DE2344509A1 - Hydrierungsverfahren - Google Patents
HydrierungsverfahrenInfo
- Publication number
- DE2344509A1 DE2344509A1 DE19732344509 DE2344509A DE2344509A1 DE 2344509 A1 DE2344509 A1 DE 2344509A1 DE 19732344509 DE19732344509 DE 19732344509 DE 2344509 A DE2344509 A DE 2344509A DE 2344509 A1 DE2344509 A1 DE 2344509A1
- Authority
- DE
- Germany
- Prior art keywords
- ruthenium
- catalyst
- hydrogenation
- unsaturated
- hydrogenated
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 27
- 230000008569 process Effects 0.000 title description 7
- 230000036571 hydration Effects 0.000 title 1
- 238000006703 hydration reaction Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 36
- 238000005984 hydrogenation reaction Methods 0.000 claims description 22
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 18
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims description 17
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical group CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 150000003303 ruthenium Chemical class 0.000 claims description 11
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052707 ruthenium Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- ZEBFPAXSQXIPNF-OLQVQODUSA-N (2r,5s)-2,5-dimethylpyrrolidine Chemical compound C[C@H]1CC[C@@H](C)N1 ZEBFPAXSQXIPNF-OLQVQODUSA-N 0.000 claims description 3
- 150000001717 carbocyclic compounds Chemical class 0.000 claims description 3
- RZADCXOVFWAPGD-UHFFFAOYSA-K [Ru](Cl)(Cl)Cl.[Ru] Chemical compound [Ru](Cl)(Cl)Cl.[Ru] RZADCXOVFWAPGD-UHFFFAOYSA-K 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 239000003518 caustics Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- OUYLXVQKVBXUGW-UHFFFAOYSA-N 2,3-dimethyl-1h-pyrrole Chemical compound CC=1C=CNC=1C OUYLXVQKVBXUGW-UHFFFAOYSA-N 0.000 description 4
- -1 heterocyclic hydrocarbons Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000003822 preparative gas chromatography Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PXHHIBMOFPCBJQ-UHFFFAOYSA-N 1,2-dimethylpyrrolidine Chemical compound CC1CCCN1C PXHHIBMOFPCBJQ-UHFFFAOYSA-N 0.000 description 2
- HJDUCMRBFKTGNO-UHFFFAOYSA-N 2,5-dimethyl-3,4-dihydro-2h-pyrrole Chemical compound CC1CCC(C)=N1 HJDUCMRBFKTGNO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 150000003235 pyrrolidines Chemical class 0.000 description 2
- 150000003236 pyrrolines Chemical class 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- ZEBFPAXSQXIPNF-PHDIDXHHSA-N (2r,5r)-2,5-dimethylpyrrolidine Chemical compound C[C@@H]1CC[C@@H](C)N1 ZEBFPAXSQXIPNF-PHDIDXHHSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- ZEBFPAXSQXIPNF-UHFFFAOYSA-N 2,5-dimethylpyrrolidine Chemical compound CC1CCC(C)N1 ZEBFPAXSQXIPNF-UHFFFAOYSA-N 0.000 description 1
- WGTDLPBPQKAPMN-MDZDMXLPSA-N 2-[2-[(e)-heptadec-8-enyl]-4,5-dihydroimidazol-1-yl]ethanol Chemical compound CCCCCCCC\C=C\CCCCCCCC1=NCCN1CCO WGTDLPBPQKAPMN-MDZDMXLPSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 235000008098 Oxalis acetosella Nutrition 0.000 description 1
- 240000007930 Oxalis acetosella Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XJBVBGUCNBMKIH-UHFFFAOYSA-N alumane;ruthenium Chemical compound [AlH3].[Ru] XJBVBGUCNBMKIH-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- SZURGOUDEUXAPN-UHFFFAOYSA-N pyrrolidine;hydrate Chemical compound O.C1CCNC1 SZURGOUDEUXAPN-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 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
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/10—Chlorides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/10—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of aromatic six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
- C07C2527/13—Platinum group metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28609572A | 1972-09-05 | 1972-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2344509A1 true DE2344509A1 (de) | 1974-03-21 |
Family
ID=23097048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732344509 Pending DE2344509A1 (de) | 1972-09-05 | 1973-09-04 | Hydrierungsverfahren |
Country Status (11)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2526782A1 (fr) * | 1982-05-14 | 1983-11-18 | Metaux Precieux Cie | Procede de preparation de chlorure de ruthenium et catalyseur obtenu a partir de ce chlorure |
| JPWO2007063974A1 (ja) * | 2005-12-02 | 2009-05-07 | 財団法人名古屋産業科学研究所 | 芳香環化合物の芳香環への水素添加方法 |
-
1973
- 1973-09-03 AU AU59915/73A patent/AU5991573A/en not_active Expired
- 1973-09-04 GB GB4153573A patent/GB1393659A/en not_active Expired
- 1973-09-04 IT IT52331/73A patent/IT997527B/it active
- 1973-09-04 ZA ZA736048A patent/ZA736048B/xx unknown
- 1973-09-04 SU SU1957941A patent/SU489320A3/ru active
- 1973-09-04 FR FR7331841A patent/FR2197832B1/fr not_active Expired
- 1973-09-04 BE BE135292A patent/BE804429A/xx unknown
- 1973-09-04 DE DE19732344509 patent/DE2344509A1/de active Pending
- 1973-09-04 JP JP48098956A patent/JPS4969631A/ja active Pending
- 1973-09-04 NL NL7312230A patent/NL7312230A/xx unknown
- 1973-09-04 DD DD173269A patent/DD106340A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2197832A1 (enrdf_load_stackoverflow) | 1974-03-29 |
| ZA736048B (en) | 1974-10-30 |
| GB1393659A (en) | 1975-05-07 |
| AU5991573A (en) | 1975-03-06 |
| FR2197832B1 (enrdf_load_stackoverflow) | 1977-02-25 |
| SU489320A3 (ru) | 1975-10-25 |
| JPS4969631A (enrdf_load_stackoverflow) | 1974-07-05 |
| DD106340A5 (enrdf_load_stackoverflow) | 1974-06-12 |
| BE804429A (fr) | 1974-03-04 |
| NL7312230A (enrdf_load_stackoverflow) | 1974-03-07 |
| IT997527B (it) | 1975-12-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1948566C3 (de) | Verfahren zur Herstellung von Di (4 aminocyclohexyl) methan durch kata lytische Hydrierung von Di (4 amino phenyl)-methan | |
| DE1667193A1 (de) | Verfahren zur katalytischen Umwandlung von aliphatischen Alkoholen,Aminoalkoholen oder deren Mischungen,Katalysatoren zur Durchfuehrung des Verfahrens und ein Verfahren zur Herstellung derselben | |
| EP0170182B1 (de) | Verfahren zur Gewinnung von 2-Butenen aus 1-Buten und gegebenenfalls 2-Butene enthaltenden C4-Kohlenwasserstoffgemischen | |
| EP1081130B1 (de) | Verfahren zur Herstellung von Alkanolaminen mit verbesserter Farbqualität | |
| DE2431242C3 (de) | 2,7,10,15,18,23-Hexamethyltetracosan und Verfahren zu seiner Herstellung | |
| DE1593293C3 (de) | Verfahren zum Ändern des Isomerenverhältnisses eines Stereoisomerengemisches von 4,4'-Methylen-di (cyclohexylamin) | |
| DE2050908C2 (de) | Verfahren zur Herstellung von Weißöl | |
| DE1620191C3 (de) | Verfahren zur Herstellung von am Stickstoff substituierten Derivaten des alpha-Pyrrolidons | |
| EP0125415B1 (de) | Verfahren zur Herstellung von Pyrrolen | |
| DE2811722C2 (enrdf_load_stackoverflow) | ||
| DE2626676A1 (de) | Verfahren zur herstellung von 2-pyrrolidon | |
| DE2407096A1 (de) | Hydrierungsverfahren mit metallhydroxydkatalysatoren der gruppe viii, die keine traeger enthalten | |
| EP0230988A2 (de) | Verfahren zur Herstellung von 6-Aminocapronsäureestern | |
| DE68901742T2 (de) | Verfahren zur herstellung von gamma-butyrolacton. | |
| DE2344509A1 (de) | Hydrierungsverfahren | |
| EP0066212B1 (de) | Verfahren zur katalytischen Hydrierung von Di-(4-aminophenyl)methan | |
| DE1593289C3 (de) | Katalytisches Verfahren zum Hydrieren von aromatischen Verbindungen | |
| DE2133414C3 (de) | Verfahren zur Herstellung alkylidensubstituierter Norbornene | |
| DE3003731A1 (de) | Verfahren zur hydrierung von aromatischen bis-methylaminen | |
| EP4359372A1 (de) | Hydrierung von estern zu alkoholen in gegenwart eines mn-pnn-komplexes | |
| DE2626675A1 (de) | Verfahren zur herstellung von 2-pyrrolidon | |
| EP0142070B1 (de) | Verfahren zur Herstellung von N-Methylhomoveratrylamin | |
| DE2813162C3 (de) | Verfahren zur Herstellung von N-Methylpyrrolidin | |
| DE19626123A1 (de) | Verfahren zur Herstellung von Pyrrolidonen | |
| DE3020298C2 (de) | Verfahren zur Herstellung von 2,2,4,5,5-Pentamethyl-3-formyl-3-pyrrolin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |