Difference between revisions of "Acetone azine"
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| + | {{chembox | ||
| + | | IUPACName = acetone azine<br/>diisopropylidenehydrazine | ||
| + | | Section1 = {{Chembox Identifiers | ||
| + | | CASNo = 627-70-3 | ||
| + | | EINECS = 211-009-6 | ||
| + | | ChemSpiderID = 71417 | ||
| + | | SMILES = N(\N=C(/C)C)=C(\C)C | ||
| + | | InChI=1/C6H12N2/c1-5(2)7-8-6(3)4/h1-4H3 | ||
| + | | InChIKey = PFLUPZGCTVGDLV-UHFFFAOYAR | ||
| + | | StdInChI=1S/C6H12N2/c1-5(2)7-8-6(3)4/h1-4H3 | ||
| + | | StdInChIKey = PFLUPZGCTVGDLV-UHFFFAOYSA-N | ||
| + | }} | ||
| + | | Section2 = {{Chembox Properties | ||
| + | | Reference = <ref>{{RubberBible62nd|page=C-74}}.</ref> | ||
| + | | Formula = C<sub>6</sub>H<sub>12</sub>N<sub>2</sub> | ||
| + | | MolarMass = 112.17 g mol<sup>−1</sup> | ||
| + | | Appearance = colourless liquid | ||
| + | | MeltingPt = −12.5 °C | ||
| + | | BoilingPt = 133 °C | ||
| + | | Density = 0.8390 g cm<sup>−3</sup> | ||
| + | | RefractIndex = 1.4535 | ||
| + | }} | ||
| + | }} | ||
'''Acetone azine''', Me<sub>2</sub>C=N–N=CMe<sub>2</sub>, is the [[Condensation reaction|condensation product]] of two [[equivalent (chemistry)|equivalent]]s of [[acetone]] with one equivalent of [[hydrazine]]. It is an intermediate in the industrial production of hydrazine by the [[Atofina–PCUK cycle]].<ref>{{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}}.</ref> | '''Acetone azine''', Me<sub>2</sub>C=N–N=CMe<sub>2</sub>, is the [[Condensation reaction|condensation product]] of two [[equivalent (chemistry)|equivalent]]s of [[acetone]] with one equivalent of [[hydrazine]]. It is an intermediate in the industrial production of hydrazine by the [[Atofina–PCUK cycle]].<ref>{{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}}.</ref> | ||
| − | On a laboratory scale, acetone azine is prepared by the direct reaction of acetone with [[hydrazine hydrate]], with water being removed from the product by stirring with solid [[potassium hydroxide]] | + | On a laboratory scale, acetone azine is prepared by the direct reaction of acetone with [[hydrazine hydrate]], with water being removed from the product by stirring with solid [[potassium hydroxide]]:<ref>{{citation | first1 = T. | last1 = Curtius | first2 = K. | last2 = Thun | journal = J. Prakt. Chem. | volume = 44 | pages = 161 | year = 1891}}.</ref><ref name="OrgSynth">{{OrgSynth | first1 = A. C. | last1 = Day | first2 = M. C. | last2 = Whiting | title = Acetone hydrazone | collvol = 6 | collvolpages = 10 | volume = 50 | pages =3 | year = 1970 | prep = cv6p0010}}.</ref> it is also commercially available. It is a useful precursor to [[acetone hydrazone]]<ref name="OrgSynth"/> and hence to [[2-diazopropane]],<ref name="diazo">{{OrgSynth | first1 = S. D. | last1 = Andrews | first2 = A. C. | last2 = Day | first3 = P. | last3 = Raymond | first4 = M. C. | last4 = Whiting | title = 2-Diazopropane | collvol = 6 | collvolpages = 392 | volume = 50 | pages = 27 | year = 1970 | prep = cv6p0392}}.</ref> both of which must be prepared immediately before use and cannot be stored.<ref name="OrgSynth"/><ref name="diazo"/> |
==References== | ==References== | ||
Revision as of 09:28, 29 June 2010
| Acetone azine | |
|---|---|
| IUPAC name | acetone azine diisopropylidenehydrazine |
| Identifiers | |
| InChI | InChI=1/C6H12N2/c1-5(2)7-8-6(3)4/h1-4H3 |
| InChIKey | PFLUPZGCTVGDLV-UHFFFAOYAR |
| Standard InChI | InChI=1S/C6H12N2/c1-5(2)7-8-6(3)4/h1-4H3 |
| Standard InChIKey | PFLUPZGCTVGDLV-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| ChemSpider | |
| SMILES | |
| Properties[1] | |
| Chemical formula | C6H12N2 |
| Molar mass | 112.17 g mol−1 |
| Appearance | colourless liquid |
| Density | 0.8390 g cm−3 |
| Melting point |
−12.5 °C |
| Boiling point |
133 °C |
| Refractive index (nD) | 1.4535 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Acetone azine, Me2C=N–N=CMe2, is the condensation product of two equivalents of acetone with one equivalent of hydrazine. It is an intermediate in the industrial production of hydrazine by the Atofina–PCUK cycle.[2]
On a laboratory scale, acetone azine is prepared by the direct reaction of acetone with hydrazine hydrate, with water being removed from the product by stirring with solid potassium hydroxide:[3][4] it is also commercially available. It is a useful precursor to acetone hydrazone[4] and hence to 2-diazopropane,[5] both of which must be prepared immediately before use and cannot be stored.[4][5]
References
- ↑ CRC Handbook of Chemistry and Physics, 62nd ed.; Weast, Robert C., Ed.; CRC Press: Boca Raton, FL, 1981; p C-74. ISBN 0-8493-0462-8.
- ↑ Schirmann, Jean-Pierre; Combroux, Jean; Delavarenne, Serge Yvon (Produits Chimiques Ugine Kuhlmann) Method for preparing azines and hydrazones. US Patent 3972878, issued 3 August 1976. Schirmann, Jean-Pierre; Tellier, Pierre; Mathais, Henri, et al. (Produits Chimiques Ugine Kuhlmann) Process for the preparation of hydrazine compounds. US Patent 3978049, issued 31 August 1976.
- ↑ Curtius, T.; Thun, K. J. Prakt. Chem. 1891, 44, 161.
- ↑ 4.0 4.1 4.2 Day, A. C.; Whiting, M. C. Acetone hydrazone. Org. Synth. 1970, 50, 3, <http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0010>; Coll. Vol., 6, 10.
- ↑ 5.0 5.1 Andrews, S. D.; Day, A. C.; Raymond, P.; Whiting, M. C. 2-Diazopropane. Org. Synth. 1970, 50, 27, <http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0392>; Coll. Vol., 6, 392.
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