Epoxidizable Fatty Amide–Phenol Conjugates

Abstract

This paper reports the synthesis of a series of novel compounds where carboxylic acids have been linked to a phenol through amidomethyl units. For instance, one, two, or three fatty acids have been selectively appended to the phenol in yields above 75%. The fatty acid used was oleic acid, which was subsequently epoxidized. Other functional groups, such as amino acids, can be incorporated in these compounds. Examples of monomers that are suitable for polymerization were also prepared: one acrylamide, one styrene derivative, and two types of AB 2 diamino acids, all of which contain oleic units that are sites for epoxidation and crosslinking. Fatty acid aryl ethers were prepared using hydroxy fatty acids. These molecules are intended to serve as augmented analogues of epoxidized vegetable oil. Their amide groups should lead to intermolecular aggregation through hydrogen bonding, and the option to covalently include other functional groups may permit tuning of the macroscopic materials properties of films, coatings, or solids constructed from them.

Synthesis of fatty acid conjugates with phenols, carbohydrates, amines, and CH‐acidic compounds by Pd(0)‐catalyzed allylic substitution

“…Further syntheses of conjugates with fatty acids and with a carbohydrate using other strategies are described in Refs. [8][9][10].…”

“…This way with the O-nucleophiles: methanol, phenols, carbohydrates, a-tocopherol, and estradiol the corresponding substitution products were obtained as mixture of regioisomers ( Table 2, Nr. [1][2][3][4][5][6][7][8][9][10][11][12]. With the N-nucleophiles: picolylamine and piperidine, and the C-nucleophiles: dimethyl malonate, nitromethane, methyl acetoacetate, and malodinitrile the corresponding Pd(0)catalyzed C-N-and C-C-bond formations could be achieved ( Table 2, Nr.…”