Ammonia → HCID 18681395, compound

HRID 2081928Notes

Reaction equation

HRID 2081928 reaction equation
[F:1][C:2]([F:35])([CH2:31][CH2:32][C:33]#[N:34])[C:3]([F:30])([F:29])[C:4]([F:28])([F:27])[C:5]([F:26])([F:25])[C:6]([F:24])([F:23])[C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12].N.[H][H]>[Co].O1CCCC1>[F:1][C:2]([F:35])([CH2:31][CH2:32][CH2:33][NH2:34])[C:3]([F:29])([F:30])[C:4]([F:27])([F:28])[C:5]([F:25])([F:26])[C:6]([F:24])([F:23])[C:7]([F:21])([F:22])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 27525514,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-HenicosafluorotridecanenitrileHCID 178418361HCID 178418361, compound2×

Product 1

HCID 18681395HCID 18681395, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A one liter Hastelloy pressure vessel was charged with 126.1 g (0.22 mol) of 3-(perfluorodecyl)propionitrile (Du Pont), 20 g of Rainey cobalt, 50 g of anhydrous ammonia and 300 mL of tetrahydrofuran. The vessel was pressured to 800 psi with hydrogen and heated to 110° C. The hydrogen pressure was adjusted to 1500 psi and maintained for 20 hours. The vessel was cooled to room temperature and vented. The solution was decanted and the reaction vessel was rinsed with tetrahydrofuran. The combined solutions were filtered through Celite® and concentrated on a rotary evaporator at 50° C. The product was distilled through a Vigreux column to give 119.8 g of product, bp 78-80° C. at 1.2 mm as a waxy solid which melted at 53-55° C. The product was redistilled through an 8 in. Vigreux column to give 107.7 g of a center cut, bp 70° C. at 1.8 mm.

Workup

  1. temperaturemaintained for 20 hours
  2. temperatureThe vessel was cooled to room temperature
  3. customThe solution was decanted
  4. washthe reaction vessel was rinsed with tetrahydrofuran
  5. filtrationThe combined solutions were filtered through Celite®
  6. concentrationconcentrated on a rotary evaporator at 50° C
  7. distillationThe product was distilled through a Vigreux column

Sources & evidence

ORD record
ord-04cf45b6538f4f7e8570cca90093fd6f
Source dataset
uspto-grants-1993_02
Patent number
US05186985

Reaction notes

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