Ethylene Oxide → HCID 18459385, compound

Participants

Reaction Conditions

Reaction Steps

To a 1,000 ml autoclave equipped with an ethylene oxide inlet tube, 226.5 g (1.0 mole) of nonylcyclohexanol and 0.67 g (6.7 mmoles as sodium hydroxide) of 40% aqueous sodium hydroxide solution were charged. The reaction system was substituted with nitrogen, heated to 120° C., successively evacuated to 50 mmHg, and carry out dehydration for an hour under reduced pressure. After dehydration, the system was returned to atmospheric pressure by feeding nitrogen, and heated to 150° C. While maintaining the temperature, 396.5 g (9.0 moles) of ethylene oxide was fed into the reaction system over 3 hours under gauge pressure of 0.2 to 0.4 MPa to carry out ethylene oxide addition reaction of nonylcyclohexanol. After finishing ethylene oxide charge, the reaction system was further kept at the same temperature for an hour and the catalyst was neutralized after cooling with 0.42 g (7.0 mmoles) of acetic acid to obtain 623.4 g of nonylcyclohexanol ethylene oxide adduct as white solid at room temperature. The white solid was analyzed by liquid chromatography. The solid contained 38.8% by weight of unreacted nonylcyclohexanol, 0.5% by weight of formed one molar ethylene oxide adduct of nonylcyclohexanol, 1.1% by weight of two molar adduct, 1.6% by weight of three molar adduct, 2.3% by weight of four molar adduct, 3.4% by weight of five molar adduct, 4.3% by weight of six molar adduct, 5.2% by weight of seven molar adduct, 6.3% by weight of eight molar adduct, 7.4% by weight of nine molar adduct, 6.6% by weight of ten molar adduct, 5.8% by weight of eleven molar adduct, and 4.7% by weight of twelve molar adduct, 4.1% by weight of thirteen molar adduct, 3.2% by weight of fourteen molar adduct, and 4.7% by weight of fifteen or more molar adduct.

Provenance & Evidence