As previously stated, all organic compounds are either derivatives of methane, CH4 (fatty series), or of benzene, C6H6 (aromatic series), and while these two parental compounds are strictly hydrocarbons, they as well as their derivatives are thoroughly distinctive, as they cannot in any sense be substituted for or converted into one another. The members of the fatty series, in a degree, are products that might be used as animal food; those of the aromatic series have not this power, being simply aromatics, antiseptics, stimulants. Many compounds of this latter series are obtained directly from the vegetable kingdom, while a great number result indirectly therefrom by destructive distillation of coal in the manufacture of illuminating gas, giving us coal-tar, pix lithanthracis, soluble in benzene, carbon disulphide, chloroform, ether; liquor picis carbonis - coal-tar 20 p. c, quillaja 10, alcohol q. s. 100; externally, antiseptic, parasiticide; chronic skin affections; ointment - 5-10-20-30 p. c. When this coal-tar is distilled and the distillate caught in water, it separates into two layers - light oil floating on top of the water, heavy oil sinking below the water: from the former come benzene, etc.; from the latter, phenol (carbolic acid), etc.

Benzenum. Benzene, C6H6. - (Syn., Benzol, Benzole, Phenyl Hydride, Coal Naphtha; Fr. Benzene; Ger. Benzen.) A mixture of homologous hydrocarbons, chiefly benzene, CeH6, 70 p. c. + toluene, C6H5,CH3, 20-30 p. c.

Manufacture: Distil coal-tar, when water and ammonia pass over along with 8-10 p. c. of a brown liquid, light oil; later the dead oil is obtained containing aniline, quinoline, naphthalene, phenol (carbolic acid), etc. The light oil contains benzene, toluene, xylene, isocumene, these being separated by fractional distillation, benzene coming over at

80° C. (176° P.), toluene at 110° C. (230° F.), which may be purified by exposing to a low temperature and expressing the portion remaining liquid. It is a thin, colorless, very inflammable liquid, coal-gas odor, sp. gr. 0.884, congeals at 0° C. (32° F.), soluble in ether, chloroform, acetone, alcohol (4), with nitric acid readily converted into nitrobenzene. Impurities: Acetylene, thiophene, carbon disulphide, toluene, xylene, etc.

Properties and Uses. - Antispasmodic, anticatarrhal, antizymotic, germicide, poisonous (causing uncertain gait, mental disturbance, wandering delirium, vertigo, loss of sexual power, epileptic convulsions, deep sleep). Used in whooping-cough, influenza; solvent for fats, volatile oils, resins, caoutchouc, sulphur, phosphorus, iodine, alkaloids (quinine, etc.). Its principal use, however, is in the manufacture of aniline, and therefrom the many important coal-tar products. Dose, ex-30 (.6-2 Ml. (Cc.)), emulsion on sugar, in capsule; locally mixed with 9 parts of soapsuds.

Phenol. Phenol, C6H5OH. - (L. fr. Gr.

II Aromatic Series 966

to show, or

II Aromatic Series 967

purple-red + ol(eum).) (Syn., Carbolic Acid, Acidum Carbohcum, Acidum Phenicum - Phenylicum (Crystallizatum), Phenic - Phenylic Acid, Phenylic Alcohol, Benzophenol; Fr. Acide carbolique - phenique, Hydrate de Phenyle; Ger. Karbolsaure, Phenylsaure, Phenylalkohol.) This hydroxybenzene, obtained from coal-tar or made synthetically, is the alcohol of the hydrocarbon benzene, and according to the number of hydrogen atoms replaced by the hydroxyl, OH, we have mon-, di-, tri-atomic, etc., phenols or alcohols. This hydroxyl here is acid, whereas that in methane alcohols is basic; these phenols or phenol alcohols differ from common alcohols in not yielding aldehydes or acids by oxidation and in having hydroxyl (OH) that is acid.

II Aromatic Series 968

Benzene.

II Aromatic Series 969

Phenol (Carbolic Acid).

Manufacture: Phenol occurs in castoreum, urine and in products of dry distillation of bones, resins and wood, especially coal; that portion of coal-tar coming over at 100-250° C. (212-482° F.) is known as light oil, sp. gr. 0.940-0.990, and contains phenol 4-10 p. c. This fraction is agitated with a 10 p. c. solution sodium hydroxide (stronger solution undesirable, as it would dissolve also naphthalene, etc.), and upon standing separates into two layers - lower, being a solution of sodium-phenol - upper, consisting of the extracted oil; draw off and 54 treat lower layer with hydrochloric or sulphuric acid sufficient for exact decomposition; the impure phenol thus liberated rises to the surface as an oily layer, which is removed and washed by agitation with concentrated solution sodium chloride, freed from water by calcium chloride, then distilled at 180-190° C. (356-374° F.); expose distillate to cold, when phenol congeals in crystalline mass, which freed from adhering liquid is again distilled at 185° C. (365° F.) and crystallized. Sometimes before final distillation it is treated with potassium dichromate and sulphuric acid, and to get colorless loose crystals may recrystallize from boiling petroleum benzin. Phenol may also be obtained from the heavy oil, collecting that portion coming over at 160-220° C. (320-428° F.), then treating distillate as above. Phenol may be obtained synthetically from benzene (benzol) by treating with sulphuric acid, heating - C6H6 + H2SO4 = C6H5SO2OH + H2O; the resulting benzene-sulphonic acid is neutralized with potassium carbonate, yielding potassium benzene-sulphonate, and this compound fused with excess of potassium hydroxide - 2(C6H5SO2OK) + 4KOH = 2H2O + 2K2SO3 + 2C6H5OK, the latter, potassium-phenol, is treated with solution hydrochloric acid, which liberates phenol, to be purified by distillation - C6H5OK + HC1 - C6H5OH + KC1. This process has the advantage of yielding phenol free from cresol, xylene, etc., as benzene can be used of absolute purity. It is in colorless, interlaced, or separate needle-shaped crystals, or white, crystalline mass, sometimes acquiring reddish tint, characteristic, aromatic odor, copiously diluted with water sweetish taste, slightly burning aftertaste, when undiluted cauterizes and whitens skin and mucous membrane, soluble in water (15), alcohol, glycerin, chloroform, ether, carbon disulphide, fixed or volatile oils; aqueous solution (1 in 15) clear, neutral, faintly acid, liquefied by gentle heat, forming a highly refractive liquid, or by 8 p. c. of water, congeals at 38° C. (100° F.); contains 97 p. c. of pure phenol. Tests: 1. Aqueous solution with bromine water - white precipitate (tribromphenol), at first redissoly-ing, but permanent with more reagent, appearing crystalline under the microscope. 2. Aqueous solution (1 in 100) 10 Ml. (Cc.) + 1 drop of ferric chloride T. S. - violet-blue liquid. 3. Heat on water-bath 10 Gm. - volatilizes with residue .05 p. c; vapor inflammable. Should be kept dark, in well-closed containers. Dose, gr. 1/2-l (.03-.06 Gm.).