Hindered cyclic polyamines and their salts for acid gas scrubbing process

• US 20090297414A1
• Filed: 07/21/2006
• Published: 12/03/2009
• Est. Priority Date: 08/09/2005
• Status: Active Grant

• Current Assignee: Alan R. Katritzky, Edmund John Mozeleski, Frank Chen-Yu Wang, Michael Siskin
• Original Assignee: Alan R. Katritzky, Edmund John Mozeleski, Frank Chen-Yu Wang, Michael Siskin
• Inventors: Siskin, Michael, Chen-Yu, Wang Frank, Mozeleski, Edmund John, Katritzky, Alan R.
• Granted Patent: US 8,152,903 B2
• Time in Patent Office: Days
• US Class Current: 423/228
• CPC Class Codes: A61K 31/445 Non condensed piperidines, e.g. piperocaine
• CPC Class Codes: A61K 31/55 having seven-membered rings, e.g. azelastine, pentylenetetrazole
• CPC Class Codes: B01D 53/1468 Removing hydrogen sulfide
• CPC Class Codes: B01D 53/1493 Selection of liquid materials for use as absorbents
• CPC Class Codes: C07D 215/06 having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
• CPC Class Codes: C07D 401/02 containing two hetero rings
• CPC Class Codes: C07D 401/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 487/08 Bridged systems

Abstract

Hindered cyclic polyamines and their salts are absorbents useful in acid gas treatment processes.

Claims

1. A process for the selective removal of one or more acidic components from normally gaseous mixtures containing such acidic components and CO₂ comprising contacting the normally gaseous mixture with an amino-containing absorbent comprising one or more material of the formula:

and all isomers thereof,

and all isomers thereof,

and isomers thereof,

wherein R¹ and R² are the same or different and are selected from hydrogen methyl, ethyl, C₃-C₉ substituted or unsubstituted straight or branched alkyl, alkenyl, cycloalkyl, C₆-C₉ aryl, alkylaryl, arylalkyl;

X¹-X⁸ are the same or different and are selected from hydrogen, methyl, ethyl,

C₃-C₉ substituted or unsubstituted straight or branched alkyl, alkenyl, cycloalkyl,

C₆-C₉ aryl, alkylaryl, arylalkyl, a functional group containing one or more oxygens, X⁹ and X¹⁰ are the same or different and are selected from —

(HO₃SR⁴)⁺, —

(HO₃PR⁴)⁺,

sulfonates, sulfates, sulfites, phosphates, phosphites, phosphonates, C₁-C₉ alkylates, adipates, benzoates,

X¹¹ and X¹² are the same or different and are selected from hydrogen, a functional group containing one or more oxygens, wherein

when R¹ and/or R² are C₂ or greater the substituent X¹¹ or X², when other than H, is an the #2 carbon or higher,

y is zero or 1,

z is zero or 1,

wherein when X¹-X⁸ and X¹¹ and X¹² are not functional groups containing at least one oxygen at least one of Y and Z is 1,

provided that when any of X¹-X⁸, X¹¹ or X¹² is a functional group containing a single oxygen at least 2 of X¹ to X⁸, X¹¹ or X¹² are such single oxygen containing functional group, and R⁴ is selected from C₁-C₉ allyl, C₂-C₉ alkenyl, C₃-C₉ cycloalkyl, C₆-C₉ aryl, alkylaryl or arylalkyl, under conditions suitable for the selective removal of one or more of the gaseous acidic components from said mixture.

2. The process of claim 1 wherein the absorbent comprises one or more materials of the formula:

3. The process of claim 1 wherein the absorbent comprises one or more materials of the formula

and all isomers thereof.

4. The process of claim 1 wherein the absorbent comprises one or more materials of the formula:

and all isomers thereof.

5. The process of claim 1 wherein the absorbent comprises one or more materials of the formula:

and all isomers thereof.

6. The process of claim 1 wherein the absorbent comprises one or more materials of the formula:

7. The process of claim 1, 2, 3, 4, 5 or 6 wherein when one or more of X¹-X⁸, X¹¹ and X¹² are functional groups containing at least one oxygen, Y and Z are both zero.

8. The process of claim 1, 2, 3, 4, 5 or 6 wherein X¹-X² are selected from the group consisting of:

and mixtures thereof,

wherein R³ is selected from C₁-C₉ alkyl, C₂-C₉ alkenyl, C₃-C₉ cycloalkyl, C₆-C₉ aryl, alkylaryl or arylalkyl, and metal cation is one or more monovalent, divalent or trivalent metal cation sufficient to satisfy the valence requirement of the anion or anion cluster.

9. An absorbent for the selective removal of acidic components from normally gaseous mixture containing such acidic components and non-acidic components and CO₂, said absorbent being of the formula:

and all isomers thereof,

and all isomers thereof.

and all isomers thereof.

wherein R¹ and R² are the same or different and are selected from hydrogen methyl, ethyl, C₃-C₉ substituted or unsubstituted straight or branched alkyl, alkenyl, cycloalkyl, C₆-C₉ aryl, alkylaryl, arylalkyl;

X¹-X⁸ are the same or different and are selected from hydrogen, methyl, ethyl,

C₃-C₉ substituted or unsubstituted straight or branched alkyl, alkenyl, cycloalkyl,

C₆-C₉ alkyl, alkyl aryl, arylalkyl, a functional group containing one or more oxygens, X⁹ and X¹⁰ are the same or different and are selected from —

(HO₃SR⁴)⁺,

—

(HO₃PR⁴)⁺,

sulfonates, sulfates, sulfites, phosphates, phosphites, phosphonates, C₁-C₉ alkylates, adipates, benzoates,

X¹¹ and X¹² are the same or different and are selected from hydrogen, a functional group containing one or more oxygens, wherein

when R¹ and/or R² are C₂ or greater the substituent X¹¹ or X², when other than H, is an the #2 carbon or higher,

y is zero or 1,

z is zero or 1,

wherein when X¹-X⁸ and X¹¹ and X¹² are not functional groups containing at least one oxygen at least one of Y and Z is 1,

provided that when any of X¹-X⁸, X¹¹ or X¹² is a functional group containing a single oxygen at least 2 of X¹ to X⁸, X¹¹ or X¹² are such single oxygen containing functional group, and R⁴ is selected from C₁-C₉ alkyl, C₂-C₉ alkenyl, C₃-C₉ cycloalkyl, C₆-C₉ aryl, alkylaryl or arylalkyl, under conditions suitable for the selective removal of one or more of the gaseous acidic components from said mixture.

10. The absorbent of claim 9 of the formula:

11. The absorbent of claim 9 of the formula:

and all isomers thereof.

12. The absorbent of claim 9 of the formula:

and all isomers thereof.

13. The absorbent of claim 9 of the formula:

and all isomers thereof.

14. The absorbent of claim 9 of the formula:

15. The absorbent of claim 9, 10, 11, 12, 13 or 14 wherein when one or more of X¹-X⁸, X¹¹ and X¹² are functional groups containing at least one oxygen, Y and Z are both zero.

16. The absorbent of claim 9, 10, 11, 12, 13 or 14 wherein X¹-X² are selected from the group consisting of:

and mixtures thereof,

wherein R³ is selected from C₁-C₉ alkyl, C₂-C₉ alkenyl, C₃-C₉ cycloalkyl, C₆-C₉ aryl, alkylaryl or aryl alkyl, and metal cation is one or more monovalent, divalent or trivalent metal cation to satisfy the valence requirement of the anion or anion cluster.