1-Pentanol → 3-(Pentyloxy)propane-1,2-diol

HRID 2304981Notes

Reaction equation

HRID 2304981 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:7]([CH:9]1[O:11][CH2:10]1)Cl.[OH-:12].[K+]>>[CH2:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:9]([CH2:10][OH:12])[OH:11]

Participants

4

Conditions

Temperature
115 °C

Procedure

n-Pentanol (132 g) and 8.1 g of ferric chloride were heated to 100° C. while stirring, followed by the dropwise addition of 92.5 g of epichlorohydrin over 1 hour. The reaction mixture was then heated to 115° C. and reacted for 5 hours. After the removal of an excess alcohol at 100° C. under reduced pressure (5.32 kPa), 6 g of lauric acid, 118 g of a 48% aqueous solution of potassium hydroxide and 162 g of water were added to the residue. The resulting mixture was reacted at 200° C. for 5 hours in an autoclave. The reaction mixture was neutralized with 2.3 g of a 48% aqueous solution of potassium hydroxide. The reaction mixture was dehydrated at 100° C. under reduced pressure (6.67 kPa) and the residue was purified by distillation under reduced pressure (133 to 266 Pa, 114 to 115° C.), whereby 102 g of monopentyl glyceryl ether was obtained. As a result of GLC, it was found to that the resulting compound had a purity not less than 99% and the content of organochlorine compounds was not greater than 100 ppm.

Workup

  1. customreacted for 5 hours
  2. customAfter the removal of an excess alcohol at 100° C. under reduced pressure (5.32 kPa), 6 g of lauric acid, 118 g of a 48% aqueous solution of potassium hydroxide and 162 g of water
  3. additionwere added to the residue
  4. customThe resulting mixture was reacted at 200° C. for 5 hours in an autoclave
  5. customwas dehydrated at 100° C. under reduced pressure (6.67 kPa)
  6. distillationthe residue was purified by distillation under reduced pressure (133 to 266 Pa, 114 to 115° C.)

Sources & evidence

ORD record
ord-1dee41c8c7df4585b99204fd068f2d0e
Source dataset
uspto-grants-2002_08
Patent number
US06437196B1

Reaction notes

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