Water → HCID 87148504, compound

HRID 1182421Notes

Reaction equation

HRID 1182421 reaction equation
[CH2:1]([C:3]1[C:8]([NH2:9])=[C:7]([CH3:10])[C:6]([NH2:11])=[C:5]([CH2:12][CH3:13])[CH:4]=1)[CH3:2].O>[Pt].C(C(C)=O)C>[CH:1]([NH:11][C:6]1[C:5]([CH2:12][CH3:13])=[CH:4][C:3]([CH2:1][CH3:2])=[C:8]([NH:9][CH:5]([CH2:6][CH3:7])[CH3:12])[C:7]=1[CH3:10])([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 749794,6-Diethyl-2-methyl-1,3-benzenediamine

Product 1

HCID 87148504HCID 87148504, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
130 °C

Procedure

Diethyl(methyl)-1,3-benzenediamine, as a mixture of its 2,4-diethyl-6-methyl- and 4,6-diethyl-2-methyl-isomers (5 g; Ethacure® 100, Albemarle Corporation), Pt(S)/C (0.5 g), water (1 g) and methyl ethyl ketone (50 g) were charged into a 100 mL metal autoclave at 22° C. The autoclave was purged 3 times with 125 psig (9.63×105 Pa) of H2 at 22° C. The reaction mixture was then heated at 130° C. under 125 psig (9.63×105 Pa) of H2. After 30-45 minutes, H2 uptake was observed. The reaction mixture was stirred at 130° C. for 8 hours (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 (100° C. for 5 minutes at 10° C. per minute rate; final temperature, 270° C.). The GC data (normalization method) showed 100% conversion of diethyl(methyl)-1,3-benzenediamine, and an 88.8% yield of N,N′-di-sec-butyl-[diethyl(methyl)-1,3-benzenediamine].

Workup

  1. customThe autoclave was purged 3 times with 125 psig (9.63×105 Pa) of H2 at 22° C
  2. temperatureThe product mixture was cooled to 22° C.
  3. customdegassed
  4. custom100° C.
  5. customfor 5 minutes
  6. customtemperature, 270° C.

Sources & evidence

ORD record
ord-ebda351d44514fc4a9f7d4ed00f016c6
Source dataset
uspto-grants-2007_10
Patent number
US07288677B2

Reaction notes

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