CH574412A5 - 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 - Google Patents

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

Info

Publication number: CH574412A5
Authority: CH; Switzerland
Prior art keywords: acetone; acid; hours; boron trifluoride; process step
Prior art date: 1973-06-25

Application number

CH924173A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1973-06-25

Filing date

1973-06-25

Publication date

1976-04-15

1973-06-25 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1973-06-25 Priority to CH924173A priority Critical patent/CH574412A5/de

1974-06-20 Priority to FI1905/74A priority patent/FI190574A7/fi

1974-06-20 Priority to NO742255A priority patent/NO742255L/no

1974-06-20 Priority to SE7408172A priority patent/SE403478B/xx

1974-06-20 Priority to DK330874AA priority patent/DK139678B/da

1974-06-21 Priority to ES427508A priority patent/ES427508A1/es

1974-06-21 Priority to HUCI001483 priority patent/HU176761B/hu

1974-06-21 Priority to BG027040A priority patent/BG27080A3/xx

1974-06-21 Priority to AT517774A priority patent/AT338262B/de

1974-06-21 Priority to IE1302/74A priority patent/IE39523B1/xx

1974-06-21 Priority to IL45095A priority patent/IL45095A/en

1974-06-21 Priority to BR510674A priority patent/BR7405106A/pt

1974-06-21 Priority to CA203,059A priority patent/CA1027950A/fr

1974-06-21 Priority to AR254314A priority patent/AR202653A1/es

1974-06-21 Priority to NL7408409A priority patent/NL190846C/xx

1974-06-21 Priority to LU70387*A priority patent/LU70387A1/xx

1974-06-21 Priority to BE145745A priority patent/BE816703A/fr

1974-06-21 Priority to DE2429937A priority patent/DE2429937A1/de

1974-06-21 Priority to DD179373A priority patent/DD112443A5/xx

1974-06-21 Priority to ZA00744005A priority patent/ZA744005B/xx

1974-06-21 Priority to JP49071215A priority patent/JPS5929589B2/ja

1974-06-21 Priority to GB2760474A priority patent/GB1461703A/en

1974-06-21 Priority to US05/481,922 priority patent/US3959295A/en

1974-06-21 Priority to FR7421684A priority patent/FR2234291B1/fr

1974-06-21 Priority to IT24300/74A priority patent/IT1021057B/it

1974-06-24 Priority to AU70432/74A priority patent/AU479247B2/en

1974-06-24 Priority to EG24174A priority patent/EG11118A/xx

1974-06-24 Priority to TR17835A priority patent/TR17835A/xx

1976-04-15 Publication of CH574412A5 publication Critical patent/CH574412A5/de

Links

CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 106
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title claims abstract description 30
229910021529 ammonia Inorganic materials 0.000 title claims description 12
JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 title claims description 10
239000003377 acid catalyst Substances 0.000 title abstract 2
239000003054 catalyst Substances 0.000 claims abstract description 25
239000002253 acid Substances 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 8
238000000034 method Methods 0.000 claims description 53
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 46
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
229910015900 BF3 Inorganic materials 0.000 claims description 23
235000019270 ammonium chloride Nutrition 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
150000003863 ammonium salts Chemical class 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000000047 product Substances 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 5
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
239000001110 calcium chloride Substances 0.000 claims description 4
229910001628 calcium chloride Inorganic materials 0.000 claims description 4
238000002425 crystallisation Methods 0.000 claims description 4
230000008025 crystallization Effects 0.000 claims description 4
150000003891 oxalate salts Chemical class 0.000 claims description 4
235000006408 oxalic acid Nutrition 0.000 claims description 4
238000003756 stirring Methods 0.000 claims description 4
239000011592 zinc chloride Substances 0.000 claims description 4
235000005074 zinc chloride Nutrition 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
PIFBMJMXJMZZRG-UHFFFAOYSA-N 2,2,4,6,6-pentamethyl-1,5-dihydropyrimidine Chemical compound CC1=NC(C)(C)NC(C)(C)C1 PIFBMJMXJMZZRG-UHFFFAOYSA-N 0.000 claims description 2
239000005695 Ammonium acetate Substances 0.000 claims description 2
239000002841 Lewis acid Substances 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
229940043376 ammonium acetate Drugs 0.000 claims description 2
235000019257 ammonium acetate Nutrition 0.000 claims description 2
-1 ammonium salts ammonium acetate Chemical class 0.000 claims description 2
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
229910052921 ammonium sulfate Inorganic materials 0.000 claims description 2
235000011130 ammonium sulphate Nutrition 0.000 claims description 2
239000012230 colorless oil Substances 0.000 claims description 2
239000013078 crystal Substances 0.000 claims description 2
238000000354 decomposition reaction Methods 0.000 claims description 2
238000004821 distillation Methods 0.000 claims description 2
238000001704 evaporation Methods 0.000 claims description 2
230000008020 evaporation Effects 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
150000007517 lewis acids Chemical class 0.000 claims description 2
230000008018 melting Effects 0.000 claims description 2
238000002844 melting Methods 0.000 claims description 2
229910001510 metal chloride Inorganic materials 0.000 claims description 2
238000006386 neutralization reaction Methods 0.000 claims description 2
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims description 2
238000001556 precipitation Methods 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract 4
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
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
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
150000001447 alkali salts Chemical class 0.000 abstract 1
150000001732 carboxylic acid derivatives Chemical class 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
238000010438 heat treatment Methods 0.000 abstract 1
229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
239000011707 mineral Substances 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
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
- C07D211/02—Preparation by ring-closure or hydrogenation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)

CH924173A 1973-05-17 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 CH574412A5 (en)

Priority Applications (28)

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
FI1905/74A FI190574A7 (fr)	1973-06-25	1974-06-20
NO742255A NO742255L (fr)	1973-06-25	1974-06-20
SE7408172A SE403478B (sv)	1973-06-25	1974-06-20	Sett att framstella 2,2,6,6-tetrametyl-4-oxopiperidin
DK330874AA DK139678B (da)	1973-06-25	1974-06-20	Fremgangsmåde til fremstilling af 2,2,6,6-tetramethyl-4-oxopiperidin.
ES427508A ES427508A1 (es)	1973-06-25	1974-06-21	Procedimiento para la preparacion de 2,2,6,6-tetrametil-4- oxopiperidina.
HUCI001483 HU176761B (en)	1973-06-25	1974-06-21	Process for producing 2,2,6,6-tetramethyl-4-oxopiperidine bracket triacetonamine bracket closed
BG027040A BG27080A3 (bg)	1973-06-25	1974-06-21	Метод за получаване на 2,2,6,6-тетраметил-4- оксипиперидин
AT517774A AT338262B (de)	1973-06-25	1974-06-21	Verfahren zur herstellung von 2,2,6,6-tetramethyl-4-oxopiperidin
IE1302/74A IE39523B1 (en)	1973-06-25	1974-06-21	Process for the preparation of 2,2,6,6,-tetramethyl-4-oxopiperidine
IL45095A IL45095A (en)	1973-06-25	1974-06-21	Preparation of 2,2,6,6-tetramethyl-4-oxopiperidine
BR510674A BR7405106A (pt)	1973-06-25	1974-06-21	Processo para fabricacao de 2,2,6,6,-tetrametil-4-oxopiperidina
CA203,059A CA1027950A (fr)	1973-06-25	1974-06-21	Synthese de la 2,2,6,6-tetramethyle-4-oxopiperidine
AR254314A AR202653A1 (es)	1973-06-25	1974-06-21	Preparacion de 2,2,6,6-tetrametil-4-oxopiperidina
NL7408409A NL190846C (nl)	1973-06-25	1974-06-21	Werkwijze voor het bereiden van 2,2,6,6-tetramethyl-4-piperidon.
LU70387*A LU70387A1 (fr)	1973-06-25	1974-06-21
BE145745A BE816703A (fr)	1973-06-25	1974-06-21	Procede de preparation d'une tetramethyl-oxo-piperidine
DE2429937A DE2429937A1 (de)	1973-06-25	1974-06-21	Verfahren zur herstellung von 2,2,6,6tetramethyl-4-oxo-piperidin
DD179373A DD112443A5 (de)	1973-06-25	1974-06-21	Verfahren zur herstellung von 2,2,6,6-tetramethyl-4-oxopiperidin
ZA00744005A ZA744005B (en)	1973-06-25	1974-06-21	Process for the preparation o 2,2,6,6-tetramethyl- 4-oxopiperdine
JP49071215A JPS5929589B2 (ja)	1973-06-25	1974-06-21	２，２，６，６−テトラメチル−４−オキソピペリジンの製造方法
GB2760474A GB1461703A (en)	1973-06-25	1974-06-21	Process for the preparation of 2,2,6,6-tetramethyl-4-oxopiper idine
US05/481,922 US3959295A (en)	1973-05-17	1974-06-21	Process for the preparation of 2,2,6,6-tetramethyl-4-oxopiperidine
FR7421684A FR2234291B1 (fr)	1973-06-25	1974-06-21
IT24300/74A IT1021057B (it)	1973-06-25	1974-06-21	Procedimento per la preparazione di 2.2.6.6 tetrametil 4 osso piperidina
AU70432/74A AU479247B2 (en)	1973-06-25	1974-06-24	Process for the preparation of 2, 2, 6, 6-tetramethyl-4-oxopiperidine
EG24174A EG11118A (en)	1973-06-25	1974-06-24	Process for the preparation of 2,2,6,6-tetramethyl-4-oxopiperidine
TR17835A TR17835A (tr)	1973-06-25	1974-06-24	2,2,6,6-tetrametil-4-oksopiperidin imaline mahsus usul

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
CH574412A5 true CH574412A5 (en)	1976-04-15

Family

ID=4349871

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH924173A CH574412A5 (en)	1973-05-17	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

Country Status (4)

Country	Link
BE (1)	BE816703A (fr)
CH (1)	CH574412A5 (fr)
TR (1)	TR17835A (fr)
ZA (1)	ZA744005B (fr)

1973
- 1973-06-25 CH CH924173A patent/CH574412A5/de not_active IP Right Cessation
1974
- 1974-06-21 BE BE145745A patent/BE816703A/fr not_active IP Right Cessation
- 1974-06-21 ZA ZA00744005A patent/ZA744005B/xx unknown
- 1974-06-24 TR TR17835A patent/TR17835A/xx unknown

Also Published As

Publication number	Publication date
BE816703A (fr)	1974-12-23
TR17835A (tr)	1976-04-13
ZA744005B (en)	1975-06-25

Legal Events

Date	Code	Title	Description
1986-02-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE1795808C2 (de)	1980-06-26	Verfahren zur Herstellung von 2,2,6,6-Tetramethyl-4-oxopiperidin
EP0088275B1 (fr)	1986-01-22	Procédé de synthèse du triméthylolpropane
DE1244151B (de)	1967-07-13	Verfahren zur Herstellung von gesaettigten alpha-Di- oder Trimethylolfettsaeuren
DE1200281B (de)	1965-09-09	Verfahren zur Herstellung von Acetessigsaeureestern
DD239591A5 (de)	1986-10-01	Verfahren zur herstellung von 2,4-dichlor-5-fluor-benzoesaeure
CH574412A5 (en)	1976-04-15	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
CH618413A5 (fr)	1980-07-31
EP0355350B1 (fr)	1992-11-25	Procédé de préparation de 4,4-diméthyl-1-(p-chlorophényl)-pentane-3-one
DE2614827C2 (de)	1983-01-20	Verfahren zur Herstellung von 3-Phenylpyridazon-(6)
DE1918253A1 (de)	1970-10-08	Verbessertes Verfahren zur Herstellung von 3-Hydroxyisoxazolverbindungen
DE2636278A1 (de)	1978-02-16	Verfahren zur herstellung von dialkylketalen
EP0050869B1 (fr)	1984-06-20	Procédé pour la préparation de N-tert.-alcoylamines ou cycloalcoylamines et d'esters de l'acide formique
DE2819798C2 (fr)	1989-02-16
DE1793144A1 (de)	1972-02-03	Phenylsalicylsaeure-Verbindungen und Verfahren zu deren Herstellung
DE3815084C1 (fr)	1989-03-02
DE1793350C3 (de)	1978-02-16	Verfahren zur Herstellung von alkylsubstituierten Glutarsäuren
DE1593175A1 (de)	1970-07-30	Verfahren zur Herstellung von Dicarbonsaeuren
DE1958619C3 (de)	1979-03-15	Verfahren zur Herstellung substituierter Pyrazine
DE3402997A1 (de)	1985-08-01	Verfahren zur herstellung von 3-n-dialkylaminophenolen
DE2513952C2 (de)	1977-02-17	Verfahren zur herstellung von monochlorbenzoesaeuren
DE2619574C3 (de)	1979-08-23	Verfahren zur Herstellung von 3-Brompropionsäureamid
DE1620512A1 (de)	1970-09-03	Verfahren zur Herstellung von 2-methyl-3-hydroxy-4,5-disubstituierten Pyridinen
DE1795239A1 (de)	1971-12-30	Verfahren zur Herstellung von Dialkylpyridinen gegebenenfalls neben Aminpropanolen
DE2925041A1 (de)	1980-01-10	Verfahren zur synthese einer phenylessigsaeure
DE1238460B (de)	1967-04-13	Verfahren zur Herstellung von Azinen