醇-水体系中醇回收技术进展

摘要/Abstract

摘要： 根据所含碳原子数不同，将醇类物质分为高碳醇及低碳醇。详细综述了高碳醇和低碳醇-水体系中醇回收技术的研究进展，并从能耗、原料组成、产物纯度及收率等技术经济性方面比较了各种技术的优劣；分析结果表明，液-液萃取是高碳醇回收的主流技术；由于兼顾了不同技术的优势并规避了各自的缺陷，组合技术将成为实现醇-水体系中低碳醇回收技术绿色化及高效节能化的重要发展方向；而化学链分离（CLS）法对于多元醇的回收具有更大潜力。

关键词: 醇-水体系, 醇回收, 高/低碳醇, 组合技术, 化学链分离

Abstract: Alcohols can be divided into high-carbon alcohols and low-carbon alcohols according to the number of carbon atoms contained in alcohols. The research progress of alcohol recovery technology in the alcohol-water system of high-carbon alcohol and low-carbon alcohol was reviewed in detail, and the advantages and disadvantages of each technology were compared in terms of energy consumption, raw material composition, purity and yield of product. The results showed that liquid-liquid extraction was the main technology for recovering high-carbon alcohol; due to the advantages of different technologies and the avoidance of their defects, the combined technology would become an important development direction to realize green and efficient energy saving of low carbon alcohol recovery technology in alcohol-water system. Chemical Looping Separation (CLS) had greater potential for polyol recovery from polyol-water system.

Key words: alcohol-water system, alcohol recovery, high/low carbon alcohol, combination technology, chemical looping separation

王雪香王建明张春孙耀华朱建华. 醇-水体系中醇回收技术进展[J]. 石油炼制与化工, 2023, 54(2): 134-144.

参考文献

[1]BANIER D, VOLKERT Z J.A Separation method and reactor system for a glycol-water mixture: EP3883912A1[P]. 2021-09-29 [2] 日高秀人, 佐藤陽平.Water-alcohol separation system and method for water-alcohol separation for the production of alcohol: JP2020075865A[P]. 2020-05-21 [3] NESTERENKO N, DPONT C, COUPARD V, et al.Process for dehydration of mono-alcohol(s) using a modified crystalline aluminosilicate:US10851028B2[P]. 2020-12-01 [4] Hidaka H, Sato Y.Water-alcohol separation system and water-alcohol separation method for producing alcohol: US20200009507A1[P]. 2020-01-09. [5] VERMA R, NAIK P K, DIAZ I, et al.Separation of Low Molecular Weight Alcohols from Water with Deep Eutectic Solvents: Liquid-Liquid Equilibria and Process Simulations[J].Fluid Phase Equilibria, 2021, 533(533):112949-112949 [6]STEPHENSON R, STUART J, TABAK M.Mutual solubility of water and aliphatic alcohols[J].Journal of Chemical & Engineering Data, 1984, 29(3):287-290 [7]SHCHELOKOVA E A, KOPKOVA E K, GROMOV P B, et al.Solubility of monohydric aliphatic alcohols in water and aqueous HCl solutions[J].Russian Journal of Applied Chemistry, 2012, 85(3):465-469 [8]CHEN J T, CHEN M C.Liquid–Liquid Equilibria for the Quaternary Systems of Water + N-Methyl-2-pyrrolidone + 1-Hexanol + NaCl,+ KCl,or + KAc[J].Journal of Chemical & Engineering Data, 2008, 53(1):217-222 [9]STEPHENSON R M.Mutual solubilities: water-ketones,water-ethers,and water-gasoline-alcohols[J].Journal of Chemical & Engineering Data, 1992, 37(1):80-95 [10]DUARTE M M L, LOZAR J, MALMARY G, et al.Equilibrium diagrams at 19degree.C of water-malic acid-2-methyl-1-propanol,water-malic acid-1-pentanol,and water-malic acid-3-methyl-1-butanol ternary systems[J].Journal of Chemical & Engineering Data, 1989, 34(1):43-45 [11]LI A, ANDREN A W.Solubility of polychlorinated biphenyls in wateralcohol mixtures[J].Environmental Science & Technology, 1994, 28(1):47-52 [12]ASHOUR I.Liquid?Liquid Equilibrium of MTBE + Ethanol + Water and MTBE + 1-Hexanol + Water over the Temperature Range of 28815 to 308.15K[J].Journal of Chemical and Engineering Data, 2005, 50(1):113-118 [13]SENOL A.Phase Equilibria for Ternary Liquid Systems of (Water + Carboxylic Acid + 1-Heptanol) at 29315K: Modelling Considerations[J].Journal of Chemical Thermodynamics, 2004, 36(11):1007-1014 [14]AH A, KE W A, XIN X A, et al.Extraction of Allyl Alcohol from Its Aqueous Solution Using Two Different Ionic Liquids: Intermolecular Interaction and Liquid-liquid Phase Equilibrium Explorations[J].Journal of Molecular Liquids, 2021, 336(04):116875-116875 [15] 辛秀兰, 于洋, 侯松松, 等.一种拟薄水铝石和氧化铝的制备方法: CN201610891700.3[P]. 2017-07-14. [16]ROYER, DENNIS, HRITZ, et al.Process for producing alpha alumina monohydrate: US3419352[P]. 1968-12-31. [17]KAMLET M J, DOHERTY R M, ABRAHAM M H, et al.Important differences between aqueous solubility relationships for aliphatic and aromatic solutes[J].Journal of Physical Chemistry, 1987, 91(7):1996-2004 [18]王积涛.有机化学（第二版）[M]. 天津：南开大学出版社, 2003: 262-263. [19]程能林.溶剂手册（第四版）[M]. 北京：化学工业出版社, 2015: 385-414. [20]林兰, 张国亮, 孟琴, 等.用于醇–水体系分离技术的研究进展[J].化工进展, 2007, 3(1):360-365 [21]LITZEN D B, BOLGER S R.Isopropyl alcohol purification process: EP1987311204[P]. 1993-02-03. [22]DE GUIDO G, MONTICELLI C, SPATOLISANO E, et al.Separation of the Mixture 2-Propanol + Water by Heterogeneous Azeotropic Distillation with Isooctane as an Entrainer[J].Energies, 2021, 14(17):1-18 [23]HOOF V V, ABEELE L V D, BUEKENHOUDT A, et al.Economic comparison between azeotropic distillation and different hybrid systems combining distillation with pervaporation for the dehydration of isopropanol[J].Separation & Purification Technology, 2004, 37(1):33-49 [24]林军, 顾正桂.加碱萃取精馏制取无水乙醇[J].化学研究与应用, 2004, 16(2):282-283 [25]LIGERO E L, RAVAGNANI T M K.Dehydration of ethanol with salt extractive distillation—a comparative analysis between processes with salt recovery[J].Chemical Engineering & Processing Process Intensification, 2003, 42(7):543-552 [26]张志刚, 李治楠, 方荣丽, 等.萃取精馏分离叔丁醇- 水共沸物系萃取剂的选择[J].沈阳化工大学学报, 2018, 32(3):224-229 [27]王克良, 李静, 杨太飞, 等.基于离子液体的复合溶剂萃取精馏分离乙醇水溶液的研究[J].天然气化工, 2020, 45(4):87-93 [28] ZHANG Zhishan, ZHAO Xiaoxiao, WANG Yun, et al.Eco-efficient heat-integrated extractive distillation process using ionic liquid as entrainer for ethyl acetate-isopropyl alcohol-water mixture[J].Separation and Purification Technology, 2022, 287(287):120491-120491 [29] 陈水高, 吴祖燊, 戴品中.醇铝气相法制取纳米高纯氧化铝的方法: CN02138014.7[P]. 2003-05-07. [30]段启伟, 戴隆秀, 汪燮卿, 等.一种制备高纯氧化铝的方法: CN97104442.2[P]. 2000-05-17. [31]TANG Y T, CHEN Y W, HUANG H P, et al.Design of Reactive Distillations for Acetic Acid Esterification[J].AIChe Journal, 2005, 51(6):1683-1699 [32]蒋晓霄，丁金伟，洪凯伦，等.超重力精馏与反应耦合回收甲醇[J].现代化工, 2022, 42(06):225-226 [33]邱挺, 吴燕翔, 王良恩, 等.乙酸甲酯与甲醇共沸物催化精馏水解工艺[J].化工进展, 2007, 26(4):584-589 [34]张铁权, 臧立静, 黄克谨, 等.双隔壁反应精馏塔的设计与控制[J].现代化工, 2022, 42(03):221-226 [35] 徐涛.反应精馏塔的温控方法[J].化学工程与装备, 2020, 01(09):160-161 [36]于晓波，张吉波，蒋巍，等.分子筛膜的制备及其用于醇水分离的研究进展[J].现代化工, 2011, 31(12):22-28 [37] ZHANG H, YANG J, LI T, et al.Alkyl Chain Grafted-Reduced Graphene Oxide Membrane for Effective Separation of Water/Alcohol Miscible Mixtures[J].Frontiers in Chemistry, 2020, 8(01):598562-598562 [38]张在春, 王续宝.特殊精馏技术[J].山东化工, 2017, 46(7):81-84 [39]朱鋆珊, 马平, 郭丽.膜分离技术及其应用[J].当代化工, 2017, 46(6):1193-1195 [40]刘羊九, 王云山, 韩吉田, 等.膜蒸馏技术研究及应用进展[J].化工进展, 2018, 37(10):3726-3736 [41]IZQUIERDO-GIL M A, JONSSON G.Factors affecting flux and ethanol separation performance in vacuum membrane distillation (VMD)[J].Journal of Membrane Science, 2003, 214(1):113-130 [42]BANDINI S, GOSTOLI C, SARTI G C.Separation efficiency in vacuum membrane distillation[J].Journal of Membrane Science, 1992, 73(2-3):217-229 [43]BANDINI S, SAAVEDRA A, SARTI G C.Vacuum membrane distillation: Experiments and modeling[J].Aiche Journal, 2010, 43(2):398-408 [44]朱春燕, 赵之平, 刘殿忠, 等.膜蒸馏法分离低浓度乙醇水溶液的研究[C]. 第五届全国化学工程与生物化工年会, 西安, 2008. [45]LEE C H, HONG W H.Effect of operating variables on the flux and selectivity in sweep gas membrane distillation for dilute aqueous isopropanol[J].Journal of Membrane Science, 2001, 188(1):79-86 [46]RAUTENBACH R, ALBRECHT R.The separation potential of pervaporation: Part 2Process design and economics[J].Journal of Membrane Science, 1985, 25(1):25-54 [47]THI H, MIZSEY P, TOTH A J.Separation of Alcohol-Water Mixtures by a Combination of Distillation,Hydrophilic and Organophilic Pervaporation Processes[J].Membranes, 2020, 10(11):345-362 [48]THI H, SZILAGYI B, HAAZ E, et al.Optimization of Hybrid Distillation-hydrophilic and Organophilic Pervaporation Systems[J].Chemical Engineering Transactions, 2021, 86(1):1027-1032 [49]ZHANG J, HE Y, WANG Y P, et al.Synthesis of a self-supporting faujasite zeolite membrane using geopolymer gel for separation of alcohol/water mixture[J].Materials Letters, 2014, 116(1):167-170 [50]LECAROS R, VALBUENA R E, TAYO L L, et al.Tannin-based thin-film composite membranes integrated with nitrogen-doped graphene quantum dots for butanol dehydration through pervaporation[J].Journal of Membrane Science, 2021, 623(1):119077-119077 [51]LIU S, ZHOU G, GUAN K, et al.Dehydration of C2–C4 alcoholwater mixtures via electrostatically enhanced graphene oxide laminar membranes[J].AIChE Journal, 2021, 67(6):17170-17170 [52]DUBEY V, SAXENA C, SINGH L, et al.Pervaporation of binary water–ethanol mixtures through bacterial cellulose membrane[J].Separation & Purification Technology, 2002, 27(2):163-171 [53]南倩.氧化石墨烯复合膜的制备及其性能研究[D]. 北京: 北京化工大学, 2016. [54]ADAMS J A, KRULIK G A, BLATT C, et al.Dehydration and purification of isopropyl alcohol to an ultradry and ultrapure level: US08/691427[P]. 1999-02-09. [55]DUBEY V, SAXENA C, SINGH L, et al.Pervaporation of binary water–ethanol mixtures through bacterial cellulose membrane[J].Separation & Purification Technology, 2002, 27(2):163-171 [56]JONQUIèRES A, CLéMENT R, LOCHON P, et al.Industrial state-of-the-art of pervaporation and vapour permeation in the western countries[J].Journal of Membrane Science, 2002, 206(1):87-117 [57]YOSHIKAWA M, HIGUCHI A, ISHIKAWA M, et al.Vapor permeation of aqueous 2-propanol solutions through gelatinTorlon? poly(amide imide) blended membranes[J].Journal of Membrane Science, 2004, 243(1):89-95 [58]KANTI P, SRIGOWRI K, MADHURI J, et al.Dehydration of ethanol through blend membranes of chitosan and sodium alginate by pervaporation[J].Separation & Purification Technology, 2004, 40(3):259-266 [59]BHAT S D, NAIDU B V K, SHANBHAG G V, et al.Mesoporous molecular sieve (MCM-41)-filled sodium alginate hybrid nanocomposite membranes for pervaporation separation of water–isopropanol mixtures[J].Separation & Purification Technology, 2006, 49(1):56-63 [60]HUANG Z, SHI Y, WEN R, et al.Multilayer poly(vinyl alcohol)–zeolite 4A composite membranes for ethanol dehydration by means of pervaporation[J].Separation & Purification Technology, 2006, 51(2):126-136 [61]URTIAGA A M, GORRI E D, ORTIZ I.Pervaporative recovery of isopropanol from industrial effluents[J].Separation & Purification Technology, 2006, 49(3):245-252 [62]DOBRE T, PATRICHI C, PRYULESCU O C, et al.Pervaporation of Aqueous Ethanol Solutions through Rigid Composite Polyvinyl-AlcoholBacterial Cellulose Membranes[J].Processes, 2021, 9(3):437-450 [63]ACHARI D D, HEGDE S N, PATTANASHETTI N A, et al.Development of zeolite-A incorporated PVACS nanofibrous composite membranes using the electrospinning technique for pervaporation dehydration of watertert-butanol[J].New Journal of Chemistry, 2021, 45(8):3981-3996 [64]胡忠.利用膜分离技术回收正丁醇-水混合液的工艺研究[J].化工技术与开发, 1998, 3(27):12-15 [65]TSUYUMOTO M, TERAMOTO A, MEARES P.Dehydration of ethanol on a pilot-plant scale,using a new type of hollow-fiber membrane[J].Journal of Membrane Science, 1997, 133(1):83-94 [66]DHANUJA G, SMITHA B, SRIDHAR S.Pervaporation of isopropanol–water mixtures through polyion complex membranes[J].Separation & Purification Technology, 2005, 44(2):130-138 [67]杜广庆.生物丁醇的制备及分离耦合技术[D]. 大连: 大连理工大学, 2015. [68]关宇.气提/蒸汽渗透分离集成及PDMS/VTES膜的绿色制备研究[D]. 北京: 北京化工大学, 2015. [69]王彦锋.新型耦合分离技术生产燃料乙醇的研究[D]. 上海: 华南理工大学, 2005. [70]CUI P, ZHAO F, LIU X, et al.Sustainable wastewater treatment via PV-distillation hybrid process for the separation of ethyl acetateisopropanolwater[J].Separation and Purification Technology, 2021, 257(17):117919-117919 [71]HARVIANTO G R, AHMAD F, LE C N, et al.Vapor permeation–distillation hybrid processes for cost-effective isopropanol dehydration: modeling,simulation and optimization[J].Journal of Membrane Science, 2016, 497(2016):108-119 [72]GUAN Y, HU S, WANG Y, et al.Separating isopropanol from its diluted solutions via a process of integrating gas stripping and vapor permeation[J].RSC Advances, 2015, 5(31):24031-24037