When chlorlyptus is dissolved in concentrated sulphuric acid, some blackening occurs and the odor of hydrogen chloride is very noticeable. Both the Abbott and Squibb brands of chlorinated eucalyptol give a reddish mixture, with no perceptible evolution of hydrogen chloride, and still retain the characteristic eucalyptol odor.
On heating, chlorlyptus decomposes and begins to boil at from 103 to 105 C. Then a higher fraction comes over at 178 C. The distillate has a sharp odor, is acid, and frees very little iodine from potassium iodide. Chlorinated eucalyptol-Abbott does not seem to decompose. Some gaseous substance is given off at 80 C, but the liquid distills at 173 C. The distillate has no acid odor, is neutral, and liberates no iodine from potassium iodide. (In both cases the distillation was not carried to completion, approximately only about half of the volume being distilled over.)
PRELIMINARY TESTS ON CHLORLYPTUS AND CHLORINATED EUCALYPTOL
| Chlorlyptus | Chlorinated Eucalyptol-Abbot | Chlorinated Eucalyptol-Squibb | |
| Odor | Acrid | Like eucalyptus | Like eucalyptus |
| Density and color | Dark brown; viscous, heavier than water | Light yellow; mobile; lighter than water | Colorless; mobile; lighter than water |
| AgNO3 added to alcoholic solution | Heavy ppt. | Slight turbidity | Clear |
| Equal parts with KI solution | Gives free iodin slowly, noticeable in 1⁄2 hour | Gives free iodin in 4 hours; not much | No free iodin in 4 hours |
| Equal parts with 10% KI, 10% KIO3 solution | Much iodin immediately | Small amount of free iodin in few numbers; does not noticeably increase | No free iodin in 3 hours |
| Equal parts with conc. H2SO4 | Some blackening; odor of HCl | Reddish mixture; no HCl; eucalyptol odor | Same |
| Alcohol KI | No iodin liberated | Same | Same as Abbott product |
| Heating | Decomposes and boils at 103–105 C.; then higher fraction comes over at 178 C.; distillate has sharp odor, is acid, but frees very little I2 from KI; distillation not completed | Apparently does not decompose; some gas given off when T=80; the liquid distilled at 173 C.; the distillate did not have much odor; no HCl gas detected; no I2 from KI; distillate was neutral (distillation not completed) |
The addition of chlorlyptus to a mixture of 10 per cent. potassium iodide, 10 per cent. potassium iodate solution, brings about the liberation of iodine, increasing perceptibly on standing. This shows that the hydrogen chloride is gradually split off, and in time will cause a solution having a considerable degree of acidity. When this test is carried out on chlorinated eucalyptol-Abbott, a small amount of iodine is liberated in a few minutes but does not increase, showing a slight initial acidity without further hydrolysis. Chlorinated eucalyptol-Squibb yields no free iodine after standing three hours.
When the chlorine content of chlorlyptus is determined according to the method of Carius, the amount is found to be 29.6 per cent. (The manufacturers give a method of determining chlorine by Hunter’s fusion method. It is believed that in this method hydrogen chloride may be lost, and this opinion is substantiated by the firm’s statement, “Chlorlyptus analyzed in this manner shows approximately 25 per cent. of chlorine.”) The chlorine content of chlorinated eucalyptol-Abbott is found to be 0.67 per cent., and that of the Squibb brand to be 0.62 per cent. (about one-fiftieth as much as in chlorlyptus).
To sum up: Chlorlyptus differs from chlorinated eucalyptol in odor, color, density, in reaction to silver nitrate, potassium iodide, sulphuric acid and the aqueous solution of potassium iodate and potassium iodide. The distillation of the two products occurs differently. Chlorlyptus contains nearly 30 per cent. of chlorine, which is approximately fifty times as much as in chlorinated eucalyptol. Thus it appears to have considerable chlorine in the negative form (Cl-) which may be relatively easily split off as hydrogen chloride.