268 FISHERY INDUSTRIAL PRODUCTS 



ethers of fatty alcohols from sardine oil, as well as certain vegetable oils, 

 have been investigated as successful water paints. 



Potential Uses of Fish Oils 



Much research has been done to provide additional products by chemi- 

 cal modifications of fish oils. These products may serve as finished mate- 

 rials for end uses or as raw materials for the formulation of other finished 

 products. Sometimes products of basic research have no immediate use 

 but only await further exploitation through an advancing technology. The 

 remainder of this chapter will summarize a variety of different modifica- 

 tions of fish oils that may become important commercial assets to the 

 fish oil industry of tomorrow. 



Epoxides are important industrial materials used as protective coatings, 

 adhesives, and vinyl plasticizers". Epoxy menhaden oil has been prepared 

 and tested as a plasticizer for polyvinyl chloride ^2, 31 t^qqi results from 

 these studies showed good compatibility with and stability of PVC when 

 epoxy menhaden oil is used as a plasticizer. Whale oil has also been in- 

 vestigated for its value as an epoxy oiP. Epoxidized oils have a use also 

 in the oiling and waterproofing of leathers^ 



Fatty alcohols from menhaden oil can be readily produced^^'^^ Jan- 

 gaard and Ackman^^ reported the properties and preparation of fatty 

 alcohols by the lithium aluminum hydride reduction method from the 

 oils of cod, cod liver, seal, herring, and dogfish liver. Preparations of fatty 

 alcohols by this method cause the least amount of change in the ethylenic 

 bonds from fish oils than any other method. Sardine oil fatty alcohols 

 have been prepared and separated into several fractions of iodine values, 

 ranging from 120 to 346 ^''. Using fatty alcohols as synthetic intermediates, 

 alkyl halides, silicones, and quaternary ammonium salts have been pre- 

 pared from fish oils and certain pure fractions. Saturated alkyl bromides 

 derived from menhaden oil and unsaturated alkyl bromides from pilchard 

 oil have been produced along with the corresponding triethylalkylammo- 

 nium bromides. Trichloroalkylsilanes have been synthesized from n-hexa- 

 decyl, n-octadecyl, and oleyl bromides, as well as from the fish oil alkyl 

 bromides. SiUcones were derived from the corresponding trichloroalkyl- 

 silanes by a two step hydration-dehydration process^^. 



A heat-stable protective coating from fast drying fish oils can be postu- 

 lated from such products as alkoxypolysiloxanes prepared from the cor- 

 responding polyunsaturated long chain fatty alcohols. Olsen and Chris- 

 tenson^" report such polysiloxanes from soybean oil fatty alcohols. 



Fish oils can be used to prepare several types of non-soap detergents. 

 Hill and co-workers-'^ reported fatty alcohols from sardine and menhaden 

 oils in connection with their investigation of the detergent properties of 



