DE3525387A1 - Verfahren zur herstellung von 4-amino-2,2,6,6- tetramethylpiperidin - Google Patents
Verfahren zur herstellung von 4-amino-2,2,6,6- tetramethylpiperidinInfo
- Publication number
- DE3525387A1 DE3525387A1 DE19853525387 DE3525387A DE3525387A1 DE 3525387 A1 DE3525387 A1 DE 3525387A1 DE 19853525387 DE19853525387 DE 19853525387 DE 3525387 A DE3525387 A DE 3525387A DE 3525387 A1 DE3525387 A1 DE 3525387A1
- Authority
- DE
- Germany
- Prior art keywords
- tetramethyl
- oxopiperidine
- amino
- pressure
- autoclave
- 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.)
- Granted
Links
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 3
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 claims description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 11
- 239000012467 final product Substances 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005576 amination reaction Methods 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical class [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 150000004679 hydroxides Chemical class 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU852550A HU199367B (en) | 1985-06-28 | 1985-06-28 | Process for production of 4-amin-2,2,6,6-tetramethilpiperidin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08514952A GB2176473B (en) | 1985-06-13 | 1985-06-13 | Preparation of 4-amino-2,2,6, 6-tetramethylpiperidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3525387A1 true DE3525387A1 (de) | 1987-01-22 |
| DE3525387C2 DE3525387C2 (enExample) | 1988-12-08 |
Family
ID=10580675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853525387 Granted DE3525387A1 (de) | 1985-06-13 | 1985-07-16 | Verfahren zur herstellung von 4-amino-2,2,6,6- tetramethylpiperidin |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS61293969A (enExample) |
| CH (1) | CH664361A5 (enExample) |
| DE (1) | DE3525387A1 (enExample) |
| GB (1) | GB2176473B (enExample) |
| NL (1) | NL8501735A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0838456A1 (de) * | 1996-10-28 | 1998-04-29 | Basf Aktiengesellschaft | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin (TAD) über das Zwischenprodukt 2,2,6,6-Tetramethyl-4-[(2,2,6,6-tetramethyl-4-piperidyliden)amino]-piperidin |
| EP0863137A1 (de) * | 1997-03-06 | 1998-09-09 | Basf Aktiengesellschaft | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethyl-piperidin |
| DE19743433C1 (de) * | 1997-10-01 | 1999-04-22 | Basf Ag | Verfahren zur Reinigung von 4-Amino-piperidinen |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1270975B (it) * | 1993-06-03 | 1997-05-26 | Ciba Geigy Spa | Composti piperidin-triazinici atti all'impiego come stabilizzanti allaluce, al calore e alla ossidazione per materiali organici |
| DE4442990A1 (de) | 1994-12-02 | 1996-06-05 | Huels Chemische Werke Ag | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
| DE19544599A1 (de) * | 1995-11-30 | 1997-06-05 | Huels Chemische Werke Ag | Kontinuierliches Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
| DE102008040045A1 (de) | 2008-02-01 | 2009-08-06 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
| EP2085384A1 (de) | 2008-02-01 | 2009-08-05 | Evonik Degussa GmbH | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
| CN108484483A (zh) * | 2018-05-01 | 2018-09-04 | 衡水凯亚化工有限公司 | 一种利用蒸馏-结晶组合法精制三丙酮胺的方法 |
| CN109836370A (zh) * | 2019-03-20 | 2019-06-04 | 萧县新秀新材料有限公司 | 特定pH范围的2,2,6,6-四甲基哌啶胺的合成法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3003843A1 (de) * | 1980-02-02 | 1981-08-13 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von 4-amino-2,2,6,6-tetramethylpiperidin |
-
1985
- 1985-06-12 CH CH249485A patent/CH664361A5/de not_active IP Right Cessation
- 1985-06-13 GB GB08514952A patent/GB2176473B/en not_active Expired
- 1985-06-15 NL NL8501735A patent/NL8501735A/nl not_active Application Discontinuation
- 1985-06-21 JP JP13441485A patent/JPS61293969A/ja active Granted
- 1985-07-16 DE DE19853525387 patent/DE3525387A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3003843A1 (de) * | 1980-02-02 | 1981-08-13 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von 4-amino-2,2,6,6-tetramethylpiperidin |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0838456A1 (de) * | 1996-10-28 | 1998-04-29 | Basf Aktiengesellschaft | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin (TAD) über das Zwischenprodukt 2,2,6,6-Tetramethyl-4-[(2,2,6,6-tetramethyl-4-piperidyliden)amino]-piperidin |
| US5859250A (en) * | 1996-10-28 | 1999-01-12 | Basf Aktiengesellschaft | Preparation of 4-amino-2,2,6,6-tetramethylpiperidine (TAD) via 2,2,6,6-tetramethyl-4- (2,2,6,6-tetramethyl-4-piperidylidene) amino!piperidine as intermediate |
| EP0863137A1 (de) * | 1997-03-06 | 1998-09-09 | Basf Aktiengesellschaft | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethyl-piperidin |
| DE19743433C1 (de) * | 1997-10-01 | 1999-04-22 | Basf Ag | Verfahren zur Reinigung von 4-Amino-piperidinen |
Also Published As
| Publication number | Publication date |
|---|---|
| CH664361A5 (de) | 1988-02-29 |
| DE3525387C2 (enExample) | 1988-12-08 |
| JPS61293969A (ja) | 1986-12-24 |
| GB2176473A (en) | 1986-12-31 |
| GB8514952D0 (en) | 1985-07-17 |
| NL8501735A (nl) | 1987-01-02 |
| GB2176473B (en) | 1988-12-29 |
| JPH0445508B2 (enExample) | 1992-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8330 | Complete disclaimer |