1854. An unsuccessful campaign for the governorship of Missouri in 1856

ended his political career. He died at Washington on the 10th of April 1858. Benton's entire career was eminently creditable, and he is, besides, one of the most picturesque figures in American political history. His political principles--whether as regarded lobbying, congressional jobbing, civil service or great issues of legislation and foreign affairs--were of the highest. He was so independent that he had great dislike for caucuses, and despised party platforms--although he never voted any but the Democratic ticket, even when his son-in-law, J.C. Fremont, was the Republican presidential candidate in 1856; nor would he accept instructions from the Missouri legislature. His career shows no truckling to self-interest, and on large issues he outgrew partisanship. Although palpably inferior to each of his great senatorial colleagues, Webster, Clay and Calhoun, in some gifts, yet if character, qualities and career be taken in the whole his were possibly the most creditable of all. Benton was austere, aggressive and vain; besides, he had a fatal deficiency of humour. Nevertheless he had great influence, which was a deserved tribute to his ability and high character. An indefatigable student, he treated all subjects capably, and especially in questions of his country's history and the exploration of the West had few equals--in the latter none. He acted always with uncalculating boldness, and defended his acts with extraordinary courage and persistence. Benton wrote a _Thirty Years' View ... of the American Government_ (2 vols., 1854-1856), characteristic of the author's personality; it is of great value for the history of his time. He also compiled an _Abridgment of the Debates of Congress_, 1789-1850 (16 vols., 1857-1861), likewise of great usefulness; and published a bitter review of the Dred Scott decision full of extremely valuable historical details--_Historical and Legal Examination of ... the Dred Scott Case_ (1857). All were written in the last eight years of his life and mostly in the last three. The best biography is that by W.M. Meigs, _Life of Thomas Hart Benton_ (Philadelphia and London, 1904). See also Theodore Roosevelt's _Thomas Hart Benton_ (Boston, 1887), in the "American Statesmen" series, which admirably brings out Benton's significance as a western man; and Joseph M. Rogers's _Thomas Hart Benton_ (Philadelphia, 1905) in the "American Crisis" series. BENTON HARBOR, a city of Berrien county, Michigan, U.S.A., on the Saint Joseph river, about 1 m. from Lake Michigan (with which it is connected by a ship canal), near the S.W. corner of the state, and 1 m. N.E. of St Joseph. Pop. (1890) 3692; (1900) 6562, of whom 795 were foreign-born; (1904) 6702; (1910) 9185. It is served by the Pere Marquette, the Michigan Central, and the Cleveland, Cincinnati, Chicago & St Louis railways, by electric railways to St Joseph and Niles, Mich., and South Bend, Indiana, and for a part of the year by steamboat lines to Chicago and Milwaukee. One mile south-east of the city are a sanitarium and the Eastman mineral springs; within the city also there are springs and bath-houses. Near the city is a communistic religious community, the Israelite House of David, founded in 1903, the members believe that they are a part of the 144,000 elect (Revelation, vii, xiv) ultimately to be redeemed. Benton Harbor has a large trade in fruit (peaches, grapes, pears, cherries, strawberries, raspberries and apples) and other market garden produce raised in the vicinity. The city's manufactures include fruit baskets, preserved fruits, cider, vinegar, pickles, furniture, lumber and stationers' supplies, particularly material for the "loose-leaf ledger" system of accounting. Benton Harbor, which was known as Bronson Harbor until 1865, was incorporated as a village in 1869, was chartered as a city in 1891, and in 1903 received a new charter. BENUE, a river of West Africa, the largest and most important affluent of the Niger (q.v.), which it joins after a course of over 800 m. in a general east to west direction from its source in the mountains of Adamawa. Through the Tuburi marshes there is a water connexion between the Benue (Niger) and Shari (Lake Chad) systems. BEN VENUE, a mountain in south-west Perthshire, Scotland, 10 m. W. of Callander. Its principal peaks are 2393 and 2386 ft. high, and, owing to its position near the south-eastern shore of Loch Katrine, its imposing contour is one of the most familiar features in the scenery of the Trossachs, the mountain itself figuring prominently in _The Lady of the Lake_. On its northern base, close to the lake, Sir Walter Scott placed the Coir-nan-Uriskin, or "Goblin's Cave." Immediately to the south of the cave is the dell called Beal(ach)-nam-Bo, or "Cattle Pass," through which were driven to the refuge of the Trossachs the herds lifted by the Highland marauders in their excursions to the lands south of Loch Lomond. The pass, though comparatively unvisited, offers the grandest scenery in the district. BENZALDEHYDE (oil of bitter almonds), C6H5CHO, the simplest representative of the aromatic aldehydes. It was first isolated in 1803 and was the subject of an important investigation by J. v. Liebigin 1837 (_Annalen_, 1837, 22, p. 1). It occurs naturally in the form of the glucoside amygdalin (C20H27NO11), which is present in bitter almonds, cherries, peaches and the leaves of the cherry laurel; and is obtained from this substance by hydrolysis with dilute acids: C20H27NO11 + 2H2O = HCN + 2C6H12O6 + C6H5CHO. It occurs free in bitter almonds, being formed by an enzyme decomposition of amygdalin (q.v.). It may also be prepared by oxidizing benzyl alcohol with concentrated nitric acid; by distilling a mixture of calcium benzoate and calcium formate; by the condensation of chlor-oxalic ester with benzene in the presence of aluminium chloride, the ester of the ketonic acid formed being then hydrolysed and the resulting acid distilled: C6H6 + Cl.CO.COOC2H5 = C6H5CO.COOC2H5 + HCl, C6H5CO.COOH = C6H5CHO + CO2; by the action of anhydrous hydrocyanic acid and hydrochloric acid on benzene, an aldime being formed as an intermediate product: C6H6 + HCN + HCl = C6H5CH : NH.HCl, Benzaldine hydrochloride C6H5CH : NH.HCl + H2O = NH4Cl + C6H5CHO; and by the action of chromium oxychloride on toluene dissolved in carbon bisulphide (A. Etard, _Berichte_, 1884, 17, pp. 1462, 1700). Technically it is prepared from toluene, by converting it into benzyl chloride, which is then heated with lead nitrate: C6H5CH2Cl + Pb(NO3)2 = 2NO2 + PbCl.OH + C6H5CHO, or, by conversion into benzal chloride, which is heated with milk of lime under pressure. C6H5CHCl2 + CaO = CaCL2 + C6H5CHO. E. Jacobsen has also obtained benzaldehyde by heating benzal chloride with glacial acetic acid: C6H5CHCl2 + CH3COOH = CH3COCl + HCl + C6H5CHO. Benzaldehyde is a colourless liquid smelling of bitter almonds. Its specific gravity is 1.0636 (0/0 deg. C.), and it boils at 179.1 deg. C. (751.3 mm). It is only slightly soluble in water, but is readily volatile in steam. It possesses all the characteristic properties of an aldehyde; being readily oxidized to benzoic acid; reducing solutions of silver salts; forming addition products with hydrogen, hydrocyanic acid and sodium bisulphite; and giving an oxime and a hydrazone. On the other hand, it differs from the aliphatic aldehydes in many respects; it does not form an addition product with ammonia but condenses to hydrobenzamide (C6H5CH)3N2; on shaking with alcoholic potash it undergoes simultaneous oxidation and reduction, giving benzoic acid and benzyl alcohol (S. Cannizzaro); and on warming with alcoholic potassium cyanide it condenses to benzoin (q.v.). The oxidation of benzaldehyde to benzoic acid when exposed to air is not one of ordinary oxidation, for it has been observed in the case of many compounds that during such oxidation, as much oxygen is rendered "active" as is used up by the substance undergoing oxidation; thus if benzaldehyde is left for some time in contact with air, water and indigosulphonic acid, just as much oxygen is used up in oxidizing the indigo compound as in oxidizing the aldehyde. A. v. Baeyer and V. Villiger (_Berichte_, 1900, 33, pp. 858, 2480) have shown that benzoyl hydrogen peroxide C6H5.CO.O.OH is formed as an intermediate product and that this oxidizes the indigo compound, being itself reduced to benzoic acid; they have also shown that this peroxide is soluble in benzaldehyde with production of benzoic acid, and it must be assumed that the oxidation of benzaldehyde proceeds as shown in the equations: C6H5CHO + O2 = C6H5.CO.O.OH, C6H5CO.O.OH + C6H5CHO = 2C6H5COOH. Further see G. Bodlander, _Ahrens Sammlung_, 1899, iii. 470; W.P. Jorissen, _Zeit. fur phys. Chem._, 1897, 22, p. 56; C. Engler and W. Wild, _Berichte_, 1897, 30, p. 1669. The oxime of benzaldehyde (C6H5CH:N.OH), formed by the addition of hydroxylamine to the aldehyde, exhibits a characteristic behaviour when hydrochloric acid gas is passed into its ethereal solution, a second modification being produced. The former (known as the [alpha] or benz-anti-aldoxime) melts at 34-35 deg. C.; the latter ([beta] or benz-syn-aldoxime) melts at 130 deg. C. and is slowly transformed into the [alpha] form. The difference between the two forms has been explained by A. Hantzsch and A. Werner (_Berichte_, 1890, 23, p. 11) by the assumption of the different spatial arrangement of the atoms (see STEREO-ISOMERISM). On account of the readiness with which it condenses with various compounds, benzaldehyde is an important synthetic reagent. With aniline it forms benzylidine aniline C6H5CH:N.C6H5, and with acetone, benzal acetone C6H5CH : CH.CO.CH3. Heated with anhydrous sodium acetate and acetic anhydride it gives cinnamic acid (q.v.); with ethyl bromide and sodium it forms triphenyl-carbinol (C6H5)3C.OH; with dimethylaniline and anhydrous zinc chloride it forms leuco-malachite green C6H5CH[C6H4N(CH3)2]2; and with dimethylaniline and concentrated hydrochloric acid it gives dimethylaminobenzhydrol, C6H5CH(OH)C6H4N(CH3)2. Heated with sulphur it forms benzoic acid and stilbene: 2C7H6O + S = C6H5COOH + C6H6CHS, 2C6H5CHS = 2S + C14H12. Its addition compound with hydrocyanic acid gives mandelic acid C6H5CH(OH).COOH on hydrolysis; when heated with sodium succinate and acetic anhydride, phenyl-iso-crotonic acid C6H5CH : CH.CH2COOH is produced, which on boiling is converted into [alpha]-naphthol C10H7OH. It can also be used for the synthesis of pyridine derivatives, since A. Hantzsch has shown that aldehydes condense with aceto-acetic ester and ammonia to produce the homologues of pyridine, thus: R R | | ROOC.CH2 CHO CH2.COOR ROOC.C-CH-C.COOR | + + | = || || + 3H2O. H3C.CO NH3 CO.CH3 H3C.C-NH-C.CH3 On nitration it yields chiefly meta-nitro-benzaldehyde, crystallizing in needles which melt at 58 deg. C. The ortho-compound may be obtained by oxidizing ortho-nitrocinnamic acid with alkaline potassium permanganate in the presence of benzene; or from ortho-nitrobenzyl chloride by condensing it with aniline, oxidizing the product so obtained to ortho-nitrobenzylidine aniline, and then hydrolysing this compound with an acid (_Farben fabrik d. Meister, Lucius und Bruning_). It crystallizes in yellowish needles, which are volatile in steam and melt at 46 deg. C. It is used in the artificial production of indigo (see _German Patent_ 19768). Para-nitrobenzaldehyde crystallizes in prisms melting at 107 deg. C. and is prepared by the action of chromium oxychloride on para-nitrotoluene, or by oxidizing para-nitrocinnamic acid. By the reduction of ortho-nitrobenzaldehyde with ferrous sulphate and ammonia, ortho-aminobenzaldehyde is obtained. This compound condenses in alkaline solution with compounds containing the grouping -CH2-CO- to form quinoline (q.v.) or its derivatives; thus, with acetaldehyde it forms quinoline, and with acetone, [alpha]-methyl quinoline. With urea it gives quinazolone CH /\ / \\N | | | | | CO , \/ \ / NH and with mandelic nitrile and its homologues it forms oxazole derivatives (S.S. Minovici, _Berichte_, 1896, 29, p. 2097). BENZENE, C6H6, a hydrocarbon discovered in 1825 by Faraday in the liquid produced in the compression of the illuminating gas obtained by distilling certain oils and fats. E. Mitscherlich prepared it in 1834 by distilling benzoic acid with lime; and in 1845 Hofmann discovered it in coal-tar. It was named "benzin" or "benzine" by Mitscherlich in 1833, but in the following year Liebig proposed "benzol" (the termination _ol_ being suggested by the Lat. _oleum_, oil); the form "benzene" was due to A.W. Hofmann. The word "benzine" is sometimes used in commerce for the coal-tar product, but also for the light petroleum better known as petroleum-benzine; a similar ambiguity is presented by the word "benzoline," which is applied to the same substances as the word "benzine." "Benzene" is the term used by English chemists, "benzol" is used in Germany, and "benzole" in France. Benzene is manufactured from the low-boiling fractions of the coal-tar distillate (see COAL-TAR). The first successful fractionation of coal-tar naphtha was devised by C.B. Mansfield (1819-1855), who separated a benzol distilling below 100 deg. from a less volatile naphtha by using a simple dephlegmator. At first, the oil was manufactured principally for combustion in the Read-Holliday lamp and for dissolving rubber, but the development of the coal-tar colour industry occasioned a demand for benzols of definite purity. In the earlier stages 30%, 50% and 90% benzols were required, the 30% being mainly used for the manufacture of "aniline for red," and the 90% for "aniline for blue." (The term "30% benzol" means that 30% by volume distils below 100 deg.) A purer benzol was subsequently required for the manufacture of aniline black and other dye-stuffs. The process originally suggested by Mansfield is generally followed, the success of the operation being principally conditioned by the efficiency of the dephlegmator, in which various improvements have been made. The light oil fraction of the coal-tar distillate, which comes over below 140 deg. and consists principally of benzene, toluene and the xylenes, yields on fractionation (1) various volatile impurities such as carbon disulphide, (2) the benzene fraction boiling at about 80 deg. C., (3) the toluene fraction boiling at 100 deg., (4) the xylene fraction boiling at 140 deg. The fractions are agitated with strong sulphuric acid, and then washed with a caustic soda solution. The washed products are then refractionated. The toluene fraction requires a more thorough washing with sulphuric acid in order to eliminate the thiotolene, which is sulphonated much less readily than thiophene. Benzene is a colourless, limpid, highly refracting liquid, having a pleasing and characteristic odour. It may be solidified to rhombic crystals which melt at 5.4 deg. C. (Mansfield obtained perfectly pure benzene by freezing a carefully fractionated sample.) It boils at 80.4 deg., and the vapour is highly inflammable, the flame being extremely smoky. Its specific gravity is 0.899 at 0 deg. C. It is very slightly soluble in water, more soluble in alcohol, and completely miscible with ether, acetic acid and carbon disulphide. It is an excellent solvent for gums, resins, fats, &c.; sulphur, phosphorus and iodine also dissolve in it. It sometimes separates with crystals of a solute as "benzene of crystallization," as for example with triphenylmethane, thio-p-tolyl urea, tropine, &c. Benzene is of exceptional importance commercially on account of the many compounds derivable from it, which are exceedingly valuable in the arts. Chemically it is one of the most interesting substances known, since it is the parent of the enormous number of compounds styled the "aromatic" or "benzenoid" compounds. The constitution of the benzene ring, the isomerism of its derivatives, and their syntheses from aliphatic or open-chain compounds, are treated in the article CHEMISTRY. A summary of its chemical transformations may be given here, and reference should be made to the articles on the separate compounds for further details. Passed through a red-hot tube, benzene vapour yields hydrogen, diphenyl, diphenylbenzenes and acetylene; the formation of the last compound is an instance of a reversible reaction, since Berthelot found that acetylene passed through a red-hot tube gave some benzene. Benzene is very stable to oxidants, in fact resistance to oxidation is a strong characteristic of the benzene ring. Manganese dioxide and sulphuric acid oxidize it to benzoic and o-phthalic acid; potassium chlorate and sulphuric acid breaks the ring; and ozone oxidizes it to the highly explosive white solid named ozo-benzene, C6H6O6. Hydriodic acid reduces it to hexamethylene (cyclo-hexane or hexa-hydro-benzene); chlorine and bromine form substitution and addition products, but the action is slow unless some carrier such as iodine, molybdenum chloride or ferric chloride for chlorine, and aluminium bromide for bromine, be present. It is readily nitrated to nitrobenzene, two, and even three nitro groups being introduced if some dehydrator such as concentrated sulphuric acid be present. Sulphuric acid gives a benzene sulphonic acid. BENZIDINE (DIPARA-DIAMINO-DIPHENYL), NH2.C6H4.C6H4.NH2, a chemical base which may be prepared by the reduction of the corresponding dinitro-diphenyl, or by the reduction of azo-benzene with tin and hydrochloric acid. In this latter case hydrazo-benzene C6H5NH.NH.C6H5 is first formed and then undergoes a peculiar re-arrangement into benzidine (see H. Schmidt and G. Schultz, _Annalen_, 1881, 207, p. 320; O.N. Witt and Hans v. Helmont, _Berichte_, 1894, 27, p. 2352; P. Jacobson, _Berichte_, 1892, 25, p. 994). Benzidine crystallizes in plates (from water) which melt at 122 deg. C., and boil above 360 deg. C., and is characterized by the great insolubility of its sulphate. It is a di-acid base and forms salts with the mineral acids. It is readily brominated and nitrated; when the nitration is carried out in the presence of sulphuric acid, the nitro-groups take up the meta position with regard to the amino-groups. Benzidine finds commercial application since its tetrazo compound couples readily with amino-sulphonic acids, phenol carboxylic acids, and phenol and naphthol-sulphonic acids to produce substantive cotton dyes (see DYEING). Among such dyestuffs are chrysamine or flavophenine, obtained from salicylic acid and diazotized benzidine, and congo red obtained from sodium naphthionate and diazotized benzidine. On the constitution of benzidine see G. Schultz (_Annalen_, 1874, 174, p. 227). _The Benzidine and Semidine Change._--Aromatic hydrazo compounds which contain free para positions are readily converted by the action of acids, acid chlorides and anhydrides into diphenyl derivatives; thus, as mentioned above, hydrazo-benzene is converted into benzidine, a small quantity of diphenylin being formed at the same time. The two products are separated by the different solubilities of their sulphates. This reaction is known as the _benzidine transformation_. If, however, one of the para positions in the hydrazo compound is substituted, then either diphenyl derivatives or azo compounds are formed, or what is known as the _semidine change_ takes place (P. Jacobson, _Berichte_, 1892, 25, p. 992; 1893, 26, p. 681; 1896, 29, p. 2680; _Annalen_, 1895, 287, p. 97; 1898, 303, p. 290). A para mono substituted hydrazo compound in the presence of a hydrochloric acid solution of stannous chloride gives either a para diphenyl derivative (the substituent group being eliminated), an ortho-semidine, a para-semidine, or a diphenyl base, whilst a decomposition with the formation of amines may also take place. The nature of the substituent exerts a specific influence on the reaction; thus with chlorine or bromine, ortho-semidines and the diphenyl bases are the chief products; the dimethylamino, -N(CH3)2, and acetamino, -NHCOCH3, groups give the diphenyl base and the para-semidine respectively. With a methyl group, the chief product is an ortho-semidine, whilst with a carboxyl group, the diphenyl derivative is the chief product. The ortho- and para- semidines can be readily distinguished by their behaviour with different reagents; thus with nitrous acid the ortho-semidines give azimido compounds, whilst the para-semidines give complex diazo derivatives; with formic or acetic acids the ortho-semidines give anhydro compounds of a basic character, the para-semidines give acyl products possessing no basic character. The carbon disulphide and salicylic aldehyde products have also been used as means of distinction, as has also the formation of the stilbazonium bases obtained by condensing ortho-semidines with benzil (O.N. Witt, _Berichte_, 1892, 25, p. 1017). Structurally we have:-- __ __ __ __ __ __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.