Ethylene Oxide → Octadecyl sulfide

HRID 261345Notes

Reaction equation

HRID 261345 reaction equation
[CH2:1]([SH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Na].[CH2:21]1O[CH2:22]1>COCCOCCOC>[CH2:1]([S:19][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:21][CH3:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6354Ethylene Oxide2×HCID 179051-Octadecanethiol2×HCID 5360545Sodium

Product 1

HCID 74609Octadecyl sulfideYield 65%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

1-Octadecanethiol, 250 g. (0.87 mole), was dissolved in 250 ml of bis-(2-methoxyethyl) ether. Three grams (0.13 mole) of cut sodium spheres were added and the reaction mixture was transferred to a rocking autoclave and ~462 g. of ethylene oxide was bled into the autoclave over a period of 3 hours at 140°-160° C. The maximum pressure observed was 540 lbs. After all the ethylene oxide had been added, rocking was continued for an additional hour. The mixture was cooled, the bis-(2-methoxyethyl) ether was evaporated under reduced pressure, and the residue crystallized from hexane to give a white solid in 65% yield based on the octadecane thiol.

Workup

  1. waitrocking was continued for an additional hour
  2. temperatureThe mixture was cooled
  3. customthe bis-(2-methoxyethyl) ether was evaporated under reduced pressure
  4. customthe residue crystallized from hexane
  5. customto give a white solid in 65% yield

Sources & evidence

ORD record
ord-4c11b15402834f9cb6dfb151772ba2e9
Source dataset
uspto-grants-1979_08
Patent number
US04165334

Reaction notes

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