Influence of solvents on the rates of reactions simulating the process of synthesis of epoxide resins

Роговина, С. З.; Salamatina, O. B.; Markevich, M.A.; Nepomnyashchii, A. I.; Enikolopyan, N. S.

doi:10.1007/bf01100007

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(2 citation statements)

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“…In addition, polar aprotic solvents seem preferable for the entire process because the reactions follow an S N 2 mechanism, which requires aprotic solvents to avoid a solvation shell. The literature has indicated that many solvents have been applied as reaction media in epoxy resin synthesis, including methanol (MeOH), dimethylformamide(DMF), dimethyl sulfoxide (DMSO), hexane, benzene, water, water/dioxane, , water/acetone, water/ethanol, water–toluene–butanol, water/DCM, and water/hexane. , The properties of these solvents are listed in Table .…”

Section: Results and Discussionmentioning

confidence: 99%

“…Two types of substrates with various hydroxyl values (OHV) and molecular weights were prepared using different drying techniques. For a typical glycidylation reaction, a wide range of solvents have been reported for both single-phase systems ,− and biphasic solvent systems. , The effects of solvent on the yield and reactivity could be further linked to its solute solubility and p K a value. Other important factors that must be considered in the selection process is the environment, health, and safety impacts (EHS) of the solvents.…”

Section: Introductionmentioning

confidence: 99%

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Effects of Reaction Parameters on the Glycidyl Etherification of Bark Extractives during Bioepoxy Resin Synthesis

Kuo

Barros

Sain

et al. 2016

ACS Sustainable Chem. Eng.

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This study outlines the influence of a series of reaction conditions on the yield and reactivity of the glycidyl etherification reaction of the bark extractive-based bioepoxy monomer (E-epoxy). To maximize the yield and epoxy content, the glycidylation reaction was examined with various substrates, solvents, catalysts, time periods, reaction temperatures, and sodium hydroxide/hydroxyl (NaOH/OHV) ratios. Spray-dried bark extractives were used as substrates due to their higher hydroxyl group content and lower molecular weight compared to the oven-dried bark extractives. A dioxane/water combination was selected from among four solvents based on the yield and epoxy equivalent weights of the final product, and tetrabutylammonium hydroxide was chosen as a ring-opening catalyst due to its effect of suppressing hydrolysis. Furthermore, a response surface methodology was applied to find the optimal reaction time, reaction temperature, and NaOH/OHV ratio of the E-epoxy monomer. The maximum extent of conversion with minimum epoxy equivalent weight was achieved after 4.5 h with an NaOH/OHV ratio of 3.4 at 80 °C. This work identifies the effects of reaction parameters on the yield and reactivity of E-epoxy and sheds new light on the glycidylation reaction between epichlorohydrin and renewable biomass.

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