Adsorption of n -butanol from dilute aqueous solution with grafted calixarenes

Langmuir

Volumn 27, Issue 19, 2011, Pages 11990-11998

  Thompson, Anthony B ^a   J Cope, Sydney ^a   Swift, T Dallas ^a   Notestein, Justin M ^a  

^a Northwestern University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION OF N-BUTANOL; BRIDGING GROUPS; CALIXARENES; COVALENTLY BOUND; DESOLVATION; DILUTE AQUEOUS SOLUTION; ENTHALPY CHANGE; ENTROPY CHANGES; EQUILIBRIUM CONCENTRATION; FREE ENERGY OF ADSORPTION; GASPHASE; HYDROPHILIC SILICA; N-BUTANOL; ORGANIC LINKERS; REVERSIBLE ADSORPTION; RING SIZES; SILICA SURFACE; SULFUR BRIDGES; SURFACE AREA; SURFACE COVERAGES; SURFACE DENSITY; THIACALIXARENES; VAN DER WAALS INTERACTIONS;

ADSORBENTS; ADSORPTION; ALCOHOLS; DESORPTION; HYDROPHOBICITY; PHENOLS; SILICA; SILICON COMPOUNDS; SOLUTIONS; SULFUR; SURFACES; VAN DER WAALS FORCES;

DRIERS (MATERIALS);

BUTANOL; CALIXARENE; WATER;

ADSORPTION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PARTICLE SIZE; SOLUTION AND SOLUBILITY; STEREOISOMERISM; SURFACE PROPERTY; THERMODYNAMICS;

1-BUTANOL; ADSORPTION; CALIXARENES; MOLECULAR STRUCTURE; PARTICLE SIZE; SOLUTIONS; STEREOISOMERISM; SURFACE PROPERTIES; THERMODYNAMICS; WATER;

EID: 80053314144     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la202508q     Document Type: Article

References (38)

1. Oudshoorn, A.; van der Wielen, L. A. M.; Straathof, A. J. J. Assessment of options for selective 1-butanol recovery from aqueous solution Ind. Eng. Chem. Res. 2009, 48, 7325-7336
2. Haynes, W. M., Ed. CRC Handbook of Chemistry and Physics, 91 st ed.; CRC Press/Taylor & Francis: Boca Raton, FL, 2011.
3. Qureshi, N.; Hughes, S.; Maddox, I. S.; Cotta, M. A. Energy-efficient recovery of butanol from model solutions and fermentation broth by adsorption Bioprocess Biosyst. Eng. 2005, 27, 215-222 (Pubitemid 40980363)
4. Oudshoorn, A.; van der Wielen, L. A. M.; Straathof, A. J. J. Adsorption equilibria of bio-based butanol solutions using zeolites Biochem. Eng. J. 2009, 48, 99-103
5. Nielsen, D. R.; Prather, K. J. In situ product recovery of n-butanol using polymeric resins Biotechnol. Bioeng. 2009, 102, 811-821
6. Notestein, J. M.; Katz, A.; Iglesia, E. Energetics of small molecule and water complexation in hydrophobic calixarene cavities Langmuir 2006, 22, 4004-4014
7. Katz, A.; Da Costa, P.; Lam, A. C. P.; Notestein, J. M. The first single-step immobilization of a calix-[4]-arene onto the surface of silica Chem. Mater. 2002, 14, 3364-3368
8. 13C CP MAS NMR and X-ray crystallography Chem. Commun. 1998, 5, 587-588 (Pubitemid 128666890)
9. Chen, M.; Chen, Y.; Diao, G. Adsorption kinetics and thermodynamics of methylene blue onto p-tert -butyl-calix[4,6,8]arene-bonded silica gel J. Chem. Eng. Data 2010, 55, 5109-5116
10. Brindle, R.; Albert, K.; Harris, S. J.; Troltzsch, C.; Horne, E.; Glennon, J. D. Silica-bonded calixarenes in chromatography I. Synthesis and characterization by solid-state NMR spectroscopy J. Chromatogr., A 1996, 731, 41-46 (Pubitemid 26150135)
11. Gorbatchuk, V. V.; Tsifarkin, A. G.; Antipin, I. S.; Solomonov, B. N.; Konovalov, A. I.; Seidel, J.; Baitalov, F. Thermodynamic comparison of molecular recognition of vaporous guests by solid calixarene and diol hosts J. Chem. Soc., Perkin Trans. 2 2000, 2287-2294 (Pubitemid 35165728)
12. Schierbaum, K. D.; Weiss, T.; Vanvelzen, E. U. T.; Engbersen, J. F. J.; Reinhoudt, D. N.; Gopel, W. Molecular recognition by self-assembled monolayers of cavitand receptors Science 1994, 265, 1413-1415 (Pubitemid 24306793)
13. Sokoließ, T.; Schönherr, J.; Menyes, U.; Roth, U.; Jira, T. Characterization of calixarene- and resorcinarene-bonded stationary phases: I. Hydrophobic interactions J. Chromatogr., A 2003, 1021, 71-82 (Pubitemid 37357013)
14. Böhmer, V. Calixarenes, macrocycles with (almost) unlimited possibilities Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745
15. Ghoufi, A.; Morel, J. P.; Morel-Desrosiers, N.; Malfreyt, P. MD simulations of the binding of alcohols and diols by a calixarene in water: connections between microscopic and macroscopic properties J. Phys. Chem. B 2005, 109, 23579-23587 (Pubitemid 43081531)
16. Gutsche, C. D.; Lin, L. G. Calixarenes 12: the synthesis of functionalized calixarenes Tetrahedron 1986, 42, 1633-1640
17. Almi, M.; Arduini, A.; Casnati, A.; Pochini, A.; Ungaro, R. Chloromethylation of calixarenes and synthesis of new water soluble macrocyclic hosts Tetrahedron 1989, 45, 2177-2182
18. Maczynski, A.; Shaw, D. G.; Goral, M.; Wisniewska-Goclowska, B. IUPAC-NIST solubility data series. 82. Alcohols with water-revised and updated: part 1. C4 alcohols with water J. Phys. Chem. Ref. Data 2007, 36, 59-132
19. Shiraishi, S.; Komiyama, M.; Hirai, H. Immobilization of beta-cyclodextrin on silica-gel Bull. Chem. Soc. Jpn. 1986, 59, 507-510
20. Fan, M.; Shevchenko, I. V.; Voorhies, R. H.; Eckert, S. F.; Zhang, H.; Lattman, M. Main-group-element calix[4]arenes: variable coordination and conformational isomerism at phosphorus and silicon Inorg. Chem. 2000, 39, 4704-4712
21. Hajek, F.; Graf, E.; Hosseini, M. W. Multicavitands IV: synthesis of linear koilands obtained by fusion of calix[4]arene derivatives by silicon atoms Tetrahedron Lett. 1996, 37, 1409-1412
22. Delaigue, X.; Hosseini, M. W.; De Cian, A.; Fischer, J.; Leize, E.; Kieffer, S.; Van Dorsselaer, A. Multicavitands I: synthesis and X-ray crystal structure of a bis p-tert-butylcalix[4]arene fused by two silicon atoms Tetrahedron Lett. 1993, 34, 3285-3288
23. Shang, S.; Khasnis, D. V.; Burton, J. M.; Santini, C. J.; Fan, M.; Small, A. C.; Lattman, M. From a novel silyl p-tert-butylcalix[4]arene triether to mono-O-alkyl substitution: a unique, efficient, and selective route to mono-O-substituted calix[4]arenes Organometallics 1994, 13, 5157-5159
24. Stoikov, I.; Mostovaya, O.; Antipin, I.; Konovalov, A.; Grüner, M.; Habicher, W. Synthesis and spatial structure of novel organosilicon derivatives of p-tert-butylthiacalix[4]arene from two-dimensional NMR data Russ. Chem. Bull. 2007, 56, 307-312
25. Dabrowski, A.; Jaroniec, M. Theoretical foundations of physical adsorption from binary non-electrolytic liquid mixtures on solid surfaces: present and future Adv. Colloid Interface Sci. 1987, 27, 211-283
26. Jaroniec, M.; Madey, R.; Dabrowski, A. Assessment of microporosity in porous adsorbents by comparing the liquid-solid adsorption isotherms Langmuir 1989, 5, 987-990
27. Brunauer, S.; Emmett, P. H.; Teller, E. Adsorption of gases in multimolecular layers J. Am. Chem. Soc. 1938, 60, 309
28. Derylo, A.; Jaroniec, M. Multi-solute adsorption from dilute-solutions on solids Chem. Scr. 1982, 19, 108-115
29. Choma, J.; Jaroniec, M.; Burakiewicz-Mortka, W.; Gilpin, R. K. Studies of the structural heterogeneity of microporous carbons using liquid/solid adsorption isotherms Langmuir 1993, 9, 2555-2561
30. Jaroniec, M.; Dabrowski, A.; Toth, J. Multilayer single-solute adsorption from dilute solutions on energetically heterogeneous solids Chem. Eng. Sci. 1984, 39, 65-70 (Pubitemid 14549984)
31. Radke, C. J.; Prausnitz, J. M. Adsorption of organic solutes from dilute aqueous solution on activated carbon Ind. Eng. Chem. Fundam. 1972, 11, 445-451
32. Terzyk, A. P.; Rychlicki, G.; Cwiertnia, M. S.; Gauden, P. A.; Kowalczyk, P. Effect of the carbon surface layer chemistry on benzene adsorption from the vapor phase and from dilute aqueous solutions Langmuir 2005, 21, 12257-12267 (Pubitemid 43037191)
33. Dohnal, V.; Fenclová, D.; Vrbka, P. Temperature dependences of limiting activity coefficients, Henry's law constants, and derivative infinite dilution properties of lower (C1-C5) 1-alkanols in water. critical compilation, correlation, and recommended data J. Phys. Chem. Ref. Data 2006, 35, 1621-1651 (Pubitemid 44913373)
34. Gupta, A. K.; Teja, A. S.; Chai, X. S.; Zhu, J. Y. Henry's constants of n-alkanols (methanol through n-hexanol) in water at temperatures between 40 and 90 °C Fluid Phase Equilib. 2000, 170, 183-192 (Pubitemid 32472200)
35. Iki, N.; Miyano, S. Can thiacalixarene surpass calixarene? J. Inclusion Phenom. Macrocyclic Chem. 2001, 41, 99-105 (Pubitemid 33383984)
36. Kobayashi, K.; Asakawa, Y.; Kikuchi, Y.; Toi, H.; Aoyama, Y. CH-π interaction as an important driving force of host-guest complexation in apolar organic media. Binding of monools and acetylated compounds to resorcinol cyclic tetramer as studied by proton NMR and circular dichroism spectroscopy J. Am. Chem. Soc. 1993, 115, 2648-2654
37. Sone, T.; Ohba, Y.; Moriya, K.; Kumada, H.; Ito, K. Synthesis and properties of sulfur-bridged analogs of p-tert-butylcalix[4]arene Tetrahedron 1997, 53, 10689-10698 (Pubitemid 27308546)
38. Arena, G.; Contino, A.; Gulino, F. G.; Magri, A.; Sciotto, D.; Ungaro, R. Complexation of small neutral organic molecules by water soluble calix[4]arenes Tetrahedron Lett. 2000, 41, 9327-9330