glycol dichloride HCC 150 NC1-C00511 RCRA waste number U077 UN 1184. 

EDC, see 1,2-Dichloroethane Edco, see Methyl bromide Effusan, see 4,6-Dinitro-o-cresol Effusan 3436, see 4,6-Dinitro-o-cresol EGBE, see 2-Butoxyethanol EGEE, see 2-Ethoxyethyl acetate Egitol, see Hexachloroethane... 

Boc-(R,/ )-/ra s-ACHC-OBzl (31 0.047 g, 0.14 mmol) was dissolved in 4M HCl/dioxane (0.5 mL) and stirred for 1 h. The solvent was then removed under a stream of N2, and the residue 34 was dried under vacuum. Boc-(f ,f )-trans-ACHC-OH (33 0.034g, 0.14mmol) and DMAP (0.023g, 0.19mmol) were added followed by DMF (lmL). EDC (0.059 g, 0.31 mmol) was added, and the reaction was stirred for 48 h under N2. Solvent was removed under a stream of N2, and the residue was further dried under vacuum. To this residue was added 1M HQ ( 3mL) and the solid that did not dissolve was isolated by suction filtration and washed with additional 1M HC1. The solid was dried under vacuum yield 0.051 g (79%). Fluffy crystals were grown by vapor diffusion of heptane into a soln of 35 in 1,2-dichloroethane mp 195 °C. 

Vinyl Chloride. [CAS 75-fl I -4. This compound is produced by alkaline dehydrnchlorinaiion of ethylene dichloride, or by thermal cracking of EDC, or l.l-dichloroethane. Vinyl chloride is polymerized in various ways to polyvinyl chloride (PVC). It is also copolymerized with various other monomers to make a variety of useful resins. The copolymers with about J to 20vinyl acetate are the most important. Demand for vinyl chloride is high, approximating 8 billion pounds (3.6 billion kilograms) per year. 

Abbreviations BAL, backbone amide linker BSA, bis(trimethylsilyl)acetamide DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene DCE, dichloroethane DCM, dichloromethane DIC, 2-diisopropylcarbodiimide DIEA, diisopropylethyl amine DMAP, A,A-dimethylaminopyr-idine DMF, dimethylformamide DMSO, dimethyl sulfoxide EDC, l-(3-dimethylaminopro-pyl)-3-ethylcarbodiimide hydrochloride HBTU, [0-(7-azabenzotriazol-l-yl)-l, 1,3,3-tetramethyluronium hexafluorophosphate MCPBA, m-chloroperoxybenzoic acid NMP, N-methylpyrrolidinone NMM, A-methylmorpholine PfP, pentafluorophenol RT, room temperature TFA, trifluoroacetic acid THF, tetrahydrofuran. 

Synonym ethylene chloride, ethylene dichloride, glycol dichloride, sym-dichloroethane, Dutch oil, EDC... 

Trichloroethane can be produced by three methods by chlorination of 1,1-dichloroethane, from 1,1,2-trichloroethane via 1,1 -dichloroethylene, and by direct chlorination of ethane. In the United States the first route produces about 70 percent. In this process the EDC feedstock is rearranged to... 

Note VCM = vinyl chloride monomer EDC = 12 dichloroethane [Lahiere and Goodboy, 1993]... 

Synonyms Ethylene dichloride 1,2-Ethylene dichloride Glycol dichloride EDC sym-Dichloroethane 1,2-Dichloroethane Ethylene chloride. 

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... 

Ethylene Dichloride Brocide 1,2-Dichloroethane Dutch Liquid Edc Ethylene Chloride... 

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