Difference between revisions of "Hydrazine" - New World Encyclopedia

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{{Chembox new
 
{{Chembox new
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|   Name = Hydrazine
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| Name = Hydrazine
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|   ImageFile = Hydrazine-2D.png
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| ImageFile = Hydrazine-2D.png
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|   ImageFile1 = Hydrazine-3D-balls.png
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| ImageFile1 = Hydrazine-3D-balls.png
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|   ImageFile2 = Hydrazine-3D-vdW.png
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| ImageFile2 = Hydrazine-3D-vdW.png
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|   IUPACName = Hydrazine
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| IUPACName = Hydrazine
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|   OtherNames =
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| OtherNames =
 
| Section1 = {{Chembox Identifiers
 
| Section1 = {{Chembox Identifiers
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|   CASNo = 302-01-2
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| CASNo = 302-01-2
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|   RTECS = MU7175000
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| RTECS = MU7175000
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  }}
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}}
 
| Section2 = {{Chembox Properties
 
| Section2 = {{Chembox Properties
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|   Formula = N<sub>2</sub>H<sub>4</sub>
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| Formula = N<sub>2</sub>H<sub>4</sub>
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|   MolarMass = 32.05 g/mol
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| MolarMass = 32.05 g/mol
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|   Appearance = Colourless liquid
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| Appearance = Colourless liquid
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|   Density = 1.01 g/mL (liquid)
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| Density = 1.01 g/mL (liquid)
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|   Solubility = miscible
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| Solubility = miscible
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|   MeltingPt = 1 °C (274 K)  
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| MeltingPt = 1 °C (274 K)  
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|   BoilingPt = 114 °C (387 K)
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| BoilingPt = 114 °C (387 K)
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|   Viscosity = 0.9 [[Poise|cP]] at 25°C<ref name="Greenwood 1997">"Chemistry of the Elements", 2nd ed., Greenwood, N. N. and Earnshaw, A., Butterworth-Heinemann, Oxford (1997).</ref>
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| Viscosity = 0.9 [[Poise|cP]] at 25°C<ref name="Greenwood 1997">N.N. Greenwood, and A. Earnshaw, ''Chemistry of the Elements'' (Oxford, UK: Butterworth-Heinemann, 1997, ISBN 0750633654).</ref>
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  }}
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}}
 
| Section3 = {{Chembox Structure
 
| Section3 = {{Chembox Structure
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|   MolShape = pyramidal at N
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| MolShape = pyramidal at N
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|   Dipole = 1.85 [[Debye|D]]<ref name="Greenwood 1997"/>
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| Dipole = 1.85 [[Debye|D]]<ref name="Greenwood 1997"/>
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  }}
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}}
 
| Section7 = {{Chembox Hazards
 
| Section7 = {{Chembox Hazards
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|   MainHazards = Toxic,<br />causes burns
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| MainHazards = Toxic,<br />causes burns
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|   NFPA-H = 3  
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| NFPA-H = 3  
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|   NFPA-F = 3  
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| NFPA-F = 3  
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|   NFPA-R = 3
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| NFPA-R = 3
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|   FlashPt = 37.78°C (closed cup)  
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| FlashPt = 37.78°C (closed cup)  
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|   RPhrases = 45-10-23/24/25-34-43-50/53  
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| RPhrases = 45-10-23/24/25-34-43-50/53  
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|   SPhrases = 53-45-60-61
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| SPhrases = 53-45-60-61
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|   ExternalMSDS = [http://www.sciencelab.com/xMSDS-Hydrazine-9924279 External MSDS]
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| ExternalMSDS = [http://www.sciencelab.com/xMSDS-Hydrazine-9924279 External MSDS]
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  }}
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}}
 
| Section8 = {{Chembox Related
 
| Section8 = {{Chembox Related
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|   Function = hydrides
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| Function = hydrides
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|   OtherFunctn = [[hydrogen peroxide]]
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| OtherFunctn = [[hydrogen peroxide]]
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|   OtherCpds = [[ammonia]]<br />[[monomethylhydrazine]]<br />[[dimethylhydrazine]]<br/>[[phenylhydrazine]]
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| OtherCpds = [[ammonia]]<br />[[monomethylhydrazine]]<br />[[dimethylhydrazine]]<br/>[[phenylhydrazine]]
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  }}
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}}
 
}}
 
}}
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'''Hydrazine''' is the [[chemical compound]] with [[chemical formula|formula]] [[Nitrogen|N]]<sub>2</sub>[[Hydrogen|H]]<sub>4</sub>. It is widely used in chemical synthesis and is a component in some [[rocket fuel]]s. With an [[ammonia]]-like odor, hydrazine has a liquid range and density similar to water.
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'''Hydrazine''' is a [[chemical compound]] with the [[chemical formula|formula]] [[Nitrogen|N]]<sub>2</sub>[[Hydrogen|H]]<sub>4</sub>. It has an [[ammonia]]-like odor, and its liquid range and [[density]] are similar to those of [[water]]. It is widely used in chemical synthetic reactions, and it is a component of some [[rocket fuel]]s. It is, however, very toxic and dangerously unstable, especially when not mixed with water.
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{{toc}}
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==Molecular structure and properties==
  
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==Molecular structure and properties==
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Hydrazine has a simple molecular structure. Its formula may be written as H<sub>2</sub>N-NH<sub>2</sub>, to indicate that there is a [[covalent bond]] between the two [[nitrogen]] [[atom]]s. Conceptually, this structure would arise by coupling a pair of [[ammonia]] (NH<sub>3</sub>) molecules to form the N-N bond, accompanied by the loss of one hydrogen atom per ammonia molecule.
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Conceptually, hydrazine arises via coupling a pair of [[ammonia]] molecules by removal of one hydrogen per molecule. Each H<sub>2</sub>N-N subunit is pyramidal. The N-N distance is 1.45 Å, and the molecule adopts a [[gauche conformation]].<ref> Miessler, Gary L. and Tarr, Donald A. '' Inorganic Chemistry, Third Edition''.  Pearson Prentice Hall (2004).  ISBN 0-13-035471-6.</ref> The [[rotational barrier]] is twice that of [[ethane]]. These structural properties resemble that of gaseous [[hydrogen peroxide]], which adopts a "skewed" [[Linear alkane conformation| anticlinal]] conformation, and also experiences a strong rotational barrier.
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Within a hydrazine molecule, each H<sub>2</sub>N-N subunit has a pyramidal structure. The N-N distance is 1.45 angstroms (Å), and the molecule adopts a [[gauche conformation]].<ref> Gary L. Miessler, and Donald A. Tarr, ''Inorganic Chemistry'', 3rd Edition'' (Upper Saddle River, NJ: Pearson Education, 2004, ISBN 0-13-035471-6).</ref> The [[rotational barrier]] is twice that of [[ethane]]. These structural properties resemble those of gaseous [[hydrogen peroxide]], which adopts a "skewed" [[Linear alkane conformation| anticlinal]] conformation, and also experiences a strong rotational barrier.
  
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It has [[Base (chemistry)|basic]] properties comparable to [[ammonia]] but 15 times weaker.
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Like ammonia, hydrazine is a chemical [[Base (chemistry)|base]], but it is 15 times weaker than ammonia. It can receive a proton (H<sup>+</sup>) as follows:
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:N<sub>2</sub>H<sub>4</sub> + H<sup>+</sup> → [N<sub>2</sub>H<sub>5</sub>]<sup>+</sup>   K = 8.5 x 10<sup>-7</sup>
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:N<sub>2</sub>H<sub>4</sub> + H<sup>+</sup> → [N<sub>2</sub>H<sub>5</sub>]<sup>+</sup> (K = 8.5 x 10<sup>-7</sup>)
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(for ammonia K = 1.78 x 10<sup>-5</sup>)
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(for ammonia, K = 1.78 x 10<sup>-5</sup>)
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It can be diprotonated only with difficulty:<ref>Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.</ref>
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Protonated hydrazine can combine with a second proton with difficulty:<ref>A.F. Holleman, and E. Wiberg, ''Inorganic Chemistry'' (San Diego, CA: Academic Press, 2001, ISBN 0-12-352651-5).</ref>
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:[N<sub>2</sub>H<sub>5</sub>]<sup>+</sup> + H<sup>+</sup> → [N<sub>2</sub>H<sub>6</sub>]<sup>2+</sup>   K = 8.4 x 10<sup>-16</sup>
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:[N<sub>2</sub>H<sub>5</sub>]<sup>+</sup> + H<sup>+</sup> → [N<sub>2</sub>H<sub>6</sub>]<sup>2+</sup> (K = 8.4 x 10<sup>-16</sup>)
  
 
==Synthesis==
 
==Synthesis==
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[[Theodor Curtius]] synthesized free hydrazine for the first time in 1889 via a circuitous route.<ref>Curtius, J. Prakt. Chem. '''1889''', 39, 107-39.</ref>
 
  
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Hydrazine is produced in the [[Olin Raschig process]] from [[sodium hypochlorite]] and [[ammonia]], a process announced in 1907. This method relies on the reaction of [[chloramine]] with ammonia.<ref>{{OrgSynth | author = Adams, R.; Brown, B. K. | title = Hydrazine Sulfate | collvol = 1 | collvolpages = 309 | year = 1941 | prep = cv1p0309}}</ref>
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Free hydrazine was synthesized for the first time by [[Theodor Curtius]] in 1889, by a circuitous route.<ref>J. Prakt Curtius, 1889, ''Chem'' 39:107-39.</ref>
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Another synthetic process (called the [[Olin Raschig process]]) was announced in 1907, involving the use of [[sodium hypochlorite]] and [[ammonia]]. This method relies on the reaction of [[chloramine]] with ammonia.<ref>R. Adams, and B.K. Brown, 1941, [http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0309 Hydrazine Sulfate] ''Organic Syntheses, Coll.'' 1:309. Retrieved February 25, 2008.</ref>
  
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In the [[Atofina-PCUK cycle]], hydrazine is produced in several steps from [[acetone]], ammonia, and hydrogen peroxide. Acetone and ammonia first react to give the [[imine]] followed by oxidation with [[hydrogen peroxide]] to the [[oxaziridine]], a three-membered ring containing carbon, oxygen, and nitrogen, followed by [[ammonolysis]] to the [[hydrazone]], a process that couples two nitrogen atoms. This hydrazone reacts with one more equivalent of acetone, and the resulting azine is hydrolyzed to give hydrazine, regenerating acetone. Unlike the Raschig process, this process does not produce salt. The PCUK stands for Produits Chimiques Ugine Kuhlmann, a French chemical manufacturer.<ref> Riegel, Emil Raymond. "Hydrazine" Riegel's Handbook of Industrial Chemistry p. 192 (1992).</ref>
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In the [[Atofina-PCUK cycle]], hydrazine is produced in several steps from [[acetone]], ammonia, and hydrogen peroxide. Acetone and ammonia first react to give the [[imine]], followed by oxidation with [[hydrogen peroxide]] to the [[oxaziridine]], a three-membered ring containing carbon, oxygen, and nitrogen. That is followed by [[ammonolysis]] to the [[hydrazone]], a process that couples two nitrogen atoms. This hydrazone reacts with one more equivalent of acetone, and the resulting azine is hydrolyzed to give hydrazine, regenerating acetone. Unlike the Raschig process, this process does not produce salt. The PCUK stands for Produits Chimiques Ugine Kuhlmann, a French chemical manufacturer.<ref> Emil Raymond Riegel, "Hydrazine" ''Riegel's Handbook of Industrial Chemistry'' (New York, NY: Van Nostrand Reinhold, ISBN 0442001754).</ref>
  
 
Hydrazine can also be produced via the so-called [[ketazine process|ketazine]] and [[peroxide process]]es.
 
Hydrazine can also be produced via the so-called [[ketazine process|ketazine]] and [[peroxide process]]es.
  
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In 2001, Microbiologist Marc Strous from the University of Nijmegen in the Netherlands discovered that hydrazine is produced from yeast bacteria and the open ocean bacterium anammox (''Brocadia anammoxidans''). They are the only discovered organisms to naturally produce hydrazine.<ref>{{cite news | author = Brian Handwerk | url = http://news.nationalgeographic.com/news/2005/11/1109_051109_rocketfuel.html | title = Bacteria Eat Human Sewage, Produce Rocket Fuel | publisher = [[National Geographic]] | date = 9 Nov 2005 | accessdate = 2007-11-12}}</ref>
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In 2001, microbiologist Marc Strous of the University of Nijmegen in the [[Netherlands]] discovered that hydrazine is produced from yeast bacteria and the open ocean bacterium anammox ''(Brocadia anammoxidans)''. They are the only organisms known to produce hydrazine naturally.<ref>Brian Handwerk, 2005, [http://news.nationalgeographic.com/news/2005/11/1109_051109_rocketfuel.html Bacteria Eat Human Sewage, Produce Rocket Fuel] National Geographic. Retrieved February 25, 2008.</ref>
  
 
==Hydrazine derivatives==
 
==Hydrazine derivatives==
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Many substituted hydrazines are known, and several occur naturally. Some examples:
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*[[gyromitrin]] and [[agaritine]] are phenylhydrazines found in the commercially produced mushroom species ''[[Agaricus bisporus]]''. [[Gyromitrin]] is metabolized into [[monomethyl hydrazine]].
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Many substituted hydrazines are known, several of which occur naturally. Some examples include:
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*[[gyromitrin]] and [[agaritine]] are phenylhydrazines found in the commercially produced [[mushroom]] [[species]] ''[[Agaricus bisporus]]''. Gyromitrin is metabolized into [[monomethyl hydrazine]].
 
*[[iproniazid]], [[hydralazine]] and [[phenelzine]] are hydrazine-containing [[medication]]s.
 
*[[iproniazid]], [[hydralazine]] and [[phenelzine]] are hydrazine-containing [[medication]]s.
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*[[UDMH|1,1-dimethylhydrazine]] and [[1,2-dimethylhydrazine]] are hydrazines where two hydrogen atoms are replaced by [[methyl group]]s.
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*[[UDMH|1,1-dimethylhydrazine]] and [[1,2-dimethylhydrazine]] are hydrazines where two [[hydrogen]] atoms are replaced by [[methyl group]]s.
 
*[[2,4-Dinitrophenylhydrazine|2,4-dinitrophenylhydrazine]] (2,4-DNP) is commonly used to test for [[ketones]] and [[aldehydes]] in [[organic chemistry]].
 
*[[2,4-Dinitrophenylhydrazine|2,4-dinitrophenylhydrazine]] (2,4-DNP) is commonly used to test for [[ketones]] and [[aldehydes]] in [[organic chemistry]].
 
*[[phenylhydrazine]], C<sub>6</sub>H<sub>5</sub>NHNH<sub>2</sub>, the first hydrazine to be discovered.
 
*[[phenylhydrazine]], C<sub>6</sub>H<sub>5</sub>NHNH<sub>2</sub>, the first hydrazine to be discovered.
  
 
==Uses in chemistry==
 
==Uses in chemistry==
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Hydrazines are part of many [[organic syntheses]], often those of practical significance in [[pharmaceutical]]s, such as [[antituberculant]]s, as well as in textile [[dye]]s and in photography.
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 +
Hydrazines are part of many [[organic syntheses]], many of which are of practical significance in [[pharmaceutical]]s, such as [[antituberculant]]s, as well as in textile [[dye]]s and in photography.
  
 
===Hydrazone formation===
 
===Hydrazone formation===
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Illustrative of the condensation of hydrazine with a simple carbonyl is its reaction with [[acetone]] to give the [[azine]].  This azine reacts further with hydrazine to afford the hydrazone:<ref>{{OrgSynth | author = Day,  A. C.; Whiting,  M. C. | title = Acetone Hydrazone | collvol = 6 | collvolpages = 10 | prep = cv6p0010}}</ref>
 
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:2 (CH<sub>3</sub>)<sub>2</sub>CO  +  N<sub>2</sub>H<sub>4</sub>  →  2 H<sub>2</sub>O  +  [(CH<sub>3</sub>)<sub>2</sub>C=N]<sub>2</sub>
 
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:[(CH<sub>3</sub>)<sub>2</sub>C=N]<sub>2</sub>  +  N<sub>2</sub>H<sub>4</sub>  →  2 (CH<sub>3</sub>)<sub>2</sub>C=NNH<sub>2</sub>
 
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The acetone azine is an intermediate in the Atofina-PCUK synthesis.  Direct [[alkylation]] of hydrazines with [[alkyl halides]] in the presence of base affords alkyl-substituted hydrazines, but the reaction is typically inefficient due to poor control on level of substitution (same as in ordinary [[amine]]s).  The reduction of [[hydrazone]]s to hydrazines present a  clean way to produce 1,1-dialkylated hydrazines.
 
  
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In a related reaction 2-cyano[[pyridine]]s react with hydrazine to form amide hydrazides which can be converted using 1,2-diketones into [[triazines]].
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Hydrazine undergoes a condensation reaction with [[acetone]] to give the [[azine]]. This azine reacts further with hydrazine to produce the hydrazone:<ref>A.C. Day, and M.C. Whiting, 1988, [http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0010 Acetone Hydrazone] ''Organic Syntheses, Coll.'' 6:10. Retrieved February 25, 2008.</ref>
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:2 (CH<sub>3</sub>)<sub>2</sub>CO + N<sub>2</sub>H<sub>4</sub> → 2 H<sub>2</sub>O + [(CH<sub>3</sub>)<sub>2</sub>C=N]<sub>2</sub>
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:[(CH<sub>3</sub>)<sub>2</sub>C=N]<sub>2</sub> + N<sub>2</sub>H<sub>4</sub> → 2 (CH<sub>3</sub>)<sub>2</sub>C=NNH<sub>2</sub>
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The acetone azine is an intermediate in the Atofina-PCUK synthesis. Direct [[alkylation]] of hydrazines with [[alkyl halides]] in the presence of base produces alkyl-substituted hydrazines, but the reaction is typically inefficient due to poor control on the level of substitution (same as in ordinary [[amine]]s). The reduction of [[hydrazone]]s to hydrazines present a clean way to produce 1,1-dialkylated hydrazines.
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 +
In a related reaction 2-cyano[[pyridine]]s react with hydrazine to form amide hydrazides, which can be converted using 1,2-diketones into [[triazines]].
  
 
===Wolff-Kishner reduction===
 
===Wolff-Kishner reduction===
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Hydrazine is used in the [[Wolff-Kishner reduction]], a reaction that transforms the [[carbonyl]] group of a [[ketone]] or [[aldehyde]] into a [[methylene]] (or [[methyl]]) group via a [[hydrazone]] intermediate. The production of the highly stable [[dinitrogen]] from the hydrazine derivative helps to drive the reaction.
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 +
Hydrazine is used in the [[Wolff-Kishner reduction]], a reaction that transforms the [[carbonyl]] group of a [[ketone]] or [[aldehyde]] into a [[methylene]] (or [[methyl]]) group via a [[hydrazone]] intermediate. The production of the highly stable [[dinitrogen]] from the hydrazine derivative helps drive the reaction.
  
 
===Heterocyclic chemistry===
 
===Heterocyclic chemistry===
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Being bifunctional, with two amines, hydrazine is a key building block for the preparation of many heterocyclic compounds via condensation with a range of difunctional [[electrophiles]]. With [[2,4-pentanedione]], it condenses to give the [[3,5-dimethylpyrazole]].<ref>{{OrgSynth | author = Wiley, R. H.; Hexner, P. E. | title = 3,5-Dimethylpyrazole | collvol = 4 | collvolpages = 351 | prep = cv4p0351}}</ref> In the [[Einhorn-Brunner reaction]] hydrazines react with imides to give [[triazole]]s.
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 +
Being bifunctional, with two amine groups, hydrazine is a key building block for the preparation of many heterocyclic compounds via condensation, with a range of difunctional [[electrophiles]]. With [[2,4-pentanedione]], it condenses to give the [[3,5-dimethylpyrazole]].<ref>R.H. Wiley, and P.E. Hexner, 1963, [http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0351 3,5-Dimethylpyrazole] ''Organic Syntheses, Coll.'' 4:351. Retrieved February 25, 2008.</ref> In the [[Einhorn-Brunner reaction]], hydrazines react with imides to give [[triazole]]s.
  
 
===Sulfonation===
 
===Sulfonation===
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Being a good nucleophile, N<sub>2</sub>H<sub>4</sub> is susceptible to attack by sulfonyl halides and acyl halides.<ref>{{OrgSynth | author = Friedman, L; Litle, R. L.; Reichle, W. R. | title = ''p''-Toluenesulfonyl Hydrazide | collvol = 5 | collvolpages = 1055 | prep = cv5p1055}}</ref> The [[tosyl]]hydrazine also forms hydrazones upon treatment with carbonyls.
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 +
Being a good nucleophile, N<sub>2</sub>H<sub>4</sub> is susceptible to attack by sulfonyl halides and acyl halides.<ref>L. Friedman, R.L. Litle, and W.R. Reichle, 1973, [http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p1055 ''p''-Toluenesulfonyl Hydrazide] ''Organic Syntheses, Coll''. 5:1055. Retrieved February 25, 2008.</ref> The [[tosyl]]hydrazine also forms hydrazones upon treatment with carbonyls.
  
 
===Deprotection of phthalimides===
 
===Deprotection of phthalimides===
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Hydrazine is used to cleave ''N''-alkylated phthalimide derivatives. This scission reaction allows phthalimide anion to be used as amine precursor in the [[Gabriel synthesis]].<ref>{{OrgSynth | author = Weinshenker, N. M.; Shen, C. M.; Wong, J. Y. | title = Polymeric carbodiimide | collvol = 6 | collvolpages = 951 | year = 1988 | prep = cv6p0951}}</ref>
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 +
Hydrazine is used to cleave ''N''-alkylated phthalimide derivatives. This scission reaction allows the phthalimide anion to be used as an amine precursor in the [[Gabriel synthesis]].<ref>N.M. Weinshenker, C.M. Shen, and J.Y. Wong, 1988, [http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0951 Polymeric carbodiimide] ''Organic Syntheses, Coll''. 6:951. Retrieved February 25, 2008.</ref>
  
 
===Reducing agent===
 
===Reducing agent===
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Hydrazine is a convenient reductant because the by-products are typically nitrogen gas and water. Thus, it is used as an [[antioxidant]], an oxygen [[scavenger (chemistry)|scavenger]], and a [[corrosion inhibitor]] in water boilers and heating systems. It is also used to reduce metal salts and oxides to the pure metals in [[electroless nickel plating|electroless]] [[nickel]] plating and [[plutonium]] extraction from [[nuclear waste|nuclear reactor waste]].
+
 
 +
Hydrazine is a convenient reductant because the by-products are typically nitrogen gas and water. Thus, it is used as an [[antioxidant]], an oxygen [[scavenger (chemistry)|scavenger]], and a [[corrosion inhibitor]] in water boilers and heating systems. It is also used to reduce metal salts and oxides to the pure metals in [[electroless nickel plating|electroless]] [[nickel]] plating and [[plutonium]] extraction from [[nuclear waste|nuclear reactor waste]].
  
 
===Hydrazinium salts===
 
===Hydrazinium salts===
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Hydrazine is converted to solid salts by treatment with mineral acids. A common salt is hydrazine hydrogen [[sulfate]], [N<sub>2</sub>H<sub>5</sub>]HSO<sub>4</sub>, which probably should be called hydrazinium bisulfate. Hydrazine bisulfate is used as an alternative treatment of cancer-induced [[cachexia]]. The salt of hydrazine and [[hydrazoic acid]] N<sub>5</sub>H<sub>5</sub> was of scientific interest, because of the high nitrogen content and the explosive properties.
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 +
Hydrazine is converted to solid salts by treatment with mineral acids. A common salt is hydrazine hydrogen [[sulfate]], [N<sub>2</sub>H<sub>5</sub>]HSO<sub>4</sub>, which probably should be called hydrazinium bisulfate. Hydrazine bisulfate is used as an alternative treatment of cancer-induced [[cachexia]]. The salt of hydrazine and [[hydrazoic acid]] N<sub>5</sub>H<sub>5</sub> was of scientific interest, because of the high nitrogen content and the explosive properties.
  
 
==Other industrial uses==
 
==Other industrial uses==
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Hydrazine is used in many processes including: production of [[spandex]] fibers, as a [[polymerization]] [[catalyst]]; a [[blowing agent]]; in [[fuel cell]]s, [[solder]] [[flux (metallurgy)|fluxes]]; and [[photographic developer]]s, as a [[chain extender]] in [[polyurethane|urethane]] polymerizations, and heat stabilizers. In addition, a semiconductor deposition technique using hydrazine has recently been demonstrated, with possible application to the manufacture of [[thin-film transistor]]s used in [[liquid crystal display]]s. Hydrazine in a 70% hydrazine, 30% water solution is used to power the EPU ([[emergency power unit]]) on the [[F-16]] fighter plane. The explosive [[Astrolite]] is made by combining hydrazine with [[ammonium nitrate]].
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 +
Hydrazine is used in many processes. Examples include: production of [[spandex]] fibers, as a [[polymerization]] [[catalyst]]; a [[blowing agent]]; in [[fuel cell]]s, [[solder]] [[flux (metallurgy)|fluxes]]; and [[photographic developer]]s, as a [[chain extender]] in [[polyurethane|urethane]] polymerizations, and heat stabilizers. In addition, a semiconductor deposition technique using hydrazine has recently been demonstrated, with possible application to the manufacture of [[thin-film transistor]]s used in [[liquid crystal display]]s. A solution of 70 percent hydrazine and 30 percent water is used to power the EPU ([[emergency power unit]]) on the [[F-16]] fighter plane. The explosive [[Astrolite]] is made by combining hydrazine with [[ammonium nitrate]].
  
 
===Rocket fuel===
 
===Rocket fuel===
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Hydrazine was first used as a [[rocket fuel]] during [[World War II]] for the [[Messerschmitt Me 163#Me 163 B|Messerschmitt Me 163B]] (the first rocket-powered fighter plane), under the name '''B-Stoff''' (hydrazine [[hydrate]]) and in a mixture with [[methanol]] ([[M-Stoff]]) and [[hydrogen peroxide]] called [[C-Stoff]].
 
  
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Hydrazine is also used as a low-power [[monopropellant]] for the maneuvering thrusters of spacecraft, and the [[Space Shuttle]]'s Auxiliary Power Units. In addition, monopropellant hydrazine-fueled rocket engines are often used in terminal descent of spacecraft. A collection of such engines were used in both [[Viking program|Viking]] landers as well as the [[Phoenix (spacecraft)|Phoenix]] lander launched in August 2007.
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Hydrazine was first used as a [[rocket fuel]] during [[World War II]] for the [[Messerschmitt Me 163#Me 163 B|Messerschmitt Me 163B]] (the first rocket-powered fighter plane), under the name ''B-Stoff'' (hydrazine [[hydrate]]) and in a mixture with [[methanol]] ([[M-Stoff]]) and [[hydrogen peroxide]] called [[C-Stoff]].
 +
 
 +
Hydrazine is also used as a low-power [[monopropellant]] for the maneuvering thrusters of spacecraft, and the [[Space Shuttle]]'s Auxiliary Power Units. In addition, monopropellant hydrazine-fueled rocket engines are often used in terminal descent of spacecraft. A collection of such engines were used in both [[Viking program|Viking]] landers as well as the [[Phoenix (spacecraft)|Phoenix]] lander launched in August 2007.
  
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In all hydrazine monopropellant engines the hydrazine is passed by a [[catalyst]] such as [[iridium]] metal supported by high-surface-area [[alumina]] (aluminium oxide) or [[carbon nanofiber]]s,<ref name="Vieira">{{cite journal | last = Vieira | first = R. | coauthors = C. Pham-Huu, N. Keller and M. J. Ledoux | year = 2002 | title = New carbon nanofiber/graphite felt composite for use as a catalyst support for hydrazine catalytic decomposition | journal = [[Chemical Communications]] | issue = 9 | pages = 954&mdash;955 | doi = 10.1039/b202032g}}</ref> or more recently [[molybdenum nitride]] on alumina,<ref name="Chen">{{cite journal | last = Chen | first = Xiaowei | coauthors = ''et al.'' | year = 2002 | month = April | title = Catalytic Decomposition of Hydrazine over Supported Molybdenum Nitride Catalysts in a Monopropellant Thruster | journal = [[Catalysis Letters]] | volume = 79 | pages = 21&ndash;25 | doi = 10.1023/A:1015343922044 }}</ref> which causes it to decompose into [[ammonia]], nitrogen gas, and hydrogen gas according to the following reactions:
+
In all hydrazine monopropellant engines, the hydrazine is passed by a [[catalyst]] such as [[iridium]] metal supported by high-surface-area [[alumina]] (aluminum oxide) or [[carbon nanofiber]]s,<ref name="Vieira">R. Vieira, C. Pham-Huu, N. Keller and M. J. Ledoux, 2002, New carbon nanofiber/graphite felt composite for use as a catalyst support for hydrazine catalytic decomposition, ''Chemical Communications'' 9:954&mdash;955.</ref> or more recently [[molybdenum nitride]] on alumina,<ref name="Chen">Xiaowei Chen, et al., 2002, Catalytic Decomposition of Hydrazine over Supported Molybdenum Nitride Catalysts in a Monopropellant Thruster, ''Catalysis Letters.'' 79:21&ndash;25.</ref> which causes it to decompose into [[ammonia]], nitrogen gas, and hydrogen gas according to the following reactions:
  
 
#3 N<sub>2</sub>H<sub>4</sub> → 4 NH<sub>3</sub> + N<sub>2</sub>
 
#3 N<sub>2</sub>H<sub>4</sub> → 4 NH<sub>3</sub> + N<sub>2</sub>
Line 115: Line 131:
 
These reactions are extremely [[exothermic]] (the catalyst chamber can reach 800 °C in a matter of milliseconds<ref name="Vieira" />), and they produce large volumes of hot gas from a small volume of liquid hydrazine,<ref name="Chen" /> making it an efficient thruster propellant.
 
These reactions are extremely [[exothermic]] (the catalyst chamber can reach 800 °C in a matter of milliseconds<ref name="Vieira" />), and they produce large volumes of hot gas from a small volume of liquid hydrazine,<ref name="Chen" /> making it an efficient thruster propellant.
  
−
Other variants of Hydrazine that are used as rocket fuel are [[monomethylhydrazine]], CH<sub>3</sub>NHNH<sub>2</sub> (also known as MMH) and [[unsymmetrical dimethylhydrazine]], (CH<sub>3</sub>)<sub>2</sub>NNH<sub>2</sub> (also known as UDMH). These are used as two component rocket fuel, often together with [[dinitrogen tetroxide]], N<sub>2</sub>O<sub>4</sub>.
+
Other variants of hydrazine that are used as rocket fuel are [[monomethylhydrazine]], CH<sub>3</sub>NHNH<sub>2</sub> (also known as MMH) and [[unsymmetrical dimethylhydrazine]], (CH<sub>3</sub>)<sub>2</sub>NNH<sub>2</sub> (also known as UDMH). These are used as two-component rocket fuel, often together with [[dinitrogen tetroxide]], N<sub>2</sub>O<sub>4</sub>.
  
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==Safety==
+
==Toxicity==
−
Hydrazine is highly toxic and dangerously unstable, especially in the [[anhydrous]] form. Symptoms of acute exposure to high levels of hydrazine may include irritation of the eyes, nose, and throat, dizziness, headache, nausea, [[pulmonary edema]], seizures, and coma in humans. Acute exposure can also damage the liver, kidneys, and central nervous system in humans. The liquid is corrosive and may produce [[dermatitis]] from skin contact in humans and animals. Effects to the lungs, liver, spleen, and thyroid have been reported in animals chronically exposed to hydrazine via inhalation. Increased incidences of lung, nasal cavity, and liver tumors have been observed in rodents exposed to hydrazine.
 
  
−
==References==
+
Hydrazine is highly toxic and dangerously unstable, especially in the [[anhydrous]] form. Symptoms of acute exposure to high levels of hydrazine may include irritation of the eyes, nose, and throat, dizziness, headache, nausea, [[pulmonary edema]], seizures, and coma in humans. Acute exposure can also damage the [[liver]], [[kidney]]s, and central [[nervous system]] in [[human]]s. The liquid is corrosive and may produce [[dermatitis]] from skin contact in humans and [[animal]]s. Effects to the lungs, liver, spleen, and thyroid have been reported in animals chronically exposed to hydrazine via inhalation. Increased incidences of lung, nasal cavity, and liver tumors have been observed in rodents exposed to hydrazine.
−
<div class="references-small">
+
 
 +
==See also==
 +
 
 +
* [[Ammonia]]
 +
* [[Hydrogen peroxide]]
 +
* [[Nitrogen]]
 +
 
 +
== Notes ==
 
<references />
 
<references />
−
</div>
 
  
−
==See also==
+
==References==
−
* [[List of Stoffs]]
+
* Parker, Phillip M. 2006. ''The 2007 Import and Export Market for Organic Derivatives of Hydrazine or Hydroxylamine in United Kingdom''. San Diego, CA: ICON Group International, Inc. ISBN 0546028152
 +
* Schmidt, Eckart Walter. 2001. ''Hydrazine and its Derivatives : Preparation, Properties, Applications''. New York, NY: Wiley-Interscience. ISBN 0471415537
 +
* Toth, Bela. 2000. ''Hydrazines and Cancer: A Guidebook on the Carcinogenic Activities of Hydrazines, Related Chemicals, and Hydrazine Containing Natural Products''. Amsterdam, NL: Harwood Academic Publishers. ISBN 9057026317
  
 
==External links==
 
==External links==
−
* [http://www.princeton.edu/~orggroup/supergroup_pdf/rmatunasAGM5hydrazine.pdf The Late Show with Rob! Tonight’s Special Guest: Hydrazine (PDF)]&nbsp;&mdash; Robert Matunas
+
All links retrieved January 22, 2018.
 +
* Matunas, Robert. [http://www.princeton.edu/~orggroup/supergroup_pdf/rmatunasAGM5hydrazine.pdf The Late Show with Rob! Tonight’s Special Guest: Hydrazine (PDF)]  
  
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[[Category:Hydrazines| ]]
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[[Category:Physical sciences]]
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[[Category:Bases]]
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[[Category:Chemistry]]
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[[Category:Functional groups]]
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[[Category:Inorganic chemistry]]
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[[Category:Hazardous air pollutants]]
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[[Category:Environmental science]]
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[[Category:Nitrogen compounds]]
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[[Category:Energy technology]]
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[[Category:Rocket fuels]]
 
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[[Category:Monopropellants]]
 
  
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Latest revision as of 19:54, 22 January 2018


Hydrazine
Hydrazine-2D.png
Hydrazine-3D-balls.png
Hydrazine-3D-vdW.png
IUPAC name Hydrazine
Identifiers
CAS number [302-01-2]
RTECS number MU7175000
Properties
Molecular formula N2H4
Molar mass 32.05 g/mol
Appearance Colourless liquid
Density 1.01 g/mL (liquid)
Melting point

1 °C (274 K)

Boiling point

114 °C (387 K)

Solubility in water miscible
Viscosity 0.9 cP at 25°C[1]
Structure
Molecular shape pyramidal at N
Dipole moment 1.85 D[1]
Hazards
MSDS External MSDS
Main hazards Toxic,
causes burns
NFPA 704

NFPA 704.svg

3
3
3
 
R-phrases 45-10-23/24/25-34-43-50/53
S-phrases 53-45-60-61
Flash point 37.78°C (closed cup)
Related Compounds
Related hydrides hydrogen peroxide
Related compounds ammonia
monomethylhydrazine
dimethylhydrazine
phenylhydrazine
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Hydrazine is a chemical compound with the formula N2H4. It has an ammonia-like odor, and its liquid range and density are similar to those of water. It is widely used in chemical synthetic reactions, and it is a component of some rocket fuels. It is, however, very toxic and dangerously unstable, especially when not mixed with water.

Molecular structure and properties

Hydrazine has a simple molecular structure. Its formula may be written as H2N-NH2, to indicate that there is a covalent bond between the two nitrogen atoms. Conceptually, this structure would arise by coupling a pair of ammonia (NH3) molecules to form the N-N bond, accompanied by the loss of one hydrogen atom per ammonia molecule.

Within a hydrazine molecule, each H2N-N subunit has a pyramidal structure. The N-N distance is 1.45 angstroms (Å), and the molecule adopts a gauche conformation.[2] The rotational barrier is twice that of ethane. These structural properties resemble those of gaseous hydrogen peroxide, which adopts a "skewed" anticlinal conformation, and also experiences a strong rotational barrier.

Like ammonia, hydrazine is a chemical base, but it is 15 times weaker than ammonia. It can receive a proton (H+) as follows:

N2H4 + H+ → [N2H5]+ (K = 8.5 x 10-7)

(for ammonia, K = 1.78 x 10-5) Protonated hydrazine can combine with a second proton with difficulty:[3]

[N2H5]+ + H+ → [N2H6]2+ (K = 8.4 x 10-16)

Synthesis

Free hydrazine was synthesized for the first time by Theodor Curtius in 1889, by a circuitous route.[4]

Another synthetic process (called the Olin Raschig process) was announced in 1907, involving the use of sodium hypochlorite and ammonia. This method relies on the reaction of chloramine with ammonia.[5]

In the Atofina-PCUK cycle, hydrazine is produced in several steps from acetone, ammonia, and hydrogen peroxide. Acetone and ammonia first react to give the imine, followed by oxidation with hydrogen peroxide to the oxaziridine, a three-membered ring containing carbon, oxygen, and nitrogen. That is followed by ammonolysis to the hydrazone, a process that couples two nitrogen atoms. This hydrazone reacts with one more equivalent of acetone, and the resulting azine is hydrolyzed to give hydrazine, regenerating acetone. Unlike the Raschig process, this process does not produce salt. The PCUK stands for Produits Chimiques Ugine Kuhlmann, a French chemical manufacturer.[6]

Hydrazine can also be produced via the so-called ketazine and peroxide processes.

In 2001, microbiologist Marc Strous of the University of Nijmegen in the Netherlands discovered that hydrazine is produced from yeast bacteria and the open ocean bacterium anammox (Brocadia anammoxidans). They are the only organisms known to produce hydrazine naturally.[7]

Hydrazine derivatives

Many substituted hydrazines are known, several of which occur naturally. Some examples include:

  • gyromitrin and agaritine are phenylhydrazines found in the commercially produced mushroom species Agaricus bisporus. Gyromitrin is metabolized into monomethyl hydrazine.
  • iproniazid, hydralazine and phenelzine are hydrazine-containing medications.
  • 1,1-dimethylhydrazine and 1,2-dimethylhydrazine are hydrazines where two hydrogen atoms are replaced by methyl groups.
  • 2,4-dinitrophenylhydrazine (2,4-DNP) is commonly used to test for ketones and aldehydes in organic chemistry.
  • phenylhydrazine, C6H5NHNH2, the first hydrazine to be discovered.

Uses in chemistry

Hydrazines are part of many organic syntheses, many of which are of practical significance in pharmaceuticals, such as antituberculants, as well as in textile dyes and in photography.

Hydrazone formation

Hydrazine undergoes a condensation reaction with acetone to give the azine. This azine reacts further with hydrazine to produce the hydrazone:[8]

2 (CH3)2CO + N2H4 → 2 H2O + [(CH3)2C=N]2
[(CH3)2C=N]2 + N2H4 → 2 (CH3)2C=NNH2

The acetone azine is an intermediate in the Atofina-PCUK synthesis. Direct alkylation of hydrazines with alkyl halides in the presence of base produces alkyl-substituted hydrazines, but the reaction is typically inefficient due to poor control on the level of substitution (same as in ordinary amines). The reduction of hydrazones to hydrazines present a clean way to produce 1,1-dialkylated hydrazines.

In a related reaction 2-cyanopyridines react with hydrazine to form amide hydrazides, which can be converted using 1,2-diketones into triazines.

Wolff-Kishner reduction

Hydrazine is used in the Wolff-Kishner reduction, a reaction that transforms the carbonyl group of a ketone or aldehyde into a methylene (or methyl) group via a hydrazone intermediate. The production of the highly stable dinitrogen from the hydrazine derivative helps drive the reaction.

Heterocyclic chemistry

Being bifunctional, with two amine groups, hydrazine is a key building block for the preparation of many heterocyclic compounds via condensation, with a range of difunctional electrophiles. With 2,4-pentanedione, it condenses to give the 3,5-dimethylpyrazole.[9] In the Einhorn-Brunner reaction, hydrazines react with imides to give triazoles.

Sulfonation

Being a good nucleophile, N2H4 is susceptible to attack by sulfonyl halides and acyl halides.[10] The tosylhydrazine also forms hydrazones upon treatment with carbonyls.

Deprotection of phthalimides

Hydrazine is used to cleave N-alkylated phthalimide derivatives. This scission reaction allows the phthalimide anion to be used as an amine precursor in the Gabriel synthesis.[11]

Reducing agent

Hydrazine is a convenient reductant because the by-products are typically nitrogen gas and water. Thus, it is used as an antioxidant, an oxygen scavenger, and a corrosion inhibitor in water boilers and heating systems. It is also used to reduce metal salts and oxides to the pure metals in electroless nickel plating and plutonium extraction from nuclear reactor waste.

Hydrazinium salts

Hydrazine is converted to solid salts by treatment with mineral acids. A common salt is hydrazine hydrogen sulfate, [N2H5]HSO4, which probably should be called hydrazinium bisulfate. Hydrazine bisulfate is used as an alternative treatment of cancer-induced cachexia. The salt of hydrazine and hydrazoic acid N5H5 was of scientific interest, because of the high nitrogen content and the explosive properties.

Other industrial uses

Hydrazine is used in many processes. Examples include: production of spandex fibers, as a polymerization catalyst; a blowing agent; in fuel cells, solder fluxes; and photographic developers, as a chain extender in urethane polymerizations, and heat stabilizers. In addition, a semiconductor deposition technique using hydrazine has recently been demonstrated, with possible application to the manufacture of thin-film transistors used in liquid crystal displays. A solution of 70 percent hydrazine and 30 percent water is used to power the EPU (emergency power unit) on the F-16 fighter plane. The explosive Astrolite is made by combining hydrazine with ammonium nitrate.

Rocket fuel

Hydrazine was first used as a rocket fuel during World War II for the Messerschmitt Me 163B (the first rocket-powered fighter plane), under the name B-Stoff (hydrazine hydrate) and in a mixture with methanol (M-Stoff) and hydrogen peroxide called C-Stoff.

Hydrazine is also used as a low-power monopropellant for the maneuvering thrusters of spacecraft, and the Space Shuttle's Auxiliary Power Units. In addition, monopropellant hydrazine-fueled rocket engines are often used in terminal descent of spacecraft. A collection of such engines were used in both Viking landers as well as the Phoenix lander launched in August 2007.

In all hydrazine monopropellant engines, the hydrazine is passed by a catalyst such as iridium metal supported by high-surface-area alumina (aluminum oxide) or carbon nanofibers,[12] or more recently molybdenum nitride on alumina,[13] which causes it to decompose into ammonia, nitrogen gas, and hydrogen gas according to the following reactions:

  1. 3 N2H4 → 4 NH3 + N2
  2. N2H4 → N2 + 2 H2
  3. 4 NH3 + N2H4 → 3 N2 + 8 H2

These reactions are extremely exothermic (the catalyst chamber can reach 800 °C in a matter of milliseconds[12]), and they produce large volumes of hot gas from a small volume of liquid hydrazine,[13] making it an efficient thruster propellant.

Other variants of hydrazine that are used as rocket fuel are monomethylhydrazine, CH3NHNH2 (also known as MMH) and unsymmetrical dimethylhydrazine, (CH3)2NNH2 (also known as UDMH). These are used as two-component rocket fuel, often together with dinitrogen tetroxide, N2O4.

Toxicity

Hydrazine is highly toxic and dangerously unstable, especially in the anhydrous form. Symptoms of acute exposure to high levels of hydrazine may include irritation of the eyes, nose, and throat, dizziness, headache, nausea, pulmonary edema, seizures, and coma in humans. Acute exposure can also damage the liver, kidneys, and central nervous system in humans. The liquid is corrosive and may produce dermatitis from skin contact in humans and animals. Effects to the lungs, liver, spleen, and thyroid have been reported in animals chronically exposed to hydrazine via inhalation. Increased incidences of lung, nasal cavity, and liver tumors have been observed in rodents exposed to hydrazine.

See also

Notes

  1. ↑ 1.0 1.1 N.N. Greenwood, and A. Earnshaw, Chemistry of the Elements (Oxford, UK: Butterworth-Heinemann, 1997, ISBN 0750633654).
  2. ↑ Gary L. Miessler, and Donald A. Tarr, Inorganic Chemistry, 3rd Edition (Upper Saddle River, NJ: Pearson Education, 2004, ISBN 0-13-035471-6).
  3. ↑ A.F. Holleman, and E. Wiberg, Inorganic Chemistry (San Diego, CA: Academic Press, 2001, ISBN 0-12-352651-5).
  4. ↑ J. Prakt Curtius, 1889, Chem 39:107-39.
  5. ↑ R. Adams, and B.K. Brown, 1941, Hydrazine Sulfate Organic Syntheses, Coll. 1:309. Retrieved February 25, 2008.
  6. ↑ Emil Raymond Riegel, "Hydrazine" Riegel's Handbook of Industrial Chemistry (New York, NY: Van Nostrand Reinhold, ISBN 0442001754).
  7. ↑ Brian Handwerk, 2005, Bacteria Eat Human Sewage, Produce Rocket Fuel National Geographic. Retrieved February 25, 2008.
  8. ↑ A.C. Day, and M.C. Whiting, 1988, Acetone Hydrazone Organic Syntheses, Coll. 6:10. Retrieved February 25, 2008.
  9. ↑ R.H. Wiley, and P.E. Hexner, 1963, 3,5-Dimethylpyrazole Organic Syntheses, Coll. 4:351. Retrieved February 25, 2008.
  10. ↑ L. Friedman, R.L. Litle, and W.R. Reichle, 1973, p-Toluenesulfonyl Hydrazide Organic Syntheses, Coll. 5:1055. Retrieved February 25, 2008.
  11. ↑ N.M. Weinshenker, C.M. Shen, and J.Y. Wong, 1988, Polymeric carbodiimide Organic Syntheses, Coll. 6:951. Retrieved February 25, 2008.
  12. ↑ 12.0 12.1 R. Vieira, C. Pham-Huu, N. Keller and M. J. Ledoux, 2002, New carbon nanofiber/graphite felt composite for use as a catalyst support for hydrazine catalytic decomposition, Chemical Communications 9:954—955.
  13. ↑ 13.0 13.1 Xiaowei Chen, et al., 2002, Catalytic Decomposition of Hydrazine over Supported Molybdenum Nitride Catalysts in a Monopropellant Thruster, Catalysis Letters. 79:21–25.

References
ISBN links support NWE through referral fees

  • Parker, Phillip M. 2006. The 2007 Import and Export Market for Organic Derivatives of Hydrazine or Hydroxylamine in United Kingdom. San Diego, CA: ICON Group International, Inc. ISBN 0546028152
  • Schmidt, Eckart Walter. 2001. Hydrazine and its Derivatives : Preparation, Properties, Applications. New York, NY: Wiley-Interscience. ISBN 0471415537
  • Toth, Bela. 2000. Hydrazines and Cancer: A Guidebook on the Carcinogenic Activities of Hydrazines, Related Chemicals, and Hydrazine Containing Natural Products. Amsterdam, NL: Harwood Academic Publishers. ISBN 9057026317

External links

All links retrieved January 22, 2018.

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