3-Chloro-1,2-propanediol → Sodium propylene glycol sulfonate

Sodium sulfite (120 g, 924 mmol, content: 97.0%, produced by Wako Pure Chemical Industries, Ltd.) was dissolved in water (400 mL), and 3-chloro-1,2-propanediol (107.2 g, 970 mmol, produced by Wako Pure Chemical Industries, Ltd.) was added thereto. The solution was refluxed by heating for 1 hour. After completion of the reaction, the reaction solution was concentrated, thereafter methanol (750 mL) was added to the concentrated residue. The crystal formed was filtered, and the resultant crystal was dried, to obtain sodium 2,3-dihydroxypropanesulfonate relevant to the above-described general formula [2] (202.6 g, content: 67.2%, yield: 82.7%) as a white crystal. It should be noted that content of sodium 2,3-dihydroxypropanesulfonate was obtained by 1H-NMR using the internal standard method. In addition, it was confirmed that the above-described white crystal contained crystal of sodium chloride as a by-product. Measurement results of 1H-NMR are shown below.

1. temperatureThe solution was refluxed
2. temperatureby heating for 1 hour
3. customAfter completion of the reaction
4. concentrationthe reaction solution was concentrated
5. additionmethanol (750 mL) was added to the concentrated residue
6. customThe crystal formed
7. filtrationwas filtered
8. customthe resultant crystal was dried

ORD record

ord-2d60c3e8e78c4f7eb245403a00c29ec9

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969591B2