112 Report of Schimmel $ Co. 1922. - 



text-book 1 ) serves best for qualitative tests (formation of iodoform) and for approximate 

 quantitative determinations (shaking out a fairly large portion with water or salt solution). 



The process devised by Verley and Boelsing 2 ) for the quantitative estimation of 

 alcohols and phenols (more especially of santalol, menthol, and eugenol) has been 

 re-examined by H. W. van Urk 3 ). The result was this that none of the substances 

 mentioned above can be estimated accurately by that method. Since years ago we 

 entered fully into the details of the process and found it to be unreliable 4 ) we con- 

 sider it unnecessary to occupy ourselves furthermore with van Urk's publication. 



In order to determine the amount of phenols in essential oils the method devised 

 first by Gildemeister 5 ) for testing thyme oil and improved later on by us 6 ) has, in 

 general, proved satisfactory; it consists in shaking 10 cc. oil in a cassia flask of fully 

 100 cc. capacity with a caustic soda solution of 3 or 5 per cent, and calculating the 

 phenol content from the amount of the oil dissolved in the lye. W. H. Simmons 7 ) 

 proved by way of experiment, that with thyme and cinnamon leaf oils 5 cc. oil on 

 treatment with a 5 per cent, caustic potash lye, give a distinctly higher proportion of 

 phenols than when 10 cc. of the oils are employed. Hitherto, the author was unable 

 to prove with certainty whether the lower or the higher values were the correct ones. 

 Comparative tests with clove, bay, and pimento oils gave the same results with 5 or 

 10 cc. oil. (On the whole, too strong lyes give too high results, since the lye, in 

 connection with the phenol alkali, dissolves also part of the non-phenols. For this 

 reason, we shake some oils, e.g., clove oil, with a caustic solution of but 3 per cent.) 



With the object to determine the composition of mixtures of eugenol and iso- 

 eugenol, in the preparation of vanillin from eugenol, P. V. McKie 8 ) constructed a curve 

 illustrating the melting points of mixtures of pure eugenol and pure isoeugenol ben- 

 zoates, m. p. 69.5 and 104° respectively, following the method described in a previous 

 paper ). A well-marked eutectic point was observed at a temperature of 56.5°, 

 corresponding with a composition of 25.5 per cent, of isoeugenol benzoate. Although 

 at temperatures from 83 to 86°, and at compositions approximating to the equimolar 

 mixture, the curve showed a discontinuity, the use of the melting point as a means 

 of determining the composition of mixtures is thereby not invalidated. 



The authoress obtained the esters by dissolving the crude oil, resulting from the 

 isomerisation of eugenol, in pyridine, and treating with some 25 per cent, excess of 

 benzoyl chloride. The major portion of the benzoates separates as a solid, and a 

 further quantity on pouring the pyridine solution into dilute sulphuric acid. The 

 resulting benzoates were dissolved in ether, from which, on evaporation of the ether, 

 the solid benzoate mixture is obtained. 



When, years ago 10 ), we estimated citronellol according to the formylation method, 

 we found that part of the alcohol undergoes a change. In order to elucidate this 

 reaction, A. St. Pfau 11 ) formylated each 100 gr. of citronellol (b. p. 105° [7.5 mm.], 

 6 months' old preparation) by boiling for one hour with each 200 cc. of '100 per cent, 

 and of 85 per cent, formic acid. The formylation products (ester v. 295.4 = 96.4 per cent, 



l ) Gildemeister and Hoffmann, The Volatile Oils, 2 nd ed., vol. I, p. 612. — 2 ) Cf. Report April 1902, 25. 

 — ») Pharm. Weekblad 58 (1921), 1265. As per Chem. ZentralU. 1921, IV. 1145. — *) Cf. Report April 1903, 

 27. — 5 ) Hager, Fischer and Hartwich, Kommentar zum Arzneibuch f. d. Deutsche Reich, 3. Ausg. Berlin 1892, 

 1 st ed., vol. I, p. 377. — 6 ) Report April 1907, 119. — 7 ) Per fum. Record 12 (1921), 394. — 8 ) Journ. chem. 

 Sac. 119 (1921), 777. — 9 ) Ibid. Ill (1918), 799. — 10 ) Cf. Report October 1913, 64. — u ) Journ. f. prakt. 

 Chem. N. F. 102 (1921), 276. 



