Method and system for hydrogen evolution and storage

A method for producing hydrogen, comprising exposing at least one chemical compound to a catalyst under conditions suitable for chemical reaction that forms hydrogen,

• the chemical compound having the formula
• wherein Q is —(C(R7R8))n— where n is from 1 to 10, —(C(R7R8)-M-C(R7R8))—, —(C(R7)═C(R8))—, —(C(R7)═C(R8)—C(R9)═C(R10))—, —(C(R7)═N)—, or —(C(R7)═N—C(R8)═N)—;
• wherein M is oxygen, —NR9—, sulfur, or —C(═O)—;
• wherein Z is oxygen, sulfur, or —N(R11)—;
• wherein R5 and R11 are independently selected from hydrogen, alkyl, and aryl;
• wherein R7, R8, R9, and R10 are independently selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, and alkenyl phosphonic acid;
• wherein R6 is selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid, —OR12, —N(H)(R12) and —N(R12R13) wherein R12 and R13 are independently selected from hydrogen, alkyl and aryl;
• wherein R7 and R8 may be connected to each other to form a ring structure;
• wherein R8 and R9 may be connected to each other to form a ring structure;
• and
• with the proviso that at least one of R5 or R11 is hydrogen.

A method for producing hydrogen, comprising exposing at least one chemical compound and an acid to a catalyst under conditions suitable for chemical reaction that forms hydrogen,

• the chemical compound having the formula
• wherein Q is —(C(R7R8))n— where n is from 1 to 10, —(C(R7R8)-M-C(R7R8))—, —(C(R7)═C(R8))—, —(C(R7)═C(R8)—C(R9)═C(R10))—, —(C(R7)═N)—, or —(C(R7)═N—C(R8)═N)—;
• wherein M is oxygen, —NR9—, sulfur, or —C(═O)—;
• wherein Z is oxygen, sulfur, or —N(R11)—;
• wherein R5 and R11, are independently selected from hydrogen, alkyl, and aryl;
• wherein R7, R8, R9, and R10 are independently selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, and alkenyl phosphonic acid;
• wherein R6 is selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid, -OR12, —N(H)(R12) and —N(R12R13) wherein R12 and R13 are independently selected from hydrogen, alkyl and aryl;
• wherein R7 and R8 may be connected to each other to form a ring structure;
• and wherein R8 and R9 may be connected to each other to form a ring structure;
• the acid comprising an alcohol, a phenol, or a compound having the formula HX or the formula HTX, wherein X is selected from chloride, bromide, iodide, carboxylate, sulfonate, phosphate, phosphonate, sulfate, and hydroxide;
• and
• wherein T is selected from imidazole, alkylimidazole, arylimidazole, benzimidazole, alkylbenzimidazole, oxazole, alkyloxazole, benzoxazole, pyrazole, alkylpyrazole, arylpyrazole, pyridine, alkylpyridine, arylpyridine, quinoline, ammonia, and amine.

A system for producing hydrogen, comprising at least one organic compound, an acid, and a catalyst suitable for facilitating a chemical reaction between the at least one chemical compound and the acid in order to form hydrogen,

• the chemical compound having the formula
• wherein Q is —(C(R7R8))n— where n is from 1 to 10, —(C(R7R8)-M-C(R7R8))—, —(C(R7)═C(R8))—, —(C(R7)═C(R8)—C(R9)═C(R10))—, —(C(R7)═N)—, or —(C(R7)═N—C(R8)═N)—;
• wherein M is oxygen, —NR9—, sulfur, or —C(═O)—;
• wherein Z is oxygen, sulfur, or —N(R11)—;
• wherein R5 and R11 are independently selected from hydrogen, alkyl, and aryl;
• wherein R7, R8, R9, and R10 are independently selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, and alkenyl phosphonic acid;
• wherein R6 is selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid —OR12, —N(H)(R12) and —N(R12R13) wherein R12 and R13 are independently selected from hydrogen, alkyl and aryl;
• wherein R7 and R8 may be connected to each other to form a ring structure;
• and
• wherein R8 and R9 may be connected to each other to form a ring structure;
• the acid comprising an alcohol, a phenol, or a compound having the formula HX or the formula HTX, wherein X is selected from chloride, bromide, iodide, carboxylate, sulfonate, phosphate, phosphonate, sulfate, and hydroxide;
• and wherein T is selected from imidazole, alkylimidazole, arylimidazole, benzimidazole, alkylbenzimidazole, oxazole, alkyloxazole, benzoxazole, pyrazole, alkylpyrazole, arylpyridine, arylpyrazole, pyridine, alkylpyridine, quinoline, ammonia, and amine.

A system for producing hydrogen, comprising at least one chemical compound having the formula

• wherein Q is —(C(R7R8))n— where n is from 1 to 10, —(C(R7R8)-M-C(R7R8))—, —(C(R7)═C(R8))—, —(C(R7)═C(R8)—C(R9)═C(R10))—, —(C(R7)═N)—, —(C(R7)═N—C(R8)═N)—;
• wherein M is oxygen, —NR9—, sulfur, or —C(═O)—;
• wherein Z is oxygen, sulfur, or —N(R11)— wherein R11 is hydrogen, alkyl, or aryl;
• wherein R7, R8, R9, and R10 are independently selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, and alkenyl phosphonic acid;
• wherein R6 is selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid, —OR12, —N(H)(R12) and —N(R12R13) wherein R12 and R13 are independently selected from hydrogen, alkyl and aryl;
• wherein R7 and R8 may be connected to each other to form a ring structure;
• and
• wherein R8 and R9 may be connected to each other to form a ring structure.

A system for producing hydrogen, comprising at least one chemical compound having the formula

• wherein Z is selected from oxygen, sulfur, or —N(R4)— where R4 is alkyl or aryl;
• wherein Q is selected from oxygen, —N(R5)—, —(C(R5R6))n— where n is from 1 to 10, —(C(R5)═C(R6))m— where m is from 1 to 2, and —(C(R5)═N)p— where p is from 1 to 2;
• wherein R1, R2, R4, R5, and R6 are selected independently from alkyl, aryl;
• and
• wherein R3 is selected from hydrogen, alkyl, aryl;
• and a catalyst suitable for facilitating the dehydrogenation of said chemical compound.

A fuel cell comprising an anode and a hydrogen-generating fuel source for the anode, said hydrogen-generating fuel source comprising at least one chemical compound and a catalyst suitable for dehydrogenating the at least one chemical compound, the at least one chemical compound having the formula

• wherein X is oxygen, —N(H)—, or —N(R3)—;
• wherein X′ is oxygen, —N(H)— or —N(R4)—;
• wherein R1, R2, R3, and R4 are independently selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl sulfonic acid, alkenyl phosphoric acid, and alkenyl phosphonic acid;
• and wherein R1 and R3 can be connected to each other to form a ring structure.

A fuel cell comprising an anode and a hydrogen-generating fuel source for the anode, said hydrogen generating fuel source comprising at least one chemical compound having the formula

• wherein Q is —(C(R7R8))n— where n is from 1 to 10, —(C(R7R8)-M-C(R7R8))—, —(C(R7)═C(R8))—, —(C(R7)═C(R8)—C(R9)═C(R10))—, —(C(R7)═N)—, or —(C(R7)═N—C(R8)═N)—;
• wherein M is oxygen, —NR9—, sulfur, or —C(═O)—;
• wherein Z is oxygen, sulfur, or —N(R11)—;
• wherein R5 and R11 are independently selected from hydrogen, alkyl, and aryl;
• wherein R7, R8, R9, and R10 are independently selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid;
• wherein R6 is selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid, —OR12, —N(H)(R12) and —N(R12R13) wherein R12 and R13 are selected from hydrogen, alkyl and aryl;
• wherein R7 and R8 may be connected to each other to form a ring structure;
• wherein R8 and R9 may be connected to each other to form a ring structure;
• and
• with the proviso that at least one of R5or R11 is hydrogen.

A fuel cell comprising an anode and a hydrogen-generating fuel source for the anode, said hydrogen generating fuel source comprising at least one chemical compound having the formula

• wherein Q is —(C(R7R8))n— where n is from 1 to 10, —(C(R7R8)-M-C(R7R8))—, —(C(R7)═C(R8))—, —(C(R7)═C(R8)—C(R9)═C(R10))—, —(C(R7)═N)—, —(C(R7)═N—C(R8)═N)—;
• wherein M is oxygen, —NR9—, sulfur, or —C(═O)—;
• wherein Z is oxygen, sulfur, or —N(R11)— wherein R11 is hydrogen, alkyl, or aryl;
• wherein R7, R8, R9, and R10 are independently selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid;
• wherein R6 is selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid, —OR12, —N(H)(R12) and —N(R12R13) wherein R12 and R13 are selected from hydrogen, alkyl and aryl;
• wherein R7 and R8 may be connected to each other to form a ring structure;
• and
• wherein R8 and R9 may be connected to each other to form a ring structure.

A fuel cell comprising an anode and a hydrogen-generating fuel source for the anode, said hydrogen generating fuel source comprising at least one chemical compound having the formula

• wherein Z is selected from oxygen, sulfur, or —N(R4)— where R4 is alkyl or aryl;
• wherein Q is selected from oxygen, —N(R5)—, —(C(R5R6))n— where n is from 1 to 10, —(C(R5)═C(R6))m— where m is from 1 to 2, and —(C(R5)═N)p— where p is from 1 to 2;
• wherein R1, R2, R4, R5, and R6 are selected independently from alkyl, aryl;
• and wherein R3 is selected from hydrogen, alkyl, aryl.

A method for storing hydrogen, comprising exposing at least one chemical compound to hydrogen in the presence of a catalyst that facilitates the hydrogenation of the at least one chemical compound, the chemical compound comprising an anion and cationic portion having the formula

• wherein Q is —(C(R7R8))n— where n is from 1 to 10, —(C(R7R8)-M-C(R7R8))—, —(C(R7)═C(R8))—, —(C(R7)═C(R8)—C(R9)═C(R10))—, —(C(R7)═N)—, or —(C(R7)═N—C(R8)═N)—;
• wherein M is oxygen, —NR9—, sulfur, or —C(═O)—;
• wherein Z is oxygen, sulfur, or —N(R11)—;
• wherein R5 and R11 are independently selected from hydrogen, alkyl, and aryl;
• wherein R7, R8, R9, and R10 are independently selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid;
• wherein R6 is selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid, —OR12, —N(H)(R12) and —N(R12R13) wherein R12 and R13 are selected from hydrogen, alkyl and aryl;
• wherein R7 and R8 may be connected to each other to form a ring structure;
• and wherein R8 and R9 may be connected to each other to form a ring structure.

A method for storing hydrogen, comprising exposing at least one chemical compound to a reducing agent, the chemical compound comprising an anion and a cationic portion having the formula

• wherein Q is —(C(R7R8))n— where n is from 1 to 10, —(C(R7R8)-M-C(R7R8))—, —(C(R7)═C(R8))—, —(C(R7)═C(R8)—C(R9)═C(R10))—, —(C(R7)═N)—, or —(C(R7)═N—C(R8)═N)—;
• wherein M is oxygen, —NR9—, sulfur, or —C(═O)—;
• wherein Z is oxygen, sulfur, or —N(R11)—;
• wherein R5 and R11 are independently selected from hydrogen, alkyl, and aryl;
• wherein R7, R8, R9, and R10 are independently selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid;
• wherein R6 is selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl phosphoric acid, alkenyl phosphonic acid, —OR12, —N(H)(R12) and —N(R12R13) wherein R12 and R13 are selected from hydrogen, alkyl and aryl;
• wherein R7 and R8 may be connected to each other to form a ring structure;
• and
• wherein R8 and R9 may be connected to each other to form a ring structure.

A method for storing hydrogen, comprising exposing at least one chemical compound to hydrogen or to a reducing agent in the presence of a catalyst that facilitates the hydrogenation of the at least one chemical compound, the chemical compound having the formula

• wherein X is oxygen, —N(H)—, or —N(R3)—;
• wherein X′ is oxygen, —N(H)— or —N(R4)—;
• wherein R1, R2, R3, and R4 are independently selected from hydrogen, alkyl, aryl, alkenyl, alkyl carboxylic acid, alkyl sulfonic acid, alkyl phosphoric acid, alkyl phosphonic acid, aryl carboxylic acid, aryl sulfonic acid, aryl phosphoric acid, aryl phosphonic acid, alkenyl carboxylic acid, alkenyl sulfonic acid, alkenyl phosphoric acid, and alkenyl phosphonic acid;
• and wherein R1 and R3 can be connected to each other to form a ring structure;
• and
• with the proviso that X and X′ cannot both be oxygen.