2-Ethyl-1-butanol → 1,1,3,3-Tetraoctyl-1,3-bis(2-ethylbutyloxy)-distannoxane

HRID 1920530

Reaction equation

HRID 1920530 reaction equation
[CH2:1]([Sn:9](=[O:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:19]([CH:21]([CH2:24][CH3:25])[CH2:22][OH:23])[CH3:20]>>[CH2:1]([Sn:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([O:23][CH2:22][CH:21]([CH2:24][CH3:25])[CH2:19][CH3:20])[O:18][Sn:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[O:23][CH2:22][CH:21]([CH2:24][CH3:25])[CH2:19][CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 73582-Ethyl-1-butanolHCID 93563Dioctyltin oxide

Product 1

HCID 866321191,1,3,3-Tetraoctyl-1,3-bis(2-ethylbutyloxy)-distannoxaneYield 99%

Conditions

Temperature
25 °C

Procedure

893 g (2.48 mol) of di-n-octyl tin oxide (Sankyo Organic Chemicals Co., Ltd., Japan) and 2403 g (23.6 mol) of 2-ethyl-1-butanol were placed in a 5000 mL volumetric eggplant-shaped flask. The flask was attached to an evaporator to which was connected an oil bath equipped with a temperature controller, a vacuum pump and a vacuum controller. The purge valve outlet of the evaporator was connected to a line containing nitrogen gas flowing at normal pressure. After closing the purge valve of the evaporator to reduce pressure inside the system, the purge valve was opened gradually to allow nitrogen to flow into the system and return to a normal pressure. The oil bath temperature was set to about 165° C., the flask was immersed in the oil bath and rotation of the evaporator was started. After heating for about 40 minutes in the presence of atmospheric pressure nitrogen with the purge valve of the evaporator left open, distillation of 2-ethyl-1-butanol containing water began. After maintaining in this state for 7 hours, the purge valve was closed, pressure inside the system was gradually reduced, and excess 2-ethyl-1-butanol was distilled with the pressure inside the system at 74 to 25 kPa. After the fraction no longer appeared, the flask was taken out of the oil bath. After allowing the flask to cool to the vicinity of room temperature (25° C.), the flask was taken out of the oil bath, the purge valve was opened gradually and the pressure inside the system was returned to atmospheric pressure. 1114 g of reaction liquid were obtained in the flask. Based on the results of 119Sn-, 1H- and 13C-NMR analyses, 1,1,3,3-tetra-n-octyl-1,3-bis(2-ethylbutyloxy)distannoxane was confirmed to have been obtained at a yield of 99% based on di-n-octyl tin oxide. The same procedure was then repeated 12 times to obtain a total of 13380 g of 1,1,3,3-tetra-n-octyl-1,3-bis(2-ethylbutyloxy)distannoxane.

Workup

  1. customThe flask was attached to an evaporator to which
  2. customequipped with a temperature controller
  3. customThe purge valve outlet of the evaporator
  4. additioncontaining nitrogen gas
  5. customthe purge valve of the evaporator
  6. customwas set to about 165° C.
  7. customthe flask was immersed in the oil bath and rotation of the evaporator
  8. temperatureAfter heating for about 40 minutes in the presence of atmospheric pressure nitrogen with the purge valve of the evaporator
  9. waitleft open
  10. distillationdistillation of 2-ethyl-1-butanol
  11. additioncontaining water
  12. temperatureAfter maintaining in this state for 7 hours
  13. customthe purge valve was closed
  14. distillationexcess 2-ethyl-1-butanol was distilled with the pressure inside the system at 74 to 25 kPa
  15. custom1114 g of reaction liquid
  16. customwere obtained in the flask

Sources & evidence

ORD record
ord-978db9d334784eb699260c6bc4341ef4
Source dataset
uspto-grants-2012_05
Patent number
US08168812B2

Linked notes

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