Ammonia → Didodecylamine

HRID 888463Notes

Reaction equation

HRID 888463 reaction equation
C(O)CCCCC[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[H][H].[CH3:22][C:23]1[C:28]2COC(=O)[C:27]=2[C:26](O[C@@H]2O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]2O)=[C:25]([CH2:46]/[CH:47]=[C:48](/[CH2:50][CH2:51][C:52](O)=O)\C)C=1OC.[NH3:57]>>[CH2:52]([NH:57][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:51][CH2:50][CH2:48][CH2:47][CH2:46][CH2:25][CH2:26][CH2:27][CH2:28][CH2:23][CH3:22]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 8221Stearyl AlcoholHCID 6442661Mycophenolic acid glucuronide2×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 18157Didodecylamine

Procedure

A 500 mL autoclave of an electromagnetic induction rotary agitation type was charged with 150 g (0.55 mol) of stearyl alcohol and 3 g of the catalyst (G) produced in Preparation Example 6 (2.0% by mass on the basis of the raw alcohol), and then the contents of the autoclave were heated to 220° C. in a hydrogen atmosphere (0 MPaG) while stirring (at 1000 rpm). Then, while flowing ammonia and hydrogen through the autoclave at rates of 19.1 g (1.1 mol)/h and 2.6 L (0.12 mol)/h, respectively, so as to maintain the reaction pressure at a constant value of 2.0 MPaG, the reaction was conducted for 3 h. The resultant reaction product was filtered to remove the catalyst therefrom, and then subjected to gas chromatography to analyze a composition thereof. As a result, it was confirmed that the conversion of the raw alcohol was 96.0%, the selectivity to lauryl amine was 78.1%, the amount of dilauryl amine produced is 13.4%, and the amount of the other by-products produced was 7.6%.

Workup

  1. customproduced in Preparation Example 6 (2.0% by mass on the basis of the raw alcohol), and then the contents of the autoclave
  2. temperaturerespectively, so as to maintain
  3. customThe resultant reaction product
  4. filtrationwas filtered
  5. customto remove the catalyst

Sources & evidence

ORD record
ord-86e7d2b588ee4b06b3fa5e5cbef9b48a
Source dataset
uspto-grants-2012_08
Patent number
US08247611B2

Reaction notes

Loading…