USES OF INDUSTRIAL FISH OILS 269 



fatty alcohol sulfates. One potentially important type is sulfated fatty 

 acid monoglycerides^. Mono and diglycerides and their acetylated prod- 

 ucts have been prepared from the oils of menhaden, tuna, herring, sardine, 

 and salmon eggs^^. 



Polyunsaturated aliphatic aldehydes have been prepared from the 

 methyl esters of menhaden oil fatty acids ^^ The corresponding acy loins 

 were used as the intermediates in the synthesis. Reduction of acyloins 

 were made to yield mixed ''symmetrical" glycols from menhaden oil. Both 

 the acyloins and the glycols are unique products of fish oil. 



Investigations with fish oils lead to a novel method for the preparation 

 of hydroxylated products. Autoxidized fish oils were shown to give hy- 

 droxylated products on treatment with thiourea. Methyl oleate hydro- 

 peroxide with a peroxide value of 6050 was converted to an oil having a 

 peroxide value of 56 by this method ^^ 



Fish oil is reported to be a suitable raw material for commercially 

 produced nitriles and amines''^ 



Fish oils and fish oil fatty acids should better serve as raw materials 

 for the synthesis of new chemical products if the raw materials are frac- 

 tionated into less complex and purified mixtures. This approach has been 

 taken to a limited extent by industry to provide such materials as select 

 chain length fatty acid mixtures, e.g., Cis — C20 partially hydrogenated 

 fatty acids. Similarly, industry provides destearinated fish oils, which can 

 be considered as a partial fractionation to provide a more uniform product. 

 Recently, Gruger^^ reported the investigation of several commercially im- 

 portant fractionation methods that provide purified and less complex mix- 

 tures of fatty acids from fish oils. These fractions of fatty acids from the 

 whole oil can be put to better use through chemical modifications by 

 employment of select reactions that take advantage of the uniqueness of 

 the particular acids. 



LITERATURE CITED 



1. Am. Patents Corp., German patent 1,015,186 (Sept. 5, 1957). 



2. Anon., Com. Fisheries Rev., 18, No. 9, 13(1956). 



3. Anon., J. Am. Leather Chemists' Assoc, 53, 65(1958). 



4. Bailey, B. E., Carter, N. M., and Swain, L. A., "Marine Oils with Particular 



Reference to Those of Canada," Bulletin No. 89, pp. 286-310; Ottawa, Fisheries 

 Research Board Can. (1952). 



5. Barrett, B., Leather Trades Rev., 75, 1125(1942). 



6. Biswas, A. K., and Mukherji, B. K., /. Am. Oil Chemists' Soc, 37, 171(1960). 



7. Bonney, R. D., and Egge, W. S., U.S. Patent 2,050,646 (Aug. 11, 1936). 



8. Cooke, S. R. B., Iwasaki, I., and Choi, H. S., A.I.M.E. Trans., 214, 920(1959); 



A.I.M.E. Trans., 217, 76, (1960). 



9. Dybakova, N. A., Zilberman, E. N., and Berlin, A. A., Chem. Abstr., 54, 



8114e(1960). 



