826-36-8

Basic information

• Product Name: Triacetonamine
• Synonyms: LABOTEST-BB LT00159409;2,2,6,6-TETRAMETHYLTETRAHYDRO-4(1H)-PYRIDINONE;2,2,6,6-TETRAMETHYL-PIPERIDIN-4-ONE;2,2,6,6-TETRAMETHYL-4-PIPERIDINONE;2,2,6,6-TETRAMETHYL-4-PIPERIDONE;TETRAMETHYLPIPERIDINONE;TAA;2,2,6,6-Tetramethyl-4-oxopiperidine
• CAS NO: 826-36-8
• Molecular Formula: C₉H₁₇NO
• Molecular Weight: 155.24
• EINECS: 212-554-2
• Product Categories: Industrial/Fine Chemicals;Nitrogen cyclic compounds;API intermediates;Heterocycles;Miscellaneous Reagents
• Mol File: 826-36-8.mol
• Article Data: 33

Chemical Properties

• Melting Point: 59-61 °C
• Boiling Point: 105-105°C/18mm
• Flash Point: 73°C
• Appearance: white crystalline powder
• Density: 0.9796 (rough estimate)
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.4680 (estimate)
• Storage Temp.: Refrigerator (+4°C)
• Solubility: DMSO, Methanol
• PKA: 9.20±0.60(Predicted)
• Water Solubility: 249g/L at 20℃
• CAS DataBase Reference: Triacetonamine(CAS DataBase Reference)
• NIST Chemistry Reference: Triacetonamine(826-36-8)
• EPA Substance Registry System: Triacetonamine(826-36-8)

Safety Data

• Hazard Codes: C,Xn
• Statements: 34-22-36/37/38
• Safety Statements: 45-36/37/39-26-22-36/37
• WGK Germany: 2
• RTECS: TO0127900
• Hazardous Substances Data: 826-36-8(Hazardous Substances Data)

Usage

Triacetone amine

Triacetonamine has anti-arrhythmic and anti-myocardial ischemia effect. Take Triacetonamine as raw materials, ethanol as the solvent, perform hydrogenation reaction in the presence of catalyst (normal pressure or 3~4MPa) and obtain raw material of histamine-type light stabilizer 2,2,6,6-tetramethyl-4-piperidinol. .

Chemical Properties

Different sources of media describe the Chemical Properties of 826-36-8 differently. You can refer to the following data:
1. It appears as white or light yellow powder with the melting point being 43 ℃ and boiling point being 205 ℃. It is soluble in acetone, alcohol, ether and water. The above information is edited by the lookchem of Dai Xiongfeng.
2. white crystalline powder

Uses

Different sources of media describe the Uses of 826-36-8 differently. You can refer to the following data:
1. The product is the intermediate and pharmaceutical intermediate of histamine light stabilizer. Itself also has light-stabilizing effect. It has important application in pharmaceuticals.
2. 2,2,6,6-Tetramethyl-4-piperidinone (cas# 826-36-8) is a compound useful in organic synthesis.

Synthesis Reference(s)

Synthesis, p. 735, 1976 DOI: 10.1055/s-1976-24178

InChI:InChI=1/C9H15NO3/c1-7(11)4-10(5-8(2)12)6-9(3)13/h4-6H2,1-3H3

Synthetic route

phorone (504-20-1) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8)

Conditions	Yield
With ammonium hydroxide at -80 - 85℃;	98%
With ammonia; water
With ammonia
With ammonium hydroxide; sodium hydroxide 1.) 25 deg C, 3 days, 80 deg C, 60 min; 2.) 0-5 deg C; Yield given. Multistep reaction;
With ammonium hydroxide In water at 55 - 85℃;

4-hydroxy-2,2,6,6-tetramethylpiperidine (2403-88-5) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8)

Conditions	Yield
With C44H66O8P4Pd2; methyl vinyl ketone In water; toluene at 105℃; for 16h; Inert atmosphere; chemoselective reaction;	88%
With 13,17-bis(2-methoxycarbonylethyl)-2,7,12,18-tetramethylporphinatocobalt(II); oxygen; isovaleraldehyde In acetonitrile at 60℃; for 1h;	8 %Chromat.

acetone (67-64-1) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8)

Conditions	Yield
With ammonia at 80℃; for 12h; Temperature; Autoclave;	83.6%
With ammonium chloride In water for 72h;	33%
With ammonia

1,2,2,6,6-pentamethyl-4-piperidone (5554-54-1) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8)

Conditions	Yield
With water In acetone Heating; UV irradiation;	82%

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + cyclohexanone (108-94-1) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 7-azadispiro[5.1.58.36]hexadecan-15-one (35814-33-6) + 2,2-dimethyl-1-azaspiro[5.5]undecan-4-one (22280-51-9)

Conditions	Yield
With ammonium chloride at 60℃; for 10h;	A 16% B 30% C 52%
With ammonium chloride at 60℃; for 10h; Product distribution; Mechanism; other ketones;	A 3% B 36% C 24%
With ammonium chloride at 60℃; for 10h;	A 3% B 36% C 24%

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + octahydro-4,7-methano-inden-5-one (13380-94-4) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + C16H25NO

Conditions	Yield
With ammonium chloride at 60℃; for 10h;	A n/a B 45%

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + Norbornan-2-on (497-38-1) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + C13H21NO

Conditions	Yield
With ammonium chloride at 60℃; for 10h;	A n/a B 42%

4-oxo-2,2,6,6-tetramethylpiperidin-oxyl (45985-26-0, 2896-70-0) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 1-Ethanesulfonyl-2,2,6,6-tetramethyl-piperidin-4-one (131309-37-0)

Conditions	Yield
With ethanethiol In benzene Yields of byproduct given;	A 16% B n/a

2-propanimine (38697-07-3) + acetone (67-64-1) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + calyxamine B + calyxamine A

Conditions	Yield
With ethylenediamine In neat (no solvent) at 20℃; for 48h; Reagent/catalyst;	A 2% B n/a C n/a

2,6-diamino-2,6-dimethyl-heptan-4-one (60473-94-1) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8)

Conditions	Yield
With water

3-(α-chloro-benzyl)-2,2,6,6-tetramethyl-piperidin-4-one; hydrochloride + furan-2,3,5(4H)-trione pyridine (1:1) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + benzaldehyde (100-52-7)

acetone (67-64-1) + 4-amino-4-methylpentan-2-one (625-04-7) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8)

3-methyl-butan-2-one (563-80-4) + 2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 2,2,6-trimethyl-6-isopropyl-4-oxopiperidine (151356-86-4)

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + 2-Methylcyclopentanone (1120-72-5) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 1,7,7-Trimethyl-6-aza-spiro[4.5]decan-9-one + 1,8-Dimethyl-6-aza-dispiro[4.1.4.3]tetradecan-13-one

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + 4,4-dimethyl-pentan-2-one (590-50-1) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 2-(2,2-Dimethyl-propyl)-2,6,6-trimethyl-piperidin-4-one

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + thujone (1125-12-8) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + C16H27NO

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + 4-Phenyl-2-butanone (2550-26-7) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 2,2,6-Trimethyl-6-phenethyl-piperidin-4-one + 2,6-Dimethyl-2,6-diphenethyl-piperidin-4-one

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (464-49-3) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + C16H27NO

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + 2-Methylcyclohexanone (583-60-8) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 2,2,7-Trimethyl-1-aza-spiro[5.5]undecan-4-one

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + cyclopentanone (120-92-3) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 6-Aza-7,7-dimethyl-spiro<4.5>decan-9-on (22445-93-8) + 6-Aza-dispiro[4.1.4.3]tetradecan-13-one

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + (4-nitrophenyl)ethanone (100-19-6) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 2,2,6-Trimethyl-6-(4-nitro-phenyl)-piperidin-4-one + 2,6-Dimethyl-2,6-bis-(4-nitro-phenyl)-piperidin-4-one

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + butanone (78-93-3) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 2-ethyl-2,6,6-trimethylpiperidin-4-one (133568-79-3)

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine (556-72-9) + 3-Methylcyclohexanone (591-24-2, 625-96-7) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 2,2,8-Trimethyl-1-aza-spiro[5.5]undecan-4-one + 2,10-Dimethyl-7-aza-dispiro[5.1.5.3]hexadecan-15-one

Conditions	Yield
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts;

4-oxo-2,2,6,6-tetramethylpiperidin-oxyl (45985-26-0, 2896-70-0) → Diethyl disulfide (110-81-6) + 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 1-Ethanesulfonyl-2,2,6,6-tetramethyl-piperidin-4-one (131309-37-0)

Conditions	Yield
With ethanethiol In benzene	A 9.6 % Chromat. B 71.2 % Chromat. C 9.9 % Chromat.

4-oxo-2,2,6,6-tetramethylpiperidin-oxyl (45985-26-0, 2896-70-0) + ethanethiol (75-08-1) → Diethyl disulfide (110-81-6) + 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 1-Ethanesulfonyl-2,2,6,6-tetramethyl-piperidin-4-one (131309-37-0)

Conditions	Yield
In benzene for 24h; Product distribution; other nitroxides;	A 9.6 % Chromat. B 71.2 % Chromat. C 9.9 % Chromat.

hydrogenchloride (7647-01-0) + 1-nitroso-2,2,6,6-tetramethyl-4-piperidone (640-01-7) → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8)

hydrogenchloride (7647-01-0) + 1-nitroso-2,2,6,6-tetramethyl-4-piperidone (640-01-7) + CuCl → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8)

hydrochloride of triacetonediamine → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8)

Conditions	Yield
With water

3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one (57167-75-6) + acetic acid (64-19-7) + zinc → 2,2,6,6-Tetramethyl-4-piperidone (826-36-8)

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 2,2,6,6-tetramethyl-piperidine (768-66-1)

Conditions	Yield
With hydrogenchloride; hydrogen; platinum(IV) oxide under 1.5 Torr; for 40h;	100%
With potassium hydroxide; hydrazine hydrate In diethylene glycol at 210℃; Wolff-Kishner-Huang reduction;	83%
With potassium hydroxide; hydrazine In water; diethylene glycol at 127 - 200℃; Wolff-Kishner reduction;	82%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one (57167-75-6)

Conditions	Yield
With bromine	100%
With bromine; acetic acid at 20℃;	90%
With bromine In acetic acid at 20℃; for 24h;	84%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + methylamine hydrochloride (593-51-1) → 4-N-methylamino-2,2,6,6-tetramethylpiperidine (62995-79-3)

Conditions	Yield
With C8H14BO4(1-)*Na(1+); triethylamine In tetrahydrofuran; dichloromethane at 20℃; for 6h;	100%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → 2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate

Conditions	Yield
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃;	100%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl (45985-26-0, 2896-70-0)

Conditions	Yield
With oxone; tetrabutylammomium bromide; potassium hydroxide In dichloromethane; water; acetone at 0℃; for 3h; pH=7.5 - 8; aq. phosphate buffer;	99%
With 3,3-dimethyldioxirane In acetone at 0℃;	98%
With sodium tungstate; ethylenediaminetetraacetic acid; dihydrogen peroxide In water at -5 - 20℃; for 240h;	96%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + dimethyl amine (124-40-3) → 4-dimethylamino-2,2,6,6-tetramethyl piperidine (32327-90-5)

Conditions	Yield
With formic acid In 5,5-dimethyl-1,3-cyclohexadiene at 130 - 135℃; for 5h; Inert atmosphere;	98.3%
With formic acid In 5,5-dimethyl-1,3-cyclohexadiene at 130 - 135℃; for 6h; Solvent; Temperature; Inert atmosphere;	97.5%
With palladium 10% on activated carbon; hydrogen In methanol at -10 - 60℃; under 2250.23 Torr;

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + N-butylamine (109-73-9) → 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1)

Conditions	Yield
Pt on carbon In water	98%
With hydrogen at 100℃; under 6750.68 Torr; for 5h; Pressure; Temperature; Autoclave;	97.4%
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone; N-butylamine With acetic acid at 25℃; for 12h; Stage #2: With methanol; sodium tetrahydroborate for 8h; Temperature; Reagent/catalyst;	95.2%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + ethylamine (75-04-7) → 4-N-ethylamino-2,2,6,6-tetramethylpiperidine

Conditions	Yield
Pt on carbon In water	98%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + n-butyllithium (109-72-8, 29786-93-4) → 2,2,6,6-tetramethyl-4-n-butylpiperidin-4-ol (53725-60-3)

Conditions	Yield
In tetrahydrofuran at 20℃;	97.3%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + dimethyl sulfate (77-78-1) → 1,2,2,6,6-pentamethyl-4-piperidone (5554-54-1)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide at 45℃; for 10h; Temperature; Solvent;	97%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + propynoic acid methyl ester (922-67-8) → (E)-1-methoxycarbonyl-2-ethylene (110998-13-5)

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	96%
In methanol at 20℃; for 288h;	81%
In methanol at 20℃; for 288h;

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + ethynyl p-tolyl sulfone (13894-21-8) → 2,2,6,6-Tetramethyl-1-[(E)-2-(toluene-4-sulfonyl)-vinyl]-piperidin-4-one

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	96%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + platinum carbon + n-Octylamine (111-86-4) → N-(2,2,6,6-tetramethyl-piperidin-4-yl)-n-octylamine

Conditions	Yield
In methanol	96%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 4-hydroxy-2,2,6,6-tetramethylpiperidine (2403-88-5)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 4h;	95%
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 2h; Inert atmosphere;	93%
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 2h;	93%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 3,5-Dibromo-4-oxo-2,2,6,6-tetramethylpiperidine Hydrobromide (19971-12-1)

Conditions	Yield
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone With acetic acid at 20℃; Stage #2: With bromine at 20℃; for 16h;	95%
With bromine In acetic acid	93%
With bromine; acetic acid at 10 - 20℃; for 2h; Inert atmosphere;	91%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 4-hydroxyimino-2,2,6,6-tetramethylpiperidine (4168-79-0)

Conditions	Yield
With hydroxylamine In sulfuric acid for 1h;	95%
With hydroxylamine hydrochloride; sodium methylate In ethanol; water at 20℃; for 16h;	89.6%
With hydroxylamine hydrochloride; sodium acetate In water	18%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 2,2,6,6-Tetramethyl-4,4-bis(hydroperoxy)piperidinium-sulfat (75279-27-5)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide	95%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + ethanolamine (141-43-5) → 4-[(2-hydroxyethyl)amino]-2,2,6,6-tetramethylpiperidine (37819-95-7)

Conditions	Yield
With methanol; sodium tetrahydroborate at 20℃; for 24h;	95%
With hydrogenchloride; sodium cyanoborohydride In methanol for 72h; Ambient temperature;	61%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + n-Dodecylamine (124-22-1) → N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylamine (66545-45-7)

Conditions	Yield
With methanol; sodium tetrahydroborate at 20℃; for 24h;	95%
In methanol
With sodium tetrahydroborate In methanol at 20℃;

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + sebacic acid dihydrazide (925-83-7) → C28H52N6O2 (37762-28-0)

Conditions	Yield
With toluene-4-sulfonic acid In acetone; toluene at 110℃; for 8h;	95%

3-Bromothiophene (872-31-1) + 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 3-(2,2,6,6-tetramethyl-4-hydroxypiperid-4-yl)thiophene

Conditions	Yield
With n-butyllithium In diethyl ether at -70℃; for 3.5h;	94%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + Pentaerythritol (115-77-5) → 2,2,4,4,14,14,16,16-octamethyl-7,11,18,21-tetraoxa-3,15-diaza-trispiro[5.2.2.5.2.2]heneicosane (53463-88-0)

Conditions	Yield
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone; Pentaerythritol With toluene-4-sulfonic acid In toluene at 110℃; Dean-Stark; Stage #2: With N,N-dimethyl-formamide In toluene at 110℃; for 12h; Dean-Stark;	94%
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone; Pentaerythritol With toluene-4-sulfonic acid In toluene for 12h; Reflux; Dean-Stark trap; Stage #2: With sodium hydroxide In water; toluene	72%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + 1,12-dodecanedioyl dihydrazide (13043-99-7) → C32H60N6O2

Conditions	Yield
With toluene-4-sulfonic acid In ethanol; 1,3,5-trimethyl-benzene at 160℃; for 2h;	94%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + adipic acid dihydrazide (1071-93-8) → C24H44N6O2 (37762-27-9)

Conditions	Yield
With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene; acetone at 140℃; for 6h;	93%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + platinum carbon + N-butylamine (109-73-9) → N-butyl-2,2,6,6-tetramethyl piperidine-4-amine

Conditions	Yield
In methanol	92%
In methanol

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + potassium cyanide (151-50-8) + ammonium carbonate (506-87-6) → 1,3,8-triaza-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione (15871-54-2)

Conditions	Yield
In ethanol; water at 85℃; for 12h;	91%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + carbonic acid dimethyl ester (616-38-6) → 1,2,2,6,6-pentamethyl-4-piperidone (5554-54-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 110℃; for 3h; Reagent/catalyst; Temperature; Solvent;	91%

methanol (67-56-1) + 2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → methyl 2,2,5,5-tetramethyl-3-pyrrolidinecarboxylate (6910-74-3)

Conditions	Yield
Stage #1: methanol; 2,2,6,6-Tetramethyl-4-piperidone With sodium; potassium iodide Electrochemical reaction; Stage #2: With sodium amalgam Electrochemical reaction;	90%

Upstream product

• 67-64-1 acetone 
• 625-04-7 4-amino-4-methylpentan-2-one 
• 504-20-1 phorone 
• 60473-94-1 2,6-diamino-2,6-dimethyl-heptan-4-one 
• 7732-18-5 water 
• 38697-07-3 2-propanimine 
• 2403-88-5 4-hydroxy-2,2,6,6-tetramethylpiperidine 
• 556-72-9 2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine 
• 5554-54-1 1,2,2,6,6-pentamethyl-4-piperidone 
• 7664-41-7 ammonia 
• 57167-75-6 3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 640-01-7 1-nitroso-2,2,6,6-tetramethyl-4-piperidone 

Downstream Products

• 2403-88-5 4-hydroxy-2,2,6,6-tetramethylpiperidine 
• 15871-54-2 1,3,8-triaza-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione 
• 625-04-7 4-amino-4-methylpentan-2-one 
• 36793-27-8 7,7,9,9-tetramethyl-1,4-dioxa-8-azaspiro[4.5]decane 
• 53825-32-4 (7,7,9,9-tetramethyl-1,4-dioxa-8-aza-spiro[4.5]dec-2-yl)-methanol 
• 122586-79-2 1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-one 
• 52981-86-9 N-benzyl-2,2,6,6-tetramethyl-piperidin-4-one 

Relevant articles and documents

Preparation of triacetoneamine, an improved method

A new method for the preparation of triacetoneamine has been developed, in which, p-nitrotoluene is used as a catalyst, the yield of triacetoneamine is up to 65%.

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HETEROGENEOUS CATALYZED PROCESS FOR THE PRODUCTION OF 2,2,6,6-TETRAMETHYL-4-PIPERIDONE

The present invention relates to a process for the production of 2,2,6,6-tetramethyl-4-piperidone particularly comprising (i) providing a reactor containing a catalyst comprising a zeolitic material having a framework structure of FAU, wherein the zeolitic material comprises YO2 and X2O3 in its framework structure, wherein Y is a tetravalent element and X is a trivalent element, wherein the zeolitic material has an YO2 to X2O3 molar ratio of 16 to 175; (ii) preparing a reaction mixture comprising acetone and ammonia; (iii) contacting the catalyst in the reactor with the reaction mixture prepared in (ii) at a temperature in the range of from 40 to 250 °C for obtaining a reaction product comprising 2,2,6,6-tetramethyl-4-piperidone; wherein the mixture prepared in (ii) and contacted with the catalyst in (iii) contains less than 10 weight-% of water based on 100 weight-% of the reaction mixture.

Method for preparing intermediate 2,2,6,6-tetramethyl-4-piperidylamine

The invention relates to a method for preparing intermediate 2,2,6,6-tetramethyl-4-piperidylamine. The method is characterized by comprising the following steps: step 1), in the presence of a catalyst1, reacting acetone with ammonia gas to produce 2,2,6,6-tetramethyl-4-piperidinone and water; and step 2), in the presence of a catalyst 2, reacting the 2,2,6,6-tetramethyl-4-piperidinone with ammonia gas to produce 2,2,6,6-tetramethyl-4-piperidylimine and water, and reacting the 2,2,6,6-tetramethyl-4-piperidylimine with hydrogen gas to produce the 2,2,6,6-tetramethyl-4-piperidylamine, wherein the catalyst 1 is ammonium nitrate, and the catalyst 2 is a sodium hydroxyphenyl phosphate modified framework nickel catalyst. The method provided by the invention has the advantages of short synthetictime, a high conversion rate of the acetone and a high repeating utilization rate of the raw materials.