2,3-Diaminotoluene → 1,1-Diphenylethane
Reaction equation
NC1C(N)=C(C)C=CC=1.N[CH:11]([CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)N.NC1C=CC(C(C)C2C=CC=CC=2)=C(N)C=1N>>[CH3:11][CH:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
Procedure
3(a) An aromatic polyamine mixture made up of 2.6% of diaminotoluene (isomer mixture), 6.2% of diaminomethyl diphenylmethane (isomer mixture containing more than 90% of diamines of the type containing one amino substituent on each aromatic ring) and 91.2% of triamino-methyl diphenyl methane (isomer mixture containing more than 90% of triamines with one amino group on the unsubstituted aromatic ring and two amino groups on the methyl-substitued aromatic ring) was obtained by the nitration of methyl diphenyl methane, followed by catalytic hydrogenation using Raney nickel in accordance with European Patent Application No. 46,917. 350 g of this polyamine mixture were hydrogenated at 200° C./275 bars in accordance with Example 1(a) in the presence of 35 g of ruthenium (5%)/aluminum oxide supported catalyst and 35 g of ammonia in a 0.7 liter stirrer-equipped autoclave. After distillation twice, the hydrogenation product which was 91% triaminomethyl dicyclohexyl methane corresponding to formula (I) (R=CH3), and 9% diaminomethyl dicyclohexyl methane, was isolated in a yield of 69.2 g (B.p. 132°-148° C./0.1 mbar).
Sources & evidence
- ORD record
- ord-27f112caf71143eeb6ce12181c148333
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04675437
Reaction notes
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