IE39523L - Preparation of 2,2,6,6-tetramethyl-4-oxopiperidine - Google Patents
Preparation of 2,2,6,6-tetramethyl-4-oxopiperidineInfo
- Publication number
- IE39523L IE39523L IE741302A IE130274A IE39523L IE 39523 L IE39523 L IE 39523L IE 741302 A IE741302 A IE 741302A IE 130274 A IE130274 A IE 130274A IE 39523 L IE39523 L IE 39523L
- Authority
- IE
- Ireland
- Prior art keywords
- acetone
- acid
- ammonia
- triacetoneamine
- april
- Prior art date
Links
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 title abstract 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 abstract 2
- -1 AlCl 3 Chemical class 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000003377 acid catalyst Substances 0.000 abstract 2
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000003426 co-catalyst Substances 0.000 abstract 1
- CQTRUFMMCCOKTA-UHFFFAOYSA-N diacetoneamine hydrogen oxalate Natural products CC(=O)CC(C)(C)N CQTRUFMMCCOKTA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 abstract 1
- 229930193351 phorone Natural products 0.000 abstract 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
1461703 Triacetoneamine CIBA-GEIGY AG 21 June 1974 [25 June 1973 5 Oct 1973 19 April 1974 24 April 1974 22 May 1974] 27604/74 Heading C2C 2,2,6,6 - Tetramethyl - 4 - oxopiperidine (triacetoneamine) is prepared by (a) reacting acetone with ammonia at 5-60‹ C. in the presence of 0À2-1À2 mol. per cent, relative to the acetone, of an acid catalyst and (b) completing the reaction by further heating with or without the addition of further acetone and/or diacetone alcohol, mesityl oxide, phorone, diacetoneamine or triacetonediamine; these acetone derivatives may also be present in stage (a), and some of the acetone in stage (a) may be replaced by diacetone alcohol and/or mesityl oxide; the total acetone (or acetone + acetone derivative) employed is at least 1À6 moles per mole ammonia. The acid catalyst may be a Lewis acid (e.g. AlCl 3 , SnCl 4 , BF 3 ), a proton acid (e.g. a mineral, sulphonic, phosphonic, phosphinic or carboxylic acid) or a salt of a proton acid with ammonia or a nitrogencontaining organic base. Other salts, bromine and iodine, are listed as possible co-catalysts. Solvents may be used, e.g. hydrocarbons, ethers, nitriles, aprotic polar solvents and alcohols, especially C 1 -C 4 alcohols. The product may be isolated as such, or as its hydrate or salt with, for example, sulphuric, hydrochloric or oxalic acid.
[GB1461703A]
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH924173A CH574412A5 (en) | 1973-06-25 | 1973-06-25 | 2,2,6,6-Tetra-methyl-4-oxo-piperidine prepn. - from acetone and ammonia with acid catalyst in two stages with addn. of further acetone in second stage |
| CH1425773 | 1973-10-05 | ||
| CH543974 | 1974-04-19 | ||
| CH559974 | 1974-04-24 | ||
| CH701874A CH582147A5 (en) | 1974-05-22 | 1974-05-22 | 2,2,6,6-Tetra-methyl-4-oxo-piperidine prepn. - from acetone and ammonia with acid catalyst in two stages with addn. of further acetone in second stage |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE39523L true IE39523L (en) | 1974-12-25 |
| IE39523B1 IE39523B1 (en) | 1978-10-25 |
Family
ID=27509238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1302/74A IE39523B1 (en) | 1973-06-25 | 1974-06-21 | Process for the preparation of 2,2,6,6,-tetramethyl-4-oxopiperidine |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5929589B2 (en) |
| AR (1) | AR202653A1 (en) |
| AT (1) | AT338262B (en) |
| BG (1) | BG27080A3 (en) |
| CA (1) | CA1027950A (en) |
| DD (1) | DD112443A5 (en) |
| DE (1) | DE2429937A1 (en) |
| DK (1) | DK139678B (en) |
| FI (1) | FI190574A7 (en) |
| FR (1) | FR2234291B1 (en) |
| GB (1) | GB1461703A (en) |
| HU (1) | HU176761B (en) |
| IE (1) | IE39523B1 (en) |
| IL (1) | IL45095A (en) |
| IT (1) | IT1021057B (en) |
| LU (1) | LU70387A1 (en) |
| NL (1) | NL190846C (en) |
| NO (1) | NO742255L (en) |
| SE (1) | SE403478B (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2807172A1 (en) * | 1978-02-20 | 1979-08-23 | Huels Chemische Werke Ag | METHOD FOR PREPARING 2,2,6,6-TETRAMETHYLPIPERIDONE- (4) |
| IT1094039B (en) * | 1978-03-31 | 1985-07-26 | Chimosa Chimica Organica Spa | PROCESS FOR THE PREPARATION OF 2,2,6,6-TETRAMETHY-4-PIPERIDONE |
| US4275211A (en) * | 1978-11-17 | 1981-06-23 | Ciba-Geigy Corporation | Process for preparing 2,2,6,6-tetraalkyl-4-oxopiperidines |
| DE2916471A1 (en) * | 1979-04-24 | 1980-11-06 | Hoechst Ag | Tri:acetonamine prodn. from acetone and ammonia - under defined conditions using little or no catalyst |
| DE3013403A1 (en) * | 1980-04-05 | 1981-10-08 | Hoechst Ag, 6000 Frankfurt | METHOD FOR PRODUCING 2,2,6,6-TETRAMETHYLPIPERDON-4 |
| DE3119514A1 (en) * | 1981-05-15 | 1983-02-24 | Empresa Cubana Exportadora e Importadora de Productos Médicos Medicuba, La Habana | Triacetoneamine hydrochloride, process for its preparation and medicaments |
| JPH0739389B2 (en) * | 1986-03-03 | 1995-05-01 | 吉富製薬株式会社 | Method for producing 2,2,6,6-tetramethyl-4-oxopiperidine |
| DE19634157A1 (en) * | 1996-08-23 | 1998-02-26 | Basf Ag | Process for the preparation of 2,2,6,6-tetramethylpiperidin-4-one |
| DE102012215903A1 (en) | 2012-09-07 | 2014-03-13 | Evonik Industries Ag | Process for the treatment of a wastewater stream, which results from the workup of a triacetonamine-containing reaction mixture |
| DE102012215900A1 (en) | 2012-09-07 | 2014-05-15 | Evonik Industries Ag | Process for the preparation and processing of a triacetonamine-containing reaction mixture |
| EP3663284B1 (en) | 2018-12-07 | 2021-02-03 | Evonik Operations GmbH | Improved method for the preparation of triacetonamine |
| EP3750876A1 (en) | 2019-06-13 | 2020-12-16 | Evonik Operations GmbH | Method for preparing triacetone amine, 2,2,4,6-tetramethylpiperidine and/or the salts of 2,2,4,6-tetramethylpiperidine |
| US11731940B2 (en) | 2020-05-07 | 2023-08-22 | Evonik Operations Gmbh | Process for preparing triacetonamine |
| EP4279484A1 (en) | 2022-05-17 | 2023-11-22 | Sabo GmbH | Improved method for the preparation of triacetonamine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3513170A (en) * | 1966-07-23 | 1970-05-19 | Sankyo Co | Preparation of 2,2,6,6-tetramethyl-4-oxopiperidine |
-
1974
- 1974-06-20 FI FI1905/74A patent/FI190574A7/fi unknown
- 1974-06-20 DK DK330874AA patent/DK139678B/en unknown
- 1974-06-20 SE SE7408172A patent/SE403478B/en unknown
- 1974-06-20 NO NO742255A patent/NO742255L/no unknown
- 1974-06-21 GB GB2760474A patent/GB1461703A/en not_active Expired
- 1974-06-21 IE IE1302/74A patent/IE39523B1/en unknown
- 1974-06-21 BG BG027040A patent/BG27080A3/en unknown
- 1974-06-21 IT IT24300/74A patent/IT1021057B/en active
- 1974-06-21 AT AT517774A patent/AT338262B/en not_active IP Right Cessation
- 1974-06-21 HU HUCI001483 patent/HU176761B/en unknown
- 1974-06-21 JP JP49071215A patent/JPS5929589B2/en not_active Expired
- 1974-06-21 IL IL45095A patent/IL45095A/en unknown
- 1974-06-21 FR FR7421684A patent/FR2234291B1/fr not_active Expired
- 1974-06-21 LU LU70387*A patent/LU70387A1/xx unknown
- 1974-06-21 NL NL7408409A patent/NL190846C/en not_active IP Right Cessation
- 1974-06-21 DE DE2429937A patent/DE2429937A1/en active Granted
- 1974-06-21 AR AR254314A patent/AR202653A1/en active
- 1974-06-21 CA CA203,059A patent/CA1027950A/en not_active Expired
- 1974-06-21 DD DD179373A patent/DD112443A5/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR202653A1 (en) | 1975-06-30 |
| IT1021057B (en) | 1978-01-30 |
| NO742255L (en) | 1975-01-20 |
| NL190846B (en) | 1994-04-18 |
| IL45095A0 (en) | 1974-09-10 |
| DD112443A5 (en) | 1975-04-12 |
| NL190846C (en) | 1994-09-16 |
| SE403478B (en) | 1978-08-21 |
| BG27080A3 (en) | 1979-08-15 |
| NL7408409A (en) | 1974-12-30 |
| HU176761B (en) | 1981-05-28 |
| CA1027950A (en) | 1978-03-14 |
| JPS5929589B2 (en) | 1984-07-21 |
| DE2429937C2 (en) | 1988-01-28 |
| DK139678B (en) | 1979-03-26 |
| AT338262B (en) | 1977-08-10 |
| IL45095A (en) | 1977-05-31 |
| FR2234291A1 (en) | 1975-01-17 |
| FI190574A7 (en) | 1974-12-26 |
| LU70387A1 (en) | 1976-04-13 |
| JPS5036473A (en) | 1975-04-05 |
| IE39523B1 (en) | 1978-10-25 |
| DE2429937A1 (en) | 1975-01-16 |
| DK139678C (en) | 1979-09-10 |
| FR2234291B1 (en) | 1980-01-25 |
| GB1461703A (en) | 1977-01-19 |
| AU7043274A (en) | 1976-01-08 |
| ATA517774A (en) | 1976-12-15 |
| SE7408172L (en) | 1974-12-27 |
| DK330874A (en) | 1975-02-17 |
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