Hydrochloric Acid → [(Octylsilanetriyl)tri(propane-3,1-diyl)]tris(tridodecylsilane)

HRID 1494682노트

반응식

HRID 1494682 반응식
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:15]([Si:23]([CH2:38][CH2:39][CH2:40][Si:41](Cl)(Cl)Cl)([CH2:31][CH2:32][CH2:33][Si:34](Cl)(Cl)Cl)[CH2:24][CH2:25][CH2:26][Si:27](Cl)(Cl)Cl)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C[Li].Cl>CCOCC.O1CCCC1>[CH2:15]([Si:23]([CH2:38][CH2:39][CH2:40][Si:41]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:31][CH2:32][CH2:33][Si:34]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:24][CH2:25][CH2:26][Si:27]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 19828807n-Octyl-tris-[3-(trichlorosilyl)propyl]silane2회HCID 178418348HCID 178418348, 화합물HCID 178443215HCID 178443215, 화합물3회

생성물 1

HCID 19828808[(Octylsilanetriyl)tri(propane-3,1-diyl)]tris(tridodecylsilane)수율 43.6%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

Under a strong nitrogen flow, into a 2 L three-neck round bottom flask equipped with rubber septum, reflux condenser, nitrogen bypass inlet, and magnetic stirring bar were introduced freshly distilled tetrahydrofuran (350 Ml) and n-dodecylmagnesium bromide (800 Ml, 1.0M in diethyl ether, 800 mmol). In an inert atmosphere enclosure, into a 500 Ml addition funnel was added n-octyl-tris-[3-(trichlorosilyl)propyl]silane (30.0 g, 44.7 mmol, prepared by the procedure described in Example 1, Step (b)). The addition funnel was attached to the flask containing n-dodecylmagnesium bromide, and n-octyl-tris-[3-(trichlorosilyl)propyl]silane was added to the n-dodecylmagnesium bromide solution over a period of 45 minutes. The reaction was only slightly exothermic. The reaction mixture was heated at reflux temperature for 186 hours, then cooled to room temperature, and an ether solution of methyllithium (50 Ml, 1.5M) was added. The reaction mixture was heated at reflux temperature again for an additional 24 hours. After it was cooled in an ice-water bath, hydrochloric acid (500 Ml, 1.2N) was cautiously added. The reaction mixture separated into two layers on standing. The aqueous layer was extracted with diethyl ether (2×200 Ml). The organic layers were combined, washed once with water (200 Ml), and dried over magnesium sulfate, and the solvent removed under reduced pressure. Purification by silica gel column chromatography yielded 36.8 g (43.6%) of n-octyl-tris-[3-(tridodecylsilyl)propyl]silane. This tetrasilahydrocarbon had a kinematic viscosity of 105 centistokes at 40° C., a kinematic viscosity of 17.5 centistokes at 100° C., and a viscosity index of 183. Onset of volatilization under 0.43 mm Hg pressure, based on the thermogravimetric analysis, was at 285° C.

후처리

  1. customUnder a strong nitrogen flow, into a 2 L three-neck round bottom flask equipped with rubber septum
  2. temperaturereflux condenser
  3. additionIn an inert atmosphere enclosure, into a 500 Ml addition funnel
  4. customprepared by the procedure
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux temperature for 186 hours
  7. temperatureThe reaction mixture was heated
  8. temperatureat reflux temperature again for an additional 24 hours
  9. temperatureAfter it was cooled in an ice-water bath
  10. customThe reaction mixture separated into two layers on standing
  11. extractionThe aqueous layer was extracted with diethyl ether (2×200 Ml)
  12. washwashed once with water (200 Ml)
  13. dry with materialdried over magnesium sulfate
  14. customthe solvent removed under reduced pressure
  15. customPurification by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3dc2baa76513438fab45a5fe312f3040
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05026893

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