Ethylene Glycol → HCID 87904918, compound

HRID 721995Notes

Reaction equation

HRID 721995 reaction equation
[Cl-].[Ca+2].[Cl-].[O:4]1[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5]1.S(=O)(=O)(O)O.[C:22](=O)([O-])[OH:23].[Na+].[CH2:27]([OH:30])[CH2:28]O>O>[OH:23][CH2:22][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:4][CH2:5][CH:27]([OH:30])[CH3:28]

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 178581,2-Epoxydodecane4×HCID 516892Sodium BicarbonateHCID 5284359Calcium Chloride

Product 1

HCID 87904918HCID 87904918, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
62.5 °C

Procedure

Separately, a 500 ml mixing vessel equipped with a calcium chloride-containing tube was charged with 276.5 g (1.50 moles) of 1,2-epoxydodecane. While the charged 1,2-epoxydodecane was stirred and cooled with water, a concentrated sulfuric acid was gradually dropped in an amount of 2.7 g (0.027 mole) into the cooled 1,2-epoxydodecane. After stirring for 15 minutes, the resultant mixture was placed into the dropping apparatus attached to the reaction vessel and was dropped into the ethylene glycol contained in the reaction vessel and maintained at a temperature of 60 to 65° C. over a time of 2 hours. Then the reaction of the mixture was carried out at a temperature of 60 to 65° C. for one hour. After the exhaustion of the starting material, namely 1,2-epoxydodecane, was confirmed by a thin-layer chromatography, the reaction was stopped. A powdered sodium hydrogen carbonate was mixed in an amount of 2.5 g (0.03 mole) into the resultant reaction liquid in the reaction vessel, the resultant mixture was stirred for 30 minutes to neutralize the reaction liquid. From the reaction liquid, precipitated crystals were separated by filtration. An 1,2-propanediol monohydroxydodecyl ether mixture was obtained in an amount of 395.4 g (yield: 99.5%).

Workup

  1. additionSeparately, a 500 ml mixing vessel
  2. additioncontaining tube
  3. customThen the reaction of the mixture
  4. waitwas carried out at a temperature of 60 to 65° C. for one hour
  5. customreaction liquid in the reaction vessel
  6. customthe reaction liquid
  7. customFrom the reaction liquid
  8. customprecipitated crystals
  9. customwere separated by filtration

Sources & evidence

ORD record
ord-41848e912451403d91ffbbc533778927
Source dataset
uspto-grants-2006_11
Patent number
US07138365B2

Reaction notes

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