Properties. - Antiseptic, antipyretic, antirheumatic.

Uses. - Rheumatism, neuralgia, lancinating pains, diarrhoea, dysentery, cholera, ulcers, ozaena, diphtheria, gonorrhoea, otorrhoea, vesical catarrh, fermentative dyspepsia, typhoid fever, cystitis, substitute for iodoform in surgery. Salol in the small intestine splits into phenol 36 p. c. and salicylic acid 64 p. c, consequently salol is more dangerous than salicylic acid from the presence of phenol, which latter colors the urine dark. Death has been occasioned by gr. 15 (1 Gm.), and by gr. 120 (8 Gm.), in each case signs of phenol- (carbolic acid) poisoning being present.

Phenolphthaleinum. Phenolphthalein, C20H14O4. - (Syn., Phenol-phthal., Dihydroxyphthalophenone, Dioxythiphenylphthalide, Para-phthalein; Fr. Phenolphtaleine; Ger. Phenolphthalein.)

II Aromatic Series 979

Manufacture: This dibasic phenol derivative is obtained by heating phenol (10), phthalic anhydride (5), and sulphuric acid (4) at 120° C. (248° F.) for 10 hours, boiling product with water, dissolving residue in sodium hydroxide solution, precipitating phenolphthalein with acetic acid; purify by washing, dissolving in alcohol, boiling with animal charcoal, reprecipitating with water. It is a white, faintly yellowish-white, crystalline powder, odorless, tasteless, permanent, soluble in alcohol (13), ether (70), solutions of alkali hydroxides and carbonates with red color (decolorized by excess of acids or heating with zinc dust), almost insoluble in water, melts at 253° C. (487° F.); incinerate 2 Gm. - ash .05 p. c. Impurities: Heavy metals, fluorane, resinous substances, etc. Dose, gr. 1.5-3 (.1-.2 Gm.), powder, cachet, capsule, pill; Gr. 8(.5 Gm.) given with safety in obstinate cases, but gr. 15 (1 Gm.) have poisoned. With sugar and vanilla as proprietary Purgen, etc.

Preparation. - (Unoff.): Trochisci Phenolphthaleini, 1 gr., + acacia 1.5, sugar 13,. vanillin .003, carmine .001, water q. s.

Properties and Uses. - Purgative, with no other apparent physiological action; indicator in volumetric analysis.

Trinitrophenol. Trinitrophenol, C6H2(OH)(NO2)3. - (Syn., Trini-trophen., Picric Acid, Acidum Picricum (Carbozoticum), Carbozotic Nitrophenisic) Acid; Fr. Acide picrique (carbazotique, nitroxaothique); Ger. Pikrinsaure, Trinitrocarbolsaure.)

Manufacture: Formerly by action of nitric acid on indigo, silk, leather, wool, aloes, benzoin, salicin, etc.; now by mixing phenol and sulphuric acid equal parts, and, after phenolsulphonic acid forms, adding nitric acid, constantly stirring, crystallizing; may purify by removing adhering acid in a centrifuge, dissolving in sodium hydroxide solution, decomposing sodium picrate with hydrochloric acid, crystallizing, recrystallizing. It is in pale yellow, rhombic prisms, scales, odorless, intensely bitter taste; explodes when heated rapidly, or subjected to percussion; soluble in water (78), boiling water (15), alcohol (12), chloroform (35), ether (65), benzene (10); aqueous solution acid, melts at 122° C. (252° F.). Tests: 1. Aqueous solution (1 in 100) yellowish, darker with alkalies, red with ammonium sulphide T. S. or solution of an alkaline cyanide. 2. Dissolve 2 Gm. in 50 Ml. (Cc.) of benzene - the washed and dried insoluble residue .2 p. c. Impurities: Sulphate, etc. For safety in transportation usually mixed with 20 p. c. of water, and before applying tests should be dried to constant weight over sulphuric acid. Should be kept cool, remote from fire, in well-stoppered bottles. Dose, gr. 1/2-2 (.03-.13 Gm.); ammonium picrate (best salt), gr. 1/2 (.03 Gm.), ter die.

Properties and Uses. - Antiseptic, analgesic, antiperiodic, parasiticide, poisonous; solution locally in fungous endometritis, erysipelas, lymphangitis, fissured nipples, burns, scalds (1 + alcohol 10, + water 730); solution in water (1 in 100) precipitates (test) alkaloids (except aconitine, caffeine, cocaine, coniine, hyoscyamine, morphine, theobromine); popular yellow dye, modified into green with indigo or Prussian blue.

Poisoning: Imparts color to urine and all tissues, produces low temperature, weakness, vomiting, purging, collapse, convulsions, death; increases white but partly dissolves red blood corpuscles.

5. Naphthalene Derivatives. Betanaphthol. Betanaphthol, C10H7OH. - (Gr. 8. second letter of alphabet - Beta +

II Aromatic Series 980

L. naphth (a) + ol(eum) - i. e., second of several isomeric compounds from this origin.) (Syn., Betanaph., Naphthol, Naphtol, Beta-mono-hydroxy-naphthalene, Iso-naphtol; Fr. β-Naphthol; Ger. Naphtholum.)

II Aromatic Series 981

Betanaphthol, C10H7OH.

II Aromatic Series 982

Naphthalene, C10H8.

Manufacture: This monohydroxyphenol of the naphthalene series occurring in coal-tar usually is prepared artificially from naphthalene by heating it with sulphuric acid to form α- and β-naphthalenesul-phonic acids, C10H7HSO3, the former, produced at about 90° C. (194° F.), being converted into the latter at higher temperature; dissolve in water, saturate with milk of lime to form calcium naph-thalenesulphonates which crystallize out; dissolve this in water and decompose by sodium carbonate to get corresponding sodium salts, now fuse with sodium hydroxide, yielding sodium naphthol and sodium sulphite, when the former may be treated with hydrochloric acid to form sodium chloride and betanaphthol, which is purified by sublimation and recrystallization from water; it bears the same relation to naphthalene as does phenol to benzene. It is in colorless, pale buff, shining crystalline laminae, or white, yellowish crystalline powder, faint phenol-like odor, pungent taste, permanent, soluble in water (1000), boiling water (80), alcohol (.8), chloroform (17), ether (1.3), glycerin, olive oil, alkali hydroxide solutions, melts at 121° C. (250° F.), sublimes, volatilizes with alcohol, water; hot saturated aqueous solution neutral. Tests: 1. Cold saturated aqueous solution + ammonia water - faint bluish fluorescence; + ferric chloride T. S. - greenish, slowly separating whitish flakes, brownish on heating. 2. Add .1 Gm. to 5 Ml. (Cc.) of aqueous solution of potassium hydroxide (1 in 4), + 1 Ml. (Cc.) of chloroform, warm gently - aqueous layer blue, green, brown, incinerate 2 Gm. - ash .05 p. c. Impurities: Naphthalene, alphanaphthol, organic substances. Should be kept dark, in well-closed containers. Dose, gr. 2-5 (.13 - .3 Gm.).