Difference between revisions of "Isopropyl nitrite"

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| Name = Isopropyl nitrite
 
| Name = Isopropyl nitrite
 
| Reference =  
 
| Reference =  
| IUPACName = 2-propyl nitrite
+
| IUPACName = 2-Propyl nitrite
 
| PIN =  
 
| PIN =  
 
| SystematicName =  
 
| SystematicName =  
Line 50: Line 50:
 
| Appearance = Straw yellow liquid
 
| Appearance = Straw yellow liquid
 
| BoilingPt =  
 
| BoilingPt =  
| BoilingPtC = 41
+
| BoilingPtC = 40
 
| BoilingPt_ref =  
 
| BoilingPt_ref =  
 
| BoilingPt_notes =  
 
| BoilingPt_notes =  
 
| Density = 0.8684 g/cm<sup>3</sup>
 
| Density = 0.8684 g/cm<sup>3</sup>
| Formula = C<sub>3</sub>H<sub>7</sub>NO<sub>2</sub>
+
| Formula = C<sub>3</sub>H<sub>7</sub>NO<sub>2</sub><br>(CH<sub>3</sub>)<sub>2</sub>CHONO
 
| HenryConstant =  
 
| HenryConstant =  
 
| LogP =  
 
| LogP =  
 
| MolarMass = 89.09 g/mol
 
| MolarMass = 89.09 g/mol
 
| MeltingPt =  
 
| MeltingPt =  
| MeltingPtC =  
+
| MeltingPtC = -132
 
| MeltingPt_ref =  
 
| MeltingPt_ref =  
| MeltingPt_notes =  
+
| MeltingPt_notes = <ref>[https://aip.scitation.org/doi/10.1063/1.1731490 R. F. Grant and D. W. Davidson, J. Chem. Phys. 33, 1713 (1960), Dielectric Study of Some Liquid Alkyl Nitrites]</ref>
 
| Odor = Sweet
 
| Odor = Sweet
 
| pKa =  
 
| pKa =  
Line 95: Line 95:
 
| LD50 = 300 mg/kg (mouse, oral)<br>3,200 mg/kg (rabbit, oral)<br>980 mg/kg (rat, oral)<ref>http://www.chemblink.com/MSDS/MSDSFiles/541-42-4_Clear%20Synth.pdf</ref>
 
| LD50 = 300 mg/kg (mouse, oral)<br>3,200 mg/kg (rabbit, oral)<br>980 mg/kg (rat, oral)<ref>http://www.chemblink.com/MSDS/MSDSFiles/541-42-4_Clear%20Synth.pdf</ref>
 
| LC50 =  
 
| LC50 =  
| MainHazards = Flammable
+
| MainHazards = Flammable<br>Psychoactive
 
| NFPA-F =  
 
| NFPA-F =  
 
| NFPA-H =  
 
| NFPA-H =  
Line 106: Line 106:
 
| OtherFunction =  
 
| OtherFunction =  
 
| OtherFunction_label =  
 
| OtherFunction_label =  
| OtherCompounds =  
+
| OtherCompounds = [[Ethyl nitrite]]<br>[[Isobutyl nitrite]]
 
   }}
 
   }}
 
}}
 
}}
'''Isopropyl nitrite''' is a highly flammable organic ester.
+
'''Isopropyl nitrite''' is a highly flammable organic ester. It has the general formula '''(CH<sub>3</sub>)<sub>2</sub>CHONO'''.
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
Isopropyl nitrite reacts with [[hydrazine hydrate]] and [[sodium hydroxide]] to form [[sodium azide]]. 
+
Isopropyl nitrite reacts with [[hydrazine]] hydrate and [[sodium hydroxide]] to form [[sodium azide]]. 
  
 
===Physical===
 
===Physical===
Isopropyl nitrite is straw yellow colour and has a sweet, pleasant smell. It is immiscible and less dense than water.
+
Isopropyl nitrite is straw yellow color and has a sweet, pleasant smell. It is immiscible and less dense than water.
Isopropyl nitrite has a very high vapour pressure and a low boiling point, although it will decompose on boiling to produce [[Nitrogen dioxide|nitrogen oxides]] and [[isopropanol]]. A low flash point combined with the high vapour pressure means it is very easy to ignite.
+
Isopropyl nitrite has a very high vapor pressure and a low boiling point, although it will decompose on boiling to produce [[Nitrogen dioxide|nitrogen oxides]] and [[isopropanol]]. A low flash point combined with the high vapor pressure means it is very easy to ignite.
  
 
==Availability==
 
==Availability==
Isopropyl nitrite is not readily available, and is better made in a home lab setting. 
+
Isopropyl nitrite was available as the main active ingredient in some types of "poppers" (along with amyl nitrite), but it's harder to get hold of in recent years. In some countries, the sale of amyl nitrites may be be restricted or illegal.
 +
 
 +
It's better made in a home lab setting. 
  
 
==Preparation==
 
==Preparation==
Concentrated [[hydrochloric acid]] is slowly dripped onto [[sodium nitrite]] suspended in [[isopropanol]], generating [[nitrous acid]] which reacts with the alcohol. The concentration of isopropanol should be less than 100% to ensure the solution does not get too acidic (which will rapidly decompose the ester) and that some of the precipitate byproducts dissolve. Diluted [[sulfuric acid]] can also be used but this will result in a larger amount of precipitate due to [[sodium sulfate]]'s lower solubility compared to [[sodium chloride]].
+
Concentrated [[hydrochloric acid]] is slowly dripped onto [[sodium nitrite]] suspended in [[isopropanol]], generating [[nitrous acid]] which reacts with the alcohol. The concentration of isopropanol should be less than 100% to ensure the solution does not get too acidic (which will rapidly decompose the ester) and that some of the precipitate byproducts dissolve. Diluted [[sulfuric acid]] can also be used but this will result in a larger amount of precipitate due to [[sodium sulfate]]'s lower solubility compared to [[sodium chloride]].<ref>https://www.youtube.com/watch?v=bbmpmLjfkkM</ref><ref>https://www.youtube.com/watch?v=ipqSn0nnZBU</ref>
  
 
Every reagent should be as cold as possible to limit decomposition to nitrogen oxides. An ice bath may be needed.
 
Every reagent should be as cold as possible to limit decomposition to nitrogen oxides. An ice bath may be needed.
 +
 +
To limit exposure to this compound, the reaction is often conducted in a [[separatory funnel]], which can be easily closed to limit vapors, and is also a convenient way of removing the aqueous layer.
  
 
==Projects==
 
==Projects==
*Make sodium azide
+
*Make [[sodium azide]]
 
*Antidote for [[hydrogen sulfide]] and cyanide poisonings
 
*Antidote for [[hydrogen sulfide]] and cyanide poisonings
  
 
==Handling==
 
==Handling==
 
===Safety===
 
===Safety===
As well as being highly flammable, being an organic nitrite it promotes vascodilation in the body, pushing more blood to the brain. Hence breathing fumes of isopropyl nitrite can have some mild strange side effects that mostly end up in a headache. Proper ventaliation is required when using this compound. 
+
As well as being highly flammable, being an organic nitrite it promotes vasodilation in the body, pushing more blood to the brain. Hence breathing fumes of isopropyl nitrite can have some mild strange side effects that mostly end up in a headache. Proper ventilation is required when using this compound. 
  
In case of nitrite poisoning, small dosages of methylene blue are recommended (0.1 ml of 1% solution per kilogram of patient's weight, intravenously). Not to be confused with large dosages, which are toxic in the same way nitrites are, and are used to treat poisoning with blood agents like cyanides, [[carbon monoxide]] and [[hydrogen sulfide]] (isopropyl nitrite itself can work as an antidote in these cases).
+
In case of nitrite poisoning, small dosages of [[methylene blue]] are recommended (0.1 ml of 1% solution per kilogram of patient's weight, intravenously). Not to be confused with large dosages, which are toxic in the same way nitrites are, and are used to treat poisoning with blood agents like cyanides, [[carbon monoxide]] and [[hydrogen sulfide]] (isopropyl nitrite itself can work as an antidote in these cases).
  
 
===Storage===
 
===Storage===
 
Storage is best done in a cold place such as a fridge or freezer, but care must be taken to prevent as the vapors travel quickly and can easily find a source of ignition. 
 
Storage is best done in a cold place such as a fridge or freezer, but care must be taken to prevent as the vapors travel quickly and can easily find a source of ignition. 
  
If care is taken to make sure the ester does not contain any acid before storage, it will not quickly decompose and may be stored cold for many months. 
+
If care is taken to make sure the ester does not contain any acid before storage, it will not quickly decompose and may be stored cold for many months. Anhydrous [[calcium chloride]] is often added to keep the compound dry, as prolonged exposure to water may cause hydrolysis.
  
 
===Disposal===
 
===Disposal===
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[[Category:Nitrites]]
 
[[Category:Nitrites]]
 
[[Category:Alkyl nitrites]]
 
[[Category:Alkyl nitrites]]
 +
[[Category:Volatile chemicals]]
 
[[Category:Esters of inorganic acids]]
 
[[Category:Esters of inorganic acids]]
 
[[Category:Psychoactive substances]]
 
[[Category:Psychoactive substances]]
 
[[Category:Liquids]]
 
[[Category:Liquids]]

Latest revision as of 16:15, 6 February 2022

Isopropyl nitrite
Isopropyl nitrite separatory funnel by Doug's Lab.png
Freshly prepared isopropyl nitrite
Names
IUPAC name
2-Propyl nitrite
Other names
1-Methylethyl nitrite
Isopropyl alcohol nitrite
Nitrous acid, isopropyl ester
Properties
C3H7NO2
(CH3)2CHONO
Molar mass 89.09 g/mol
Appearance Straw yellow liquid
Odor Sweet
Density 0.8684 g/cm3
Melting point −132 °C (−206 °F; 141 K) [1]
Boiling point 40 °C (104 °F; 313 K)
Insoluble
Solubility Miscible with acetone, diethyl ether, ethanol
Hazards
Safety data sheet Sigma-Aldrich
Flash point -29 °C (-20.2 °F; 244 K)
Lethal dose or concentration (LD, LC):
300 mg/kg (mouse, oral)
3,200 mg/kg (rabbit, oral)
980 mg/kg (rat, oral)[2]
Related compounds
Related compounds
Ethyl nitrite
Isobutyl nitrite
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Isopropyl nitrite is a highly flammable organic ester. It has the general formula (CH3)2CHONO.

Properties

Chemical

Isopropyl nitrite reacts with hydrazine hydrate and sodium hydroxide to form sodium azide

Physical

Isopropyl nitrite is straw yellow color and has a sweet, pleasant smell. It is immiscible and less dense than water. Isopropyl nitrite has a very high vapor pressure and a low boiling point, although it will decompose on boiling to produce nitrogen oxides and isopropanol. A low flash point combined with the high vapor pressure means it is very easy to ignite.

Availability

Isopropyl nitrite was available as the main active ingredient in some types of "poppers" (along with amyl nitrite), but it's harder to get hold of in recent years. In some countries, the sale of amyl nitrites may be be restricted or illegal.

It's better made in a home lab setting. 

Preparation

Concentrated hydrochloric acid is slowly dripped onto sodium nitrite suspended in isopropanol, generating nitrous acid which reacts with the alcohol. The concentration of isopropanol should be less than 100% to ensure the solution does not get too acidic (which will rapidly decompose the ester) and that some of the precipitate byproducts dissolve. Diluted sulfuric acid can also be used but this will result in a larger amount of precipitate due to sodium sulfate's lower solubility compared to sodium chloride.[3][4]

Every reagent should be as cold as possible to limit decomposition to nitrogen oxides. An ice bath may be needed.

To limit exposure to this compound, the reaction is often conducted in a separatory funnel, which can be easily closed to limit vapors, and is also a convenient way of removing the aqueous layer.

Projects

Handling

Safety

As well as being highly flammable, being an organic nitrite it promotes vasodilation in the body, pushing more blood to the brain. Hence breathing fumes of isopropyl nitrite can have some mild strange side effects that mostly end up in a headache. Proper ventilation is required when using this compound. 

In case of nitrite poisoning, small dosages of methylene blue are recommended (0.1 ml of 1% solution per kilogram of patient's weight, intravenously). Not to be confused with large dosages, which are toxic in the same way nitrites are, and are used to treat poisoning with blood agents like cyanides, carbon monoxide and hydrogen sulfide (isopropyl nitrite itself can work as an antidote in these cases).

Storage

Storage is best done in a cold place such as a fridge or freezer, but care must be taken to prevent as the vapors travel quickly and can easily find a source of ignition. 

If care is taken to make sure the ester does not contain any acid before storage, it will not quickly decompose and may be stored cold for many months. Anhydrous calcium chloride is often added to keep the compound dry, as prolonged exposure to water may cause hydrolysis.

Disposal

Acid hydrolysis of the compound destroys it quickly, with the evolution of nitrogen oxides. It is recommended to either burn it or simply let it evaporate over pouring it down a sink, as its solvent properties may adversely affect a plumbing system. 

References

  1. R. F. Grant and D. W. Davidson, J. Chem. Phys. 33, 1713 (1960), Dielectric Study of Some Liquid Alkyl Nitrites
  2. http://www.chemblink.com/MSDS/MSDSFiles/541-42-4_Clear%20Synth.pdf
  3. https://www.youtube.com/watch?v=bbmpmLjfkkM
  4. https://www.youtube.com/watch?v=ipqSn0nnZBU

Relevant Sciencemadness threads