Hydrogen Sulfide → Bis(3-chloro-2-hydroxypropyl)sulfide

HRID 593312Notes

Reaction equation

HRID 593312 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[SH2:6]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:2][CH2:1][CH:3]([OH:5])[CH2:4][S:6][CH2:4][CH:3]([OH:5])[CH2:1][Cl:2]

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 7835Epichlorohydrin

Product 1

HCID 19980843Bis(3-chloro-2-hydroxypropyl)sulfideYield 96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
22.5 °C

Procedure

185 g (2.0 mol) of epichlorohydrin, 10 ml of toluene and 0.97 g of tetra-n-butylammonium bromide were mixed together, and 35 g (1.0 mol) of hydrogen sulfide was blown into the mixture with stirring with the temperature of the solution being maintained at 20 to 25° C. After that, extraction was carried out using toluene to distil away the solvent, thereby obtaining 210 g (0.96 mol, yield: 96%) of bis(3-chloro-2-hydroxypropyl)sulfide (the compound represented by formula (1) above).

Workup

  1. extractionAfter that, extraction
  2. customto distil away the solvent

Sources & evidence

ORD record
ord-350b927241d84bf09cb7c54baa141403
Source dataset
uspto-grants-2016_01
Patent number
US09242947B2

Reaction notes

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