Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies

Sutter, Marc; Silva, Éric Da; Duguet, Nicolas; Raoul, Yann; Métay, Estelle; Lemaire, Marc

doi:10.1021/cr5004002

Cited by 143 publications

(177 citation statements)

References 383 publications

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“…Drying under reduced pressure at 50 • C gave polymer 7 as a colorless solid (0.648 g, 77%). 1 (8) Polymer 7 (0.263 g, 1.307 mmol HSL) was dissolved in DMF (4 mL), and 3-(dimethylamino)-1-propylamine (0.339 g, 3.268 mmol) and 4-(dimethylamino)pyridine (0.016 g, 0.131 mmol) were added. The mixture was stirred for 20 h at room temperature.…”

Section: General Procedures For the Polyaddition Of Peg-diamine To Hommentioning

confidence: 99%

“…Ring-Opening of P(G HSL ) 26 P(G HSL ) 26 (7) was reacted with 3-(dimethylamino)-1-propylamine (DMAPA) and 4-DMAP as a nucleophilic catalyst in a ring-opening reaction in DMF at room temperature (Scheme 7a). The synthesized P(G HSL,o ) 26 (8) was purified by precipitation in diethyl ether, followed by dialysis in MeOH and characterized by 1 H, 13 C NMR spectroscopy and SEC analysis (Figures S22-S24). Figure 3.…”

Section: Ring-opening Of P(g Hsl )26mentioning

confidence: 99%

“…As a model reaction for further functionalization, the quaternization of P(G HSL,o ) 26 (8) was conducted with methyl iodide in methanol under reflux (Scheme 7b). The solvent and excess methyl iodide was removed under reduced pressure and P(G HSL,o,q ) 26 (9) characterized by 1 H and 13 C NMR spectroscopy ( Figures S25 and S26).…”

Section: Quaternization Of P(g Hslo ) 26mentioning

confidence: 99%

“…Another approach towards sustainability involves the utilization of bio-based by-products. Glycerol is a readily available, major by-product in the production of biodiesel, and thus used as a starting material for the synthesis of monomers, such as epichlorohydrin and glycidol [8], or building blocks like glycerol carbonate (Scheme 1) [9].…”

Section: Introductionmentioning

confidence: 99%

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Homoserine Lactone as a Structural Key Element for the Synthesis of Multifunctional Polymers

et al. 2017

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Abstract:The use of bio-based building blocks for polymer synthesis represents a milestone on the way to "green" materials. In this work, two synthetic strategies for the preparation of multifunctional polymers are presented in which the key element is the functionality of homoserine lactone. First, the synthesis of a bis cyclic coupler based on a thiolactone and homoserine lactone is displayed. This coupler was evaluated regarding its regioselectivity upon reaction with amines and used in the preparation of multifunctional polymeric building blocks by reaction with diamines. Furthermore, a linear polyglycidol was functionalized with homoserine lactone. The resulting polyethers with lactone groups in the side chain were converted to cationic polymers by reaction with 3-(dimethylamino)-1-propylamine followed by quaternization with methyl iodide.

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Section: General Procedures For the Polyaddition Of Peg-diamine To Hommentioning

confidence: 99%

Section: Ring-opening Of P(g Hsl )26mentioning

confidence: 99%

Section: Quaternization Of P(g Hslo ) 26mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Homoserine Lactone as a Structural Key Element for the Synthesis of Multifunctional Polymers

et al. 2017

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“…[6,7] Notably, the synthesis of monoalkyl glyceryl ethers (MAGEs) is considered one of the most promising strategiesf or glycerole xploitation among the investigated syntheticr outes to convert glyceroli nto value-added products. [10] MAGEs preparation from glycerol, using both homogenous and heterogeneous catalysts, is one of the most investigated routest hanks to the abundance of feedstock on the market: glycerold emand is expected to reach 3.5 Mt by 2020. ), antiseptic and antimicrobial creams, pharmaceuticals and cosmetic products.…”

Section: Introductionmentioning

confidence: 99%

Glycidol, a Valuable Substrate for the Synthesis of Monoalkyl Glyceryl Ethers: A Simplified Life Cycle Approach

et al. 2017

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The disposal of any waste by recovering it within the production plant represents the ultimate goal of every biorefinery. In this scenario, the selective preparation of monoalkyl glyceryl ethers (MAGEs) starting from glycidol, obtained as byproduct in the epichlorohydrin production plant, represents a very promising strategy. Here, we report the synthesis of MAGEs through the reaction of glycidol with alcohols catalyzed by a green homogeneous Lewis acids catalyst, such as Bi triflate, under very mild reaction conditions. To evaluate the green potential of the proposed alternative, a simplified life cycle assessment (LCA) approach was followed by comparing the environmental performance of the proposed innovative route to prepare MAGEs with that of the most investigated pathway from glycerol. A considerable reduction of all impact categories considered was observed in our experimental conditions, suggesting that the glycidol-to-MAGEs route can be a valuable integration to the glycerol-to-MAGEs chain. Thanks to the use of primary data within the LCA model, the results achieved are a very good approximation of the real case.

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Oleochemistry

Vorholt¹,

Behr²

2017

Applied Homogeneous Catalysis With Organometallic Compounds

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Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies

Cited by 143 publications

References 383 publications

Homoserine Lactone as a Structural Key Element for the Synthesis of Multifunctional Polymers

Homoserine Lactone as a Structural Key Element for the Synthesis of Multifunctional Polymers

Glycidol, a Valuable Substrate for the Synthesis of Monoalkyl Glyceryl Ethers: A Simplified Life Cycle Approach

Oleochemistry

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