Crosslinking of Branched PIM-1 and PIM-Py Membranes for Recovery of Toluene from Dimethyl Sulfoxide by Pervaporation

Sulaiman Aloraini; Michael Mathias; Jessica Crone; Kurtis Bryce; Ming Yu; Richard A. Kirk; Mohd Zamidi Ahmad; Edidiong D. Asuquo; Sandra Rico-Martinez; Alexey V. Volkov; Andrew B. Foster; Peter M. Budd

doi:10.1021/acsapm.2c01600

Crosslinking of Branched PIM-1 and PIM-Py Membranes for Recovery of Toluene from Dimethyl Sulfoxide by Pervaporation

Sulaiman Aloraini, Michael Mathias, Jessica Crone, Kurtis Bryce, Ming Yu, Richard A. Kirk, Mohd Zamidi Ahmad, Edidiong D. Asuquo, Sandra Rico-Martinez, Alexey V. Volkov, Andrew B. Foster, Peter M. Budd

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10 Scopus citations

Abstract

Branched forms of the archetypal polymer of intrinsic microporosity PIM-1 and the pyridinecarbonitrile-containing PIM-Py may be crosslinked under ambient conditions by palladium(II) acetate. Branched PIM-1 can arise in polymerizations of 5,5′,6,6′-tetrahydroxy-3,3,3′,3′-tetramethyl-1,1′-spirobisindane with tetrafluoroterephthalonitrile conducted at a high set temperature (160 °C) under conditions, such as high dilution, that lead to a lower-temperature profile over the course of the reaction. Membranes of PIM-1 and PIM-Py crosslinked with palladium acetate are sufficiently stable in organic solvents for use in the recovery of toluene from its mixture with dimethyl sulfoxide (DMSO) by pervaporation at 65 °C. With both PIM-1 and PIM-Py membranes, pervaporation gives high toluene/DMSO separation factors (around 10 with a 77 vol % toluene feed). Detailed analysis shows that the membranes themselves are slightly selective for DMSO and it is the high driving force for toluene evaporation that drives the separation.

Original language	English (US)
Pages (from-to)	1145-1158
Number of pages	14
Journal	ACS Applied Polymer Materials
Volume	5
Issue number	2
DOIs	https://doi.org/10.1021/acsapm.2c01600
State	Published - Jan 17 2023
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2023-03-06
Acknowledgements: This work was supported by a British Council Institutional Links grant, No. 351983438 0100 “Development of a membrane method for the recovery of aromatic hydrocarbons from their mixtures with polar solvents” and by EPSRC Programme Grant ep/v047078/1 “SynHiSel”. S.A. is sponsored by Qassim University, Saudi Arabia. M.Y. is grateful for a Manchester–Melbourne dual award PhD studentship funded by the University of Melbourne. E.D.A. was supported by EPSRC grant EP/M001342/1. S.R.-M. received funding through the University of Valladolid Erasmus+ mobility for traineeship scheme and the Spanish Ministry of Sciences, Innovation and Universities (MCIU) FPU grant. The authors thank Anne Davies and Martin Jennings for their assistance in obtaining the elemental analysis. They also thank Carole Webb for her help with the GC analysis. The authors are grateful to Dr. Pavel Izák, Institute of Chemical Process Fundamentals, Prague, Czech Republic, for the design of the pervaporation cell.

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10.1021/acsapm.2c01600

https://repository.kaust.edu.sa/bitstream/10754/689989/1/acsapm.2c01600.pdf

Cite this

Aloraini, S., Mathias, M., Crone, J., Bryce, K., Yu, M., Kirk, R. A., Ahmad, M. Z., Asuquo, E. D., Rico-Martinez, S., Volkov, A. V., Foster, A. B., & Budd, P. M. (2023). Crosslinking of Branched PIM-1 and PIM-Py Membranes for Recovery of Toluene from Dimethyl Sulfoxide by Pervaporation. ACS Applied Polymer Materials, 5(2), 1145-1158. https://doi.org/10.1021/acsapm.2c01600

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title = "Crosslinking of Branched PIM-1 and PIM-Py Membranes for Recovery of Toluene from Dimethyl Sulfoxide by Pervaporation",

abstract = "Branched forms of the archetypal polymer of intrinsic microporosity PIM-1 and the pyridinecarbonitrile-containing PIM-Py may be crosslinked under ambient conditions by palladium(II) acetate. Branched PIM-1 can arise in polymerizations of 5,5′,6,6′-tetrahydroxy-3,3,3′,3′-tetramethyl-1,1′-spirobisindane with tetrafluoroterephthalonitrile conducted at a high set temperature (160 °C) under conditions, such as high dilution, that lead to a lower-temperature profile over the course of the reaction. Membranes of PIM-1 and PIM-Py crosslinked with palladium acetate are sufficiently stable in organic solvents for use in the recovery of toluene from its mixture with dimethyl sulfoxide (DMSO) by pervaporation at 65 °C. With both PIM-1 and PIM-Py membranes, pervaporation gives high toluene/DMSO separation factors (around 10 with a 77 vol % toluene feed). Detailed analysis shows that the membranes themselves are slightly selective for DMSO and it is the high driving force for toluene evaporation that drives the separation.",

author = "Sulaiman Aloraini and Michael Mathias and Jessica Crone and Kurtis Bryce and Ming Yu and Kirk, {Richard A.} and Ahmad, {Mohd Zamidi} and Asuquo, {Edidiong D.} and Sandra Rico-Martinez and Volkov, {Alexey V.} and Foster, {Andrew B.} and Budd, {Peter M.}",

note = "KAUST Repository Item: Exported on 2023-03-06 Acknowledgements: This work was supported by a British Council Institutional Links grant, No. 351983438 0100 “Development of a membrane method for the recovery of aromatic hydrocarbons from their mixtures with polar solvents” and by EPSRC Programme Grant ep/v047078/1 “SynHiSel”. S.A. is sponsored by Qassim University, Saudi Arabia. M.Y. is grateful for a Manchester–Melbourne dual award PhD studentship funded by the University of Melbourne. E.D.A. was supported by EPSRC grant EP/M001342/1. S.R.-M. received funding through the University of Valladolid Erasmus+ mobility for traineeship scheme and the Spanish Ministry of Sciences, Innovation and Universities (MCIU) FPU grant. The authors thank Anne Davies and Martin Jennings for their assistance in obtaining the elemental analysis. They also thank Carole Webb for her help with the GC analysis. The authors are grateful to Dr. Pavel Iz{\'a}k, Institute of Chemical Process Fundamentals, Prague, Czech Republic, for the design of the pervaporation cell.",

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doi = "10.1021/acsapm.2c01600",

language = "English (US)",

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T1 - Crosslinking of Branched PIM-1 and PIM-Py Membranes for Recovery of Toluene from Dimethyl Sulfoxide by Pervaporation

AU - Aloraini, Sulaiman

AU - Mathias, Michael

AU - Crone, Jessica

AU - Bryce, Kurtis

AU - Yu, Ming

AU - Kirk, Richard A.

AU - Ahmad, Mohd Zamidi

AU - Asuquo, Edidiong D.

AU - Rico-Martinez, Sandra

AU - Volkov, Alexey V.

AU - Foster, Andrew B.

AU - Budd, Peter M.

N1 - KAUST Repository Item: Exported on 2023-03-06 Acknowledgements: This work was supported by a British Council Institutional Links grant, No. 351983438 0100 “Development of a membrane method for the recovery of aromatic hydrocarbons from their mixtures with polar solvents” and by EPSRC Programme Grant ep/v047078/1 “SynHiSel”. S.A. is sponsored by Qassim University, Saudi Arabia. M.Y. is grateful for a Manchester–Melbourne dual award PhD studentship funded by the University of Melbourne. E.D.A. was supported by EPSRC grant EP/M001342/1. S.R.-M. received funding through the University of Valladolid Erasmus+ mobility for traineeship scheme and the Spanish Ministry of Sciences, Innovation and Universities (MCIU) FPU grant. The authors thank Anne Davies and Martin Jennings for their assistance in obtaining the elemental analysis. They also thank Carole Webb for her help with the GC analysis. The authors are grateful to Dr. Pavel Izák, Institute of Chemical Process Fundamentals, Prague, Czech Republic, for the design of the pervaporation cell.

PY - 2023/1/17

Y1 - 2023/1/17

N2 - Branched forms of the archetypal polymer of intrinsic microporosity PIM-1 and the pyridinecarbonitrile-containing PIM-Py may be crosslinked under ambient conditions by palladium(II) acetate. Branched PIM-1 can arise in polymerizations of 5,5′,6,6′-tetrahydroxy-3,3,3′,3′-tetramethyl-1,1′-spirobisindane with tetrafluoroterephthalonitrile conducted at a high set temperature (160 °C) under conditions, such as high dilution, that lead to a lower-temperature profile over the course of the reaction. Membranes of PIM-1 and PIM-Py crosslinked with palladium acetate are sufficiently stable in organic solvents for use in the recovery of toluene from its mixture with dimethyl sulfoxide (DMSO) by pervaporation at 65 °C. With both PIM-1 and PIM-Py membranes, pervaporation gives high toluene/DMSO separation factors (around 10 with a 77 vol % toluene feed). Detailed analysis shows that the membranes themselves are slightly selective for DMSO and it is the high driving force for toluene evaporation that drives the separation.

AB - Branched forms of the archetypal polymer of intrinsic microporosity PIM-1 and the pyridinecarbonitrile-containing PIM-Py may be crosslinked under ambient conditions by palladium(II) acetate. Branched PIM-1 can arise in polymerizations of 5,5′,6,6′-tetrahydroxy-3,3,3′,3′-tetramethyl-1,1′-spirobisindane with tetrafluoroterephthalonitrile conducted at a high set temperature (160 °C) under conditions, such as high dilution, that lead to a lower-temperature profile over the course of the reaction. Membranes of PIM-1 and PIM-Py crosslinked with palladium acetate are sufficiently stable in organic solvents for use in the recovery of toluene from its mixture with dimethyl sulfoxide (DMSO) by pervaporation at 65 °C. With both PIM-1 and PIM-Py membranes, pervaporation gives high toluene/DMSO separation factors (around 10 with a 77 vol % toluene feed). Detailed analysis shows that the membranes themselves are slightly selective for DMSO and it is the high driving force for toluene evaporation that drives the separation.

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UR - https://pubs.acs.org/doi/10.1021/acsapm.2c01600

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U2 - 10.1021/acsapm.2c01600

DO - 10.1021/acsapm.2c01600

M3 - Article

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SN - 2637-6105

VL - 5

SP - 1145

EP - 1158

JO - ACS Applied Polymer Materials

JF - ACS Applied Polymer Materials

IS - 2

ER -

Crosslinking of Branched PIM-1 and PIM-Py Membranes for Recovery of Toluene from Dimethyl Sulfoxide by Pervaporation

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