Improvement of the phase‐transfer catalysis method for synthesis of glycidyl ether

Abstract

A convenient procedure for the synthesis of aliphatic alkylglycidyl ether has been studied. It has been found that the improved preparation of the alkylglycidyl ether can be achieved by using fatty alcohol such as octanol and octadecanol with epichlorohydrin in the presence of phase-transfer catalyst (PTC) such as 1-alkyloxypropan-2-ol-3-trimethyl ammonium methylsulfate, 1-alkyloxypropan-2-ol-3-methyldiethanolammonium methylsulfate, alkyloxy-2-hydroxypropyldimethylamine and alkyloxy-2-hydroxypropyldiethanolamine, tetrabutylammonium bromide, etc. without water and other organic solvents. This method, carried out in solid phase/organic phase (reactants and product themselves), has the following merits: (i) producing the solid by-products such as sodium chloride and sodium hydroxide which are easily removed by simple filtration, (ii) saving the amount of reactants used such as sodium chloride and phase-transfer catalyst, and (iii) increasing the yields of glycidyl ethers. The yields of octylglycidyl ether and octadecylglycidyl ether are 92.0 and 91.7%, respectively. The amount of sodium hydroxide used can be saved by from 1.5 to 0.7 molar ratio with respect to octanol in comparison with those in the conventional method using PTC.Paper no. J9599 in JAOCS 78, 423-429 (April 2001).

Synthesis, Characterization and Evaluation of the Surface Active Properties of Novel Cationic Imidazolium Gemini Surfactants

“…The preparation of compounds (1-3) were prepared by reacting fatty alcohols (hexadecyl, tetradecyl and dodecyl) with epichlorohydrin in 1:1.5 using tetrabutylammonium iodide as a catalyst and sodium hydroxide (1:2) ratio. The resulting products were characterized as 2-alkoxy methyloxirane (1)(2)(3).The synthesis of the compounds (1-3) was reported in parenthesis [19].…”

Novel amphiphilic chitosan derivatives: Synthesis, characterization and micellar solubilization of rotenone

“…All commercially available solvents and reagents were used without further purification. Kang et al (2001) as shown in Scheme 1. Toluene (30 mL) as solvent, CTAB (1.0 g) as catalyst, 1-octadecanol (0.1 M) mixed with NaOH (6.0 g) were all added to a flask (100 mL) and melt completely by heating.…”

“…Alkylglycidyl ether with a long alkyl chain is very important intermediates in pharmaceutical applications (Kang, Lee, Yoon, & Yoon, 2001). However, the chitosan derivatives which grafted alkylglycidyl ether have not been reported up to now.…”

Synthesis of natural ether lipids and 1-O-hexadecylglycero-arylboronates via an epoxide-ring opening approach: Potential antifouling additives to marine paint coatings

“…The same reaction, also using epychlorohydrin as starting material was performed with stearylic and oleylic alcohols giving the corresponding 1-O-octadecyl-2,3-epoxypropane (5), and 1-O-oleyl-2,3-epoxy propane (6) in 98% and 92% yield respectively. A similar experimental procedure was described by Yoon and coworkers [14]. The treatment of 1-O-hexadecyl-2,3-epoxypropane (4), 1-O-octadecyl-2,3-epoxypropane (5) and 1-O-oleyl-2,3-epoxy propane (6) with catalytic amounts of boron trifluoride etherate and 1.3 equivalents of phenyl boronic acid dissolved in dry dioxane, provided the 1-Ohexadecylglycero-phenylboronate (7), 1-Ooctadecylglycero-phenylboronate (8) and 1-Ooleylglycero-phenylboronate (9) in 100%, 99%, 97% yields.…”