Ethyn

Prepared from ethyne and ammonia or by dehydration of ethanamide. Widely used for dissolving inorganic and organic compounds, especially when a non-aqueous polar solvent of high dielectric constant is required, e.g. for ionic reactions. 

HOCH2CH2CH2CH2OH. B.p. 228"C. Prepared ethyne plus methanal, hydrogenated to butanediol. Used in production of y-buty-rolactone and 2-pyrrolidone. Widely used in polyurethane products, butylenes See butenes. 

HOCH2C = CCH2OH. White solid, m.p. 58 C, b.p. 238- C prepared by the high pressure reaction between ethyne and methanol and also from BrMgCCMgBr and methanal. Used in electroplating (Ni), as a corrosion inhibitor, and in paint and varnish removal. 

COT is prepared by the polymerization of ethyne at moderate temperature and pressure in the presence of nickel salts. The molecule is non-planar and behaves as a typical cyclic olefin, having no aromatic properties. It may be catalytically hydrogenated to cyclo-octene, but with Zn and dil. sulphuric acid gives 1,3,6-cyclooclairiene. It reacts with maleic anhydride to give an adduct, m.p. 166 C, derived from the isomeric structure bicyclo-4,2,0-octa-2,4,7-triene(I) ... 

C. It occurs in natural gas. May prepared by reduction of ethene or ethyne by hydrogen under pressure in the presence of a nickel catalyst, or by the electrolysis of a solution of potassium elhanoate. It has the general properties of the paraffins. Used in low-temperature refrigeration plant. 

The original method for the manufacture of ethyne, the action of water on calcium carbide, is still of very great importance, but newer methods include the pyrolysis of the lower paraffins in the presence of steam, the partial oxidation of natural gas (methane) and the cracking of hydrocarbons in an electric arc. 

Ethyne is the starting point for the manufacture of a wide range of chemicals, amongst which the most important are acrylonitrile, vinyl chloride, vinyl acetate, ethanal, ethanoic acid, tri- and perchloro-ethylene, neoprene and polyvinyl alcohol. Processes such as vinylation, ethinylation, carbonylation, oligomerization and Reppe processes offer the possibility of producing various organic chemicals cheaply. Used in oxy-acetylene welding. 

C, obtained from ethyne and propanone. It is used as a corrosion inhibitor and as a chemical intermediate. 

CH2 CH C CH. Colourless gas with a sweet odour b.p. 5°C. Manufactured by the controlled low-temperature telomerization of ethyne in the presence of an aqueous solution of CuCI and NH Cl. Reduced by hydrogen to butadiene and, finally, butane. Reacts with water in the presence of HgSO to give methyl vinyl ketone. Forms salts. Forms 2-chloro-butadiene (chloroprene) with hydrochloric acid and certain metallic chlorides. 

C-jHg. A slightly coloured liquid, b.p. 90 C, obtained by a Diels-Alder reaction between cyclopcntadiene and ethyne at approximately 150°C. At temperatures in excess of 450°C it rearranges to cycloheptatriene (tropilidene). 

CHjiCH-CN. Volatile liquid b.p. 78"C. Manufactured by the catalytic dehydration of ethylene cyanhydrin, by the addition of hydrogen cyanide to ethyne in the presence of CuCI or the reaction of propene, ammonia and air in the presence of a molybdenum-based catalyst. 

Commercially, pyridine is manufactured from ethyne and ammonia. It is used as a solvent, particularly in the plastics industry, in the manufacture of nicotinic acid, various drugs and rubber chemicals. 

HCCI2CHCI2. Colourless toxic liquid with a chloroform-like odour, b.p. 146 C. Manufactured by passing chlorine and ethyne separately into a solution of SbClj in tetra-chloroethane. Reacts with dilute alkalis to give trichloroethene . 

Trichloroethylene is manufactured by the dehydrochlorination of tetrachloroelhane derived from the chlorination of ethyne with lime or by vapour phase cracking. 

Triple bonds are formed by the sharing of three pairs of electrons to form a a and two n bonds. Spatially these three bonds behave as a single bond. Consequently acetylene (ethyne) C2H2 has the linear configuration often represented as H—C=C—H. 

There are many compounds in existence which have a considerable positive enthalpy of formation. They are not made by direct union of the constituent elements in their standard states, but by some process in which the necessary energy is provided indirectly. Many known covalent hydrides (Chapter 5) are made by indirect methods (for example from other hydrides) or by supplying energy (in the form of heat or an electric discharge) to the direct reaction to dissociate the hydrogen molecules and also possibly vaporise the other element. Other known endothermic compounds include nitrogen oxide and ethyne (acetylene) all these compounds have considerable kinetic stability. 

The salt-like carbides. Among these are aluminium tricarbide imethanide) AI4C3 (containing essentially C ions) in the crystal lattice and the rather more common dicarbides containing the C ion, for example calcium dicarbide CaCjt these carbides are hydrolysed by water yielding methane and ethyne respectively ... 

The solid readily dissolves chemically in concentrated hydrochloric acid, forming a complex, and in ammonia as the colourless, linear, complex cation [H3N -> Cu <- NHj] (cf AgCl) if air is absent (in the presence of air, this is oxidis to a blue ammino-copper(II) complex). This solution of ammoniacal copper(I) chloride is a good solvent or carbon monoxide, forming an addition compound CuCl. CO. H2O, and as such is used in gas analysis. On passing ethyne through the ammoniacal solution, a red-brown precipitate of hydrated copper(I) dicarbide (explosive when dry) is obtained ... 

If ethyne is passed through an ammoniacal solution of silver nitrate, there is a white precipitate of silver dicarbide (cf. copperflH ... 

Mercury compounds (for example mercury(II) chloride) are used in medicine because of their antiseptic character. The artificial red mercury(Il) sulphide is the artist s vermilion . Mercury(II) sulphate is a catalyst in the manufacture of ethanal from ethyne ... 

VViberg and Rablen found that the charges obtained with the atoms in molecules method were relatively invariant to the basis set. The charges from this method were also consistent v it i the experimentally determined C-H bond dipoles in methane (in which the carbon is p isitive) and ethyne (in which the carbon is negative), unlike most of the other methods they examined. 

---