Development of a Safe and Scalable Process for the Preparation of Allyl Glyoxalate

While conversion of dialkyl tartrate esters to the corresponding glyoxalic acid esters has been well-documented, large scale application of some common laboratory protocols presents a myriad of challenges. The low cost, high availability, and predictable reactivity of sodium periodate make it an attractive choice for synthetic chemistry applications; the resulting solid byproducts, however, have a high thermal potential and therefore must be handled with care during cleanup and disposal, especially on large scale. Successful demonstration of the synthesis of glyoxaldehydes by oxidative cleavage of tartrate esters with sodium periodate is discussed herein. Furthermore, this account describes the process safety/engineering investigation carried out to ensure a robust and safe process for the scale manufacture of allyl glyoxalate via sodium periodate-mediated cleavage of diallyl tartrate.