Volume 1
Watts' dictionary of chemistry / revised and entirely rewritten by H. Forster Morley and M.M. Pattison Muir ; assisted by eminent contributors.
- Date:
- 1888-1894
Licence: Public Domain Mark
Credit: Watts' dictionary of chemistry / revised and entirely rewritten by H. Forster Morley and M.M. Pattison Muir ; assisted by eminent contributors. Source: Wellcome Collection.
Provider: This material has been provided by the Royal College of Physicians of Edinburgh. The original may be consulted at the Royal College of Physicians of Edinburgh.
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ABIETENE C7H10.—The heptane of Pinus sabiniana (v. Heptanes). ABIETIC ACID C44Hfi4Cv, [139°] or [165°].— Caillot, J. Ph. 16, 436 ; Maly, A. 129, 94 ; Em- merling, B. 12, 1441; Kelbe, B. 13, 888.—Oc- currence. The clear liquid turpentine of various species of pine contains abietic anhydride C44H6.,04, which, on exposure to the air, absorbs moisture and is converted into abietic acid, the liquid then coagulating to an opaque granular pulp. The anhydride is the chief constituent of common resin or colophony. Preparation.—1. Coarsely pounded colophony is digested for two days with weak spirit; the liquid is decanted from the white crystalline pulp, and squeezed in a press; the press-cake dis- solved in hot strong alcohol, and the solution left to itself at ordinary temperatures; a white crystalline crust is thus obtained; the mother- liquor, when cooled by ice, usually solidifies to a loose mass of white lamina, wdiich constitutes the greater part of the product. The crystalline crust consists of sylvic acid C2nH.!(,02, the lamina? of abietic acid (M.).—2. Colophony is digested for two days with spirit of 70 p.c, and the undis- solved portion, after washing with weak spirit, is dissolved in the smallest possible quantity of glacial acetic acid. From this solution the acid separates in crusts, and on adding a little water to its solution in hot alcohol and stirring, it is obtained in crystalline scales (E.).—3. Soda- lye which has been used for purifying crude resin-oil is mixed with common salt, and the soap which separates is dried at 70°-80°, and purified by exhaustion with ether. The residue dissolves in alcohol, and the solution, on evapo- ration, deposits needle-shaped crystals of sodium abietate, the aqueous solution of which yields, ! Vol. I. on addition of hydrochloric acid, a white pp. of abietic acid, which melts to a resinous mass if the mixture is boiled (K.). Properties. —Separates from hot alcoholic solution in irregular transparent pointed tri- clinie crystals melting at 165° (M., K.) ; 139° (E.); 135° (Fliickiger). Sol. alcohol, ether, ben- zene, glacial HOAc, CHC13 and CS.,. Reactions.—1. Abietic acid distilled with zinc chloride yields a heavy oil (70°-250°) containing heptylene (E.).—2. Strong hydrochloric and hy- drioclic acids at 145° abstract the elements of water from it, leaving the anhydride (E.) ; but when treated in alcoholic solution with gaseous HC1, it yields sylvic and sylvinolic acids : C44HH,05 + H20 = C20H30O, + C24H:)„04 (?) Sylvic acid is also formed when a hot alcoholic solution of abietic acid is mixed with sulphuric acid (M.).—3. Triturated with PC15 it yields on distillation a volatile oil C,,.,!!^, called by Maly abietone, together with HC1 and POCl3.—4. By oxidation with KMn04, abietic acid yields car- bonic, acetic and formic acids.—5. Boiled with chromic mixture, it yields large quantities of acetic and formic acids, and, after removal of these by distillation, ether extracts from the liquid a small quantity of trimellitic acid C6H3(C02H)3(E.).—6. The anhydride (colophony), oxidised with nitric acid, yields isophthalic acid, together with trimellitic acid (Schreder, B. 6, 413).—7. Abietic acid fused with potash yields propionic, but no protocatechuic, acid (M.).—8. Sodium-amalgam added to a warm alcoholic solution of abietic acid converts it into hydra- bietie acid C44H6305, a dibasic acid which forms white unctuous lamina melting at 160° (M.).—9. Abietic acid with acetic chloride or an- hydride at 160° yields an oily acetyl-compound (E.).—10. Bromine added to a solution of abietic acid in CS2 forms a bromo-derivative, probably C1|Hc.,Br„Or), which separates from alcohol as a red powder melting at 134° (E.).—11. Distilled with zinc dust it yields toluene, m-ethyltoluene, naphthalene, methyl-naphthalene, and methyl- anthracene (Ciamician, G. 9, 305, B. 11, 269). Salts.—Abietic acid is dibasic, mostly form- ing normal, rarely acid, salts. The alkaline salts are difficultly crystallisable. The normal abie- tates of the other metals C44H,j2M''05 are sparingly soluble in water, and are obtained by precipita- tion. Na2A, needles (from alcohol).—MgA, flocculent, v. sol. alcohol.—MgH2A2.—CaA.— BaA.—ZnA, si. sol. alcohol.—CuA, v. sol. CS2 or ether; pale green. Ethyl Abietate EtA, obtained by decom- posing silver abietate with ethyl iodide diluted with ether, forms a yellowish mass, having an](https://iiif.wellcomecollection.org/image/b21995990_0001_0027.jp2/full/800%2C/0/default.jpg)