Chloride → Sodium 3-chloro-2-hydroxypropylsulfonate

HRID 1111229Notes

Reaction equation

HRID 1111229 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

Conditions

Temperature
87.5 °C

Procedure

The title alkylating agent was made by reacting sodium metabisulfite (104.5g) with epichlorohydrin (101.8g) in water (481g). To this solution of alkylating agent at 50-60° C. was added the product from Part A (157g). 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. customReaction
  3. customReaction
  4. customto remove water until sufficient water
  5. customhad been removed

Sources & evidence

ORD record
ord-b452669c414c4748865861b5a755d748
Source dataset
uspto-grants-1990_12
Patent number
US04978781

Reaction notes

Loading…