Low interfacial tension surfactants for petroleum applications

Abstract

The invention relates to a class of novel surfactants that have utility in the recovery and/or extraction of oil.

1 . A compound having the Formula (I): 
       
         
           
           
               
               
           
         
         wherein A is an alkyl, alkenyl, alkadienyl, alkynyl, cycloalkyl, or cycloalkenyl, each optionally substituted; 
         p is 1 or 2; 
         each m and n are independently 0, 1, 2, 3, 4, or 5; 
         each of G 1  and G 2  are independently absent, O, S, NR 2 , C(O)O, OC(O), C(O), C(O)NR 2 , or NR 2 C(O), wherein at least one of G 1  and G 2  is present; 
         each R 2  is independently H or a lower alkyl; 
         G 3  is absent, (CH 2 ) q  or G 1 ; 
         each q is independently 1, 2, 3, 4 or 5; 
         R is a hydrophilic group; and 
         R 1  is a saturated or unsaturated hydrophobic aliphatic group. 
       
     
     
         2 . The compound of  claim 1 , wherein G 1  is selected from the group consisting of O, S, NR 2 , C(O)O, OC(O), C(O), C(O)NR 2 , and NR 2 C(O). 
     
     
         3 . The compound of  claim 1 , wherein A is an alkyl or cycloalkyl, each optionally substituted. 
     
     
         4 - 9 . (canceled) 
     
     
         10 . The compound of  claim 1 , wherein G 1  is selected from the group consisting of OC(O), C(O)O, C(O), C(O)NR 2  and NR 2 CO. 
     
     
         11 . (canceled) 
     
     
         12 . The compound of  claim 1 , wherein R is C(O)OH. 
     
     
         13 . The compound of  claim 1 , wherein R 1  is selected from the group consisting of C 5 -C 20  alkyl, C 5 -C 20  alkenyl, and C 5 -C 20  alkadienyl. 
     
     
         14 . The compound of  claim 1  having the Formula (Ia): 
       
         
           
           
               
               
           
         
         wherein t is 0 or 1; and 
         G 4  is O or NH. 
       
     
     
         15 . A compound of Formula (II): 
       
         
           
           
               
               
           
         
         wherein D is an aliphatic polymer; 
         p is 1 or 2; 
         each m and n are independently 0, 1, 2, 3, 4, or 5; 
         each of G 1  and G 2  are independently absent, O, S, NR 2 , C(O)O, OC(O), CO, C(O)NR 2 , or NR 2 C(O); 
         each R 2  is independently H or a lower alkyl; 
         G 3  is independently absent, (CH 2 ) q  or G 1 ; 
         each q is 1, 2, 3, 4 or 5; 
         R is a hydrophilic group; and 
         R 1  is a saturated or unsaturated hydrophobic aliphatic group. 
       
     
     
         16 . The compound of  claim 15 , wherein D is selected from the group consisting of polyethylene glycol, polypropylene glycol, polyethylene glycol methyl ether, polyetheramine and ethylene oxide/propylene oxide block copolymer. 
     
     
         17 . The compound of  claim 15 , wherein p is 1. 
     
     
         18 . The compound of  claim 15 , wherein p is 2. 
     
     
         19 . The compound of  claim 15 , wherein each G 1  is independently selected from the group consisting of OC(O), C(O)O, C(O), C(O)NR 2  and NR 2 C(O). 
     
     
         20 . The compound of  claim 15 , wherein G 2  is absent. 
     
     
         21 . The compound of  claim 15 , wherein R is C(O)OH. 
     
     
         22 . The compound of  claim 15 , wherein R 1  is selected from the group consisting of C 5 -C 20  alkyl, C 5 -C 20  alkenyl, and C 5 -C 20  alkadienyl. 
     
     
         23 . The compound of  claim 15 , having the Formula (IIa): 
       
         
           
           
               
               
           
         
         wherein t is 0 or 1; and 
         G 4  is O or NH. 
       
     
     
         24 . A compound of Formula III:
   EG 5 -D 2 ) p ;
   wherein E is alkyl, alkenyl, alkadienyl, alkynyl, cycloalkyl, cycloalkenyl, aryl and heteroaryl;   G 5  is C(O)NH;   D 2  is a hydrophilic aliphatic polymer; and   p is 1 or 2.   
     
     
         25 - 27 . (canceled) 
     
     
         28 . A compound having the Formula IV:
   D 2 -N(J) 2 ;   wherein D 2  is a hydrophilic aliphatic polymer;   wherein each J is independently selected from the group consisting of H and the Fragment (A):   
       
         
           
           
               
               
           
         
         wherein E is a hydrophobic group selected from the group consisting of alkyl, alkenyl, alkadienyl, alkynyl, cycloalkyl, cycloalkenyl, aryl and heteroaryl; 
         and wherein at least one J is the Fragment (A). 
       
     
     
         29 . (canceled) 
     
     
         30 . (canceled) 
     
     
         31 . A compound having the Formula V:
   (J) 2 N-D2-N(J) 2 ;   wherein D 2  is a hydrophilic aliphatic polymer;   each J is independently selected from the group consisting of H and the Fragment (A):   
       
         
           
           
               
               
           
         
         wherein E is a hydrophobic group selected from the group consisting of alkyl, alkenyl, alkadienyl, alkynyl, cycloalkyl, cycloalkenyl, aryl and heteroaryl; 
         and wherein at least two of J are Fragment (A). 
       
     
     
         32 . (canceled) 
     
     
         33 . (canceled) 
     
     
         34 . A method for extracting oil from an oil mixture comprising:
 (a) adding a compound of  claim 1 , to an oil mixture, and   (b) collecting the oil.   
     
     
         35 . A method for extracting oil from an oil mixture comprising:
 (a) adding a compound of  claim 15 , to an oil mixture, and   (b) collecting the oil.