Water → 3-(Pentyloxy)propane-1,2-diol

HRID 495975Notes

Reaction equation

HRID 495975 reaction equation
[OH2:1].[OH-].[Na+].[CH2:4]([OH:9])[CH2:5][CH2:6][CH2:7][CH3:8].[CH2:10]([CH:12]1[O:14][CH2:13]1)Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[Hg].CCCCCC>[CH2:4]([O:9][CH2:10][CH:12]([OH:14])[CH2:13][OH:1])[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 962WaterHCID 62761-PentanolHCID 7835Epichlorohydrin2×HCID 14798Sodium Hydroxide

Product 1

HCID 908193-(Pentyloxy)propane-1,2-diol

Reagents, catalysts & solvents 3

HCID 23931MercuryCatalystHCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8058HexaneSolvent

Procedure

A 3-neck, 2-liter round bottomed reaction flask (equipped with overhead stirrer, cold water condenser, mercury thermometer and addition funnel) are charged with about 546 g of aqueous NaOH (about 50% concentration) and about 38.5 g of tetrabutylammonium hydrogen sulfate (PTC, phase transfer catalyst). The content of the flask is stirred to achieve dissolution and then about 200 g of 1-pentanol is added along with about 400 ml hexanes (a mixture of isomers, with about 85% n-hexane). Into the addition funnel is charged about 418 g of epichlorohydrin which is slowly added (dropwise) to the stirring reaction mix. The temperature gradually rises to about 68° C. due to the reaction exotherm. The reaction is allowed to continue for about 1 hr after complete addition of the epichlorohydrin (no additional heat).

Workup

  1. dissolutiondissolution
  2. additiona mixture of isomers
  3. additionis slowly added (dropwise)
  4. customto the stirring reaction
  5. additionmix
  6. customgradually rises to about 68° C. due to the reaction exotherm
  7. temperatureno additional heat)

Sources & evidence

ORD record
ord-29d78c92388d4238adcb3d7abd103938
Source dataset
uspto-grants-2005_09
Patent number
US06943144B1

Reaction notes

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