CA1122981A - Preparation of stereoisomeric n-aralkyl-2,6-dimethyl-morpholine - Google Patents
Preparation of stereoisomeric n-aralkyl-2,6-dimethyl-morpholineInfo
- Publication number
- CA1122981A CA1122981A CA328,740A CA328740A CA1122981A CA 1122981 A CA1122981 A CA 1122981A CA 328740 A CA328740 A CA 328740A CA 1122981 A CA1122981 A CA 1122981A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- silver
- reaction
- hydrogen
- palladium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 28
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical class CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000005984 hydrogenation reaction Methods 0.000 claims description 18
- 229910052709 silver Inorganic materials 0.000 claims description 17
- 239000004332 silver Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 235000012239 silicon dioxide Nutrition 0.000 claims description 8
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 239000011572 manganese Substances 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 claims 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims 4
- 229910052748 manganese Inorganic materials 0.000 claims 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 1
- 150000001412 amines Chemical class 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001728 carbonyl compounds Chemical class 0.000 description 4
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- HNVIQLPOGUDBSU-PHDIDXHHSA-N (2r,6r)-2,6-dimethylmorpholine Chemical compound C[C@@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-PHDIDXHHSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000005932 reductive alkylation reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VLFBSPUPYFTTNF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-methylpropanal Chemical compound COC1=CC=C(CC(C)C=O)C=C1 VLFBSPUPYFTTNF-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- SWELZOZIOHGSPA-UHFFFAOYSA-N palladium silver Chemical compound [Pd].[Ag] SWELZOZIOHGSPA-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- PMGQZHMNKYVKJY-GOOCMWNKSA-N (2r,6s)-2,6-dimethyl-4-(3-phenylbutyl)morpholine Chemical compound C=1C=CC=CC=1C(C)CCN1C[C@H](C)O[C@H](C)C1 PMGQZHMNKYVKJY-GOOCMWNKSA-N 0.000 description 1
- MLNSDBJIMTXPBQ-GOOCMWNKSA-N (2s,6r)-4-[3-(4-methoxyphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C1=CC(OC)=CC=C1CC(C)CN1C[C@@H](C)O[C@@H](C)C1 MLNSDBJIMTXPBQ-GOOCMWNKSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PFOLDPUTKCIVJG-UHFFFAOYSA-N 2-(4-tert-butylphenyl)butanal Chemical compound CCC(C=O)C1=CC=C(C(C)(C)C)C=C1 PFOLDPUTKCIVJG-UHFFFAOYSA-N 0.000 description 1
- ROPNSYBZOVTZBB-UHFFFAOYSA-N 2-benzylbutanal Chemical compound CCC(C=O)CC1=CC=CC=C1 ROPNSYBZOVTZBB-UHFFFAOYSA-N 0.000 description 1
- SGVBCLGVIOFAFT-UHFFFAOYSA-N 2-methyl-3-(4-methylphenyl)propanal Chemical compound O=CC(C)CC1=CC=C(C)C=C1 SGVBCLGVIOFAFT-UHFFFAOYSA-N 0.000 description 1
- HEPHYCJJLAUKSB-UHFFFAOYSA-N 2-methyl-3-phenylpropanal Chemical compound O=CC(C)CC1=CC=CC=C1 HEPHYCJJLAUKSB-UHFFFAOYSA-N 0.000 description 1
- PLYTVAFAKDFFKM-UHFFFAOYSA-N 3,4-dimethylmorpholine Chemical class CC1COCCN1C PLYTVAFAKDFFKM-UHFFFAOYSA-N 0.000 description 1
- HQQPOVNESMNPNH-UHFFFAOYSA-N 3-(4-propan-2-ylphenyl)butanal Chemical compound CC(C)C1=CC=C(C(C)CC=O)C=C1 HQQPOVNESMNPNH-UHFFFAOYSA-N 0.000 description 1
- NKZPGPZCKPODMT-UHFFFAOYSA-N 3-(4-tert-butylphenyl)butanal Chemical compound O=CCC(C)C1=CC=C(C(C)(C)C)C=C1 NKZPGPZCKPODMT-UHFFFAOYSA-N 0.000 description 1
- MYHGOWDLVRDUFA-UHFFFAOYSA-N 3-phenylbutanal Chemical compound O=CCC(C)C1=CC=CC=C1 MYHGOWDLVRDUFA-UHFFFAOYSA-N 0.000 description 1
- QWNKGUFEJXENIX-UHFFFAOYSA-N 4-(4-tert-butylphenyl)butan-2-one Chemical compound CC(=O)CCC1=CC=C(C(C)(C)C)C=C1 QWNKGUFEJXENIX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- -1 hept&ne Chemical compound 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782830999 DE2830999A1 (de) | 1978-07-14 | 1978-07-14 | Verfahren zur herstellung von stereoisomeren n-aralkyl-2,6-dimethylmorpholinen |
| DEP2830999.1 | 1978-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1122981A true CA1122981A (en) | 1982-05-04 |
Family
ID=6044396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA328,740A Expired CA1122981A (en) | 1978-07-14 | 1979-05-30 | Preparation of stereoisomeric n-aralkyl-2,6-dimethyl-morpholine |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0007093B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5515463A (enrdf_load_stackoverflow) |
| AT (1) | ATE69T1 (enrdf_load_stackoverflow) |
| CA (1) | CA1122981A (enrdf_load_stackoverflow) |
| DE (2) | DE2830999A1 (enrdf_load_stackoverflow) |
| IL (1) | IL57336A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8017808B2 (en) | 2006-03-21 | 2011-09-13 | Basf Se | Process for preparing an amine |
| US8034978B2 (en) | 2006-05-31 | 2011-10-11 | Basf Se | Process for the preparation of an amine |
| US8163963B2 (en) | 2005-10-17 | 2012-04-24 | Basf Se | Process for continuous hydrogenation or hydrogenating amination |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4283534A (en) | 1979-04-11 | 1981-08-11 | Basf Aktiengesellschaft | Reductive alkylation of nitrogen heterocycles |
| ZW15780A1 (en) * | 1979-08-17 | 1981-03-18 | Hoffmann La Roche | Heterocyclic compounds |
| DE3105446A1 (de) * | 1981-02-14 | 1982-09-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von araliphatischen aldehyden und/oder aminen |
| DE3476386D1 (de) * | 1983-11-02 | 1989-03-02 | Beecham Group Plc | Morpholine derivatives |
| DE3421810A1 (de) * | 1984-06-12 | 1985-12-12 | Basf Ag, 6700 Ludwigshafen | Phenylalkylamine - bioregulatoren |
| GB8621790D0 (en) * | 1986-09-10 | 1986-10-15 | Ici Plc | Tertiary amine compounds |
| IL89997A0 (en) * | 1988-04-25 | 1989-12-15 | Lilly Co Eli | Propanamine derivatives |
| DE4009411A1 (de) * | 1990-03-23 | 1991-09-26 | Basf Ag | N-(3-phenyl-2-methylpropyl und -methylprop-2-enyl)-azaheterocyclen |
| EP1373232B1 (de) * | 2001-03-16 | 2005-11-23 | Basf Aktiengesellschaft | Verfahren zur herstellung von n-substituierten 2,6-dialkylmorpholinen |
| CA187259S (en) | 2017-09-28 | 2020-05-25 | Braun Gmbh | Handle for electric toothbrush |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790119A (fr) * | 1971-04-15 | 1973-04-13 | Basf Ag | Procede de preparation d'amines aliphatiques et cycloaliphatiques secondaires ou tertiaires. |
| AT354187B (de) * | 1976-11-22 | 1979-12-27 | Hoffmann La Roche | Fungizides mittel |
| DE2656747C2 (de) * | 1976-12-15 | 1984-07-05 | Basf Ag, 6700 Ludwigshafen | Morpholinderivate |
| DE2700680A1 (de) * | 1977-01-08 | 1978-07-20 | Basf Ag | Verfahren zur herstellung von n-substituierten morpholiniumsalzen |
-
1978
- 1978-07-14 DE DE19782830999 patent/DE2830999A1/de not_active Withdrawn
-
1979
- 1979-05-18 IL IL57336A patent/IL57336A/xx unknown
- 1979-05-30 CA CA328,740A patent/CA1122981A/en not_active Expired
- 1979-06-26 JP JP7978079A patent/JPS5515463A/ja active Granted
- 1979-07-11 EP EP79102377A patent/EP0007093B1/de not_active Expired
- 1979-07-11 AT AT79102377T patent/ATE69T1/de not_active IP Right Cessation
- 1979-07-11 DE DE7979102377T patent/DE2960376D1/de not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8163963B2 (en) | 2005-10-17 | 2012-04-24 | Basf Se | Process for continuous hydrogenation or hydrogenating amination |
| US8557985B2 (en) | 2005-10-17 | 2013-10-15 | Basf Se | Process for continuous hydrogenation or hydrogenating amination |
| US8017808B2 (en) | 2006-03-21 | 2011-09-13 | Basf Se | Process for preparing an amine |
| US8034978B2 (en) | 2006-05-31 | 2011-10-11 | Basf Se | Process for the preparation of an amine |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0007093B1 (de) | 1981-05-20 |
| JPS5515463A (en) | 1980-02-02 |
| EP0007093A1 (de) | 1980-01-23 |
| IL57336A0 (en) | 1979-09-30 |
| DE2830999A1 (de) | 1980-01-31 |
| ATE69T1 (de) | 1981-06-15 |
| JPH0321547B2 (enrdf_load_stackoverflow) | 1991-03-22 |
| IL57336A (en) | 1983-05-15 |
| DE2960376D1 (en) | 1981-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1122981A (en) | Preparation of stereoisomeric n-aralkyl-2,6-dimethyl-morpholine | |
| JP4448645B2 (ja) | 第２アミンの製造方法 | |
| US4212972A (en) | Preparation of cis-2,6-dimethylmorpholine | |
| US6982352B2 (en) | Process for preparing N-methyldialkylamines from secondary dialkylamines and formaldehyde | |
| CA1152070A (en) | Preparation of cis-2,6-dimethylmorpholine | |
| JPH0569108B2 (enrdf_load_stackoverflow) | ||
| CA1128938A (en) | Preparation of aralkylamines | |
| EP0012224B1 (de) | Verfahren zur Herstellung von Riechstoffgemischen | |
| DE2620445A1 (de) | Verfahren zur herstellung von glycinnitrilen | |
| US10100002B2 (en) | Method for separating N,N,N'-trimethylbisaminoethylether and/or N,N-dimethylbisaminoethylether from a mixture | |
| EP0449546B1 (en) | Process for the preparation of m-aminophenols from resorcinol | |
| US4326080A (en) | Process for the preparation of 4-amino-diphenylamines | |
| EP1117632A2 (en) | Process for the production of cyclopropanemethylamine | |
| US5430187A (en) | Method for manufacturing dibenzylamine | |
| DE19649946A1 (de) | Verfahren zur Herstellung von Aminen aus Olefinen an Bor-MCM-22 oder ERB-1 Zeolithen | |
| DE10110842A1 (de) | Verfahren zur Herstellung von n-Butylaminen | |
| KR0149511B1 (ko) | 레조르시놀로부터 m-아미노페놀을 제조하는 방법 | |
| KR100388881B1 (ko) | O-(2-히드록시알킬)-옥심의제조방법 | |
| JP3177350B2 (ja) | ジノニルジフェニルアミンの製造法 | |
| DE10030619A1 (de) | Verfahren zur Herstellung von Alkylaminen | |
| JP3091258B2 (ja) | 環状アルキレンイミンのｎ−アルキル化物の製造法 | |
| JP3254744B2 (ja) | オクタヒドロフェナジンを分離する方法 | |
| EP0051805A1 (de) | Verfahren zur Herstellung von aromatischen Aminen | |
| CA2111714A1 (en) | 2,3,4-trifluoro-n-ethylaniline and processes for its preparation | |
| JPH11292831A (ja) | Ｎ−アルキルアミン類の製造方法およびこれに用いる触媒 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |