Process for preparing monoisopropylamine

Details Process for preparing monoisopropylamine Process for preparing monoisopropylamine

2000-12-05

2003-05-13

Davis, Brian (Department: 1621)

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

Organic compounds

Amino nitrogen containing

Reexamination Certificate

active

06563004

ABSTRACT:

The present invention relates to a process for preparing monoisopropylamine (MIPA; (CH
3
)
2
CHNH
2
) by reacting acetone at elevated temperature and elevated pressure with ammonia and with hydrogen in the presence of a catalyst.
MIPA is an important organic intermediate which is required inter alia as precursor for preparing crop protection agents.
MIPA is prepared industrially by aminating hydrogenation of isopropanol or acetone with ammonia using catalysts.
DE-A-1 543 354 discloses the synthesis of MIPA by aminating hydrogenation of acetone in the presence of cobalt catalysts.
DT-A-1803 083, DT-A-1817 691, FR-A-159 0871, DE-A-18 03 083 and HU-A-47456 describe the preparation of MIPA by aminating hydrogenation of acetone in the presence of catalysts of the Raney nickel type.
DL-A-75086, DE-A-17 93 220, GB-A-1218 454, CN-A-1130 621, CS-A-185 962 and CS-A-239 445 relate to the preparation of MIPA by aminating hydrogenation of acetone in the presence of nickel/aluminum oxide catalysts.
DE-A-22 19 475 (loc. cit., Examples 10 to 12) describes the synthesis of MIPA from acetone in the presence of a nickel/chromium/kieselguhr catalyst.
EP-A-284 398 and CN-A-111 0629 relate to nickel catalysts doped with Ru or with Cr and Cu for preparing MIPA from acetone.
The earlier German application no. 19910960.5 of Mar. 12, 1999 discloses catalysts consisting of nickel, copper, molybdenum and zirconium dioxides for preparing MIPA by catalytic amination of acetone in the presence of hydrogen (loc. cit., Example 1). The selectivity of this conversion is only 82.3 to 95.2%.
The earlier German application no. 19859776.2 of Dec. 23, 1998 describes the preparation of MIPA from acetone and ammonia using a catalyst comprising copper and TiO
2
(loc. cit., Example 5).
The disadvantage of prior art processes is that the selectivities and yields in the aminating hydrogenation of acetone are too low. Even on use of a large molar excess of ammonia relative to acetone, as, for example, in GB-A-1218 454, Example 4, the maximum selectivity based on acetone is only 96.24% by weight.
EP-A-514 692 discloses catalysts containing copper, nickel and/or cobalt, zirconium oxide and/or aluminum oxide for the catalytic amination of alcohols in the gas phase with ammonia or primary amines and hydrogen.
EP-A-382 049 discloses catalysts which comprise oxygen-containing zirconium, copper, cobalt and nickel compounds, and processes for the hydrogenating amination of alcohols or carbonyl compounds. The preferred zirconium oxide content in these catalysts is from 70 to 80% by weight (loc. cit.: page 2, last paragraph; page 3, 3
rd
paragraph; Examples).
DE-A-19 53 263 discloses the use of Co-, Ni- and Cu-containing catalysts with Al
2
O
3
or SiO
2
as carrier material for preparing amines from alcohols.
The earlier European application no. 99111282.2 of Jun. 10, 1999 relates to a process for preparing amines by reacting primary or secondary alcohols with nitrogen compounds in the presence of catalysts comprising zirconium dioxide, copper, nickel and cobalt.
It is an object of the present invention to remedy the disadvantages of the prior art and improve the economics of previous processes for preparing MIPA by aminating hydrogenation of acetone with ammonia. It was intended to find catalysts which can be obtained easily or can be prepared in a technically simple manner and which permit the aminating hydrogenation of acetone to give MIPA to be carried out with a high acetone conversion, in particular acetone conversions of from 90 to 100%, high yield, high selectivity, in particular selectivities of from 96.5 to 100% (based on acetone), and high catalyst service life with, at the same time, high mechanical stability of the catalyst shaped article. The catalysts ought accordingly to have a high activity and a high chemical stability under the reaction conditions, and achieve the above object even on use of an only small molar excess of ammonia relative to acetone.
We have found that this object is achieved by a process for preparing monoisopropylamine (MIPA) by reacting acetone with ammonia and with hydrogen at elevated temperature and elevated pressure in the presence of a catalyst, wherein the catalytically active mass of the catalyst comprises, after its preparation and before the treatment with hydrogen,
from 20 to 90% by weight of aluminum oxide (Al
2
O
3
), zirconium dioxide (ZrO
2
), titanium dioxide (TiO
2
) and/or silicon dioxide (SiO
2
),
from 1 to 70% by weight of oxygen-containing compounds of copper, calculated as CuO,
from 1 to 70% by weight of oxygen-containing compounds of nickel, calculated as NiO, and
from 1 to 70% by weight of oxygen-containing compounds of cobalt, calculated as CoO.
In general, the catalysts employed in the process according to the invention are preferably in the form of catalysts which consist only of catalytically active mass and, where appropriate, a shaping auxiliary (such as, for example, graphite or stearic acid) if the catalyst is employed as shaped articles, that is to say contain no other catalytically inactive additives.
The catalytically active mass can be introduced after grinding as powder or as chips into the reaction vessel or, preferably, after grinding, mixing with molding auxiliaries, shaping and annealing, introduced as catalyst shaped articles—for example as tablets, beads, rings, extrudates (for example strands)—into the reactor.
The concentration data (in % by weight) of the components of the catalyst are in each case based—unless stated otherwise—on the catalytically active mass of the prepared catalyst after its last heat treatment and before the treatment with hydrogen.
The catalytically active mass of the catalyst after its last heat treatment and before the treatment with hydrogen is defined as the total of the masses of the catalytically active ingredients and the carrier materials and essentially comprises oxygen-containing compounds of aluminum, zirconium, titanium and/or silicon, oxygen-containing compounds of copper, oxygen-containing compounds of nickel and oxygen-containing compounds of cobalt.
The total of the abovementioned catalytically active ingredients and of the abovementioned carrier materials in the catalytically active mass, calculated as Al
2
O
3
, ZrO
2
, TiO
2
, SiO
2
, CuO, NiO and CoO, is normally from 70 to 100% by weight, preferably from 80 to 100% by weight, particularly preferably from 90 to 100% by weight, in particular from 95 to 100% by weight, very especially 100% by weight.
The catalytically active mass of the catalysts employed in the process according to the invention may further comprise one or more elements (oxidation state 0) or their inorganic or organic compounds selected from groups I A to VI A and I B to VII B and VIII of the Periodic Table.
Examples of such elements and their compounds are:
transition metals such as Mn or manganese oxides, Re or rhenium oxides, Cr or chromium oxides, Mo or molybdenum oxides, W or tungsten oxides, Ta or tantalum oxides, Nb or niobium oxides or niobium oxalate, V or vanadium oxides or vanadyl pyrophosphate, zinc or zinc oxides, silver or silver oxides, lanthanides such as Ce or CeO
2
or Pr or Pr
2
O
3
, alkali metal oxides such as Na
2
O, alkali metal carbonates such as Na
2
CO
3
and K
2
CO
3
, alkaline earth metal oxides such as SrO, alkaline earth metal carbonates such as MgCO
3
, CaCO
3
, BaCO
3
, phosphoric anhydrides and boron oxide (B
2
O
3
).
The catalytically active mass of the catalysts employed in the process according to the invention comprises, after preparation thereof and before the treatment with hydrogen,
from 20 to 90% by weight, preferably from 20 to 85% by weight, particularly preferably from 40 to 85% by weight, very particularly preferably from 50 to 85% by weight, of aluminum oxide (Al
2
O
3
), zirconium dioxide (ZrO
2
), titanium dioxide (TiO
2
) and/or silicon dioxide (SiO
2
),
from 1 to 70% by weight, preferably from 1 to 40% by weight, particularly preferably from 1 to 25% by weight, very particularly preferably from 1 to 15% by weight, of oxygen-containing compo

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