α-naphthoquinane-oxime, formed by the action of nitrous acid on
α-naphthol or of hydroxylamine hydrochloride on α-naphthoquinone
(H. Goldschmidt and H. Schmidt, Ber., 1884, 17 p. 2064); and
2-nitroso-α-naphthol (β-naphthoquinone-oxime), formed by the action
of hydroxylamine hydrochloride on β-naphthoquinone.
NAPHTHYLAMINES, or Aminonaphthalenes, C10H7NH2, the naphthalene homologues of aniline, in contrast to which they may be prepared by heating the naphthols with ammonia-zinc chloride.
α-Naphthylamine is prepared by reducing α-nitronaphthalene with iron and hydrochloric acid at about 70° C., the reaction mixture being neutralized with milk of lime, and the naphthylamine steam-distilled. It may also be prepared (in the form of its acetyl derivative) by heating α-naphthol with sodium acetate, ammonium chloride and acetic acid (A. Calm, Ber., 1882, 15, p. 616); by heating α-naphthol with calcium chloride-ammonia to 270° C.; and by heating pyromucic acid, aniline, zinc chloride and lime to 300° C. (F. Canzonieri and V. Oliveri, Gazz., 1886, 16, p. 493). It crystallizes in colourless needles which melt at 50° C. It possesses a disagreeable faecal odour, sublimes readily, and turns brown on exposure to air. Oxidizing agents (ferric chloride, &c.) give a blue precipitate with solutions of its salts. Chromic acid converts it into α-naphthoquinone. Sodium in boiling amyl alcohol reduces it to aromatic tetrahydro-α-naphthylamine, a substance having the properties of an aromatic amine, for it can be diazotized and does not possess an ammoniacal smell. Since it does not form an addition product with bromine, reduction must have taken place in one of the nuclei only, and on account of the aromatic character of the compound it must be in that nucleus which does not contain the amino group. This tetrahydro compound yields adipic acid, (CH2)4(CO2H)2, when oxidized by potassium permanganate. The α-naphthylamine sulphonic acids are used for the preparation of azo dyes, these dyes possessing the important property of dyeing unmordanted cotton. The most important is naphthionic acid, 1-amino-4-sulphonic acid, produced by heating a-naphthylamine and sulphuric acid to 170–180° C. with about 3% of crystallized oxalic acid. It forms small needles, very sparingly soluble in water. With diazotized benzidine it gives Congo red.
β-Naphthylamine is prepared by heating β-naphthol with zinc chloride-ammonia to 200–210° (V. Merz and W. Weith, Ber., 1880, 13, 1300); or in the form of its acetyl derivative by heating β-naphthol with ammonium acetate to 270–280° C. It forms odourless, colourless plates which melt at 111–112° C. It gives no colour with ferric chloride. When reduced by sodium in boiling amyl alcohol solution it forms alicyclic tetrahydro-β-naphthylamine, which has most of the properties of the aliphatic amines; it is strongly alkaline in reaction, has an ammonia cal odour and cannot be diazotized. On oxidation it yields ortho-carboxy-hydrocinnamic acid, HO2C·C6H4·CH2·CH2·CO2H. Numerous sulphonic acids derived from β-naphthylamine are known, the more important of which are the 2·8 or Badische, the 2·5 or Dahl, the 2·7 or δ, and the 2·6 or Bronner acid. Of these, the δ-acid and Bronner’s acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs.
NAPIER, SIR CHARLES (1786–1860), British admiral, was the second son of Captain the Hon. Charles Napier, R.N., and grandson of Francis, fifth Lord Napier. He was born at Merchiston Hall, near Falkirk, on the 6th of March 1786. He became a midshipman in 1800, and was promoted lieutenant in 1805. He was appointed to the “Courageux” (74), and was present in her at the action in which the squadron under Sir J. B. Warren took the French “Marengo” (80) and “Belle Poule” (40), on the 13th of March 1806 in the West Indies. After returning
home with Warren he went back to the West Indies in the
“St George” and was appointed acting commander of the
“Pultusk” brig. The rank was confirmed on the 30th of
November 1807. In August 1808 he was moved into the “Recruit” (18), and in her fought an action with the “Diligent” (18), in which his thigh was broken. In April 1809 he took part in the capture of the “Hautpoult” (74), and was promoted acting post captain. His rank was confirmed, but he was put on half-pay, when he came home with a convoy. He spent some time at the university of Edinburgh, and then went to Portugal to visit his cousins in Wellington’s army. In 1811 he served in
the Mediterranean, and in 1813 on the coast of America and in the expedition up the Potomac. The first years of his leisure he spent in Italy and in Paris, but speculated so much in a steamboat enterprise that by 1827 he was quite ruined. In that year he was appointed to the “Galatea” (42), and was at the Azores when
they were held by the count de Villa Flor for the queen of Portugal. He so much impressed the constitutional leaders that they begged him to take command of the fleet, which offer he accepted in February 1833. With it he destroyed the Miguelite fleet off Cape St Vincent on July 5, and on the demand of France was struck off the English navy list. Continuing his Portuguese services, he commanded the land forces on the successful
defence of Lisbon in 1834, when he was made Grand Commander of the Tower and Sword, and Count Cape St Vincent in the peerage of Portugal. On his return to England he was restored to his former rank in the navy 1836, and received command of the “Powerful” (84), in 1838. When troubles broke out in Syria he was appointed second in command, and distinguished himself by leading the storming column at Sidon on September 26, 1840, and by other services, for which he was made a K.C.B. He went on half-pay in 1841, and was in 1842 elected
M.P. for Marylebone in the Liberal interest, but lost his seat in
1846. He was promoted rear-admiral the same year, and commanded
the Channel fleet from 1846 to 1848. On the outbreak of
the Russian War he received the command of the fleet destined
to act in the Baltic, and hoisted his flag in February 1854.
He refused to attack Cronstadt, and a great outcry was raised
against him for not obeying the orders of the Admiralty and
attempting to storm the key of St Petersburg; but his inaction
has been thoroughly justified by posterity. On his return in
December 1854 he was not again offered a command. He was
elected M.P. for Southwark in February 1855, and maintained
his seat, though broken in health, until his death on the 6th of
November 1860, Sir Charles Napier was a man of undoubted
energy and courage, but of no less eccentricity and vanity.
He caused great offence to many of his brother officers by his
behaviour to his superior, Admiral Stopford, in the Syrian War,
and was embroiled all his life in quarrels with the Admiralty.
See Major-General E. Napier’s Life and Correspondence of Admiral Sir Charles Napier, K.C.B. (2 vols., London, 1862); Napier’s own War in Syria (2 vols., 1842); The Navy: its past and present state, in a series of letters, edited by Sir W. F. P. Napier (1851); and The History of the Baltic Campaign of 1854, from documents and other materials furnished by Vice-Admiral Sir C. Napier, K.C.B. (1857). See also The Life and Exploits of Commodore Napier (1841); and Life of Vice-Admiral Sir C. Napier (1854).
NAPIER, SIR CHARLES JAMES (1782–1853), British soldier and statesman, was born at Whitehall, London, in 1782, being the eldest son of Colonel George Napier (a younger son of the fifth lord Napier), and of his wife, the Lady Sarah Lennox who had charmed King George III. After the custom of those times Charles Napier had been gazetted an ensign in the 33rd regiment in 1794, and in 1797 his father secured for him the appointment of aide-de-camp to Sir James Duff, commanding the Limerick district. Longing for more active service, Napier obtained a commission as lieutenant in the 95th Manningham’s Rifles (Rifle Brigade) in 1800. This newly formed corps was designed to supply a body of light troops for the English army fit to cope with the French voltigeurs and tirailleurs, and was specially trained, at first under the eye of Colonel Coote Manningham, and then at Shorncliffe under the immediate supervision of Sir John Moore. Moore speedily perceived the military qualities of the Napiers, and inspired the three brothers—Charles of the Rifles, George of the 52nd and William of the 43rd—with an, enthusiasm which lasted all their lives; but, though happy in his general, Charles Napier quarrelled bitterly with William Stewart, the lieutenant-colonel, and in 1803 left the regiment to accompany General H. E. Fox to Ireland as aide-de-camp. The great influence of his uncle, the duke of
