DE2435818C3 - Verfahren zur Herstellung aromatischer Diamine - Google Patents
Verfahren zur Herstellung aromatischer DiamineInfo
- Publication number
- DE2435818C3 DE2435818C3 DE2435818A DE2435818A DE2435818C3 DE 2435818 C3 DE2435818 C3 DE 2435818C3 DE 2435818 A DE2435818 A DE 2435818A DE 2435818 A DE2435818 A DE 2435818A DE 2435818 C3 DE2435818 C3 DE 2435818C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- catalyst
- solvent
- water
- hydrogen
- 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
- 238000000034 method Methods 0.000 title claims description 12
- 150000004984 aromatic diamines Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000003054 catalyst Substances 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 16
- 229910052763 palladium Inorganic materials 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- CVYZVNVPQRKDLW-UHFFFAOYSA-N 2,4-dinitroanisole Chemical compound COC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O CVYZVNVPQRKDLW-UHFFFAOYSA-N 0.000 description 5
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- NQHVJMJEWQQXBS-UHFFFAOYSA-N 4-ethoxybenzene-1,3-diamine Chemical compound CCOC1=CC=C(N)C=C1N NQHVJMJEWQQXBS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- -1 dinitro compound Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- OTANELYCMMCQIT-UHFFFAOYSA-N 1-ethoxy-2,3-dinitrobenzene Chemical compound CCOC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O OTANELYCMMCQIT-UHFFFAOYSA-N 0.000 description 1
- YSOKMOXAGMIZFZ-UHFFFAOYSA-N 2,4-dinitrophenetole Chemical compound CCOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YSOKMOXAGMIZFZ-UHFFFAOYSA-N 0.000 description 1
- GBMGXXPFNLJLMP-UHFFFAOYSA-N 3-ethoxybenzene-1,2-diamine Chemical compound CCOC1=CC=CC(N)=C1N GBMGXXPFNLJLMP-UHFFFAOYSA-N 0.000 description 1
- BFLWXPJTAKXXKT-UHFFFAOYSA-N 3-methoxybenzene-1,2-diamine Chemical compound COC1=CC=CC(N)=C1N BFLWXPJTAKXXKT-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 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
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 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
- 238000011049 filling Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 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
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
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)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2435818A DE2435818C3 (de) | 1974-07-25 | 1974-07-25 | Verfahren zur Herstellung aromatischer Diamine |
| US05/594,417 US4005143A (en) | 1974-07-25 | 1975-07-09 | Process for manufacturing aromatic diamines |
| JP50089275A JPS5827262B2 (ja) | 1974-07-25 | 1975-07-23 | ホウコウゾクジアミンノ セイゾウホウホウ |
| GB30988/75A GB1478795A (en) | 1974-07-25 | 1975-07-24 | Process for the manufacture of aromatic diamines |
| CH968475A CH611264A5 (OSRAM) | 1974-07-25 | 1975-07-24 | |
| FR7523371A FR2279718A1 (fr) | 1974-07-25 | 1975-07-25 | Procede de preparation de diamines aromatiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2435818A DE2435818C3 (de) | 1974-07-25 | 1974-07-25 | Verfahren zur Herstellung aromatischer Diamine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2435818A1 DE2435818A1 (de) | 1976-02-05 |
| DE2435818B2 DE2435818B2 (de) | 1977-09-29 |
| DE2435818C3 true DE2435818C3 (de) | 1982-02-25 |
Family
ID=5921506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2435818A Expired DE2435818C3 (de) | 1974-07-25 | 1974-07-25 | Verfahren zur Herstellung aromatischer Diamine |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4005143A (OSRAM) |
| JP (1) | JPS5827262B2 (OSRAM) |
| CH (1) | CH611264A5 (OSRAM) |
| DE (1) | DE2435818C3 (OSRAM) |
| FR (1) | FR2279718A1 (OSRAM) |
| GB (1) | GB1478795A (OSRAM) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2609835C3 (de) * | 1976-03-10 | 1979-06-07 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 3-Hydroxybuttersäure-N-arylamiden |
| GB1522273A (en) * | 1976-07-28 | 1978-08-23 | Ici Ltd | Catalytic reduction of dinitroalkoxybenzenes |
| FR2362116A1 (fr) * | 1976-08-20 | 1978-03-17 | Oreal | Metaphenylenediamines et compositions tinctoriales les contenant |
| SU685661A1 (ru) * | 1977-08-12 | 1979-09-15 | Институт Нефтехимического Синтеза Им. А.В.Топчиева | Способ получени анилина |
| JPS5488230A (en) * | 1977-12-21 | 1979-07-13 | Ihara Chem Ind Co Ltd | 4-alkoxy-3,5-diamino-alpha,alpha,alpha-trifluoromethylbenzene,its preparation, and hardeners for polyurethane elastomers consisting of it |
| US4283556A (en) * | 1978-09-11 | 1981-08-11 | Toms River Chemical Corporation | Process for the manufacture of substantially pure 3-amino-4-alkoxy-acylanilides from 2,4-dinitrochlorobenzene |
| US4404401A (en) * | 1979-02-23 | 1983-09-13 | Akzona Incorporated | Process for the preparation of para-amino-diphenylamine |
| US4400538A (en) * | 1981-06-11 | 1983-08-23 | Mobay Chemical Corporation | Fixed bed catalyst for MNB and DNT hydrogenation |
| US4760187A (en) * | 1981-08-14 | 1988-07-26 | E. I. Du Pont De Nemours And Company | Process for reducing chloronitrobenzenes using ruthenium with a minor amount of platinum as the catalyst |
| JPS60177160U (ja) * | 1984-05-04 | 1985-11-25 | 半田 憲治郎 | セクシヨンフランジボビンのフランジ |
| US4705898A (en) * | 1986-04-04 | 1987-11-10 | Texaco Inc. | Preparation of disecondary amines from diolefins and primary amines |
| US4766244A (en) * | 1986-10-30 | 1988-08-23 | The Dow Chemical Company | High purity process for the preparation of 4,6-diamino-1,3-benzenediol |
| USRE34745E (en) * | 1986-10-30 | 1994-09-27 | The Dow Chemical Company | High purity process for the preparation of 4,6-diamino-1,3-benzenediol |
| US5449832A (en) * | 1994-10-05 | 1995-09-12 | Air Products And Chemicals, Inc. | Process for storage and transport of toluenediamine |
| DE19911865A1 (de) * | 1999-03-17 | 2000-09-28 | Degussa | Verfahren zur katalytischen Hydrierung von Dinitrotoluol sowie Katalysator |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1793941A (en) * | 1925-05-08 | 1931-02-24 | Ig Farbenindustrie Ag | Iron-oxide pigment and process of producing the same as by-products of the reduction of aromatic nitro compounds |
| US2164154A (en) * | 1935-10-19 | 1939-06-27 | Du Pont | Hydrogenation of mono nitrated alkoxy benzenes |
| US2292879A (en) * | 1939-08-05 | 1942-08-11 | Solvay Process Co | Production of aromatic amines |
| DE1128858B (de) * | 1956-02-06 | 1962-05-03 | Gen Aniline & Film Corp | Verfahren zur katalytischen Reduktion aromatischer Polynitroverbindungen |
| US2894036A (en) * | 1956-02-06 | 1959-07-07 | Gen Aniline & Film Corp | Catalytic reduction of aromatic polynitro compounds |
| US3232989A (en) * | 1964-12-22 | 1966-02-01 | Gen Aniline & Film Corp | Aromatic dinitro compounds |
| DE2044657A1 (en) * | 1970-09-09 | 1972-03-23 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Toluylene diamine prepn - using solid ni or ru - contg catalyst |
-
1974
- 1974-07-25 DE DE2435818A patent/DE2435818C3/de not_active Expired
-
1975
- 1975-07-09 US US05/594,417 patent/US4005143A/en not_active Expired - Lifetime
- 1975-07-23 JP JP50089275A patent/JPS5827262B2/ja not_active Expired
- 1975-07-24 GB GB30988/75A patent/GB1478795A/en not_active Expired
- 1975-07-24 CH CH968475A patent/CH611264A5/xx not_active IP Right Cessation
- 1975-07-25 FR FR7523371A patent/FR2279718A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5827262B2 (ja) | 1983-06-08 |
| FR2279718A1 (fr) | 1976-02-20 |
| FR2279718B1 (OSRAM) | 1980-05-09 |
| DE2435818A1 (de) | 1976-02-05 |
| JPS5134119A (en) | 1976-03-23 |
| DE2435818B2 (de) | 1977-09-29 |
| CH611264A5 (OSRAM) | 1979-05-31 |
| GB1478795A (en) | 1977-07-06 |
| US4005143A (en) | 1977-01-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |