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

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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$10. With iodine chloride acetone yields C:)H.,LO (Maxwell Simpson, Laboratory, p. 79).—11. Electrolysis of a mixture of acetone and dilute sulphuric acid produces acetic, formic, and car- bonic acids (Friedel, J. 1859, 338).—12. By chromic acid mixture it is oxidised to acetic and carbonic acids.—13. Acetone heated with ammonia, yields a mixture of three bases, the composition and mode of formation of which are indicated by the following formula?:— Diaeetouamine .... C„H,1N0 = 2C.,H..0+NH3- H30 Triacetonamine .... C3H„N0 = 3C3HoO + NHa-2H„O Dehydrotriacetonamine . C„H15N = CaH,,NO - H,0. With mcthylamine, in like manner, acetone yields methyldiacetonamine C,H,,NO and other bases. With dimethylamine only dimethyldi- acetonamine CsHnNO.—14. With hydroxyla- mine, acetone forms acetoxim [q.v.] Me;C:NOH, which crystallises in prisms [60°], (135°).—15. Sodium strongly attacks acetone, with forma- tion of crystallisedpinacone hydrateC6H120 7H..0 and liquid phorone C„H, ,0 thus: 2C3H60 + Na.,= Na.,0 + C„H,.,0, and 3C.,HsO - 2H..0 C^.O (Stiideler, A. Ill, 277).—16. Heated with ani- line hydrochloride at 180° it forms di-methyl- quinoline (Engler a. Riehm, B. 18, 2215, 3296). —17. Caustic alkalis, e.g. KOH and CaO, exert a dehydrating action on acetone and form con- densation-products varying in composition, ac- cording to the proportion of water abstracted, viz.: B. P. Xylite-napbthaC,.Ha,0,=4C1H.O—HaO .. 110c-120° Mesitvl oxide CrH,,,6 = 2C1HliO-H..O .. .. 131° Mesitylene .. C„H13 = 3C,HrO-3H30.. 155°-160° Phorone.. .. C„H, ,O = 3C,H60—2H..O.. 216°-220° Xylite-oil .. C12H1„0=4aiH60—3Ha0 above 250° Vapour of acetone passed over strongly heated KOH or potash-lime is resolved into methane and carbonic acid, C3H^O + 2KOH = K.,C03 + 2CH,. At a lower temperature the chief products are acetic acid, formic acid, and hydrogen, C.,H60 + 2KOH + H.,0 = KC.2H.,0., + KCHO., + 3H, (Dumas a. Stas, A. Ch. [2] 73,149 ; Persoz, Rev. Sclent. 1, 51).—18. Acetone heated with ZnCL yieldshexa-methyl-benzene C6Mes (W.H.Greene, C. R. 87, 931).—19. Gently heated with A1CL,, it yields mesityl oxide, phorone, and other products (Louise, C. R. 95, 602).—20. Dry PtCl, dissolves in acetone, and the solution when evaporated leaves a brown resinous mass containing a yellow crystalline substance, CbHlaOPtCl, (?), called Acechloride of Plati- num, or Chloroplatinite of Mesityl (Zeise, A. 33, 29).—21. On adding HC1 to a mixture of acetone, with potassium cyanide and sulpho- cyanide, the compound C-H;0;NS is obtained. This compound heated with HC1 is resolved into CO.,, NH„ and o-oxy-iso-butyric acid. With silver nitrate it yields C5H,AgO.,NS (Urech, B. 6, 1113).—22. By action of alkalis or of HC1- gas on a mixture of 1 mol. acetone and 2 mol. benzaldehyde, dibenzylidene -acetone (q.v.) PhCH:CH.CO.CH;CHPh is obtained (Claison a. Claparede, B. 14, 349). By the action of alkalis on a solution of o-nitro-benzaldehyde in acetone, methyl o-nitro-^-oxy-^-phenyl-ethyl ketone [68°] is formed according to the equation NO.,.C„H,.CHO + CO(CH,).,= NO ...C.H ,.CH(OH).CH,.c6CH, (Baeyer a. Drewsen, B. 15, 2856).—The corre- sponding jxzra-compound [58°] is obtained in like manner from acetone and p-nitro-benzalde- hyde (Baeyer a. Becker, B. 16, 1968).—23. With fiufiiraldehyde, acetone forms a compound crystallising in long white needles [37°] (J. G. Schmidt, B. 14, 574)—v.Fubfurylidene-acetone. 24. With pyrrol in presence of HC1 it forms CnH^N,, [291°] (Baeyer, B. 19, 2184). Combinations. — 1. With Bisulphites. Formed by direct combination. C3H(i(OH)S03NH4 crystallises in lamina? (Stiideler, A. Ill, 307)— C3Hu(OH)S03Na.—Lamina?, moderately soluble in water, less in alcohol. Gives off acetone when boiled with aqueous sodium carbonate (Limpricht, A. 93, 238)—C3H, (OH)S03K (L.). 2. With Mercuric Oxide 2C3H(iO 3HgO. Formed by mixing acetone with mercuric chloride and weak potash-lye, dialysing the filtered liquid, and precipitating the liquid remaining in the dialyser with acetic acid.—Gelatinous precipitate which becomes resinous on drying. Its solu- tion gelatinises when heated or when merely left at rest (Emerson Reynolds, Pr. 19, 431). Formed also by dissolving HgO in acetone (Kutscheroff, B. 17, 20). Acetone-boric Acid, C3H(jO(BHO)., [50°]. Formed together with (a) and (/3) acetone-fluo- boric acid, and hydrocarbons, on saturating acetone with boron fluoride and distilling the pro- duct, (a) Acetoncfluoboric acid, C3H„0 3HFB404 (120°-123°); the isomeric (#) modification [36°] (90°-92°) forms shining white lamina?. All three compounds fume in the air, burn with green flame, and are quickly decomposed by water, yielding boric acid and acetone hydro- fluoric acid (Landolf, C. R. 89, 173). Acetone-hydrofluoric Acid C3H0OHF (55°) obtained by fractional distillation from the pro- duct of the action of water on acetone-fluoboric acid. An inflammable liquid with pleasant ethereal odour (Landolf, C. R. 96, 580). Another compound, C3H(jO 2HF (-12°) is gaseous at ordi- nary temperatures. Acetone-sulphonic Acid CH3.CO.CH,,.S03H. Formed as K-salt by treating dichloracetone (118°) with a strong solution of potassium sul- phite : C.H.CL.O + K.,SO.t + H.,0 = K,S04 + HC1 + C3H5C10, and C3H5C10 + K,S03 = KC1 + C:)H5O.S03K. The K-salt may be extracted from the product by boiling alcohol, and separates therefrom in white lamina?. Very soluble in water, not de- composed by boiling with dilute acids. Boiled with strong potash-lye, it yields sulphite and perhaps an acetone-alcohol (Bender, Z. 1870, 162 ; B. 4, 517). Salts.—KA' Plates (from alcohol V. e. sol. water—BaA'„ aq. Plates.—PbA': aq. [140°]—CuA'., l£aq. Greenish plates. Acetone-phosphorous Acid C3H6O.PO._,H. Remains on distilling acetone with I and P. (CjHsO.PO.^.Ba is amorphous, soluble in water, insoluble in alcohol (Mulder, J., 1864, 329). Acetone-cyanhydrin CH,.C(CN) (OH).CH, (Oxyisobutyronitrile). Formed by the action of aqueous HCN (20 p.c.) on acetone, or by the action of nascent HCN on acetone diluted with ether. It is very unstable, for even on evaporation of its solution it changes into di-acetone-cyan- hydrin with evolution of HCN (Tiemann a. Friedlander, B. 14, 1970). Alcoholic NH3 at 60° converts it into a-amido-iso-butyronitrile CH3.C(CN)(NH.,).CH, whence HC1 forms a-amido-$