Reverse selective glassy polymers for C3+ hydrocarbon recovery from natural gas

Vaughn, Justin T.; Harrigan, Daniel J.; Sundell, Benjamin J.; Lawrence, John; Yang, John Y.

doi:10.1016/j.memsci.2016.09.003

Cited by 45 publications

(20 citation statements)

References 9 publications

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“…A few years ago it was shown that similar effect can be achieved by the introduction of the Si-O-C-containing groups as side substituents in the metathesis polynorbornenes ( Fig. 23) [58,107,127]. The selectivity of butane/methane separation (α(C 4 /C 1 )) was up to 21.5.…”

Section: Approaches To the Production Of Siliconcontaining Polynorbormentioning

confidence: 93%

“…The selectivity of butane/methane separation (α(C 4 /C 1 )) was up to 21.5. The presence of side substituents with the flexible Si-O-C or Si-O-Si bonds improved the selectivity of separation of hydrocarbons or CO 2 /N 2 mixtures not only for the metathesis polynorbornenes but also for the addition polymers [58,69,97,107,[127][128]. This approach can be considered as a new tool for the macromolecular design of high performance membrane materials for gas separation.…”

Section: Approaches To the Production Of Siliconcontaining Polynorbormentioning

confidence: 98%

“…A combination of the versatile routes of norbornene synthesis with different ways of their polymerization makes the macromolecular design of norbornene polymers with the desired properties very promising. From the end of the last century until now, a large variety of polynorbornenes bearing alkyl [56-57], silyl [8,[58][59], germyl [60][61][62], fluoro [63][64][65], chloro [64] or imido [66][67][68] groups were tested for the gas transport properties. The results obtained were used for the design and directed synthesis of highly gas permeable polymer materials from norbornenes.…”

Section: Introductionmentioning

confidence: 99%

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Macromolecular Design and Synthesis of Polymers from Silicon- Containing Norbornenes for Membrane Gas Separation

Бермешев¹,

Финкельштейн²

2018

INEOS OPEN

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The present review highlights recent approaches to the synthesis of highly permeable polymers by metathesis and addition polymerization of silicon-containing norbornenes. The main focus is on the authors' own works that utilize Me 3 Sisubstituted exo-tricyclononenes as highly reactive norbornenetype monomers for polymerization. The basic relationships between polymer structures and their gas permeability characteristics are considered. The possibility of tuning the gas transport properties of polymers (permeability and selectivity) by modification of their structures is shown. (M. V.Bermeshev)

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Section: Approaches To the Production Of Siliconcontaining Polynorbormentioning

confidence: 93%

Section: Approaches To the Production Of Siliconcontaining Polynorbormentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Macromolecular Design and Synthesis of Polymers from Silicon- Containing Norbornenes for Membrane Gas Separation

Бермешев¹,

Финкельштейн²

2018

INEOS OPEN

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“…Therefore, the process of hydrocarbon separation would be improved if the separation selectivity and polymers stability could be enhanced. To overcome these problems, low free volume glassy polynorbornenes and polyacetylenes have been successfully developed. The solubility‐controlled permeation of hydrocarbons in these polymers was due to the presence of flexible rubbery‐like moieties (e.g., SiOSi or SiOC) in side substituents.…”

Section: Methodsmentioning

confidence: 99%

Addition Polyalkylnorbornenes: A Promising New Class of Si‐Free Membrane Materials for Hydrocarbons Separation

Wozniak

Bermesheva

Borisov

et al. 2019

Macromol. Rapid Commun.

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ated petroleum gases. The realization of this process allows avoiding problems with the condensation of hydrocarbons (i.e., to reduce the dew point) and pre-detonating coking in compressor engines. [4,5] The separated C 2+ fraction will be a valuable feed for further chemical processing, or it can be used as a fuel. For a successful solution of the abovementioned task, membranes that show solubilitycontrolled permeation (i.e., which are characterized by higher permeability of heavier components of a mixture) seem to be the most attractive. For a long time, it was believed that the solubility-controlled permeation is a feature of rubbery polymers. In particular, it took place for the most permeable rubber-polydimethylsiloxane, while for convenient glassy polymers the permeability of hydrocarbons usually reduces with the size of penetrants mole cules. [5,6] At the same time, the use of glassy polymers in this process could extend frames and conditions of its application owing to high glass transition temperatures, good mechanical properties, and the promising combination of membrane characteristics of glassy polymers (glassy polymers dominate the polymers near or on the upper bound in contrast to rubbery polymers [7] ). The discovery of glassy poly(trimethylsilylpropyne) (PTMSP) and other highly permeable polyacetylenes in the last decades of the twentieth century quite unexpectedly revealed that glassy polymers indeed could possess the solubility controlled gas permeation of hydrocarbons. [8,9] Later it was shown that some other glassy polymers with large free volume polymers of intrinsic microporosity (PIM's) [10,11] and addition polynorbornenes bearing Me 3 Si-side groups [12,13] ) also exhibited the solubility controlled permeation. The main reasons for this phenomenon were the nanoporous nature of these glassy polymers and the presence of large free volume. Unfortunately, the abovementioned nanoporous polymers have not found a practical application for separation of hydrocarbons mainly due to the significant aging over time. These materials, as well as polysiloxanes, are extremely permeable membranes, so higher permeable polymers are not apparently required. Therefore, the process of hydrocarbon separation would be improved if the separation selectivity and polymers stability could be enhanced. To overcome these problems, low free volume glassy polynorbornenes [14][15][16][17] and polyacetylenes [18][19][20] have been successfully developed. The solubility-controlled permeation of hydrocarbons in these polymers Addition Poly(alkylnorbornenes) Nanoporous glassy polymers are perspective materials for the fabrication of gas separation membranes, especially for the application of gaseous hydrocarbon separation. However, the drawback of such materials is the pronounced physical aging resulting in the dramatic drop of gas transport properties due to relaxation of high-free-volume fraction in time. Herein, a novel and readily available group of such glassy polymers is reported based on 5-alkylnorbornenes. These polym...

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“…In this case, the different influence on gas‐transport characteristics can be observed depending on the nature of a filler and a polymer . Another and a fruitful way to exclude or minimize aging and to impart the membrane material resistance to separated components is the crosslinking of polymer chains . Using the controlled crosslinking of polymers, it is possible to tune the solubility of polymers making them partially soluble or even insoluble at all.…”

Section: Introductionmentioning

confidence: 99%

Crosslinking of addition copolymers from tricyclononenes bearing (CH₃)₃Si‐ and (C₂H₅O)₃Si‐groups as a modification of membrane gas separation materials

Alentiev

Egorova

Бермешев

et al. 2019

Polymer Engineering & Sci

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Here, we report the synthesis and the study of gas‐transport properties of crosslinked highly permeable copolymers from Si‐containing norbornene derivatives. The initial high‐molecular‐weight copolymers were prepared via addition copolymerization of 3‐trimethylsilyltricyclo[4.2.1.02,5]non‐7‐ene (TCNSi1) with 3‐triethoxysilyltricyclo[4.2.1.02,5]non‐7‐ene (TCNSiOEt) in good or high yields using a Pd‐catalyst. The obtained copolymers included up to 10 mol% of TCNSiOEt units bearing reactive Si–O–C‐containing substituents. The crosslinking was readily realized by using simple sol–gel chemistry in the presence of Sn‐catalyst. The formed crosslinked copolymers were insoluble in common organic solvents. Permeability coefficients of various gases (He, H2, O2, N2, CO2, CH4, C2H6, C3H8, n‐C4H10) in these copolymers before and after crosslinking were determined and the influence of the incorporated TCNSiOEt units as well as the crosslinking on gas transport properties were established. As a result, it was found that only a small reduction of gas‐permeability was observed when TNCSiOEt units were incorporated into the main chains, and the copolymers were crosslinked. At the same time, the selectivity for C4H10/CH4 pair was increased. The suggested approach has allowed obtaining crosslinked polymers from Si‐containing monomers without a loss of the main membrane characteristics. POLYM. ENG. SCI., 59:2502–2507, 2019. © 2019 Society of Plastics Engineers

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Reverse selective glassy polymers for C3+ hydrocarbon recovery from natural gas

Cited by 45 publications

References 9 publications

Macromolecular Design and Synthesis of Polymers from Silicon- Containing Norbornenes for Membrane Gas Separation

Macromolecular Design and Synthesis of Polymers from Silicon- Containing Norbornenes for Membrane Gas Separation

Addition Polyalkylnorbornenes: A Promising New Class of Si‐Free Membrane Materials for Hydrocarbons Separation

Crosslinking of addition copolymers from tricyclononenes bearing (CH₃)₃Si‐ and (C₂H₅O)₃Si‐groups as a modification of membrane gas separation materials

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Reverse selective glassy polymers for C3+ hydrocarbon recovery from natural gas

Cited by 45 publications

References 9 publications

Macromolecular Design and Synthesis of Polymers from Silicon- Containing Norbornenes for Membrane Gas Separation

Macromolecular Design and Synthesis of Polymers from Silicon- Containing Norbornenes for Membrane Gas Separation

Addition Polyalkylnorbornenes: A Promising New Class of Si‐Free Membrane Materials for Hydrocarbons Separation

Crosslinking of addition copolymers from tricyclononenes bearing (CH3)3Si‐ and (C2H5O)3Si‐groups as a modification of membrane gas separation materials

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Crosslinking of addition copolymers from tricyclononenes bearing (CH₃)₃Si‐ and (C₂H₅O)₃Si‐groups as a modification of membrane gas separation materials