Reaction of ethylene oxide or propylene oxide with long‐chain fatty acids. Mono‐ and diester formation

Abstract

SummaryThe alkali‐catalyzed reaction of ethylene oxide or propylene oxide with fatty acids was shown to be complex. Mono‐ and diesters were formed in comparable amounts even at an early stage when only about one equivalent of the cyclic ether had been condensed.The following compounds were isolated in a pure state: ethylene glycol monolaurate, ethylene glycol dilaurate, diethylene glycol dilaurate, ethylene glycol distearate, 1,2‐propylene glycol dilaurate, and 1,2‐propylene glycol distearate. A monoester from propylene oxide was shown to be a mixture of the 1‐and 2‐monolaurate [C11H23CO2CH2CHOHCH3 and C11H23CO2CH(CH3)CH2OH].

Non‐ionic Surfactants

“…Initially, the ethylene oxide reacts with the acid to produce ethylene glycol monoester, RCOO(CH 2 CH 2 O)H, and then reacts rapidly with further ethylene oxide to produce the polyethoxylated product RCOO(CH 2 CH 2 O)nH. However, the reaction conditions are ideal for ester interchange and the final product contains free polyethylene glycol, the monoester and the diester [RCOO(CH 2 CH 2 O)nOCR] in the ratio 1:2:1 [21,22]. An alternative method of preparation of these products is to react polyethylene glycol of desired molecular weight and esterify it with acid in an ester kettle.…”

Preparation of Polyester Polyol from Epoxidized Palm Olein

“…The preparation of monoester and diester by reacting ethylene and propylene oxide with organic monocarboxylic acid such as lauric acid, stearic acid and oleic acid is well established. 2 The distillation reaction of phenylglycidyl ether (the epoxy) with caproic acid (the carboxylic acid) has also been used in the study of network formation of monoester and diester by-products. 3 The rate of reaction can be accelerated by using amine and chromium chelate as catalysts.…”

“…These products are most commonly used as fat-based non-ionic detergents and surface active agents. 2 Other applications include the starting material, reactant or additive in the manufacturing of thermoplastic, resins for coating, printing inks and coatings and most of these polyester polyols are prepared from synthetic epoxy compounds derived primarily from crude oil. 5,8,9 Polyester polyols can also be synthesized by reacting epoxy resin with oleic acid and ricinoleic acid with the presence of triethylamine as catalyst.…”

Preparation and emulsifying properties of polyethylene glycol (15OO) diesters of fatty acids

“…PEG fatty acid esters can be prepared by either ethoxylation (1,2) or esterification (3). PEG fatty acid esters can be prepared by either ethoxylation (1,2) or esterification (3).…”

“…Polyethylene glycol (PEG-1500) diesters of long chain fatty acids of low HLB are non-ionic oil soluble emulsifiers and are used extensively in a variety of applications such as in emulsion paints, emulsifiable solvent cleaners and other emulsion dispersions/formulations. PEG fatty acid esters can be prepared by either ethoxylation (1,2) or esterification (3). The latter process is safer as it does not involve the handling of hazardous ethylene oxide and is more easily controllable by changing the reaction parameters.…”