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[0243] The following examples describe methods for hydrogenating dinitriles to produce diamines and methods for preparing catalysts for this hydrogenation reaction.
example 1
[0245] This example describes the conversion of methylglutaronitrile (MGN) to 2-methylpentamethylenediamine (MPMD). refer to figure 1 , the feed stream comprising MGN and fresh feed and recycle hydrogen and ammonia are passed to a series of four converters 42 , 44 , 46 and 48 . The MGN feed can have the following composition:
[0253] The pressure of the feed to first converter 42 may be at least 3500 psig (24,233 kPa), such as at least 4000 psig (27,680 kPa), such as at least 4500 psig (31,128 kPa). The temperature of the feed to the first converter may be at least 100°C, such as at least 105°C, such as at least 110°C. In the first converter 42, the reaction of hydrogen with MGN is an exothermic reaction. Thus, the temperature of the effluentstream exiting first converter ...
example 2
[0269] This example describes an embodiment in which a catalyst is formed by reducing iron oxide with hydrogen in the presence of ammonia.
[0270] see figure 2 , supply hydrogen from source 100. In this example, hydrogen source 104 is not used. The hydrogen supplied from source 100 comes from a hydrogen pipeline which has been purified by pressure swing adsorptionprocessing.
[0271] The hydrogen in source 100 is pressurized to a pressure of 200 to 400 psig (1,480 to 2,859 kPa), such as 250 to 350 psig (1,825 to 2,515 kPa), such as 300 psig (2,170 kPa). Hydrogen from source 100 is passed sequentially to preheater 110 via line 102 and line 108 . The heated hydrogen passes through line 112 to hydrogen / ammonia mixer 118 . The ammonia feed to hydrogen / ammonia mixer 118 is derived from ammonia source 114 . The ammonia in source 114 is anhydrousliquid ammonia, pressurized to a pressure of 300 to 500 psig (2,170 to 3,549 kPa), such as 350 to 450 psig (2,515 to 3,204 kPa), su...
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Abstract
The present invention discloses a process for the hydrogenation of dinitriles in the presence of liquid or supercritical ammonia to form diamines, in particular the preparation of hexamethylenediamine (HMD) from adiponitrile (ADN) and from methylglutaronitrile (MGN) Preparation of 2-methylpentamethylenediamine (MPMD). The heat generated in the hydrogenation reaction is used to supply heat to distill ammonia from a liquid comprising ammonia and diamines.
Description
[0001] Cross References to Related Applications [0002] This application claims the priority filing date of US Provisional Application No. 61 / 984,283, filed April 25, 2014, the disclosure of which is expressly incorporated herein by reference in its entirety. technical field [0003] The present invention relates to a process for the preparation of a catalyst and to a hydrogenation process in which the catalyst is effective. More specifically, this invention relates to the catalytic hydrogenation of organonitriles in the presence of heterogeneous iron catalysts. Examples of such reactions include the hydrogenation of adiponitrile to hexamethylenediamine and the hydrogenation of methylglutaronitrile (especially 2-methylglutaronitrile) to 2-methylpentamethylenediamine. Background technique [0004] Methods are known for the hydrogenation of compounds containing nitrile groups to amines. The hydrogenation of dinitriles to the corresponding diamines (specifically, the hydrog...
Claims
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