Methods of analyzing for isobutene, methyl /-butyl ether and /-butyl alcohol in aqueous methanol solutions are described. These methods are then used to determine the fractions of these substances that are produced in the solvolysis of /-butyl chloride in aqueous methanol solutions at several compositions and temperatures.The products of solvolysis of ¿-butyl chloride in aqueous methanol solutions are methyl ¿-butyl ether, ¿-butyl alcohol and isobutene. The purpose of the work presented here has been to determine (1) This work was supported in part by the Office of Naval Research. United States Navy.(2) This is the second in a series of papers dealing with the solvolysis of /-butyl compounds in aqueous organic solvents; see Cropper, Spieth
Notes 5255 not proceed by the primary mechanism alone. Drops of diethyl phthalate have been identified in the decomposition apparatus, which suggests dissociation according to equation 7 ZrCl4-C«H4(COOC2H5)2-> ZrCh + CelLCCOOCiHsh (7)It is possible that the ethylene results from the decomposition of the ester, as reported for ethyl benzoate.1 2345 *If this is so, the phthalic acid, resulting from equation 8, would react with any free metal tetrachloride to give hydrogen chloride.C6H4(COOC2H5)2 ->-C6H4(COOH)2 + C,H4 (8) ZrCl4 + C,H4(COOH)2 -*-ZrCl2(OOC)2CtH4 + 2HC1 (9) In the zirconium case only, trace quantities of phthalic anhydride were identified among the decomposition products.Acknowledgment.-This work was supported in part by the U. S. Atomic Energy Commission under Contract No. AT-(40-l)-234.
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