Zeolitic Imidazolate Framework ZIF‑71 for Adsorption and Separation of 2，3‑Butanediol/1，3‑Propanediol From Dilute Aqueous Solutions

doi:10.19894/j.issn.1000-0518.220043

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (11): 1735-1745.DOI: 10.19894/j.issn.1000-0518.220043

• Full Papers • Previous Articles Next Articles

Zeolitic Imidazolate Framework ZIF‑71 for Adsorption and Separation of 2，3‑Butanediol/1，3‑Propanediol From Dilute Aqueous Solutions

Jian-Shuang ZHANG, Mei-Zhen GAO, Meng-Yao WANG, Qi SHI(), Jin-Xiang DONG

Taiyuan University of Technology，Taiyuan 030024，China

Received:2022-02-21 Accepted:2022-05-19 Published:2022-11-01 Online:2022-11-09
Contact: Qi SHI
About author:shiqi594@163.com
Supported by:
the National Natural Science Foundation of China(21822808)

Abstract

Abstract:

1，3-Propanediol is an important chemical material， and the production of 1，3-propanediol by biological fermentation often produces 2，3-butanediol， which limits the further industrial application of bio-based 1，3-propanediol. 1，3-Propanediol and 2，3-butanediol have strong hydrophilicity， which makes it difficult to separate in low-concentration fermentation broth. ZIF-71 containing group —Cl （hydrophobicity and large polarizability） is selected to adsorb and separate 2，3-butanediol/1，3-propanediol from dilute aqueous solutions since 2，3-butanediol has a longer carbon chain and larger polarizability than 1，3-propanediol. The results show that the binary competitive adsorption capacity of ZIF-71 for 2，3-butanediol is 123.6 mg/g， the binary competitive separation selectivity for 2，3-butanediol/1，3-propanediol is up 7.6 and is better than Beta. In the three-cycle adsorption and desorption experiments， ZIF-71 still maintains a stable structure and selective adsorption for 2，3-butanediol. We reveal the separation mechanism of ZIF-71 for 1，3-propanediol and 2，3-butanediol through molecular simulation. The interaction between ZIF-71 and 1，3-propanediol is mainly through weak van der Waals force； while the interaction between ZIF-71 and 2，3-butanediol is through the synergistic effect of strong van der Waals force and weak hydrogen bonding， which causes the selective adsorption of 2，3-butanediol by ZIF-71. Therefore， ZIFs materials are expected to be candidate adsorbents for the selective adsorption and separation of by-product 2，3-butanediol from dilute aqueous solutions， which promotes the industrialization of biological production of 1，3-propanediol.

Key words: Zeolitic imidazolate frameworks, ZIF-71, Adsorption separation, 1, 3-Propanediol, 2, 3-Butanediol

CLC Number:

O647.3

Jian-Shuang ZHANG, Mei-Zhen GAO, Meng-Yao WANG, Qi SHI, Jin-Xiang DONG. Zeolitic Imidazolate Framework ZIF‑71 for Adsorption and Separation of 2，3‑Butanediol/1，3‑Propanediol From Dilute Aqueous Solutions[J]. Chinese Journal of Applied Chemistry, 2022, 39(11): 1735-1745.

Figures/Tables 11

Fig.1 Structural properties of solute molecules and water

Table 1 The molecular size， dipole moment and polarizability of solute molecules and water

溶质分子 ^a

Solute molecules

分子尺寸 ^b

Molecular size/nm³

偶极矩

Dipole moment/debye

极化率 ^d

Polarizability/nm³

H₂O

1，3?PDO

0.39×0.30×0.33

0.81×0.50×0.54

0.76×0.57×0.59

1.85^［29］

2.50^［30］

1.95 ^c

1.00×10^-3

6.79×10^-3

2，3?BDO

8.60×10^-3

Fig.2 Topology， composition， aperture and cage structure of ZIF-71［36］

Fig.3 （A） PXRD patterns of ZIF-71；（B） FT-IR characterization of ZIF-71；（C） TG curve of ZIF-71；（D） Particle size and morphology of ZIF-71 by SEM

Fig.4 N2 adsorption-desorption isotherm of ZIF-71 samples at 77 K （A） and pore size analysis （B）

Fig.5 The water vapor adsorption isotherm and contact angle of ZIF-71

Fig.6 Static adsorption isotherms of （A） ZIF-71 and （B） Beta for 1，3-PDO and 2，3-BDO and （C） comparison of static adsorption performance； Competitive adsorption isotherms of （D） ZIF-71 and （E） Beta for 1，3-PDO/2，3-BDO and （F） comparison of competitive adsorption performance

Fig.7 Adsorption breakthrough curves of binary-component 1，3-PDO （50 g/L） and 2，3-BDO （50 g/L） on ZIF-71

Fig.8 Simulated adsorption heats at infinite dilution for water， 1，3-PDO and 2，3-BDO adsorption in ZIF-71

Fig.9 Adsorption sites on ZIF-71 for water， 1，3-PDO and 2，3-BDO

Fig.10 （A） PXRD patterns of ZIF-71 during cyclic adsorption-desorption process and （B） adsorption/desorption capacity of 2，3-BDO in binary components 2，3-BDO/1，3-PDO （50 g/L， 50 g/L）

References 41

1	KURIAN J V. A new polymer platform for the future-sorona^® from corn derived 1，3-propanediol［J］. J Polym Environ， 2005， 13（2）： 159-167.
2	ZHU Y T， WANG Y X， GAO H， et al. Current advances in microbial production of 1，3-propanediol［J］. Biofuel Bioprod Bior， 2021， 15（5）： 1566-1583.
3	SUN Y Q， SHEN J T， YAN L， et al. Advances in bioconversion of glycerol to 1，3-propanediol： prospects and challenges［J］. Process Biochem， 2018， 71： 134-146.
4	余晓兰，汤建凯. 生物基聚对苯二甲酸丙二醇酯（PTT）纤维研究进展［J］. 精细与专用化学品， 2018， 26（2）： 13-17.
	YU X L， TANG J K. Research progress of bio-based polytrimethylene terephthalate （PTT） fibers［J］. Fine Speci Chem， 2018， 26（2）： 13-17.
5	周昱，姚洁，王公应. 1，3-丙二醇合成工艺研究进展［J］. 天然气化工， 2006， 31（1）： 66-74.
	ZHOU Y， YAO J， WANG G Y. Research progress on the synthesis process of 1，3-propanediol［J］. Nat Gas Chem Ind， 2006， 31（1）： 66-74.
6	LARI G M， PASTORE G， HAUS M， et al. Environmental and economical perspectives of a glycerol biorefinery［J］. Energ Environ Sci， 2018， 11（5）： 1012-1029.
7	LIU H J， ZHOU Y J， CAI Z Z， et al. 1，3-Propanediol fermentation with the by-product glycerol from biodiesel production by a genetic modified Klebsiella pneumoniae［J］. Adv Mater Res， 2012， 512-515： 323-329.
8	XU Y Z， GUO N N， ZHENG Z M， et al. Metabolism in 1，3-propanediol fed-batch fermentation by a D-lactate deficient mutant of klebsiella pneumoniae［J］. Biotechnol Bioeng， 2009， 104（5）： 965-972.
9	PARK J M， RATHNASINGH C， SONG H. Metabolic engineering of Klebsiella pneumoniae based on in silico analysis and its pilot-scale application for 1，3-propanediol and 2，3-butanediol co-production［J］. J Ind Microbiol Biotechnol， 2017， 44（3）： 431-441.
10	NAKAMURA C E， WHITED G M. Metabolic engineering for the microbial production of 1，3-propanediol［J］. Curr Opin Biotech， 2003， 14（5）： 454-459.
11	AMRAOUI Y， NARISETTY V， COULON F， et al. Integrated fermentative production and downstream processing of 2，3-butanediol from sugarcane bagasse-derived xylose by mutant strain of enterobacter ludwigii［J］. ACS Sustain Chem Eng， 2021， 9（30）： 10381-10391.
12	XIU Z L， ZENG A P. Present state and perspective of downstream processing of biologically produced 1，3-propanediol and 2，3-butanediol［J］. Appl Microbiol Biotechnol， 2008， 78（6）： 917-926.
13	CHEN T， CHEN Y Z， BAI P. Recovery of biomass-derived polyols by pressure swing adsorption： experiments， simulations， scale-up implementation and economic analysis［J］. Ind Eng Chem Res， 2020， 59（17）： 8323-8334.
14	MITREA L， LEOPOLD L F， BOUARI C， et al. Separation and purification of biogenic 1，3-propanediol from fermented glycerol through flocculation and strong acidic ion-exchange resin［J］. Biomolecules， 2020， 10（12）： 1601.
15	ZHANG C J， SHARMA S， WANG W， et al. A novel downstream process for highly pure 1，3-propanediol from an efficient fed-batch fermentation of raw glycerol by Clostridium pasteurianum［J］. Eng Life Sci， 2021， 21（6）： 351-363.
16	BASTRZYK J， GRYTA M， KARAKULSKI K. Fouling of nanofiltration membranes used for separation of fermented glycerol solutions［J］. Chem Pap， 2014， 68（6）： 757-765.
17	周雯，佟珊珊. 新型吸附材料分离和富集贵金属的研究进展［J］. 应用化学， 2021， 38（8）： 897-910.
	ZHOU W， TONG S S. Research progress on novel adsorbent materials for separation and enrichment of noble metals［J］. Chinese J Appl Chem， 2021， 38（8）： 897-910.
18	TAN S J， LIU L， CHEW J W. Competitive and synergistic adsorption of mixtures of polar and nonpolar gases in carbonaceous nanopores［J］. Langmuir， 2021， 37（22）： 6754-6764.
19	GUNZEL B， BERKE C H， ERNST S， et al. Adsorption von diolen aus fermentationsmedien an hydrophobe zeolithe［J］. Chem Ing Tech， 1990， 62（9）： 748-750.
20	SCHLIEKER H， GUNZEL B， DECKWER W D. Einsatz der adsorption zur produktabtrennung bei der glycerinvergarung zu 1，3-propandiol［J］. Chem Ing Tech， 1992， 64（8）： 727-728.
21	WANG Z， WU Z， TAN T W. Sorption equilibrium， mechanism and thermodynamics studies of 1，3-propanediol on beta zeolite from an aqueous solution［J］. Bioresour Technol， 2013， 145： 37-42.
22	苏建英，吴家鑫，谭天伟. 疏水硅沸石吸附1，3-丙二醇的研究［J］. 化学工程， 2007， 35（5）： 1-4.
	SU J Y， WU J X， TAN T W. Study on adsorption of 1，3-propanediol by hydrophobic silicalite［J］. Chem Eng，2007， 35（5）： 1-4.
23	LI G， LIU W， WANG X， et al. Separation of 2，3-butanediol using ZSM-5 zeolite modified with hydrophobic molecular spaces［J］. Chem Lett， 2014， 43（4）： 411-413.
24	PIMENTEL B R， PARULKAR A， ZHOU E K， et al. Zeolitic imidazolate frameworks： next-generation materials for energy-efficient gas separations［J］. ChemSusChem， 2014， 7（12）： 3202-3240.
25	CHEN F， LAI D， GUO L， et al. Deep desulfurization with record SO₂ adsorption on the metal-organic frameworks［J］. J Am Chem Soc， 2021， 143（24）： 9040-9047.
26	WANG Q， ASTRUC D. State of the art and prospects in metal-organic framework （MOF）-based and MOF-derived nanocatalysis［J］. Chem Rev， 2020， 120（2）： 1438-1511.
27	田龙，豆维新，杨玮婷，等. 不同尺寸ZIF-8对U（VI）的吸附性能［J］. 应用化学， 2021， 38（1）： 84-91.
	TIAN L， DOU W X， YANG W T， et al. Size effect of ZIF-8 on the adsorption of uranium［J］. Chinese J Appl Chem， 2021， 38（1）： 84-91
28	JIN H， LI Y S， YANG W S. Adsorption of biomass-derived polyols onto metal-organic frameworks from aqueous solutions［J］. Ind Eng Chem Res， 2018， 57（35）： 11963-11969.
29	LI J R， KUPPLER R J， ZHOU H C. Selective gas adsorption and separation in metal-organic frameworks［J］. Chem Soc Rev， 2009， 38（5）： 1477-1504.
30	徐如人，庞文琴，于吉红，等. 分子筛与多孔材料化学［M］. 北京：科学出版社， 2004： 204-205.
	XU R R， PANG W Q， YU J H， et al. Molecular sieves and porous materials chemistry［M］. Beijing： Science Press， 2004： 204-205.
31	JORGENSEN W L， CHANDRASEKHAR J， MADURA J D， et al. Comparison of simple potential functions for simulating liquid water［J］. J Chem Phys， 1983， 79（2）： 926-935.
32	WEE L H， VANDENBRANDE S， ROGGE S M J， et al. Chlorination of a zeolitic-imidazolate framework tunes packing and van der Waals interaction of carbon dioxide for optimized adsorptive separation［J］. J Am Chem Soc， 2021， 143（13）： 4962-4968.
33	ZHANG K， NALAPARAJU A， CHEN Y， et al. Biofuel purification in zeolitic imidazolate frameworks： the significant role of functional groups［J］. Phys Chem Chem Phys， 2014， 16（20）： 9643-9655.
34	WANG F， YANG H， KANG Y， et al. Guest selectivity of a porous tetrahedral imidazolate framework material during self-assembly［J］. J Mater Chem， 2012， 22（37）： 19732-19737.
35	PHAN A， DOONAN C J， URIBE-ROMO F J， et al. Synthesis， structure， and carbon dioxide capture properties of zeolitic imidazolate frameworks［J］. Acc Chem Res， 2010， 43（1）： 58-67.
36	BANERJEE R， PHAN A， WANG B， et al. High-throughput synthesis of zeolitic imidazolate frameworks and application to CO₂ capture［J］. Science， 2008， 319（5865）： 939-943.
37	Dassault Syst′emes BIOVIA， Materials studio modeling environment， release 2017， Dassault Systemes BIOVIA［CP］. San Diego， CA， 2016.
38	LIU S， LIU G， ZHAO X， et al. Hydrophobic-ZIF-71 filled PEBA mixed matrix membranes for recovery of biobutanol via pervaporation［J］. J Membr Sci， 2013， 446： 181-188.
39	MORTADA B， CHAPLAIS G， NOUALI H， et al. Phase transformations of metal-organic frameworks MAF-6 and ZIF-71 during intrusion-extrusion experiments［J］. J Phy Chem C， 2019， 123（7）： 4319-4328.
40	YOO D K， BHADRA B N， JHUNG S H. Adsorptive removal of hazardous organics from water and fuel with functionalized metal-organic frameworks： contribution of functional groups［J］. J Hazard Mater， 2021， 403： 123655.
41	ZHU Z， XU H， JIANG J， et al. Hydrophobic nanosized all-silica beta zeolite： efficient synthesis and adsorption application［J］. ACS Appl Mater Interfaces， 2017， 9（32）： 27273-27283.

[1]	Yu-Wen YANG, Jing-Yao QI, Lin LI, Guo-Ning CHU, Sai WANG, Yu ZHANG, Shuang ZHANG. Selective Oxidation of 5-Hydroxymethylfurfural to 2，5-Furandicarboxylic Acid over Ru Supported on Magnetic NiFe₂O₄ [J]. Chinese Journal of Applied Chemistry, 2023, 40(6): 879-887.
[2]	Ning YUAN, Jie MA, Jin-Ling ZHANG, Jian-Sheng ZHANG. Preparation of PCN-6（M） Bimetallic Organic Framework Materials by Steam-assisted Method and Their CO₂ and CH₄ Adsorption Performance [J]. Chinese Journal of Applied Chemistry, 2023, 40(6): 896-903.
[3]	Hai-Xiang XIU, Wan-Qiang LIU, Dong-Ming YIN, Yong CHENG, Chun-Li WANG, Li-Min WANG. Research Progress of AB₂ Laves Phase Hydrogen Storage Alloys [J]. Chinese Journal of Applied Chemistry, 2023, 40(5): 640-652.
[4]	Lin YANG, Hui PAN, Ding-Feng GAO, Xiao-Dong WANG. Preparation and Characterization of Nanocomposite Leather Finishing Agent Based on Aramid Modified Polymer [J]. Chinese Journal of Applied Chemistry, 2023, 40(5): 708-719.
[5]	Yu FANG, Wang-Qiang KUANG, Sheng-Ting KUANG, Wu-Ping LIAO. Selective Extraction and Recovery of Copper from the Leaching of Low-grade Copper Ore by H₂SO₄-NaCl Solution Using Cextrant 230 [J]. Chinese Journal of Applied Chemistry, 2023, 40(5): 758-768.
[6]	Mou-Cui LI, Yang-Ming DONG, Ying-Hui REN, Hai-Xia MA, Le QI. Synthesis， Antifungal Activity and Molecular Docking Study of 1，2，4-Triazole Bis-Schiff Base Derivatives [J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 116-125.
[7]	Yan-Qin CHENG, Zhuo-Xi LI, You-Di WANG, Juan-Juan XU, Zheng BIAN. Structurally Simplified 4-Hydroxyprolinamide for Highly Efficient Asymmetric Michael Addition of Aldehydes to Nitroolefins [J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 146-154.
[8]	Jia-Xin GUO, Yang LIU, Chang-Shan XU, Xiao-Nan LIU, Liang CHENG. The Changes of Mg²⁺ Mass Concentration in MgO NPs Suspension and Its Effects on the Growth of Wheat （Triticum aestivum L.） under Different pH [J]. Chinese Journal of Applied Chemistry, 2022, 39(9): 1401-1411.
[9]	En-Tong WANG, Lin-Fang YANG. Preparation and Properties of LiNi_0.6Co_0.2Mn_0.2O₂ Cathode Material for High Specific Capacity Lithium Ion Battery [J]. Chinese Journal of Applied Chemistry, 2022, 39(8): 1209-1215.
[10]	Bing WANG, Min TANG, Ying WANG, Zhi-Guang LIU. Preparation of Y₂O₃⁃Dopped SiC Ceramics by Micro⁃oxidation Sintering and Removal of Cd²⁺ in Mimic Wastewater [J]. Chinese Journal of Applied Chemistry, 2022, 39(8): 1312-1318.
[11]	Xue-Xian YANG, Jian ZHANG, Zhi-Gang GU. Surface‑Coordinated Metal‑Organic Framework Thin Film HKUST‑1 for Optoelectronic Applications [J]. Chinese Journal of Applied Chemistry, 2022, 39(7): 1013-1025.
[12]	Wang LI. Morphology Control and Catalytic Dehydrogenation Performance of Zeolitic Imidazolate Frameworks⁃8 [J]. Chinese Journal of Applied Chemistry, 2022, 39(7): 1065-1072.
[13]	Xiao-Li ZHANG, Yu-Mei PENG, Qing-Wei WANG, Li-Xia QIN, Xiao-Xia LIU, Shi-Zhao KANG, Xiang-Qing LI. Construction of Nano Ag Modified TiO₂Nanotube Array Substrate for Surface Enhanced Raman Scattering Detection and Degradation of Tetracycline Hydrochloride [J]. Chinese Journal of Applied Chemistry, 2022, 39(7): 1147-1156.
[14]	Chao ZHANG. Research Prospect of Single Atom Catalysts Towards Electrocatalytic Reduction of Carbon Dioxide [J]. Chinese Journal of Applied Chemistry, 2022, 39(6): 871-887.
[15]	Qin YANG, Ning-Hua CHEN, Yu-Jie ZHANG, Zhi-Xiang YE, Ying-Chun YANG. Preparation of Cerium Zirconium Composite Oxide Modified Glassy Carbon Electrode and the Detection of Pb²⁺ in Water Samples [J]. Chinese Journal of Applied Chemistry, 2022, 39(6): 990-999.

Zeolitic Imidazolate Framework ZIF‑71 for Adsorption and Separation of 2，3‑Butanediol/1，3‑Propanediol From Dilute Aqueous Solutions

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 11

References 41

Related Articles 15

Recommended Articles

Metrics

Comments