Potassium Iodide → 5-n-Dodecylthio-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole

HRID 440187

Reaktionsgleichung

Reaktionsgleichung von HRID 440187
Cl[C:2]1[CH:25]=[CH:24][C:5]2=[N:6][N:7]([C:9]3[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]=3[OH:23])[N:8]=[C:4]2[CH:3]=1.[CH2:26]([SH:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[CH2:26]([S:38][C:2]1[CH:25]=[CH:24][C:5]2=[N:6][N:7]([C:9]3[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]=3[OH:23])[N:8]=[C:4]2[CH:3]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 81951-DodecanethiolHCID 11430Potassium CarbonateHCID 774702,4-Di-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)phenol

Produkt 1

HCID 152503985-n-Dodecylthio-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a 3-liter three-necked flask equipped with stirrer, thermometer, nitrogen inlet and distillation set-up are charged 357.8 g (1 mole) of 5-chloro-(2-hydroxy-3,5-di-tert-butyl-phenyl)-2H-benzotriazole, available from CIBA-GEIGY Corp. as TINUVIN® 327, 216.8 g (1.05 mole) of n-dodecyl mercaptan and 600 mL of N,N-dimethylformamide (DMF). Then 73.9 g (0.54 moles) of potassium carbonate and 2 g of potassium iodide are added and the mixture heated for 20 hours at 150° C. under a nitrogen atmosphere. Any water which is liberated as a result of the reaction distills off as an azeotrope until the head-temperature reaches 132° C. After 20 hours at 150° C. the starting 2H-benzotriazole is totally consumed. With partial vacuum at 80°-100° C., most of the DMF is distilled off. To the resulting oil is added at 80° C. 1 L of toluene and 500 mL of water. The aqueous phase is drained off. The toluene solution is washed twice more with 500 mL water containing 1 mL of acetic acid. The organic solution is freed from residual water by azeotropic distillation until a clear solution is obtained. Under partial vacuum all but about 100 mL of toluene is distilled off at 70° C. The residue is diluted at 60° C. with 2 L of isopropanol and some product seeds are added The product gradually crystallizes and the mixture is slowly cooled to 10° C. The product is filtered off and washed with 300 mL of isopropanol to yield 490.4 g (93.6% of theory) of the title compound, mp. 62°-64° C.

Aufarbeitung

  1. customTo a 3-liter three-necked flask equipped with stirrer
  2. distillationthermometer, nitrogen inlet and distillation set-up
  3. customa result of the reaction
  4. distillationdistills off as an azeotrope until the head-temperature
  5. customreaches 132° C
  6. customAfter 20 hours at 150° C. the starting 2H-benzotriazole is totally consumed
  7. distillationWith partial vacuum at 80°-100° C., most of the DMF is distilled off
  8. additionTo the resulting oil is added at 80° C
  9. washThe toluene solution is washed twice more with 500 mL water containing 1 mL of acetic acid
  10. distillationThe organic solution is freed from residual water by azeotropic distillation until a clear solution
  11. customis obtained
  12. distillationUnder partial vacuum all but about 100 mL of toluene is distilled off at 70° C
  13. additionThe residue is diluted at 60° C. with 2 L of isopropanol
  14. additionsome product seeds are added The product
  15. customgradually crystallizes
  16. temperaturethe mixture is slowly cooled to 10° C
  17. filtrationThe product is filtered off
  18. washwashed with 300 mL of isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-6f98f19712fb40f4b0f2c81d815a3635
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05516914

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