Sulfuric Acid → HCID 131726061, compound

HRID 721999Notes

Reaction equation

HRID 721999 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.[CH2:22]([OH:27])[CH2:23][CH2:24][CH2:25][OH:26].[C:28](=O)([O-])[OH:29].[Na+]>O>[OH:26][CH2:25][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][CH2:28][OH:29].[CH2:22]([OH:27])[CH2:23][CH2:24][CH2:25][OH:26]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 80641,4-ButanediolHCID 178581,2-Epoxydodecane4×HCID 516892Sodium BicarbonateHCID 5284359Calcium Chloride

Product 1

HCID 131726061HCID 131726061, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
52.5 °C

Procedure

Separately, a 100 ml mixing vessel equipped with a calcium chloride-containing tube was charged with 36.9 g (0.20 mole) 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 0.4 g (0.004 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 1,4-butanediol contained in the reaction vessel and maintained at a temperature of 50 to 55° C. over a time of 2 hours. Then the reaction of the mixture was carried out at a temperature of 50 to 55° 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 saturated aqueous sodium hydrogen carbonate solution was mixed in an amount of 50 ml into the resultant reaction liquid in the reaction vessel, the resultant mixture was stirred for 10 minutes to neutralize the reaction liquid. The reaction liquid was subjected to an extraction procedure using diethyl ether to extract the reaction product. The resultant extraction liquid was concentrated by using a rotary evaporator. A 1,4-butanediol monohydroxydodecyl ether mixture was obtained in an amount of 50.4 g (yield: 94.1%).

Workup

  1. additionSeparately, a 100 ml mixing vessel
  2. additioncontaining tube
  3. customThen the reaction of the mixture
  4. waitwas carried out at a temperature of 50 to 55° C. for one hour
  5. customreaction liquid in the reaction vessel
  6. customthe reaction liquid
  7. customThe reaction liquid
  8. extractionwas subjected to an extraction procedure
  9. extractionto extract the reaction product
  10. extractionThe resultant extraction liquid
  11. concentrationwas concentrated
  12. customa rotary evaporator

Sources & evidence

ORD record
ord-1163446432a94676b634ff3ad3a2b443
Source dataset
uspto-grants-2006_11
Patent number
US07138365B2

Reaction notes

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