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Encyclopedia Britannica - Main :: BUN-CAL |
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C36H33CH : CH2+RCOOH ; from tertiary alcohols .by the action of acetic anhydride in the presence of a small quantity of sulphuric acid (L. Henry
(CH3)2.C(OH)CH(CH3)2-->(CH3)2C:C(CH3)2+CH2:C(CH3)CH (CH3)2; from unsaturated alcohols by the action of metal-ammonium compounds (E. Chablay, Comptes rendus, 1906, 143, p. 123) : 2CH2:CHCH2OH+2NH3Na = CH2:CH.CHs +CH2:CH. CH2ONa +NaOH+2NH3; from the lower members of the series by heating them with alkyl halides in the presence of lead oxide
A. Mailhe (Chem. Zeit., 1906, 30, p. 37) has shown that on passing the monohalogen derivatives of the paraffins through a glass tube containing reduced nickel, copper or cobalt
cobalt
In their physical properties, the olefines resemble the normal paraffins, the lower members of the series being inflammable gases, the members from C5 to C,4 liquids insoluble in water,and from C16 upwards of solids. The chief
Name. Formula
. C Ethylene . . CH2:CH2 -169 -102.7 (757 mm.) Propylene . . CH3CH:CH2 .. -50.2 (749 mm.) Butylene . . C2H5CH:CH2 .. -5 Amylene . . C3H7CH:CH2 .. 3940 Hexylene . . C4H9CH:CH2 .. 687o Heptylene . . C&H11CH:CH2 .. 95 Octylene . . C6H13CH:CH2 .. 122123 Decylene . C5H1,CH:CH2 I .. 172 Undecylene . . C5 H19CH :CH2: 84 (18 mm.) Duodecylene . C1oH21CH:CH2 -31 96 (15 mm.) In chemical properties, however, they differ very markedly from the paraffins. As unsaturated compounds they can combine with two monovalent atoms. Hydrogen is absorbed readily at ordinary temperature in the presence of platinum black, and paraffins are formed; the halogens (chlorine and bromine) combine directly with them, giving dihalogen substituted compounds; the halogen halides to form monohalogen derivatives (hydriodic acid reacts most readily, hydrochloric acid, least); and it is to be noted that the haloid acids attach themselves in such a manner that the halogen atom unites itself to the carbon atom which is in combination with the fewest hydrogen atoms (W. Markownikow, Ann., 1870, 153, p. 2561.They combine with hypochlorous acid to form chlorhydrins; and are easily soluble in concentrated sulphuric acid, giving rise to sulphuric acid esters; consequently if the solution be boiled with water, the alcohol from which the olefine was in the first place derived is regenerated. The oxides of nitrogen convert them into nitrosites and nitrosates (0. Wallach, Ann., 1887, 241, p. 288, &c.; J. Schmidt, Bet., 1902, 35. pp. 2323 et seq.). They also combine with nitrosyl bromide and chloride, and with many metallic haloid salts (platinum bichloride, iridium chloride), with mercury salts (see K. A. Hofmann and J. Sand, Ber., 1900, 33, pp. 1340 et seq.), and those with a tertiary carbon atom yield double
For the first member of the series see ETHYLENE. Propylene, C3H6, may be obtained by passing the vapour of trimethylene through a heated tube (S. M. Tanatar, Ber., 1899, 32, pp. 702, 1965). It is a colourless gas which may be liquefied by a pressure of 7 to 8 atmospheres. Butylene, C4H3, exists in three Isomeric forms: normal butylene, C2H5CH:CH2; pseudo-butylene, CH3.CH:CHCH3;andisobutylene, (CH3)2C:CH2. Normal butylene is a readily condensible gas. Two spatial modifications of pseudobutylene, CH3CH:CHCH3,are known, the cis and the trans; they are prepared by heating the sodium salts of hydro-iodo-tiglic and hydro-iodo-angelic acids respectively (J. Wislicenus, Ann., 1900, 313, p. 228). Isobutylene, (CH3)2C: CH2, is formed in the dry distillation of fats, and also occurs among the products obtained when the vapour of fusel oil is led through a heated tube. It is a gas at ordinary temperature, and may be liquefied, the liquid boiling at -5 C. It combines with acetyl chloride in the presence of zinc chloride to form a ketone, which on warming breaks down into hydrochloric acid and mesityl oxide
C2H6
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