2,3-Dihydroxybutanedioic Acid → 3,4-Dihydroxy-1-(9Z)-9-octadecen-1-yl-2,5-pyrrolidinedione

Participants

Reaction Conditions

Reaction Steps

150 Parts of tartaric acid (obtained from Sargent Welch) is added to 173 parts of toluene and the mixture is heated with stirring to 100° C. 281 parts of Armeen O (essentially oleylamine, a product of Armak Chemicals, Chicago, Ill.) is added slowly and in small portions while the system is kept under nitrogen purge. After the addition of the Armeen O is completed the contents are heated to 130° C. at which temperature the water formed is removed by azeotroping, and collected. The temperature is then raised to 160° C., after no more water is collected and kept at about 160° C. for one hour under nitrogen purge to remove the toluene. The liquid residue is then filtered through diatomaceous earth to yield the desired N-oleyltartarimide. Analysis shows nitrogen content of 3.42% and hydroxyl content of 8.33%. The tartarimide can be expressed as ##STR4##

Provenance & Evidence