Part 5

__ __ __ __ __ __NH2 / \_NH.NH _/ \-->NH2 / \_/ \NH2 and NH2 / \_/ \ \__/ \__/ \__/ \__/ \__/ \__/ Hydrobenzene. Benzidine. Diphenylin. __ __ __ __ __ __ R/ \_NH.NH _/ \--> / \_NH_/ \or R/ \_NH_/ \NH2 \__/ \__/ \__/ \__/ \__/ \__/ Ortho-semidine. Para-semidine.

__NH2__ or / \_/ \NH2. \__/ \__/ R

BENZOIC ACID, C7H6O2 or C6H5COOH, the simplest representative of the aromatic acids. It occurs naturally in some resins, especially in gum benzoin (from _Styrax benzoin_), in dragon's blood, and as a benzyl ester in Peru and Tolu balsams. It can be prepared by the oxidation of toluene, benzyl alcohol, benzaldehyde and cinnamic acid; by the oxidation of benzene with manganese dioxide and concentrated sulphuric acid in the cold (L. Carius, _Ann_. 1868, 148, p. 51); by hydrolysis of benzonitrile or of hippuric acid; by the action of carbon dioxide on benzene in the presence of aluminium chloride (C. Friedel and J.M. Crafts, _Ann. chim. phys._ 1888 [6], 14, p. 441); by the action of carbon dioxide on monobrombenzene in the presence of sodium; by condensing benzene and carbonyl chloride in presence of aluminium chloride, the benzoyl chloride formed being subsequently hydrolysed; and similarly from benzene and chlorformamide:--

C6H6 + Cl.CONH2 = HCl + C6H5CONH2,

the benzamide being then hydrolysed. It may also be prepared by boiling benzyl chloride with dilute nitric acid (G. Lunge, _Berichte_, 1877, 10, p. 1275); by fusing sodium benzene sulphonate with sodium formate: C6H5SO3Na + HCO2Na = C6H5COONa + NaHSO3; by heating calcium phthalate with calcium hydroxide to 330 deg.-350 deg. C.; by heating benzotrichloride with water in a sealed tube, and from the hippuric acid which is found in the urine of the herbivorae. For this purpose the urine is concentrated and the hippuric acid precipitated by the addition of hydrochloric acid; it is then filtered and boiled for some time with concentrated hydrochloric acid, when it is hydrolysed into benzoic and amido-acetic acid. It is made commercially by boiling benzotrichloride (obtained from toluene) with milk of lime, the calcium benzoate so obtained being then decomposed by hydrochloric acid

2C6H5CCl3 + 4Ca(OH)2 = (C6H5COO)2Ca + 3CaCl2 + 4H2O.

Benzoic acid crystallizes in glistening leaflets (from water) which melt at 121.4 deg. C. and boil at 249.2 deg. C. (H. Kopp). Its specific heat is 0.1946. It sublimes readily and is volatile in steam. It is readily soluble in hot water and the ordinary organic solvents, but is only slightly soluble in cold water. When heated with lime, it is decomposed, benzene being formed; if its vapours are passed over heated zinc dust, it is converted into benzaldehyde (A. Baeyer, _Ann_. 1866, 140, p. 296). Distillation of its calcium salt gives benzophenone (q.v.) with small quantities of other substances, but if the calcium salt be mixed with calcium formate and the mixture distilled, benzaldehyde is produced. By the action of sodium amalgam on an aqueous solution of the acid, benzyl alcohol, tetrahydrobenzoic acid and hexahydrobenzoic acid are formed. The salts of benzoic acid are known as the benzoates and are mostly soluble in water. They are readily decomposed by mineral acids with the production of benzoic acid, and on addition of ferric chloride to their neutral solutions give a reddish-brown precipitate of ferric benzoate.

Benzoic anhydride, (C6H5CO)2O, is prepared by the action of benzoyl chloride on sodium benzoate, or by heating benzoyl chloride with anhydrous oxalic acid (R. Anschutz, _Ann_. 1884, 226, p. 15). It crystallizes in needles, melting at 42 deg.C., and boiling at 360 deg. C. It is insoluble in water but readily soluble in alcohol and ether.

Benzoyl chloride, C6H5COCl, is formed by distilling a mixture of phosphorus pentachloride and benzoic acid; by the action of chlorine on benzaldehyde, or by passing a stream of hydrochloric acid gas over a mixture of benzoic acid and phosphorus pentoxide heated to 200 deg. C. (C. Friedel, _Ber._ 1869, 2, p. 80). It is a colourless liquid of very unpleasant smell, which boils at 198 deg. C., and solidifies in a freezing mixture, the crystals obtained melting at -1 deg. C. It shows all the characteristic properties of an acid chloride.

Ethyl benzoate, C6H5COOC2H5, is best prepared by boiling benzoic acid and alcohol with a small quantity of sulphuric acid for some hours (E. Fischer and A. Speier, _Berichte_, 1896, 28, p. 3252). It is a colourless liquid of boiling point 213 deg. C.

_Benzamide_, C6H5CONH2, is prepared by the action of benzoyl chloride on ammonia or ammonium carbonate, or from ethyl benzoate and ammonia. It crystallizes (from water) in glistening leaflets which melt at 130 deg. C. and boil at 288 deg. C. Its silver salt behaves as if it were the salt of an imido benzoic acid, since it yields benzimido ethyl ether C6H5.C( : NH).OC2H5 with ethyl iodide (J. Tafel and C. Enoch, _Berichte_, 1890, 23, p. 1550).

Chlor-, brom-, iodo- and fluor-benzoic acids are known and can be obtained by oxidizing the corresponding halogen toluenes, or from the amido acids, or by substitution. Nitration of benzoic acid gives chiefly meta-nitro-benzoic acid. The ortho- and para-nitro-benzoic acids can be obtained by oxidizing ortho-and para-nitro-cinnamic acids. Ortho-amino-benzoic acid, C6H4.NH2.COOH (anthranilic acid), is closely related to indigo (q.v.).

Gum benzoin, which contains from 12 to 20% of benzoic acid, is used in medicine as the essential constituent of benzoated lard, _Adeps benzoatus_, which owes its antiseptic properties to benzoic acid; and in friar's balsam, _Tinctura benzoini composita_, which is an ancient and valuable medicament, still largely used for inhalation in cases of laryngitis, bronchitis and other inflammatory or actually septic conditions of the respiratory tract. It owes its value to the benzoic acid which it contains. A fluid drachm of friar's balsam may be added to a pint of water at a temperature of about 140 deg. F., and the resultant vapour may be inhaled from the spout of a kettle or from a special inhaler. Benzoic acid itself, ammonium benzoate and sodium benzoate are all administered internally in doses of from five to thirty grains. The ammonium salt is most often employed, owing to the stimulant character of the ammonium base. The acid itself is a powerful antiseptic. When administered internally, it causes the appearance of hippuric acid in the urine. This is due to its combination in the body with glycocoll. The combination probably occurs in the kidney. The hippuric acid in the urine acts as a stimulant and disinfectant to the urinary mucous membrane. Benzoic acid is also excreted by the bronchi and tends to disinfect and stimulate the bronchial mucous membrane. Hence the value of friar's balsam. The acid and its salts are antipyretic and were used in Germany instead of salicylates in rheumatic fever. But the most important fact is that ammonium benzoate is largely used--often in combination with urinary anodynes such as tincture of hyoscyamus--as a urinary antiseptic in cases of cystitis (inflammation of the bladder) and pyelitis (inflammation of the pelvis of the kidney).

BENZOIN, C6H5CHOH.CO.C6H5, a ketone-alcohol, which may be prepared by boiling an alcoholic solution of benzaldehyde with potassium cyanide; by reducing benzil (C6H5CO.CO.C6H5) with zinc and acetic acid; or by the oxidation of hydrobenzoin (C6H5.CHOH.CHOH.C6H5). It is a colourless, crystalline solid, readily soluble in alcohol and ether, melting at 137 deg. C. and boiling at 343-344 deg.C. On passing the vapour of benzoin over heated lead oxide, it is converted into benzil and benzophenone. Owing to the readiness with which it is oxidized, it acts as a reducing agent, giving a red precipitate of cuprous oxide with Fehling's solution in the cold. Chlorine and nitric acid oxidize it to benzil; chromic acid mixture and potassium permanganate, to benzoic acid and benzaldehyde. On heating with zinc dust, desoxy-benzoin (C6H5CO.CH2.C6H5) is obtained; sodium amalgam converts it into hydrobenzoin; and fuming hydriodic acid at 130 deg. C. gives dibenzyl (C6H5CH2.CH2.C6H5). By fusion with alkali it is converted into benzil; and with an alcoholic solution of benzaldehyde in presence of ammonia it forms amarine (triphenyl dihydro-glyoxaline). In the presence of sulphuric acid it condenses with nitriles to oxazoles (q.v.).

BENZOIN, or GUM BENJAMIN (supposed to be from Arab. _luban_, frankincense, the first syllable being dropped in Romanic as if it were the article), a balsamic resin obtained from _Styrax benzoin_, a tree of considerable size, native to Sumatra and Java, and from other species of _Styrax_. It is obtained by making incisions in the bark of the trees, and appears to be formed as the result of the wound, not to be secreted normally. There are several varieties of benzoin in commerce: (1) Siam benzoin, which apparently does not come from _Styrax benzoin_, is the finest and most aromatic, and occurs in the form of small "tears," rarely exceeding 2 in. in length by 1/2 in. in thickness, and of "blocks" made up of these tears agglomerated by a clear reddish-brown resin. The odour of Siam benzoin is partly due to the presence of vanillin, and the substance contains as much as 38% of benzoic acid but no cinnamic acid. (2) Sumatra benzoin occurs only in masses formed of dull red resin enclosing white tears. It contains about 20% of cinnamic acid in addition to 18 or even more of benzoic. (3) Palembang benzoin, an inferior variety, said to be obtained from _Styrax benzoin_ in Sumatra, consists of greyish translucent resinous masses, containing small white opaque tears. It does not appear to contain cinnamic acid. Large quantities of benzoin are used as incense. Its medicinal uses depend on the contained benzoic acid (q.v.).

BENZOPHENONE (DIPHENYL KETONE), C6H5.CO.C6H5, the simplest representative of the true aromatic ketones. It may be prepared by distilling calcium benzoate; by condensing benzene with benzoyl chloride in the presence of anhydrous aluminium chloride; by the action of mercury diphenyl on benzoyl chloride, or by oxidizing diphenylmethane with chromic acid. It is a dimorphous substance existing in two enantiotropic forms, one melting at 26 deg. C. and the other at 48 deg. C: (Th. Zmcke, _Berichte_, 1871, 4, p. 576). It boils at 306.1 deg. C., under a pressure of 760.32 mm. It is reduced by sodium amalgam to _benzhydrol_ or _diphenyl carbinol_ C6H5.CHOH.C6H5; a stronger reducing agent, such as hydriodic acid in the presence of amorphous phosphorus converts it into _diphenylmethane_ (C6H5)2-CH2. Potash fusion converts it into benzene and benzoic acid. With phenylhydrazine it forms a hydrazone, and with hydroxylamine an oxime, which exists in one form only; if, however, one of the phenyl groups in the oxime be substituted in any way then two stereo-isomeric oximes are produced (cf. STEREO-ISOMERISM); thus parachlorbenzophenone oxime exists in two different forms (V. Meyer and K.F. Auwers, _Berichte_, 1890, 23, p. 2403). Many derivatives are known, thus ortho-amino-benzophenone, melting at 106 deg. C., can be obtained by reduction of the corresponding nitro compound; it condenses under the influence of heated lead monoxide to an acridine derivative and with acetone in presence of caustic soda it gives a quinoline. _Tetramethyl-diamido-benzophenone_ or _Michler's ketone_, CO[C6H4N.(CH3)2]3, melting at 173 deg., is of technical importance, as by condensation with various substances it can be made to yield dye-stuffs. It is prepared by the action of carbonyl chloride on dimethyl aniline in the presence of aluminium chloride: COCl2 + 2C6H5N(CH3)2 = 2HCl + CO[C6H4N(CH3)2]2.

BENZYL ALCOHOL (PHENYL CARBINOL), C6H5CH2OH, occurs as a benzoic ester in Peru balsam, as cinnamic ester in Tolu balsam, as acetic ester in essential oil of jasmine, and also in storax. It may be synthetically prepared by the reduction of benzoyl chloride; by the action of nitrous acid on benzylamine; by boiling benzyl chloride with an aqueous solution of potassium carbonate, or by the so-called "Cannizzaro" reaction, in which benzaldehyde is shaken up with caustic potash, one half of the aldehyde being oxidized to benzoic acid, and the other half reduced to the alcohol. (_Berichte_, 1881, 14, p. 2394).

2C6H5CHO + KOH = C6H5COOK + C6H5CH2OH.

It is a colourless liquid, with a faint aromatic smell, and boils at 206 deg. C. On oxidation with nitric acid it is converted into benzaldehyde, whilst chromic acid oxidizes it to benzoic acid. Reduction by means of hydriodic acid and phosphorus at 140 deg. C. gives toluene, whilst on distillation with alcoholic potash, toluene and benzoic acid are formed.

BEOTHUK, a tribe of North American Indians formerly dwelling in the interior of Newfoundland. A certain mystery attaches to them, since investigation of the few words of their language which have survived suggests that they were of distinct stock. The name (of Micmac origin) is said to mean simply "red men." They were bitterly hostile to the French settlers, and were hunted down and killed off until 1820, when a few survivors made their escape into Labrador. The last of them is believed to have died in 1829.

BEOTHY, ODON (1796-1854), Hungarian deputy and orator, was born at Grosswardein, his father being a retired officer and deputy lord-lieutenant of the county of Bihar. At the age of sixteen he served in the war against Napoleon, and was present at the great battle of Leipzig. Like so many others of his compatriots, he picked up Liberal ideas abroad. He was sent to parliament by his county in 1826 and again in 1830, but did not become generally known till the session of 1832-1836, when along with Deak he, as a liberal Catholic, defended the Protestant point of view in "the mixed marriages question." He was also an energetic advocate of freedom of speech. After parliament rose he carried his principles to their logical conclusion by marrying a Protestant lady and, being denied a blessing on the occasion by an indignant bishop, publicly declared that he could very well dispense with such blessings. In 1841 he was elected deputy lord-lieutenant of his county to counteract the influence of the lord-lieutenant, Lajos Tisza, and powerfully promoted the popular cause by his eloquence and agitation. After 1843 the conservatives succeeded in excluding him both from parliament and from his official position in the county; but during the famous "March Days" (1848) he regained all his authority, becoming at the same time a commander of militia, a deputy and lord-lieutenant. At the first session of the Upper House (5th of July 1848), he moved that it should be radically reformed, and during the war of Independence he energetically served the Hungarian government as a civil commissioner and lord justice. Towards the end of the war he reappeared as a deputy at the Szeged diet, and on the flight of the government took refuge first with Richard Cobden in London and subsequently in Jersey, where he made the acquaintance of Victor Hugo. Thence he went to Hamburg, to meet his wife, and died there on the 7th of December 1854. Beothy was a man of extraordinary ability and character, and an excellent debater. He also exercised as much influence socially over his contemporaries as politically, owing to his unfailing tact and pleasant wit.

See Antal Csengery, _Hungarian Orators and Statesmen_ (Hung., Budapest, 1851). (R. N. B.)

BEOWULF. The epic of Beowulf, the most precious relic of Old English, and, indeed, of all early Germanic literature, has come down to us in a single MS., written about A.D. 1000, which contains also the Old English poem of Judith, and is bound up with other MSS. in a volume in the Cottonian collection now at the British Museum. The subject of the poem is the exploits of Beowulf, son of Ecgtheow and nephew of Hygelac, king of the "Geatas," i.e. the people, called in Scandinavian records Gautar, from whom a part of southern Sweden has received its present name Gotland.

_The Story._--The following is a brief outline of the story, which naturally divides itself into five parts.

1. Beowulf, with fourteen companions, sails to Denmark, to offer his help to Hrothgar, king of the Danes, whose hall (called "Heorot") has for twelve years been rendered uninhabitable by the ravages of a devouring monster (apparently in gigantic human shape) called Grendel, a dweller in the waste, who used nightly to force an entrance and slaughter some of the inmates. Beowulf and his friends are feasted in the long-deserted Heorot. At night the Danes withdraw, leaving the strangers alone. When all but Beowulf are asleep, Grendel enters, the iron-barred doors having yielded in a moment to his hand. One of Beowulf's friends is killed; but Beowulf, unarmed, wrestles with the monster, and tears his arm from the shoulder. Grendel, though mortally wounded, breaks from the conqueror's grasp, and escapes from the hall. On the morrow, his bloodstained track is followed until it ends in a distant mere.

2. All fear being now removed, the Danish king and his followers pass the night in Heorot, Beowulf and his comrades being lodged elsewhere. The hall is invaded by Grendel's mother, who kills and carries off one of the Danish nobles. Beowulf proceeds to the mere, and, armed with sword and corslet, plunges into the water. In a vaulted chamber under the waves, he fights with Grendel's mother, and kills her. In the vault he finds the corpse of Grendel; he cuts off the head, and brings it back in triumph.

3. Richly rewarded by Hrothgar, Beowulf returns to his native land. He is welcomed by Hygelac. and relates to him the story of his adventures, with some details not contained in the former narrative. The king bestows on him lands and honours, and during the reigns of Hygelac and his son Heardred he is the greatest man in the kingdom. When Heardred is killed in battle with the Swedes, Beowulf becomes king in his stead.

4. After Beowulf has reigned prosperously for fifty years, his country is ravaged by a fiery dragon, which inhabits an ancient burial-mound, full of costly treasure. The royal hall itself is burned to the ground. The aged king resolves to fight, unaided, with the dragon. Accompanied by eleven chosen warriors, he journeys to the barrow. Bidding his companions retire to a distance, he takes up his position near the entrance to the mound--an arched opening whence issues a boiling stream. I The dragon hears Beowulf's shout of defiance, and rushes forth, breathing flames. The fight begins; Beowulf is all but overpowered, and the sight is so terrible that his men, all but one, seek safety in flight. The young Wiglaf, son of Weohstan, though yet untried in battle, cannot, even in obedience to his lord's prohibition, refrain from going to his help. With Wiglaf's aid, Beowulf slays the dragon, but not before he has received his own death-wound. Wiglaf enters the barrow, and returns to show the dying king the treasures that he has found there. With his last breath Beowulf names Wiglaf his successor, and ordains that his ashes shall be enshrined in a great mound, placed on a lofty cliff, so that it may be a mark for sailors far out at sea.

5. The news of Beowulf's dear-bought victory is carried to the army. Amid great lamentation, the hero's body is laid on the funeral pile and consumed. The treasures of the dragon's hoard are buried with his ashes; and when the great mound is finished, twelve of Beowulf's most famous warriors ride around it, celebrating the praises of the bravest, gentlest and most generous of kings.

_The Hero._--Those portions of the poem that are summarized above--that is to say, those which relate the career of the hero in progressive order--contain a lucid and well-constructed story, told with a vividness of imagination and a degree of narrative skill that may with little exaggeration be called Homeric. And yet it is probable that there are few readers of Beowulf who have not felt--and there are many who after repeated perusal continue to feel--that the general impression produced by it is that of a bewildering chaos. This effect is due to the multitude and the character of the episodes. In the first place, a very great part of what the poem tells about Beowulf himself is not presented in regular sequence, but by way of retrospective mention or narration. The extent of the material thus introduced out of course may be seen from the following abstract.

When seven years old the orphaned Beowulf was adopted by his grandfather king Hrethel, the father of Hygelac, and was regarded by him with as much affection as any of his own sons. In youth, although famed for his wonderful strength of grip, he was generally despised as sluggish and unwarlike. Yet even before his encounter with Grendel, he had won renown by his swimming contest with another youth named Breca, when after battling for seven days and nights with the waves, and slaying many sea-monsters, he came to land in the country of the Finns. In the disastrous invasion of the land of the Hetware, in which Hygelac was killed, Beowulf killed many of the enemy, amongst them a chieftain of the Hugas, named Daeghrefn, apparently the slayer of Hygelac. In the retreat he once more displayed his powers as a swimmer, carrying to his ship the armour of thirty slain enemies. When he reached his native land, the widowed queen offered him the kingdom, her son Heardred being too young to rule. Beowulf, out of loyalty, refused to be made king, and acted as the guardian of Heardred during his minority, and as his counsellor after he came to man's estate. By giving shelter to the fugitive Eadgils, a rebel against his uncle the king of the "Sweon" (the Swedes, dwelling to the north of the Gautar), Heardred brought on himself an invasion, in which he lost his life. When Beowulf became king, he supported the cause of Eadgils by force of arms; the king of the Swedes was killed, and his nephew placed on the throne.

_Historical Value._--Now, with one brilliant exception--the story of the swimming-match, which is felicitously introduced and finely told--these retrospective passages are brought in more or less awkwardly, interrupt inconveniently the course of the narrative, and are too condensed and allusive in style to make any strong poetic impression. Still, they do serve to complete the portraiture of the hero's character. There are, however, many other episodes that have nothing to do with Beowulf himself, but seem to have been inserted with a deliberate intention of making the poem into a sort of cyclopaedia of Germanic tradition. They include many particulars of what purports to be the history of the royal houses, not only of the Gautar and the Danes, but also of the Swedes, the continental Angles, the Ostrogoths, the Frisians and the Heathobeards, besides references to matters of unlocalized heroic story such as the exploits of Sigismund. The Saxons are not named, and the Franks appear only as a dreaded hostile power. Of Britain there is no mention; and though there are some distinctly Christian passages, they are so incongruous in tone with the rest of the poem that they must be regarded as interpolations. In general the extraneous episodes have no great appropriateness to their context, and have the appearance of being abridged versions of stories that had been related at length in poetry. Their confusing effect, for modern readers, is increased by a curiously irrelevant prologue. It begins by celebrating the ancient glories of the Danes, tells in allusive style the story of Scyld, the founder of the "Scylding" dynasty of Denmark, and praises the virtues of his son Beowulf. If this Danish Beowulf had been the hero of the poem, the opening would have been appropriate; but it seems strangely out of place as an introduction to the story of his namesake.