Fluorinated porous organic frameworks for C₂F₆/CF₄ gases separation

Abstract

As an indispensable raw material for silicon-based semiconductor industry, carbon tetrafluoride (CF₄) is widely used as plasma etching and cleaning gas in the manufacture of semiconductors. How to efficiently remove the C₂F₆ impurity during the CF₄ production process is a challenging task as semiconductor industry requires high-purity CF₄ gas. Herein, two fluorine-functionalized porous organic frameworks (F-POFs) named SPPOF-4F and SPPOF-8F were synthesized and used for separation of C₂F₆/CF₄ gases. Single-component gas adsorption experiments and ideal adsorbed solution theory (IAST) calculations indicate that two porous organic frameworks can selectively adsorb C₂F₆ from C₂F₆/CF₄ mixture. Molecular simulations have further complemented these experimental findings by revealing F-induced host-guest interactions between F-POFs and C₂F₆ at a molecular level. Additionally, dynamic breakthrough experiments verified that the F-POFs can capture C₂F₆ in C₂F₆/CF₄ mixture at practical conditions. These results indicate that F-POFs have great potential for application in the separation and purification of CF₄ electronic special gases.

Keywords

Porous organic framework / fluorine-functionalization / gases adsorption / adsorption separation / C₂F₆/CF₄

References

[1] Chang MB.Abatement of PFCs from semiconductor manufacturing processes by nonthermal plasma technologies:  a critical review.Ind Eng Chem Res2006;45:4101-9

[2] Donnelly VM.Review article: reactions of fluorine atoms with silicon, revisited, again.J Vac Sci Technol A Vac Surf Films2017;35:05C202

[3] Vorotyntsev AV,Trubyanov MM.Progress and perspectives in high-purity substance production for semiconductor industry.Rev Chem Eng2021;37:125-61

[4] Illuzzi F.Perfluorocompounds emission reduction by the semiconductor industry.J Integr Environ Sci2010;7:201-10

[5] World Semiconductor Trade Statistics. WSTS semiconductor market forecast fall 2023. Available from: https://www.wsts.org/76/103/WSTS-Semiconductor-Market-Forecast-Fall-2023. [Last accessed on 24 Jul 2024]

[6] Tang Z.The synthesis technology of high purity tetrafluoromethane by fluorine and carbon.Cryo Spec Gases2013;31:32-4. (in Chinese)

[7] Pashkevich DS,Petrov VB,Asovich VS.Synthesis of tetrafluoromethane by graphite fluorination with elemental fluorine.Russian J Appl Chem2004;77:92-7

[8] Pashkevich DS,Mukhortov DA,Alekseev YI.Synthesis of perfluoroalkanes by high-temperature reaction of graphite with fluorine in a fluidized bed.Russ J Appl Chem2004;77:1847-53

[9] Chen G. CN101298318A Method and apparatus for preparing high-purity carbon tetrafluoride gas. 2008. Available from: https://worldwide.espacenet.com/patent/search/family/040078304/publication/CN101298318A?q=CN101298318A. [Last accessed on 24 Jul 2024]

[10] Bao H. US5779863A Perfluoro compound (PFC) separation and purification method and system. 1997. Available from: https://worldwide.espacenet.com/patent/search/family/025129273/publication/US5779863A?q=US5779863A. [Last accessed on 24 Jul 2024]

[11] Asensio-Delgado S,Zarca G.Absorption separation of fluorinated refrigerant gases with ionic liquids: equilibrium, mass transport, and process design.Sep Purif Technol2021;276:119363

[12] Vorotyntsev VM,Vorotyntsev IV,Beljaev EM.The physico-chemical bases of separation and high purification of fluorocarbons and simple gases.Pet Chem2011;51:492-5

[13] Battisti R,Marangoni C.A background review on falling film distillation in wetted-wall columns: from fundamentals towards intensified technologies.Chem Eng Process Process Intensif2020;150:107873

[14] Ma H,Li Z.Research progress and optimization prospect of constant boiling distillation technology.E3S Web Conf2021;290:03025

[15] Wang H,Yang J.Docking of Cu^I and Ag^I in metal-organic frameworks for adsorption and separation of xenon.Angew Chem Int Ed Engl2021;60:3417-21

[16] Wu D,Yang G.Supramolecular control of MOF pore properties for the tailored guest adsorption/separation applications.Coord Chem Rev2021;434:213709

[17] Mukherjee S,Qazvini OT.Advances in adsorptive separation of benzene and cyclohexane by metal-organic framework adsorbents.Coord Chem Rev2021;437:213852

[18] Mohammed N,Islam MS.Selective adsorption and separation of organic dyes using functionalized cellulose nanocrystals.Chem Eng J2021;417:129237

[19] Ding Y,Moosa B.Selective adsorptive separation of cyclohexane over benzene using thienothiophene cages.Chem Sci2021;12:5315-8 PMCID:PMC8179544

[20] Lv D,Xu J.Recent advances in adsorptive separation of ethane and ethylene by C₂H₆-selective MOFs and other adsorbents.Chem Eng J2022;431:133208

[21] Gong W,Pham TD.Creating optimal pockets in a clathrochelate-based metal-organic framework for gas adsorption and separation: experimental and computational studies.J Am Chem Soc2022;144:3737-45

[22] Brandt P,Öztürk S,Liang J.Comparative evaluation of different MOF and non-MOF porous materials for SO₂ adsorption and separation showing the importance of small pore diameters for low-pressure uptake.Adv Sustain Syst2021;5:2000285

[23] Rehman A,Yop Rhee K.A rational design of cellulose-based heteroatom-doped porous carbons: promising contenders for CO₂ adsorption and separation.Chem Eng J2021;420:130421

[24] Xie W,Zhang J.The adsorptive separation of ethylene from C₂ hydrocarbons by metal-organic frameworks.Chemistry2023;29:e202300158

[25] Guo Y,Chen H.Hierarchical porous carbon with tunable apertures and nitrogen/oxygen heteroatoms for efficient adsorption and separation of VOCs.Chem Eng J2023;471:144558

[26] Ryu U,Rao PC.Recent advances in process engineering and upcoming applications of metal-organic frameworks.Coord Chem Rev2021;426:213544 PMCID:PMC7500364

[27] Lee JM.Advances in conjugated microporous polymers.Chem Rev2020;120:2171-214 PMCID:PMC7145355

[28] Ma Y,Rong H.Continuous porous aromatic framework membranes with modifiable sites for optimized gas separation.Angew Chem Int Ed Engl2022;61:e202113682

[29] Yuan Y.Porous aromatic frameworks as a platform for multifunctional applications.ACS Cent Sci2019;5:409-18 PMCID:PMC6439448

[30] Das S,Ben T.Porous organic materials: strategic design and structure-function correlation.Chem Rev2017;117:1515-63

[31] Bai R,Yan W.Low-energy adsorptive separation by zeolites.Natl Sci Rev2022;9:nwac064 PMCID:PMC9477195

[32] Peng X,Jin Q.Separation of CF₄/N₂, C₂F₆/N₂, and SF₆/N₂ mixtures in amorphous activated carbons using molecular simulations.ACS Appl Mater Interfaces2020;12:20044-55

[33] Sosa JE,Ribeiro RP.Adsorption of fluorinated greenhouse gases on activated carbons: evaluation of their potential for gas separation.J Chem Tech Biotech2020;95:1892-905

[34] Choi SW,Lee HJ,Lim D.CF₄ adsorption on porous carbon derived from silicon carbide.Microporous Mesoporous Mater2020;306:110373

[35] Zhu J,Xiao H.Aluminum-based metal organic frameworks for greenhouse gases CF₄ and C₂F₆ capture with excellent capacity and selectivity.Sep Purif Technol2024;331:125614

[36] Chuah CY,Bae TH.Hierarchically structured HKUST-1 nanocrystals for enhanced SF₆ capture and recovery.J Phys Chem C2017;121:6748-55

[37] Kim MB,Lee CY.High SF₆ selectivities and capacities in isostructural metal-organic frameworks with proper pore sizes and highly dense unsaturated metal sites.Microporous Mesoporous Mater2014;190:356-61

[38] Senkovska I,Navarro JAR.Adsorptive capturing and storing greenhouse gases such as sulfur hexafluoride and carbon tetrafluoride using metal-organic frameworks.Microporous Mesoporous Mater2012;156:115-20

[39] Kim M,Kim T.Highly selective adsorption of SF₆ over N₂ in a bromine-functionalized zirconium-based metal-organic framework.Chem Eng J2018;339:223-9

[40] Guo Y,Sun J,Zhang J.Porous activated carbons derived from waste sugarcane bagasse for CO₂ adsorption.Chem Eng J2020;381:122736

[41] Jiang N,Heijman SGJ.High-silica zeolites for adsorption of organic micro-pollutants in water treatment: a review.Water Res2018;144:145-61

[42] Xu X,Zhang Y.Ordered mesoporous alumina and their composites based on evaporation induced self-assembly for adsorption and catalysis.Chem Mater2020;32:3-26

[43] Wu J,Li S.Porous polymers as multifunctional material platforms toward task-specific applications.Adv Mater2019;31:e1802922

[44] Chaoui N,Dawson R,Thomas A.Trends and challenges for microporous polymers.Chem Soc Rev2017;46:3302-21

[45] Farha OK,Eryazici I.De novo synthesis of a metal-organic framework material featuring ultrahigh surface area and gas storage capacities.Nat Chem2010;2:944-8

[46] Comotti A,Bracco S.Fluorinated porous organic frameworks for improved CO₂ and CH₄ capture.Chem Commun2019;55:8999-9002

[47] Wu AX,Mizrahi Rodriguez K.Elucidating the role of fluorine content on gas sorption properties of fluorinated polyimides.Macromolecules2021;54:22-34

[48] Feng L,Zhong X.Fluorinated porous poly(spirobifluorene) via direct C-H arylation: characterization, porosity, and gas uptake.J Macromol Sci Part A2014;51:604-9

[49] Boopalachandran P.Vibrational spectra, structure, and theoretical calculations of 2-fluoro- and 3-fluoropyridine.Spectrochim Acta A Mol Biomol Spectrosc2011;79:1191-5

[50] Al-Ghouti MA.Guidelines for the use and interpretation of adsorption isotherm models: a review.J Hazard Mater2020;393:122383

[51] Bai X,Lu X.A fluorine induced enhancement of the surface polarization and crystallization of g-C₃N₄ for an efficient charge separation.New J Chem2021;45:9334-45

[52] Werner P,Asyuda A.Electron transfer dynamics and structural effects in benzonitrile monolayers with tuned dipole moments by differently positioned fluorine atoms.ACS Appl Mater Interfaces2020;12:39859-69