25067-05-4Relevant articles and documents
Sustainable chemo-enzymatic synthesis of glycerol carbonate (meth)acrylate from glycidol and carbon dioxide enabled by ionic liquid technologies
Donaire, Antonio,Garcia-Verdugo, Eduardo,Lozano, Pedro,Luis, Santiago V.,Nieto, Susana,Porcar, Raul,Villa, Rocio
, p. 4191 - 4200 (2021/06/17)
A sustainable chemo-enzymatic process for producing both glycerol carbonate acrylate (GCA) and glycerol carbonate methacrylate (GCMA), as useful monomers for the preparation of biodegradable plastic materials, has been carried out by taking advantage of ionic liquid (IL) technologies. The process consisted of two consecutive catalytic steps, which can be carried out by either sequential or one-pot experimental approaches. Glycidyl (meth)acrylate was firstly synthesized by enzymatic transesterification of (meth)acrylate vinyl ester with glycidol in Sponge Like Ionic Liquids (SLILs) as the reaction medium (100% yield after 6 h at 60 °C). SLILs not only provided a suitable reaction medium, but also allowed the simple isolation of the resulting glycidyl esters as an IL-free pure fraction through a straightforward cooling/centrifugation protocol. The second step consisted of the synthesis of GCA, or GCMA, as the outcome of the cycloaddition of CO2to the obtained glycidyl acrylate or glycidyl methacrylate, respectively, catalysed by a covalently attached 1-decyl-2-methylimidazolium moiety (Supported Ionic Liquid-Like Phase, SILLP) in a solvent-free system and under mild conditions (60 °C, 1-10 bar), leading to up to 100% yield after 6 h. The components of the reaction system (biocatalyst/SLIL/SILLP) can be fully recovered and reused for at least 6 cycles with unchanged catalytic performance.
Life Cycle Assessment for the Organocatalytic Synthesis of Glycerol Carbonate Methacrylate
Büttner, Hendrik,Kohrt, Christina,Wulf, Christoph,Sch?ffner, Benjamin,Groenke, Karsten,Hu, Yuya,Kruse, Daniela,Werner, Thomas
, p. 2701 - 2707 (2019/06/13)
Bifunctional ammonium and phosphonium salts have been identified as potential organocatalysts for the synthesis of glycerol carbonate methacrylate (GCMA). Three of these catalysts showed high efficiency and allowed the conversion of glycidyl methacrylate with CO2 to the desired product in >99 % conversion and selectivity. Subsequently, immobilized analogues of selected catalysts were prepared and tested. A phenol-substituted phosphonium salt on a silica support proved to be a promising candidate in recycling experiments. The same catalyst was used in 12 consecutive runs, resulting in GCMA yields of up to 88 %. Furthermore, a life cycle assessment was conducted for the synthesis of GCMA starting from epichlorohydrin (EPH) and methacrylic acid (MAA). For the functional unit of 1 kg GCMA, 15 wt % was attributed to the incorporation of CO2, which led to a reduction of the global warming potential of 3 % for the overall process.
Production method of glycidyl methacrylate
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Paragraph 0015; 0016, (2016/11/14)
The invention relates to a production method of glycidyl methacrylate. The method comprises a reaction process and a post-treatment process. The reaction process is characterized in a one-step synthesis method. According to the reaction process, methacrylic acid and sodium carbonate are subjected to a neutralization reaction in excessive epichlorohydrin, such that sodium salt is prepared; without solid-liquid separation, system water content is removed with an azeotropic solvent; under the catalysis effect of a phase transfer catalyst, the glycidyl methacrylate is prepared. The post-treatment process comprises the following steps: a reaction finished liquid is washed; liquid separation is carried out, such that an organic phase is obtained; solvent recovery is carried out with a film evaporation device; and finished product distillation is carried out with a molecular distillation device. With the production method provided by the invention, production process and industrial equipment can be simplified, and operation is convenient. During the post-treatment process, phenomena of poor product polymerization rate and yield caused by high temperature, poor heat transfer effect, low distillation efficiency and the like of a conventional kettle distillation method can be avoided. With the method provided by the invention, product quality and yield can be effectively ensured. The obtained product has a purity higher than 98% and a yield of 85-90%.