Water → 3-(Pentyloxy)propane-1,2-diol

HRID 430483Notes

Reaction equation

HRID 430483 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-a08e1a0b2d5b478a8802686aecb19042
Source dataset
uspto-grants-2001_11
Patent number
US06323172B1

Reaction notes

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