Process for producing a primary amine compound

Details Process for producing a primary amine compound Process for producing a primary amine compound

2000-04-19

2001-10-23

Richter, Johann (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

Reexamination Certificate

active

06307104

ABSTRACT:

TECHNICAL FIELD
The invention relates to both of a process for producing a primary amine compound and an alkylene oxide adduct thereto, given that the both are excellent in color.
PRIOR ARTS
An aliphatic primary amine compound and an alkylene oxide adduct thereto are important compounds in the field of products of household and industrial uses. In particular, they are used as starting materials for manufacturing surfactants, intermediates for fiber treatments and for bactericidal substances, and then active components of insecticides and of fiber softeners. In these applications, it is desirable that the amine compound and the adduct thereof are very pure and colorless substances.
Conventionally the primary amine compound can be obtained by hydrogenating a nitrile with a Raney nickel or a Raney cobalt as catalyst. Those methods are provided with a decreased selectivity of amine and an obtainable production yield not being sufficient. The color is not sufficient, either. The alkylene oxide adduct which is obtained from the primary amine compound as starting material of the adduct has also a color not being sufficient.
DISCLOSURE OF THE INVENTION
The purpose of the present invention is to provide a process for producing both of a primary amine and an alkylene oxide adduct thereto, given that the both are excellent in color, with high yield.
The present invention provides a process for producing a primary amine compound, comprising hydrogenating a nitrile compound in the presence of a Raney catalyst comprising 90 to 96% by weight of Ni, 3 to 9% by weight of Al and 0.5 to 3% by weight of Mo being based on the total of the atoms of Ni, Al and Mo. It then provides the process which further comprises adding an alkylene oxide to obtain an alkylene oxide adduct to the primary amine compound as defined above.
Incidentally, the Raney catalyst in the present invention may be an alloy having activity as catalyst for hydrogenating, which is obtained by eroding an alloy of a metal (A) having activity as catalyst for hydrogenating and another metal (B) by means of an eroding agent such as water, an alkali, an acid and the like to properly eliminate (B) (this procedure or operation is referred to development).
It is preferable that a weight ratio of Al/Ni ranges from 0.02 to 0.09; Mo/Ni ranges from 0.001 to 0.03; and Mo/(Ni+Al) ranges from 0.005 to 0.03.
The primary amine compound of the present invention is excellent in color and contains a reduced amount of non-amines. Further, it is preferable that the obtained amine compound has unsaturation.
The present invention further provides use of the amine compound as obtained by the process as defined above for producing an alkylene oxide adduct thereto.
DETAILED EXPLANATION OF INVENTION
A catalyst used in the present invention is a Raney catalyst comprising 90 to 96% by weight of Ni, 3 to 9% by weight of Al and 0.5 to 3 % by weight of Mo being based on the total of the atoms of Ni, Al and Mo. Outside the above shown ranges of Ni, Al and Mo, a reaction rate decreases, an amount of containable non-amines increases and the obtainable amine compound gets worse in color.
It is preferable that a weight ratio of Al/Ni ranges from 0.02 to 0.09, in particular from 0.03 to 0.08; Mo/Ni ranges from 0.001 to 0.03, in particular from 0.01 to 0.02; and Mo/(Ni+Al) ranges from 0.005 to 0.03, in the catalyst.
The catalyst used in the invention can be prepared, for example, by adding a molybdenum compound such as ammonium molybdate to an aqueous slurry of a commercially available Raney nickel catalyst and stirring to deposit the molybdenum compound on the Raney nickel catalyst or by etching an alloy of nickel, molybdenum and aluminum with an alkali.
In the present invention, the catalyst may be preferably added in an amount of 0.05 to 1.00% by weight to the nitrile.
The starting nitrile used in the present invention is preferably a saturated or unsaturated aliphatic nitrile compound having 8 to 36 carbon atoms. It includes, for example, caprylonitrile, lauronitrile, palmitonitrile, stearonitrile and oleonitrile.
Hydrogenation of the present invention may be preferably carried out under the hydrogen pressure of 0.05 to 50 Mpa at the reaction temperature of 60 to 160° C. The obtained primary amine compound may be purified, for example, by distillation.
An alkylene oxide adduct having an excellent color is obtained, when an alkylene oxide is added to the primary amine compound, as starting material, obtained by the above-mentioned process.
The alkylene oxide used in the present invention includes ethylene oxide, propylene oxide and butylene oxide. Ethylene oxide and propylene oxide are preferable. Ethylene oxide is particularly preferable. The mole number of added alkylene oxide is preferably 1 to 30 moles to 1 mole of the primary amine.
In the present invention, an addition reaction of an alkylene oxide can be carried out under reaction conditions for normal addition reaction of an alkylene oxide, preferably at the reaction temperature of 120 to 180° C.
As obviously disclosed by the following examples, the present invention provides a process which can unexpectedly improve productivity as compared with that of conventional arts and which can produce a primary amine compound, with high yield, having high quality such as being excellent in color and containing a reduced amount of contained non-amines. Further, in the case of producing unsaturated amine compounds, retention of the iodine value (as referred to IV, hereinafter) is improved but had been hardly improved. And then, unsaturated amine compounds can be produced with high selectivity and high yield. Furthermore, quality of derivatives formed by using the obtained amine compound becomes excellent in color. In particular, quality of amine derivatives obtained by adding an alkylene oxide thereto becomes as well.


REFERENCES:
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patent: 4248799 (1981-02-01), Drake
patent: 5840989 (1998-11-01), Cordier et al.
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Database CAPLUS on STN, Acc. No. 1991:679185, Besson et al., ‘Structure and catalytic properties in hydrogenation of valeronitrile of Raney nickel prepared from chromium and molybdenum doped nickel-aluminum (Ni2A13) alloys.’ Stud. Surf. Catal. (1991), 59 (Heterog. Catal. Fine Chem. 2) pp. 113-120 (Abstract).

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