SK27696A3 - Method of methylation of 2,2,6,6-tetramethylpiperidin-4-one - Google Patents
Method of methylation of 2,2,6,6-tetramethylpiperidin-4-one Download PDFInfo
- Publication number
- SK27696A3 SK27696A3 SK276-96A SK27696A SK27696A3 SK 27696 A3 SK27696 A3 SK 27696A3 SK 27696 A SK27696 A SK 27696A SK 27696 A3 SK27696 A3 SK 27696A3
- Authority
- SK
- Slovakia
- Prior art keywords
- tetramethylpiperidin
- formic acid
- formaldehyde
- methylation
- mol
- Prior art date
Links
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000011987 methylation Effects 0.000 title claims description 9
- 238000007069 methylation reaction Methods 0.000 title claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 48
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 41
- 235000019253 formic acid Nutrition 0.000 claims abstract description 21
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 20
- DLGQWDCMIMRYHA-UHFFFAOYSA-N 1-(hydroxymethyl)-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1CO DLGQWDCMIMRYHA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- GHJUORCGZFHNKG-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-one Chemical compound CN1C(C)(C)CC(=O)CC1(C)C GHJUORCGZFHNKG-UHFFFAOYSA-N 0.000 abstract description 7
- 230000001035 methylating effect Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 7
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- -1 2,2,6,6-tetramethylpiperidin-4-yl groups Chemical group 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003918 triazines Chemical class 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT95MI000389A IT1277329B1 (it) | 1995-03-01 | 1995-03-01 | Procedimento per la metilazione del 2,2,6,6-tetrametil-4-piperidone (triacetonammina) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK27696A3 true SK27696A3 (en) | 1996-10-02 |
Family
ID=11370735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK276-96A SK27696A3 (en) | 1995-03-01 | 1996-02-28 | Method of methylation of 2,2,6,6-tetramethylpiperidin-4-one |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0729947A1 (ja) |
| JP (1) | JPH08245588A (ja) |
| KR (1) | KR960034173A (ja) |
| BR (1) | BR9600847A (ja) |
| CA (1) | CA2170588A1 (ja) |
| IT (1) | IT1277329B1 (ja) |
| SK (1) | SK27696A3 (ja) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2789609A1 (en) | 2013-04-11 | 2014-10-15 | Bruker Biospin (SAS) | Highly efficient polarizing agents for dynamic nuclear polarization |
| MX2016000700A (es) | 2015-01-22 | 2017-04-06 | Evonik Degussa Gmbh | Sintesis de compuestos de triacetonadiamina mediante procedimiento de aminacion reductora de triacetonadiamina y derivados de los mismos. |
| MX2016000701A (es) * | 2015-01-22 | 2016-11-24 | Evonik Degussa Gmbh | Proceso para preparar un compuesto de triacetonamina n-metil sustituida. |
| DE102016212378A1 (de) | 2016-07-07 | 2018-01-11 | Evonik Degussa Gmbh | Synthese von Triacetondiaminverbindungen durch reduktive Aminierung ausgehend von Triacetondiamin und dessen Derivaten |
| DE102016212379A1 (de) * | 2016-07-07 | 2018-01-11 | Evonik Degussa Gmbh | Verfahren zur Herstellung einer N-methylsubstituierten Triacetonaminverbindung |
| MX2022007419A (es) | 2019-12-16 | 2022-07-13 | Basf Se | Proceso para la preparacion de compuestos de piperidina. |
| CN110950794A (zh) * | 2019-12-26 | 2020-04-03 | 宿迁联盛科技股份有限公司 | 一种1,2,2,6,6-五甲基-4-哌啶酮的制备方法 |
| CN111116457A (zh) * | 2019-12-26 | 2020-05-08 | 宿迁联盛科技股份有限公司 | 一种1,2,2,6,6-五甲基-4-哌啶酮的绿色合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1223405B (it) * | 1987-12-04 | 1990-09-19 | Ciba Geigy Spa | Procedimento per la metilazione di composti triazinici contenenti gruppi 2,2,6,6 tetrametilpiperidinici |
-
1995
- 1995-03-01 IT IT95MI000389A patent/IT1277329B1/it active IP Right Grant
-
1996
- 1996-02-19 EP EP96810099A patent/EP0729947A1/en not_active Withdrawn
- 1996-02-28 CA CA002170588A patent/CA2170588A1/en not_active Abandoned
- 1996-02-28 SK SK276-96A patent/SK27696A3/sk unknown
- 1996-02-29 BR BR9600847A patent/BR9600847A/pt not_active Application Discontinuation
- 1996-02-29 KR KR1019960005636A patent/KR960034173A/ko not_active Application Discontinuation
- 1996-02-29 JP JP8069184A patent/JPH08245588A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0729947A1 (en) | 1996-09-04 |
| BR9600847A (pt) | 1997-12-30 |
| ITMI950389A0 (it) | 1995-03-01 |
| CA2170588A1 (en) | 1996-09-02 |
| ITMI950389A1 (it) | 1996-09-01 |
| KR960034173A (ko) | 1996-10-22 |
| JPH08245588A (ja) | 1996-09-24 |
| IT1277329B1 (it) | 1997-11-10 |
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