Pure- and mixed-gas CO2/CH4 separation properties of PIM-1 and an amidoxime-functionalized PIM-1

Journal of Membrane Science

Volumn 457, Issue , 2014, Pages 95-102

  Swaidan, Raja ^a   Ghanem, Bader S ^a   Litwiller, Eric ^a   Pinnau, Ingo ^a  

^a KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

Author keywords

Amidoxime; CO2 CH4 mixed gas permeation; Functionalized PIMs; Gas separation; Intrinsic microporosity

Indexed keywords

EID: 84894104248     PISSN: 03767388     EISSN: 18733123     Source Type: Journal    
DOI: 10.1016/j.memsci.2014.01.055     Document Type: Article

References (58)

1. Global Natural Gas Production Doubled Between 1980 and 2010, EIA, 2012.
2. Baker R.W., Lokhandwala K. Natural gas processing with membranes: an overview. Ind. Eng. Chem. Res. 2008, 47:2109-2121.
3. Scholes C.A., Stevens G.W., Kentish S.E. Membrane gas separation applications in natural gas processing. Fuel 2012, 96:15-28.
4. Bessarabov D. UGS project uses UOP technology to remove impurities from gas. Membr. Technol. 2010, 2010:2.
5. Bernardo P., Drioli E. Membrane gas separation progresses for process intensification strategy in the petrochemical industry. Pet. Chem. 2010, 50:271-282.
6. Baker R.W. Future directions of membrane gas separation technology. Ind. Eng. Chem. Res. 2002, 41:1393-1411.
7. Robeson L.M. The upper bound revisited. J. Membr. Sci. 2008, 320:390-400.
8. McKeown N.B. Polymers of intrinsic microporosity. ISRN Mater. Sci. 2012, 2012:16.
9. McKeown N.B., Budd P.M. Polymers of intrinsic microporosity (PIMs): organic materials for membrane separations, heterogeneous catalysis and hydrogen storage. Chem. Soc. Rev. 2006, 35:675-683.
10. Budd P.M., Msayib K.J., Tattershall C.E., Ghanem B.S., Reynolds K.J., McKeown N.B., Fritsch D. Gas separation membranes from polymers of intrinsic microporosity. J. Membr. Sci. 2005, 251:263-269.
11. Budd P.M., McKeown N.B., Ghanem B.S., Msayib K.J., Fritsch D., Starannikova L., Belov N., Sanfirova O., Yampolskii Y., Shantarovich V. Gas permeation parameters and other physicochemical properties of a polymer of intrinsic microporosity: polybenzodioxane PIM-1. J. Membr. Sci. 2008, 325:851-860.
12. Budd P.M., Ghanem B.S., Makhseed S., McKeown N.B., Msayib K.J., Tattershall C.E. Polymers of intrinsic microporosity (PIMs): robust, solution-processable, organic nanoporous materials. Chem Commun. 2004, 230-231.
13. Mason C.R., Maynard-Atem L., Al-Harbi N.M., Budd P.M., Bernardo P., Bazzarelli F., Clarizia G., Jansen J.C. Polymer of intrinsic microporosity incorporating thioamide functionality: preparation and gas transport properties. Macromolecules 2011, 44:6471-6479.
14. Ghanem B.S., McKeown N.B., Budd P.M., Al-Harbi N.M., Fritsch D., Heinrich K., Starannikova L., Tokarev A., Yampolskii Y. Synthesis, characterization, and gas permeation properties of a novel group of polymers with intrinsic microporosity: PIM-polyimides. Macromolecules 2009, 42:7881-7888.
15. Weber J., Su O., Antonietti M., Thomas A. Exploring polymers of intrinsic microporosity-microporous, soluble polyamide and polyimide. Macromol. Rapid Commun. 2007, 28:1871-1876.
16. Bezzu C.G., Carta M., Tonkins A., Jansen J.C., Bernardo P., Bazzarelli F., McKeown N.B. A spirobifluorene-based polymer of intrinsic microporosity with improved performance for gas separation. Adv. Mater. 2012, 24:5930.
17. Ma X.H., Swaidan R., Belmabkhout Y., Zhu Y.H., Litwiller E., Jouiad M., Pinnau I., Han Y. Synthesis and gas transport properties of hydroxyl-functionalized polyimides with intrinsic microporosity. Macromolecules 2012, 45:3841-3849.
18. Du N.Y., Robertson G.P., Song J.S., Pinnau I., Thomas S., Guiver M.D. Polymers of intrinsic microporosity containing trifluoromethyl and phenylsulfone groups as materials for membrane gas separation. Macromolecules 2008, 41:9656-9662.
19. Du N.Y., Robertson G.P., Pinnau I., Guiver M.D. Polymers of intrinsic microporosity derived from novel disulfone-based monomers. Macromolecules 2009, 42:6023-6030.
20. 2-capture applications. Nat. Mater. 2011, 10:372-375.
21. Du N.Y., Robertson G.P., Pinnau I., Guiver M.D. Polymers of intrinsic microporosity with dinaphthyl and thianthrene segments. Macromolecules 2010, 43:8580-8587.
22. Carta M., Malpass-Evans R., Croad M., Rogan Y., Jansen J.C., Bernardo P., Bazzarelli F., McKeown N.B. An efficient polymer molecular sieve for membrane gas separations. Science 2013, 339:303-307.
23. Park H.B., Jung C.H., Lee Y.M., Hill A.J., Pas S.J., Mudie S.T., Van Wagner E., Freeman B.D., Cookson D.J. Polymers with cavities tuned for fast selective transport of small molecules and ions. Science 2007, 318:254-258.
24. Carta M., Msayib K.J., McKeown N.B. Novel polymers of intrinsic microporosity (PIMs) derived from 1,1-spiro-bis(1,2,3,4-tetrahydronaphthalene)-based monomers. Tetrahedron Lett. 2009, 50:5954-5957.
25. Carta M., Msayib K.J., Budd P.M., McKeown N.B. Novel spirobisindanes for use as precursors to polymers of intrinsic microporosity. Org. Lett. 2008, 10:2641-2643.
26. Du N., Robertson G.P., Pinnau I., Thomas S., Guiver M.D. Copolymers of intrinsic microporosity based on 2,2[U+05F3],3,3[U+05F3]-tetrahydroxy-1,1[U+05F3]-dinaphthyl. Macromol. Rapid Commun. 2009, 30:584-588.
27. Ghanem B.S., McKeown N.B., Budd P.M., Fritsch D. Polymers of intrinsic microporosity derived from bis(phenazyl) monomers. Macromolecules 2008, 41:1640-1646.
28. Du N.Y., Robertson G.P., Song J.S., Pinnau I., Guiver M.D. High-performance carboxylated polymers of intrinsic microporosity (PIMs) with tunable gas transport properties. Macromolecules 2009, 42:6038-6043.
29. Du N.Y., Robertson G.P., Dal-Cin M.M., Scoles L., Guiver M.D. Polymers of intrinsic microporosity (PIMs) substituted with methyl tetrazole. Polymer 2012, 53:4367-4372.
30. 2 and N-containing organic heterocycles. ChemPhysChem 2009, 10:374-383.
31. 2 capture. Chem. Commun. 2012, 48:9989-9991.
32. 2 capture. RSC Adv. 2013, 3:17203-17213.
33. 2 capture. Energy Environ. Sci. 2011, 4:4528-4531.
34. Sanders E.S. Penetrant-induced plasticization and gas permeation in glassy-polymers. J. Membr. Sci. 1988, 37:63-80.
35. Sanders E.S., Jordan S.M., Subramanian R. Penetrant-plasticized permeation in polymethylmethacrylate. J. Membr. Sci. 1992, 74:29-36.
36. Pinnau I., Toy L.G. Transport of organic vapors through poly(1-trimethylsilyl-1-propyne). J. Membr. Sci. 1996, 116:199-209.
37. Pinnau I., Casillas C.G., Morisato A., Freeman B.D. Hydrocarbon/hydrogen mixed gas permeation in poly(1-trimethylsilyl-1-propyne) (PTMSP), poly(1-phenyl-1-propyne) (PPP), and PTMSP/PPP blends. J. Polym. Sci.: Polym. Phys. 1996, 34:2613-2621.
38. 4 separations. Sep. Purif. Technol. 1998, 14:27-39.
39. Merkel T.C., Freeman B.D., Spontak R.J., He Z., Pinnau I., Meakin P., Hill A.J. Ultrapermeable, reverse-selective nanocomposite membranes. Science 2002, 296:519-522.
40. Visser T., Masetto N., Wessling M. Materials dependence of mixed gas plasticization behavior in asymmetric membranes. J. Membr. Sci. 2007, 306:16-28.
41. Thomas S., Pinnau I., Du N.Y., Guiver M.D. Pure- and mixed-gas permeation properties of a microporous spirobisindane-based ladder polymer (PIM-1). J. Membr. Sci. 2009, 333:125-131.
42. Thomas S., Pinnau I., Du N.Y., Guiver M.D. Hydrocarbon/hydrogen mixed-gas permeation properties of PIM-1, an amorphous microporous spirobisindane polymer. J. Membr. Sci. 2009, 338:1-4.
43. Du N.Y., Dal-Cin M.M., Pinnau I., Nicalek A., Robertson G.P., Guiver M.D. Azide-based cross-linking of polymers of intrinsic microporosity (PIMs) for condensable gas separation. Macromol. Rapid Commun. 2011, 32:631-636.
44. 4 by thermally-rearranged and carbon molecular sieve membranes derived from a polyimide of intrinsic microporosity. J. Membr. Sci. 2013, 447:387-394.
45. Du N.Y., Song J.S., Robertson G.P., Pinnau I., Guiver M.D. Linear high molecular weight ladder polymer via fast polycondensation of 5,5[U+05F3],6,6[U+05F3]-tetrahydroxy-3,3,3[U+05F3],3[U+05F3]-tetramethylspirobisindane with 1,4-dicyanotetrafluorobenzene. Macromol. Rapid Commun. 2008, 29:783-788.
46. Ritter N., Senkovska I., Kaskel S., Weber J. Intrinsically microporous poly(imide)s: structure-porosity relationship studied by gas sorption and x-ray scattering. Macromolecules 2011, 44:2025-2033.
47. Weber J., Du N.Y., Guiver M.D. Influence of intermolecular interactions on the observable porosity in intrinsically microporous polymers. Macromolecules 2011, 44:1763-1767.
48. Weber J., Schmidt J., Thomas A., Bohlmann W. Micropore analysis of polymer networks by gas sorption and Xe-129 NMR spectroscopy: toward a better understanding of intrinsic microporosity. Langmuir 2010, 26:15650-15656.
49. Ritter N., Senkovska I., Kaskel S., Weber J. Towards chiral microporous soluble polymers - binaphthalene-based polyimides. Macromol. Rapid Commun. 2011, 32:438-443.
50. 2 adsorption isotherms. Langmuir 2000, 16:2311-2320.
51. 2 adsorption applied to carbons with various pore size distributions. Carbon 2004, 42:1227-1232.
52. 2 as an adsorptive to characterize carbon molecular sieves and activated carbons. Langmuir 1998, 14:4589-4596.
53. 2 adsorption at 273K for the characterization of porous carbons. Carbon 2004, 42:1233-1242.
54. Nagai K., Higuchi A., Nakagawa T. Gas permeability and stability of poly(1-trimethylsilyl-1-propyne-co-1-phenyl-1-propyne) membranes. J. Polym. Sci.: Polym. Phys. 1995, 33:289-298.
55. O'Brien K.C., Koros W.J., Barbari T.A., Sanders E.S. A new technique for the measurement of multicomponent gas-transport through polymeric films. J. Membr. Sci. 1986, 29:229-238.
56. Jeromenok J., Weber J. Restricted access: on the nature of adsorption/desorption hysteresis in amorphous, microporous polymeric materials. Langmuir 2013, 29:12982-12989.
57. 2 capture. Ind. Eng. Chem. Res. 2013, 52:16939-16950.
58. Wind J.D., Sirard S.M., Paul D.R., Green P.F., Johnston K.P., Koros W.J. Carbon dioxide-induced plasticization of polyimide membranes: pseudo-equilibrium relationships of diffusion, sorption, and swelling. Macromolecules 2003, 36:6433-6441.