ChemicalBook CAS DataBase List CYCLODODECYLAMINE

CYCLODODECYLAMINE synthesis

12synthesis methods

Product Name:CYCLODODECYLAMINE
CAS Number:1502-03-0
Molecular formula:C12H25N
Molecular Weight:183.33

Cyclododecylamine is produced by reduction of cyclododecanone oxime with sodium and an alcohol, by catalytic reduction of nitrocyclododecane with hydrogen, by Ritter reaction of cyclododecene with hydrocyanic acid, or by hydrogenation of cyclododecanone under amination conditions. The reaction of cyclododecylamine with propylene oxide leads to a product that can undergo cyclization to give the fungicide Dodemorph (BASF). The compound behaves chemically as a primary amine.

1724-39-6 Synthesis

1724-39-6
127 suppliers
$7.00/5g

1502-03-0
86 suppliers
$20.00/250mg

Yield: 1.427 g

Reaction Conditions:

with carbonylchlorohydrido(4,5-bis((diisopropylphosphino)methyl)acridine)ruthenium(II);ammonia in tert-Amyl alcohol at 20 - 170; under 11251.1 - 15001.5 Torr; for 48 h;Inert atmosphere;Autoclave;

Steps:

4 Example 4 Direct Single-Stage Amination of Cyclododecanol by Means of Ammonia Over a Ruthenium-Pincer Complex (Vliq/Vgas=0.3, According to the Invention)
Under an argon atmosphere, 1.843 g (10 mmol) of cyclododecanol, 0.030 g (0.05 mmol) of carbonylchlorohydrido[4,5-(di-i-propylphosphinomethylacridino)ruthenium(II)] as catalyst and 25 ml of 2-methyl-2-butanol as solvent are placed in the glass liner of a 100 ml Hastelloy autoclave.
The autoclave is closed, pressurized with 20 bar of argon and vented three times and again pressurized with 15 bar of argon. 2 g (117.6 mmol) of liquid ammonia are then introduced into the autoclave (overall V_liq/V_gas=0.3).
The reaction mixture is stirred for 10 minutes at room temperature (600 rpm), subsequently heated while stirring to an internal temperature of 170° C. and maintained at this temperature for 48 hours.
After cooling to room temperature, careful depressurization of the mixture and pressurization with 20 bar of argon three times with subsequent venting, the autoclave is opened, the reaction mixture filtered through kieselguhr and the filtrate is evaporated under reduced pressure on a rotary evaporator to remove the solvent.
The crude product obtained is purified by bulb tube distillation under reduced pressure.
This gives 1.427 g of cyclododecylamine (yield: 78% of theory; boiling range: 175-180° C. air bath temperature at 6 mbar).

References:

Evonik Degussa GmbH;Klasovsky, Florian;Pfeffer, Jan Christoph;Tacke, Thomas;Haas, Thomas;Martin, Andreas;Deutsch, Jens;Koeckritz, Angela US2013/165672, 2013, A1 Location in patent:Paragraph 0078

1724-39-6 Synthesis

1724-39-6
127 suppliers
$7.00/5g

1502-03-0
86 suppliers
$20.00/250mg