Free-solvent Michael addition of glycerol to acrylic compounds

Abstract

Functionalization of biobased glycerol by acrylic compounds was optimized and the tricyanoethylglycerol can be used as a prochiral core of dendrimers.

Step-growth polymerisation of alkyl acrylates via concomitant oxa-Michael and transesterification reactions

“…These findings are in accordance with Oget et al who reported that in the oxa-Michael addition reaction of heptanols and t-butyl acrylate hardly any transesterification takes place. 18 Subsequently, 2 was used as Michael acceptor in all further experiments. In case of DMAP, only shorter oligomers formed, mainly because transesterification remained a challenge, leaving approx.…”

“…17 It has also been used as catalyst in the oxa-Michael addition of glycerol and acrylic compounds. 18 Moreover, transesterification reactions efficiently catalysed by DBU have been reported. 19 Recently it has been used as a dual catalyst allowing DBUpterin salt formation and concomitant ester-amidetransformation.…”

KOtBu‐Catalyzed Michael Addition Reactions Under Mild and Solvent‐Free Conditions

“…Thus, av ariety of organic and inorganic bases were reported, which catalyzed the Michael addition reactions with limited successa nd often suffer from the requirement of solvents, additives, and high pressure conditions. [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] The ability of transition metal complexes for the X-H (X = C, N, O, S, etc.) bond activation is very well established over the past decades.…”

“…Development of efficient catalytic protocol for the oxa‐ and aza‐Michael additions is highly desirable as alcohols and amines are cheap industrial feedstock chemicals that can produce valuable products in chemical synthesis. Thus, a variety of organic and inorganic bases were reported, which catalyzed the Michael addition reactions with limited success and often suffer from the requirement of solvents, additives, and high pressure conditions …”

Step-Growth Polymerisation of Alkyl Acrylates via Concomitant Oxa-Michael and Transesterification Reactions

“…Therefore, ethyl acrylate (2) was studied as an alternative Michael acceptor. Even though ethanol can also react as Michael donor, less side product formation (8% of chains terminated with 3ethoxypropionate) and a similar molecular mass in comparison to methyl acrylate could be observed with Michael addition reaction of heptanols and t-butyl acrylate hardly any transesterification takes place 18. Subsequently, 2 was used as Michael acceptor in all further experiments.…”