| Revision as of 13:53, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 410156624 of page Triacetone_amine for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 22:43, 25 March 2024 edit Mazewaxie (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers113,603 editsm WP:GENFIXESTag: AWB |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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| verifiedrevid = 410155353 |
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| Watchedfields = changed |
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| Name = Triacetone amine |
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| verifiedrevid = 470612896 |
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| ImageFile = Triacetone amine.png |
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| Name = Triacetone amine |
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| ImageFile = Triacetonamine-Structural formula V1.svg |
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| ImageName = |
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| ImageName = |
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| IUPACName = 2,2,6,6-Tetramethylpiperidinone |
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| PIN = 2,2,6,6-Tetramethylpiperidin-4-one |
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| OtherNames = Triacetone amine |
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| OtherNames = Triacetone amine |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| SMILES = O=C1CC(NC(C)(C)C1)(C)C |
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| SMILES = O=C1CC(NC(C)(C)C1)(C)C |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 12665 |
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| ChemSpiderID = 12665 |
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| PubChem = 13220 |
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| PubChem = 13220 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = JWUXJYZVKZKLTJ-UHFFFAOYSA-N |
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| StdInChIKey = JWUXJYZVKZKLTJ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 826-36-8 --> |
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| RTECS = TO0127900 |
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| CASNo = 826-36-8 |
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| RTECS = TO0127900 |
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| EC_number = 212-554-2 |
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| UNII = 2K4430S3XP |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=9|H=17|N=1|O=1 |
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| Formula = C<sub>9</sub>H<sub>17</sub>NO |
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| MolarMass = 155.23 g/mol |
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| MolarMass = |
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| Appearance = Colorless low-melting solid |
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| Appearance = Colorless low-melting solid |
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| Density = ? g/cm<sup>3</sup> |
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| Density = 0.882 g/cm<sup>3</sup> |
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| Solubility = Moderate |
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| Solubility = Moderate |
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| Solvent = other solvents |
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| Solvent = other solvents |
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| SolubleOther = Most organic solvents |
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| SolubleOther = Most organic solvents |
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| MeltingPt = 43 °C |
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| MeltingPtC = 43 |
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| BoilingPt = 205 °C |
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| BoilingPtC = 205 |
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| Section3 = {{Chembox Structure |
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| Dipole = |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = flammable |
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| MainHazards = flammable |
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| FlashPt = 164 °F |
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| FlashPtF = 164 |
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| GHSPictograms = {{GHS05}}{{GHS07}} |
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| RPhrases = 22-36/37/38 |
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| GHSSignalWord = Danger |
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| SPhrases = 26-36/37 |
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| HPhrases = {{H-phrases|290|302|314|315|317|319|335|412}} |
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| PPhrases = {{P-phrases|234|260|261|264|270|271|272|273|280|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|321|330|332+313|333+313|337+313|362|363|390|403+233|404|405|501}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherCpds = ] |
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| OtherCompounds = ] |
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'''Triacetonamine''' is an ] with the formula OC(CH<sub>2</sub>CMe<sub>2</sub>)<sub>2</sub>NH (where Me = CH<sub>3</sub>). It is a colorless or white solid that melts near room temperature. The compound is an intermediate in the preparation of ], a sterically hindered base and precursor to the reagent called ]. Triacetonamine is formed by the poly-] of acetone in the presence of ammonia and ]:<ref>{{cite journal|title=Preparation of Tetramethylpiperdine-1-oxoammonlum Salts and Their Use as Oxidants in Organic Chemistry. A Review|author=Nabyl Merbouh |author2=] |author3=Christian Brückner |year=2004|journal=Organic Preparations and Procedures International|volume=36|pages=1–31|doi=10.1080/00304940409355369|s2cid=98117103 }}</ref> |
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:3 (CH<sub>3</sub>)<sub>2</sub>CO + NH<sub>3</sub> → OC(CH<sub>2</sub>CMe<sub>2</sub>)<sub>2</sub>NH + 2 H<sub>2</sub>O |
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] of triacetonamine gives ]. |
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It is primarily used as a stabilizer for plastics, typically via its conversion to number of ], but also finds use as a chemical feedstock. It is used to prepare the ] amine ], CH<sub>2</sub><sub>2</sub>NH,<ref>Sorgi, K. L. "2,2,6,6-Tetramethylpiperidine" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. {{doi|10.1002/047084289X}}.</ref> as well as the radical oxidizer ].<ref>{{cite journal|last1=Ciriminna|first1=Rosaria|last2=Pagliaro|first2=Mario|title=Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives|journal=Organic Process Research & Development|date=15 January 2010|volume=14|issue=1|pages=245–251|doi=10.1021/op900059x}}</ref> |
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==References== |
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<references /> |
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