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Organic Chemistry. T View Article Online / Journal Homepage / Table of Contents for this issue i. 369 Organic Chemistry. Nature of the Kolbe Electrochemical Synthesis of Hydrocarbons. FH. FICHTERand EDUARDKRUMMENAUHEH (Helvetica Chim. A cia, 1918, 1, 146-166).-The authors discuss the two theories put forward to explain the' mechanism of the Kolbe hydrocarbon synthesis, and draw the conclusion that the oxidation thsory is more in accord with fact than the theory based on the ionic hypothesis. It is shown that peroxides are produced by electrochemical oxidation, on platinum anodes, of solutions of saturated fatty acids and their salts. Since them peroxides may be produced by the action of hydrogen peroxide on aci6 anhydrides, it is to be assumed that the separation of the anhydride is the first step in the hydrocarbon synthesis. The anhydride is then anodic- ally oxidised, with the formation of a very unstable peroxide. The peroxide is then decomposed by the relatively high tempera- ture of the anode, with the formation of the hydrocarbon, thus: R*CO,Na + (RCO),-0 + 0 + (RCO),*O = 0 + R*R+ 2CO,, or a side reaction may also occur, thus: (R*CO),O=O 4 R-CO,*R + CO,. When th? peroxides are decomposed by heat, there is also a considerable amount of methane produced in addition to the expected hydrocarbon. These considerations are adapted to the formation and decom- position of organic peracids. Organic peracids m:by be prepared by the action of hydrogen peroxide on both acids and anhydrides, consequently the formation of these substances electrolytically on the, anode does not necessarily demand the intermediary formation Published on 01 January 1918. Downloaded 28/10/2014 00:35:27. of the anhydride. A further possibility also arises from the fact that peracids may be hydrolysed to peroxide&. The peracids also decompose at the anode surface, giving carbon dioxide and an alcohol, R*CO,H + R*OH+CO,, or carbon dioxide and an un- saturated hydrocarbon, C,&, + ,-CO,H = C,Hm + CO, + H,O. By the electrolysis of sulphonediacetic acid or its salts, tlie pro- ducts are carbon dioxide and sulphuric acid, and not the expected product, diethylene disulphone. J. F. S. Determination of the Normal Density of Ethylene. T. BATUECAS(Anal. Fis. Quim., 1918, 16, 258-281 ; flelvetica Chim. Acta, 1918, 1, 136--141).-The mean of twenty-one determinations with samples of ethylene prepared from ethyl alcohol by phosphoric acid, boric acid, sulphuric acid, and alumina gave for the normal density the value Lo= 1.26031 grams. A. J. W. Silver Acetylide. JOHNEGGERT (Zeitsch. EEektroche9nn., I 91 8, 24, 150-154. Compare A., 1918, ii, 228).-The amount of gaseous product produced by the detonation of silver acetylide depends on the method of preparation. Silver ace tylide prepared VOL. om. i. t View Article Online i. 370 ABSTRACTS OF CHEMICAL PAPERS. from an acid silver nitrate solution evolves about ten times the volume of gas, on detonation, as does material prepared in ammoniacal solution, neutral solution, or in solution of hydroiluoric acid. The material prepared in nitric acid solutim contains 78.5% of silver, and the gaseous product of detonation consists of a mix- ture of carbon monoxide, carbon dioxide, methane, hydrogen, nitrogen, nitric oxide, and water vapour. The material prepared in 2% ammoniacal solution contains 89.5% of silver, and the product of detonation consists of carbon monoxidel, carbon dioxide, methane, hydrogen, and water vapour. The analyses show that the product from nitric acid consists of 5776 of silver acetylide and 43% of silver nitrate, whilst that from ammonia consists of 86% of silver acetylide and 14% of silver hydroxide. J. F. S. Methods of Formation of Chlorohydrins . I. Glyceryl Chlorohydrins . L. SMITH(Zeitsch. physikal. Chern., 1918, 92, 717-740).-The author has found that the velocity constants for the hydrolysis of chlorohydrins steadily decrease as the action pro- ceeds and has attributed this action to the presence of two (or more) isomerides in the material employed. The nature of the chloro- hydrin prepared by the various methods is not wsll investigated, and the' usual methods are not very suitable for recognising these compounds in mixtures. The rate of hydrolysis by alkali hydroxides can be used for this purpose, and from t.he ratel with which the velocity constant changes it is possible to state which isomerides are presentl. Using this method, the products obtained by the various methods for the preparation of glyceryl chlorohydrin have been examined. (1) Glyceryl monochlorohydrin, prepared from cpichlorohydrin, consists entirely of a-monochlorohydrin. (2) Monochlorohydrin from glyce'rol by the action of hydrogen Published on 01 January 1918. Downloaded 28/10/2014 00:35:27. chloride is a mixture of the a- and 8-compounds containing a large excess of the a-derivative. (3) By the action of hypochlorous acid on allyl alcohol, a mixture of the a- and 8-chlorohydrins is pro- duced which consists mainly of the P-compound. (4) The mono- chlorohydrin produced by the action of hydrogen chloride consists of a mixture of S5-90% of the a-compound and l0-15% of the P-compound. A number of experiments are described which are designed to separate1 the constituents of the mixtures. (5) Glyceryl dichlorohydrin, prepared by the action of chlorine on allyl alcohol, contains only traces of the ay-compound. (6) The product of the action of hydrogen chloride on epkhlorohydrin contains nothing but, the pure1 ay-compound. (7) The product of the action of hypochlorite on allyl alcohol contains about one-third of its weight of ay -dichlorohydrin , The whole of the hydrolytic experiments were carried out with both baryta and sodium hydroxide. J. F. S. Methods of Formation of Chlorohydrins. 11. Propylene Chlorohydrias. LENNARTSMITH (Zeitsch. physikal. Chern., 1918, 93, 59-88. See preceding abstract).-The author has prepared the propylene chlorohydrins by various methods, and has examined View Article Online ORGANIC CHEMISTRY. i. 371 the products by the kinetic method (Eoc. cit.) with the object of ascertaining their composition, and so deciding the best methods for preparing the different isomerides. (1) The product of the action of water on ally1 chloride gives pure propylene a-chloro- hydrin; (2) by the action of sulphur chloride on propylene glycol, a product containing 25% of the P-compound and 75% of the a-com- pound is obtained; (3) propylene glycol treated with hydrogen chloride yields more @-chlorohydrin than in case (2); (4) propylene oxide treated with hydrogen chloride yields mainly the a-compound with not inconsiderable quantities of the &compound ; (5) the action of hypochlorite on propylene yields a mixture of the pro- ducts. Henry’s method (A., 1903, i, 725) for converting the a-chlorohydrin into 8-chlorohydrin has been examined, and it is shown that the product consists mainly of the a-derivative. J. F. S. Autoxidation of some Derivatives of Thioncarbonic Acid. 0. BILLETERand B. WAVRE(Hdvetica Chim. Acta, 1918, 1, 167--174).--Compounds containing the group C:S, and particu- larly those of the types CS(OR)(SR), CS(OR),, CSCl(OR), and thiocarbonyl chloride, CSCl,, are phosphorescent and rapidly absorb oxygen, being thereby oxidis’ed. These substances also emit a phosphorescent vapour. The oxidation occurs only in the presence of a catalyst such as a hydroxide of the alkali or alkaline earth metals, alkali carbonates, oxides of zinc or magnesium, and ammonia. Ethyl xanthate in the presence of excess of iV/lO- ammonia solution rapidly absorbs oxygen, and about 90% of the sulphur present is converted into sulphuric acid; some of the1 com- pound, OEt*CO*SEt, is also produced. Methyl methylxanthate in the presence of N-ammonia is oxidised very rapidly, the sulphur Published on 01 January 1918. Downloaded 28/10/2014 00:35:27. being oxidised to thiosulphate, sulphite, trithionate, and sulphate, whilst hexamethylenetetramine is also f ornied. Methyl thion- carbonate, CS(OMe),, is rapidly oxidised, 38% of the sulphur being regained as sulphuric acid, whilst the rest appears as thio- sulphuric acid, sulphurous acid, and a little trithionic acid. The ethyl ester, CS(OEt),, does not undergo autoxidation in the presence of pure oxygen, but with air 40% of the ester is oxidised and 14% of the sulphur appears as sulphuric acid, whilst the rest is obtained as thiosulphuric acid, sulphurous acid and a trace! of trithionic acid. The chloro-ester, CSCl*OMe, is oxidised so rapidly that in the first half minute 837A of the theoretical quantity of oxygen is absorbed, 16.906 of the sulphur is oxidised to sulphuric acid, and the residue to sulphurous acid. Thiocarbonyl chloride is very rapidly attacked, but only about 30% is oxidised normally, the residuel being absorbed by the ammonia to form ammonium thio- cyanate and sulphur. J. F. S. Some Metallic Salts and Complex.Metallic Derivatives of $he Cyanacarboxylic Acids and their Esters. 11. LIZZIE PETTERSON-BJORCK(J. pr. Ckem., 1918, [ii], 97, 51--58).-An t2 View Article Online i. 372 ABSTRACTS OF CHEMICAL PAPERS. extension of the earlier paper (A., 1913, i, 27) giving a description of the cobalt and silver salts of cyanoacetic acid and of the platinum derivatives of methyl and ethyl cyanoacetate. Cobalt cyanoacetate, (CN*CH,-CO,),Co,H,O, obtained by the action of cyanoacetic acid on an aqueous suspension of cobalt hydroxide, forms pale red needles, the red aqueous solution of which becomes blue on warming. Silver cyanoacetate, prepared by precipitation f rorn potassium cyanoacetate and silver nitrate in aqueous solution, forms colourless needles (compare Meves, Annalen, 1867, 143, 304). By the interaction of barium cyano- acetate and chrome alum, it is possible to obtain green, prismatic crystals of a chromium cyanoacetate analogous to the ferric salt described earlier (Zoc.
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