Diels–Alder reactions of myrcene using intensified continuous-flow reactors

Abstract

This work describes the Diels–Alder reaction of the naturally occurring substituted butadiene, myrcene, with a range of different naturally occurring and synthetic dienophiles. The synthesis of the Diels–Alder adduct from myrcene and acrylic acid, containing surfactant properties, was scaled-up in a plate-type continuous-flow reactor with a volume of 105 mL to a throughput of 2.79 kg of the final product per day. This continuous-flow approach provides a facile alternative scale-up route to conventional batch processing, and it helps to intensify the synthesis protocol by applying higher reaction temperatures and shorter reaction times.

Synthesis of β‐myrcene/glycidyl methacrylate statistical and amphiphilic diblock copolymers by SG1 nitroxide‐mediated controlled radical polymerization

“…This incompatibility of My and MA to copolymerize might be explained by the formation of a Diels‐Alder adduct. The Diels‐Alder cycloaddition of isoprene with MA to yield 4‐methyl‐4‐cyclohexene‐1,2‐dicarbocylic anhydride is well known and a similar mechanism was also reported for the My /MA system . Supporting Information, Figure S4a gives the individual My and MA conversions versus reaction time for both experiments.…”

Pd(OAc)2/Ph3P-catalyzed dimerization of isoprene and synthesis of monoterpenic heterocycles

“…The different dimers of isoprene can be transformed into a large number of derivatives such as terpene-alcohols or ethers [ 38 ]. Moreover, some isoprene dimers have been submitted to Diels–Alder reactions with olefins such as maleic acid anhydride or methacrolein to form products that are used as alkyd coatings and perfume additives [ 39 – 40 ]. In addition, further functionalization reactions of the isoprene dimers can be carried out.…”

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

“…Recently, continuous-flow DA cycloadditions have been performed on myrcene (506), which is an acyclic monoterpene widely used as a building block in the F&F industry [427]. The authors wanted to prepare a new potential surfactant using myrcene (506) and acrylic acid (507).…”