CA2250770C - Procede de preparation d'un groupement cyano contenant des methylamines aromatiques - Google Patents
Procede de preparation d'un groupement cyano contenant des methylamines aromatiques Download PDFInfo
- Publication number
- CA2250770C CA2250770C CA002250770A CA2250770A CA2250770C CA 2250770 C CA2250770 C CA 2250770C CA 002250770 A CA002250770 A CA 002250770A CA 2250770 A CA2250770 A CA 2250770A CA 2250770 C CA2250770 C CA 2250770C
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- raney
- raney catalyst
- hydrogen
- aromatic
- 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 - Fee Related
Links
- 125000004093 cyano group Chemical group *C#N 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title abstract description 14
- -1 aromatic methylamines Chemical class 0.000 title description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 130
- 125000003118 aryl group Chemical group 0.000 claims abstract description 104
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 79
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 65
- 239000001257 hydrogen Substances 0.000 claims abstract description 65
- 239000002904 solvent Substances 0.000 claims abstract description 41
- 239000003513 alkali Substances 0.000 claims abstract description 15
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 12
- 239000010941 cobalt Substances 0.000 claims abstract description 12
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 64
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 44
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 29
- 229910052742 iron Inorganic materials 0.000 claims description 19
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 15
- 235000014413 iron hydroxide Nutrition 0.000 claims description 13
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 claims description 13
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229920006391 phthalonitrile polymer Polymers 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 64
- 238000006243 chemical reaction Methods 0.000 abstract description 49
- 230000004913 activation Effects 0.000 abstract description 26
- 230000008929 regeneration Effects 0.000 abstract description 21
- 238000011069 regeneration method Methods 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 125000002560 nitrile group Chemical group 0.000 description 18
- 239000012295 chemical reaction liquid Substances 0.000 description 15
- 238000004817 gas chromatography Methods 0.000 description 13
- LFIWXXXFJFOECP-UHFFFAOYSA-N 4-(aminomethyl)benzonitrile Chemical compound NCC1=CC=C(C#N)C=C1 LFIWXXXFJFOECP-UHFFFAOYSA-N 0.000 description 12
- 238000010813 internal standard method Methods 0.000 description 12
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 10
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000005456 alcohol based solvent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000005219 aminonitrile group Chemical group 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XFKPORAVEUOIRF-UHFFFAOYSA-N 3-(aminomethyl)benzonitrile Chemical compound NCC1=CC=CC(C#N)=C1 XFKPORAVEUOIRF-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003863 metallic catalyst Substances 0.000 description 2
- ZNPWYAMBOPRTHW-UHFFFAOYSA-N naphthalene-1,2-dicarbonitrile Chemical compound C1=CC=CC2=C(C#N)C(C#N)=CC=C21 ZNPWYAMBOPRTHW-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DMYCNEHFKBQXQL-UHFFFAOYSA-N 2-chloro-4-methylbenzene-1,3-dicarbonitrile Chemical compound CC1=CC=C(C#N)C(Cl)=C1C#N DMYCNEHFKBQXQL-UHFFFAOYSA-N 0.000 description 1
- FUXVXOPFTHRBNH-UHFFFAOYSA-N 2-chlorobenzene-1,4-dicarbonitrile Chemical compound ClC1=CC(C#N)=CC=C1C#N FUXVXOPFTHRBNH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- CUPCBVUMRUSXIU-UHFFFAOYSA-N [Fe].OOO Chemical compound [Fe].OOO CUPCBVUMRUSXIU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 description 1
- 229960003375 aminomethylbenzoic acid Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052804 chromium Chemical group 0.000 description 1
- 239000011651 chromium Chemical group 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910021519 iron(III) oxide-hydroxide Inorganic materials 0.000 description 1
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- CMDWPFFYPYYSEO-UHFFFAOYSA-N naphthalene-1,3-dicarbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CC(C#N)=C21 CMDWPFFYPYYSEO-UHFFFAOYSA-N 0.000 description 1
- BENSWQOUPJQWMU-UHFFFAOYSA-N naphthalene-1,4-dicarbonitrile Chemical compound C1=CC=C2C(C#N)=CC=C(C#N)C2=C1 BENSWQOUPJQWMU-UHFFFAOYSA-N 0.000 description 1
- WNDSQRGJJHSKCQ-UHFFFAOYSA-N naphthalene-1,5-dicarbonitrile Chemical compound C1=CC=C2C(C#N)=CC=CC2=C1C#N WNDSQRGJJHSKCQ-UHFFFAOYSA-N 0.000 description 1
- FTPHGLJOANEDML-UHFFFAOYSA-N naphthalene-1,6-dicarbonitrile Chemical compound N#CC1=CC=CC2=CC(C#N)=CC=C21 FTPHGLJOANEDML-UHFFFAOYSA-N 0.000 description 1
- KNBYJRSSFXTESR-UHFFFAOYSA-N naphthalene-2,3-dicarbonitrile Chemical compound C1=CC=C2C=C(C#N)C(C#N)=CC2=C1 KNBYJRSSFXTESR-UHFFFAOYSA-N 0.000 description 1
- ZBFVJRBOKDTSMO-UHFFFAOYSA-N naphthalene-2,6-dicarbonitrile Chemical compound C1=C(C#N)C=CC2=CC(C#N)=CC=C21 ZBFVJRBOKDTSMO-UHFFFAOYSA-N 0.000 description 1
- NNHXOKPHDUDDAK-UHFFFAOYSA-N naphthalene-2,7-dicarbonitrile Chemical compound C1=CC(C#N)=CC2=CC(C#N)=CC=C21 NNHXOKPHDUDDAK-UHFFFAOYSA-N 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
La présente invention concerne un procédé de préparation de cyanoarylméthylamine par hydrogénation de l'un uniquement des groupes cyano d'un dinitrile aromatique, ce qui permet la préparation de l'amine recherché avec un rendement élevé par réaction du dinitrile en conversion haute avec utilisation d'une petite quantité d'un catalyseur dans des conditions de réaction de basse température et de basse pression. Selon ce procédé, on n'utilise comme catalyseur pour la préparation de cyanoarylméthylamine à partir d'un dinitrile aromatique, qu'un seul des catalyseurs activés de Raney préparés par traitement de catalyseurs de Raney avec de l'hydrogène dans des solvants et des catalyseurs de Raney régénérés préparés par traitement de catalyseurs de Raney avec de l'hydrogène en présence d'alcalis dans des solvants. La quantité de catalyseurs de Raney activés à utiliser représente de préférence de 0,1 à 10 % de la masse, et de préférence de 0,5 à 5 % de la masse de dinitrile aromatique, la quantité de catalyseurs de Raney régénérés à utiliser représentant de préférence de 0,1 à 50 % de la masse, et de préférence de 0,5 à 20 % de la masse de dinitrile aromatique. Le catalyseur de Raney activé est de préférence du type contenant du nickel et/ou du cobalt et préparé par activation dans un solvant sous atmosphère d'hydrogène, le catalyseur de Raney régénéré étant de préférence d'un type préparé en soumettant à régénération au moyen d'hydrogène dans un solvant en présence d'un alcali un catalyseur de Raney qui a été utilisé pour la préparation de cyanoarylméthylamine à partir d'un dinitrile aromatique.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| WOPCT/JP97/00270 | 1997-02-04 | ||
| PCT/JP1997/000270 WO1998033766A1 (fr) | 1997-02-04 | 1997-02-04 | Procede de preparation de cyanoarylmethylamine |
| PCT/JP1998/000464 WO1998033767A1 (fr) | 1997-02-04 | 1998-02-04 | Procede de preparation de cyanoarylmethylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2250770A1 CA2250770A1 (fr) | 1998-08-06 |
| CA2250770C true CA2250770C (fr) | 2007-08-21 |
Family
ID=38434637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002250770A Expired - Fee Related CA2250770C (fr) | 1997-02-04 | 1998-02-04 | Procede de preparation d'un groupement cyano contenant des methylamines aromatiques |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2250770C (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1900428B1 (fr) | 2006-08-09 | 2016-01-06 | Mitsubishi Gas Chemical Company, Inc. | Procédé de production d'amines primaires et catalyseurs pour produire des amines primaires |
-
1998
- 1998-02-04 CA CA002250770A patent/CA2250770C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2250770A1 (fr) | 1998-08-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130204 |