Post-synthetic modification of CARDO-based materials: application in sour natural gas separation

Hayek, Ali; Alsamah, Abdulkarim; Yahaya, Garba O.; Qasem, Eyad A.; Alhajry, Rashed H.

doi:10.1039/d0ta06967a

Cited by 20 publications

(28 citation statements)

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“…CO 2 permeability–CO 2 /CH 4 selectivity relationship chart depicting the pure-gas permeation performance of poly(imide–oxadiazole) membranes compared to those of previously reported materials. Literature data refs − .…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2022

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The design of new polymeric materials and the search for new classes of polymers for industrial application in membrane-based gas separation have been the focus of several research groups worldwide. Membranes with high productivity and efficiency under harsh operational conditions of pressure and temperature during mixed-gas separation are of great interest. In this paper, we report the preparation of a series of block copolymers of poly(imide−oxadiazole)s built from 6FDA, Durene, and four different 1,3,4-oxadiazole-based monomers. The pureand mixed-gas separation properties of their corresponding membranes were measured. The mixed-gas separation data were collected at a high feed pressure of up to 900 psi. Such mixed-gas separation testing under harsh conditions is required to subject the membranes to environments similar to industrial use. For example, the mixed-gas CO 2 permeability of 6FDA-Durene/6FDA-4BAO(Me) (3:1) was measured at 900 psi to be ∼130 barrer, and the CO 2 /CH 4 selectivity is around ∼24. These results of permeability and selectivity of poly(imide−oxadiazole) membranes at such high gas feed pressure are considered very attractive and are superior to many glassy polymers reported in the literature and that are industrially observed membranes. This work illustrates well a case scenario of structure−property relationship and demonstrates the exclusivity of mixed-gas testing which could not be predicted from the ideal situation of pure-gas testing. In the near future, the mixed-gas separation properties of thin layer composite and hollow fibers will be evaluated.

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Section: Resultsmentioning

confidence: 99%

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

et al. 2022

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“…Hayek et al (2020) prepared a new polyimide with high yield using Friedel–Crafts alkylation by incorporating bulky tert ‐butyl groups to 6FDA–CARDO polyimide. [ 105 ] The modified 6FDA–CARDO(t‐Bu) polyimide exhibited enhanced CO 2 permeability (271 vs 58.9 Barrer) but lower CO 2 /CH 4 selectivity (18.6 vs 30.1) than the unsubstituted 6FDA–CARDO analogue. [ 105 ] Interestingly, 6FDA–CARDO(t‐Bu) showed a better performance when tested under high‐pressure five‐component mixed‐gas conditions (feed: N 2 /C 2 H 6 /CH 4 /CO 2 /H 2 S = 10/3/55/10/22 vol%).…”

Section: Development Of Novel Pim Materialsmentioning

confidence: 99%

“…[ 105 ] The modified 6FDA–CARDO(t‐Bu) polyimide exhibited enhanced CO 2 permeability (271 vs 58.9 Barrer) but lower CO 2 /CH 4 selectivity (18.6 vs 30.1) than the unsubstituted 6FDA–CARDO analogue. [ 105 ] Interestingly, 6FDA–CARDO(t‐Bu) showed a better performance when tested under high‐pressure five‐component mixed‐gas conditions (feed: N 2 /C 2 H 6 /CH 4 /CO 2 /H 2 S = 10/3/55/10/22 vol%). [ 105 ] For example, 6FDA–CARDO(t‐Bu) had a 3.2‐fold higher CO 2 and 3.8‐fold enhanced H 2 S permeability coupled with 10% higher H 2 S/CH 4 selectivity compared to 6FDA–CARDO polyimide under five‐component mixed‐gas conditions at 500 psi (34.5 bar) and 22 °C.…”

Section: Development Of Novel Pim Materialsmentioning

confidence: 99%

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Recent Progress on Polymers of Intrinsic Microporosity and Thermally Modified Analogue Materials for Membrane‐Based Fluid Separations

et al. 2021

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Solution‐processable amorphous glassy polymers of intrinsic microporosity (PIMs) are promising microporous organic materials for membrane‐based gas and liquid separations due to their high surface area and internal free volume, thermal and chemical stability, and excellent separation performance. This review provides an overview of the most recent developments in the design and transport properties of novel ladder PIM materials, polyimides of intrinsic microporosity (PIM–PIs), functionalized PIMs and PIM–PIs, PIM‐derived thermally rearranged (TR), and carbon molecular sieve (CMS) membrane materials as well as PIM‐based thin film composite membranes for a wide range of energy‐intensive gas and liquid separations. In less than two decades, PIMs have significantly lifted the performance upper bounds in H2/N2, H2/CH4, O2/N2, CO2/N2, and CO2/CH4 separations. However, PIMs are still limited by their insufficient gas‐pair selectivity to be considered as promising materials for challenging industrial separations such as olefin/paraffin separations. An optimum pore size distribution is required to further improve the selectivity of a PIM for a given application. Specific attention is given to the potential use of PIM‐based CMS membranes for energy‐intensive CO2/CH4, N2/CH4, C2H4/C2H6, and C3H6/C3H8 separations, and thin film composite membranes containing PIM motifs for liquid separations.

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“…In this regard, to obtain colorless and transparent PI films, several effective strategies have been adopted to inhibit charge transfer interactions . The anchoring of highly electronegative groups, such as fluorine or sulfone groups, could reduce the electron-donating ability of diamine and raise the electron level band gap; thus, the formation of CTCs is inhibited in PI polymer chains. , The common methods also include the introduction of unsymmetrical structures, , bulky side units, , and alicyclic moieties in PI polymers. , In the above methods, the molecular free volume among polymers was increased, and the stacking density of molecular chains was reduced significantly, which would effectively inhibit the formation of CTCs.…”

Section: Introductionmentioning

confidence: 99%

Polyimide Films Containing Trifluoromethoxy Groups with High Comprehensive Performance for Flexible Circuitry Substrates

Wang

Zhou

Feng

et al. 2022

ACS Appl. Polym. Mater.

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The outstanding overall performance of polyimide (PI) films is critical for their application in the microelectronic and optoelectronic industries. A series of novel PI films containing trifluoromethoxy groups were prepared from a 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA)/2,2′-bis (trifluoromethyl) biphenyl-4,4′-diamine (TFMB)/2,2′-bistrifluoromethoxy-biphenyl-4,4′-diamine (TFMOB) tri-copolymer in this paper. The comprehensive performances of the derived PI films could be modulated by the molar ratio of TFMOB/TFMB, and each performance of the PI films was explored in detail. All PI films exhibited excellent overall performance against PI-ref (PI films were prepared by PMDA and ODA in our lab, which referred to the raw materials of Kapton films), especially PI-30, which possessed the best performance, such as remarkable thermal stability (T 5% = 581 °C and T g = 368 °C), outstanding mechanical properties (T S = 195 MPa and T M = 3.5 GPa), ultralow moisture absorption (M a = 0.74%), lower dielectricity (D k = 2.877 and D f = 0.00815 at 10 GHz), and high optical transparency. In addition, PI-50 had the largest breaking elongation (E b = 27.6%), PI-70 had the lowest dielectric loss (D f = 0.00514), and PI-100 presented the lowest moisture absorption (M a = 0.50%). Each PI film possessed its own unique advantages to meet the special demand. Subsequently, the PI-30 film was used as a colorless and transparent substrate for flexible circuits, which could withstand multiple bends and still maintained excellent electrical performance after 1,40,000 folding times. The high comprehensive performance makes these PI films favorable candidates for flexible circuit substrates, foldable screens, and solar panels in the optoelectronic engineering and microelectronics industries.

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Post-synthetic modification of CARDO-based materials: application in sour natural gas separation

Abstract: A new homopolymer, 6FDA-CARDO(t-Bu), was prepared from 6FDA-CARDO through one-step chemical modification by adding bulky tert-butyl groups, using Friedel-Crafts alkylation. The incorporation of the bulky groups led to a significant...

Cited by 20 publications

References 64 publications

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

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

Recent Progress on Polymers of Intrinsic Microporosity and Thermally Modified Analogue Materials for Membrane‐Based Fluid Separations

Polyimide Films Containing Trifluoromethoxy Groups with High Comprehensive Performance for Flexible Circuitry Substrates

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