FOOTNOTE:

[1] A name misapplied in the southern hemisphere to _Diomedea

melanophrys_, one of the albatrosses.

FULMINIC ACID, HCNO or H2C2N2O2, an organic acid isomeric with cyanic

and cyanuric acids; its salts, termed fulminates, are very explosive and

are much employed as detonators. The free acid, which is obtained by

treating the salts with acids, is an oily liquid smelling like prussic

acid; it is very explosive, and the vapour is poisonous to about the

same degree as that of prussic acid. The first fulminate prepared was

the "fulminating silver" of L.G. Brugnatelli, who found in 1798 that if

silver be dissolved in nitric acid and the solution added to spirits of

wine, a white, highly explosive powder was obtained. This substance is

to be distinguished from the black "fulminating silver" obtained by

C.L. Berthollet in 1788 by acting with ammonia on precipitated silver

oxide. The next salt to be obtained was the mercuric salt, which was

prepared in 1799 by Edward Charles Howard, who substituted mercury for

silver in Brugnatelli's process. A similar method is that of J. von

Liebig (1823), who heated a mixture of alcohol, nitric acid and mercuric

nitrate; the salt is largely manufactured by processes closely

resembling the last. A laboratory method is to mix solutions of sodium

nitromethane, CH2:NO(ONa), and mercuric chloride, a yellow basic salt

being formed at the same time. Mercuric fulminate is less explosive than

the silver salt, and forms white needles (with 1/2H2O) which are

tolerably soluble in water. The use of mercuric fulminate as a detonator

dates from about 1814, when the explosive cap was invented. It is still

the commonest detonator, but it is now usually mixed with other

substances; the British service uses for percussion caps 6 parts of

fulminate, 6 of potassium chlorate and 4 of antimony sulphide, and for

time fuses 4 parts of fulminate, 6 of potassium chlorate and 4 of

antimony sulphide, the mixture being damped with a shellac varnish; for

use in blasting, a home office order of 1897 prescribes a mixture of 4

parts of fulminate and 1 of potassium chlorate. In 1900 Bielefeldt found

that a fulminate placed on top of an aromatic nitro compound, such as

trinitrotoluene, formed a useful detonator; this discovery has been

especially taken advantage of in Germany, in which country detonators of

this nature are being largely employed. Tetranitromethylaniline (tetryl)

has also been employed (Brit. Pat. 13340 of 1905). It has been proposed

to replace fulminate by silver azoimide (Wohler & Matter, Brit. Pat.

4468 of 1908), and by lead azoimide (Hyronimus, Brit. Pat. 1819 of

1908).

The constitution of fulminic acid has been investigated by many

experimenters, but apparently without definitive results. The

researches of Liebig (1823), Liebig and Gay-Lussac (1824), and of

Liebig again in 1838 showed the acid to be isomeric with cyanic acid,

and probably (HCNO)2, since it gave mixed and acid salts. Kekule, in

1858, concluded that it was nitroacetonitrile, NO2.CH2.CN, a view

opposed by Steiner (1883), E. Divers and M. Kawakita (1884), R. Scholl

(1890), and by J.U. Nef (1894), who proposed the formulae:

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.

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