Preparation of an amine
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We claim:
1. A process for preparing an amine by reacting a primary or secondary alcohol, aldehyde or ketone with hydrogen and a nitrogen compound selected from the group consisting of ammoniaand primary and secondary amines in the presence of a catalyst whose preparation has involved precipitation of catalytically active components onto monoclinic, tetragonal or cubic zirconium dioxide, wherein the catalytically active composition of thecatalyst before treatment with hydrogen comprises from 20 to 65% by weight of oxygen-containing compounds of zirconium, calculated as ZrO.sub.2, from 1 to 30% by weight of oxygen-containing compounds of copper, calculated as CuO, from 15 to 50% by weightof oxygen-containing compounds of nickel, calculated as NiO, and from 15 to 50% by weight of oxygen-containing compounds of cobalt, calculated as CoO.
2. A process as claimed in claim 1, wherein the catalytically active components precipitated are salts of a metal selected from transition groups VIII and IB of the Periodic Table.
3. A process as claimed in claim 2, wherein the metal salts are basic salts which are sparingly soluble or insoluble in water.
4. A process as claimed in claim 2, wherein the salts are oxides, hydrated oxides, hydroxides, carbonates and/or hydrogencarbonates.
5. A process as claimed in claim 2, wherein the metal is selected from the group consisting of Fe, Go, Ni, Ru, Rh, Pd, Pt and Cu.
6. A process as claimed in claim 2, wherein the metal is selected from the group consisting of Cu, Ni and Co.
7. A process as claimed in claim 5, wherein the molar ratio of nickel to copper is greater than 1.
8. A process as claimed in claim 1, wherein the monoclinic, tetragonal or cubic zirconium dioxide contains one or more oxides of metals of transition groups IIIB or main group IIA of the Periodic Table.
9. A process as claimed in claim 1, wherein the reaction is carried out at from 80 to 300.degree. C.
10. A process as claimed in claim 1, wherein the reaction is carried out in the liquid phase at pressures of from 5 to 30 MPa or in the gas phase at pressures of from 0.1 to 40 MPa.
11. A process as claimed in claim 1 for preparing an amine of the formula I ##STR00008## where R.sup.1, R.sup.2 are each hydrogen (H), alkyl, cycloalkyl, alkoxyalkyl, dialkylaminoalkyl, aryl, aralkyl or alkylaryl, or together form--(CH.sub.2).sub.j--X--(CH.sub.2).sub.k--, R.sup.3, R.sup.4 are each hydrogen (H), alkyl, cycloalkyl, hydroxyalkyl, aminoalkyl, hydroxyalkylaminoalkyl, alkoxyalkyl, dialkylaminoalkyl, alkylaminoalkyl,R.sup.5--(OCR.sup.6R.sup.7CR.sup.8R.sup.9).sub.n--(OCR.sup.6R.sup.7), aryl, heteroaryl, aralkyl, heteroarylalkyl, alkylaryl, alkylheteroaryl or Y--(CH.sub.2).sub.m--NR.sup.5--(CH.sub.2).sub.q, or together form --(CH.sub.2).sub.1--X--(CH.sub.2).sub.m--,or R.sup.2 and R.sup.4 together form --(CH.sub.2).sub.1--X--(CH.sub.2).sub.m--, R.sup.5, R.sup.10 are each hydrogen (H), alkyl or alkylphenyl, R.sup.6, R.sup.7, R.sup.8, R.sup.9 are each hydrogen (H), methyl or ethyl, X is CH.sub.2, CHR.sup.5, oxygen(O), sulfur (S) or NR.sup.5, Y is N(R.sup.10).sub.2, hydroxy, C.sub.2-20-alkylaminoalkyl or C.sub.3-20-dialkylaminoalkyl, n is an integer from 1 to 30 and j, k, l, m, q are each an integer from 1 to 4, by reacting a primary or secondary alcohol of theformula II ##STR00009## or aldehyde or ketone of the formula VI or VII ##STR00010## with a nitrogen compound of the formula III ##STR00011##
12. The process as claimed in claim 11, wherein R.sup.1, R.sup.2 are each hydrogen (H), C.sub.1-20-alkyl, C.sub.3-12-cycloalkyl, C.sub.2-30-alkoxyalkyl, C.sub.3-30-dialkylaminoalkyl, aryl, C.sub.7-20-aralkyl or C.sub.7-20-alkylaryl, or togetherform --(CH.sub.2).sub.j--X--(CH.sub.2).sub.k--, R.sup.3, R.sup.4 are each hydrogen (H), C.sub.1-200-alkyl, C.sub.3-12-cycloalkyl, C.sub.1-20-hydroxyalkyl, C.sub.1-20-aminoalkyl, C.sub.2-20-hydroxyalkylaminoalkyl, C.sub.2-30-alkoxyalkyl,C.sub.3-30-dialkylaminoalkyl, C.sub.2-30-alkylaminoalkyl, R.sup.5--(OCR.sup.6R.sup.7CR.sup.8R.sup.9).sub.n--(OCR.sup.6R.sup.7), aryl, heteroaryl, C.sub.7-20-aralkyl, C.sub.4-20heteroarylalkyl, C.sub.7-20-alkylaryl, C.sub.4-20-alkylheteroaryl orY--(CH.sub.2).sub.m--NR.sup.5--(CH.sub.2).sub.q, or together form --(CH.sub.2).sub.1--X--(CH.sub.2).sub.m--, or R.sup.2 and R.sup.4 together form --(CH.sub.2).sub.1--X--(CH.sub.2).sub.m--, and R.sup.5, R.sup.10 are each hydrogen (H), C.sub.1-4-alkyl orC.sub.7-40-alkylphenyl.
Patent number:
7034186
View patent at USPTO
Filing date:
December 10, 2003
Issue date:
April 25, 2006
Inventors:
Johann-Peter Melder (Bohl-Iggelheim, DE)
Till Gerlach (Ludwigshafen, DE)
Frank Funke (Ludwigshafen, DE)
Assignee:
BASF Aktiengesellschaft (Ludwigshafen, DE)
Primary Examiner:
Brian Davis
Attorney, Agent or Firm:
Novak Druce DeLuca & Quigg, LLP
Current U.S. Classification: 564/397 564/398 564/401 564/402 564/403 564/472 564/473 564/479 564/480
