Corrosion-inhibiting additives and methods of making and use thereof

Abstract

Additives, and methods of making and using the additives are described. The additives may be provided as concentrates for addition to one or more hydrocarbons in crude oil refining and processing facilities to inhibit corrosion of corrodible metal parts in contact with the process streams. The additives may be made by reacting glycerol-restricted vegetable oil fatty acid with amine, wherein the glycerol-restricted vegetable oil fatty acid may be a hydrolyzed vegetable oil that is at least partially purified with respect to glycerol. The additives may be further reacted to provide ammonium salts that may be added to aqueous compositions to provide corrosion protection of corrodible surfaces in contact with the aqueous compositions.

1 . An additive composition comprising a plurality of amides and/or ammonium salts thereof, wherein at least a portion of the plurality of amides comprises a reaction product derived from a first set of reactants comprising first one or more glycerol-restricted vegetable oil fatty acids and a polyamine,
 wherein the first one or more glycerol-restricted vegetable oil fatty acids comprise 0 percent by weight to 0.1 percent by weight of glycerol with respect to the weight of the first one or more glycerol-restricted vegetable oil fatty acids, and   wherein the polyamine has the formula NH 2  (CH 2 CH 2 NH) x CH 2 CH 2 NH 2  wherein x is 0 to 100.   
     
     
         2 . The additive composition of  claim 1 , wherein x is zero to ten. 
     
     
         3 . The additive composition of  claim 1 , wherein the first one or more glycerol-restricted vegetable oil fatty acids comprise glycerol-restricted soybean oil fatty acid. 
     
     
         4 . The additive composition of  claim 1 , wherein the additive composition further comprises a plurality of esters, wherein at least a portion of the plurality of esters comprises a second reaction product derived from a second set of reactants comprising second one or more glycerol-restricted vegetable oil fatty acids and one or more tertiary amines, each of the one or more tertiary amines having at least one hydroxyl group,
 wherein the second one or more glycerol-restricted vegetable oil fatty acids comprises 0 percent by weight to 0.1 percent by weight glycerol with respect to the weight of the second one or more glycerol-restricted vegetable oil fatty acids.   
     
     
         5 . The additive composition of  claim 4 , wherein the one or more tertiary amines comprises triethanolamine. 
     
     
         6 . The additive composition of  claim 4 , wherein the second one or more glycerol-restricted vegetable oil fatty acids comprise glycerol-restricted soybean oil fatty acid. 
     
     
         7 . The additive composition of  claim 1 , wherein the one or more first glycerol-restricted vegetable oil fatty acids and the second one or more glycerol-restricted vegetable oil fatty acids consist of glycerol-restricted soybean oil fatty acid comprising 0 percent by weight to 0.1 percent by weight glycerol with respect to the additive composition. 
     
     
         8 . The additive composition of  claim 1 , wherein the additive composition comprises 0 percent by weight to 0.1 percent by weight glycerol with respect to the additive composition. 
     
     
         9 . The additive composition of  claim 1 , wherein the polyamine comprises tetraethylenepentamine (H 2 NCH 2 CH 2 NHCH 2 CH 2 NHCH 2 CH 2 NHCH 2 CH 2 NH 2 ). 
     
     
         10 . The additive composition of  claim 1 , wherein each of the first one or more and second one or more glycerol-restricted vegetable oil fatty acids independently comprises about 2 percent by weight to about 15 percent by weight alpha-linolenic acid, about 46 percent by weight to about 56 percent by weight linoleic acid, about 17 percent by weight to about 28 percent by weight oleic acid, about 1 percent by weight to about 10 percent by weight stearic acid, and about 5 percent by weight to about 15 percent by weight palmitic acid with respect to the first one or more glycerol-restricted vegetable oil fatty acids and the second one or more glycerol-restricted vegetable oil fatty acids respectively. 
     
     
         11 . The additive composition of  claim 1 , wherein the additive composition comprises 0 percent by weight to 5 percent by weight of total imidazoline content, 0 percent by weight to 5% rosin acid, 0 percent by weight to 5 percent by weight of total derivative of rosin acid, 0 percent by weight to 5 percent by weight total C1-C10 monohydric alcohol, and 0% to 5 percent by weight total fatty acid ester content with respect to the additive composition. 
     
     
         12 . The additive composition of  claim 1 , wherein the additive composition comprises the plurality of amides and heavy aromatic naphtha. 
     
     
         13 . The additive composition of  claim 1 , wherein
 (i) the additive composition comprises the ammonium salts of the plurality of amides; and   (ii) the additive composition is aqueous.   
     
     
         14 . The additive composition of  claim 13 , wherein the ammonium salts of the plurality of amides comprise at least a portion of a reaction product derived from reactants comprising:
 (a) the plurality of amides, and   (b) one or more of an acid, an alkyl halide, and an aryl halide.   
     
     
         15 . A hydrocarbon composition comprising:
 (a) one or more hydrocarbons; and   (b) an additive composition comprising an ester composition,
 wherein the ester composition comprises a plurality of esters, wherein at least a portion of the plurality of the esters comprises a reaction product derived reactants comprising one or more glycerol-restricted vegetable oil fatty acids and one or more tertiary amines, each of the one or more tertiary amines having at least one hydroxyl group, 
   wherein the one or more glycerol-restricted vegetable oil fatty acids comprises 0 percent by weight to 0.1 percent by weight glycerol with respect to the weight of the second one or more glycerol-restricted vegetable oil fatty acids.   
     
     
         16 - 31 . (canceled) 
     
     
         32 . A method of inhibiting the corrosion of a surface in contact with one or more hydrocarbons, the method comprising combining an inhibitor composition with the one or more hydrocarbons, wherein the inhibitor composition comprises the additive composition of  claim 1 . 
     
     
         33 - 39 . (canceled) 
     
     
         40 . A method of making an additive composition, the method comprising:
 (1) combining first one or more glycerol-restricted vegetable oil fatty acids with a polyamine to form a first reaction mixture, wherein the first one or more glycerol-restricted vegetable oil fatty acids comprise 0-0.1 percent by weight of glycerol with respect to the weight of the first one or more glycerol-restricted vegetable oil fatty acids;   (2) optionally adding a hydrocarbon solvent to the first reaction mixture;   (3) heating the first reaction mixture at a reaction temperature of between 150° C. and 200° C. for a time period between 30 minutes and 20 hours to form water and a first reaction product, the first reaction product comprising a plurality of amides.   
     
     
         41 - 47 . (canceled) 
     
     
         48 . The method of  claim 40 , further comprising:
 (4) combining second one or more glycerol-restricted vegetable oil fatty acids with one or more tertiary amines to form a second reaction mixture,   wherein the second one or more glycerol-restricted vegetable oil fatty acids comprises 0 percent to 0.1 weight percent of glycerol with respect to the weight of the second one or more glycerol-restricted vegetable oil fatty acids, and   wherein each of the one or more tertiary amines comprises at least one hydroxyl group; and   (5) heating the second reaction mixture at a reaction temperature of between 150° C. and 300° C. for a time period between 30 minutes and 10 hours to form water and a second reaction product, the second reaction product comprising a plurality of esters; and   (6) combining ingredients comprising the first reaction product and the second reaction product to form the additive composition.   
     
     
         49 - 53 . (canceled)