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.

700/796 (page 674)

$tilling ethylamine campliorate (Wallach a. Kamenski, B. 14, 164; A. 214, 248). Allyl-imide 0gH14:O4Og:NOiH5. [49°]. Formed by heating camphoric acid with allyl thiocarbimide. Insol. water, sol. alcohol and ether. Phenyl-imide C8H14:C20.,:Nph. [116°]. Formed, together with phenyl-camphoramic acid, by warming camphoric anhydride with aniline (Gerhardt a. Laurent, A. 68, 35). Needles (from ether); insol. cold water. Di-ethyl-imido-imidine C14H21N.,0 i.e. .C = NC.,H2 C9H,X >NC.,HS (286°). S.G. 1* 1-018. \c=o Liquid; v. si. sol. water. Pps. salts of Cu and Fe. Prepared by the action of PC15 on ethyl- amine-campliorate or by the action of ethyl- amine on the chloride (C8H,^ >NEt)obtained from PC15 and camphoric-ethyl-imide. By HC1 at 200° it is decomposed into ethylamine and camphoric-ethyl-imide. Salts.—B'HCl: deli- quescent crystals. — B'HI: sparingly soluble needles.—(B'HCl),PtClr Its ethylo-iodide B'Etl: [245°]; forms long colourless prisms (Wallach a. Kamenski, B. 14, 162; A. 214, 242). Nitrile C9H14(CN)2. Formed, in small quantity, together with hydrocarbons C8HI4 and C,„H3., by distilling ammonium camphoramate with P,05 (Ballo, A. 197, 334). Crystalline ; insol. water. Camphoramic acid CsH,,(CONH2)(CO„H). So-called ' amido-camplioric acid.' The ammo- nium salt is formed by the action of NH3 on an alcoholic solution of camphoric anhydride (Laurent, Compt. chim. 1815, 147; A. 60, 326). Trimetric crystals ; m. sol. hot water, v. sol. alcohol.—NH4A' aq. [100°]. When heated with dry ZnCl2 it gives xylene tetrahydride and a ter- pene (Ballo, B. 12, 324).—PbA'2.—AgA'. Phenyl-camphoramic acid C8H, 4(CONPhH) (C02H). Formed by boiling the phenyl-imide of camphoric acid with alcoholic NHj, or camphoric anhydride with aniline. Needles (from alcohol); v. si. sol. boiling water. —AgA' (Laurent a. Gerhardt, A. 68, 36). Bromo-camphoric anhydride CO C8H13Br<^QQ^>0. From camphoric anhydride (10 g.) and Br (15 g.) at 130° (Woringer, A. 227, 3) ; an additive compound Cl0H14O3Br, appears to be first formed (Wreden, A. 163, 330). Tri- metric crystals (from chloroform). a:b:c = •8866:1:-5766. NH3 gives the imide of oxy- camphoric acid. (a)-Oxy-camphoric acid C^H^O^ Formed, together with pimehe acid, by fusing camphor with KOH (Hlasiwetz a. Grabowski, A. 145, 212). Thick liquid; the salts are amorphous. (j8)-Oxy-camphoric acid C10H16O5 Anhydride C10H14O4 i.e. C8H13(OH):C,02:0(?) CampJianic acid. [201°]. Formed by boiling bromo-camphoric anhydride with water (Kachler, A. 162, 264). Monoclinie prisms (containing aq or 2aq) (Griinling, A 227, 4) . Sublimes at 110°. Decomposed on distil- lation giving C02, lauronolic acid C„H1402, and ' campho-lactone' CBHH02. Water at 180° splits it up into C02 and CSH,, (119°).— Ba(C,0Hl3O4)2 liaq.-Cd(C10HI3O4)2 3aq. Ethyl ether EtC,0H15O5- [63°]. From bromo-camphoric anhydride and alcohol at 150°. Prisms. Imide C10H!5NO3 i.e. C8H13(0H):C.,O,:NH (?) [208°]. Amido - camphoric anhydride. From bromo-camphoric anhydride and cone. NH3Aq at 150° (Wreden, A. 163, 339). Long needles (from alcohol). Sublimes at 150°. Converted by nitrous acid into the anhydride. Oxy-camphoramic acid C10HI7NO, i.e. C8H,.)(OH)(CONH,)(C02H). ' Amido-camphoric acid.' [160°]. Formed by boiling the imide of oxy-camphoric acid with dilute KOH (Wreden, A. 163, 340). Prisms containing aq (from alco- hol). On fusion it is converted into the parent imide. Converted into oxy-camphoric anhy- dride by HN02, by cone. HClAq, or by H2S04.— CaA'22aq. ' Sulpho - camphoric acid' so - called. C,,H10SO,;. [160°-165°]. Sulphocamphylic acid. Formed, together with CO, by heating1 camphoric acid or anhydride with cone. H.,S04 (Walter, A. Ch. [3] 9, 177 ; Kachler, A. 169, 179). Triclinic prisms (containing 2aq); a:b:c = -8515:1: -7590; a = 82° 39'; 0 = 121° 10'; 7 = 111° 36' (Zepharovich, Site. B. 73, 7). V. e. sol. water, alcohol, and ether. HN03 (S.G. 1-25) converts it into C;H12S07. Potash-fusion gives C9H,202 [148^], insol. cold water, but sepa- rating from alcohol in monoclinie crystals. Salts. — (NH,),Aaq. — K,A. — CaA. — BaA. — PbH2A, 4aq : trimetric. — PbA. — BaCuA2.—Ag,A. ISOMERIDES OF CAMPHORIC ACID. Laevo - rotatory camphoric acid C^H^O,- [186°]. [a]j= -46-3° (in alcohol). Formed by the oxidation of lawo - rotatory ([<*]j= — 38°) borneol, or the corresponding camphor, by heat- ing for several hours with a large excess of HN03 (S.G. 1-27) (Chautard, C. R. 37, 166; Haller, C. B. 103, 64). Besembles camphoric acid in all respects except that its rotation though equal is opposite. Inactive camphoric acid (C10H1(1O4)o. [204°]. S. 1; S. (alcohol) 33; S. (ether) 28 (O). Formed by heating inactive camphor with HN03 at 100°, or by mixing equal weights of dextro- and Ifevo-camphoric acids (Chautard, C. R. 56, 698; Armstrong a. Tilden, C. J. 35, 757; Haller, C. R. 105, 66). Less soluble than its isomerides. Diethyl ether Et2A. (270°-275°). S.G. 1-03 (C). Anhydride (C10H,4O3).,. [223°] (A. a. T.). S. (chloroform) 25 ; S. (ether) 4 ; S. (alcohol) 1-5 (C). Formed by heating the acid. An inactive camphoric acid [186°] was ob- tained by Muir (C. J. 37, 685) by oxidising the camphor of oil of sage. Meso-camphoric acid C|fJH,604- [113°]. Formation.—1. Formed, by heating dextro- camphoric acid (5 g.) with (20 c.c.) fuming HC1 at 140° for 30 hours (Wreden, Z. [2] 7, 419; A. 163, 328 ; B. 6, 565).—2. By heating dextro- camphoric acid (5 g.) with HI (30 c.c. of S.G. 1-6) at 160°.—3. By heating camphoric acid with water at 200° (Jungfleisch, B. 6, 268, 680). 4. Together with ' sulphocamphoric acid ' by the$