Methyl Ethyl Ketone → N,N'-di-sec-butyl-4,4'-methylenebis(2,6-diethylbenzeneamine)

HRID 1182413

Reaktionsgleichung

[CH2:1]([C:13]1[CH:18]=[C:17]([CH2:19][CH3:20])[C:16]([NH2:21])=[C:15]([CH2:22][CH3:23])[CH:14]=1)[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([NH2:10])=[C:4]([CH2:11][CH3:12])[CH:3]=1.[CH2:24]([C:26]([CH3:28])=O)[CH3:25]>[Pt].O1CCCC1>[CH:24]([NH:21][C:16]1[C:17]([CH2:19][CH3:20])=[CH:18][C:13]([CH2:1][C:2]2[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([NH:10][CH:1]([CH2:2][CH3:3])[CH3:13])=[C:4]([CH2:11][CH3:12])[CH:3]=2)=[CH:14][C:15]=1[CH2:22][CH3:23])([CH2:26][CH3:28])[CH3:25]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

4,4′-Methylenebis(2,6-diethylbenzeneamine) (3 g), Pt(S)/C (0.3 g), Amberlyst-15 (0.3 g), methyl ethyl ketone (25 g), and tetrahydrofuran (THF; 25 g) were charged into a 100 mL metal autoclave at 22° C. The closed autoclave was purged 3 times with 90 psig (7.22×105 Pa) of H2 at 22° C. The reaction mixture was then heated at 100-120° C. under 125 psig (9.63×105 Pa) of H2 for 5 hrs (until no further H2 uptake was observed). The product mixture was cooled to 22° C. and degassed. A diluted product sample was analyzed by GC (180° C. for 5 minutes at 10° C. per minute rate; final temperature, 270° C.). The GC data (normalization method) showed 100% conversion of 4,4′-methylenebis(2,6-diethylbenzeneamine), and an 86% yield of N,N′-di-sec-butyl-4,4′-methylenebis(2,6-diethylbenzeneamine).

Aufarbeitung

customThe closed autoclave was purged 3 times with 90 psig (7.22×105 Pa) of H2 at 22° C
temperatureThe product mixture was cooled to 22° C.
customdegassed
custom180° C.
customfor 5 minutes
customtemperature, 270° C.

Quellen und Nachweise

ORD-Eintrag: ord-94d5bf3beb2440be93a458b489cbdeef
Quelldatensatz: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07288677B2

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