| 词条 | Acetone azine |
| 释义 |
| Reference = [1][2] | ImageFile = Aceto azine Structural Formula V1.svg | ImageFileR1 = Acetone azine Space Fill.png | ImageSizeR1 = 150px | ImageFileL1 = Acetone azine Ball and Stick.png | ImageSizeL1 = 150px | SystematicName = Acetone azine | PIN = 1,2-di(propan-2-ylidene)hydrazine | OtherNames = Ketazine Acetone ketazine Dimethyl ketazine 2-Propanone, 2-(1-methylethylidene)hydrazone Acetone isopropylidenehydrazone Dipropan-2-ylidenehydrazine Diisopropylidene hydrazine N-(propan-2-ylideneamino)propan-2-imine |Section1={{Chembox Identifiers | CASNo = 627-70-3 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 79085 | ChemSpiderID = 71417 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | EINECS = 211-009-6 | Beilstein = 4-01-00-03207 | SMILES = N(\=C(/C)C)=C(\\C)C | StdInChI = 1S/C6H12N2/c1-5(2)7-8-6(3)4/h1-4H3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = PFLUPZGCTVGDLV-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} |Section2={{Chembox Properties | C=6|H=12|N=2 | MolarMass = 112.17 g mol−1 | Appearance = Pale-yellow liquid | Density = 0.842 g cm−3 | MeltingPtC = -125 | BoilingPtC = 133 | RefractIndex = 1.454 }} |Section5={{Chembox Hazards | GHSPictograms = {{GHS flame}} {{GHS health hazard}} {{GHS skull and crossbones}} | GHSSignalWord = DANGER | HPhrases = {{H-phrases|226|302|311|315|319|335|350}} | PPhrases = {{P-phrases|201|261|280|305+351+338|308+313}} | NFPA-F = 2 | NFPA-H = 3 | NFPA-R = 0 | FlashPtC = 31 }} |Section6={{Chembox Related | OtherCompounds = Hydrazine Acetone }} }} Acetone azine is the simplest ketazine. It is an intermediate in some hydrazine manufacturing processes. Synthesis{{see also|Peroxide process}}Acetone azine can be prepared from acetone and hydrazine:[3] 2 (CH3)2CO + N2H4 → 2 H2O + [(CH3)2C=N]2 It can also be produced from acetone (2 eq.), ammonia (2 eq.) and hydrogen peroxide (1 eq.).[4] The first step is the formation of acetone imine, Me2C=NH; this is then oxidized by hydrogen peroxide through a complex mechanism to give 3,3-dimethyloxaziridine, which reacts with a further molecule of ammonia to produce acetone hydrazone. The hydrazone then condenses with a further molecule of acetone to produce the azine. The acetone azine product is distilled out of the reaction mixture as its azeotrope with water (n(H2O)/n(azine) ≈ 6).[5] ReactionsAcetone azine can be used to prepare acetone hydrazone[3] and 2-diazopropane.[6] Hydrazine can be produced through acid-catalysed hydrolysis of acetone azine:[7] 2 H2O + [(CH3)2C=N]2 → 2 (CH3)2CO + N2H4 References1. ^{{cite web|title=Acetone azine MSDS (Santa Cruz Biotechnology)|url=http://datasheets.scbt.com/sc-233803.pdf}} 2. ^{{cite web|title=Acetone azine MSDS (Sigma Aldrich)|url=http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=UK&language=EN&productNumber=273155&brand=ALDRICH&PageToGoToURL=null}} 3. ^1 {{OrgSynth | author = Day, A. C. |author2=Whiting, M. C. | title = Acetone Hydrazone | collvol = 6 | collvolpages = 10 | prep = cv6p0010}} 4. ^{{citation | inventor1-first = Jean-Pierre | inventor1-last = Schirmann | inventor2-first = Jean | inventor2-last = Combroux | inventor3-first = Serge Yvon | inventor3-last = Delavarenne | assignee = Produits Chimiques Ugine Kuhlmann | country-code = US | patent-number = 3972878 | title = Method for preparing azines and hydrazones | issue-date = 1976-08-03}}.{{citation | inventor1-first = Jean-Pierre | inventor1-last = Schirmann | inventor2-first = Pierre | inventor2-last = Tellier | inventor3-first = Henri | inventor3-last = Mathais | inventor4-first = Francis | inventor4-last = Weiss | assignee = Produits Chimiques Ugine Kuhlmann | country-code = US | patent-number = 3978049 | title = Process for the preparation of hydrazine compounds | issue-date = 1976-08-31}} 5. ^{{citation | inventor1-first = Jean-Pierre | inventor1-last = Schirmann | inventor2-first = Jean | inventor2-last = Combroux | inventor3-first = Serge Y. | inventor3-last = Delavarenne | assignee = Atochem | country-code = US | patent-number = 4724133 | title = Preparation of a concentrated aqueous solution of hydrazine hydrate | issue-date = 1988-02-09}} 6. ^Organic Syntheses, Coll. Vol. 6, p.392 (1988); Vol. 50, p.27 (1970). Link 7. ^{{citation | first = E. C. | last = Gilbert | title = Studies on Hydrazine. The Hydrolysis of Dimethylketazine and the Equilibrium between Hydrazine and Acetone | journal = J. Am. Chem. Soc. | year = 1929 | volume = 51 | issue = 11 | pages = 3394–3409 | doi = 10.1021/ja01386a032}}. 1 : Hydrazines |
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