Toluene → 2,2'-((1-Methylethylidene)bis(cyclohexane-4,1-diyloxymethylene))bisoxirane

HRID 373337

Reaktionsgleichung

Reaktionsgleichung von HRID 373337
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([CH:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)([CH3:10])[CH3:9])[CH2:4][CH2:3]1.[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl.[OH-:23].[Na+].[C:25]1([CH3:31])C=CC=C[CH:26]=1>[Sn](F)F.C1OCCOCCOCCOCCOCCOC1>[CH2:18]([O:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:8]([CH:11]2[CH2:12][CH2:13][CH:14]([O:17][CH2:31][CH:25]3[O:23][CH2:26]3)[CH2:15][CH2:16]2)([CH3:10])[CH3:9])[CH2:6][CH2:7]1)[CH:20]1[O:22][CH2:21]1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 94932Hydrogenated bisphenol a

Produkt 1

HCID 1145142,2'-((1-Methylethylidene)bis(cyclohexane-4,1-diyloxymethylene))bisoxiraneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24550StopKatalysatorHCID 2855718-Crown-6Katalysator

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

A reactor of the kind described in Example 8 is charged with 240.4 g (1.0 mol) of perhydrobisphenol A, 3.14 g (0.02 mol) of powdered tin difluoride and 5.28 g (0.02 mol) of 18-crown-6, and the charge is heated to 145° C., whereupon the educt melts. Then, with efficient stirring 152.12 ml (1.94 mol) of epichlorohydrin are added over 30 minutes. The reaction is allowed to continue for 12 hours, then cooled to 55° C., 250 ml of toluene are added and, then, at this temperature, 155.2 g (1.94 mol) of a 50% aqueous solution of sodium hydroxide are added dropwise with efficient stirring over 30 minutes. After stirring for 4.5 hours at 55°-60° C. and cooling to room temperature, the suspension is filtered and the filtrate is washed with toluene. The phases are separated, and the aqueous phase is extracted with 2×100 ml of ethyl acetate. The combined organic phases are washed with a small an amount of 10% KH2PO4 solution as possible and then with water until neutral, dried over magnesium sulfate and filtered. The filtrate is freed from solvent on a rotary evaporator under vacuum (bath temperature 70° C.). Yield: 330.8 g (94% of theory) of yellowish perhydrobisphenol A diglycidyl ether for which the following analytical values are obtained: epoxy value: 4.31 eq/kg (76% of theory); total chlorine content: 2.1%; hydrolysable chlorine content: 171 ppm.

Aufarbeitung

  1. customA reactor of the kind described in Example 8
  2. additionare added over 30 minutes
  3. temperaturecooled to 55° C.
  4. stirringAfter stirring for 4.5 hours at 55°-60° C.
  5. temperaturecooling to room temperature
  6. filtrationthe suspension is filtered
  7. washthe filtrate is washed with toluene
  8. customThe phases are separated
  9. extractionthe aqueous phase is extracted with 2×100 ml of ethyl acetate
  10. washThe combined organic phases are washed with a small an amount of 10% KH2PO4 solution as possible and then with water until neutral,
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. customThe filtrate is freed from solvent on a rotary evaporator under vacuum (bath temperature 70° C.)

Quellen und Nachweise

ORD-Eintrag
ord-cd95890d799f482ba8de15b6d97a1ad2
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162547

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