Alkylene Oxide-Adducted Hydrocarbyl Amides

Abstract

Provided herein are products produced by: a) reacting a C 4 -C 30 fatty acid or fatty acid lower alkyl ester with a mono- or di-hydroxy hydrocarbyl amine to form a hydrocarbyl amide; b) reacting the hydrocarbyl amide with alkylene oxide; and c) extracting the product of b) with water, acidic water, or water-containing inorganic salts or a combination thereof at a temperature from about 5° C. to 95° C. to yield an alkylene oxide-adducted hydrocarbyl amide having less than 2 wt % of amine-by-products.

1 . A product produced by the process comprising
 a) reacting a C 4 -C 30  fatty acid or fatty acid lower alkyl ester with a mono- or di-hydroxy hydrocarbyl amine to form a hydrocarbyl amide;   b) reacting the hydrocarbyl amide with alkylene oxide; and   c) extracting the product of b) with water, acidic water, or water-containing inorganic salts or a combination thereof at a temperature from about 5° C. to 95° C. to yield an alkylene oxide-adducted hydrocarbyl amide having less than 2 wt % of amine-by-products.   
     
     
         2 . The product produced by the process according to  claim 1 , wherein the fatty acid is a C 6 -C 24  fatty acid. 
     
     
         3 . The product produced by the process according to  claim 1 , wherein the fatty acid is a C 6 -C 20  fatty acid. 
     
     
         4 . The product produced by the process according to  claim 3 , wherein the fatty acid is coconut oil fatty acid. 
     
     
         5 . The product produced by the process according to  claim 1 , wherein the lower alkyl group on the fatty acid lower alkyl ester has about 1 to 6 carbon atoms. 
     
     
         6 . The product produced by the process according to  claim 5 , wherein the lower alkyl group on the fatty acid lower alkyl ester has about 1 to 4 carbon atoms. 
     
     
         7 . The product produced by the process according to  claim 6 , wherein the lower alkyl group on the fatty acid lower alkyl ester has about 1 to 2 carbon atoms. 
     
     
         8 . The product produced by the process according to  claim 7 , wherein the lower alkyl ester is a methyl ester. 
     
     
         9 . The product produced by the process according to  claim 1 , wherein the mono- or di-hydroxy hydrocarbyl amine is selected from the group consisting of ethanolamine, diethanolamine, propanolamine and dipropanolamine. 
     
     
         10 . The product produced by the process according to  claim 9 , wherein the hydrocarbyl amine is a di-hydroxy hydrocarbyl amine. 
     
     
         11 . The product produced by the process according to  claim 10 , wherein the di-hydroxy hydrocarbyl amine is diethanolamine. 
     
     
         12 . The product produced by the process according to  claim 1 , wherein the hydrocarbyl amide is a coconut oil fatty acid amide. 
     
     
         13 . The product produced by the process according to  claim 12 , wherein the coconut oil fatty acid amide is obtained by the reaction of coconut oil fatty acid or lower alkyl ester and diethanolamine. 
     
     
         14 . The product produced by the process according to  claim 1 , wherein the alkylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, pentylene oxide, or mixtures thereof. 
     
     
         15 . The product produced by the process according to  claim 14 , wherein the alkylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, or a mixture thereof. 
     
     
         16 . The product produced by the process according to  claim 15 , wherein the alkylene oxide is propylene oxide. 
     
     
         17 . The product produced by the process according to  claim 1 , wherein the alkylene oxide-adducted hydrocarbyl amide has from about 1 to 30 moles of alkylene oxide per mole of hydrocarbyl amide. 
     
     
         18 . The product produced by the process according to  claim 17 , wherein the alkylene oxide-adducted hydrocarbyl amide has from about 2 to 20 moles of alkylene oxide per mole of hydrocarbyl amide. 
     
     
         19 . The product produced by the process according to  claim 18 , wherein the alkylene oxide-adducted hydrocarbyl amide has from about 2 to 10 moles of alkylene oxide per mole of hydrocarbyl amide. 
     
     
         20 . The product produced by the process according to  claim 1 , wherein the alkylene oxide-adducted hydrocarbyl amide is derived from the reaction of a coconut oil fatty acid amide with ethylene oxide or propylene oxide. 
     
     
         21 . The product produced by the process according to  claim 1 , wherein the temperature of the extraction of product b) is from about 5° C. to 50° C. 
     
     
         22 . The product produced by the process according to  claim 1 , wherein the temperature of the extraction of product b) is from about 5° C. to 30° C. 
     
     
         23 . The product produced by the process according to  claim 1 , wherein the alkylene oxide-adducted hydrocarbyl amide has less than 1.5 wt % amine by-products. 
     
     
         24 . The product produced by the process according to  claim 1 , wherein the alkylene oxide-adducted hydrocarbyl amide has less than 1.0 wt % amine by-products. 
     
     
         25 . The product produced by the process of  claim 1 , wherein the amine by-products may be diethanolamine, alkoxylated diethanolamine or mixtures thereof. 
     
     
         26 . The product produced by the process according to  claim 25 , wherein the alkoxylated diethanolamine is propoxylated diethanolamine.