Abstract
Increasing energy prices, global warming, and concerns for environmental pollution has been pushing the chemical industry to look for alternatives for traditional, fossil-based chemical feedstocks. Important platform molecules are alcohols, which can be produced from renewable feedstocks via fermentation. The implementation of these fermentation processes to produce chemicals leads to important challenges regarding the downstream purification. Adsorption-based purification technologies are alternatives for traditional energy-intensive distillation processes. The well-defined pore structure of zeolites makes them ideal candidates for the removal of alcohols from these complex fermentation mixtures, which contain cells and cell debris, acids, sugars, lipids, and proteins. The following chapter covers important aspects in the adsorption mechanism of alcohols and water in (mainly) hydrophobic zeolite pores, such as cluster formation and hydrogen bonding. These effects inevitably also play a role when looking at the diffusion of alcohols inside the zeolite pores. Finally, this chapter will cover some examples of studies where hydrophobic zeolites have been used to recover bio-alcohols, such as biobutanol and bioethanol, from model solutions or fermentation broths via fixed-bed separations.
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References
Sheldon RA (2014) Green and sustainable manufacture of chemicals from biomass: state of the art. Green Chem 16:950–963. https://doi.org/10.1039/c3gc41935e
Climent MJ, Corma A, Iborra S (2014) Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels. Green Chem 16:516–547. https://doi.org/10.1039/C3GC41492B
Schutyser W, Renders T, Van Den Bosch S et al (2018) Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading. Chem Soc Rev. https://doi.org/10.1039/c7cs00566k
Koutinas AA, Vlysidis A, Pleissner D et al (2014) Valorization of industrial waste and by-product streams via fermentation for the production of chemicals and biopolymers. Chem Soc Rev 43:2587–2627. https://doi.org/10.1039/c3cs60293a
Menon V, Rao M (2012) Trends in bioconversion of lignocellulose: biofuels, platform chemicals & biorefinery concept. Prog Energy Combust Sci 38:522–550. https://doi.org/10.1016/j.pecs.2012.02.002
Kushwaha D, Srivastava N, Mishra I et al (2019) Recent trends in biobutanol production. Rev Chem Eng 35:475–504. https://doi.org/10.1515/revce-2017-0041
Ibrahim MF, Kim SW, Abd-Aziz S (2018) Advanced bioprocessing strategies for biobutanol production from biomass. Renew Sust Energ Rev 91:1192–1204. https://doi.org/10.1016/j.rser.2018.04.060
Kujawska A, Kujawski J, Bryjak M, Kujawski W (2015) ABE fermentation products recovery methods – a review. Renew Sust Energ Rev 48:648–661. https://doi.org/10.1016/j.rser.2015.04.028
Chen C, Liao JC (2016) Frontiers in microbial 1-butanol and isobutanol production. FEMS Microbiol Lett 363:1–13. https://doi.org/10.1093/femsle/fnw020
Branduardi P, de Ferra F, Longo V, Porro D (2013) Microbial n-butanol production from clostridia to non-clostridial hosts. Eng Life Sci 14:16–26. https://doi.org/10.1002/elsc.201200146
Atsumi S, Hanai T, Liao JC (2008) Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels. Nature 451:86–89. https://doi.org/10.1038/nature06450
Mohd Azhar SH, Abdulla R, Jambo SA et al (2017) Yeasts in sustainable bioethanol production: a review. Biochem Biophys Rep 10:52–61. https://doi.org/10.1016/j.bbrep.2017.03.003
Ahn JH, Jang YS, Lee SY (2016) Production of succinic acid by metabolically engineered microorganisms. Curr Opin Biotechnol 42:54–66. https://doi.org/10.1016/j.copbio.2016.02.034
De Roos J, De Vuyst L (2018) Acetic acid bacteria in fermented foods and beverages. Curr Opin Biotechnol 49:115–119. https://doi.org/10.1016/j.copbio.2017.08.007
Juturu V, Wu JC (2016) Microbial production of lactic acid: the latest development. Crit Rev Biotechnol 36:967–977. https://doi.org/10.3109/07388551.2015.1066305
Cañete-Rodríguez AM, Santos-Dueñas IM, Jiménez-Hornero JE et al (2016) Gluconic acid: properties, production methods and applications—an excellent opportunity for agro-industrial by-products and waste bio-valorization. Process Biochem 51:1891–1903. https://doi.org/10.1016/j.procbio.2016.08.028
Whited GM, Feher FJ, Benko DA et al (2010) Development of a gas-phase bioprocess for isoprene-monomer production using metabolic pathway engineering. Ind Biotechnol 6:152–163. https://doi.org/10.1089/ind.2010.6.152
Van Leeuwen BNM, Van Der Wulp AM, Duijnstee I et al (2012) Fermentative production of isobutene. Appl Microbiol Biotechnol 93:1377–1387. https://doi.org/10.1007/s00253-011-3853-7
Garg SK, Jain A (1995) Fermentative production of 2,3-butanediol: a review. Bioresour Technol 51:103–109. https://doi.org/10.1016/0960-8524(94)00136-O
Biebl H, Menzel K, Zeng AP, Deckwer WD (1999) Microbial production of 1,3-propanediol. Appl Microbiol Biotechnol 52:289–297
Maiorella B, Wilke CR, Blanch HW (1981) Alcohol production and recovery. pp 43–92
Jones DT, Woods DR (1986) Acetone-butanol fermentation revisited. Microbiol Rev 50:484–524
Soccol CR, de Vandenberghe LPS, Medeiros ABP et al (2010) Bioethanol from lignocelluloses: status and perspectives in Brazil. Bioresour Technol 101:4820–4825. https://doi.org/10.1016/j.biortech.2009.11.067
Amorim HV, Lopes ML, de Castro Oliveira JV et al (2011) Scientific challenges of bioethanol production in Brazil. Appl Microbiol Biotechnol 91:1267–1275. https://doi.org/10.1007/s00253-011-3437-6
Takahara I, Saito M, Inaba M, Murata K (2005) Dehydration of ethanol into ethylene over solid acid catalysts. Catal Lett 105:249–252. https://doi.org/10.1007/s10562-005-8698-1
Mao RLV, Nguyen TM, McLaughlin GP (1989) The bioethanol-to-ethylene (B.E.T.E.) process. Appl Catal 48:265–277. https://doi.org/10.1016/S0166-9834(00)82798-0
Mascal M (2012) Chemicals from biobutanol: technologies and markets. Biofuels Bioprod Biorefin 6:483–493. https://doi.org/10.1002/bbb.1328
Chiao JS, Sun ZH (2007) History of the acetone-butanol-ethanol fermentation industry in China: development of continuous production technology. J Mol Microbiol Biotechnol 13:12–14. https://doi.org/10.1159/000103592
Peters MW, Taylor JD, Jenni MM et al (2011) Integrated process to selectively convert renewable isobutanol to p-xylene. US Patent 2011/0087000 A1
Baeyens J, Kang Q, Appels L et al (2015) Challenges and opportunities in improving the production of bio-ethanol. Prog Energy Combust Sci 47:60–88. https://doi.org/10.1016/j.pecs.2014.10.003
Abdehagh N, Sharif A, Tezel H et al (2014) Energy-efficient recovery of butanol from model solutions and fermentation broth by adsorption. Eng Life Sci 27:215–222. https://doi.org/10.1007/s00449-005-0402-8
Matsumura M, Kataoka H, Sueki M, Araki K (1988) Energy saving effect of pervaporation using oleyl alcohol liquid membrane in butanol purification. Bioprocess Eng 3:93–100. https://doi.org/10.1007/BF00369334
Oudshoorn A, Van Der Wielen LAM, Straathof AJJ (2009) Assessment of options for selective 1-butanol recovery from aqueous solution. Ind Eng Chem Res 48:7325–7336. https://doi.org/10.1021/ie900537w
Adhami L, Griggs B, Himebrook P, Taconi K (2009) Liquid–liquid extraction of butanol from dilute aqueous solutions using soybean-derived biodiesel. J Am Oil Chem Soc 86:1123–1128. https://doi.org/10.1007/s11746-009-1447-7
Solana M, Qureshi N, Bertucco A, Eller F (2016) Recovery of butanol by counter-current carbon dioxide fractionation with its potential application to butanol fermentation. Materials (Basel) 9:530. https://doi.org/10.3390/ma9070530
Kurkijärvi AJ, Lehtonen J (2014) Dual extraction process for the utilization of an acetone-butanol-ethanol mixture in gasoline. Ind Eng Chem Res 53:12379–12386. https://doi.org/10.1021/ie500131x
Abdehagh N (2016) Improvements in biobutanol production : separation and recovery by adsorption. PhD thesis, University of Ottawa. https://doi.org/10.20381/ruor-5344
Ezeji TC, Qureshi N, Blaschek HP (2004) Acetone butanol ethanol (ABE) production from concentrated substrate: reduction in substrate inhibition by fed-batch technique and product inhibition by gas stripping. Appl Microbiol Biotechnol 63:653–658. https://doi.org/10.1007/s00253-003-1400-x
Cai D, Chen H, Chen C et al (2016) Gas stripping-pervaporation hybrid process for energy-saving product recovery from acetone-butanol-ethanol (ABE) fermentation broth. Chem Eng J 287:1–10. https://doi.org/10.1016/j.cej.2015.11.024
Groot WJ, van der Lans RGJM, Luyben KCAM (1989) Batch and continuous butanol fermentations with free cells: integration with product recovery by gas-stripping. Appl Microbiol Biotechnol 32:305–308. https://doi.org/10.1007/BF00184979
Van Hecke W, Vandezande P, Dubreuil M et al (2016) Biobutanol production from C5/C6 carbohydrates integrated with pervaporation: experimental results and conceptual plant design. J Ind Microbiol Biotechnol 43:25–36. https://doi.org/10.1007/s10295-015-1717-3
Van Hecke W, De Wever H (2017) High-flux POMS organophilic pervaporation for ABE recovery applied in fed-batch and continuous set-ups. J Membr Sci 540:321–332. https://doi.org/10.1016/j.memsci.2017.06.058
Van Hecke W, Hofmann T, De Wever H (2013) Pervaporative recovery of ABE during continuous cultivation: enhancement of performance. Bioresour Technol 129:421–429. https://doi.org/10.1016/j.biortech.2012.11.072
Van Hecke W, Vandezande P, Claes S et al (2012) Integrated bioprocess for long-term continuous cultivation of clostridium acetobutylicum coupled to pervaporation with PDMS composite membranes. Bioresour Technol 111:368–377. https://doi.org/10.1016/j.biortech.2012.02.043
Thongsukmak A, Sirkar KK (2007) Pervaporation membranes highly selective for solvents present in fermentation broths. J Membr Sci 302:45–58. https://doi.org/10.1016/j.memsci.2007.06.013
Negishi H, Sakaki K, Ikegami T (2010) Silicalite pervaporation membrane exhibiting a separation factor of over 400 for butanol. Chem Lett 39:1312–1314. https://doi.org/10.1246/cl.2010.1312
Abdehagh N, Tezel FH, Thibault J (2013) Adsorbent screening for biobutanol separation by adsorption: kinetics, isotherms and competitive effect of other compounds. Adsorption 19:1263–1272. https://doi.org/10.1007/s10450-013-9566-8
Faisal A, Zhou M, Hedlund J, Grahn M (2016) Recovery of butanol from model ABE fermentation broths using MFI adsorbent: a comparison between traditional beads and a structured adsorbent in the form of a film. Adsorption 22:205–214. https://doi.org/10.1007/s10450-016-9759-z
Lin X, Wu J, Fan J et al (2012) Adsorption of butanol from aqueous solution onto a new type of macroporous adsorption resin: studies of adsorption isotherms and kinetics simulation. J Chem Technol Biotechnol 87:924–931. https://doi.org/10.1002/jctb.3701
Lin X, Wu J, Jin X et al (2012) Selective separation of biobutanol from acetone-butanol-ethanol fermentation broth by means of sorption methodology based on a novel macroporous resin. Biotechnol Prog 28:962–972. https://doi.org/10.1002/btpr.1553
Lin X, Xiong L, Qi G et al (2015) Using butanol fermentation wastewater for biobutanol production after removal of inhibitory compounds by micro/mesoporous hyper-cross-linked polymeric adsorbent. ACS Sustain Chem Eng 3:702–709. https://doi.org/10.1021/acssuschemeng.5b00010
Oudshoorn A, van der Wielen LAM, Straathof AJJ (2009) Adsorption equilibria of bio-based butanol solutions using zeolite. Biochem Eng J 48:99–103. https://doi.org/10.1016/j.bej.2009.08.014
Qureshi N, Hughes S, Maddox IS, Cotta MA (2005) Energy-efficient recovery of butanol from model solutions and fermentation broth by adsorption. Bioprocess Biosyst Eng 27:215–222. https://doi.org/10.1007/s00449-005-0402-8
Abdehagh N, Tezel FH, Thibault J (2014) Separation techniques in butanol production: challenges and developments. Biomass Bioenergy 60:222–246. https://doi.org/10.1016/j.biombioe.2013.10.003
Abdehagh N, Gurnani P, Tezel FH, Thibault J (2015) Adsorptive separation and recovery of biobutanol from ABE model solutions. Adsorption 21:185–194. https://doi.org/10.1007/s10450-015-9661-0
Cousin Saint Remi J, Remy T, Vanhunskerken V et al (2011) Biobutanol separation with the metal-organic framework ZIF-8. ChemSusChem 4:1074–1077. https://doi.org/10.1002/cssc.201100261
Cousin Saint Remi J, Baron G, Denayer J (2012) Adsorptive separations for the recovery and purification of biobutanol. Adsorption 18:367–373. https://doi.org/10.1007/s10450-012-9415-1
Cousin-Saint-Remi J, Finoulst A-L, Jabbour C et al (2019) Selection of binder recipes for the formulation of MOFs into resistant pellets for molecular separations by fixed-bed adsorption. Microporous Mesoporous Mater. https://doi.org/10.1016/j.micromeso.2019.02.009
Van der Perre S, Gelin P, Claessens B et al (2017) Intensified biobutanol recovery by using zeolites with complementary selectivity. ChemSusChem 10:2968–2977. https://doi.org/10.1002/cssc.201700667
Cousin-Saint-Remi J, Van Der Perre S, Segato T et al (2019) Highly robust MOF polymeric beads with controllable size for molecular separations. ACS Appl Mater Interfaces 11:13694–13703. https://doi.org/10.1021/acsami.9b00521
Faisal A, Zarebska A, Saremi P et al (2014) MFI zeolite as adsorbent for selective recovery of hydrocarbons from ABE fermentation broths. Adsorption 20:465–470. https://doi.org/10.1007/s10450-013-9576-6
Li SY, Chiang CJ, Tseng IT et al (2016) Bioreactors and in situ product recovery techniques for acetone-butanol-ethanol fermentation. FEMS Microbiol Lett 363:1–7. https://doi.org/10.1093/femsle/fnw107
Qureshi N, Blaschek H (2001) Evaluation of recent advances in butanol fermentation, upstream, and downstream processing. Bioprocess Biosyst Eng 24:219–226. https://doi.org/10.1007/s004490100257
Roffler S, Blanch HW, Wilke CR (1987) Extractive fermentation of acetone and butanol: process design and economic evaluation. Biotechnol Prog 3:131–140. https://doi.org/10.1002/btpr.5420030304
Sánchez-Ramírez E, Quiroz-Ramírez JJ, Segovia-Hernández JG et al (2015) Process alternatives for biobutanol purification: design and optimization. Ind Eng Chem Res 54:351–358. https://doi.org/10.1021/ie503975g
Patraşcu I, Bîldea CS, Kiss AA (2017) Eco-efficient butanol separation in the ABE fermentation process. Sep Purif Technol 177:49–61. https://doi.org/10.1016/j.seppur.2016.12.008
Hahn H-D, Dämbkes G, Rupprich N et al (2013) Butanols. Ullmann’s Encycl Ind Chem. https://doi.org/10.1002/14356007.a04_463.pub3
Abdehagh N, Dai B, Thibault J, Handan Tezel F (2017) Biobutanol separation from ABE model solutions and fermentation broths using a combined adsorption-gas stripping process. J Chem Technol Biotechnol 92:245–224. https://doi.org/10.1002/jctb.4977
Levario TJ, Dai M, Yuan W et al (2012) Rapid adsorption of alcohol biofuels by high surface area mesoporous carbons. Microporous Mesoporous Mater 148:107–114. https://doi.org/10.1016/j.micromeso.2011.08.001
Abdehagh N, Tezel FH, Thibault J (2016) Multicomponent adsorption modeling: isotherms for ABE model solutions using activated carbon F-400. Adsorption 22:357–370. https://doi.org/10.1007/s10450-016-9784-y
Xue C, Liu F, Xu M et al (2016) Butanol production in acetone-butanol-ethanol fermentation with in situ product recovery by adsorption. Bioresour Technol 219:158–168. https://doi.org/10.1016/j.biortech.2016.07.111
Groot WJ, Luyben KCAM (1986) In situ product recovery by adsorption in the butanol/isopropanol batch fermentation. Appl Microbiol Biotechnol 25:29–31. https://doi.org/10.1007/bf00252508
Lee SH, Yun EJ, Kim J et al (2016) Biomass, strain engineering, and fermentation processes for butanol production by solventogenic clostridia. Appl Microbiol Biotechnol 100:8255–8271. https://doi.org/10.1007/s00253-016-7760-9
Lin X, Li R, Wen Q et al (2013) Experimental and modeling studies on the sorption breakthrough behaviors of butanol from aqueous solution in a fixed-bed of KA-I resin. Biotechnol Bioprocess Eng 18:223–233. https://doi.org/10.1007/s12257-012-0549-5
Liu D, Chen Y, Ding F-Y et al (2014) Biobutanol production in a clostridium acetobutylicum biofilm reactor integrated with simultaneous product recovery by adsorption. Biotechnol Biofuels 7:5. https://doi.org/10.1186/1754-6834-7-5
Nielsen DR, Prather KJ (2009) In situ product recovery of n-butanol using polymeric resins. Biotechnol Bioeng 102:811–821. https://doi.org/10.1002/bit.22109
Nielsen L, Larsson M, Holst O, Mattiasson B (1988) Adsorbents for extractive bioconversion applied to the acetone-butanol fermentation. Appl Microbiol Biotechnol 28:335–339. https://doi.org/10.1007/BF00268191
Raganati F, Procentese A, Olivieri G et al (2018) Bio-butanol separation by adsorption on various materials: assessment of isotherms and effects of other ABE-fermentation compounds. Sep Purif Technol 191:328–339. https://doi.org/10.1016/j.seppur.2017.09.059
Wu J, Zhuang W, Ying H et al (2015) Acetone-butanol-ethanol competitive sorption simulation from single, binary, and ternary systems in a fixed-bed of KA-I resin. Biotechnol Prog 31:124–134. https://doi.org/10.1002/btpr.2019
Yang X, Tsai GJ, Tsao GT (1994) Enhancement of in situ adsorption on the acetone-butanol fermentation by clostridium acetobutylicum. Sep Technol 4:81–92. https://doi.org/10.1016/0956-9618(94)80009-X
Ennis BM, Qureshi N, Maddox IS (1987) In-line toxic product removal during solvent production by continuous fermentation using immobilized clostridium acetobutylicum. Enzym Microb Technol 9:672–675. https://doi.org/10.1016/0141-0229(87)90126-8
Eom MH, Kim W, Lee J et al (2013) Modeling of a biobutanol adsorption process for designing an extractive fermentor. Ind Eng Chem Res 52:603–611. https://doi.org/10.1021/ie301249z
Gusler GM, Browne TE, Cohen Y (1993) Sorption of organics from aqueous solution onto polymeric resins. Ind Eng Chem Res 32:2727–2735. https://doi.org/10.1021/ie00023a040
Jiao P, Wu J, Ji Y et al (2015) Desorption of 1-butanol from polymeric resin: experimental studies and mathematical modeling. RSC Adv 5:105464–105474. https://doi.org/10.1039/C5RA21986H
Jiao P, Wu J, Zhou J et al (2015) Mathematical modeling of the competitive sorption dynamics of acetone-butanol-ethanol on KA-I resin in a fixed-bed column. Adsorption 21:165–176. https://doi.org/10.1007/s10450-015-9659-7
Bhattacharyya S, Jayachandrababu KC, Chiang Y et al (2017) Butanol separation from humid CO 2 -containing multicomponent vapor mixtures by zeolitic imidazolate frameworks. ACS Sustain Chem Eng 5:9467–9476. https://doi.org/10.1021/acssuschemeng.7b02604
Martin-Calvo A, Van der Perre S, Claessens B et al (2018) Unravelling the influence of carbon dioxide on the adsorptive recovery of butanol from fermentation broth using ITQ-29 and ZIF-8. Phys Chem Chem Phys 20:9957–9964. https://doi.org/10.1039/C8CP01034J
Raganati F, Procentese A, Olivieri G et al (2018) Separation and purification technology bio-butanol separation by adsorption on various materials: assessment of isotherms and effects of other ABE-fermentation compounds. Sep Purif Technol 191:328–339. https://doi.org/10.1016/j.seppur.2017.09.059
Cousin-Saint-Remi J, Van der Perre S, Segato T et al (2019) Highly robust MOF polymeric beads with a controllable size for molecular separations. ACS Appl Mater Interfaces 11:13694–13703. https://doi.org/10.1021/acsami.9b00521
Lefevere J, Claessens B, Mullens S et al (2019) 3D-printed zeolitic imidazolate framework structures for adsorptive separations. ACS Appl Nano Mater 2:4991–4999. https://doi.org/10.1021/acsanm.9b00934
Nalaparaju A, Zhao XS, Jiang JW (2010) Molecular understanding for the adsorption of water and alcohols in hydrophilic and hydrophobic zeolitic metal− organic frameworks. J Phys Chem C 114:11542–11550. https://doi.org/10.1021/jp1033273
Gee JA, Chung J, Nair S, Sholl DS (2013) Adsorption and diffusion of small alcohols in zeolitic imidazolate frameworks ZIF-8 and ZIF-90. J Phys Chem C 117:3169–3176. https://doi.org/10.1021/jp312489w
Zhang K, Lively RP, Zhang C et al (2013) Exploring the framework hydrophobicity and flexibility of zif-8: from biofuel recovery to hydrocarbon separations. J Phys Chem Lett 4:3618–3622. https://doi.org/10.1021/jz402019d
Zhang K, Lively RP, Dose ME et al (2013) Alcohol and water adsorption in zeolitic imidazolate frameworks. Chem Commun 49:3245–3247. https://doi.org/10.1039/c3cc39116g
Van Der Perre S, Van Assche T, Bozbiyik B et al (2014) Adsorptive characterization of the ZIF-68 metal-organic framework: a complex structure with amphiphilic properties. Langmuir 30:8416–8424. https://doi.org/10.1021/la501594t
Zhang K, Nalaparaju A, Chen Y, Jiang J (2014) Biofuel purification in zeolitic imidazolate frameworks: the significant role of functional groups. Phys Chem Chem Phys 16:9643–9655. https://doi.org/10.1039/c4cp00739e
Gao C, Wu J, Shi Q et al (2017) Adsorption breakthrough behavior of 1-butanol from an ABE model solution with high-silica zeolite: comparison with zeolitic imidazolate frameworks (ZIF-8). Microporous Mesoporous Mater 243:119–129. https://doi.org/10.1016/j.micromeso.2017.02.009
Castillo JM, Silvestre-Albero J, Rodriguez-Reinoso F et al (2013) Water adsorption in hydrophilic zeolites: experiment and simulation. Phys Chem Chem Phys 15:17374–17382. https://doi.org/10.1039/c3cp52910j
Calero S, Gómez-Álvarez P (2014) Effect of the confinement and presence of cations on hydrogen bonding of water in LTA-type zeolite. J Phys Chem C 118:9056–9065. https://doi.org/10.1021/jp5014847
Gabruś E, Downarowicz D (2016) Anhydrous ethanol recovery from wet air in TSA systems – equilibrium and column studies. Chem Eng J 288:321–331. https://doi.org/10.1016/j.cej.2015.11.110
Remy T, Cousin Saint Remi J, Singh R et al (2011) Adsorption and separation of C1 À C8 alcohols on SAPO-34. J Phys Chem C 115:8117–8125. https://doi.org/10.1021/jp111615e
Miyamoto M, Iwatsuka H, Oumi Y et al (2019) Effect of core-shell structuring of chabazite zeolite with a siliceous zeolite thin layer on the separation of acetone-butanol-ethanol vapor in humid vapor conditions. Chem Eng J 363:292–299. https://doi.org/10.1016/j.cej.2019.01.106
Maddox IS (1982) Use of silicalite for the adsorption of n-butanol from fermentation liquors. Biotechnol Lett 4:759–760. https://doi.org/10.1007/BF00134673
Milestone NB, Bibby DM (1983) Adsorption of alcohols from aqueous solution by ZSM-5. J Chem Technol Biotechnol Chem Technol 34:73–79. https://doi.org/10.1002/jctb.5040340205
Ake TR (1984) Recovery of ethanol from low concentration solution by adsorption with Silicalite. Master thesis, Iowa State University
Haegh GS (1985) Zeolites as adsorbents for alcohols from aqueous solutions. Stud Surf Sci Catal 24:605–609. https://doi.org/10.1016/S0167-2991(08)65332-X
Franks PA (1986) Adsorption of ethanol water mixtures on high silica zeolites. PhD thesis, Imperial College London
Einicke W-D, Messow U, Schöllner R (1988) Liquid-phase adsorption of n-alcohol/water mixtures on zeolite NaZSM-5. J Colloid Interface Sci 122:280–282. https://doi.org/10.1016/0021-9797(88)90310-4
Sowerby B, Crittenden BD (1988) Vapour phase separation of alcohol-water mixtures by adsorption onto silicalite. Gas Sep Purif 2:177–183. https://doi.org/10.1016/0950-4214(88)80003-3
Dubinin MM, Rakhmatkariev GU, Isirikyan AA (1989) Heats of adsorption of methanol and ethanol on high-silicon ZSM-5 zeolite. Bull Acad Sci USSR Div Chem Sci 38:2419–2421. https://doi.org/10.1007/BF01168102
Dubinin MM, Rakhmatkariev GU, Isirikyan AA (1989) Differential heats of adsorption and adsorption isotherms of alcohols on silicalite. Bull Acad Sci USSR Div Chem Sci 38:1950–1953. https://doi.org/10.1007/BF00957798
Einicke W, Heuchel M, Szombathely MV et al (1989) Liquid-phase adsorption of binary ethanol–water mixtures on NaZSM-5 zeolites with different silicon/aluminium ratios. J Chem Soc Faraday Trans 1 Phys Chem Condens Phases 85:4277–4285. https://doi.org/10.1039/f19898504277
Einicke W, Messow U, Heuchel M et al (1991) Liquid-phase adsorption of ethanol–water mixtures on NaZSM-5 zeolite with inorganic and organic binders. J Chem Soc Faraday Trans 87:1283–1286. https://doi.org/10.1039/FT9918701283
Holtzapple MT, Flores KL, Brown RF (1994) Recovery of volatile solutes from dilute aqueous solutions using immobilized silicalite. Sep Technol 4:230–238. https://doi.org/10.1016/0956-9618(94)80026-X
Farhadpour FA, Bono A (1996) Sorptive separation of ethanol-water mixtures with a bi-dispersed hydrophobic molecular sieve, silicalite: determination of the controlling mass transfer mechanism. Chem Eng Process Process Intensif 35:141–155. https://doi.org/10.1016/0255-2701(95)04138-9
Farhadpour FA, Bono A (1988) Adsorption from solution of nonelectrolytes by microporous crystalline solids: ethanol-water/silicalite system. J Colloid Interface Sci 124:209–227. https://doi.org/10.1016/0021-9797(88)90341-4
Oumi Y, Miyajima A, Miyamoto J, Sano T (2002) Binary mixture adsorption of water and ethanol on silicalite. Stud Surf Sci Catal:1595–1602. https://doi.org/10.1016/s0167-2991(02)80329-9
Bowen TC, Vane LM (2006) Ethanol, acetic acid, and water adsorption from binary and ternary liquid mixtures on high-silica zeolites. Langmuir 22:3721–3727. https://doi.org/10.1021/la052538u
Saravanan V, Waijers DA, Ziari M, Noordermeer MA (2010) Recovery of 1-butanol from aqueous solutions using zeolite ZSM-5 with a high Si/Al ratio; suitability of a column process for industrial applications. Biochem Eng J 49:33–39. https://doi.org/10.1016/j.bej.2009.11.008
Xiong R, Sandler SI, Vlachos DG (2011) Alcohol adsorption onto silicalite from aqueous solution. J Phys Chem C 115:18659–18669. https://doi.org/10.1021/jp205312k
Oudshoorn A, van der Wielen LAM, Straathof AJJ (2012) Desorption of butanol from zeolite material. Biochem Eng J 67:167–172. https://doi.org/10.1016/j.bej.2012.06.014
Zhang K, Lively RP, Noel JD et al (2012) Adsorption of water and ethanol in MFI-type zeolites. Langmuir 28:8664–8673. https://doi.org/10.1021/la301122h
Bai P, Tsapatsis M, Siepmann JI (2012) Multicomponent adsorption of alcohols onto silicalite-1 from aqueous solution: isotherms, structural analysis, and assessment of ideal adsorbed solution theory. Langmuir 28:15566–15576. https://doi.org/10.1021/la303247c
Águeda VI, Delgado JA, Uguina MA et al (2013) Column dynamics of an adsorption-drying-desorption process for butanol recovery from aqueous solutions with silicalite pellets. Sep Purif Technol 104:307–321. https://doi.org/10.1016/j.seppur.2012.11.036
DeJaco RF, Bai P, Tsapatsis M, Siepmann JI (2016) Adsorptive separation of 1-butanol from aqueous solutions using MFI- and FER-type zeolite frameworks: a Monte Carlo study. Langmuir 32:2093–2101. https://doi.org/10.1021/acs.langmuir.5b04483
Faisal A, Zhou M, Hedlund J, Grahn M (2018) Zeolite MFI adsorbent for recovery of butanol from ABE fermentation broths produced from an inexpensive black liquor-derived hydrolyzate. Biomass Conv Bioref 8:679–687. https://doi.org/10.1007/s13399-018-0315-9
Rutkai G, Csányi É, Kristóf T (2008) Prediction of adsorption and separation of water–alcohol mixtures with zeolite NaA. Microporous Mesoporous Mater 114:455–464. https://doi.org/10.1016/j.micromeso.2008.01.044
Krishna R, Van Baten JM (2010) Hydrogen bonding effects in adsorption of water-alcohol mixtures in zeolites and the consequences for the characteristics of the Maxwell-Stefan diffusivities. Langmuir 26:10854–10867. https://doi.org/10.1021/la100737c
Yamamoto T, Kim YH, Kim BC et al (2012) Adsorption characteristics of zeolites for dehydration of ethanol: evaluation of diffusivity of water in porous structure. Chem Eng J 181–182:443–448. https://doi.org/10.1016/j.cej.2011.11.110
Simo M, Sivashanmugam S, Brown CJ, Hlavacek V (2009) Adsorption/desorption of water and ethanol on 3A zeolite in near-adiabatic fixed bed. Ind Eng Chem Res 48:9247–9260. https://doi.org/10.1021/ie900446v
Bedard R, Liu C (2018) Recent advances in zeolitic membranes. Annu Rev Mater Res 48:83–110. https://doi.org/10.1146/annurev-matsci-070317-124605
Jyothi MS, Reddy KR, Soontarapa K et al (2019) Membranes for dehydration of alcohols via pervaporation. J Environ Manag 242:415–429. https://doi.org/10.1016/j.jenvman.2019.04.043
Khalid A, Aslam M, Qyyum MA et al (2019) Membrane separation processes for dehydration of bioethanol from fermentation broths: recent developments, challenges, and prospects. Renew Sust Energ Rev 105:427–443. https://doi.org/10.1016/j.rser.2019.02.002
Couck S, Lefevere J, Mullens S et al (2017) CO 2, CH 4 and N 2 separation with a 3DFD-printed ZSM-5 monolith. Chem Eng J 308:719–726. https://doi.org/10.1016/j.cej.2016.09.046
Kokotailo GT, Lawton SL, Olson DH, Meier WM (1978) Structure of synthetic zeolite ZSM-5. Nature 272:437–438. https://doi.org/10.1038/272437a0
Farzaneh A, Zhou M, Potapova E et al (2015) Adsorption of water and butanol in silicalite-1 film studied with in situ attenuated total reflectance-Fourier transform infrared spectroscopy. Langmuir 31:4887–4894. https://doi.org/10.1021/acs.langmuir.5b00489
Flanigen EM, Bennett JM, Grose RW et al (1978) Silicalite, a new hydrophobic crystalline silica molecular sieve. Nature 271:512–516. https://doi.org/10.1038/271512a0
Milestone NB, Bibby DM (1981) Concentration of alcohols by adsorption on silicalite. J Chem Technol Biotechnol 31:732–736. https://doi.org/10.1002/jctb.503310198
Olson DH, Kokotailo GT, Lawton SL, Meier WM (1981) Crystal structure and structure-related properties of ZSM-5. J Phys Chem 85:2238–2243. https://doi.org/10.1021/j150615a020
Baerlocher C, McCusker LB. Database of zeolite structures. http://www.iza-structure.org/databases/
Kooyman PJ, van der Waal P, van Bekkum H (1997) Acid dealumination of ZSM-5. Zeolites 18:50–53. https://doi.org/10.1016/S0144-2449(96)00106-6
Thamm H (1987) Adsorption site heterogeneity in silicalite: a calorimetric study. Zeolites 7:341–346. https://doi.org/10.1016/0144-2449(87)90037-6
Farhadpour FA, Bono A (1996) Sorptive separation of ethanol-water mixtures with a bi-dispersed hydrophobic molecular sieve, silicalite: measurement and theoretical analysis of column dynamics. Chem Eng Process Process Intensif 35:157–168. https://doi.org/10.1016/0255-2701(95)04139-7
Hunger B, Matysik S, Heuchel M, Einicke W (1997) Adsorption of methanol on ZSM-5 zeolites. Langmuir 13:6249–6254. https://doi.org/10.1021/la970615i
Cekova B, Kocev D, Kolcakovska E, Stojanova D (2006) Zeolites as alcohol adsorbents from aqueous solutions. Acta Period Technol 192:83–87. https://doi.org/10.2298/APT0637083C
Costa RJ, Castro EAS, Politi JRS et al (2019) Methanol, ethanol, propanol, and butanol adsorption on H-ZSM-5 zeolite: an ONIOM study. J Mol Model 25:34. https://doi.org/10.1007/s00894-018-3894-2
Shubin AA, Catlow CRA, Thomas JM, Zamaraev KI (2006) A computational study of the adsorption of the isomers of butanol on silicalite and H-ZSM-5. Proc R Soc A Math Phys Eng Sci 446:411–427. https://doi.org/10.1098/rspa.1994.0112
Boddenberg B, Rakhmatkariev GU, Greth R (2002) Statistical thermodynamics of methanol and ethanol adsorption in zeolite NaZSM5. J Phys Chem B 101:1634–1640. https://doi.org/10.1021/jp963111m
Ramachandran CE, Chempath S, Broadbelt LJ, Snurr RQ (2006) Water adsorption in hydrophobic nanopores: Monte Carlo simulations of water in silicalite. Microporous Mesoporous Mater 90:293–298. https://doi.org/10.1016/j.micromeso.2005.10.021
Trzpit M, Soulard M, Patarin J et al (2007) The effect of local defects on water adsorption in silicalite-1 zeolite: a joint experimental and molecular simulation study. Langmuir 23:10131–10139. https://doi.org/10.1021/la7011205
Castillo JM, Dubbeldam D, Vlugt TJH et al (2009) Evaluation of various water models for simulation of adsorption in hydrophobic zeolites. Mol Simul 35:1067–1076. https://doi.org/10.1080/08927020902865923
Özgür Yazaydin A, Thompson RW (2009) Molecular simulation of water adsorption in silicalite: effect of silanol groups and different cations. Microporous Mesoporous Mater 123:169–176. https://doi.org/10.1016/j.micromeso.2009.03.045
Ari MU, Ahunbay MG, Yurtsever M, Erdem-Şenatalar A (2009) Molecular dynamics simulation of water diffusion in MFI-type zeolites. J Phys Chem B 113:8073–8079. https://doi.org/10.1021/jp901986s
Alexopoulos K, Lee M-S, Liu Y et al (2016) Anharmonicity and confinement in zeolites: structure, spectroscopy, and adsorption free energy of ethanol in H-ZSM-5. J Phys Chem C 120:7172–7182. https://doi.org/10.1021/acs.jpcc.6b00923
Xiong R, Sandler SI, Vlachos DG (2012) Molecular screening of alcohol and polyol adsorption onto MFI-type zeolites. Langmuir 28:4491–4499. https://doi.org/10.1021/la204710j
Gómez-Álvarez P, Noya EG, Lomba E et al (2018) Study of short-chain alcohol and alcohol–water adsorption in MEL and MFI zeolites. Langmuir 34:12739–12750. https://doi.org/10.1021/acs.langmuir.8b02326
Nguyen CM, Reyniers MF, Marin GB (2010) Theoretical study of the adsorption of C1-C4 primary alcohols in H-ZSM-5. Phys Chem Chem Phys 12:9481–9493. https://doi.org/10.1039/c000503g
Nguyen CM, Reyniers M-F, Marin GB (2011) Theoretical study of the adsorption of the butanol isomers in H-ZSM-5. J Phys Chem C 115:8658–8669. https://doi.org/10.1021/jp111698b
Denayer JF, Souverijns W, Jacobs PA et al (1998) High-temperature low-pressure adsorption of branched C5-C8 alkanes on zeolite beta, ZSM-5, ZSM-22, zeolite Y, and mordenite. J Phys Chem B 102:4588–4597. https://doi.org/10.1021/jp980674k
Olson DH, Haag WO, Borghard WS (2000) Use of water as a probe of zeolitic properties: interaction of water with HZSM-5. Microporous Mesoporous Mater 35–36:435–446. https://doi.org/10.1016/S1387-1811(99)00240-1
Desbiens N, Boutin A, Demachy I (2005) Water condensation in hydrophobic silicalite-1 zeolite: a molecular simulation study. J Phys Chem B 109:24071–24076. https://doi.org/10.1021/jp054168o
Desbiens N, Demachy I, Fuchs AH et al (2005) Water condensation in hydrophobic nanopores. Angew Chem Int Ed 44:5310–5313. https://doi.org/10.1002/anie.200501250
Pellenq RJM, Roussel T, Puibasset J (2008) Molecular simulations of water in hydrophobic microporous solids. Adsorption 14:733–742. https://doi.org/10.1007/s10450-008-9135-8
Puibasset J, Pellenq RJM (2008) Grand canonical Monte Carlo simulation study of water adsorption in silicalite at 300 K. J Phys Chem B 112:6390–6397. https://doi.org/10.1021/jp7097153
Guth JL, Kessler H (1999) Catalysis and zeolites – fundamentals and applications. In: Weitkamp J, Puppe L (eds) Catalysis and zeolites. Springer, Berlin. https://doi.org/10.1007/978-3-662-03764-5
Guth JL, Kessler H, Higel JM, et al (1989) Zeolite synthesis in the presence of fluoride ions. In: ACS symposium series. Zeolite synthesis, vol 398. pp 176–195. https://doi.org/10.1021/bk-1989-0398.ch013
Ahunbay MG (2011) Monte Carlo simulation of water adsorption in hydrophobic MFI zeolites with hydrophilic sites. Langmuir 27:4986–4993. https://doi.org/10.1021/la200685c
Rouquerol F, Rouquerol J, Sing K (1999) Adsorption at the liquid–solid interface: thermodynamics and methodology. In: Adsorption by powders and porous solids – principles, methodology and applications. Academic Press, London, pp 117–163
Dejaco RF, Bai P, Tsapatsis M, Siepmann JI (2016) Adsorptive separation of 1-butanol from aqueous solutions using MFI-and FER-type zeolite frameworks: a Monte Carlo study. Langmuir 32:2093–2101. https://doi.org/10.1021/acs.langmuir.5b04483
Caro J, Bülow M, Richter-Mendau J et al (1987) Nuclear magnetic resonance self-diffusion studies of methanol-water mixtures in pentasil-type zeolites. J Chem Soc Faraday Trans 1 Phys Chem Condens Phases 83:1843–1849. https://doi.org/10.1039/F19878301843
Nayak VS, Moffat JB (1988) Sorption and diffusion of alcohols in heteropoly oxometalates and ZSM-5 zeolite. J Phys Chem 92:7097–7102. https://doi.org/10.1021/j100336a014
Choudhary VR, Mamman AS, Nayak VS (1989) Mass transfer of liquid cumene in ZSM-5 zeolites using a novel volumetric apparatus. Ind Eng Chem Res 28:1241–1245. https://doi.org/10.1021/ie00092a019
Choudhary VR, Singh AP (1986) Sorption capacity and diffusion of pure liquids in ZSM-5 type zeolites. Zeolites 6:206–208. https://doi.org/10.1016/0144-2449(86)90049-7
Demontis P, Stara G, Suffritti GB (2003) Behavior of water in the hydrophobic zeolite silicalite at different temperatures. A molecular dynamics study. J Phys Chem B 107:4426–4436. https://doi.org/10.1021/jp0300849
Fleys M, Thompson RW, MacDonald JC (2004) Comparison of the behavior of water in silicalite and dealuminated zeolite y at different temperatures by molecular dynamic simulations. J Phys Chem B 108:12197–12203. https://doi.org/10.1021/jp040229r
Bussai C, Vasenkov S, Liu H et al (2002) On the diffusion of water in silicalite-1: MD simulations using ab initio fitted potential and PFG NMR measurements. Appl Catal A Gen 232:59–66. https://doi.org/10.1016/S0926-860X(02)00066-2
Yu M, Falconer JL, Noble RD, Krishna R (2007) Modeling transient permeation of polar organic mixtures through a MFI zeolite membrane using the Maxwell-Stefan equations. J Membr Sci 293:167–173. https://doi.org/10.1016/j.memsci.2007.02.015
Holtzapple MT, Brown RF (1994) Conceptual design for a process to recover volatile solutes from aqueous solutions using silicalite. Sep Technol 4:213–229. https://doi.org/10.1016/0956-9618(94)80025-1
Huang HJ, Ramaswamy S, Tschirner UW, Ramarao BV (2008) A review of separation technologies in current and future biorefineries. Sep Purif Technol 62:1–21. https://doi.org/10.1016/j.seppur.2007.12.011
Jost S, Biswas P, Schüring A et al (2007) Structure and self-diffusion of water molecules in chabazite: a molecular dynamics study. J Phys Chem C 111:14707–14712. https://doi.org/10.1021/jp073857s
Krishna R, Van Baten JM (2011) Entropy-based separation of linear chain molecules by exploiting differences in the saturation capacities in cage-type zeolites. Sep Purif Technol 76:325–330. https://doi.org/10.1016/j.seppur.2010.10.023
Daems I, Singh R, Baron G, Denayer J (2007) Length exclusion in the adsorption of chain molecules on chabazite type zeolites. Chem Commun (Camb):1316–1318. https://doi.org/10.1039/b615661d
Cousin-Saint-Remi J, Lauerer A, Chmelik C et al (2016) The role of crystal diversity in understanding mass transfer in nanoporous materials. Nat Mater 15:401–406. https://doi.org/10.1038/nmat4510
Cousin-Saint-Remi J, Baron GV, Denayer JFM (2013) Nonuniform chain-length-dependent diffusion of short 1-alcohols in SAPO-34 in liquid phase. J Phys Chem C 117:9758–9765. https://doi.org/10.1021/jp312287k
Cosseron AF, Daou TJ, Tzanis L et al (2013) Adsorption of volatile organic compounds in pure silica CHA, *bEA, MFI and STT-type zeolites. Microporous Mesoporous Mater 173:147–154. https://doi.org/10.1016/j.micromeso.2013.02.009
Chen D, Rebo HP, Moljord K, Holmen A (1999) Methanol conversion to light olefins over SAPO-34. Sorption, diffusion, and catalytic reactions. Ind Eng Chem Res 38:4241–4249. https://doi.org/10.1021/ie9807046
Corma A, Rey F, Rius J et al (2004) Supramolecular self-assembled molecules as organic directing agent for synthesis of zeolites. Nature 431:287–290. https://doi.org/10.1038/nature02909
Reed TB, Breck DW (1956) Crystalline zeolites. II. Crystal structure of synthetic zeolite, type A. J Am Chem Soc 78:5972–5977. https://doi.org/10.1021/ja01604a002
Morris B (1968) Heats of sorption in the crystalline linde-A zeolite-water vapor system. J Colloid Interface Sci 28:149–155. https://doi.org/10.1016/0021-9797(68)90216-6
Higgins FM, de Leeuw NH, Parker SC (2002) Modelling the effect of water on cation exchange in zeolite A. J Mater Chem 12:124–131. https://doi.org/10.1039/b104069n
Gorbach A, Stegmaier M, Eigenberger G (2004) Measurement and modeling of water vapor adsorption on zeolite 4A – equilibria and kinetics. Adsorption 10:29–46. https://doi.org/10.1023/B:ADSO.0000024033.60103.ff
Lalik E, Mirek R, Rakoczy J, Groszek A (2006) Microcalorimetric study of sorption of water and ethanol in zeolites 3A and 5A. Catal Today 114:242–247. https://doi.org/10.1016/j.cattod.2006.01.006
Csányi É, Kristóf T, Lendvay G (2009) Potential model development using quantum chemical information for molecular simulation of adsorption equilibria of water−methanol (ethanol) mixtures in zeolite NaA-4. J Phys Chem C 113:12225–12235. https://doi.org/10.1021/jp902520p
Gramlich V, Meier WM (1971) The crystal structure of hydrated NaA: a detailed refinement of a pseudosymmetric zeolite structure. Zeitschrift fur Krist New Cryst Struct 133:134–149. https://doi.org/10.1524/zkri.1971.133.133.134
Weigel O, Steinhoff E (1924) IX. Die Aufnahme organischer Flüssigkeitsdämpfe durch Chabasit. Zeitschrift für Krist Cryst Mater 61:125–154. https://doi.org/10.1524/zkri.1924.61.1.125
Skazyvaev VE, Khvoshchev SS, Zhdanov SP (1976) Molecular-sieve properties of synthetic chabazites. Bull Acad Sci USSR Div Chem Sci 25:12–16. https://doi.org/10.1007/BF00925609
Daems I, Singh R, Baron G, Denayer J (2007) Length exclusion in the adsorption of chain molecules on chabazite type zeolites. Chem Commun:1316–1318. https://doi.org/10.1039/b615661d
Jaramillo E, Chandross M (2004) Adsorption of small molecules in LTA zeolites. 1. NH 3, CO 2, and H 2 O in zeolite 4A. J Phys Chem B 108:20155–20159. https://doi.org/10.1021/jp048078f
Kristóf T, Csányi É, Rutkai G, Merényi L (2006) Prediction of adsorption equilibria of water–methanol mixtures in zeolite NaA by molecular simulation. Mol Simul 32:869–875. https://doi.org/10.1080/08927020600934179
Xiao Y, He G, Yuan M (2018) Adsorption equilibrium and kinetics of methanol vapor on zeolites NaX, KA, and CaA and activated alumina. Ind Eng Chem Res 57:14254–14260. https://doi.org/10.1021/acs.iecr.8b04076
Dyer A, Amin S (2001) Self-diffusion of simple alcohols in heteroinic forms of LTA zeolites. Microporous Mesoporous Mater 46:163–176. https://doi.org/10.1016/S1387-1811(01)00280-3
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Claessens, B., Cousin-Saint-Remi, J., Denayer, J.F.M. (2020). Efficient Downstream Processing of Renewable Alcohols Using Zeolite Adsorbents. In: Valencia, S., Rey, F. (eds) New Developments in Adsorption/Separation of Small Molecules by Zeolites. Structure and Bonding, vol 184. Springer, Cham. https://doi.org/10.1007/430_2020_68
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