2- ethyl chloride

Ethyl Chloride. Hydrochlorination of ethylene with HC1 is carried out in either the vapor or the liquid phase, in the presence of a catalyst.182-184 Ethyl chloride or 1,2-dichloroethane containing less than 1% A1C13 is the reaction medium in the liquid-phase process operating under mild conditions (30-90°C, 3-5 atm). In new plants supported AlClj or ZnCl2 is used in the vapor phase. Equimolar amounts of the dry reagents are reacted in a fluidized- or fixed-bed reactor at elevated temperature and pressure (250-400°C, 5-15 atm). Both processes provide ethyl chloride with high (98-99%) selectivity. 

A highly economical production of ethyl chloride combines radical ethane chlorination and ethylene hydrochlorination.185 186 Called the Shell integrated process, it uses the hydrogen chloride produced in the first reaction to carry out the second addition step  

Ethyl chloride was used in the manufacture of the antiknock agent tetraethyllead, which is, however, phased out. 

Ethyl chloride is commercially produced by the liquid-phase hydrochlorination of ethylene in large-scale reactors (2 m ), in the presence of AICI3. Reactors are equipped with mechanical mixing devices and an external heat removal system the temperature in the mixing zone may locally increase up to 100 °C or more. 

There is no information on the specific reaction rate of the hydrochlorination of ethylene to chloroethane in the relevant literature or reference books. However, this reaction relates to rapid processes according to the technical rules, = 5 s at more than 93 mass% of the ethylene change ratio, which results in fe 190 1/mohs (238°C). Therefore, turbulent reactors are the most appropriate devices for this 

Elimination of chloroethane emission from the reactor and colonr defect products. 

Simplification of the technology and process equipment, keeping the main principles of the current flow sheet. 

Reduction of the reaction mixture residence time in the reaction zone (by more than a factor of 100 20). 

At ordinary temperatures the oxidation and hydrolysis of ethyl chloride take place slowly. In (he absence of air and water, it can be used with most common metals up to 200°C (392 F). Ethyl chloride burns with a green-edged flame, producing hydrogen chloride, carbon dioxide and water. It is thermally stable to 400 C (752 F) thermal flitting yields ethylene and hydrogen chloride. The reactivity of ethyl chloride as an intermediate is often based on the affinity of alkali metal atoms for its chlorine atom. 

Nonvolatile Residue, wt % Total Impurities, wt % Distillation Range, C Specific Gravity, 0 C/4°C 

5 minimum 20 maximum clear, free of suspended matter 0.002 maximum 0.02 maximum 0.01 maximum 0.5 maximum 12 to 13 0.922 to 0.925 

Vernot EH et ah Acute toxicity and skin corrosion data for some organic and inorganic compounds and aqueous solutions. Toxicol Appl Pharmacol Y2 All1977 

National Toxicology Program Toxicology and Carcinogenesis Studies of Bromoethane (Ethyl Bromide) (CAS NO. 14-96-4) in F344/N Pats and B6C3F Mice (Inhalation Studies), NTP-TR 363 NIH Pub No 90-2818, pp 1-186. US Dept Health and Human Services, 1989 

lARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol 71, Re-evaluation of some organic chemicals, hydrazine and hydrogen peroxide, pp 1305-1307. Lyon, International Agency for Research on Cancer, 1999 

Hygienic Guide Series Ethyl bromide. Am Ind Hyg Assoc 26-. 92- 95, 1978 

Toxicology. Ethyl butyl ketone (EBK) is mildly irritating to the skin and eyes of animals and causes narcosis at high concentrations. 

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CH3CH2)2S. a colourless liquid with an ethereal odour when pure usually it has a strong garlic-like odour b.p. 92°C. Prepared by the action of KHS on ethyl chloride or potassium ethyl sulphate. When heated at 400-500°C it forms thiophene. 

Ethylamine, monoethylamine, CH3CH2NH2-B.p. 19 C. Prepared by reduction of acetonitrile or by heating ethyl chloride with alcoholic ammonia under pressure. It is a strong base and will displace ammonia from ammonium salts. Forms a crystalline hydrochloride and also crystalline compounds with various metallic chlorides. 

CgHgNOs. Yellow crystals m.p. 58 C, b.p. 283 C. Prepared by the ethylation of />-nitro-phenol with ethyl chloride. It is used for preparing p-phenetidine. 

Dissolve 7 g. of pure oleic acid in 30 ml. of dry ethyl chloride (chloroform may be used but is less satisfactory), and ozonise at about —30°. Remove the solvent under reduced pressure, dissolve the residue in 50 ml. of dry methyl alcohol and hydrogenate as for adipic dialdehyde in the presence of 0 5 g. of palladium - calcium carbonate. Warm the resulting solution for 30 minutes with a slight excess of semicarbazide acetate and pour into water. Collect the precipitated semicarbazones and dry the... 

In the second, which belongs to a systematic study of the transmission of substituent effects in heterocyclic systems, Noyce and Forsyth (384-386) showed that for thiazole, as for other simple heterocyclic systems, the rate of solvolysis of substituted hetero-arylethyl chlorides in 80% ethanol could be correlated with a constants of the substituent X only when there is mutual conjugation between X and the reaction center. In the case of thiazole this situation corresponds to l-(2-X-5-thiazolyl)ethyl chlorides (262) and l-(5-X-2-thiazolyl)ethyl chlorides (263). 

Although Noyce and Fike have recently found for the solvolysis of 2-thiazolyl-ethyl chlorides analogous modality of substituent electronic effect transmission from position 2 toward position 5 and from position 5 toward position 2(60). a more general conclusion indicates that the... 

Chlorination of ethane yields in addition to ethyl chloride a mixture of two isomeric dichlorides What are the structures of these two dichlorides ... 

Fig. 4.25 Adsorption isotherms showing low-pressure hysteresis, (a) Carbon tetrachloride at 20°C on unactivated polyacrylonitrile carbon Curves A and B are the desorption branches of the isotherms of the sample after heat treatment at 900°C and 2700°C respectively Curve C is the common adsorption branch (b) water at 22°C on stannic oxide gel heated to SOO C (c) krypton at 77-4 K on exfoliated graphite (d) ethyl chloride at 6°C on porous glass. (Redrawn from the diagrams in the original papers, with omission of experimental points.)...

The swelling of the adsorbent can be directly demonstrated as in the experiments of Fig. 4.27 where the solid was a compact made from coal powder and the adsorbate was n-butane. (Closely similar results were obtained with ethyl chloride.) Simultaneous measurements of linear expansion, amount adsorbed and electrical conductivity were made, and as is seen the three resultant isotherms are very similar the hysteresis in adsorption in Fig. 4.27(a), is associated with a corresponding hysteresis in swelling in (h) and in electrical conductivity in (c). The decrease in conductivity in (c) clearly points to an irreversible opening-up of interparticulate junctions this would produce narrow gaps which would function as constrictions in micropores and would thus lead to adsorption hysteresis (cf. Section 4.S). 

Fig. 4.27 Swelling and low-pressure hysteresis in the adsorption of n-butane on compacts of coal at 273 K. The following are plotted against the relative pressure (a) the amount adsorbed (b) the percentage increase on length (c) the decrease —Ajc in electrical conductivity. The curves for ethyl chloride were very similar to the above curves.

It has been observedt that poly(1,1-dimethyl propane) is the product when 3-methylbutene-l is polymerized with AICI3 in ethyl chloride at -130°C. Write structural formulas for the expected repeat units and those observed and propose an explanation. 

Other acetyl chloride preparations include the reaction of acetic acid and chlorinated ethylenes in the presence of ferric chloride [7705-08-0] (29) a combination of ben2yl chloride [100-44-7] and acetic acid at 85% yield (30) conversion of ethyUdene dichloride, in 91% yield (31) and decomposition of ethyl acetate [141-78-6] by the action of phosgene [75-44-5] producing also ethyl chloride [75-00-3] (32). The expense of raw material and capital cost of plant probably make this last route prohibitive. Chlorination of acetic acid to monochloroacetic acid [79-11-8] also generates acetyl chloride as a by-product (33). Because acetyl chloride is cosdy to recover, it is usually recycled to be converted into monochloroacetic acid. A salvage method in which the mixture of HCl and acetyl chloride is scmbbed with H2SO4 to form acetyl sulfate has been patented (33). 

Acetylene and hydrogen chloride historically were used to make chloroprene [126-99-8]. The olefin reaction is used to make ethyl chloride from ethylene and to make 1,1-dichloroethane from vinyl chloride. 1,1-Dichloroethane is an intermediate to produce 1,1,1-trichloroethane by thermal (26) or photochemical chlorination (27) routes. 

Ethyl Chloride. Most ethyl chloride [75-00-3] is produced by the hydrochlorination of ethylene (qv) using anhydrous HCl. Historically, the primary use of ethyl chloride was for the manufacture of tetraethyllead (TEL), a primary component of antiknock mixes in gasolines. Use has declined as a... 

Liquid-Ph se Processes. Prior to 1980, commercial hquid-phase processes were based primarily on an AIQ. catalyst. AIQ. systems have been developed since the 1930s by a number of companies, including Dow, BASF, Shell Chemical, Monsanto, SociStH Chimique des Charboimages, and Union Carbide—Badger. These processes generally involve ethyl chloride or occasionally hydrogen chloride as a catalyst promoter. Recycled alkylated ben2enes are combined with the AIQ. and ethyl chloride to form a separate catalyst—complex phase that is heavier than the hydrocarbon phase and can be separated and recycled. 

Fig. 2. Annual anhydrous aluminum chloride market, 1984, 10 t/yr (10). I, Dyestuffs , ethylben2ene , ethyl chloride [...

Direct Process. The preparation of organosilanes by the direct process, first reported in 1945, is the primary method used commercially (142,143). Organosilanes in the United States, France, Germany, Japan, and the CIS are prepared by this method, including CH SiHCl, (CH2)2SiHCl, and C2H SiHCl2. Those materials are utilized as polymers and reactive intermediates. The synthesis involves the reaction of alkyl haUdes, eg, methyl and ethyl chloride, with siUcon metal or siUcon alloys in a fluidized bed at 250—450°C ... 

Alternatives to the methyl chloride dkect process have been reviewed (31). Processes to make phenyl and ethyl siUcones have employed dkect-process chemistry. Phenyl chloride has been used in place of methyl chloride to make phenylchlorosilanes (15). In addition, phenylchlorosilanes are produced by the reaction of benzene, HSiCl, and BCl (17,31). EthylsiUcones have been made primarily in the CIS, where the dkect process is carried out with ethyl chloride in place of methyl chloride (32). Vinyl chloride can also be used in the dkect process to produce vinylchlorosilanes (31). Alternative methods for making vinylchlorosilanes include reaction of vinyl chloride with HSiCl or the platinum-catalyzed hydrosilylation of acetjdene with HSiCl. ... 

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