Sodium Sulfide → 3,14-Dioxa-8,9-dithia-4,13-disilahexadecane, 4,4,13,13-tetraethoxy-

HRID 991955Notes

Reaction equation

HRID 991955 reaction equation
[S-2:1].[Na+].[Na+].[S].Cl[CH2:6][CH2:7][CH2:8][Si:9]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]>C(O)C>[CH2:11]([O:10][Si:9]([CH2:8][CH2:7][CH2:6][S:1][S:1][CH2:6][CH2:7][CH2:8][Si:9]([O:16][CH2:17][CH3:18])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH3:12]

Participants

5

Reactant 3

HCID 14804Sodium Sulfide4×HCID 78771(3-Chloropropyl)triethoxysilaneHCID 5362487Sulfur

Product 1

HCID 925063,14-Dioxa-8,9-dithia-4,13-disilahexadecane, 4,4,13,13-tetraethoxy-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

17.8 kg of virtually anhydrous sodium sulfide are mixed with 190 l of ethanol and added to an enameled 500 l capacity reactor. This is followed by the addition through a fine nozzle of 13.85 kg of sulfur in molten form. The mixture is heated to 50° C. and 190 l of 3-chloropropyltriethoxysilane are metered in within 10 minutes. On account of the exothermic reaction the temperature of the reactor contents rises to 74° C. A further 4.45 kg of virtually anhydrous sodium sulfide are added at this temperature. Three further portions of sodium sulfide are added at 5 minute intervals (i.e. each 5 minutes), the temperature of the reactor contents rising to 82° C. After completion of the sodium sulfide addition the reaction mixture is kept for 1.5 hours at 82-83° C. and the sodium chloride that has precipitated is separated after cooling the mixture. A yellow product is obtained after evaporating the reaction mixture in vacuo and renewed fine filtration. HPLC analysis confirms the presence of a product with a mean polysulfane chain length of 2.

Workup

  1. additionadded to an enameled 500 l capacity reactor
  2. customare metered in within 10 minutes
  3. customOn account of the exothermic reaction the temperature of the reactor contents
  4. customrises to 74° C
  5. customrising to 82° C
  6. customthe sodium chloride that has precipitated
  7. customis separated
  8. temperatureafter cooling the mixture
  9. customA yellow product is obtained
  10. customafter evaporating the reaction mixture in vacuo
  11. filtrationfiltration

Sources & evidence

ORD record
ord-bdddaa50fe714a9893bdfe247ed5b474
Source dataset
uspto-grants-2002_10
Patent number
US06465672B2

Reaction notes

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