2‐Fatty Acrylic Acids: New Highly Derivatizable Lipophilic Platform Molecules. (1st April 2014)

• Record Type: Journal Article
• Authors: Zerkowski, Jonathan A.; Solaiman, Daniel K. Y.
• Is Part Of: Journal of the American Oil Chemists' Society. Volume 91:Number 7(2014)
• Page Start: 1225
• Page End: 1233
• Publication Date: 2014-04-01
• Subjects: Oleochemistry -- Surfactants -- Detergents -- Biobased products; Oils and fats -- Periodicals; Soap -- Periodicals; Fats -- Periodicals; Food-Processing Industry -- Periodicals; Acides gras -- Périodiques; Aliments -- Industrie et commerce -- Périodiques; Huiles et graisses -- Périodiques; Savon -- Périodiques; Oliën; Chemie; Oils and fats; Soap; Periodicals; 547.77
• DOI: 10.1007/s11746-014-2459-5
• Languages: English
• ISSNs: 0003-021X

Abstract

Abstract: This paper reports the incorporation of an alpha‐methylene unit into fatty acid skeletons. Since the new olefin is conjugated with the carboxylate, it is susceptible to 1, 4‐(Michael) additions. We have used multifunctional thiols and amines for additions at the methylene. The resulting products possess clusters of functionality grouped at one end of a hydrophobic tail. These structural patterns will be of use in the design of new types of bio‐based surfactants and polymers. One particularly promising pattern of functionality that can be obtained through oxidation and reduction chemistry is a 2‐fatty 1, 2, 3‐propanetriol, or a lipophilized glycerol moiety.