CS252945B1 - Method of 2,2,6,6-tetramethyl-4-piperidonoxime preparation - Google Patents
Method of 2,2,6,6-tetramethyl-4-piperidonoxime preparation Download PDFInfo
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- CS252945B1 CS252945B1 CS863686A CS368686A CS252945B1 CS 252945 B1 CS252945 B1 CS 252945B1 CS 863686 A CS863686 A CS 863686A CS 368686 A CS368686 A CS 368686A CS 252945 B1 CS252945 B1 CS 252945B1
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- Prior art keywords
- hydroxylamine
- tetramethyl
- piperidone
- reaction
- sulphate
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 9
- FFUVOHCLAIYVTL-UHFFFAOYSA-N n-(2,2,6,6-tetramethylpiperidin-4-ylidene)hydroxylamine Chemical compound CC1(C)CC(=NO)CC(C)(C)N1 FFUVOHCLAIYVTL-UHFFFAOYSA-N 0.000 title claims description 6
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 8
- 239000011541 reaction mixture Substances 0.000 claims abstract description 8
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims abstract description 6
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims abstract description 6
- 235000011130 ammonium sulphate Nutrition 0.000 claims abstract description 6
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 3
- NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000001166 ammonium sulphate Substances 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 claims 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims 1
- 230000001133 acceleration Effects 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 1
- 238000007086 side reaction Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- YAZGADZUKMSMOV-UHFFFAOYSA-N n-piperidin-4-ylidenehydroxylamine Chemical compound ON=C1CCNCC1 YAZGADZUKMSMOV-UHFFFAOYSA-N 0.000 abstract 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006146 oximation reaction Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- -1 tetramethylpiperidone oxime Chemical compound 0.000 description 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 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229940083618 sodium nitroprusside Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Abstract
Způsob přípravy 2,2,6,6-tetrametyl- -4-piperidonoximu vzorce I reakcí 2,2,6,6-tetrametyl~4-piperidonu a hydróxylaminu. Reakční směs o obsahu 2,2,6,6-tetrametyl-4-piperidonu a technického roztoku hydróxylaminu a amoniovýoh solí, přičemž molámí poměr 2,2,6,- 6-tetrametyl-4-piperidonu a hydroxyíaminu je 0,5 až 1 a technický roztok síranu hydróxylaminu a amoniových solí má složení I40 až 180 g síranu hydroxylaminu, 350 až 480 g síranu amonného, 3 až 15 g dusičnanu amonného a 20 až 60 g kysěliny sírové v jednom litru roztoku, se při teplotě 50 až 120 °C míchá do ukončené reakce a vytvořený produkt se izo« luje.Preparation of 2,2,6,6-tetramethyl- Of 4-piperidone oxime of formula I by reaction of 2,2,6,6-tetramethyl-4-piperidone and hydroxylamine. Content reaction mixture 2,2,6,6-tetramethyl-4-piperidone and technical a solution of the hydroxylamine and ammonium hydroxide salts, with a molar ratio of 2.2.6, - 6-tetramethyl-4-piperidone and hydroxyamine is 0.5 to 1 and the technical solution of sulfate the hydroxylamine and ammonium salts composition of I40 to 180 g of hydroxylamine sulfate, 350 to 480 g of ammonium sulfate, 3 to 15 g of ammonium nitrate and 20 to 60 g sulfuric acid in one liter of solution stirring at 50 to 120 ° C until complete reaction and product formed is iso it.
Description
(54)(54)
Způsob přípravy 2,2,6,6-tetrametyl-4-piperidonoximuA process for the preparation of 2,2,6,6-tetramethyl-4-piperidone oxime
Způsob přípravy 2,2,6,6-tetrametyl-4-piperidonoximu vzorce IA process for the preparation of 2,2,6,6-tetramethyl-4-piperidone oxime of formula I
reakcí 2,2,6,6-tetrametyl~4-piperidonu a hydróxylaminu. Reakční směs o obsahu 2,2,6,6-tetrametyl-4-piperidonu a technického roztoku hydróxylaminu a amoniovýoh solí, přičemž molámí poměr 2,2,6,6-tetrametyl-4-piperidonu a hydroxyíaminu je 0,5 až 1 a technický roztok síranu hydróxylaminu a amoniových solí má složení I40 až 180 g síranu hydroxylaminu, 350 až 480 g síranu amonného, 3 až 15 g dusičnanu amonného a 20 až 60 g kysěliny sírové v jednom litru roztoku, se při teplotě 50 až 120 °C míchá do ukončené reakce a vytvořený produkt se izo« luje.by reaction of 2,2,6,6-tetramethyl-4-piperidone and hydroxylamine. A reaction mixture containing 2,2,6,6-tetramethyl-4-piperidone and a technical solution of hydroxylamine and ammonium salts, the molar ratio of 2,2,6,6-tetramethyl-4-piperidone to hydroxylamine being 0.5 to 1 and technical solution of hydroxylamine sulphate and ammonium salts has the composition I40 to 180 g of hydroxylamine sulphate, 350 to 480 g of ammonium sulphate, 3 to 15 g of ammonium nitrate and 20 to 60 g of sulfuric acid in one liter of solution, stirred at 50 to 120 ° C until the reaction is complete and the product formed is isolated.
252 945252 945
252 945252 945
Vynález se týká technologie přípravy 2,z,Qt6-tetrametyl-4-piperidonoximu vzorce I oximací 2,2,6,6-tetrametyl-4-piperidonu technickým roztokem hydroxylaminsulfátu.The invention relates to the technology of preparation 2, Z, Q t 6-tetramethyl-4-piperidone of formula I oximation of 2,2,6,6-tetramethyl-4-piperidone, the technical solution of hydroxylamine.
HNHN
CH.CH.
\_ /-NOH-NOH
Uvedená sloučenina slouží jako základní meziprodukt při přípravě velkého množství organických sloučenin, které jsou založeny ba3 na jeho bázi, nebo na bázi 2,2, 6, 6-tetrametyl-4-amino piperidinu, který se z něho připravuje redukcí.Said compound serves as a basic intermediate in the preparation of a large number of organic compounds based on its base or on the basis of 2,2,6,6-tetramethyl-4-amino piperidine, which is prepared therefrom by reduction.
Způsoby přípravy této sloučeniny vycházejí z obecné přípra vy oximů, to znamená z reakce příslušného ketonu s volným hydroxylaminem,většinou za katalýzy přídavkem kyselin či zásad. Volný hydroxylamin se v těchto případech získává nejčastěji z hydrochloridu nebo síranu hydroxylaminu přídavkem ekvivalentního množství hydroxidu alkalického kovua popřípadě alkoholátu, v některých případech i přídavkem uhličitanu sodného či draselného . Často se uvolRf hydroxylaminu z jeho soli provádí přímo v reakění směsi za přítomnosti ketonu. Pro uvolnění báze byl užit i roztok octanu sodného. V laboratorním měřítku lze užít rovněž velmi energické oximační Činidlo, kterým je roztok hydroxylaminhydrochloridu v pyridinu. U katalyzovaných reakcí, kterými lze účinnou látku rovněž připravit, je používána především kyselá katalýza, kdy k reakci je užito například směsiMethods for preparing this compound are based on the general preparation of oximes, i.e., the reaction of the corresponding ketone with free hydroxylamine, mostly under catalysis by addition of acids or bases. In these cases, the free hydroxylamine is most often obtained from hydroxylamine hydrochloride or sulphate by the addition of an equivalent amount of alkali metal hydroxide and optionally alcoholate, in some cases by the addition of sodium or potassium carbonate. Often, the release of hydroxylamine from its salt is carried out directly in the reaction of the mixture in the presence of a ketone. Sodium acetate solution was also used to liberate the base. On a laboratory scale, a very energetic oximizing agent, which is a solution of hydroxylamine hydrochloride in pyridine, can also be used. In catalyzed reactions, which can also be used for the preparation of the active compound, acid catalysis is used, for example a mixture of
252 945 soli hydroxylaminu v alkoholu, ve vodě nebo v kyselině octové, někdy je přidáváno i další množství minerální kyseliny.252 945 hydroxylamine salts in alcohol, water or acetic acid, sometimes additional amounts of mineral acid are added.
Pro přípravu tetrametylpiperidonoximu je možno využít i způsobu oximace roztokem hydroxylamindisulfonanu sodného vznikajícího reakcí dusitanu sodného s kysličníkem siřičitým, který v kyselém prostředí může rovněž reagovat s ketonem za vzniku oximu.For the preparation of tetramethylpiperidone oxime, it is also possible to use a method of oximation with a solution of sodium hydroxylamine disulfonate formed by the reaction of sodium nitrite with sulfur dioxide, which in an acidic medium can also react with the ketone to form the oxime.
Vzhledem k dobré reaktivitě ketoskupiny u výchozíhoDue to the good reactivity of the keto group in the starting group
2,2,6,6-tetramety1-4-piperidonu je průběh všech těchto reakcí poměrně dobrý. Přestože by tedy při technologickém provedení reakce nemělo dojít k větším či závažnějším problémům, je nedostatkem těchto oximačních metod použití poměrně drahých chemikálií a v některých případech i nutnost dodatečného čištění produktu od zbytků rozpouštědel či katalyzátorů.2,2,6,6-tetramethyl-4-piperidone is relatively good. Thus, although no major or major problems should be encountered in carrying out the reaction, the lack of these oximation methods involves the use of relatively expensive chemicals and, in some cases, the need for additional purification of the product from solvent or catalyst residues.
IMyní bylo nalezeno, že novou technologií podle tohoto vynálezu lze 2, 2, 6, 6-tetrametyl-4-piperidonoxim připravit velmi snadno a levně, nebol použité oximační činidlo, způsob provedení reakce a izolace produktu, jsou oproti stávajícím způsobům velmi jednoduché při současně dosahovaném vysokém výtěžku a čistotě produktu.It has now been found that the novel technology of the present invention makes it possible to prepare 2, 2, 6, 6-tetramethyl-4-piperidone oxime very easily and inexpensively, since the oximating agent used, reaction method and product isolation are very simple high yield and purity of the product.
Způsob provedení nové technologie přípravy 2,2,6,6-tetrametyl-4-piperidonoximu je vyznačen tím, že reakčni směs obsahující 2,2,6,6-tetrametyl-4-piperidon a technický roztok síranu hydroxylaminu a amonných solí, přičemž molární poměr 2,2,6,6-tetrametyl-4-piperidonu a hydroxylaminu v této reakčni směsi je 0,5 až 1 a technický roztok síranu hydroxylaminu a amonných solí má složení 140 až 180 g síranu hydroxylaminu, 350 až 480 g síranu amonného, 3 až 15 g dusičnanu amonného a 20 až 60 g kyseliny sírové v jednom litru roztoku , se při teplotě 50 až 120 °C míchá do ukončení reakce a vytvořený produkt se izoluje.A process for carrying out a novel technology for the preparation of 2,2,6,6-tetramethyl-4-piperidone oxime is characterized in that the reaction mixture comprises 2,2,6,6-tetramethyl-4-piperidone and a technical solution of hydroxylamine sulphate and ammonium salts, wherein the molar molar the ratio of 2,2,6,6-tetramethyl-4-piperidone to hydroxylamine in this reaction mixture is 0.5 to 1 and the technical solution of hydroxylamine sulfate and ammonium salts has a composition of 140-180 g hydroxylamine sulfate, 350-480 g ammonium sulfate, 3 to 15 g of ammonium nitrate and 20 to 60 g of sulfuric acid in one liter of solution are stirred at 50 to 120 ° C until the reaction is complete and the product formed is isolated.
Konec reakce se zjišřuje externí zkouškou na přítomnost nezreagovaného ketonu některým ze specifických činidel na důkaž volné ketoskupiny, např. reakcí s nitroprusidem sodným nebo se lze o ukončení reakce orientačně přesvědčit čichem, neboř zmizí specifický, pach výchozí látky.The end of the reaction is determined by an external test for the presence of unreacted ketone by one of the specific reagents to detect the free keto group, for example by reaction with sodium nitroprusside, or the ending of the reaction can be reassured by smell, or
252 945 donu a hydroxylaminu je 0,55 /. Směs byla za míchání vyhřátá na 90 °c a na této teplotě ponechána reagovat 1 hodinu. Po této době je reakce skončena. Vzniklý produkt byl odsát a promyt stejně jako v příkladě 1. Výtěžek je prakticky stejný, kvalita produktu zůstává beze změny.252,945 don and hydroxylamine is 0.55 [mu]. The mixture was heated to 90 ° C with stirring and allowed to react at this temperature for 1 hour. After this time, the reaction is complete. The resulting product was aspirated and washed as in Example 1. The yield was practically the same, the product quality remained unchanged.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS863686A CS252945B1 (en) | 1986-05-21 | 1986-05-21 | Method of 2,2,6,6-tetramethyl-4-piperidonoxime preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS863686A CS252945B1 (en) | 1986-05-21 | 1986-05-21 | Method of 2,2,6,6-tetramethyl-4-piperidonoxime preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS368686A1 CS368686A1 (en) | 1987-02-12 |
| CS252945B1 true CS252945B1 (en) | 1987-10-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS863686A CS252945B1 (en) | 1986-05-21 | 1986-05-21 | Method of 2,2,6,6-tetramethyl-4-piperidonoxime preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS252945B1 (en) |
-
1986
- 1986-05-21 CS CS863686A patent/CS252945B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS368686A1 (en) | 1987-02-12 |
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