Chloride → Sodium 3-chloro-2-hydroxypropylsulfonate

HRID 329344Notes

Reaction equation

HRID 329344 reaction equation
[S:1](S([O-])=O)([O-:4])(=[O:3])=[O:2].[Na+:8].[Na+].[CH2:10]([CH:12]1[O:14][CH2:13]1)[Cl:11].[OH-].[Na+].[Cl-]>O>[Cl:11][CH2:10][CH:12]([OH:14])[CH2:13][S:1]([O-:4])(=[O:3])=[O:2].[Na+:8]

Participants

6

Reactant 4

HCID 312Chloride2×HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 656671Sodium Pyrosulfite

Product 1

HCID 23662382Sodium 3-chloro-2-hydroxypropylsulfonateYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title alkylating agent was made by reacting sodium metabisulfite (104.5 g) with epichlorohydrin (101.8 g) in water (481 g). To this solution of alkylating agent at 50°-60° C. was added the product from Part A (157 g). This mixture was stirred and heated to 85°-90° C. Reaction was continued with the pH maintained in the range 8 to 9 by the incremental addition of 50% aqueous NaOH. Reaction was continued until the pH had stabilized and the ratio of ionic chloride to total chloride exceeded 0.99. Vacuum was applied to remove water until sufficient water had been removed to give a 50% solids product which was a clear, yellow liquid.

Workup

  1. customat 50°-60° C.
  2. additionwas added the product from Part A (157 g)
  3. temperatureheated to 85°-90° C
  4. customReaction
  5. customReaction
  6. customto remove water until sufficient water
  7. customhad been removed

Sources & evidence

ORD record
ord-904cb07d637e4e75a9cd71663be963b4
Source dataset
uspto-grants-1990_01
Patent number
US04891159

Reaction notes

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