Epichlorohydrin → Sodium 3-chloro-2-hydroxypropylsulfonate

HRID 2399185Notes

Reaction equation

[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[S:6](=[O:9])([OH:8])[O-:7].[Na+:10]>>[Na+:10].[Cl:2][CH2:1][CH:3]([OH:5])[CH2:4][S:6]([O-:9])(=[O:8])=[O:7]

Participants

Reactant 2

HCID 7835Epichlorohydrin2×

HCID 23665763Sodium Bisulfite

Product 1

HCID 23662382Sodium 3-chloro-2-hydroxypropylsulfonate

Conditions

Temperature: 80 °C

Procedure

Epichlorohydrin (one mole, 93 g) is slowly added to an aqueous solution of one mole sodium bisulfite (104 g in about 120 ml water) while maintaining the temperature at about 80° C. The epichlorohydrin is added dropwise over about three hours, and after addition is complete, the mixture is stirred for an additional hour. After the mixture cools to about 20° C., the solids of 3-chloro-2-hydroxypropylsulfonic acid sodium salt formed from the reaction are filtered and analyzed by Nuclear Magnetic Resonance (NMR). The ISC spectra shows peaks at 69.99 ppm, 56.97 ppm, and 51.18 ppm from TMS (tetramethyl silane) and the proton spectrum shows, three groups of peaks centering at 2.95, 3.58 and 4.17 ppm (from TMS), in a 2:2:1 ratio respectively, consistent with the structure of CHPS.

Workup

additionafter addition
customcools to about 20° C.

Sources & evidence

ORD record: ord-4de89edd454244a2b53003f1161debdf
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05447575

Reaction notes

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