Chapter C: N.oh / N : Ch Ch : N.o

.. O / . . C : N.OH.
C : N.OH, \ N : C.OH, CH : N.0,

Steiner, Divers, Scholl, Nef.

The formulae of Kekule, Divers and Armstrong have been discarded, and
it remains to be shown whether Nef's carbonyloxime formula (or the
bimolecular formula of Steiner) or Scholl's glyoxime peroxide formula
is correct. There is some doubt as to the molecular formula of
fulminic acid. The existence of double salts, and the observations of
L. Wohler and K. Theodorovits (_Ber._, 1905, 38, p. 345), that only
compounds containing two carbon atoms yielded fulminates, points to
(HCNO)2; on the other hand, Wohler (_loc. cit._ p. 1351) found that
cryoscopic and electric conductivity measurements showed sodium
fulminate to be NaCNO. Nef based his formula, which involves bivalent
carbon, on many reactions; in particular, that silver fulminate with
hydrochloric acid gave salts of formylchloridoxime, which with water
gave hydroxylamine and formic acid, thus

// NOAg // N.OH
C : NO OAg -> HC // --> HC // --> H.CO2H + H2N.OH,
\ Cl \ OH

and also on the production from sodium nitromethane and mercuric
chloride, thus CH2 : NO.Ohg --> H2O + C : NOhg(hg = 1/2Hg). H. Wieland
and F.C. Palazzo (1907) support this formula, finding that methyl
nitrolic acid, NO2.CH : N.OH, yielded under certain conditions
fulminic acid, and vice versa (Palazzo, 1907). M.Z. Jowitschitsch
(_Ann._, 1906, 347, p. 233) inclines to Scholl's formula; he found
that the synthetic silver salt of glyoxime peroxide resembled silver
fulminate in yielding hydroxylamine with hydrochloric acid, but
differed in being less explosive, and in being soluble in nitric acid.
H. Wieland and his collaborators regard "glyoxime peroxide" as an
oxide of furazane (q.v.), and have shown that a close relationship
exists between the nitrile oxides, furoxane, and fulminic acid (see
Ann. Rep., London Chem. Soc., 1909, p. 84). _Fulminuric acid_,
(HCNO)3, obtained by Liebig by boiling mercuric fulminate with water,
was synthesized in 1905 by C. Ulpiani and L. Bernardini (_Gazetta_,
iii. 35, p. 7), who regard it as NO2.CH(CN).CO.NH2. It deflagrates at
145 deg., and forms a characteristic cuprammonium salt.

The early history of mercuric fulminate and a critical account of its
application as a detonator is given in _The Rise and Progress of the
British Explosives Industry_ (International Congress of Applied
Chemistry, 1909). The manufacture and modern aspects are treated in
Oscar Guttmann, _The Manufacture of Explosives_, and _Manufacture of
Explosives, Twenty Years' Progress_ (1909).

FULTON, ROBERT (1765-1815), American engineer, was born in 1765 in Little Britain (now Fulton, Lancaster county), Pa. His parents were Irish, and so poor that they could afford him only a very scanty education. At an early age he was bound apprentice to a jeweller in Philadelphia, but subsequently adopted portrait and landscape painting as his profession. In his twenty-second year, with the object of studying with his countryman, Benjamin West, he went to England, and there became acquainted with the duke of Bridgewater, Earl Stanhope and James Watt. Partly by their influence he was led to devote his attention to engineering, especially in connexion with canal construction; he obtained an English patent in 1794 for superseding canal locks by inclined planes, and in 1796 he published a _Treatise on the Improvement of Canal Navigation_. He then took up his residence in Paris, where he projected the first panorama ever exhibited in that city, and constructed a submarine boat, the "Nautilus," which was tried in Brest harbour in 1801 before a commission appointed by Napoleon I., and by the aid of which he was enabled to blow up a small vessel with a torpedo. It was at Paris also in 1803 that he first succeeded in propelling a boat by steam-power, thus realizing a design which he had conceived ten years previously. Returning to America he continued his experiments with submarine explosives, but failed to convince either the English, French or United States governments of the adequacy of his methods. With steam navigation he had more success. In association with Robert R. Livingston (q.v.), who in 1798 had been granted the exclusive right to navigate the waters of New York state with steam-vessels, he constructed the "Clermont," which, engined by Boulton & Watt of Birmingham, began to ply on the Hudson between New York and Albany in 1807. The privilege obtained by Livingston in 1798 was granted jointly to Fulton and Livingston in 1803, and by an act passed in 1808 the monopoly was secured to them and their associates for a period depending on the number of steamers constructed, but limited to a maximum of thirty years. In 1814-1815, on behalf of the United States government, he constructed the "Fulton," a vessel of 38 tons with central paddle-wheels, which was the first steam warship. He died at New York on the 24th of February 1815. Among Fulton's inventions were machines for spinning flax, for making ropes, and for sawing and polishing marble.

See C.D. Colden, _Life of Robert Fulton_ (New York, 1817); Robert H.
Thurston, _History of the Growth of the Steam-Engine_ (New York,
1878); George H. Preble, _Chronological History of Steam Navigation_
(Philadelphia, 1883); and Mrs A.C. Sutcliffe, _Robert Fulton and the
Clermont_ (New York, 1909).

FULTON, a city and the county-seat of Callaway county, Missouri, U.S.A., 25 m. N.E. of Jefferson City. Pop. (1890) 4314; (1900) 4883 (1167 negroes); (1910) 5228. It is served by the Chicago & Alton railway. The city has an important stock market and manufactures fire-brick and pottery. At Fulton are the Westminster College (Presbyterian, founded in 1853), the Synodical College for Young Women (Pres., founded in 1871), the William Woods College for Girls (Christian Church, 1890), and the Missouri school for the deaf (1851). Here, too, is a state hospital for the insane (1847), the first institution of the kind in Missouri. The place was laid out as a town in 1825 and named Volney, but in honour of Robert Fulton the present name was adopted a little later. Fulton was incorporated in 1859.

FULTON, a city of Oswego county, New York, U.S.A., on the right bank of the Oswego river, about 10 m. S. by E. of Oswego. Pop. (1900) 5281; (1905, state census) 8847; (1910) 10,480. Fulton is served by the Delaware, Lackawanna & Western, the New York Central & Hudson River, and the New York, Ontario & Western railways, by electric railway to Oswego and Syracuse and by the Oswego Canal. The city has a Carnegie library. Ample water-power is furnished by the Oswego river, which here flows in a series of rapids, and the manufactures are many in kind. On the 3rd of July 1756, on an island (afterward called Battle Island) 4 m. N. of the present city of Fulton, a British force of about 300 under Captain John Bradstreet (1711-1774) defeated an attacking force of French and Indians (numbering about 700) under De Villiers. Soon after this, Bradstreet built a fort within the present limits of Fulton. The first civilian settler came in 1793, and the first survey (which included only a part of the subsequent village) was made in 1815. Fulton was incorporated as a village in 1835, and in April 1902 was combined with the village of Oswego Falls (pop. in 1900, 2925) and was chartered as a city.

FUM, or FUNJ HWANG, one of the four symbolical creatures which in Chinese mythology are believed to keep watch and ward over the Celestial Empire. It was begotten by fire, was born in the Hill of the Sun's Halo, and its body bears inscribed on it the five cardinal virtues. It has the breast of a goose, the hindquarters of a stag, a snake's neck, a fish's tail, a fowl's forehead, a duck's down, the marks of a dragon, the back of a tortoise, the face of a swallow, the beak of a cock, is about six cubits high, and perches only on the woo-tung tree. The appearance of Fum heralds an age of universal virtue. Its figure is that which is embroidered on the dresses of some mandarins.

FUMARIC AND MALEIC ACIDS, two isomeric unsaturated acids of composition C4H4O4. _Fumaric acid_ is found in fumitory (_Fumaria officinalis_), in various fungi (_Agaricus piperatus_, &c.), and in Iceland moss. It is obtained by heating malic acid alone to 150 deg. C., or by heating it with hydrochloric acid (V. Dessaignes, _Jahresb_., 1856, p. 463) or with a large quantity of hydrobromic acids (A. Kekule, _Ann._, 1864, 130, p. 21). It may also be obtained by boiling monobromsuccinic acid with water; by the action of dichloracetic acid and water on silver malonate (T. Komnenos, _Ann._, 1883, 218, p. 169); by the cyanide synthesis from acetylene di-iodide; and by heating maleic acid to 210 deg. C. (Z. Skraup, _Monats. f. Chemie_, 1891, 12, p. 112). It crystallizes in small prisms or needles, and is practically insoluble in cold water. It sublimes to some extent at about 200 deg. C., being partially converted into maleic anhydride and water, the reaction becoming practically quantitative if dehydrating agents be used. Reducing agents (zinc and caustic alkali, hydriodic acid, sodium amalgam, &c.) convert it into succinic acid. Bromine converts it into dibromsuccinic acid. Potassium permanganate oxidizes it to racemic acid (A. Kekule and R. Anschutz, _Ber._, 1881, 14, p. 713). By long-continued heating with caustic soda at 100 deg. C. it is converted into inactive malic acid.

_Maleic acid_ is obtained by distilling malic or fumaric acids; by heating fumaric acid with acetyl chloride to 100 deg. C; or by the hydrolysis of trichlorphenomalic acid ([beta]-trichloraceto-acrylic acid) [A. Kekule, _Ann._, 1884, 223, p. 185]. It crystallizes in monoclinic prisms, which are easily soluble in water, melt at 130 deg. C., and boil at 160 deg. C., decomposing into water and maleic anhydride. When heated with concentrated hydrobromic or hydriodic acids, it is converted into fumaric acid. It yields an anilide; oxidation converts it into mesotartaric acid. Maleic anhydride is obtained by distilling fumaric acid with phosphorus pentoxide. It forms triclinic crystals which melt at 60 deg. C. and boil at 196 deg. C.

Both acids are readily esterified by the action of alkyl halides on
their silver salts, and the maleic ester is readily transformed into
the fumaric ester by warming with iodine, the same result being
obtained by esterification of maleic acid in alcoholic solution by
means of hydrochloric acid. Both acids yield acetylene by the
electrolysis of aqueous solutions of their alkali salts, and on
reduction both yield succinic acid, whilst by the addition of
hydrobromic acid they both yield monobromsuccinic acid (R. Fittig,
_Ann._, 1877, 188, p. 98). From these results it follows that the two
acids are structurally identical, and the isomerism has consequently
to be explained on other grounds. This was accomplished by W.
Wislicenus ["Uber die raumliche Anordnung der Atome," &c., _Trans, of
the Saxon Acad. of Sciences_ (Math. Phys. Section), 1887, p. 14] by an
extension of the van't Hoff hypothesis (see STEREO-ISOMERISM). The
formulae of the acids are written thus:

HC.CO2H HC.CO2H
.. Maleic acid. .. Fumaric acid.
HC.CO2H HO2C.C.H

These account for maleic acid readily yielding an anhydride, whereas
fumaric acid does not, and for the behaviour of the acids towards
bromine, fumaric acid yielding ordinary dibromsuccinic acid, and
maleic acid the isomeric isodibromsuccinic acid.

FUMAROLE, a vent from which volcanic vapours issue, named indirectly from the Lat. _fumariolum_, a smoke-hole. The vapours from fumaroles were studied first by R.W. Bunsen, on his visit to Iceland, and afterwards by H. Sainte-Claire Deville and other chemists and geologists in France, who examined the vapours from Santorin, Etna, &c. The hottest vapours issue from dry fumaroles, at temperatures of at least 500 deg. C., and consist chiefly of anhydrous chlorides, notably sodium chloride. The acid fumaroles yield vapours of lower temperature (300 deg. to 400 deg.) containing much water vapour, with hydrogen chloride and sulphur dioxide. The alkaline fumaroles are still cooler, though above 100 deg., and evolve ammonium chloride with other vapours. Cold fumaroles, below 100 deg., discharge principally aqueous vapour, with carbon dioxide, and perhaps hydrogen sulphide. The fumaroles of Mont Pele in Martinique during the eruption of 1902 were examined by A. Lacroix, and the vapours analysed by H. Moissan, who found that they consisted chiefly of water vapour, with hydrogen chloride, sulphur, carbon dioxide, carbon monoxide, methane, hydrogen, nitrogen, oxygen and argon. These vapours issued at a temperature of about 400 deg. Armand Gautier has pointed out that these gases are practically of the same composition as those which he obtained on heating granite and certain other rocks. (See VOLCANO).

FUMIGATION (from Lat. _fumigare_, to smoke), the process of producing smoke or fumes, as by burning sulphur, frankincense, tobacco, &c., whether as a ceremony of incantation, or for perfuming a room, or for purposes of disinfection or destruction of vermin. In medicine the term has been used of the exposure of the body, or a portion of it, to fumes such as those of nitre, sal-ammoniac, mercury, &c.; fumigation, by the injection of tobacco smoke into the great bowel, was a recognized procedure in the 18th century for the resuscitation of the apparently drowned. "Fumigated" or "fumed" oak is oak which has been darkened by exposure to ammonia vapour.

FUMITORY, in botany, the popular name for the British species of _Fumaria_, a genus of small, branched, often climbing annual herbs with much-divided leaves and racemes of small flowers. The flowers are tubular with a spurred base, and in the British species are pink to purplish in colour. They are weeds of cultivation growing in fields and waste places. _F. capreolata_ climbs by means of twisting petioles. In past times fumitory was in esteem for its reputed cholagogue and other medicinal properties; and in England, boiled in water, milk or whey, it was used as a cosmetic. The root of the allied species (_Corydalis cava_ or _tuberosa_) is known as _radix aristolochia_, and has been used medicinally for various cutaneous and other disorders, in doses of 10 to 30 grains. Some eleven alkaloids have been isolated from it. The herbage of _Fumaria officinalis_ and _F. racemosa_ is used in China under the name of _Tsze-hwa-ti-ting_ as an application for glandular swellings, carbuncles and abscesses, and was formerly valued in jaundice, and in cases of accidental swallowing of the beard of grain (see F. Porter Smith, _Contrib. towards the Mat. Medica ... of China_, p. 99, 1871). The name fumitory, Latin _fumus terrae_, has been supposed to be derived from the fact that its juice irritates the eyes like smoke (see Fuchs, _De historia stirpium_, p. 338, 1542); but _The Grete Herball_, cap. clxix., 1529, fol., following the _De simplici medicina_ of Platearius, fo. xciii. (see in _Nicolai Praepositi dispensatorium ad aromatarios_, 1536), says: "It is called Fumus terre fume or smoke of the erthe bycause it is engendred of a cours fumosyte rysynge frome the erthe in grete quantyte lyke smoke: this grosse or cours fumosyte of the erthe wyndeth and wryeth out: and by workynge of the ayre and sonne it turneth into this herbe."

FUNCHAL, the capital of the Portuguese archipelago of the Madeiras; on the south coast of Madeira, in 32 deg. 37' N. and 16 deg. 54' W. Pop. (1900) 20,850. Funchal is the see of a bishop, in the archiepiscopal province of Lisbon; it is also the administrative centre of the archipelago, and the residence of the governor and foreign consuls. The city has an attractive appearance from the sea. Its whitewashed houses, in their gardens full of tropical plants, are built along the curving shore of Funchal Bay, and on the lower slopes of an amphitheatre of mountains, which form a background 4000 ft. high. Numerous country houses (_quintas_), with terraced gardens, vineyards and sugar-cane plantations occupy the surrounding heights. Three mountain streams traverse the city through deep channels, which in summer are dry, owing to the diversion of the water for irrigation. A small fort, on an isolated rock off shore, guards the entrance to the bay, and a larger and more powerfully armed fort crowns an eminence inland. The chief buildings include the cathedral, Anglican and Presbyterian churches, hospitals, opera-house, museum and casino. There are small public gardens and a meteorological observatory. In the steep and narrow streets, which are lighted by electricity, wheeled traffic is impossible; sledges drawn by oxen, and other primitive conveyances are used instead (see MADEIRA). In winter the fine climate and scenery attract numerous invalids and other visitors, for whose accommodation there are good hotels; many foreigners engaged in the coal and wine trades also reside here permanently. The majority of these belong to the British community, which was first established here in the 18th century. Funchal is the headquarters of Madeiran industry and commerce (see MADEIRA). It has no docks and no facilities for landing passengers or goods; vessels are obliged to anchor in the roadstead, which, however, is sheltered from every wind except the south. Funchal is connected by cable with Carcavellos (for Lisbon), Porthcurnow (for Falmouth, England) and St Vincent in the Cape Verde Islands (for Pernambuco, Brazil).

FUNCTION,[1] in mathematics, a variable number the value of which depends upon the values of one or more other variable numbers. The theory of functions is conveniently divided into (I.) Functions of Real Variables, wherein real, and only real, numbers are involved, and (II.) Functions of Complex Variables, wherein complex or imaginary numbers are involved.