Functionalization of polystyrene. 1. Alkylation with substituted benzyl halide and benzyl alcohol compounds

Warshawsky, Abraham; Kalir, Rami; Patchornik, A.

doi:10.1021/jo00410a012

Cited by 36 publications

(12 citation statements)

References 11 publications

(22 reference statements)

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“…Persuad and Cantwell [30] have immobilized quinoline-8-ol onto Amberlite XAD-2 resin via a 5-chloromethylated oxine intermediate based on the synthetic procedure described by Warshawsky et al [31,32]. This procedure is based on the attachment of a methylene linkage of oxine to a copolymer backbone and is superior to the azo linkage method [33,34], which leaves amine groups in the polymer.…”

Section: Synthesis Of Quinoline-8-ol-immobilized Amberlite Xad-4 Resinmentioning

confidence: 99%

Quinoline-8-ol-immobilized Amberlite XAD-4: Synthesis, characterization, and uranyl ion uptake properties suitable for analytical applications

Gladis

Rao

2002

Anal Bioanal Chem

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Amberlite XAD-4 has been functionalized by coupling it with 5-aminoquinoline-8-ol after acetylation. The resulting resin has been characterized by elemental analysis and IR spectra and has been used for preconcentrating uranyl ions prior to its determination by spectrophotometry. The optimum pH value for quantitative sorption is 4-6, and desorption can be achieved by using 5 mL of 1 mol L(-1) HCl. The sorption capacity of the resin is 11.5 mmol g(-1). The effect of various cations and anions on the preconcentration of uranium in conjunction with the determination procedure has been studied and we have found that none of the ions interfere except thorium. The enrichment factor for preconcentration of uranium was found to be 200. Ten replicate determinations of 40 micro g of uranium present in 1 L of sample gave a mean absorbance of 0.185 with a relative standard deviation of 2.64%. The detection limit corresponding to three times the standard deviation of the bank was found to be 2 micro g L(-1). The validation of the developed preconcentration procedure was carried out by successfully analyzing standard marine sediment reference material. The uranyl content of sediment and soils is estimated by spectrophotometry after its preconcentration with the above chelating resin.

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Section: Synthesis Of Quinoline-8-ol-immobilized Amberlite Xad-4 Resinmentioning

confidence: 99%

Quinoline-8-ol-immobilized Amberlite XAD-4: Synthesis, characterization, and uranyl ion uptake properties suitable for analytical applications

Gladis

Rao

2002

Anal Bioanal Chem

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“…These techniques are general to awide range of aromatic polymers and allow for the incorporation of valuable functionality,i ncluding benzoyl groups, [28] anhydrides, [29,30] branching junctions, [31,32] and more. [33][34][35][36] Tr aditionally,F riedel-Crafts alkylations or acylations on polymers result in significant broadening of the molecular-weight distribution (MWD) even at low amounts of functionalization as ac onsequence of chain scission caused by the harsh reaction conditions. [37] Recent studies have investigated alternative Lewis acids, [31] modified order of addition, [31] and used microwave conditions [38] to limit deleterious side reactions.…”

Section: Aromatic Polymersmentioning

confidence: 99%

C−H Functionalization of Commodity Polymers

et al. 2019

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Synthetic manipulation of polymer substrates is one of the oldest and most reliable methods to increase the functional diversity of soft materials. Modifying the chemical structure of polymers that are already produced on a commodity scale leverages the current high‐volume and low‐cost production of commodity plastics for the discovery of modern materials. A myriad of polymer C−H functionalization methods have been developed which enable the modification of material properties on both a laboratory and industrial scale. More recently, driven by advances in C−H activation, photoredox catalysis, and radical chemistry, chemoselective approaches have emerged as a means to impart precise functionality onto commodity polymer substrates. This Review discusses the historical significance of and contemporary advances in the C−H functionalization of commodity polymers. The conceptual approach outlined herein presents exciting new directions for the field, including increasing the value of otherwise pervasive materials, uncovering entirely new material properties, and a viable path to upcycle post‐consumer plastic waste.

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“…R=OAc, R1 =Ac, R2=CH3 21, R=I, R1 =Ac, R2=CH3 22, R=OAc, R1 =Ac, R~= A c 23, R=OAc, R1 =n-propyl, R2=CH3Several minor compounds(21)(22)(23) were detected in the product mixture. Combined, they accounted for less than 5% of the amount of guaiacylpropanol present.…”

mentioning

confidence: 97%

“…This may not be the case in the heterogeneous system.The appearance of compound22 indicated that a small amount of methyl aryl ether cleavage had occurred. Methyl ether cleavage during ITS treatment is known to be slow relative to that of the benzyl ethers and often requires harsher conditions.44 Compound 23, which is observed in trace quantities, is believed to result from the reduction of residual ally1 groups during the course of the synthesis.…”

mentioning

confidence: 99%

Insoluble Lignin Models (3): Preparation of a Polymer-Bound Guaiacylpropanol Model

Barkhau¹,

Malcolm²,

Dimmel³

1990

Journal of Wood Chemistry and Technology

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Guaiacylpropanol (4), has been attached at the gamma carbon through a benzyl ether linkage to a macroreticular polystyrene resin. The phenolic site of 4 was protected as an ally1 ether when coupled to the resin. The amount of lignin model 4 which was attached to the polymer was determined by cleaving the benzyl ether linkage with iodotrimethylsilane (ITS) and quantifying the amount of released guaiacylpropanol. The ITS method was reproducible but not quantitative due to a high model loading (1.29 mmol/g). Both FTIR and W-NMR were used to characterize the insoluble model.

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Functionalization of polystyrene. 1. Alkylation with substituted benzyl halide and benzyl alcohol compounds

Cited by 36 publications

References 11 publications

Quinoline-8-ol-immobilized Amberlite XAD-4: Synthesis, characterization, and uranyl ion uptake properties suitable for analytical applications

Quinoline-8-ol-immobilized Amberlite XAD-4: Synthesis, characterization, and uranyl ion uptake properties suitable for analytical applications

C−H Functionalization of Commodity Polymers

Insoluble Lignin Models (3): Preparation of a Polymer-Bound Guaiacylpropanol Model

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