Application of the Chemical-Looping Concept for Azoetrope Separation

Abstract The need for the separation of azeotropic mixtures for the production of high-end chemicals and resource recovery has spurred significant research into the development of new separation methods in the chemical industry. In this paper, a green and sustainable method for azeotrope separation is proposed based on a chemical-looping concept with the help of reversible-reaction-assisted distillation. The central concept in the chemical-looping separation (CLS) method is the selection of a reactant that can react with the azeotrope components and can also be recycled by the reverse reaction to close the loop and achieve cyclic azeotrope separation. This paper aims to provide an informative perspective on the fundamental theory and applications of the CLS method based on the separation principle, reactant selection, and case analysis, for example, the separation of alkenes, alkane, aromatics, and polyol products. In summary, we provide guidance and references for chemical separation process intensification in product refining and separation from azeotropic systems for the development of a more sustainable chemical industry.

[1]  Dawei Wang,et al.  250 kWth high pressure pilot demonstration of the syngas chemical looping system for high purity H2 production with CO2 capture , 2018, Applied Energy.

[2]  H. Sui,et al.  Efficiency of Mixture Separation in Distillation Columns with Structured Packings under Different Ways of Dynamically Controlled Irrigation , 2019, Journal of Engineering Thermophysics.

[3]  Xingang Li,et al.  Heat-integrated reactive distillation process for TAME synthesis , 2014 .

[4]  Song Fu-rong Advances in Olefin Production Technology by Catalytic Cracking , 2002 .

[5]  Tao Zhang,et al.  Synthesis of ethylene glycol and terephthalic acid from biomass for producing PET , 2016 .

[6]  F. Mccandless,et al.  The separation of meta- and para-xylene by pervaporation in the presence of CBr4, a selective feed-complexing agent , 1992 .

[7]  H. Mohameed,et al.  Separation of para-xylene from xylene mixture via crystallization , 2007 .

[8]  P. Steltenpohl,et al.  Methyl acetate–methanol mixture separation by extractive distillation: Economic aspects , 2018, Frontiers of Chemical Science and Engineering.

[9]  Ihsan Hamawand,et al.  Direct Reaction of Silicon with Ethyl Chloride in a Fluidized Bed Reactor , 2009 .

[10]  I. Ortiz,et al.  Comparative study of conventional, reactive-distillation and pervaporation integrated hybrid process for ethyl tert-butyl ether production , 2017 .

[11]  Sanjay M. Mahajani,et al.  Dimerized isobutene : An alternative to MTBE , 2001 .

[12]  Zhigang Lei,et al.  Extractive distillation with ionic liquids: A review , 2014 .

[13]  Kang Ma,et al.  Energy-saving thermally coupled ternary extractive distillation process by combining with mixed entrainer for separating ternary mixture containing bioethanol , 2018 .

[14]  A. A. Kiss,et al.  Enhanced bioethanol dehydration by extractive and azeotropic distillation in dividing-wall columns , 2012 .

[16]  Yufeng Hu,et al.  Separation of para-xylene and meta-xylene by extraction process using aqueous cyclodextrins solution , 2017 .

[17]  Reversible reaction-assisted intensification process for separating the azeotropic mixture of ethanediol and 1,2-butanediol:Reactants screening , 2018 .

[18]  Hong Li,et al.  State‐of‐the‐Art of Advanced Distillation Technologies in China , 2016 .

[19]  B. Subramaniam,et al.  Comparative Economic and Environmental Assessments of H2O2-based and Tertiary Butyl Hydroperoxide-based Propylene Oxide Technologies , 2013 .

[20]  A. Zlatkis,et al.  Gas Chromatographic Separation of Meta-and Para-Xylenes in Aromatic Mixtures , 1958, Nature.

[21]  SEPARATION OF META- AND PARA-XYLENE MIXTURE BY DISTILLATION ACCOMPANIED BY CHEMICAL REACTIONS , 1971 .

[22]  Alex E. S. Green,et al.  Systematics and modeling representations of naphtha thermal cracking for olefin production , 2005 .

[23]  A. Abad,et al.  Chemical Looping Combustion in a 10 kWth Prototype Using a CuO/Al2O3 Oxygen Carrier: Effect of Operating Conditions on Methane Combustion , 2006 .

[24]  Hong Li,et al.  Reversible Reaction-Assisted Intensification Process for Separating the Azeotropic Mixture of Ethanediol and 1,2-Butanediol: Vapor–Liquid Equilibrium and Economic Evaluation , 2018 .

[25]  Kangnian Fan,et al.  Cu/SiO2 catalysts prepared by the ammonia-evaporation method: Texture, structure, and catalytic performance in hydrogenation of dimethyl oxalate to ethylene glycol , 2008 .

[26]  S. Shishatskiy,et al.  Development of CO 2 Selective Poly(Ethylene Oxide)-Based Membranes: From Laboratory to Pilot Plant Scale , 2017 .

[27]  Xingang Li,et al.  Synthesis of 1,3-Dioxolane from Aqueous Formaldehyde Solution and Ethylene Glycol: Kinetics and Reactive Distillation , 2019, Industrial & Engineering Chemistry Research.

[28]  L. Fan,et al.  Chemical looping processes for CO2 capture and carbonaceous fuel conversion – prospect and opportunity , 2012 .

[29]  Hongguang Jin,et al.  A NEW ADVANCED POWER-GENERATION SYSTEM USING CHEMICAL-LOOPING COMBUSTION , 1994 .

[30]  A. Klerk Etherification of C6 Fischer−Tropsch Material for Linear α-Olefin Recovery , 2004 .

[31]  Hong Li,et al.  Reversible reaction-assisted intensification process for separating ethanediol and 1, 2-butanediol: Competitive kinetics study and conceptual design , 2020 .

[32]  W. Arlt,et al.  Hyperbranched polymers: new selective solvents for extractive distillation and solvent extraction , 2002 .

[33]  Yinglong Wang,et al.  Insight into pressure-swing distillation from azeotropic phenomenon to dynamic control , 2017 .

[34]  D. A. Bender,et al.  Peer Reviewed: MTBE-To What Extent Will Past Releases Contaminate Community Water Supply Wells? , 2000, Environmental science & technology.

[35]  N. Kuipers,et al.  Effect of C6-olefin isomers on π-complexation for purification of 1-hexene by reactive extractive distillation , 2005 .

[36]  Achim Kienle,et al.  Separation using coupled reactive distillation columns , 2000 .

[37]  X. Geng,et al.  Optimization of liquid–liquid extraction combined with either heterogeneous azeotropic distillation or extractive distillation processes to reduce energy consumption and carbon dioxide emissions , 2018 .

[38]  M. Spérandio,et al.  Study of a hybrid process: Adsorption on activated carbon/membrane bioreactor for the treatment of an industrial wastewater , 2008 .

[39]  E. Santiso,et al.  Carbon Sequestration through CO2 Foam-Enhanced Oil Recovery: A Green Chemistry Perspective , 2018, Engineering.

[40]  Hong Li,et al.  Application of the aldolization reaction in separating the mixture of ethylene glycol and 1,2-butanediol: Kinetics and reactive distillation , 2017 .

[41]  Jifeng Pang,et al.  Selective removal of 1,2‐propanediol and 1,2‐butanediol from bio‐ethylene glycol by catalytic reaction , 2017 .

[42]  and Kejin Huang,et al.  Design and Control of a Methyl Tertiary Butyl Ether (MTBE) Decomposition Reactive Distillation Column , 2007 .

[43]  Chao Wen,et al.  Reaction temperature controlled selective hydrogenation of dimethyl oxalate to methyl glycolate and ethylene glycol over copper-hydroxyapatite catalysts , 2015 .

[44]  J. B. Montón,et al.  Study of liquid–liquid extraction of ethanol + water azeotropic mixtures using two imidazolium-based ionic liquids , 2018 .

[45]  Hong Li,et al.  Application of the Aldolization Reaction in Separating the Mixture of Ethylene Glycol and 1,2-Butanediol: Thermodynamics and New Separation Process , 2016 .

[46]  Kai Sundmacher,et al.  Selectivity Engineering with Reactive Distillation for Dimerization of C4 Olefins: Experimental and Theoretical Studies , 2007 .

[47]  D. Krishnaiah,et al.  Effect of ultrasound on liquid phase adsorption of azeotropic and non-azeotropic mixture , 2008 .

[48]  Shrawan Baghel,et al.  Polymeric Amorphous Solid Dispersions: A Review of Amorphization, Crystallization, Stabilization, Solid-State Characterization, and Aqueous Solubilization of Biopharmaceutical Classification System Class II Drugs. , 2016, Journal of pharmaceutical sciences.

[49]  A. Abad,et al.  Selection of Oxygen Carriers for Chemical-Looping Combustion , 2004 .

[50]  S. Chopade,et al.  Acetalization of ethylene glycol with formaldehyde using cation-exchange resins as catalysts: batch versus reactive distillation , 1997 .

[51]  Rafiqul Gani,et al.  A systematic synthesis framework for extractive distillation processes , 2008 .

[52]  B. Saha,et al.  Recovery of dilute acetic acid through esterification in a reactive distillation column , 2000 .

[53]  Omid Bakhtiari,et al.  Industrial grade 1-butene/isobutane separation using supported liquid membranes , 2017 .

[54]  X. Geng,et al.  Computer-Aided Screening of Ionic Liquids As Entrainers for Separating Methyl Acetate and Methanol via Extractive Distillation , 2018, Industrial & Engineering Chemistry Research.

[55]  Moses O. Tadé,et al.  MULTIPLICITY AND PSEUDO-MULTIPLICITY IN MTBE AND ETBE REACTIVE DISTILLATION , 1998 .

[56]  Hong Li,et al.  Innovative Reactive Distillation Process for the Sustainable Synthesis of Natural Benzaldehyde , 2018, ACS Sustainable Chemistry & Engineering.

[57]  de Ab André Haan,et al.  Functionalized Solvents for Olefin Isomer Purification by Reactive Extractive Distillation , 2007 .

[58]  Zhiyong Guo,et al.  Sustainable Separations of C4‐Hydrocarbons by Using Microporous Materials , 2017, ChemSusChem.

[59]  Hong Li,et al.  Fundamentals and applications of microwave heating to chemicals separation processes , 2019, Renewable and Sustainable Energy Reviews.

[60]  Uthaiporn Suriyapraphadilok,et al.  Systematic screening methodology and energy efficient design of ionic liquid-based separation processes , 2016 .

[61]  Kangnian Fan,et al.  Highly active and selective copper-containing HMS catalyst in the hydrogenation of dimethyl oxalate to ethylene glycol , 2008 .

[62]  P. Anastas,et al.  Designing for a green chemistry future , 2020, Science.

[63]  N. Kuipers,et al.  Synthesis and Evaluation of Metal−Ligand Complexes for Selective Olefin Solubilization in Reactive Solvents , 2005 .

[64]  K. Sundmacher,et al.  Process Analysis for Dimerization of Isobutene by Reactive Distillation , 2006 .

[65]  Seyyed Shahabeddin Azimi,et al.  Three-phase modeling of dehydrogenation of isobutane to isobutene in a fluidized bed reactor: Effect of operating conditions on the energy consumption , 2018 .

[66]  Novel Route for Recovery of Glycerol from Aqueous Solutions by Reversible Reactions , 2009 .

[67]  Liang-Shih Fan,et al.  Chemical Looping Technology and Its Fossil Energy Conversion Applications , 2010 .

[68]  Peisheng Ma,et al.  Isobaric Vapor–Liquid Equilibrium for the Binary System (Ethane-1,2-diol + Butan-1,2-diol) at (20, 30, and 40) kPa , 2014 .

[69]  Zhigang Lei,et al.  Extractive distillation with the mixture of ionic liquid and solid inorganic salt as entrainers , 2014 .

[70]  Lin Zhu,et al.  Life-cycle assessment of SNG and power generation: The role of implement of chemical looping combustion for carbon capture , 2019, Energy.

[71]  J. Lavoie,et al.  Effect of temperature in the conversion of methanol to olefins (MTO) using an extruded SAPO-34 catalyst , 2018, Frontiers of Chemical Science and Engineering.

[72]  Hong Li,et al.  Ethylene Glycol Recovery from 2-Ethyl-1,3-dioxolane Hydrolysis via Reactive Distillation: Pilot-Scale Experiments and Process Analysis , 2019, Industrial & Engineering Chemistry Research.

[73]  L. Fan,et al.  Parametric and dynamic studies of an iron-based 25-kWth coal direct chemical looping unit using sub-bituminous coal , 2015 .

[74]  A. Hiltner,et al.  Crystallization and phase separation in blends of high stereoregular poly(lactide) with poly(ethylene glycol) , 2003 .

[75]  Jian Chen,et al.  Separation of C6-Olefin Isomers in Reactive Extractants , 2008 .

[76]  A. Ubando,et al.  Iron oxide reduction by torrefied microalgae for CO2 capture and abatement in chemical-looping combustion , 2019, Energy.

[77]  A. A. Kiss,et al.  Reactive Distillation: Stepping Up to the Next Level of Process Intensification , 2018, Industrial & Engineering Chemistry Research.

[78]  A. Lyngfelt,et al.  Chemical-looping combustion and chemical-looping with oxygen uncoupling of kerosene with Mn- and Cu-based oxygen carriers in a circulating fluidized-bed 300 W laboratory reactor , 2012 .

[79]  Qilong Ren,et al.  Selective Extraction of 1-Hexene Against n-Hexane in Ionic Liquids with or without Silver Salt , 2012 .

[80]  De Haan,et al.  Olefin isomer separation by reactive extractive distillation: Modelling of vapour–liquid equilibria and conceptual design for 1-hexene purification , 2007 .

[81]  William L. Luyben Comparison of flowsheets for THF/water separation using pressure-swing distillation , 2018, Comput. Chem. Eng..

[82]  K. S. Egorova,et al.  Biological Activity of Ionic Liquids and Their Application in Pharmaceutics and Medicine. , 2017, Chemical reviews.

[83]  Yujie Ban,et al.  Metal-organic framework-based mixed matrix membranes: Synergetic effect of adsorption and diffusion for CO2/CH4 separation , 2018, Journal of Membrane Science.

[84]  Richard Baur,et al.  Dynamic simulation of reactive distillation: An MTBE case study , 1996 .

[85]  Yongri Liang,et al.  Effect of Mesophase Separation on the Crystallization Behavior of Olefin Block Copolymers , 2010 .

[86]  R. Palkovits,et al.  Alternative Monomers Based on Lignocellulose and Their Use for Polymer Production. , 2016, Chemical reviews.