Coolade. A Low‐Foaming Surfactant for Organic Synthesis in Water

Abstract

Several types of reduction reactions in organic synthesis are performed under aqueous micellar‐catalysis conditions (in water at ambient temperature), which produce a significant volume of foam owing to the combination of the surfactant and the presence of gas evolution. The newly engineered surfactant “Coolade” minimizes this important technical issue owing to its low‐foaming properties. Coolade is the latest in a series of designer surfactants specifically tailored to enable organic synthesis in water. This study reports the synthesis of this new surfactant along with its applications to gas‐involving reactions.

Water as the reaction medium in organic chemistry: from our worst enemy to our best friend

“… 68 This led to the creation of Coolade, a designer surfactant formulated without a hydrocarbon tail. 69 Methyl anthranilate, a flavoring agent with a grape scent, was added to both ends of a hydrophilic PEG chain bearing succinic acid ester linkages ( Fig. 16 ).…”

“…This key characteristic has been used to great advantage for nitro group reductions (using NaBH 4 + Fe/ppm Pd NPs), 49 and azide reductions (with Zn + NH 4 Cl). 69 Moreover, when designing the route to Coolade, green chemistry principles were fully considered.…”

Organic synthesis in Aqueous Multiphase Systems — Challenges and opportunities ahead of us

“…A variety of such nonionic benign by design surfactants is all considered PEGylated amphiphilic species, with or without a linker. TPGS-750-M [24], PQS [25], SPGS-550-M [26], Coolade [27], DAPGS-750-M [28], APGS-550-M [29], MC-1 [30], PTS [31], SMPS [32], BTBT-750-M, PiNAP-750-M [33], TPGlite [34], or PS-750-M [35] are some of the most studied excipients (Scheme 1). They have been demonstrated to be extremely versatile, most notably TPGS-750-M and PS-750-M, and shown to function as suitable surrogates to reprotoxic polar aprotic solvents, thus offering a real opportunity to phase out such solvents.…”

Syntheses of Organic Semiconductors in Water. Recent Advancement in the Surfactants Enhanced Green Access to Polyconjugated Molecules

“…Such pioneering work inspired other synthetic chemists to develop additional designer surfactants for specific purposes. [25,26] As we will see, the concept is relevant also for the manufacturing of organic semiconductors.…”