On the chemical nature of wax.―Part III. On myricine

Abstract

This paper is the last of three papers on the chemical nature of wax, and contains the investigation of that portion of bees-wax which is soluble only with difficulty in boiling alcohol. This body could never be rightly investigated before the discovery of the true nature of the other constituent of the wax, namely, the cerotic acid, for the absence of which no test was known, and the products of the decomposition of which would materially interfere with any experiments on the nature of the myricine. When the cerotic acid has been absolutely removed by repeated boiling of the wax with alcohol, a substance remains, which is saponifiable, but with difficulty. From the products of saponification the author isolated palmitic acid, C 32 H 32 O 4 , and a. new wax-alcohol, analogous to, but yet different from cerotine, described in a former paper. This alcohol, melissine, has the formula C 60 H 02 O 4 . By oxidation of this substance by means of lime and potash, the acid C 60 H 60 O, melissic acid, was obtained; and by the action of chlorine, a body analogous to chloral, a substance, that is, of the aldehyde series, but with a substitution of between fourteen and fifteen equivalents of chlorine for hydrogen. In its conversion into this substance the alcohol loses two equivalents of hydrogen, without substitution. The author also investigated the products of the distillation of myricine. From these he procured likewise palmitic acid and a solid hydrocarbon, which, rectified over potassium, had a melting-point of 62°, and contained, as shown by analysis, carbon and hydrogen in equal equivalents. The analogy of the mode of formation of this substance to cerotine from Chinese wax shows that it is the hydrocarbon, melene, C 60 H 60 . By repeated crystallization from ether a substance was obtained from the impure myricine, of a crystalline character, melting at 72°; the analysis of which agrees with the formula C 92 H 92 O 4 , which explains the reactions of the substance. The general conclusion from this investigation is, that waxes are a class of bodies which, chemically speaking, stand in the same relation to fat as fatty bodies do to the alcohol and acetic acid of vinous fermentation; all which bodies are members of one chemical series, possess an analogous chemical character, and are susceptible of analogous transformations.