Hydrogen Peroxide → Tinuvin 123

HRID 1261748

Reaktionsgleichung

Reaktionsgleichung von HRID 1261748
[C:1]([O:25][CH:26]1[CH2:31][C:30]([CH3:33])([CH3:32])[N:29]([OH:34])[C:28]([CH3:36])([CH3:35])[CH2:27]1)(=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:20])([CH3:19])[N:16]([OH:21])[C:15]([CH3:23])([CH3:22])[CH2:14]1)=[O:11].OO.C(=O)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)(C)(C)C.C(O)(=O)C>[C:1]([O:25][CH:26]1[CH2:27][C:28]([CH3:36])([CH3:35])[N:29]([O:34][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH3:40])[C:30]([CH3:33])([CH3:32])[CH2:31]1)(=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:14][C:15]([CH3:22])([CH3:23])[N:16]([O:21][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:17]([CH3:19])([CH3:20])[CH2:18]1)=[O:11]

Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 31289NonanalHCID 11272241Bis(1-hydroxy-2,2,6,6-tetramethyl-4-piperidinyl)decandioate

Produkt 1

HCID 3592789Tinuvin 123

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 22595558Toluene tert-butyl alcoholLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

10.0 g Bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate (Prostab 5415, commercial product of Ciba Specialty Chemicals Inc.) are dissolved in 40 ml toluene/tert-butanol (2:1) and 8 g 50% aqueous hydrogen peroxide are added, followed by 18 ml nonanal, 0.1 ml acetic acid and 0.15 g CuCl2. The reaction mixture is stirred for 2 h at 25-25° C. and afterwards for 10 h at 40° C. The mixture is poured into 100 ml 0.1 N NaOH and subsequently extracted with methylene chloride. The organic phase is washed twice with water and then with sat. sodium chloride solution and dried over sodium sulfate. The organic phase is removed in vacuo and the residue subjected to column chromatography on silica gel to afford 5.4 g of product.

Aufarbeitung

  1. extractionsubsequently extracted with methylene chloride
  2. washThe organic phase is washed twice with water
  3. dry with materialwith sat. sodium chloride solution and dried over sodium sulfate
  4. customThe organic phase is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f499ab08a37b4d85b2efc98f72897fe2
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471031B2

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