Selective flux of organic liquids and solids using nanoporous membranes of polydicyclopentadiene

Long, Tyler R.; Gupta, Abhinaba; Miller, Arthur K.; Rethwisch, David G.; Bowden, Ned B.

doi:10.1039/c1jm10970g

Cited by 25 publications

(41 citation statements)

References 64 publications

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“…As a very versatile monomer, it has found many applications in surface science and chromatography . Due to the highly crosslinked network, poly(dicyclopentadiene) membranes are also used in nanofiltration applications as size‐selective membranes . However, these membranes were found to be polydisperse with ill‐defined pores that are present in the nanometer scale only upon swelling.…”

Section: Introductionmentioning

confidence: 99%

Macroporous Polyolefin Membranes from Dicyclopentadiene High Internal Phase Emulsions: Preparation and Morphology Tuning

Kovačič

Preishuber-Pflügl

Slugovc

2014

Macromol. Mater. Eng.

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The curing of 200 mm thick, surfactant-stabilized water-in-dicyclopentadiene high internal phase emulsion films by ring opening metathesis polymerization yielded 140-200 mm thick, open-cellular macroporous membranes with 81.5 AE 2% porosity. Depending on the support on which high internal phase emulsion (HIPEs) were cast, different polyHIPE membrane surface morphologies ranging from almost closed (on steel) to fully open (on glass) were obtained. At the same time, the interior morphology of the membranes was identical, featuring cavity and window diameters of 7 AE 5 and 1.4 AE 0.6 mm, respectively. The membranes were tough and ductile, as revealed by a Young's modulus of 125 AE 8 MPa and an ultimate strength at break, which occurred at 20 AE 2% elongation and 3.1 MPa. The swelling behavior of the membranes was tested in several solvents and finally the swollen membranes were functionalized by bromination, yielding still ductile membranes of 80.6 AE 1% porosity and bromide loading of 5 mmol g À1 .

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Section: Introductionmentioning

confidence: 99%

Macroporous Polyolefin Membranes from Dicyclopentadiene High Internal Phase Emulsions: Preparation and Morphology Tuning

Kovačič

Preishuber-Pflügl

Slugovc

2014

Macromol. Mater. Eng.

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“…In We recently developed size-selective membranes based on highly cross-linked polydicyclopentadiene (PDCPD). 90,127 These membranes were fabricated by polymerizing 5,000 molar equivalents of dicyclopentadiene with one molar equivalent of the Grubbs first generation catalyst to yield solid, dense membranes. These membranes do not have well-defined pores such as zeolites; rather, when they are swollen in organic solvents, they possess openings between the polymer chains that small molecules may diffuse through.…”

Section: Icp-oes Sample Preparationmentioning

confidence: 99%

“…This method was also described in prior work. 90,127 Separation of a mixture of four fatty acids using multiple extractions A PDCPD membrane was added to the apparatus to study permeation. PDCPD membranes were fabricated as described in the experimental section ( Figure 3).…”

Section: Icp-oes Sample Preparationmentioning

confidence: 99%

“…The ring opening metathesis polymerization of the highly strained pi bond yielded polymer and the ring opening of the less strained ring yielded cross-links. 90,[127][128][129][130][131][132] In prior work it was shown that 83% of the less strained pi bond was ring opened which led to a highly cross-linked matrix. 90,127 Figure 3.3 The polymerization of dicyclopentadiene by the Grubbs first generation catalyst yielded a highly cross-linked solid polymeric slab.…”

Section: Icp-oes Sample Preparationmentioning

confidence: 99%

“…In our prior work, mixtures of two to five molecules were separated with membranes composed of PDCPD, but the separation of metals or phosphines from the products of a reaction were not studied. 90 In this chapter the separation of both phosphines and Pd from the products of two Pd-coupling reactions is demonstrated.…”

Section: Introductionmentioning

confidence: 99%

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Polydicyclopentadiene

Gupta¹

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Macroscopic, hollow thimbles were synthesized from dicyclopentadiene with the Grubbs second generation catalyst at a monomer:catalyst loading of 10,000:1. A series of Buchwald-Hartwig and Sonogashira coupling reactions were completed on the interior of the thimbles followed by extraction of the product to the exterior using hexane. In all examples, palladium was retained by the membranes at ≥99.9% levels. Both polar and apolar molecules with molecular weights from 101 to 583 g mol-1 permeated these thimbles with values for flux of 10-5 to 10-6 mol cm-2 h-1 , but selected molecules did not permeate them and had flux values 10 4 to 10 5 times slower. The difference in flux was large between molecules that permeated and those that did not permeate, but no trend was observed that correlated flux with molecular weight or hydrophobicity. Rather, molecules that did not permeate the membranes had large cross-sectional areas that led to low rates of diffusion within the highly cross-linked polydicyclopentadiene membranes. Membranes were fabricated from the ring opening metathesis polymerization of dicyclopentadiene with the Grubbs first generation catalyst at a monomer:catalyst loading of 5,000:1. Mixtures of fatty acid salts were separated using polydicyclopentadiene membranes. Mixtures of fatty acids could not be separated by the membranes, but when triisobutylamine was added to the fatty acids, cis-fatty acid salts had slower permeation though the membranes than saturated and trans-fatty acid salts. Oleic, petroselinic, vaccenic, linoleic, and linolenic acid salts with triisobutylamine had slower permeation relative to the permeation of stearic and elaidic acid salts. Organic catalysts were retained from organic molecules using nanoporous polydicyclopentadiene membranes. Acid or base was added to organic catalysts that increased the critical areas of the organic catalysts to the size range (>0.5 nm 2) where PDCPD membranes could retain them. The catalysts by themselves were too small to be v TABLE OF CONTENTS LIST OF TABLES ……………………………………………………………………….ix LIST OF FIGURES .

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Olefin Metathesis Polymerization

Knall

Slugovc

2014

Olefin Metathesis

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Selective flux of organic liquids and solids using nanoporous membranes of polydicyclopentadiene

Cited by 25 publications

References 64 publications

Macroporous Polyolefin Membranes from Dicyclopentadiene High Internal Phase Emulsions: Preparation and Morphology Tuning

Macroporous Polyolefin Membranes from Dicyclopentadiene High Internal Phase Emulsions: Preparation and Morphology Tuning

Polydicyclopentadiene

Olefin Metathesis Polymerization

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