Isopropyl nitrate: Difference between revisions

| verifiedrevid = 415669035

| Reference=<ref>{{cite book |doi=10.2514/6.1980-1293|chapter=The monopropellant isopropyl nitrate – Its characteristics and uses, and possible future applications |author=A. Abbott |title=16th Joint Propulsion Conference |publisher=American Institute of Aeronautics and Astronautics|year=1980 }}</ref>

| Name = Isopropyl nitrate

| ImageFile = isopropyl nitrate.png

| ImageSize = 150px

| ImageAlt = Skeletal formula of isopropyl nitrate

| ImageFile1 = Isopropyl nitrate 3D ball.png

| ImageSize1 = 170

| ImageAlt1 = Ball-and-stick model of the isopropyl nitrate molecule

| ImageName =

| PIN = Propan-2-yl nitrate

| OtherNames = Isopropyl nitrate<br />Isonite

|Section1={{Chembox Identifiers

| SMILES = CC(C)O[N+](=O)[O-]

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = UPE48E4UJ4

|Section2={{Chembox Properties

| Formula = C₃H₇NO₃

| MolarMass = 105.09 g/mol

| Appearance = Colorless liquid

| Density = 1.036 g/cm³, liquid

| Solubility =

| MeltingPtC = -82.5

| BoilingPtC = 101.5

| pKa = 16.9<ref name=uwisconsin>{{cite web|last1=Reich |first1=Hans |title=Bordwell pKa table: "Nitroalkanes" |url=http://www.chem.wisc.edu/areas/reich/pkatable/ |website=University of Wisconsin Chemistry Department |accessdate=17 January 2016 |url-status=dead |archiveurl=https://web.archive.org/web/20081009060809/http://www.chem.wisc.edu/areas/reich/pkatable/ |archivedate=9 October 2008 }}</ref><ref name=walterjacs>{{cite journal|last1=Matthews|first1=Walter|title=Equilibrium acidities of carbon acids. VI. Establishment of an absolute scale of acidities in dimethyl sulfoxide solution|journal=Journal of the American Chemical Society|date=1975|volume=97|issue=24|page=7006|doi=10.1021/ja00857a010|display-authors=etal}}</ref><ref name=bordwellpka>{{cite journal|last1=Bordwell|first1=F.G.|title=Acidities of carbon acids. VII. Conjugation and strain in some cyclopropyl anions.|journal=Journal of the American Chemical Society|date=1975|volume=97|issue=24|pages=7160–7162|doi=10.1021/ja00857a033}}</ref>

| pKb =

| Viscosity = 0.66 [[Poise (unit)|cP]] at 20 °C

|Section3={{Chembox Structure

| MolShape =

| Coordination =

| CrystalStruct =

| Dipole =

|Section7={{Chembox Hazards

| ExternalSDS = [https://fscimage.fishersci.com/msds/10869.htm External MSDS]

| MainHazards =

| FlashPtC = 22.2

|Section8={{Chembox Related

| OtherAnions =

| OtherCations =

| OtherCompounds =

'''Isopropyl nitrate''' (IPN, 2-propyl nitrate) is a colorless liquid [[monopropellant]]. It is used as a [[Diesel fuel|diesel]] [[cetane number|cetane]] improver. IPN is a low-sensitivity explosive, with a [[Explosive velocity|detonation velocity]] of approximately 5400&nbsp;m/s.<ref>{{Cite web|url=http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/Zhang-131.pdf#search=%22%22isopropyl%20nitrate%22%20IPN%22|title=Shock initiation and detonability of isopropyl nitrate}}</ref>

Isopropyl nitrate is extremely flammable and burns with a practically invisible flame. This presents unique hazards in its handling. The flame is significantly less [[luminous flame|luminous]] than hydrogen or methanol flame and is only visible due to the turbulent hot air it generates.{{cn|date=June 2024}} Nevertheless, it is officially classed as safe to transport provided it is labelled as flammable.<ref>{{cite web | url=http://www.btinternet.com/~javelin/p08_technical_notes/p08_technical_notes.htm | title=Javelin Technical Notes| archive-url=https://web.archive.org/web/20080821165313/http://www.btinternet.com/~javelin/p08_technical_notes/p08_technical_notes.htm| archive-date=2008-08-21}}</ref>

Isopropyl nitrate was previously used in a [[jet engine]] rapid starting system for military interceptor aircraft (a requirement for fast [[Scrambling (military)|scrambling]], as it provided simultaneous, near-instantaneous engine starting for twin engines) and was known as AVPIN.<ref name="R-R, AVPIN">{{Cite book

| title=The Jet Engine

| chapter=11: Starting and Ignition

| publisher=[[Rolls-Royce plc|Rolls-Royce]]

| isbn=978-0-902121-04-1

| year=1986

| ref={{harvid|Rolls-Royce|Jet Engine}}

| pages=124–125

}}</ref> Early systems, as used on the [[Gloster Javelin]], used a simple pressurising cartridge and had a poor reputation for misfires, including engine-destroying explosions. Nevertheless, [[Rolls-Royce Limited|Rolls-Royce]] was able to demonstrate that the fuel is extremely stable and that a [[Shell (projectile)|cannon shell]] could be fired through a container of it with no dramatic effect. Isopropyl nitrate was also sold by the [[Turbonique]] company under the brand name "Thermolene" as a fuel for their line of turbine-powered "drag axles" and superchargers, during the 1960s.

The exhaust fumes from an AVPIN monopropellant engine may themselves be explosive, if mixed with further air. Although engine starters do not require an air supply for their basic operation, air was supplied to later designs, such as that of the [[English Electric Lightning]], by an automatic scavenge pump simply to control these fumes.<ref name="R-R, AVPIN" /> The history of AVPIN use on the Lightning demonstrated it was both safe and effective in use. The reduced availability of AVPIN is now a restriction on the continued operation of some preserved military aircraft, such as Lightnings in the UK and South Africa and some are thus being converted to electric starting.<ref>{{cite web |url=http://boardreader.com/thread/XS458_T5_lightning_video_LAST_EVER_AVPIN_ogvX2e48.html |title=Thread: XS458 T5 lightning – video: LAST EVER AVPIN Started Runway Runs |accessdate=2012-06-07 |url-status=dead |archiveurl=https://web.archive.org/web/20131003135146/http://boardreader.com/thread/XS458_T5_lightning_video_LAST_EVER_AVPIN_ogvX2e48.html |archivedate=2013-10-03 |website=boardreader.com }}</ref><ref>{{cite web | url=http://www.pprune.org/archive/index.php/t-191175.html | title=Hunters & Lightnings |website= PPRuNe Forums}}</ref>

It has also been used as a [[fuel]] for power supply and actuation in guided weapons, notably in the British [[Royal Navy]].<ref>{{cite web|url=http://www.dstan.mod.uk/data/91/089/00000200.pdf |title=Def Stan 91-89 Issue 2|archive-url=https://web.archive.org/web/20071008050028/http://www.dstan.mod.uk/data/91/089/00000200.pdf |archive-date=2007-10-08 }}</ref>

== References ==

== External links ==

* [http://iaspub.epa.gov/srs/srs_proc_qry.navigate?P_SUB_ID=91264 EPA Substance registry system]{{dead link|date=November 2017 |bot=InternetArchiveBot |fix-attempted=yes }}

[[Category:Isopropyl esters]]

[[Category:Monopropellants]]