146 



II. CHEMISTRY OF FATTY ACIDS AND GLYCEROL 



Table 48 records some of the physical constants for the fatty halides which 

 have been investigated. Densities reported^ are somewhat higher than for 

 the corresponding fatty acids. The figures (di) for some of these are as 

 follows: butyryl chloride, 1.0277^°; valeryl chloride, 1.0155^^; heptanoyl 

 chloride, 0.95219^"; caprylyl chloride, 0.94000''''; and nonanyl chloride, 

 0.93353^". The refractive index has been reported for butyryl chloride as 

 as 1.41209 (wf ) and for heptanoyl bromide"" as 1.4605 (nf). 



Table 48 



Freezing Points and Boiling Points of Acid Chlorides of Some Saturated and 



Unsaturated Acids'" 



" Largely adapted from A. W. Ralston, Fatty Acids and Their Derivatives, Wiley, 

 New York, 1948, p. 809. 



^ P. E. Verkade, Rec. trav. chim., 62, 393-397 (1943). 



« The superior numbers refer to the barometric pressure in millimeters of mercury at 

 which the boiling point was determined. 



c'. Reactions of Acid Halides: These compounds are highly reactive, 

 and hence they find wide application in the synthesis of many fatty acid 

 derivatives. They react with alcohols to form esters (see page 114). On 

 treatment with ammonia or amines, they form amides or substituted 

 amides (see page 136). Nitriles can likewise result from this reaction. 

 They are especially useful in the sjmthesis of ketones by the application of 

 the Friedel-Craft reaction (see page 143). 



On reduction of the halides in the presence of metallic platinum, pal- 

 ladium, or nickel oxide, the fatty acid aldehydes are formed: 



»TO A. Kirrmann, Ann, chim. [10], 11, 223-286 (1929). 



