None
These ureides are usually well crystallised, and are aminic and also markedly acid in character. On hydrolysis, they give first the corresponding uro-acid and then urea and free acid. They are sometimes formed on oxida- tion of di ureides (see below) ; thus parabanic acid is obtained by oxidising uric acid with nitric acid. The alcohol-acids and the aldehydo-acids also give such condensations (see above), yielding, for example, hydantoin, kydantoic acid, and allanturic acid (from glyoxylic acid). When 2 mols. of urea take part in the condensation, diureides are obtained, these forming the group containing uric acid, a) HN -- CO (6) I 0) (2) CO (5) C— NH\ 1 II >CO (8) (3) NH -- C— NHX (4) (9) and its derivatives : xanthine, caffeine, theobromine, guanine, hypoxanthin e, alloxanthine, purpuric acid, allantoin, etc. The positions of the substituent groups are indicated by the bracketed numbers shown in the above formula for uric acid. During recent years successful attempts have been made, by means of -ethyl cyanoacetate, to synthesise all these xanthine bases and to convert them, one into the other (see Berichte der deutsch. chem. Gesells., 1899, 32, p. 435). As a general rule, the ureides and diureides have a more or less marked acid character and, as they contain no carboxyl group, this acidity is explained 436 ORGANIC CHEMISTRY as due to the existence of these compounds in tautomeric forms, just as is the case with succinimide, CH2— >NH. In the latter it is assumed that CH2— CO' the iminic hydrogen atom is very mobile and undergoes displacement and union with the oxygen of the neighbouring carbonyl group, a double linking between carbon and nitrogen being formed and an acid hydroxyl group capable of forming salts with metals. The tautomeric formula of Succinimide CH2 • C(OHk xN : C • OH would hence be CH, CO N, and that of Parabanic Acid, N : C • OH similar formulae hold for uric acid and barbituric acid, the latter functioning as a dibasic acid (in this case, however, the acid character is perhaps to be attributed to the hydrogen of the methylene group, CH2). Several diureides are found in nature, e.g., in guano, in the urine and muscles of carnivora, in the excreta of serpents, in articular concretions, and in certain plants (theobromine in cocoa, caffeine, etc.), The constitutional formulae of the more important diureides are as follow : CO ,N(CH8)— CO \ I XN(CH3)— CO C0( ,NH-C(CH3)X CH O -CO' Dimethylparabanic acid (Cholestrophane) Metbyluracil < /|CO-NH I CO-NH <CO-HN> Alloxanthine — NH -> NH— CH CO CO CH. CH, Murexide N-C-N • II II >CH CH C — NH/ I i N=CH Purino N — CO I i CO CH • NH • CO • NH2 •N — CO Dimethylpseudouric acid 2 CO— NH' Allantoin N — C — N \ CC1 CC1 C — NH Trichloropurine CO C— NH^ CH3-N — CO Theophylline JCH ^±13 • S ( — v II /CH )O C— N(CH3)/ i II CH V_y II C- >H -NH/ CO 1 c- > -NH/ CH8-1 I — CO I yH -CO NH — CO Caffeine Hypox: mthine Xanthine CH N — C — N I! II CH C — NH ! I N = C • NH2 Adenine \CH NH— C — N I II NH:C C — NH' ! I NH — CO Guanine \ CH COCOA AND CHOCOLATE 437 URIC ACID, C5H4O3N4. Syntheses of uric acid are many and various ; from cyano- acetic acid, or.glycocoll or isodialuric acid, by heating with urea; from aminobarbituric acid and potassium cyanate ; from ethyl acetoacetate and urea, passing through methyl - uracil, nitrouracil, hydroxyuracil, and isodialuric acid. The following scheme represents the various steps of the synthesis frpm malonic acid : 1 NH9 CO -OH NH — CO NH — CO I i I 1 li CO CH2 > CO CH2 > CO C:N-OH > I I II' II NIT CO -OH NH — CO NH — CO Urea Malonic acid Barbituric acid Violurie acid NH — OC NH — CO NH — CO I ! II II CO CH-NH2 — > CO CH — NHX — > CO C — NIL II I I >co i || >co NH — CO NH — CO NH/ NH — C — NH/ Uramil Pseudouric acid Uric acid Uric acid is a feeble dibasic acid (see above), and forms a white, amorphous substance insoluble in alcohol or ether and almost insoluble in water. It dissolves, however, in concentrated sulphuric acid, from which it separates unchanged on dilution with water. It is extracted from guano, the excrements of serpents, and the urine of carnivora. Evaporation of uric acid with dilute nitric acid and treatment of the residue with ammonia yields murexide, which forms yellowish green crystals which" give a purple aqueous solution, turning blue on addition of alkali (characteristic reaction for uric acid ). THEOBROMINE (3 : 7-Dimethyl-2 : 6-dioxypurine), C?H8O2N4 or CH3 • N — C— — N. II >CH CO C — N(CH3)/ NH— CO is extracted by means of boiling alcohol from cocoa,2 de-fatted and made into a paste with 1 The constitution of uric acid was demonstrated first by Medicus, and later, by various syntheses, by E. Fischer (Liebig's Annalen, 1882, 215, p. 253). The presence of a chain, — C — C — C — , and of a carbonic acid residue is shown by the formation of urea and alloxan when uric acid is treated in the cold with nitric acid. The presence of four imino-groups is deduced from the fact that, by introduction of four methyl groups and subsequent hydrolysis, the four atoms of nitrogen are eliminated as methylamine. A large part of the uric acid molecule is rendered evident jby the formation of allantoin (of known constitution) on oxidation with alkaline perman- ganate, and by the formation of methylurea and methylalloxan on oxidation of dimethyluric acid. 2 Cocoa and Chocolate. Cocoa is placed on the market in the form of large violet seeds of Theobroma cacao, which grows well in the Antilles, Mfexico, Guatemala, Java, Borneo, Esmeralda (equator), etc. The red or brown mature fruits resemble cucumbers, each containing fifty to sixty seeds like beans. The seeds are separated from the pulp, heaped in casks for four to five days to initiate the fermentation which increases the aroma, and then dried in the sun. The chemical composition of the decorticated seeds differs considerably with the variety : fatty substance (cocoa-butter), 40 to 55 per cent.; proteins, 10 to 18 per cent.; cellulose, 3 to 6 per cent. ; sugars and starch, 8 to 15 per cent. ; theobromine, 0-8 to 2-5 per cent. ; ash, 3 to 4 per cent. Cocoa-butter (or cacao-butter) is extracted by pressing the seeds hot, and forms a faintly yellow mass of pleasing odour; it melts at 29° to 31°, and contains the glycerides of arachic, palmitic, oleic, stearic, and lauric acids. In the manufacture of chocolate, the seeds are washed in suitable sieves- and then gently and cautiously heated for thirty to forty minutes to facilitate skinning. They are next crushed in mortars or rotating cylinders, the flour obtained being made into a paste with sugar and worked for a long time on heated stone rollers, different ingredients and flavouring matters being added to give the different kinds of chocolate ; the homogeneous paste then passes to the moulds. 438 ORGANIC CHEMISTRY lime. Synthetically it is obtained by treating the lead salt of xanthine with methyl iodide, or from methyluric acid and phosphorus oxychloride. It forms white, anhydrous crystals which have a bitter taste and dissolve only slightly in water, alcohol or ether. It is soluble in acids or alkalies, and at 290° volatilises without melting. It behaves as a weak acid and as a weak base. With methyl iodide the silver salt yields caffeine. With concentrated nitric acid, chlorine and ammonia, it gives the same reactions as caffeine (see below). In the form of different salts, theo bromine is used as a stimulant and diuretic. Before the war it cost about 72s. per kilo. CAFFEINE or THEINE, C5H(CH3)3O2N4 + H2O, is trimethylxanthine or methyl- theobromine (for constitution, see p. 436). It is an alkaloid formed in varying proportions (0-5 to 2 per cent. ) in coffee seeds.1 The leaves of the coffee plant C9ntain up to 1-3 per cent., Good chocolate contains from 40 to 60 per cent, of cocoa, the rest being sugar ; ordinary qualities contain 10 to 15 per cent, of starch. The amounts of cocoa imported by various countries are as follows (tons ) : United States Germany Great Britain France Holland (one half re-3xported) Belgium (one half re-exported) Spain Switzer- land Italy 5J190T. 39,239 34,515 25,900 23,180 22,870 / 5,963 5,652 7,124 1,456 1910. 52,546 43,941 32,046 25,076 34,229 9,881 5,517 9,089 1,886 1912. 69,447 55,085 34,145 ; 26,890 41,858 13,023 5,241 10,342 2,432 1913. 70,660 52,878 35,543 27,610 46,810 11,620 6,166 10,248 2,457 1914. 80,479 — 42,416 26,085 52,375 • 6,911 10,078 2,275 1916. 110,050 —  of the Gold Coast increased from 5770 tons in 1904 to 40,640 tons in 1911; in the German colonies, especially the Cameroons, the crop rose from 1454 tons in 1905 to 5500 tons in 1912. Italy imported and exported the following quantities of chocolate : Importation Exportation fTons 1908 . 1,090 £ . — 230 1910 1,500 180,000 230 30,704 1913 2,078 216,160 1914 1,627 1916 876 273 308 362 38,266 69,544 1918 211 59,120 336 107,584 Before the war the price of cocoa was about £4 per cwt. 1 Coffee consists of the seeds of one of the Rubiacese (Coffea arabica) which grows naturally in Southern Ethiopia and Arabia,~and is cultivated on an enormous scale in India, the Antilles, Madagascar, and South America. It is an evergreen plant, 6 to 9 metres high and of pyramidal habit, with greyish branches and lanceolated leaves, the flowers (at the base of the leaf) being white and pleasant-smelling, like jessamine. The fruit forms drupes like cherries, the epicarp passing from yellow to green to red to brownish, and the mesocarp being yellow, pulpy and of agreeable taste. The endocarp is divided into two compartments surrounded by coriaceous membrane and each containing a seed, which has one convex and one flat, furrowed face, and is covered by a friable pellicle ; the endosperm (albumen ) is yellowish or greenish and horny. Coffee berries are composed of cellulose (18 per cent. ), fatty matters (12 per cent. ), gummy and saccharine substances (10 per cent.), nitrogenous compounds (12 per cent.), mine^jQ salts (4 to 5 per cent.), a tannin (caffetannic acid, 8 per cent.), caffeine (0-8 to 1-3 per cent.), caffearine, and water (11 per cent.). When roasted, coffee develops aroma and loses 15 to 20 per cent, in weight, but increases in volume by one-third, while the sugar caramelises and the cellulose carbonises partially, forming a brown oil which is denser than water, dissolves in ether, and constitutes the aromatic substance (caffeone). Roasted coffee contains, on the average, 1-5 per cent, of water, 13 per cent, of nitrogenous substances, 0-8 per cent, of sugars, 13-5 per cent, of fats, 4-8 per cent, of ash, 0-9 per cent, of caffeine, and 46 per cent, of non -nitrogenous substances ; to hot water this coffee gives up about 25 per cent, of its weight. The form of the seed varies with the kind of the coffee (Coffea mauritiana, laurina, liberica, etc. ). Mocha coffee berries are small and the Australian ones large, whilst those from the Antilles are intermediate in size. The quality of coffee is influenced by the methods of cultivation and preparation : by the ordinary or dry method the fruit is dried in the sun, so that it may be freed from the parchment- like membrane and partly from the silvery pellicle by beating in a husking machine. In the West Indies and Brazil, however, more use is now made of the wet process, in which the fresh fruit is carried by a stream of water into a de-pulping machine fitted with revolving channelled or toothed discs or cylinders, the seeds after this treatment being covered only with the parchment integu- ment and with a little pulp, which is eliminated by fermentation and subsequent washing ; finally COFFEE SUBSTITUTES 439 larger proportions occurring in the leaves of the tea plant (1-2 to 4 per cent.),1 in cola nuts (2 to 3 per cent. ), in mate leaves (or Paraguay tea ; about 1 per cent. ) and in guarana paste (made from the seeds of Paullinia sorbilis, grown in Brazil : 3 to 5 per cent. ). the seeds are dried in the sun or in an oven, and may then be freed from the parchment by de- corticating machines. One hundred kilos of fresh fruit gives about 20 kilos of berries for sale, these being rendered shiny by shaking them dry in sacks or in levigating apparatus, in which finely powdered colouring matters (indigo, ultramarine, chromium salts, curenin, graphite, etc. ) are often introduced. The cultivation of coffee has received a considerable impulse in Brazil, where as much as 800,000 tons (more than three-fourths of the total production of the world) is now produced. Of the Antilles coffees, the most highly valued is that from Porto Rico. The principal commercial varieties of coffee are named after the countries where they are grown. The output in different countries is as follows (tons ) : Brazil Other American countries Asia and" Oceania (except Arabia) Africa and Arabia Whole world 1900-1901 1904-1905 1909-1910. 1913-1914 675,700 632,000 1,150,000 680,000 170,000 181,400 36,000 85,000 46,100 39,500 26,000 36,000 11,300 8,200 1,500 (?) 1,000 (?) 910,000 861,000 1,300,000 850,000 (?) In 1902 the mean consumption per head in kilos amounted to : Holland, 6-6 ; Norway, 5-3 ; Sweden, 5-2; United States, 5-1; Belgium, 4-7; Denmark, 3-4; Germany, 3; France, 2-2; Austria, 0-9; Italy 0-5; Spain, 0-5; Great Britain,. 0-43. The total importation is as follows (tons ) : Belgium Holland Germany France (one-third (two-thirds g?',e Italy Spain re-exported) re-exported) 1 1907 189,600 53,596 101,570 113,350 117,857 426,487 21,476 11,292 1910 171,000 47,600 112,000 50,000 120,000 364,876 25,287 i 12,838 1912 171,000 34,200 111,240 50,000 116,250 427,516 27,627 13,378 1913 168,000 43,000 115,280 53,480 144,950 387,000 28,659 15,129 1914 — 52,680 116,420 124,950 458,620 28,197 13,733 1916 — 82,880 153,000 — 89,000 529,297 48,961 16,383 1918 — ; — • — — 51,638 , — In 1900 Italy imported 14,100 tons of coffee, in 1908 22,760, and in 1910 25,300 tons (£1,062,080) (about four- fifths from Brazil) ; the Customs' duty was £60 per ton until 1909, after which it was lowered somewhat. Pre-war prices per cwt. at Genoa, exclusive of duty, were : .Mocha, £4; Porto Rico, 72s. ; Peru, 50s. ; Salvador, 56s. ; San Domingo, 44s. (washed 60s. ) ; Santos, 42s. ; Rio, 38s. ; Bahia, 36s. In 1909, coffee became a State monopoly in Italy, the retail price being raised in January, 1920, to 14s. to 17s. (18 to 22 lire ) per kilo, according to the quality; before the war, the price was 3s. 6d. to 4s. Qd. (including Is. 2d. duty ). Coffee Substitutes. These are now numerous, and as a rule contain no caffeine, being obtained by roasting roots, saccharine fruits, cereals, leguminous seeds, etc. On roasting, the saccharine substances form caramel and other bitter substances giving colour, taste and smell to the aqueous decoction. Chicory coffee contains, on the average : water, 8 per cent. ; nitro- genous substances, 7 ; fats, 2-5; sugar, 16; non-nitrogenous extractives, 52 (9 per cent, induline and 12 per cent, caramel); cellulose, 10, and ash, 5 per cent.; about 65 per cent, is soluble in water. Beet coffee, carrot coffee, etc., are also sold, and in Germany and Austria large quantities of fig coffee are used, this being often mixed with coffee made from dates, carobs, lupins, wheat, rye, barley, maize, malt, acorns, chestnuts, arachis nuts, etc. These substitutes may be distinguished from coffee by microscopic examination, by their small proportion of fat (1 to 3 per cent., whereas coffee contains up to 14 per cent.), and by the high content of saccharine substances (3 to 50 per cent., while coffee contains 2 per cent, at most). 1 Tea is an evergreen shrub (Thea viridis, Thea bohea, and Thea assamica), cultivated in China, Japan, British India, Java, Ceylon, and Brazil. The leaves are similar to those of the white willow, and contain various enzymes, of importance being an oxydase which, under suitable conditions of temperature and moisture, transforms the green matter into a black substance (the tannins being oxidised ). The oxydase is more sensitive to heat than other enzymes producing the aroma, so that if the leaves are heated- for more than an hour at 70° for green tea or at 80° for black tea, the maximum aroma is developed, while the tannin (oxidised) and theine (volatilised) are diminished in amount and the soluble substances increased (Sawamura, 1912). For black tea 440 ORGANIC CHEMISTRY Industrially caffeine may be extracted from coffee, tea, or mate leaves, in which it is partly combined with tannic acid, by decomposing the compound with water and then treating with chloroform, which readily dissolves it (from coffee it may be extracted directly with benzene, which takes out the oil also ; after evaporation of the benzene, the caffeine is separated by means of water, the oil remaining insoluble ). Tea residues may be extracted directly with solvents such as alcohol, previous pulping with lime (as used in the case of guarana paste) not being always necessary. During the war a certain amount of caffeine was obtained in Italy by extraction of the soot deposited in the flues of the apparatus used for roasting' coffee. Synthetically caffeine may be prepared by methylating 3-methylxanthine, 1 : 7-dimethyl- xanthine (paraxanthine ) or 3 : 7-dimethylxanthine (theo bromine) by means of methyl iodide and caustic soda. Pure caffeine forms white, silky, odourless needles of bitter taste ; at 100° it loses the molecule of water of crystallisation, and it sublimes readily and melts at 228° to 230°. It dissolves readily in chloroform, to some extent in boiling water, slightly in alcohol or cold water, and very slightly in ether. It dissolves in acids forming unstable crystallisable salts. When heated gently to dryness with a little chlorine water and concentrated nitric acid, it leaves a reddish- yellow residue which gives a purple- violet coloration with a little ammonia. Before the war it cost £2 per kilo, but during the war it was sold in Italy at £ 12 (300 lire) per kilo. GUANINE, C5H5ON- (constitution given above), is a di-acid base, but forms salts also with bases. It is a white powder insoluble in water but soluble in ammonia. On oxidation with potassium chlorate and hydrochloric acid, it gives carbon dioxide, para- banic acid, and guanidine. the leaves ar§ allowed to wither and soften in the sun, and are then rolled up and covered with moist cloths to accelerate the fermentation, which transforms the green into black substances. Rolling of the leaves results in rupture of the cells and expression of the juice which facilitates the fermentation ; when the latter ceases (in a few hours) the material is spread either on iron plates heated over direct fire or on gratings heated with hot air (not over 80° ). To prepare green tea, the withered leaves are subjected to rapid treatment with boiling water or steam to destroy the oxydase (the enzymes producing the aroma are more resistant), so that the green colour may be preserved. The prepared tea is kept in sealed boxes of metal foil, in order that extraneous odours may not be absorbed. From 4 kilos of leaves 1 kilo of dry tea is obtained. Commercially the numerous varieties are grouped into three types : green, black, and scented, the last two being slightly fermented. The active alkaloid is Theine (see above). The best infusion of tea is obtained by macerating for thirty minutes in cold water and then adding boiling water, the liquid being poured off before it becomes very brown and excessively rich in tannin (20 grams of tea per litre of slightly hard water). The world's output of tea is about 600,000 tons, and is furnished almost entirely by Asia [55 per cent, from China and the rest from India (120,000 tons), Ceylon (85,000 tons), Japan (28,000 tons), Formosa, and Java]. The consumption of tea in different countries is shown by the following amounts imported (tons ) : Great Britain Belgium (one-sixth Eussia Trance Holland (two-thirds Spain Italy re-exported) fc re-exported) 1907 143,846 92,856 44,959 1,155 4,174 766 143 74 1910 150,522 70,172 44,501 1,261 4,970 749 156 74 1912 163,771 68,509 44,772 1,309 5,508 1,051 187 87 1913 165,580 78,513 40,378 1,207 5,467 586 214 95 1914 168,705 78,271 44,466 1,980 6,461 — 122 75 1916 171,306 78,400 47,522 2,645 8,185 — 202 106 Other imports were in 1913 (tons): Canada, 16,300; Austria, 2,000; Denmark, 467; Roumania, 350; Switzerland, 528; Argentine, 1880; Chili, 1746; Persia, 4770, and Australia, 16,940. Before the war, tea was sold in Italy at 3s. to 6s. per kilo (including the import duty of 2s. ), according to the quality. XAN THINE, ADENINE 441 XANTHINE, C5H4O2N4 (constitution given above), is a white powder and acts as both acid and base. It is obtained from guanine by the action of nitrous acid, and its lead salt reacts with methyl iodide, giving theo bromine. ADENINE, C5H5N5 (constitution given above), forms shining needles and is a base occurring in tea and in ox-pancreas. It is formed by decomposition of the nuclein of the cell-nuclei and is hence of physiological importance. INDEX ABRIN, 138 Abrus prrecatorius, 138 Acetaldehyde, 250 Estimation, 251 Acetals, 245 Acetamide, 238, 421 Acetamidine, 426 Acetamido-chloride, 425 Acetates, 345-348 Acetic anhydride, 380 Acetifiers, 342 Acetimino-chloride, 425 Acetiminothiomethyl hydriodide, 425 Acetins, 257, 274 Acetoacetaldehyde, 399 Acetobromamide, 420 Acetometers, 344 Acetonamines, 252 Acetone, 129, 254 Acetonealcohol, 397 Acetone-chloroform, 119 Acetonitrile, 238 Acetonylacetone, 399 Acetoxime, 252 Acetyl chloride, 379 iodide, 380 number, 224 sulphide, 419 Acetylacetone, 398 Acetylcarbinol, 397 Acetylcellulose, 381 Acetylene, 111 hydrocarbons, 110 Acetylethylamine, 420 Acetylglycocoll, 424 Acetylhydrazides, 426 Acetylides, 110, 361 Acetylurea, 433 Achroodextrin, 141 Acichlorides, 379 Acid, Abietic, 206 Acetaldehydedisulphonic, 257 Acetic, 328 Acetoacetic, 396 Acetonediacetic, 411 Acetonedicarboxylic, 411 Acetonetricarboxylic, 419 Acetonic, 389 Aceturic, 385, 424 Acetylenecarboxylic, 361 Acetylenedicarboxylic, 376 Aconitic, 376, 411 Acrylic, 354 Adipic, 357, 362 Alkylphosphonic, 242 Allanturic, 435 Allocroto'nic, 355 Allophanic, 433 Alloxanic, 435 •y-Allylbutyric, 357 442 Acid, Allylsuccinic, 373 Aminoacetic, 379, 385, 423 Aminoethylsulphonic, 257 a-Aminoglutaric, 424 a-Amino-j8-hydroxypropionic, 424 a-Aminoisocaproic, 424 o-Aminopropionic, 423 Aminosuccinic, 424 a-Amino-j8-thiolactic, 396 Amylacetylenecarboxylic, 360 Amylmalonic, 369 Angelic, 356 Arabonic, 392 Arachidic, 320 Aspartic, 424 Azelaic, 365, 372 Azulmic, 427 Barbituric, 435, 437 Behenic, 320 Behenolic, 360, 362 Brassidic, 360 Brassylic, 360, 365 Bromosuccinic, 374 Butylacetylenecarboxylic, 360 Butylfumaric, 373 Butylmaleic, 373 Butylmalonic, 369 Butylsuccinic, 371 Butyric, 348 Cacodylic, 242 Caffetannic, 438 Camphoronic, 376 Capric, 350 Caproic, 349 Caprylic, 349 Carbamic, 431 Carbaminic, 431 Cerotic, 351 Cetylmalonic, 369 Chloroacetic, 379 a-(B-, 7-) Chlorobutyric, 378 Chlorocarbonic, 431 o-(0-) Chloropropionic, 378 Citraconic, 22, 375 Citramalic, 400 Citric, 412 Citronellic, 357 Citrylideneacetic, 364 Crotonic, 22, 354 Cyanic, 427 Cyanoacetic, 377 Cyanuric, 428, 431 Cyclogeranic, 363 Decamethylenedicarboxylic, 365 Decoic, 350 Dehydroundecenoic, 361 Desoxalic, 419 Diacetosuccinic, 411 Diacetylenedicarboxylic, 376 Diacetylglutaric, 411 INDEX 443 Acid, Dialkylphosphonic, 242 Diallylacetic, 363 Dialuric, 435 oS-Diaminovaleric, 392 Diaterebinic, 400 j87-Dibromobutyric, 355 £j8-Dibromopropionic, 378 Dicetylmalonic, 369 Dichloracetic, 378 aa-(aB-) Dichloropropionic, 378 Diethylmaleic, 373 Diethylmalonic, 369 Diglycollic, 384 o8-Dihydroxybutyric, 355 Dihydroxymalonic, 410 ajS-Dihydroxypropionic, 392 Dihydroxystearic, 359, 390, 392 Dihydroxytartaric, 411 Diisoamylmalonic, 369 Diisobutylmalonic, 369 Dimethylacetic, 349 o0-Dimethylacrylic, 356 Dimethylarsenic, 242 Dimethylfumaric, 375 aa-(cr/-, 77-) Dimethylitaconic, 373 Dimethylmaleic, 375 Dimethylmalonic, 369 Dimethyloxaminic, 240 Dimethylparabanic, 436 Dimethylpseudouric, 436 Dimethylsuccinic, 371 Dioctylmalonic, 369 Dipropylmalonic, 369 Dithiocarbamic, 434 Dithiocarbonic, 433 Dithiocarbonylic, 433 Dodecamethylenedicarboxylic, 365 Elaeostearic, 364 Elaidic, 359 Erucic, 360 Erythric, 392 Ethanetricarboxylic, 411 Ethanthiolic, 419 Ethan thioltbiolic, 419 Ethylacetylenecarboxylic, 360 Ethylcarbonic, 431 Ethyleneaminosulphonic, 424 Ethyleaelactic, 389 Ethylenesuccinic, 370 Ethylfumaric, 373 Ethylhydroxamic, 427 Efchylideneacetic, 355 Ethylidenelactic, 386 Ethylidenepropionic, 356 Ethylidenesuccinic, 371 Ethylisopropylmalonic, 369 a-(7-) Ethylitaconic, 373 Ethylmaleic, 373 Ethylmalonic, 369 Ethylmethylacetic, 349 Ethylnitric, 236 Ethylsulphonic, 235 Ethylsulphuric, 108, 235 Ethylsulphurous, 235 Flaveanhydric, 427 Formic, 324 Formothiohydroxamic, 429 Formylacetic, 393 Fulminic, 428 Fulminuric, 429 Fumaric, 22, 374 Galactonic, 392 Geranic, 358, 363 Glucoheptonic, 393 Acid, Gluconic, 392 Glutaconic, 375 Glutamic, 424 Glutaric, 366, 372 Glyceric, 220, 392 Glycerophosphoric, 258 Glycolglycollic, 384 Glycollic, 379, 384 Glycolsulphuric, 256 Glycoluric, 433 Glycuronic, 393 Glyoxylic, 393 Gulonic, 392 Heptoic, 349 Heptylacetylenecarboxylic, 360 Heptylsuccinic, 371 Hexahydrostearic, 364 Hexantetroloic, 392 Hexylacetylenecarboxylic, 360 Hexylsuccinic, 371 Hippuric, 423 Hydantoic, 433, 435 Hydracrylic, 389 Hydrazoic, 426, 434 Hydrochelidonic, 411 Hydrocyanic, 427 Hydromucic, 373 Hydromuconic, 375 Hydroxyacetic, 379, 384 3-Hydroxyacrylic, 390, 393 o-(fl-)Hydroxybutyric, 389 a-Hydroxycaproic, 389 Hydroxycitric, 419 Hydroxyethylsulphonic, 257 o-(^)-Hydroxyglutaric, 400 a-Hydroxyisobutyric, 389 a-Hydroxyisovaleric, 389 Hydroxymalonic, 399 Hydroxymethylsulphonic, 257 o-Hydroxymyristic, 389 Hydroxyoleic, 390 a-Hydroxypalmitic, 389 j8-Hydroxypelargonic, 390 a-Hydroxypropionic, 386 i3-Hydroxypropionic, 389 o-Hydroxystearic, 389 Hydroxysuccinic, 399 a-Hydroxyvaleric, 389 Hypogaeic, 358 Ichthyolsulphonic, 103 Idonic, 392 Iminodithiocarbamic, 433 Iminodithiocarbonic, 433 Iminothiocarbamic, 433 ^-lodopropionic, 378 Isethionic, 257 Isoamylmalonic, 369 Isobutylaticonic, 375 Isobutylfumaric, 373 Isobutylmaleic, 373 Isobutylmalonic, 369 Isobutyric, 349 Isocrotonic, 22, 355 Isocyanic, 427 Isoerucic, 360 a-(/8) Isofulminuric, 429 Isolinolenic, 364 Iso-oleic, 359 Isopropylacetylenecarboxylic, 360 Isopropylfumaric, 373 7-Isopropylitaconic, 373 Isopropylmaleic, 373 Isopropylmalonic, 369 Isosaccharinic, 392 INDEX Acid, Isosuccinic, 371 Isovaleric, 349 Itaconic, 374 Itamalic, 400 Jecorinic, 364 0-Ketobutyric, 396 Lactic, 383, 386 Laurie, 320, 350, 362 Leucinic, 389 Levulinic, 390, 397 Lignoceric, 320 Linolenic, 364 Linolic, 363 Lyxonic, 392 Malamic, 421 Maleic, 22, 374 Malic, 399, 421. Malonic, 368, 437 d-Mannonic, 392 Margaric, 350 Melissic, 351 Mesaconic, 22, 374 Mesotartaric, 401 Mesoxalic, 399, 410 Metacrylic, 356 Metasaccharinic, 392 Methionic, 228, 257 Methylacetylenecarboxylic, 360 a-Methylacrylic, 356 3-Methylacrylic, 355 £-Methy]adipic, 372 Methylbutylmalonic, 369 l-Methylcyclohexylidene-4-acetic, 20 Methylenedisulphonic, 257 7-Methylene-7-methylpyrotartaric, 373 Methylenesuccinic, 374 Methylethylglycollic, 389 Methylethylitaconic, 373 Methylethylmaleic, 373 Methylethylmalonic, 369 Methylfumaric, 374 Methylisobutylmalonic, 369 Methylisopropylmaleic, 373 Methylisopropylmalonic, 369 a-(y-) Methylitaconic, 373 Methylmaleic, 374 Methylmalonic, 369 Methylmethyleneacetic, 356 Methylpropiolic, 361 Methylpropylmaleic, 373 Methylpropylmalonic, 369 Monochloroacetic, 379, 383 Monothiocarbamic, 433 Monothiocarbonic, 433 Monothiocarbonylamic, 433 Monothiocarbonylic, 433 Mucic, 410 Muconic, 376 Myristic, 350 Nitrohydroxylaminic, 246 Nonoic, 349, 360 Nonylacetylenecarboxylic, 360 (Enanthic, 934 Oleic, 358 Aa/3-Oleic, 359 Oxalacetic, 410 Oxalic, 366 Oxaluric, 435 Oxaniic, 421 Palmitic, 350 Parabanic, 435, 436 Paralactic, 389 Paratartaric, 401 Pelargonic, 349 Acid, Pentadecoic, 320 Pentylmalonic, 369 Perthiocyanic, 429 Picric, 303 Pimelic, 365 Pivalic, 349 as. Propanetricarboxylic, 411 s. Saturated monohydric, 124, 126 Secondary, 124, 125 Tertiary, 124. 125 Tetrahydric, 224 Trihydric, 217 Unsaturated, 216 Alcoholene, 178 Alcoholism, 130, 184 Alcoholometer, Gay-Lussac, 174 Tralles, 174 Alcoholometry, 174 446 INDEX Aldehyde-ammonias, 245 Aldehydes, 116, 124, 243, 244 Determination by Strache's method, 255 Schiff's reagent- for, 246 with unsaturated radicals, 251 Aldehydo-catalase, 134 Aldoketenes, 256 Aldol, 393 Aldols, 245 Aldoximes, 246 Alembics, 158 Algae, 68 Aliphatic compounds, 29 Alipine, 119 Alkoxides, 124 Alkyl halides, 114 Estimation of, 120 Alkylenes, 106 Alkylhydrazines, 241 Alkylhydroxylamines, 24 1 Alkylisoureas, 432 Alkyls, 30 Allantoin, 436 Allene, 109, 374 Alloisomerism, 21, 22 Alloxan, 435 Alloxanthine, 436 AHyl bromide, 123 chloride, 123 iodide, 123 isothiocyanate, 430 mustard oil, 430 thiocyanate, 430 Allylene, 110, 375 Amber, 370 Amidases, 183 Amides, 253, 419 of carbonic acid, 431 of hydro xy-acids, 421 Amidines, 238, 425, 426 Amido-chlorides, 425 Amidoximes, 427 Amimides, 42£ Amines, 239 Amino-acids, 419 Derivatives of, 422 Aminoguanidine, 434 Ammelide, 431 Ammeline, 431 Ammonal, 311 Ammoncarbonite, 307 Ammonium carbamate, 431 cyanate, 428 ichthyolsulphonate, 103 thiocyanate, 429 Amygdalin, 136 Amylacetylene, 399 Amylase, 133, 134 Amylene, 109 hydrate, 215 Amylo process, 155 Amylodextrin, 141 Amylomyces Rouxii, 155, 156 Anaesthesia, 114, 118 Anaesthetics, 118 Analysis, Elementary, 8 Qualitative, 7 Quantitative, 8 Anhydrides, 380 Internal, 380 Mixed, 380 Antialdoximes, 253 Anti-bodies, 138 Antiketoximes, 253 Antilactase, 138 Antimorphine, 138 Antipepsin, 138 Antirennet, 138 Antiricin, 138 Antiseptics, 151 Antitoxins, 138 Arabitol, 225 Arginine, 392 Aromatic compounds, 29 Arrack, 190 Arsines, 242 j^rtificial parthenogenesis, 138 Ascomycetes, 133 Asparagine, 20, 424 Aspartamide, 425 Aspergillus oryzae, 155 Asphalte, 99 Artificial, 99 mastic, 99 Asphaltite, 100 Astatki, 77, 86 Asymmetric syntheses, 137 , Asymmetry, Absolute, 22 Relative, 22 Atole, 190 Atractylin, 248 Attenuation of fermented liquids. Carbon sulphochloride, 433 tetrachloride, 122 Valency of, 15 Carbonic acid esters, 431 Carbonite, 284, 307 Carbonites, 306 Carboxyl, 124 Carbyl sulphate, 257 Carbylamines, 238 Cart-grease, 98 Castor oil, 390 Catalases, 135 Catalysts, Inorganic, 136 Organic, 136 Cellase, 134 Cerasin, 69, 105 Cereals, Starch-content of, 141 Cerotene, 109 Cerotin, 215 Ceryl cerotate, 216 Chamberland flasks, 147 Champy drums, 272 Charcoal, Wood, 268 Chartreuse, 190 Cheddite, 305 Chica, 190 Chlamydomucor oryzse, 155 Chloral, 251 hydrate, 251 Chloralamid<% 421 Chloramides, 238 Chloranhydrides, 379 Chloretone, 119 Chlorhydrins, 107, 217, 257 Chlorimides, 238 Chlorocruorin, 137 Chloroe thane, 117 Chloroform, 118 Pictet, 119 Tests for, 120 Chloromethane, 116* Chlorophyll, 133 Chloropicrin, 236 o-Chloropropylene, 123 Chocolate, 437 Cholestrophane, 436 Choline, 257 Chronograph, Le Boulenge's, 317 Cider, 190 Citral, 216, 252, 416 Citrates, 418 C'itromyces citricus, 412 Pfefferianus and Glaber, 412 Citronellal, 252, 358 Citronellol, 216 Citrus bergamia, 413 industry, 413 limetta, 413 limonium, 413 Classification of organic substances, 29 Coagulation, Enzymic, 134 Coal, Cannel, 100 -dust in mines, 34 for gas, 39 gas, 38 tar, 99 Cocaine, 119 Cocci, 133 Cocoa, 437 Coffee, 438 substitutes, 439 Cognac, 190, 191 Collodion cotton, 285, 294 Combustion furnace, 8 448 INDEX Condensation, Aldehyde, 245 Aldol, 245 Condenser, Liebig's, 2 Conductivity, Electrical, 29 Conidia, 133 Coniine, 20, 110 Conylene, 110 Coolers, Wort, 204 Cordite, 287, 302 Cracking of oils, 87 Cream of tartar, 401, 402 Creatine, 435 Creatinine, 435 Cremonite, 305 Creosote oil, 99 Crotonaldehyde, 252 Crotonylene, 110 Crushers, 262, 315 Crystalline form, 24 Crystallisation, 2 Crystals, Hemihedral, 19 Liquid, 139 Mixed, 23 Curacao, 191 Cyamelide, 427 Cyanamide, 18, 430 Cyanates, 427 Cyanide black, 104 Cyanides, Alkyl, 237 Cyano-acids, 377 Cyanogen, 427 chloride, 427 compounds, 427 of coal-gas, 50 sulphide, 429 trichloride, 427 Cyanohydrins, 238 Cyanurtriamide, 431 Cyclic compounds, 106 Cycloheptanone, 357 Cyclohexane, 71 Cyclo-olefines, 29 Cycloparaffins, 29 Cyclopentane, 71 Cyclopropane, 106 Cymene, 252 Cymogen, 37 Cynarase, 139 Cysteine, 396, 424 Cystine, 396, 424 Cytase, 134 Decane, 32 Degree of dissociation, 322 fermentation, 153 viscosity, 90 Degrees Brix, 153 Dehusker, 145 Denaturants, 177 Denatured alcohol, 176 Densimeter, Legal, 207 Dephlegmators, 77, 158, 162 Derricks, 66, 74 Desichthyol, 103 Desmobacteria, 133 Desmotropy, 18 Detonation, 258 Detonators, 309 Dextrase, 147 Dextrinase, 134, 204 Diacetamide, 421 Diacethydrazide, 426 Diacetyl, 398 Diacetylene, 114 Diacetylglycol, 217 Dialdehydes, 393 Diallyl, 110 Diamalt, 140 Diamino-acids, 424 Diastase, 133, 134, 141 Diastofor, 140 Diazo-compounds, 241 Diazoguanidine, 434 Diazomethane, 242 Dibutyramide, 421 Dicetyl, 32 Dichlorethane, 118 Dichlorhydrin, 257 Dichlormethane, 118 Dicyanodiamide, 431 Dieline, 122 Diethylamine, 241 Diethylcarbinol, 126, 243 Diethylcyanamide, 431 Diethylenediamine, 257 Diethylsulphone, 233 Diethylthiourea, 434 Diglycerol, 218 Diglycollamides, 421 Diglycollimide, 421 Dihydrazides, 426 Dihydroxyacetonase, 147 Dihydroxyacetone, 147, 398 Dihydroxydiethylamine, 257 Di-isobutyramide, 421 Diketobutane, 398 Diketohexane, 399 Diketonamines, 252 Diketones, 398 Dimethylacetamide, 420 Dimethylacetol, 398 Dimethylamine, 241 Dimethylarsenic acid, 242 chloride, 242 Dimethylarsine, 242 Dimethylcarbinol, 214 Dimethylethylcarbinol, 126, 215 Dimethylglyoximej 398 Dimethylmethane, 36 Dimethyloxamide, 240 Dimorphism, 24 Dinitroacetylglycerine, 274 Dinitroethane, 237 Dinitroformylglycerine, 274 Dinitroglycerine, 273 Dinitromethane, 237 Dinitromonochlorhydrin, 274 Diolefines, 109 Diplococci, 133 Dipropargyl, 114 Dipropionamide, 421 Distillation, Fractional, 2, 75 of fermented liquids, 158 Theory, 3 Vacuum, 4 Wood, 330 Distillery residues, Utilisation, 182 Disulphides, 233 Disulphoxides, 233 Dithioglycol chloride, 257 Dithiourethane, 434 Diureides, 435 Docosane, 32 Dodecane, 32 Donnar, 305 Dormiol, 119 Dotriacontane, 32 449 Dropping-point of fats, 0 Drying ovens for explosives, 271, 294 Dulcitol, 226 Durra, 141, 182 Dynamites, 273, 282 Analysis, 313 Gelatine, 298 Gelatinised, 2J>9 Gum, 298 Manufacture, 283 Properties, 284 Safety, 284 with active bases, 285 with inert bases, 283 Ebullioscope, 176 Echinochrom, 137 Effusiometer, Bunsen's, 62 Ehrlich's side chain theory, 138 Eicosane, 32 Electrical conductivity, 29 Emulsin, 134 Emulsor, Kuhlmann, 278 Enantiomorphism, 20 Enantiotropy, 130 Enzymes, 23, 133, 134 Equilibrated action, 136 Synthetic action, 136 Epichlorhydrin, 258 Erythrene, 109 Erythritol, 109, 225 Erythrodextrin, 141 Esters, 124, 234 Ethanal, 250 Ethanamide, 421 Ethanamidine, 426 Ethandial, 393 Ethandiol, 217 Ethane, 24, 36 Polychloro-derivatives of, 122 Ethanol, 130 Ethene, 108 Ethenol, 216 Ether, 228 Industrial preparation, 230 Petroleum, 37, 76 Properties, 228 Recovery from air, 231 Tests, 232 Uses, 231 Ethers, 226 Ethine,30, 111 Ethyl, 30 acetate, 395 acetoacetate, 395, 396 bromide, 115 bromopropionate, 369 carbonate, 431 chloride, 115, 117 chloracetoacetate, 397 chlorocarbonate, 431 chloroformate, 431 cyanurate, 427 diacetylsuccinate, 397 diazoacetate, 385, 424 dichloroacetoacetate, 397 fluoride, 115, 117 formate, 328, 395 hydrosulphide, 233 hydroxycrotonate, 394 iodide, 115, 117 isocyanate, 428 isocyanurate, 428 malonate, 368 VOL. Ethyl methyl ketone, 256 mustard oil, 430 nitrate, 235 nitrite, 235 oxalate, 240 peroxide, 232 hydrate, 232 phosphate, 234 sodioacetoacetate, 396, 397 sodiomalonate, 369 sodiomethylmalonate, 369 sulphate, 235 sulphide, 234 sulphite, 235 sulphoxide, 234 thioacetate, 419 thiocyanate, 429 Ethylacetamide, 420 Ethylacetamido-chloride, 425 Ethylacetimino-chloride, 425 Ethylacetylene, 110 Ethylamine, 241 ethyldithiocarbamate, 434 hydrochloride, 420 Ethylcarbinol, 214 Ethylcyanamide, 431 Ethylene, 106, 108 bromide, 118, 217 chloride, 118 cyanide, 256 iodide, 118 monothiohydrate, 257 oxide, 256 Polychloro-derivatives, 122 Ethylenecyanohydrin, 256 Ethylenediamine, 257 Ethylhydrazine, 246 Ethylidene chloride, 118 Ethylidene compounds, 118 Ethylideneacetone, 398 Ethylidenecyanohydrin, 238, 256 Ethylmagnesium bromide, 243 Ethylmercaptan, 233 Ethylsulphone, 234 Ethylurethane, 432 Etiline, 122 Eucaine, 119 Excelsior mill, 200, 269 Exhausters, 53 Explosion, 258 by influence, 265 Determination of, 264 Heat of, 259 Pressure of gases, 261 Velocity of combustion, 263 projectiles, 317 reaction, 263 Volume of gases, 261 wave, 262 Explosive, Favier's, 263, 304 Explosives, 258 Abel's test for, 314 Analysis of, 313 Charging density of, 262 Classification of, 266 Destruction of waste, 312 Non-congealing, 274, 276 Progressive, 263 Safety, 35, 305 Sensitiveness of, 315 Shattering, 263, 303 Sprengel's, 304 Stabilisation of, 292 Statistics of, 319 29 450 INDEX Explosives, Storage of, 312 Theory of, 259 Uses of, 318 Fats, Consistent, 90 Dropping-point of, 6 Fehling's solution, 255, 400 Fermentation, Alcoholic, 132, 145, 152, 204 Lactic, 151, 387 Fibrinogen, 137 Firedamp, 34, 305 Fishery statistics, 69 Fodder, Molassic, 166 Nutritive value of, 182 Forcite, 298 Formaldehyde, 247 Formalin (Formol), Analysis of, 247 Formamide, 421 Formates, 327 Formhydrazide, 426 Formins, 257 Formolite reaction, 71, 91 Formula, Constitutional, 15, 17 Empirical, 13 Structural, 15, 17 Formulae, Rational, 18 Unitary, 15 Formyl chloride, 379 Formyloxime chloride, 427 Francolite, 104 Fruit essences, Artificial, 349 Fulgurite, 284, 304 Fuller's earth, 80, 89 Fulminate of mercury, 308 Analysis of, 308 Fumaria officinalis, 374 Furfuraldehyde (Furfural), 173 Furnace, Combustion, 8 Gas, 45 Fusel oil, 109, 146, 165, 172 Fuses, 309 Bickford, 310 Electric, 311 Galalith, 250 Gafezin, 191 Gas, Air, 60 Blue, 58 Illuminating, 38 et seq* Marsh, 33 meters, 56 Oil, 65, 98 producer, 45, 60 Riche, 60 Water, 58, 98 Gases, Permanent, 34 Gasolene, 37, 76 Gasometers, 54 Gaultheria procumbens, 127 Gelatine, Blasting, 285 dynamites, 285, 298 Gelignite, 298 Geranial, 252 Geraniol, 216, 252 Gin, 190 Glass, Hardened, 94 Glonoin, 275 Glutarimide, 422 Glyceraldehyde, 393 Glycerides, 218 Glycerol (Glycerine), 36, 146, 217 Industrial preparation, 220 Qualities of, 223 Refractive index, 219 Glycerol, Statistics, 223 Tests for, 223 Uses, 220 Glycerose, 398 Glyceryl trinitrate, 258 Glycine (Glycocoll), 379, 385, 423 Glycocyamidine, 435 Glycocyamine, 434 Glycogen, 137 Glycol, 217 Glycol acetates, 256 chlorohydrin, 256 dinitrate, 256 Ethyl ethers of, 256 mercaptan, 257 Glycollamide, 421 Glycollic aldehyde, 393 Glycollide, 384 Glycols, 216 Propylene, 217 Glycolsulphuric acid, 256 Glycosine, 393 Glyoxal, 393 Glyoxaline, 393 Glyoxiline, 284 Goudron, 99 " Grains," 203 Grape must, 186 Greek fire, 266 Green naphtha, 102 oil, 103 Schweinfurth's, 348 Grisounite, 307 Guanamines, 434 Guanidine, 434 Amino derivative of, 434 Diazo, 434 nitrate, 434 Nitro-derivative of, 434 Guanine, 436, 440 Guncotton, 285 Compression of, 293 Manufacture of, 288 Properties of, 287 Pulping of, 292 Stabilisation of, 292 Thomson and Nathan's process for, 290 Uses of, 293 Gunpowder, 266 Manufacture, 267 Haemocyanin, 137 Hsemoerythrin, 137 Haemoglobin, 135 Halides, Acid, 377, 379 Halogens, Detection of, 7 Estimation of, 12 Hansena fermentation vessels, 208 Hardened glass, 94 Heat of combustion, 25 explosion, 259 formation, 25 of explosives, 259 neutralisation, 26 Hedonal, 119 Helianite, 328 Heneicosane, 32 Hentriacontane, 32, 37 Henze autoclaves, 143 Heptachloropropane, 123 Heptacosane, 32, 37 Heptadecarte, 32 Heptaldehyde, 251 Heptane, 32, 37 INDEX 451 Heracleum giganteum, 127, 130, 215 spondylium, 215 Heterocyclic compounds, 29 Hexacetylmannitol, 224 Hcxacontane, 32, 37 Hexacosane, 32 Hexadecane, 32 Hexadione, 399 Hexamethylbenzene, 111 Hexaraethylene, 106 Hexamethylenetetramine, 187, 248 Hexandiine, 114 Hexanes, 32, 37 Hexanhexol, 225 Hexanitroethane, 237 Hexanol, 215 Hexine, 110 Holocaine, 119 Homoasparagines, 425 Homology, 24 Hops, 193 Decoction of, 203 Humulus lupulus, 193 Hydantoin, 433, 435 Hydramine, 257 Hydraulic gas main, 45 press, 270 Hydrazides, 426 Hydrazodicarbonarnide, 434 Hydrazones, 246 Hydrocarbons, 29, 31 of petroleum, 71 of the CnH2n-2 series, 109 of the CnH2n-4 and CnH2n-6 series, 114 Saturated, 29, 31 Unsaturated, 29, 106, 116 with triple linkings, 1 10 Hydrogen, Estimation of, 8 Nascent, 33 Tyoical alcoholic, 124 Hydrolysis, 125, 442 Enzymic, 134 Hydroxy-acids, Higher, 389 poly basic, 419 Polyvalent dibasic, 399 monobasic, 391 tri basic, 411 Saturated monobasic, 383 Unsaturated monobasic, 389 /3-Hydroxybutyraldehyde, 245 Hydroxyethylamine, 257 Hydroxyethyltrimethylammonium hydrox- ide, 257 Hydroxylamine, 235 derivatives of acids, 427 Hydroxymethyleneacetone, 396, 399 Hydroxymethyleneketones, 399 Hydroxynitriles, 238 Hyphomycetes, 133, 155 Hypnotics, 118 Hypoxanthine, 436 Ichthyoform, 104 Ichthyol, 103 Ichthyolsulphonates, 103 Iditol, 226 Illuminating gas, 38 Analysis of, 60 Calorific value of, 39, 61 Composition of, 40 History of, 38 Lighting power of, 62 meters, 56 Physical and chemical testing of, 60 Illuminating gas. Separation of naphthalene from, 46 Statistics of, 59 Yield of, 58 Imides, 421 Iminocarbamide, 434 Iminocarbamideazide, 434 Iminochlorides, 425 Iminoethers, 420, 422 Iminothioethers, 425 Iminourea, 434 Index of refraction, 27 Injectors, Korting, 53 Invertase (Invertin), 134 lodoform, 121 reaction, Lieben's, 131 Tests for, 122 lodopropane, 117 lodourethane, 432 Ironac, 328 Isobutane, 37 Isobutyl iodide, 118 Isobutylcarbinol, 126, 215 Isobutyramide, 421 Isocyanates, 427 Isocyanides, 238 Isocyclic compounds, 29 Isoleucine, 424 Isology, 24 Isomaltose, 136 Isomelamine, 431 Isomerides, 17 Boiling-points of, 25 Melting-points of, 25 Metameric, 18 Optical, 20 Racemic, 21 Isomerism, 15, 17 Cis- and trans-, 22 Space, 19 Isonitriles, 237, 238, 240, 427 Isonitrosoketones, 253, 398 Isopentane, 37 Isoprene, 109, 113 Isopropyl iodide, 116, 117 Isopropylacetylene, 1 10 Isovaleryl chloride, 380 Isuret, 427 Ivory, Artificial, 351 Kephir, 139, 191 Kerosene, 72 Ketenes, 256 Keto-aldehydes, 394, 399 Ketoketenes, 256 Ketones, 116, 124, 243, 252 Strache's estimation of, 255 Ketonimides, 243 Ketoximes, 253 Beckmann's transposition of, 253 Kieselguhr, 275, 283 Kirschwasser, 190 Koji, 155 Koumis, 191 Kratites, 305 Kummel, 191 Laccase, 134 Lactams, 423 Lactases, 134 Lactates, 388 ' Lactic acid bacillus. 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