Alkene–azide chemistry: a facile, one-step, solvent- and catalyst-free approach for developing new functional monomers and polymers

Santra, Santimukul; Bean, Ren; Heckert, Blaze; Shaw, Zachary; Jain, Vedant; Shrestha, Lok Kumar; Narayanam, Raghunath; Austin, Quentin

doi:10.1039/d0py00346h

Cited by 7 publications

(3 citation statements)

References 43 publications

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“…Thus, a large amount of solvents are still used to fabricate polymer products, despite constant efforts at reducing their use over the years. 14 For example, in 2015, 16 million tons of solvents were still used for producing 320 million tons of polymers. However, the use of solvents is concomitant with production capacity reduction and huge additional costs related to the solvents themselves, their recovery from the polymer product after the polymerization, and their treatment, needless to mention the negative impacts of the use of solvents on the environment.…”

Section: Introductionmentioning

confidence: 99%

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Intensification of Polymerization Processes by Reactive Extrusion

et al. 2021

Ind. Eng. Chem. Res.

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The unique geometry of screw extruders allows handling very viscous media; thus, they can be used as continuous reactors to conduct polymerization reactions without using any solvents. This is called reactive extrusion polymerization. It is an intensified process as it maximizes reaction rates upon maximizing the concentrations of monomers and an initiator/catalyst (if there is any). It also allows conducting polymerization reactions at higher temperatures, without having to take measures to prevent solvents from evaporating or to work under pressure. However, screw extruders are not suitable for the early stage of polymerization in which the viscosity of the polymerization system may not be high enough for the rotation of the screws to generate a steady flow. A combination of continuously stirred tank reactors and a twin-screw extruder or several in series is preferred for the polymerization process. This review shows how reactive extrusion may intensify different types of polymerization processes under the constraint of no solvents, such as free-radical polymerization, anionic polymerization, ring-opening polymerization, and polycondensation, on one hand; and how challenges are met, on the other hand.

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Section: Introductionmentioning

confidence: 99%

“…It may also favor some of the reactions involved in the polymerization. Thus, a large amount of solvents are still used to fabricate polymer products, despite constant efforts at reducing their use over the years . For example, in 2015, 16 million tons of solvents were still used for producing 320 million tons of polymers.…”

Section: Introductionmentioning

confidence: 99%

Intensification of Polymerization Processes by Reactive Extrusion

et al. 2021

Ind. Eng. Chem. Res.

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“…In this term, the prenyl group (diene group) meets this requirement. Diene can react through reversible interactions via π-alkene and alkane-alkene interactions and by a selective irreversible covalent mechanism with various nucleophiles such as SH, Se, or N 3 through different types of chemistries [26][27][28][29] in the presence of free amino groups.…”

Section: Introductionmentioning

confidence: 99%

Geranyl Functionalized Materials for Site-Specific Co-Immobilization of Proteins

et al. 2021

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Different materials containing carboxylic groups have been functionalized with geranyl-amine molecules by using an EDC/NHS strategy. Chemical modification of the support was confirmed by XRD, UV-spectrophotometer, and FT-IR. This geranyl-functionalized material was successfully applied for four different strategies of site-selective immobilization of proteins at room temperature and aqueous media. A reversible hydrophobic immobilization of proteins (lipases, phosphoglucosidases, or tyrosinase) was performed in neutral pH in yields from 40 to >99%. An increase of the activity in the case of lipases was observed from a range of 2 to 4 times with respect to the initial activity in solution. When chemically or genetically functionalized cysteine enzymes were used, the covalent immobilization, via a selective thiol-alkene reaction, was observed in the presence of geranyl support at pH 8 in lipases in the presence of detergent (to avoid the previous hydrophobic interactions). Covalent attachment was confirmed with no release of protein after immobilization by incubation with hydrophobic molecules. In the case of a selenium-containing enzyme produced by the selenomethionine pathway, the selective immobilization was successfully yielded at acidic pH (pH 5) (89%) much better than at pH 8. In addition, when an azido-enzyme was produced by the azide–homoalanine pathway, the selective immobilization was successful at pH 6 and in the presence of CuI for the click chemistry reaction.

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