2-Hexenoic acid → 3-Sulfohexanoic acid

HRID 66432

Reaction equation

HRID 66432 reaction equation
[C:1]([OH:8])(=[O:7])[CH:2]=[CH:3][CH2:4][CH2:5][CH3:6].[OH-].[Na+].[S:11](=[O:14])([OH:13])[O-:12].[Na+].S(=O)(O)[O-]>>[S:11]([CH:3]([CH2:4][CH2:5][CH3:6])[CH2:2][C:1]([OH:8])=[O:7])([OH:14])(=[O:13])=[O:12]

Participants

5

Reactant 4

HCID 144862-Hexenoic acidHCID 14798Sodium HydroxideHCID 104748BisulfiteHCID 23665763Sodium Bisulfite

Product 1

HCID 213296223-Sulfohexanoic acid

Procedure

114 g. of 2-hexenoic acid is neutralized with aqueous sodium hydroxide and reacted with 204 g. of a 50% wt. aqueous solution of sodium bisulfite at 25° C. Complete addition of bisulfite to the double bond requires several hours. The product is concentrated to approximately 50% wt. solids and then treated with a strong acid ion exchange resin to obtain an aqueous solution of 3-sulfohexanoic acid. This is dried by vacuum stripping and converted into 3-propyl-1,2-oxathiolane-5-one-2,2-dioixde with refluxing thionyl chloride at 80° C. for 3 hours. Equivalent weight is 93.

Workup

  1. customreacted with 204 g
  2. customat 25° C
  3. waitrequires several hours
  4. concentrationThe product is concentrated to approximately 50% wt. solids
  5. additiontreated with a strong acid ion exchange resin

Sources & evidence

ORD record
ord-e1f5c27a7f8c44479d059796dfe483c5
Source dataset
uspto-grants-1978_12
Patent number
US04131736

Linked notes

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