372 IV. WAXES, HIGHER ALCOHOLS, ETC. 



of esters of unsaturated monatomic alcohols with unsaturated acids. They 

 may be solidified by elaidinization with nitrous acid, whereby the cis form 

 of the unsaturated acid is changed to the trans modification. The most 

 common member of this group is sperm oil. However, a bird oil from the 

 mutton-bird {Aestrelaia lessoni),^^^ and a vegetable wax (jojoba wax) also 

 possess a similar composition. 



True sperm oil is a pale-colored liquid wax from the head oil of the sperm 

 whale (Physeter macrocephalus) , which is also the source of spermaceti. 

 This product is sometimes referred to as spermaceti oil or cachalot oil.^ 

 Arctic sperm oil is a closely related product obtained from Hyperoodon 

 rostratus. The latter product is also known as bottlenose oil and doegling 

 oil. Dolphin oil, obtained from Delphinus delphis, is also a liquid wax but 

 it contains considerable amounts of triglycerides admixed with it. 



Sperm oil has a low specific gravity; the value at 15°C. is 0.880-0.883.^*^ 

 A saponification value of 123-133, and iodine numbers of 81-84 have been 

 reported. Table 14 shows the approximate composition of a typical oil. 



Table 14 

 Composition of Sperm Oil" 



Component Formula Per cent 



Mvristvl caprate CH,3(CH2)i2CH20-OC(CH2)8CH3 4.5 



Cetyllaurate CH3(CH2)i4CH,OOC(CH.,)ioCH3 20.0 



Hexadecenyl lauroleate CieH^O-OCCuH,! 7.0 



Oleyl myristate CH3(CH2)7CH:CH(CH2)7CH,0-OC(CH2),2CH, 13.0 



Olej'l myristoleate CH3(CH2)7CH:CH(CH2)7CH20-OCCi3Ho5 18.0 



Cetyl palmitate CH3(CH2),4CH>0-OC(CH2)hCH3 9.0 



Hexadecenyl palmitoleate CieHsiO -000151129 3.0 



Oleyl oleate OH3(OH2)70H:OH(CH2)70H.O- 



00(OH2)70H:OH(OH..)70H3 11.0 



Stearyl stearate CH3(OH.>)ieOH20-00(OH2)i6CH3 2.5 



Eicosenyl eicosenate O20H39O -0001911:17 7.0 



Eicosenyl eicosdienoleate O20H39O-OOO19H35 2.0 



Undetermined ■ 3.0 



° Adapted from A. H. Warth, The Chemistry and Technology of Waxes, Reinhold, New- 

 York, 1947, p. 87. 



In addition to the constituents reported in Table 14, sperm and Arctic 

 sperm oil contain small proportions of the glyceryl ethers, batyl, chimyl, 

 and selachyl alcohols (see page 392). 



c. Natural Waxes from Plants. The waxes serve as protective agents 

 on plant leaves. The outer wall of the epidermis of an adult plant leaf 



3*0 L. H. Smith, J. Sac. Chem. Ind., 30, 405 (1911). 



3^1 G. Martin, Animal, Vegetable Oils, Fats and Waxes, Orosby, Lockwood <fe Son.s. 

 London, 1920. 



