Ethylene Oxide → HCID 18459385, compound

HRID 2305010Notes

Reaction equation

HRID 2305010 reaction equation
[CH2:1]([C:10]1([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C1OC1>[OH-].[Na+].C(O)(=O)C>[CH2:10]1[O:16][CH2:15]1.[CH2:1]([C:10]1([OH:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 6354Ethylene Oxide3×HCID 12496141HCID 12496141, compound2×

Product 1

HCID 18459385HCID 18459385, compoundYield 461%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 14798Sodium HydroxideCatalyst

Conditions

Temperature
120 °C

Procedure

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.

Workup

  1. customTo a 1,000 ml autoclave equipped with an ethylene oxide inlet tube
  2. customsuccessively evacuated to 50 mmHg
  3. customfor an hour
  4. temperatureheated to 150° C
  5. additioncharge
  6. waitthe reaction system was further kept at the same temperature for an hour

Sources & evidence

ORD record
ord-0bb48633c08f41dba2f66f428cbd8c1a
Source dataset
uspto-grants-2002_08
Patent number
US06437194B2

Reaction notes

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