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| CAS No. : | 3637-11-4 |
| Formula : | C9H17NO2 |
| M.W : | 171.24 |
| SMILES Code : | O=C1CC(C)(C)N(O)C(C)(C)C1 |
| English Name : | 1-Hydroxy-2,2,6,6-tetramethylpiperidin-4-one |
| MDL No. : | MFCD01104107 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 97% | With hydrogenchloride; sodium nitrite In water for 0.25h; | |
| In water Irradiation; yield as function of initial concentration and of dose of irradiation; | ||
| With (C6H4-t-Bu-p)2NO* In hexane at 22℃; exchange reaction of hydrogen atoms in system sterically hidered hydroxylamine-nitroxyl radical; |
| With 2-(4-nitrophenyl)-4,6-phenyl-3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yl In acetonitrile at 20℃; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | With diphenyl hydrazine In dichloromethane for 1h; Ambient temperature; | |
| 88% | With sodium dithionite In water; acetone at 20℃; for 1h; Inert atmosphere; | |
| 70% | With tetrahydroxy-1,4-quinone In water at 25℃; for 48h; |
| With ascorbic acid | ||
| With hydrogen In methanol for 1.5h; | ||
| With (+)-sodium L-ascorbate for 0.0833333h; | ||
| With hydrogen at 11℃; for 1.5h; | ||
| With N,N-bis(4-tert-butylphenyl)hydroxylamine In hexane at 22℃; exchange reaction of hydrogen atoms in system sterically hidered hydroxylamine-nitroxyl radical; | ||
| With hydrogen In dichloromethane at 20℃; | ||
| With water at 20℃; aq. phosphate buffer; Electrochemical reaction; | ||
| With water | ||
| With diethylenetriaminopentaacetic acid; sodium salt of phosphorous acid; sodium hydroxide; ascorbic acid In aq. phosphate buffer at 21.84℃; | ||
| With ascorbic acid In aq. phosphate buffer for 2h; | ||
| 80 % | With sodium dithionite; water In acetone at 20℃; Inert atmosphere; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 90% | With pyridine; dmap In tetrahydrofuran for 2.5h; Ambient temperature; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 98% | With pyridine In dichloromethane at 0℃; for 5h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; | ||
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; steel web; | ||
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; steel web; |
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; steel web; | ||
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; steel web; | ||
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; steel web; | ||
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; steel web; | ||
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; steel web; | ||
| With dihydrogen peroxide In water at 57 - 63℃; for 4 - 60h; steel web; | ||
| With dihydrogen peroxide In water at 57 - 63℃; for 4 - 60h; steel web; | ||
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; steel web; | ||
| With dihydrogen peroxide In water at 57 - 63℃; for 4 - 60h; | 1, 2, 14 Example 1 (Comparative) 9.5 mol of deionized water, 0.21 mol of NaHCO3 and 2.0 mol of triacetonamine (TAA) were placed in a jacketed 11 glass reactor provided with a glass blade stirrer, the reaction mixture was brought to a temperature of 60° C. by means of a thermostat while stirring (400 rpm) and 3.5 mol of hydrogen peroxide as a 50% strength aqueous solution were added at a uniform rate via a cool dropping funnel over a period of 4 hours. The reaction temperature was maintained at 57-63° C. The offgas formed in the process, which comprised predominantly O2, was measured volumetrically by the displacement principle. At the end of the addition, a sample of the two-phase reaction mixture was taken and the organic phase was analyzed by gas chromatography to determine the product composition. The pH of the lower aqueous phase was measured at room temperature. Example 2 (Comparative) To simulate H2O2-destroying conditions, a piece of steel mesh packing was attached to the glass blade stirrer and the experiment was otherwise carried out as in Example 1.; Example 14 (Comparative) 1960 kg of deionized water, 2.5 kmol of NaHCO3 and 22.5 kmol of TAA were placed in a 20 m3 steel reactor, a temperature of 60° C. was set and 100 kmol of 50% strength aqueous H2O2 solution were metered in over a period of 60 hours. The off gas obtained in the process was brought to an oxygen concentration of <7% by addition of N2 and was passed to appropriate disposal (offgas incineration). | |
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; | 11 Example 11 was carried out in a manner analogous to Example 2, but 0.06 mol of hydrochloric acid was used as cocatalyst in addition to the 0.21 mol of NaHCO3 used | |
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; | 9 Example 9 was carried out in a manner analogous to Example 2, but 0.06 mol of nitric acid was used as cocatalyst in addition to the 0.21 mol of NaHCO3 used. | |
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; | 13 Example 13 was carried out in a manner analogous to Example 2, but 0.06 mol of 2-ethylhexanoic acid was used as cocatalyst in addition to the 0.21 mol of NaHCO3 used. | |
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; | 6, 7 Example 6 Example 6 was carried out in a manner analogous to Example 2, but 0.15 mol of Na2HPO4*2 H2O was used as cocatalyst in addition to the 0.21 mol of NaHCO3 used. Example 7 Example 7 was carried out in a manner analogous to Example 2, but 0.05 mol of Na2HPO4.2H2O was used as cocatalyst in addition to the 0.21 mol of NaHCO3 used. | |
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; | 5 Example 5 Example 5 was carried out in a manner analogous to Example 2, but 0.06 mol of NaH2PO4*1H2O was used as cocatalyst in addition to the 0.21 mol of NaHCO3 used. | |
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; | 10 Example 10 was carried out in a manner analogous to Example 2, but 0.06 mol of H2SO4 was used as cocatalyst in addition to the 0.21 mol of NaHCO3 used. | |
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; | 12 Example 12 was carried out in a manner analogous to Example 2, but 0.06 mol of acetic acid was used as cocatalyst in addition to the 0.21 mol of NaHCO3 used. | |
| With dihydrogen peroxide In water at 57 - 63℃; for 4 - 60h; | 3, 4, 15 Example 3 Example 3 was carried out in a manner analogous to Example 2, but 0.06 mol of H3PO4 was used as cocatalyst in addition to the 0.21 mol of NaHCO3 used. Example 4 Example 4 was carried out in a manner analogous to Example 2, but 0.06 mol of H3PO4 was used as cocatalyst in addition to the 0.21 mol of NaHCO3 used.; Example 15 Example 15 was carried out in a manner analogous to Example 14, but the pH of the reaction mixture was maintained at 8-9 during the reaction time of 60 hours by addition of H3PO4 (1 kmol). | |
| With dihydrogen peroxide In water at 57 - 63℃; for 4h; | 8 Example 8 was carried out in a manner analogous to Example 2, but only NaH2PO4*1H2O (0.21 mol) and no NaHCO3 was used as catalyst. |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 6 Preparation of (2,2,6,6-tetramethyl-1,4 -dihydroxy-4-piperidinyl)bis(2-cyanoethyl)phosphine oxide EXAMPLE 6 Preparation of (2,2,6,6-tetramethyl-1,4 -dihydroxy-4-piperidinyl)bis(2-cyanoethyl)phosphine oxide The procedure of Example 1 is used except 0.05 mole of 2,2,6,6-tetramethyl-1-hydroxy-4-piperidone is used instead of the 2,2,6,6-tetramethyl-4-piperidone. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 5 Preparation of 1,3-Bis[(1-hydroxy-2,2,6,6-tetramethyl-4-piperidylidene)amino]guanidine EXAMPLE 5 Preparation of 1,3-Bis[(1-hydroxy-2,2,6,6-tetramethyl-4-piperidylidene)amino]guanidine The procedure of Example 1 is used except that 17.1 grams (0.10 mole) of 1-hydroxy-2,2,6,6-tetramethyl-4-piperidone is substituted for the 2,2,6,6-tetramethyl-4-piperidone monohydrate. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 78% | With dihydrogen peroxide In water; dimethyl sulfoxide | S.A (starting material): EXAMPLE S-A (starting material): Preparation of 1-methoxy-2,2,6,6-tetramethyl-4-piperidone. A 5.0 L 4 neck mechanically stirred flask is charged with 1oxyl-2,2,6,6-tetramethyl-4-piperidone (300 g, 1.76 moles), ferrous sulfate heptahydrate (513.7 g, 1.85 moles) and dimethylsulfoxide (1450 g). Hydrogen peroxide, 30% (279.2 g, 2.46 moles), is added over a 1 hour 45 min span. The temperature is maintained at 29-32° C. The content is stirred for an additional 30 min at 25-30° C. and then chilled below 1° C. Water (1250 ml) is added and the mixture is extracted with four 750 ml portions of ethyl acetate. The combined extracts are washed, 2*1.0 L of H2O, then 1*500 ml of saturated NaCl and then dried over anhydrous MgSO4. Ethyl acetate is evaporated and the product is distilled (82-84° C. 10.33*10-2 bar), yielding 254 g of a pale yellow oil (yield: 78% of theory; IR-spectrum: Ketone carbonyl, 1710 cm-1). |
| 78% | With dihydrogen peroxide In water; dimethyl sulfoxide | I.1 Preparation of 1-methoxy-2,2,6,6-tetramethyl-4-piperidone Preparation of 1-methoxy-2,2,6,6-tetramethyl-4-piperidone A 5.0 L 4 neck mechanically stirred flask is charged with 1oxyl-2,2,6,6-tetramethyl-4-piperidone (300 g, 1.76 moles), ferrous sulfate heptahydrate (513.7 g, 1.85 moles) and dimethylsulfoxide (1450 g). Hydrogen peroxide, 30% (279.2 g, 2.46 moles), is added over a 1 hour 45 min span. The temperature is maintained at 29-32° C. The Content is stirred for an additional 30 min at 25-30° C. and then chilled below 10° C. Water (1250 ml) is added and the mixture is extracted with four 750 ml portions of ethyl acetate. The combined extracts are washed, 2*1.0 L of H2O, then 1*500 ml of saturated NaCl and then dried over anhydrous MgSO4. Ethyl acetate is evaporated and the product is distilled (82-84° C./0.33*10-2 bar), yielding 254 g of a pale yellow oil (yield: 78% of theory; IR-spectrum: Ketone carbonyl, 1710 cm-1). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 84% | In N,N-dimethyl-formamide at 20℃; for 38h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 71% | With dihydrogen peroxide; potassium hydroxide In methanol; water; acetone at 70℃; for 2h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 73% 2: 10% | With sodium azide; acetic acid In water for 0.25h; Reflux; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In ethanol Dean-Stark; Reflux; | 3.b Put the product obtained in step a into a 500ml single neck round bottom flask,Add 50ml of absolute ethanol as a solvent, stir, and slowly add an equimolar amount of n-butylamine and then assemble the Dean-Stark device. Oil bath heating, reflux, TLC detection reaction proceeded,After the reaction, the solvent was distilled off under reduced pressure to obtain an intermediate product as an oily substance. |