Recent Progress in Synthesis of Glycerol Carbonate and Evaluation of Its Plasticizing Properties

Abstract

The state of the art on the glycerol carbonate (GC) synthesis has been updated since the last published reviews in 2012, 2013, and 2016. Three types of reactions continue to be studied: glycerolysis of urea, transcarbonation of DMC, DEC, or cyclic carbonates with glycerol and reaction using CO 2 . Among these different routes, DMC and glycerol were selected as the raw materials for the GC synthesis in this work since the transcarbonation from these green reagents leads to high yields and selectivities, using mild conditions including a less energy consuming GC separation process. Catalytic conditions using Na 2 CO 3 seem to be a good compromise to achieve a high yield of GC, leading to an easier purification step without GC distillation. Mild temperatures for the reaction (73–78°C) as well as a low waste amount confirmed by the E-factor calculation, are in favor of controlled costs. Plasticizing properties of synthesized GC were compared to the behaviors of a commercial plasticizer and natural dialkyl carbonates, for a colorless nail polish formulation. The resulting films subjected to mechanical and thermal stresses (DMA and Persoz pendulum) showed the high plasticizing effect of GC toward nitrocellulose based films, probably due to hydrogen bond interactions between GC and nitrocellulose. The GC efficiency gives the possibility to decrease the content of the plasticizer in the formulation. Glycerol carbonate can be thus considered as a biobased ingredient abiding by the green chemistry concepts, and safe enough to be used in an ecodesigned nail polish formulation.

Recent Advances in Glycerol Catalytic Valorization: A Review

“…Several types of hydrotalcite have been tested, such as Al/Mg, Al/Li, Al/Ca, Mg/Al, etc. [214]. Some authors have focused on producing a catalyst from residues and waste.…”

Alkaline-Based Catalysts for Glycerol Polymerization Reaction: A Review

“…We can suppose that it might be linked to the CO 2 Lewis acidic nature, which could contribute to the reaction. However, the impact of CO 2 highly depends on temperature, solubility of CO 2 in glycerol, concentration of CO 2 , pressure [67] and further formation of glycerol carbonate [68]. Moreover, many studies kept CaO under nitrogen or used freshly calcined CaO in order to prevent "deactivation" of catalyst by contact with ambient air (reactions with CO 2 and H 2 O) and formation of CaCO 3 and Ca(OH) 2 , respectively [5,6].…”

One‐pot Fixation of CO2 into Glycerol Carbonate using Ion‐Exchanged Amberlite Resin Beads as Efficient Metal‐free Heterogeneous Catalysts

“…Glycerol is another interesting, renewable, abundant and cheap raw material since it is generated in large amounts as the main by‐product of biodiesel manufacturing [12,13] . In order to prevent glycerol over‐supply from hindering the development of the biodiesel industry, the conversion of glycerol into valuable products is highly desirable, and many approaches have been developed for this purpose [13–16] . Among these options, the transformation of glycerol into glycerol carbonate (GC) has drawn increasing attention in recent years [12] .…”

“…The synthesis of glycerol carbonate can be achieved through the reaction of glycerol with different compounds acting as carbonyl sources, such as carbon monoxide, [18,19] phosgene, [20] carbon dioxide, [18,21] urea, [22,23] and organic carbonates [13,24,25] . However, most of these routes present major issues such as: (i) the toxicity of the reagents, as in the case of phosgene and carbon monoxide; [12,15] (ii) the thermodynamic limitation associated with direct reaction with carbon dioxide, which can be only partially mitigated using sacrificial dehydrating agents ( e. g . 2‐cyanopyridine and acetonitrile) [21,26] or adsorbents ( e. g .…”

“…[12,13] In order to prevent glycerol over-supply from hindering the development of the biodiesel industry, the conversion of glycerol into valuable products is highly desirable, and many approaches have been developed for this purpose. [13][14][15][16] Among these options, the transformation of glycerol into glycerol carbonate (GC) has drawn increasing attention in recent years. [12] The obtained glycerol carbonate is non-toxic, non-flammable, water soluble and biodegradable.…”