258 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS T,tst.• 1 length, Approximate Mode of Microns Intensity Functional Group Vibration Present in 2.92 Strong Tertiary OH (bonded) Stretching (Linalool) 3.00 Strong Primary OH (bonded) Strteching Others 3.23 Weak Terminal C=C C--.H stretch Linalool 3.44 Strong CH Stretching All 5.40 Weak -- C--•-CH2 Overtone Lin alool 5.8'i Strong Ester Carbonyl Stretching Impurities 5.97 Medium C•C Stretching Geraniol, Nerol, Rhodinol 6.08 Medium C•-C terminal Stretching Linalool 6.90 Strong CH Bending All 7.08 Medium C•-•-C terminal Deformation Linalool 7.28 Strong CHa Bending All 7.93 Weak Tertiary OH Bending Linalool CHq, 8.12 Weak NC/ Bending All except Citro• CHa / • nellol 8.30 Weak Tertiary OH Bending Linalool 9.00 Strong Tertiary OH Bending Linalool 9.04 Weak Primary OH Bending All except Linalool 9.16 Weak Primary OH Bending All except Linalool 9.45 Strong Straight chain alcohol ... Not present in puri- and Citronellol fled Geraniol 10,00 Strong C=C Deformation Except Lina[ool 10.90 Strong C•---C terminal Deformation Linalool 11.28 Weak Straight chain alcohol .., Impurities 11.97 Weak CHa•c/ Deformation Except Citronellol 12.88 Weak C=C Deformation Except Linalool 13.50 Weak Methylene Rocking All 14.55 Medium C=C terminal Deformation Linalool frequencies different from primary hydroxyls, especially in the 7-10 micron region. 3. There is no apparent evidence of cis- and trans-isomerism between this sample of nerol and rhodinol in spite of the fact that this isomerism usually gives characteristic frequency differences for other infrared applications. However, according to Naves the main difficulty is in pre- paring a true nerol cis-isomer of geraniol and, if successful, such isomer- ism will show in the region fi'om 8-15 microns. 4. Rhodinol does not seem to be a compound of a given chemical struc ture such as listed in Table I, but rather a mixture of citronellol, geraniol, :" and others. 5. Most of these C-10 alcohols seem to contain some straight chain primary alcohol as an impurity which can be removed in the calcium chloride purification process. 6. Various combinations of methyl groups can also be located by infra- red spectroscopy. Figure 12 shows geranyl acetate and a geranyl distillation residue to illustrate some of the frequently encountered impurities.

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I I l I I I I II1 I I I I1• Ill I II 111 I I I I I IIIlllll I I I I I I i I I I I I I I I I it)Ill I I I [Vl•l I I Vl _U • i I I I I Ilillll• I I I I I I I I I t I I I I I illlift I I I I IX• I •1 • i, ] t i i 111111]11 i i t I I I I I I •1 I•l I I I I I I I\lt'l •LI I I I II I I'1•1111/11 II I III II II II I II I•11 IIII I I II II I•1 -•LLI I I I I !111111111 111 111 I[ II II I I I I•1 ß .4-t.!,,,]] [,[•[[I[[ [[][] t[[] I I CITRONELLOL' 2 3 4 5 6 7 8 9 t I000 I 900 i1•11 iio 1 7,50 '•' IIIIIIIIIIIIII IIIII IIII IIII1111111111111111111111111111 I I I I I I I kl•l I I I I I I LJ I•11 I I I I I I I I 111 I I I I • I I/,,l.,J,•t"'•l I I 1.4 r• I I I I { I I I I I ILI I I I I ILl I I tl/1 I"d I Jr'•'.,I--l-,i'•l.'•l'=F I I I.I I I I II11 I lift I 'lF't4g.'l..,'tM • IX, I'll I 1\1 I/I I I I I [ k I I 1,-,111 [ I I I I II•111,1 I I I I I I I I I • III I I I I I1111,!-.•fl I I11 I I•I•11 I II III I II N/Ill I I I I"• I/IA,'x! I III I I IXI I I I I I I I I I I I I I I I I I I I I I• I•11(A I I Ill I I tl I I I ] I I lll 111111 I I I I I•\1 I1/I i I III I I I I I I• .•,•ul• ] •, H*--LINALOOL II1•1 I1! I Ill Ill . t./l',JXltll IIII III I I I I I I I I 11111111 III I I I II [I, itl I III II I I I I I I I I I I I I I I I I I I I I I I 1111".4'11111111111111111111111111111 I0 II 12 13 14 15 Figure 9.--Inoerared spectra of rhodinol, geraniol, citronellol and' linalool, and nerol.