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The Sp. Gr. of the Cresols is also lower than Phenol.
The presence of 1.3% of Cresol in Phenol reduces the M. P. 8° C. or to about 31.5° C., according to some authorities.
The presence of water, even in Crystalline Phenol, materially affects the melting and boiling points. As much as 5% of water may be present in Crystalline Phenol and the fusing point materially lowered in consequence.
There is considerable literature on Carbolic Acid in general, and especially on its manufacture from Coal Tar distillates. Most of this work has been reviewed, covered and exhaustively treated on, in Lunge's Coal Tar and Ammonia, Part II, 1909.
The literature on synthetic Phenol, however, is more limited and frequently confined to only a few lines or paragraphs, in the most of the descriptions. Some of the accounts are found in the following, which are the sulfonation process.
Wurtz, Dusart and Kekule, in 1867, discovered simultaneously, that on fusing Benzene-monosulphonic Acid with Caustic Potash, that Potassium Phenate and Sulphite are produced; upon decomposing the Phenate, Phenol results.
Caustic Potash being higher priced, Caustic Soda is used instead.
G. Schultz, Die chemie des Steinkohlentiers, 1900, Vol. I, 139.
Allen (Com. Org. Anal., Vol. III, 1910, 289), giving two methods for the synthesis of Phenol.
Cain and Thorpe, Synthetic Dyestuffs, 1913.
Jayne, Am. Jour. Pharm., Dec., 1891, and J. S. C. I., 1892, 264.
Wahl and Atack, Organic Dyestuffs, 1914.
Phenol can be produced artificially from Benzene, by oxidation with nascent Oxygen, or even with free Oxygen (Friedel and Craffts, Bull. Soc. Chim., XXXI, 463).
An account of the synthesis of Phenol from Acetylene is given by Berthelot (Compt. rend., 1898, (23), 908-911), and abstracted (J. S. C. I., 1898, 127), and also (Annalen, 154, 132), (G. Schroeter, Annalen, 303, (1), 114-132).
Phenol is also obtained by the oxidation of Aniline. The process being as follows:
Pure Aniline Oil, preferably that grade called "Aniline for blue,” is dissolved in water in a lead lined tank, covered with a hood and provided with stirrers and leaden steam coils.
The solution is acidified very strongly with Sulphuric acid, and to the hot liquid a solution of commercial Sodium Nitrite is gradually added, when Phenol is at once formed.
In this reaction the Sodium Nitrite in contact with the acid solution, liberates Nitrous acid, which forms Diazobenzene Sulphate with the Aniline Sulphate.
2(C. H, N H,) + H, S 0, + 2(H N 02) = = 2(C, H, N) S 0.+
but as the solution is hot, the Diazo compound at once decomposes with the formation of Phenol, and evolution of Nitrogen.
2(C, H, N) S 0. + 2(H, 0) = 2(C, H, OH) + H2SO, + 4 N
The only practical and economical way, however, is by the Sulphonation process, starting with Benzol.
Phenol is used in the manufacture of Picric Acid.
Schmidt & Glutz (Mon. Sci., 1878, 1115; Ber., 2, 52), (French Pat., 345,441).
Laurent (Ann., 1843, 43, 208).
(Martins., Ind. Chem., Vol. I, p. 632), Fay (Coal Tar Dyes, 1911).
Phenol is used in producing Coralline or Aurine.
Zulkowski (M. f. Ch., 1895, 358-403), Runge (Berz. Jahresber., 15, 423), Schultz (Die Chemie des Steinkohlentheers, 2nd Edit., II, 515).
Phenol is used in Azo colors, in Oxidised Triphenylmethane colors, and in the Salicylates. It is used as a disinfectant, for antiseptic purposes, as a preservative of beet juice (Cunisset Bull. Soc. Chim., 1874, XXI, 47) and (Hulwa, Wagners Jahresber., 1875, 795), and for destroying Lactic Acid ferment in the manufacture of Alcohol (Maercker, Wagners Jahresber., 1872, 826).
Kellner (Chem. Zeit., 1884, 122) found it a good remedy for the parasitic diseases of plants and animals, and manure containing 2% of it is harmless to the plants, except when put on the field with their seeds.
Kletzinsky (Wagners Jahresber., 1864, 601) showed that it possessed tanning properties, and Baudet (Wagners Jahresber., 1870, 669) obtained a patent for the same purpose.
Harcke (Ger. Pats., 16,022 and 19,633) adds Phenol in the currying process, and produces artificial leather with Phenol as one of the ingredients.
Shaw (Ger. Pat., 27,270), and Beda (British Pat., 16,647, 1886) proceed in the same manner.
Sodium Phenolate prevents dry rot in timber, and is also used in the manufacture of lining stones for converters (Hustener Gewerkschaft, Z. angew. Chem., 1889, 132).
The Neue Augsburger Kattunfabrik (Ger. Pat., 95,692) employs a weak solution of Phenol in calico printing.
Gassmann and the Usines du Rhone (Ger. Pat., 99,756) employ Phenol for dissolving coloring matters insoluble in water.
Justin Mueller (Bull. Soc. Ind., Mulhous, Vol. 76, p. 72) finds that an addition of Phenol to the colors for printing on wool has the same effect as chlorinating the wool.
Phenol is a solvent for Casein, and numerous patents have been taken out by B. B. Goldsmith covering its application in thermo-plastics.
Phenol and Formaldehyde are the principal constituents of the Phenol-Aldehyde condensation products, or synthetic resins, now so generally used and designated as Bakelite and Condensite. The latter is the important constituent of the Edison Disk Talking Machine Records. Numerous patents cover the many variations in these synthetic Resins and the Varnishes and Lacquers made from them. (See A. Luft, L. H. Baekeland, H. Lebach, J. W. Aylesworth, De Laire, Wetter, Knoll & Co., Blumer, Bayer, Kleeberg, Smith and Story). See Balkeland (J. S. C. I. (3), 1909; (8), 1909; (12), 1911; (10), 1912; (6), 1913 (2), 1916: Trans. Am. Electrochemical Soc. 1909, 593).
Phenol is combined with soap, and one of its common designations is Creoline.
Lysol is a water soluble preparation of Phenol, another
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designation for it is Sapocarbol.
Anthrasol is a preparation of Tar-Oils containing Phenol, and used for therapeutic purposes.
Lysoform is Lysol and Formaldehyde.
Non-poisonous disinfectants called Oxychinaseptol or Diaphtherin are made from Phenol and Oxyquinoline.
Solveol for surgical purposes is Sodium Salicylate and Cresol.
The Sozoiodols of Trommsdorf unite the action of Iodoform with that of Carbolic Acid in the treatment of wounds.
Phenosalyl is a mixture of Carbolic Acid, Salicylic Acid, Lactic Acid, Menthol, Glycerin and Borax.
Microsol is a solution of Cupric Sulphate containing free Sulphuric Acid and 10% Cupric Phenolsulphonate.
Sanatolyse consists of Carbolic Acid, Sulphuric Acid and Ferrous Sulphate.
Metakalin in the form of tablets contain Phenol (B. P. 9953, 1904).
Sozal (Scherges, Pharm. Zeit., 1892, 489) is Aluminum paraphenosulphonate and more efficacious than Aluminum Acetate in the treatment of ulcers.
Salol is Salicylic Acid fused with Phenol and then heated with Phosphorus Oxychloride (Neucki), it is Phenylate of Salicylic Acid.
Aspirin is Acetylsalicylic Acid and is made by heating Salicylic Acid with Acetic Anhydride, or Acetyl Chloride, and recrystallizing from Chloroform. (U. S. Pat., 749,980), (Eng. Pat., 15,517, 1902.)
Phenol-Zinc solutions are used in preserving timbers from decay and dry rot (Chem. Zeit., 1885, 602).
Phenol yields Phenol Carboxylic Acid with Carbon Tetrachloride and Sodium Hydroxide.
Phenol Aldehydes are produced from Phenol, Chloroform and Caustic Soda (Salicylaldehyde).
Phenol condenses with Formaldehyde to Phenol Alcohols (Seligenine).
Heating Phenol with Malic Acid and Sulphuric Acid produces Coumarine.
Dyestuffs belonging to the Aurine series are obtained from Phenol and Benzotrichloride.
Hydrogen Dioxide converts Phenol into Catechol, Hydroquinone and Quinone.
By the action of Fused Sodium Hydroxide on Phenol, Phloro