Page:The American Cyclopædia (1879) Volume XII.djvu/142

134 NAPHTHALINE study of the substitution products of this in- teresting body. The raw material usually em- ployed in the preparation of naphthaline is coal tar, and the method recommended by Vohl is as follows: The dead oil is run into vats, and left in a cool place for six to eight days, when crystals of naphthaline are formed. The liquid portion is then drawn off, the crys- talline mass stirred up to a pap by a pestle, the adhering oil removed in a centrifugal machine, and the mass finally placed under a hydraulic press. The press cake is then transferred to an iron vessel provided with a steam coil and a stirrer, so arranged that it can be operated when the vessel is closed. The fused mass is then well mixed with a few per cent, of caus- tic soda, the lye run off, and the operation repeated three times, and finally washed with hot water until no further reaction can be per- ceived. In this manner all of the carbolic acid, creosote, resinous matter, and other im- purities are removed. The still fluid naphtha- line is then intimately mixed with a few per cent, of sulphuric acid of 45 B., the acid let off, washed out with water, and the contents of the vessel agitated with strong caustic soda and left for two or three hours to subside, at a temperature of 100 C. The naphthaline thus treated- is further purified by distillation over a free fire from cast-iron stills capable of hold- ing a ton. At first naphthaline mixed with water passes over, but at 210 C. pure naph- thaline distils, and so rapidly that 100 Ibs. can be obtained in 20 minutes. The naphthaline vapors are condensed in water at 80 C. in closed vessels placed in water baths, also kept at 80. The pure naphthaline obtained in this way is run into conical glass, metal, or moistened wooden moulds, from the sides of which it separates by contraction on cooling, and is in- troduced into commerce in sticks like brim- stone. Naphthaline, when pure, has the form of brilliant white, scaly, rhombic plates of pe- culiar odor, having a specific gravity of 1-151, according to Vohl ; a melting point, according to Kopp, of V9-2 0. ; and a boiling point of 216-4 to 216-8 0. It is in small quantities volatile at lower temperatures, and goes over copiously with steam. It possesses at first a weak, subsequently a burning taste ; is insolu- ble in cold, very slightly in hot water ; easily soluble in warm alcohol, ether, benzole, tur- pentine, volatile and fatty oils, and in acetic and oxalic acids. According to Vohl, the fused naphthaline absorbs air in the same manner as molten silver, which is richer in oxygen than the atmosphere, and gives it up again on cooling. Naphthaline dissolves indi- go, phosphorus, sulphur, succinic, benzoic, and oxalic acids, chloride of mercury, and the sul- phides of arsenic, tin, and antimony, which on cooling usually separate in a crystalline condition. Caustic potash and dilute sulphu- ric acid do not act on naphthaline, but chlo- rine, bromine, nitric acid, and concentrated sulphuric acid readily attack it. It crackles in NAPIER the hand like sulphur, and becomes negatively electric when rubbed with silk. It is destruc- tive to moths, and is used as a substitute for camphor in the protection of woollens, plants, and objects of natural history. When burned in its pure state it gives rise to copious clouds of fine lampblack. The researches of Laurent have shown the existence of a numerous series of substitution compounds, in which chlorine and bromine take the place of the hydrogen element, and sometimes replace each other. The bodies so formed are not of much practi- cal importance, but their investigation has had a remarkable influence upon the recent pro- gress of organic chemistry. A table of a few of these compounds will serve to illustrate the manner of substitution : Naphthaline ^10^8 Chlonaphtase C 10 H 7 C1 Bronaphtase C 10 H 7 Br Chloraphtese C, H 6 C1 2 Bronaphtese Ci H 6 Br 2 Chlonaphtise C 10 H 6 C1 3 Bronaphtise C 10 H 8 Br 3 Chlorobronaphtise C 10 H 6 Cl 2 Br Chlonaphtose C 10 H 4 C1 4 Chlorobronaphtcse C 10 H 4 Cl a Br 2 Chloribronaphtose C, H 4 Cl 3 Br Bronaphtose C 10 H 4 Br 4 Bromechlonaphtuse C 10 H 3 8r 2 Cl 3 Chlonaphthalase C 10 H 2 C1 6 Chlonaphthalise C 10 C1 8 Naphthalic or phthalic acid, made by the oxidation of naphthaline by sulphuric acid and black oxide of manganese, can be converted into benzoic acid, benzole, nitro-benzole, and finally into aniline ; and in this way naphtha- line is one of the sources of aniline colors. Magdala red is a dye prepared by the action of nitrous acid on naphthylamine, which in turn is derived from naphthaline. Naphthaline yellow is made by digesting 100 parts of naph- thaline for a few hours in a mixture of 200 parts of water and 20 parts of nitric acid, and dissolving the resulting crystals in ammoniacal water. Kopp's brown is produced by boiling- nitro-naphtnaline with sulphuric acid. Other compounds are naphthazarine, similar to aliza- rine, called also dianthine; naphthylamine, one of the most interesting ; Perkins's vio- let; naphthaline alcohol, or naphthole; Hoff- mann's naphthaline red; naphthyl-rosaniline ; and numerous others. NAPIER, Sir Charles, a British admiral, born at Merchiston hall, Stirlingshire, March 6, 1786, died Nov. 6, 1860. He was a grandson of the fifth Lord Napier and a descendant of the in- ventor of logarithms. ' He entered the navy in 1V99 ; in 1805 was appointed lieutenant ; in 1808 commanded the brig Recruit of 18 guns; and in April, 1809, for gallant service against the French, was made a post captain. He subsequently served with the army in Portu- gal; and between November, 1811, and June, 1815, he participated in numerous exploits on the coast of southern Italy and the North American station. After a long period of in- activity he was in 1829 employed in special service on the coast of Portugal, and in 1835