Stearic Acid → Octadecanoic acid, 26-hydroxy-3,6,9,12,15,18,21,24-octaoxahexacos-1-yl ester

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Reaction Steps

PEG400MS (polyethylene glycol 400 monostearate)—100 g (0.25 mol) of CARBOWAX™ 400 diol (commercially available from Union Carbide Corp., Danbury, Conn.) was combined with 71 g (0.25 mol) of stearic acid in 400 g of toluene in a 3-necked flask equipped with stirrer, heating mantle, thermometer and condenser. The contents were heated, azeotroped dry using a Dean Stark trap, and were allowed to cool. Next, 1.0 g (0 5% by weight of solids) of p-toluene sulfonic acid was added, and the mixture was refluxed with stirring overnight with the continuous removal of water. Infrared analysis indicated no acid carbonyl remained. A solution of 0.5 g of NaHCO3 in deionized water was then added. The resulting two-phase system was stirred and the water and toluene were removed at 80° C. using a ROTO-VAC™ evaporator to produce the desired monoester, C17H35C(O)O(C2H4O)8C2H4OH. This monostearate and its constituent reactants are presented as the first entry in TABLE 1.

Provenance & Evidence