TERPENES was an aas-trimethylcarballylic acid, a conclusion which was A vast amount of work has been done on the constitution of HOC-CH-C(CH) (CO2H)-C(CH2)2CO2H, a conclusion confirmed by its synthesis (see below). The Bredt ROC-CH-C(CH), CH-COR (1) ROC CH C(CH) C(CH) CO2R CCH») C(CH) COB ROC CH (3) (CH)C(COH) C(CO:H) (CH) CH COH (CH)C(COR) C(CN)(CH) This series of reactions leads to a complete synthesis of camphor, since A. Haller (Comptes rendus, 1896, 122, p. 446) has shown that camphoric anhydride (1) on reduction yields campholid (2), which by the action of potassium cyanide and subsequent hydrolysis of the nitrile formed is converted into homocamphoric acid (3), the calcium salt of which yields camphor (4) on distillation: CH,CO(4)CH(CH2) (J. E. Marsh, Jour. Chem. Soc., 1899. 75. p. 1058). When heated with phosphorus pentoxide to 115-130° C. it forms metacymene. Since it does not yield any oxymethylene compounds, it cannot contain the grouping-CH, CO-in the molecule." HYDROCARBONS, C10H14, OF THE TERPENE SERIES Menthene, CH,(CH) (C,H), is methyl-1-isopropyl-4-cyclohexene-3. It is obtained by the action of anhydrous zinc chloride or copper sulphate on menthol (J. W. Brühl, Fer., 1892, 25. p. 142), by boiling menthyl chloride with aniline (G. Wagner, Ber., 1894, 27, p. 1636), by heating menthyl chloride with potassium phenolate (L. Masson, Ber., 1896, 29, p. 1843), and by the dry distillation of the Thus camphor and its oxidation products are to be represented as methyl ester of menthyl xanthate (L. Tschugaeff, Ber., 1899, 32, C(CH) () CH C(CH2) -CO (B), CH, C(CH,) COH, Camphoric acid, Camphor, Camphor yields three classes of halogen substitution derivatives known respectively as a, B and compounds, the positions being shown in the formula above. The a compounds result by direct substitution, the B and derivatives being formed in an indirect manner. Cyancamphor, CiH1O-CN, is formed by passing cyanogen gas into sodium camphor, or by digesting sodium oxymethylene camphor with hydroxylamine hydrochloride (L. Claisen, Ann., 1894, 281, p. 351). -Camphor sulphonic acid results from the action of fuming sulphuric acid on camphor (F. S. Kipping and W J. Pope, Jour. Chem. Soc., 1893, 63, p. 573). Camphoroxime, CiH16O:NOH, was first prepared by E. Nageli (Ber., 1883, 16, p. 497). 1-Camphor is formed by the action of nitric acid on l-borneol (W. J. Pope and A. W. Harvey, Jour. Chem. Soc., 1901, 79, p. 76). -Camphor melts at 178-179° C. (for its preparation see A. Debierne, Comptes rendus, 1899, 128, p. 1110; W. A. Noyes, Amer. Chem. Jour., 1905, 27, p. 430). Camphoric acid. Four optically active and two inactive forms of this acid are known. The most important is the d-form, which is produced by the oxidation of d-camphor with nitric acid. It crystallizes in plates or prisms which melt at 187° C. Potassium permanganate oxidizes it to oxalic acid and Balbiano's acid, CHO, together with small quantities of camphanic, camphoronic and trimethyl succinic acids. It yields two series of acid esters, the allo-esters (1), formed by the partial saponification of the neutral esters, and the ortho-esters (2), formed by heating the anhydride with alcohols or sodium alcoholates. CH2 CH COR Camphoric acid results on oxidizing -borneol or matricaria camphor. It melts at 187° C. -Camphoric acid is formed on mixing alcoholic solutions of equimolecular quantities of the dsad i-acids, or by oxidizing i-camphor. It melts at 202-203° C. Camphoronic acid, CHO. From a study of its distillation products J. Bredt (Ber., 1893, 26, p. 3049) concluded that this acid Myrcene, C10H16, was first isolated by F. B. Power and C. Kleber from oil of bay (Schimmel & Co., Bulletin, April 1895, p. 11); it is also found in oil of sassafras leaves. It is obtained from bay followed by fractionation in vacuo. It boils at 67-68° C. (20 mm.), oil by shaking the oil with a 5 per cent. solution of caustic soda, and polymerizes when heated for some time. When oxidized by potassium permanganate it yields succinic acid. By the action of is produced, which on hydrolysis yields myrcenol, C10H18O, an alcohol glacial acetic acid in the presence of dilute sulphuric acid, a liquid which is probably an isomer of linalool (P. Barbier, Comptes rendus, as being (CH3)2CCH (CH2)2 C(: CH2) CH. CH2 (Enklaar, Bul1901, 132, p. 1048). The hydrocarbon is probably to be considered letin of Rouse-Bertrand fils, Nov., 1906, p. 92). Ocymene is an isomer cit.) represents it as (CH3)2C: CH CH, CH C(CH) CH. CH2. which can be extracted from the leaves of the basil. Enklaar (loc. Anhydro-geraniol, CH, the first olefine terpene isolated, was prepared in 1891 by F. W. Semmler; it is formed when geraniol is heated with potassium bisulphate to 170° C. ALCOHOLS, ALDEHYDES AND KETONES or 2-6 dimethyl-octene-1-ol-8 occurs in Réunion geranium oil and d-Citronellol, CoH9OH or CH, C(CH2)-(CH2), CH(CH1)·(CH2),OH, was first prepared by F. D. Dodge (Amer. Chem. Jour., 1889, 11, p. 463) by reducing the corresponding aldehyde (d-citronellal). It is an odorous oil which boils at 117-118° C. (17 mm.). Oxidation by chromic acid mixture converts it into citronellal, whilst which is useful for identifying citral. The crude citral où- a more drastic oxidation with potassium permanganate yields acetone | with potassium bisulphate it forms para-cymene. It combines with Linalool, CHOH,or(CH2),C:CH· (CH2), C(CH1)(OH) CH: CH2, is 2.6-dimethyloctadiene-2-7-ol-6. d-Linalool was first found in coriander oil, and -linalool in oil of linaloe. It is also found in oil of bergamot, petit-grain, lavender, neroli, spike, sassafras leaves and lemon, either in the free condition or as esters. It is a pleasantsmelling liquid which boils at 197-199° C. (according to its source). The inactive variety can be prepared from geraniol, this alcohol on treatment with hydrochloric acid yielding a mixture of chlorides, which when digested with alcoholic potash are transformed into i-linalool (F. Tiemann and F. W. Semmler, Ber., 1898, 31, p. 832). It is oxidized by chromic acid to citral. When shaken for some time with dilute sulphuric acid it yields terpin hydrate. Citronellal, CHO, is the aldehyde of citronellol. It is a constituent of many essential oils, and was first discovered in citronella oil by F. D. Dodge (Amer. Chem. Jour., 1889, 11, p. 456); it is also found in eucalyptus oil and in lemon-grass oil. It is a dextrorotatory liquid which boils at 203-204° C. It is readily reduced by sodium amalgam to citronellol, and oxidized by ammoniacal silver oxide to citronellic acid. Potassium permanganate oxidizes it to acetone and B-methyladipic acid. It forms a dimethyl acetal, CoHis(OCH), which on oxidation with potassium permanganate yields a dioxydihydro-citronellaldimethyl acetal, CH,C(CH,OH)(OH)-(CH,),CH(CH,).CH, CHO, which must possess the above composition, since on further oxida- Ionone, CNO. By condensing citral with acetone F. Tiemann (Ber., 1893, 26, p. 2691) obtained pseudo-ionone (1), an oil of boiling-point 143-145° C. (12 mm.), which on boiling with sulphuric acid is converted into a mixture of the isomeric a- and B-ionones (2 and 3) (r) (CH3)C:CH (CH) C(CH3);CH CHÍCH CÓ CH C(CH) H.C H.C (2) H.C C CH CH1 a-Ionone is an oil which boils at 127-128° C. (12 mm.) and possesses a characteristic violet odour. The B-compound boils at 128-129° C. (10 mm.) and possesses a similar odour. They are largely used in perfumery. An isomer of ionone is irone, the odoriferous principle of the iris root. It boils at 144° C. (16 mm.). When heated with hydriodic acid and phosphorus it yields the hydrocarbon irene, CisHis (F. Tiemann, loc. cit.). SESQUITERPENES Juniperus oxyeldrus), cubeb, patchouli, galbanum, cedar-wood and Cadinene, CH4, is found in the oils of cade (from the wood of juniper. It may be obtained by fractionating oil of cade, con verting the crude hydrocarbon into its dihydrochloride and decomposing this by boiling with aniline. It is an oil which boils at 274-275° C. and decomposes on exposure. Caryophyllene is found in oil of cloves and in oil of copaiba balsam. Various other sesquiterpenes have been described, e.g. zingiberene (from essence of ginger), cedrene (from oil of cedar-wood), santalene (from oil of sandal-wood), humulene and clovene. Of the sesquiterpene alcohols pure santalol, CHO, has beɛn obtained from essence of sandal-wood by conversion into the acid phthalic esters and saponification of these by potash (Schimmel &Co, Bulletin, April 1899, p 41). A mixture of two alcohols is thus obtained, one boiling at 165-167° C. (13 mm.) and the other at 173° C. They are distinguished by their different optical activities, one being practically inactive, the other strongly laevo-rotatory (see also M. Guerbet, Comptes rendus, 1900, 130, p. 417: Bull. Soc. Chim. 1900 (3), 23. p. 540). Caryophyllene alcohol is obtained from oil of cloves; by elimination of water it yields clovene, CH. # liquid which boils at 261-263° C. Many di- and tri-terpenes have been described, but as yet are not thoroughly characterized. References.-Gildemeister and Hoffman, The Volatile Oils (Mit waukee, 1900); R. Meldola, The Chemical Synthesis of Vital Products (London, 1904); F. W. Semmler, Die aetherischen Oele (Leipzig. 1906); G. Cohn, Die Riechstoffe (Brunswick, 1904); J. M. Klimont, Die synthetischen und isolirten Aromatica (Leipzig, 1800); and F. Heusler, Die Terpene (Brunswick, 1896). For camphor see A. Lapworth, Brit. Assoc. Rep. for 1900, and O. Aschan. Die Kon stitution des Kamphers (Brunswick, 1903). (F. G. P.) Fig. 4. Greek Terracotta Statuettes. 1-3, from Tanagra (3rd century B.C.), 4-7, from Rhodes and Sicily (Archaic period). TERRACE (Fr. terrace, terrasse, from It. terraccia, | supported by massive arched substructures, which extend under terrazza, Lat. terra, earth), a raised platform of earth; in the surrounding houses. The cathedral of SS. Pietro e Cesareo, geology the term is used of level horizontal ridges on the side fronting upon it, is ensconced in a temple of Rome and Augustus, of a slope, formed by volcanic action, or more usually by the part of the side wall of which, with engaged columns, is still action of water; they are thus frequent along the shores of visible. "The vestibule, in the Cosmatesque style, is supported lakes or by rivers; on the seashore they are generally known by ten ancient columns resting upon recumbent lions, with a as "raised beaches." The term is used in architecture of an mosaic frieze upon them. The brick campanile has small artificial platform in front of a building, which is utilized as a columns with little pointed arches. The interior has a fine proraenade; sometimes, when the building is erected on an Cosmatesque pulpit supported by ancient columns resting on elevation, there may be a series of terraces rising one above the lions, a Paschal candlestick of 1245, and a good pavement of other, with flights of steps leading from one to the other, as in the same period with beasts and dragons. The sacristy contains the Villa D'Este at Tivoli; or there may be a single terrace a carved wooden nuptial chest of the 10th or 11th century raised high above the ground and supported on arches, as the There are also remains of the town wall in the " polygonal" terrace to the Adelphi buildings in the Strand, or the river style, and above the town are several massive platforms for front at Somerset House, or in France at the castles at Amboise supporting buildings, in a more archaistic form of this style; and St Germain-en-laye, or again a low terrace like that in these may well belong to the Roman period, and the latter even front of the Houses of Parliament at Westminster overlooking to the empire. The summit of the promontory (748 ft.) is the Thames, which is 670 ft. long and 35 ft. wide. The terraces reached by the old line of the Via Appia, which is flanked by of the gardens at Isola Bella on the Lago Maggiore are known tombs and by remains of an ancient defensive wall with circular as hanging gardens (Hortus pensilis), and were similar to those towers (currently attributed to Theodoric, but probably a which were built by the Assyrian king at Babylon, Though good deal earlier in date). The summit is occupied by a massive properly applied to a row of buildings on a raised level, the word terrace, supported by arcades of fine opus incertum (traditionally, is often used of any row of houses. but wrongly, called the palace of Theodoric) on all sides except the E., and commanding a magnificent view seaward over the coast and over the Pomptine Marshes. On the terrace, as was ascertained in 1894, stood a Corinthian temple of the early imperial period, 110 by 65 ft.; the cella was decorated internally with engaged half-columns, and contained the pedestal for the statue of the deity, according to some authorities Venus, but more probably Jupiter Anxur worshipped as a child-a theory confirmed by the discovery of many curious leaden toys, like those made for dolls' houses at the present day, in the favissae on the E. of the temple. Of the lower town by the harbour, which had buildings of some importance of the imperial period (amphitheatre, baths, &c.), little is now visible, and its site is mainly occupied by a new quarter built by Pope Pius VI., who restored the Via Appia through the Pomptine Marshes. Close by it in the S.W. is a group of huts inhabited in winter by labourers from the Abruzzi, as is the case in many other parts of the Campagna. Of the ancient harbour constructed by Antoninus Pius (M. R. de la Blanchère in Mélanges de l'école française de Rome, i. 322; 1881) insignificant remains exist, and it is largely silted up. Close to it is the small modern port. Near the amphitheatre was found in 1838 the famous statue of Sophocles now in the Lateran museum. The commune of Terracina includes a considerable extension of territory towards the N.W. with much undergrowth (macchia) valuable for charcoal burning, and a considerable extent of pasture and arable land. The ancient aqueduct, bringing water some 35 m. from the slopes of the Volscian Hills, has been repaired and is in use. Three miles to the N.W., at the foot of the Monte Leano, was the shrine of the nymph Feronia, where the canal following the Via Appia through the marshes ended. Along these 3 m. of the Via Appia are numerous ancient tombs, and the fertile valley to the N.E. was thickly populated in Roman days. See M. R. de la Blanchère, Terracine (Paris, 1884). (T. As.) TERRACOTTA. Greek. The use of clay amongst the Greeks was very varied and extensive, but we are here only concerned with one aspect of it, that in which the clay was baked without any glaze, whether employed for utilitarian or ornamental purposes. The Greek term for this is yn brη, "baked earth"; the word ŋλós when applied to worked clay signifies sun-dried only. Among the manifold purposes to which terracotta was put by the Greeks may be mentioned parts of public and private buildings, such as bricks, roof tiles, drain and flue tiles, and architectural ornaments; tombs and coffins; statues and statuettes, for votive or sepulchral purposes or for the decoration of houses; imitations of metal vases and jewelry; and such everyday objects as spindle whorls, theatre tickets, lamps, braziers and domestic utensils. It also supplied the potter with moulds and the sculptor with models of works of art, especially in bronze. TERRACINA (Lat. Tarracina, Volsc. Anxur), a town and episcopal see of the province of Rome, Italy, 76 m. S.E. of Rome by rail (56 by the Via Appia), 40 ft. above sea-level. Pop. (1901) 7597 (town), 10,995 (commune). Its position, at the point where the Volscian Hills reach the coast, leaving no space for passage between them and the sea, commanding the Pomptine Marshes (urbs prona in paludes, as Livy calls it) and possessing a small harbour, was one of great strategic importance; and it thus appears very early in Roman history. It appears in 509 B. C. as under Roman supremacy, but is not included in the list of the Latin league of 499 B.C. In 406 it was stormed by the Romans, lost in 402, recovered in 400, unsuccessfully attacked by the Volscians in 397, and finally secured by the establishment of a colony of Roman citizens in 329 B.C. As such it frequently appears in history. The construction of the Via Appia in 312 B.C. added to its importance: the road at first crossed the hill at the back of the promontory by a steep ascent and descent. An attempt was made in 184 B.C. to get round it by an embankment thrown out into the sea: but it was probably not until early in the imperial period that a cutting in the rocks at the foot of the promontory (Pisco Montano) finally solved the problem. The depth of the cutting is indicated by marks on the vertical wall at intervals of 10 Roman ft.-figures enclosed in large swallow-tail tablets--the lowest mark, 3 or 4 ft. above the present road, is CXX. Not far off are mineral springs by the coast (Neptuniae aquae), known to the Romans and still in use-except one containing arsenic which was blocked up both by the ancients and again in 1839 as a precaution. The two roads met some few miles E. of Tarracina, and the Via Appia then traversed the pass of Lautulae, between the mountains and the Lake of Fondi, where the Samnites defeated the Romans with loss in 315 B.C. This pass, the frontier between the Papal States and the kingdom of Naples, was also fortified in modern days. It was probably in consequence of the cutting just mentioned that some of the more important buildings of the imperial period were erected in the low ground by the shore, and near the small harbour. The construction of the coast road, the Via Severiana, from Ostia to Tarracina, added to the importance of the place; and the beauty of the promontory with its luxuriant flora and attractive view had made it frequented by the Romans as early as 200 B.C. Galba and Domitian possessed country houses here. It appears in the history of the Gothic wars, and Theodoric is said to have had a palace here. It was sacked in 409 and 595. In 872 John VIII. brought it under the domination of the Holy Sec. The picturesque modern town occupies the site of the old; the present piazza is the ancient Forum, and its pavement of slabs of travertine with the inscription "A. Aemilius A. F.," in letters once filled in with bronze, is well preserved. It is XXVI II⭑ |