Phenoxypyrazole Composition and Process for the Solvent Extraction of Metals

Abstract

Metal extractants of 2-hydroxyphenyldiazole compounds according to Formula (2): and tautomers and salts thereof, are disclosed, wherein substituents R 5 , R 7 , R 9 , and R 10 are as defined herein.

What is claimed is: 
     
         1 . A metal extractant comprising a 2-hydroxyphenyldiazole compound according to Formula (2) 
       
         
           
           
               
               
           
         
       
       wherein
 R 5  is chosen from a member selected from the group consisting of hydrogen, an optionally substituted C 1 -C 36  hydrocarbyl group, halogen, and nitro; 
 R 7  is chosen from hydrogen or an optionally substituted C 1 -C 36  hydrocarbyl group; 
 each of R 9  and R 10  is independently chosen from a member selected from the group consisting of hydrogen, an optionally substituted C 1 -C 36  hydrocarbyl group, an optionally substituted C 1 -C 36  hydrocarbyloxy group, an optionally substituted C 1 -C 36  hydrocarbyloxycarbonyl group, an optionally substituted C 1 -C 36  hydrocarbylcarbonyloxy group, and an optionally substituted C 1 -C 36  mono- or dihydrocarbylaminocarbonyl group; 
 
       and tautomers or salts thereof, with the proviso that:
 when R 7  is H or C 1 -C 5 , then at least one of R 9  or R 10  is chosen from a member selected from the group consisting of an optionally substituted C 9 -C 36  hydrocarbyl, C 1 -C 36  alkoxy, C 1 -C 36  hydrocarbyloxycarbonyl, C 1 -C 36  hydrocarbylcarbonyloxy, or C 1 -C 36  mono- or dihydrocarbylaminocarbonyl. 
 
     
     
         2 . The metal extractant compound of  claim 1 , wherein each optionally substituted hydrocarbyl group is independently chosen from a member selected from the group consisting of alkyl, alkenyl, aryl, alkaryl and aralkyl group. 
     
     
         3 . The metal extractant compound of  claim 2 , wherein each optionally substituted hydrocarbyl group is independently chosen from a branched or linear alkyl group. 
     
     
         4 . The metal extractant compound of  claim 3 , wherein the alkyl group includes up to 23 carbon atoms. 
     
     
         5 . The metal extractant compound of  claim 4 , wherein the alkyl group includes up to 12 carbon atoms. 
     
     
         6 . The metal extractant compound of  claim 3 , wherein at least one of R 5 , R 7 , R 9 , and R 10  is chosen from a branched alkyl group having from 1 to 5 branches in the carbon chain. 
     
     
         7 . The metal extractant compound of  claim 2 , wherein the alkyl group is cyclic and includes from 3 to 10 carbon atoms. 
     
     
         8 . The metal extractant compound of  claim 2 , wherein the alkyl group is chosen from a member selected from the group consisting of methyl, ethyl, propyl, butyl, nonyl, hexylnonyl, butylnonyl, dodecyl, pentadecyl, heptadecyl, cyclohexyl, and isomers thereof. 
     
     
         9 . The metal extractant compound of  claim 2 , wherein at least one optionally substituted hydrocarbyl is independently chosen from a C 2-20  alkenyl group. 
     
     
         10 . The metal extractant compound according to Formula (2) of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         11 . The metal extractant compound according to  claim 1 , wherein R 7  is H, and at least one of R 9  or R 10  is a C 9 -C 36  hydrocarbyl. 
     
     
         12 . The metal extractant compound according to  claim 11 , wherein at least one of R 9  or R 10  is a C 9 -C 17  alkyl. 
     
     
         13 . The metal extractant compound according to  claim 1 , wherein at least one of R 9  or R 10  is H, and R 7  is a C 9 -C 36  hydrocarbyl. 
     
     
         14 . The metal extractant compound according to  claim 13 , wherein R 7  is a C 9 -C 17  alkyl. 
     
     
         15 . The metal extractant compound according to  claim 1 , wherein R 5  and R 9  are H; R 7  is a C 9 -C 36  hydrocarbyl; and R 10  is a C 1 -C 36  hydrocarbyl. 
     
     
         16 . The metal extractant compound according to  claim 15 , wherein each of R 7  and R 10  is independently chosen from a C 9 -C 17  hydrocarbyl group. 
     
     
         17 . The metal extractant compound according to  claim 16 , wherein each of R 7  and R 10  is nonyl. 
     
     
         18 . The metal extractant compound according to  claim 1 , wherein each of R 5 , R 7 , and R 9  is H; and R 10  is an optionally substituted C 9 -C 36  hydrocarbyl. 
     
     
         19 . The metal extractant compound according to  claim 18 , wherein R 10  is an optionally substituted C 9 -C 17  hydrocarbyl. 
     
     
         20 . The metal extractant compound according to  claim 19 , wherein R 10  is chosen from a member selected from the group consisting of hexylnonyl, pentadecyl, and heptadecyl. 
     
     
         21 . The metal extractant compound according to  claim 1 , wherein the metal extractant compound is chosen from: 4-nonyl-2-(5-nonyl-1H-pyrazol-3-yl)-phenol; 2-{5-[4,6,6-trimethyl-1-(1,3,3-trimethylbutyl)heptyl]pyrazol-3-yl}phenol; 2-(5-nonyl-1H-pyrazol-3-yl)-phenol; and 2-(5-(1-hexylnonyl)-1H-pyrazol-3-yl)-phenol. 
     
     
         22 . A solvent extraction composition comprising a water-immiscible organic solvent; and a metal extractant compound as defined by  claim 1 . 
     
     
         23 . The solvent extraction composition according to  claim 22 , wherein the metal extractant compound is present in an amount of from 1% to 60%, from 5% to 40%, or from 7.5% to 20% by weight of the total composition. 
     
     
         24 . The solvent extraction composition according to  claim 23 , wherein the metal extractant compound is present at 10% by weight of the total composition. 
     
     
         24 . The solvent extraction composition according to  claim 22  further comprising a modifier or kinetic booster compound comprising:
 a first compound chosen from a member selected from the group consisting of alcohol; ester; ether; polyether; carbonate; ketone; nitrile; amide; carbamate; sulphoxide; acids of sulphur or phosphorous compounds; and salts of amines and quaternary ammonium compounds; and 
 a second compound chosen from a member selected from the group consisting of alkanols, alkyl esters, and tributylphosphate. 
 
     
     
         25 . The solvent extraction composition according to  claim 24 , wherein the alkanol contains from 6 to 18 carbon atoms. 
     
     
         26 . The solvent extraction composition according to  claim 24 , wherein the alkyl ester contains from 7 to 30 carbon atoms. 
     
     
         27 . The solvent extraction composition according to  claim 22 , wherein the water-immiscible organic solvent possesses an aromatic content of less than 30%. 
     
     
         28 . The solvent extraction composition according to  claim 27 , wherein the aromatic content of the water-immiscible organic solvent is 23% or less.