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 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 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 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, and C 1 -C 36  mono- or dihydrocarbylaminocarbonyl. 
 
     
     
         2 . The metal extractant compound of  claim 1 , wherein each optionally substituted hydrocarbyl group is independently 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 selected from the group consisting of methyl, ethyl, propyl, butyl, nonyl, hexylnonyl, butylnonyl, dodecyl, pentadecyl, heptadecyl, and cyclohexyl. 
     
     
         8 . 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. 
     
     
         9 . The metal extractant compound according to  claim 8 , wherein at least one of R 9  or R 10  is a C 9 -C 17  alkyl. 
     
     
         10 . 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. 
     
     
         11 . The metal extractant compound according to  claim 10 , wherein R 10  is an optionally substituted C 9 -C 17  hydrocarbyl. 
     
     
         12 . The metal extractant compound according to  claim 11 , wherein R 10  is chosen from a member selected from the group consisting of hexylnonyl, pentadecyl, and heptadecyl. 
     
     
         13 . The metal extractant compound according to  claim 1 , wherein the metal extractant compound is selected from the group consisting of 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. 
     
     
         14 . A solvent extraction composition comprising a water-immiscible organic solvent; and a metal extractant compound as defined by  claim 1 . 
     
     
         15 . A solvent extraction composition according to  claim 14 , 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. 
     
     
         16 . A solvent extraction composition according to  claim 15 , wherein the metal extractant compound is present at 10% by weight of the total composition. 
     
     
         17 . A solvent extraction composition according to  claim 14 , wherein at least one of R 9  or R 10  of the metal extractant compound is a C 9 -C 36  hydrocarbyl. 
     
     
         18 . A solvent extraction composition according to  claim 17 , wherein at least one of R 9  or R 10  is a C 9 -C 17  alkyl. 
     
     
         19 . A solvent extraction composition according to  claim 14 , wherein the metal extractant compound is selected from the group consisting of 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. 
     
     
         20 . A solvent extraction composition according to  claim 19 , wherein the metal extractant compound is 2-{5-[4,6,6-trimethyl-1-(1,3,3-trimethylbutyl)heptyl]pyrazol-3-yl}phenol.