Molecular Design of Poly(imide–oxadiazole) Membranes for High-Pressure Mixed-Gas Separation

Hayek, Ali; Alsamah, Abdulkarim; Shalabi, Yasser A.; Saleem, Qasim; Sultan, Melhan M. Ben; Alhajry, Rashed H.

doi:10.1021/acs.macromol.2c00650

Cited by 11 publications

(6 citation statements)

References 78 publications

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“…For all studied copolyimides in this work, the permeability coefficients ( P ) followed the same general trend observed for most glassy polymeric membranes reported in our previous works: − P CO 2 > P N 2 > P CH 4 . This observation is mainly attributed to the difference in the kinetic diameters of the measured gases: CO 2 (3.30 Å) < N 2 (3.64 Å) < CH 4 (3.80 Å).…”

Section: Resultssupporting

confidence: 87%

Modified CARDO-Based Copolyimides with Improved Sour Mixed-Gas Permeation Properties

Hayek

Alsamah

Saleem

et al. 2022

ACS Appl. Polym. Mater.

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Chemical modification is an interesting tool to introduce functional groups into polymers’ backbones to tailor their properties in a desired fashion. Polymers used in membrane-based gas separation applications need to possess high gas permeability and selectivity during mixed-gas separation under harsh operational conditions of pressure and temperature. Herein, we report the modification of three copolyimides containing the moiety 9,9-bis(4-aminophenyl)fluorine (CARDO) through Friedel–Crafts alkylation to introduce bulky tert-butyl groups into their backbones. Membranes prepared from the modified polymers were evaluated using pure- and sweet mixed-gas under aggressive feed pressures. Based on the promising results obtained, a selected copolyimide was subjected to sour mixed-gas separation under feed pressures up to 500 psi. Mixed-gas separation studies, especially those containing hydrogen sulfide, are of great interest to develop membranes for use in sour natural gas reserve treatment. For example, the H2S and CO2 permeability coefficients of 6FDA-Durene/6FDA-CARDO(t-Bu) at 500 psi were recorded as 456 and 238 Barrer, respectively, where the H2S/CH4 and CO2/CH4 are 20.4 and 10.6, respectively. The obtained results are very promising and even superior to many glassy polymers reported previously. This work represents an example of the benefit of chemical modification on polymers to tailor their structure–property relationship. Future works will be focused on the fabrication and testing of asymmetric or composite hollow fibers to imitate the membrane modules used industrially.

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Section: Resultssupporting

confidence: 87%

Modified CARDO-Based Copolyimides with Improved Sour Mixed-Gas Permeation Properties

Hayek

Alsamah

Saleem

et al. 2022

ACS Appl. Polym. Mater.

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“…Alternatively, another strategy to incorporate functions into membrane matrices is mixing polymeric materials with other active additives. [ 81‐83 ] For example, Sun and colleagues reported the preparation of a highly crystalline asymmetric MOF (HKUST‐1) hybrid membrane as a gaseous stimulation actuator with fast response. PPMs with gradient porous structure served as both reactive template and precursor.…”

Section: Electrostatic Complex‐induced Phase Separation Methods For S...mentioning

confidence: 99%

Functional Poly(ionic liquid) Porous Membranes: From Fabrications to Advanced Applications^†

Wang

et al. 2022

Chin. J. Chem.

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Comprehensive Summary Polyelectrolyte porous membranes (PPMs) belong to the most interesting classes of materials, because the synergy of tunable pore sizes and charge nature of polyelectrolyte endow them with wide‐ranging practical applications. However, owing to the water solubility and ionic nature of the polyelectrolytes, traditional polyelectrolytes are difficult to use in scalable preparation of high‐quality PPMs through the well‐developed industrial methods. Poly(ionic liquid)s (PIL) are a subclass of functional polyelectrolytes bearing ionic liquid groups in their repeating unites, inheriting the advantages of ionic liquids (ILs) and macromolecular architecture features. In recent years, along with rapid development of PIL materials chemistry, considerable and significant developments involving the novel preparation methods, and structure‐property‐function relationships of PPMs have been made. In this review, we highlight the latest discovery and proceedings of PPMs, particularly the advancements in how to tailor structures and properties of PPMs by rational structure design of PILs. The formation mechanisms of various PPMs were also discussed in detail from the viewpoint of PILs molecular structures. A future perspective of the challenges and promising potential of PPMs is cast on the basis of these achievements. We expect that these analyses and deductions will be useful for the design of useful PPMs and serve as a source of inspiration for the design of future multifunctional PPMs.

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“…The block copolyimide 6FDA-Durene/CARDO(OH) (3:1) was prepared from the following three monomers: 6FDA [4,4′-(hexafluoroisopropylidene)diphthalic anhydride], Durene (2,3,5,6-tetramethylbenzene-1,4-diamine), and CARDO(OH) [9,9-bis(4-aminophenyl)-9 H -fluorene-2,7-diol]. Polymeric membranes prepared from 6FDA-based copolyimides and containing the Durene moiety have shown great performance for mixed-gas separation in challenging environments. ,− The CARDO(OH) monomer is a derivative of the CARDO monomer [9,9-bis(4-aminophenyl)fluorene], which was studied thoroughly by our group. ,,,, Interestingly, the chemical structure of CARDO(OH) includes two hydroxyl groups located at the 2 and 7 positions of its fluorene moiety. These hydroxyl groups can act as (1) bulky groups within the polymer backbone to enhance the diffusion of gas molecules [i.e., V W of CARDO = 321.6 Å 3 and V W of CARDO(OH) = 338.5 Å 3 ], (2) polar groups to increase the gas-polymer interaction (i.e., higher solubility), and (3) sites for thermal cross-linking.…”

Section: Introductionmentioning

confidence: 99%

Enhanced High-Pressure Mixed-Gas Sieving Properties of Thermally Cross-Linked Polyimide Membranes

Hayek,

Alsamah,

Saleem

et al. 2024

ACS Appl. Polym. Mater.

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Polymeric membranes are susceptible to aging and plasticization, which alters their separation properties since polymeric chain mobility within the membrane matrix is greatly affected. Hence, the implementation of these materials in industrial applications has been limited. However, cross-linking of polymeric membranes is a robust methodology to enhance their physical and mechanical properties. In this regard, thermal cross-linking is advantageous over chemical cross-linking since it could be applied directly to membranes without the addition of exogenous reagents. In this paper, we report the synthesis of a CARDO(OH)-containing copolyimide, amenable to thermal cross-linking due to the hydroxyl groups within the CARDO(OH) monomer. Membranes prepared from the 6FDA-Durene/CARDO(OH) (3:1) copolyimide underwent thermal cross-linking at 200 °C for varying durations (up to 96 h), and their pure- and mixed-gas separation performances were assessed. The mixed-gas studies were conducted under aggressive conditions of high feed pressures (20.7–62.0 bar) and operational temperatures (25–55 °C), aimed to closely simulate real-world scenarios for natural gas purification. Notably, the thermally cross-linked 6FDA-Durene/CARDO(OH) (3:1) for 96 h exhibited a mixed-gas CO2 permeability coefficient of 219 Barrer and a CO2/CH4 selectivity of 26.1 at 34.5 bar and 45 °C. Moreover, the membrane did not show any sign of plasticization under elevated feed pressures of up to 62.0 bar. This work demonstrates the effectiveness of thermal cross-linking in developing high-performance polymeric membranes under realistic conditions of pressure and temperature. Upcoming research endeavors will concentrate on creating and evaluating hollow fiber modules, aiming to replicate similar morphologies employed in industrial applications.

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Molecular Design of Poly(imide–oxadiazole) Membranes for High-Pressure Mixed-Gas Separation

Cited by 11 publications

References 78 publications

Modified CARDO-Based Copolyimides with Improved Sour Mixed-Gas Permeation Properties

Modified CARDO-Based Copolyimides with Improved Sour Mixed-Gas Permeation Properties

Functional Poly(ionic liquid) Porous Membranes: From Fabrications to Advanced Applications^†

Enhanced High-Pressure Mixed-Gas Sieving Properties of Thermally Cross-Linked Polyimide Membranes

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Molecular Design of Poly(imide–oxadiazole) Membranes for High-Pressure Mixed-Gas Separation

Cited by 11 publications

References 78 publications

Modified CARDO-Based Copolyimides with Improved Sour Mixed-Gas Permeation Properties

Modified CARDO-Based Copolyimides with Improved Sour Mixed-Gas Permeation Properties

Functional Poly(ionic liquid) Porous Membranes: From Fabrications to Advanced Applications†

Enhanced High-Pressure Mixed-Gas Sieving Properties of Thermally Cross-Linked Polyimide Membranes

Contact Info

Product

Resources

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Functional Poly(ionic liquid) Porous Membranes: From Fabrications to Advanced Applications^†