Difference between revisions of "Acetone azine"
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'''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]].<ref>{{citation | first1 = T. | last1 = Curtius | first2 = K. | last2 = Thun | journal = J. Prakt. Chem. | volume = 44 | pages = 161 | year = 1891}}.</ref><ref>{{OrgSynth | first1 = A. C. | last1 = Day | first2 = M. C. | last2 = Whiting | title = Acetone hydrazone | | + | 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 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 08:09, 29 June 2010
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.[1]
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.[2][3] It is a useful precursor to acetone hydrazone[3] and hence to 2-diazopropane,[4] both of which must be prepared immediately before use and cannot be stored.[3][4]
References
- ↑ 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.
- ↑ 3.0 3.1 3.2 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.
- ↑ 4.0 4.1 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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