Dimerization of Methyl Acrylate through CO2‐pressurized DBU Mediated Process

A selective and facile methyl acrylate (MA) head‐to‐tail dimerization process is here presented. The dimerization is articulated on the use of the 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) amidine organic base and the carbon dioxide (CO2) working gas used as mediator and water trap, respectively. Und...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2022-02, Vol.11 (2), p.n/a
Main Authors: Moins, Sébastien, Coulembier, Olivier
Format: Article
Language:English
Subjects:
Acrylics
Carbon dioxide
catalysis
Copolymerization
DBU
Dimerization
Dimers
methyl acrylate
Organic chemistry
Room temperature
Transesterification
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Summary:A selective and facile methyl acrylate (MA) head‐to‐tail dimerization process is here presented. The dimerization is articulated on the use of the 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) amidine organic base and the carbon dioxide (CO2) working gas used as mediator and water trap, respectively. Under moderated pressure of CO2 (20 to 40 bars), the selective production of MA dimer is carried out in bulk condition and at room temperature, offering perspectives to an industrially scalable process. The purity of the non‐isolated dimer is such that it could be directly step‐growth copolymerized with a diol taking profit of the presence of the amidine organic base acting as transesterification agent. The selective head‐to‐tail dimerization of methyl acrylate by associating DBU and CO2 is presented. The synergistic combination mediates the process but also transforms protic impurities, such as water in dormant spectators, offering a good perspective to an industrially scalable method. The purity of the crude dimer is such that it could be directly involved in a step‐growth copolymerization with a diol, using DBU as transfer agent.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202100734