Back to results
US 8,574,453 B2Granted
Reversible room-temperature ionic liquids
AssigneeGeorgetown University
InventorsTao Yu, Richard G. Weiss, Taisuke Yamada, Mathew George
Life of this patent
Estimating the term…
Abstract
One aspect of the present invention relates to salts that are room-temperature ionic liquids (RTILs), methods of making them, and methods of using them in connection with temporary or permanent gas sequestration. Another aspect of the present invention relates to a class of solvents which can be transformed into RTILs by exposure to a gas, and methods of using them in connection with temporary or permanent gas sequestration.
Claims13
A salt represented by:
- wherein
- R1 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R2 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R3 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —S C(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R4 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —S C(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R5 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, —C(R8)3, or —(CH2)n—NH2;
- R6 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —S C(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, —C(R8)3, or —(CH2)n—NH2;
- Y represents independently for each occurrence O or S;
- R8 represents independently for each occurrence —(CH2)n—CH3, cycloalkyl, aryl, or heteroaryl;
- and
- n represents independently for each occurrence an integer in the range 1-10 inclusive.
8 more elements
A method of preparing a salt, comprising the step of contacting a gas with a first compound and a second compound, wherein said first compound is
- wherein
- R1 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R2 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R3 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R4 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R8 represents independently for each occurrence —(CH2)n—CH3, cycloalkyl, aryl, or heteroaryl;
- and
- n represents independently for each occurrence an integer in the range 1-10 inclusive;
- and
- said second compound is represented by
- wherein
- R5 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —CH(R8)2, —C(R8)3, or —(CH2)n—NH2;
- R6 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —CH(R8)2, —C(R8)3, or —(CH2)n—NH2;
- R8 represents independently for each occurrence —(CH2)n—CH3, cycloalkyl, aryl, or heteroaryl;
- and
- said gas is represented by:
- Y═X═Y
- wherein
- X represents C or N;
- and
- Y represents independently for each occurrence O or S.
18 more elements
A method comprising the step of contacting a first gas with an ionic liquid, thereby generating a second gas;
- wherein said ionic liquid is represented by:
- wherein
- said first gas is an inert gas;
- said second gas is CO2 or CS2;
- R1 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —S C(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R2 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R3 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R4 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, or —C(R8)3;
- R5 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —C≡CR8, —CH(R8)2, —C(R8)3, or —(CH2)n—NH2;
- R6 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —CH(R8)2, —C(R8)3, or —(CH2)n—NH2;
- Y represents independently for each occurrence O or S;
- R8 represents independently for each occurrence —(CH2)n—CH3, cycloalkyl, aryl, or heteroaryl;
- and
- n represents independently for each occurrence an integer in the range 1-10 inclusive.
11 more elements
A method of removing a gas from a mixture, comprising the step of contacting said mixture with a first compound and a second compound, wherein said first compound is
- wherein
- R1 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —CH(R8)2, or —C(R8)3;
- R2 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —CH(R8)2, or —C(R8)3;
- R3 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —CH(R8)2, or —C(R8)3;
- R4 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —SC(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —CH(R8)2, or —C(R8)3;
- R8 represents independently for each occurrence —(CH2)n—CH3, cycloalkyl, aryl, or heteroaryl;
- and
- n represents independently for each occurrence an integer in the range 1-10 inclusive;
- said second compound is represented by
- wherein
- R5 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —S C(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —CH(R8)2, —C(R8)3, or —(CH2)n—NH2;
- R6 represents H, halogen, alkyl, fluoroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, —(CH2)n—R8, —OR8, —N(R8)2, —SR8, —C(═O)OR8, —OC(═O)R8, —NR8C(═O)R8, —C(═O)N(R8)2, —C(═O)SR8, —S C(═O)R8, —S(═O)R8, —S(═O)2R8, —S(═O)2OR8, —C(═O)R8, —C(═NR8)R8, —C(═S)R8, —C(R8)═C(R8)2, —CH(R8)2, —C(R8)3, or —(CH2)n—NH2;
- R8 represents independently for each occurrence cycloalkyl, aryl, or heteroaryl;
- n represents independently for each occurrence an integer in the range 1-10 inclusive;
- and
- said gas is represented by:
- Y═X═Y
- wherein
- X represents C or N;
- and
- Y represents independently for each occurrence O or S.
18 more elements
Dependencies are inferred from the claim text.