ChemicalBook CAS DataBase List Dibutylamine

Dibutylamine synthesis

10synthesis methods

Product Name:Dibutylamine
CAS Number:111-92-2
Molecular formula:C8H19N
Molecular Weight:129.24

n-Dibutylamine is prepared by two major methods. The first involves passing ammonia and butanol over an alumina or silica catalyst at a temperature of 300-500°C and under pressure. The second method employs passing ammonia, butanol, and hydrogen over a dehydrogenation catalyst. In each instance the resulting mixtures are separated by continuous distillation and extraction (Schweizer et al 1978). n-Dibutylamine can also be prepared from butyl bromide and ammonia or by reaction of butyl chloride and ammonia (HSDB 1989). The amine also is naturally present in food (Neurath et al 1977) and its emissions are produced in soil and sewage. The amine is also found in the expired air of normal, healthy, nonsmoking adults (Krotoszynski et al 1979).
N-Nitrosamines and their precursors including n-dibutylamine are present in rubber products in which the accelerators and stabilizers used in the vulcanization process were derived from dialkylamines. Analysis of a single extraction of rubber nipples and baby pacifiers with artificial saliva (containing sodium nitrite) showed n-dibutylamine levels up to 3890 p.p.b. and N-nitrosodibutylamine concentrations as high as 427 p.p.b. (Thompson et al 1984).

6287-40-7 Synthesis

6287-40-7
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111-92-2
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Yield:111-92-2 97%

Reaction Conditions:

with ammonia in 1,2-dichloro-benzene at 20;

Steps:

D

D) Recovery of the Secondary Amine; The recovery of the dibutylamine from the reaction mixture from C) was accomplished initially by filtration removal of the salt formed in C). The solid was slurried in dichlorobenzene, with addition of about 90% by weight of solvent. The resulting slurry was reacted with ammonia gas (20 liters/h) in a flask at 20° C., with thorough mixing by means of a stirrer, to form the amine and ammonium chloride. The yield of dibutylamine formed, based on salt, was 97%.

References:

US2013/6013,2013,A1 Location in patent:Page/Page column 6

109-74-0 Synthesis