Method for producing polyolefinic amines and compositions containing same

Abstract

Polyolefinic amines may be produced in a reaction comprising contacting an olefin or a polyolefin with an azo compound under free radical conditions to form a polyolefinic nitrile having an average molecular weight of at least 250, followed by reducing the polyolefinic nitrile to a corresponding polyolefinic amine. The polyolefinic amines produced by the reaction may be included as a detergent in compositions, such as fuel compositions, additive compositions, and/or carrier compositions.

1 . A use of a composition comprising polyolefinic amines produced by (a) contacting an olefin or a polyolefin with an azo compound under free radical conditions to form a polyolefinic nitrile having an average molecular weight of at least 250; and (b) reducing said polyolefinic nitrile to a corresponding polyolefinic amine. 
     
     
         2 . A use of a composition as described in  claim 1 , wherein reducing said polyolefinic nitrile to a corresponding polyolefinic amine occurs in the presence of a hydrogenation catalyst. 
     
     
         3 . A use of a composition as described in  claim 1 , wherein said polyolefinic amine contains an average number of carbon atoms of at least about 12. 
     
     
         4 . A use of a composition as described in  claim 1 , wherein said polyolefinic amine contains greater than about 35%, by weight of total polyolefin amine molecules, polyolefin amine molecules with at least 12 carbon atoms. 
     
     
         5 . A use of a composition as described in  claim 1 , wherein said polyolefinic amine is a mixture in which the predominant polyolefin amine molecule contains at least about 12 carbon atoms per molecule. 
     
     
         6 . A use of a composition as described in  claim 1 , wherein the azo compound is selected from the group consisting of 2,2′-azobisisobutyronitrile (“AIBN”), 2,2′azobis(2-butanenitrile), 1,1′-azobis(cyclohexanecarbonitrile), 2-(tbutylazo)-2-cyanopropane, 2,2′-azobis[2-methyl-N-(1,1)bis(hydroxymethyl)-2hydroxyethyl]propionamide, 2,2′-azobis(2methyl-Nhydroxyethyl)propionamide, 2,2′-azobis(N,N′dimethyleneisobutyramidine) dichloride, 2,2′-azobis(2-amidinopropane) dichloride, 2,2′azobis(N,N′-dimethyleneisobutyramide), 2,2′-azobis(2methyl-N-[1,1-bis(hydroxymethyl)2-hydroxyethyl]propionamide), 2,2′-azobis(2-methyl-N-[1,1bis(hydroxymethyl)ethyl]propionamide), 2,2′-azobis(2-methylN-(2-hydroxyethyl)propionamide), 2,2′azobis(isobutyramide) dihydrate, azobutyronitrile, 2,2′-azobis-(4methoxy-2,4dimethylpentanenitrile), 2,2′-azobis-(2,4dimethylpentanenitrile), 2,2′azobis-(2-methylbutyronitrile), 2,2′azobis(4-methoxy-2,4dimethylvaleronitrile). 
     
     
         7 . A use of a composition as described in  claim 6 , wherein the azo compound is 2,2′-azobisisobutyronitrile. 
     
     
         8 . A use of a composition as described in  claim 1 , wherein the olefin is an one or more olefins selected from the group consisting of propene, butene, pentene, isobutene, styrene, hexene, heptene, octene, nonene, decene, undecene, dodecene, tridecene, hexadecene, tetradecene, pentadecene, heptadecene, nonadecene, octadecene, 1-octadecene, eicocene 1-eicocene, 1-doeicocene, 1-tetraeicocene, 1-hexaeicocene, 1-octaeicocene, 1-triacontene. 
     
     
         9 . A use of a composition as described in  claim 1  wherein the olefin is a mixture of olefins comprising blends of olefins selected from the group consisting of 1-octadecene/1-tetraeicocene, 1-eicocene/1-doeicocene/1-tetraeicocene, and 1-tetraeicocene/1-hexaeicocene/1-octaeicocene. 
     
     
         10 . A use of a composition as described in  claim 1 , wherein the polyolefin is one or more polyolefins selected from the group consisting of polypropene, polybutene, polypentene, polyisobutene, polystyrene, polyhexene, polyheptene, polyoctene, polynonene, polydecene, polyundecene polydodecene, polytridecene, polyhexadecene, polytetradecene, polypentadecene, polyheptadecene, polynonadecene, polyoctadecene, polyeicocene. 
     
     
         11 . A use of a composition as described in  claim 10 , wherein the polyolefin is polyisobutene. 
     
     
         12 . A use of a composition as described in  claim 1 , wherein the reaction further comprises a catalyst that facilitates the reaction between the olefin or the polyolefin and the azo compound. 
     
     
         13 . A use of a composition as described in  claim 12 , wherein said catalyst that facilitates the reaction between the olefin or the polyolefin and the azo compound is a naked cation catalyst. 
     
     
         14 . A use of a composition as described in  claim 12 , wherein said catalyst that facilitates the reaction between the olefin or the polyolefin and the azo compound is selected from the group consisting of boranes, carboranes, fullerides, metallocenes, and lithium containing catalysts. 
     
     
         15 . A use of a composition as described in  claim 14 , wherein said lithium containing catalyst is a weakly solvated lithium cation. 
     
     
         16 . A use of a composition as described in  claim 14 , wherein said lithium containing catalyst is LiCB 11 (CH 3 ) 12 . 
     
     
         17 . A use of a composition as described in  claim 1 , wherein the use is as a detergent in a composition selected from the group consisting of fuel compositions, fuel additive compositions, and concentrate compositions. 
     
     
         18 . A use of a composition as described in  claim 1 , wherein the use is to prevent the formation of engine deposits and/or to remove engine deposits already formed by combining the composition with a fuel and combusting the combination in said engine. 
     
     
         19 . A use of a composition as described in  claim 1 , wherein the use is in an engine selected from the group consisting of electrical power generation installations, pumping stations, automobile engines, truck engines, road-equipment, and military vehicles.