Production. When the flowers are distilled, traces of terpenes and the more readily volatile oxygenated and ester constituents pass over first. These are the bearers of the fragrance, whereas the later distillate consists largely of sesquiterpenes. In Luzon and sometimes in Java the first distillate is collected separately and brought into the market as ylang-ylang oil. The later distillate and the total distillate are called cananga oil.
On account of the delicacy of their fragrance, the gathering and distillation of the flowers require considerable skill and care. Hence but few distillers have succeeded in producing a ylang-ylang oil of uniformly good quality.
But little is known concerning the distilling apparatus used in Manila. The first requisite for the production of a superior oil are perfectly developed, fresh flowers. According to R. F. Bacon1) 350 to 400 kg. of flowers yield 1 kg. of oil of prime quality and 3/4 kg. of oil of second grade.
In Manila the oil which is distilled in the interior, viz., in Camarins, Mindoro and Albay is universally regarded as of inferior quality. However, this is due only to the primitive method of distillation. The flowers are in no way inferior to those raised in Manila. Indeed, some of the Manila firms distil oil in the interior for which they obtain the same price as for their other product. The distiller in the interior enjoys the great advantage of less competition, hence is in a position to buy the flowers at a lower price and to reject those of an inferior grade. With the use of modern apparatus and the application of rational methods of distillation, the ylang-ylang industry in the interior ought to be susceptible of considerable development.
1) Philippine Journ. of Sc. 3 (1908), A, 65 ff.; Report of Schimmel & Co. October 1908, 128 to 136.
The production of cananga oil in Java is described by A. W. K. de Jong1). Inasmuch as the distilleries are not located on the plantations, the flowers have to be carted to the stills. Previous to distillation the flowers are pounded. The body of the still consists of a copper boiler. It is provided with a pipe for the replacement of water during distillation. A copper helmet connects it with the condenser. The copper condensing tube which is about 15 cm. in diameter passes in a diagonal direction through a large earthenware jar filled with water. The condensation water is not replaced by fresh water when warm, but merely replenished upon evaporation. In place of a Florentine flask, a wine bottle with a small hole at the bottom is used for collecting the distillate. This bottle is placed into a copper vessel, filled with water, in such a manner that the neck of the bottle projects over the side of the vessel. The copper vessel in turn is placed in an earthenware pan into which the aqueous distillate is allowed to flow during the operation. The aqueous distillate is poured back into the still. A charge of flowers is distilled uninterruptedly for two days, but the condensation during the second day is imperfect.
This irrational method, which has been criticised in detail by C. von Rechenberg2), can yield but an inferior oil.
Composition. As already pointed out, ylang-ylang oil consists of the lower boiling portions of the oil rich in esters, whereas in the cananga oil the sesquiterpenes predominate. Hence the differences between the two oils are quantitative rather than qualitative.
The first investigation of ylang-ylang oil was conducted by H. Gal3) in 1873. From the saponification liquid he separated benzoic acid which occurs in the oil as ester. Later A. Reychler1) showed that acetic acid occurs in the oil likewise in the form of ester.
1) Teysmannia 190S, 578. Batavia; Report of Schimmel & Co. April 1903, 26.
2) Gewinnung und Trennung der atherischen 0/e. Miltitz b. Leipzig 1910, p. 450.
3) Compt. rend. 76 (1873), 1482.
Of alcoholic constituents, presumably partly combined with the two acids, l-linalool1) (b. p. 196 to 198°; d20o0,874; aD - 16°25') and geranio/1) (b. p. 230°; d20„0,885), the latter separated by means of its calcium chloride compound from the corresponding fraction, have been isolated. In addition to these two alcohols, p-cresol methyl ether1) Ch3c(,H4Och3 (b. p. 175°; m. p. of anisic acid 178°) contributes to the characteristic odor of the oil.
The high boiling fractions contain cadinene1) (m. p. of dichlorhydrate 117°) which is found in larger amounts in cananga oil. This sesquiterpene is accompanied by an odorless and colorless substance2) which crystallizes in needles melting at 180° and which apparently belongs to the class of the sesquiterpene hydrates. Additional investigations have been conducted by Schimmel 8j Co. These constitute the basis of an artificial ylang-ylang oil*) which has been placed upon the market. In the lowest boiling fractions they found c/-«-pinene4) (m. p. of nitrol benzylamine 123°).
An important part, as bearers of the perfume, is played by several phenols5), viz., eugenol (m. p. of benzoate 70 to 71°), isoeugenol") (m.p. of benzoate 103 to 104°; m. p. of acetate 79 to 80°) and probably creosol"). Eugenol is present not only as such but also as eugenol methyl ether7) (m. p. of veratric acid 180°).