1, 1 , 2, 2 -Tetrachloroethane

Data were last reviewed in lARC (1979) and the compound was classified in lARC Monographs Supplement 7 (1987). 

Abstr Serv. Reg.No. 79-34-5 Chem. Abstr. Name 1,1,2,2-Tetrachloroethane lUPAC Systematic Name 1,1,2,2-Tetrachlorocthane Synonym Acetylene tetrachloride 

2 Structural and molecular formulae and relative molecular mass 

Id) Solubility Slightly soluble in water (1 g/350 mL at 25°C) miscible with methanol, ethanol, benzene, diethyl ether, petroleum ether, carbon tetrachloride, chloroform, carbon disulfide, dimethylformamide and oils. Has the highest solvent power of the chlorinated hydrocarbons (Lide, 1995 Budavari, 1996) 

2-Tetrachloroethane is used as a solvent, for cleansing and degreasing metals, in paint removers, varnishes, lacquers, photographic film, resins and waxes, extraction of oils and fats, as an alcohol denaturant, in organic synthesis, in insecticides, as a weedkiller and fumigant and as an intennediate in the manufacture of other chlorinated hydrocarbons (Lewis, 1993). 

Though rarely used in current practice, this solvent was an important cause of hepatotoxicity in the past. Its hepatotoxic potential was first identified during its use in the first World War. Animal hepatotoxicity with fatty degeneration of the fiver has been documented in multiple species. Human inhalational exposures manifest in fiver enlargement, jaundice, steatosis with subsequent fiver failure in severe poisonings. Subacute exposure periods of weeks to months is generally required for hepatic injiuy. Liver regeneration oc- 

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Tetrachloroethane is a good solvent for many compounds which dissolve only slightly in the common solvents it is, however, inferior in solvent power to nitrobenzene, but, on the other hand, it does not possess oxidising properties at the boiling point. 

Carbon tetrachloride Ethylene chloride. Trichloroethylene. Propylene chloride. Ethylene chlorobromide 1 1 2-Trichloroethane Trimethylene chloride Tetrachloroethylene Trimethylene chlorobromide sym. Tetrachloroethane 1 4 Dichlorobutane 1 2 3-Trichloropropane Pentachloroothane. ... 

By distilling the acid with an inert solvent of high boiling point, such as tetrachloroethane. The water passes over with the solvent and the anhydride remains, for example ... 

Mix 100 g. of maleic acid (Section 111,143) and 100 ml. of tetra chloroethane in a 250 ml. Claisen or distilling flask provided with a thermometer, and attach a Pyrex Liebig condenser. Heat the flask in an air bath (Fig. 11, 5, 3) and collect the distillate in a measuring cylinder. When the temperature reaches 160°, 76 ml. of tetrachloroethane and 15-15-5 ml. of water are present in the receiver. Empty the water in the condenser and continue the distillation change the receiver when the temperature reaches 190°. Collect the maleic anhydride at 195-197°. Recrystallise the crude anhydride from chloroform. The yield of pure maleic anhydride, m.p. 54°, is 70 g. 

Place a mixture of 1 0 g. of the hydrocarbon, 10 ml. of dry methylene chloride or ethylene dichloride or syw.-tetrachloroethane, 2 5 g. of powdered anhydrous aluminium chloride and 1-2 g. of pure phthalic anhydride in a 50 ml. round-bottomed flask fitted with a short reflux condenser. Heat on a water bath for 30 minutes (or until no more hydrogen chloride fumes are evolved), and then cool in ice. Add 10 ml. of concentrated hydrochloric acid cautiously and shake the flask gently for 5 min utes. Filter oflf the solid at the pump and wash it with 10-15 ml. of cold water. Boil the resulting crude aroylbenzoic acid with 10 ml. of 2 -5N sodium carbonate solution and 0 2 g. of decolourising carbon for 5 minutes, and filter the hot solution. Cool, add about 10 g. of crushed ice and acidify... 

The first portion of the steam distillate consists almost entirely of tetrachloroethane and water. The solvent is recovered by separating the organic layer, drying with anhydrous calcium chloride or magnesium sulphate and distilling. 

In 1973 the Semiconductor Equipment and Materials Institute (SEMI) held its first standards meeting. SEMI standards are voluntary consensus specifications developed by the producers, users, and general interest groups in the semiconductor (qv) industry. Examples of electronic chemicals are glacial acetic acid [64-19-7] acetone [67-64-17, ammonium fluoride [12125-01 -8] and ammonium hydroxide [1336-21 -6] (see Ammonium compounds), dichloromethane [75-09-2] (see Cm.OROCARBONSANDcm.OROHYDROCARBONs), hydrofluoric acid [7664-39-3] (see Eluorine compounds, inorganic), 30% hydrogen peroxide (qv) [7722-84-1] methanol (qv) [67-56-1] nitric acid (qv) [7697-37-2] 2-propanoI [67-63-0] (see Propyl alcohols), sulfuric acid [7664-93-9] tetrachloroethane [127-18-4] toluene (qv) [108-88-3] and xylenes (qv) (see also Electronic materials). 

Halogenation and Hydrohalogenation. Halogens add to the triple bond of acetylene. FeCl catalyzes the addition of CI2 to acetylene to form 1,1,2,2-tetrachloroethane which is an intermediate in the production of the industrial solvents 1,2-dichloroethylene, trichloroethylene, and perchloroethylene (see Chlorocarbons and chlorohydrocarbons). Acetylene can be chlorinated to 1,2-dichloroethylene directiy using FeCl as a catalyst... 

Tetrachloroethylene can be prepared direcdy from tetrachloroethane by a high temperature chlorination or, more simply, by passing acetylene and chlorine over a catalyst at 250—400°C or by controlled combustion of the mixture without a catalyst at 600—950°C (32). Oxychl orin a tion of ethylene and ethane has displaced most of this use of acetylene. 

The older methods have been replaced by methods which require less, if any, excess sulfuric acid. For example, sulfonation of naphthalene can be carried out in tetrachloroethane solution with the stoichiometric amount of sulfur trioxide at no greater than 30°C, followed by separation of the precipitated l-naphthalenesulfonic acid the filtrate can be reused as the solvent for the next batch (14). The purification of 1-naphthalenesulfonic acid by extraction or washing the cake with 2,6-dimethyl-4-heptanone (diisobutyl ketone) or a C-1—4 alcohol has been described (15,16). The selective insoluble salt formation of 1-naphthalenesulfonic acid in the sulfonation mixture with 2,3-dimethyl aniline has been patented (17). 

Solubility and Solvent Resistance. The majority of polycarbonates are prepared in methylene chloride solution. Chloroform, i7j -l,2-dichloroethylene, yy -tetrachloroethane, and methylene chloride are the preferred solvents for polycarbonates. The polymer is soluble in chlorobenzene or o-dichlorobenzene when warm, but crystallization may occur at lower temperatures. Methylene chloride is most commonly used because of the high solubiUty of the polymer (350 g/L at 25°C), and because this solvent has low flammabiUty and toxicity. Nonhalogenated solvents include tetrahydrofuran, dioxane, pyridine, and cresols. Hydrocarbons (qv) and aUphatic alcohols, esters (see Esters, organic), or ketones (qv) do not dissolve polycarbonates. Acetone (qv) promotes rapid crystallization of the normally amorphous polymer, and causes catastrophic failure of stressed polycarbonate parts. 

SolubiHty of the three commercial polysulfones foUows the order PSF > PES > PPSF. At room temperature, all three of these polysulfones as weU as the vast majority of other aromatic sulfone-based polymers can be readily dissolved in a few highly polar solvents to form stable solutions. These solvents include NMP, DMAc, pyridine, and aniline. 1,1,2-Trichloroethane and 1,1,2,2-tetrachloroethane are also suitable solvents but are less desirable because of their potentially harmful health effects. PSF is also readily soluble in a host of less polar solvents by virtue of its lower solubiHty parameter. 

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