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{{DISPLAYTITLE:Di-''n''-propyl ether}}
{{Chembox
{{Chembox
| ImageFile = Dipropylether.png
| ImageFile = Di-n-propylether Structural Formulae.svg
| Name = Di-''n''-propyl ether
| ImageSize = 200px
| IUPACName = 1-Propoxypropane
| PIN = 1-Propoxypropane
| OtherNames = propyl ether<br />dipropyl ether<br />Di-''n''-propyl ether
| OtherNames = Propyl ether, di-<br />Dipropyl ether, normal isomer<br />Di-''n''-propyl ether
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| CASNo = 111-43-3
| CASNo = 111-43-3
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 8114
| UNII = 42Q250HS4G
⚫
| ChemSpiderID = 7823
| SMILES = O(CCC)CCC
| PubChem = 8114
⚫
| ChemSpiderID = 7823
⚫
| InChI = 1/C6H14O/c1-3-5-7-6-4-2/h3-6H2,1-2H3
| SMILES = O(CCC)CCC
⚫
| InChIKey = POLCUAVZOMRGSN-UHFFFAOYAT
| StdInChI = 1S/C6H14O/c1-3-5-7-6-4-2/h3-6H2,1-2H3
| InChI = 1/C6H14O/c1-3-5-7-6-4-2/h3-6H2,1-2H3
| StdInChIKey = POLCUAVZOMRGSN-UHFFFAOYSA-N
| InChIKey = POLCUAVZOMRGSN-UHFFFAOYAT
⚫
| StdInChI = 1S/C6H14O/c1-3-5-7-6-4-2/h3-6H2,1-2H3
⚫
| StdInChIKey = POLCUAVZOMRGSN-UHFFFAOYSA-N
}}
}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| C=6|H=14|O=1
| C=6 | H=14 | O=1
| Appearance = Colorless liquid
| Appearance = Colorless liquid
| Density = 0.75 g/cm<sup>3</sup><ref name=GESTIS>{{GESTIS|ZVG=510206}}</ref>
| Density = 0.75 g/cm<sup>3</sup><ref name=GESTIS>{{GESTIS|ZVG=510206}}</ref>
| MeltingPtC = -122
| MeltingPtC = -122
| Melting_notes = <ref name=GESTIS/>
| MeltingPt_ref = <ref name=GESTIS/>
| BoilingPtC = 90
| BoilingPtC = 90
| Boiling_notes = <ref name=GESTIS/>
| BoilingPt_ref = <ref name=GESTIS/>
| Solubility = 3 g/L (20 °C)
| Solubility = 3 g/L (20 °C)
}}
}}
| Section3 = {{Chembox Hazards
| Section3 = {{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPtC =-18
| FlashPt = {{convert|-18|C|F}}<ref name=GESTIS/>
| FlashPt_ref = <ref name=GESTIS/>
| Autoignition =
| AutoignitionPt =
| NFPA-H = 1
| NFPA-F = 3
| NFPA-R = 1
}}
}}
}}
}}


'''Dipropyl ether''' is the symmetrical [[ether]] of two ''n''-[[propyl]] groups. It is a colorless, [[flammable liquid]] with a sweet odor typical of ethers.
⚫
'''Dipropyl ether''' is an [[ether]] of two ''n''-[[propyl]] groups. It can be synthesized by reacting two molecules of [[propan-1-ol]] in the presence of [[4-methylbenezesulfonic acid]], in the same way other symmetrical ethers are formed.<ref>{{Cite book| title = Merck Index of Chemicals and Drugs, 14th ed| year = 2006| isbn=978-0-911910-00-1| editor = O'Neil, Maryadele; Heckelman, Patricia; Koch, Cherie; Roman, Kristin| publisher = Merck Research Laboratories}}</ref>

==Preparation==

===Acid catalyzed ether synthesis===

⚫
Dipropyl ether can be synthesized by reacting two molecules of [[1-Propanol|''n''-propanol]] in the presence of [[p-toluenesulfonic acid]] (a strong acid) and heat, in the same way other symmetrical ethers may be formed.<ref name="merck">{{Cite book| title = Merck Index of Chemicals and Drugs | edition = 14th | year = 2006| isbn=978-0-911910-00-1|editor1=O'Neil, Maryadele |editor2=Heckelman, Patricia |editor3=Koch, Cherie |editor4=Roman, Kristin | publisher = Merck Research Laboratories}}</ref>

===Williamson ether synthesis===

This ether may also be prepared by way of the [[Williamson ether synthesis]] in which ''n''-propoxide, the conjugate base of ''n''-propanol, is reacted with an ''n''-propyl halide:<ref>{{Cite book| title = Organic Chemistry, 3rd ed.| year = 2004| isbn=978-0763735869|author1=Fox, Marye |author2=Whitesell, James | publisher = Jones & Bartlett Publishers}}</ref>

:[[File:Williamson ether synthesis of dipropyl ether.png|600px|Williamson ether synthesis of dipropyl ether.]]

==Safety==

As is typical of ethers, dipropyl ether may slowly form explosive [[organic peroxide]]s over long periods in storage.<ref name="merck" /> Antioxidants such as [[butylated hydroxytoluene]] are often added to ethers to prevent this process.<ref>{{cite web | url = http://www.sigmaaldrich.com/catalog/product/sial/296082?lang=en&region=US | title = Diethyl ether product listing | publisher = [[Sigma-Aldrich]] | accessdate = 2012-07-03}}</ref>

Due to the shock and light sensitive nature of organic peroxides, dipropyl ether should never be boiled or evaporated to dryness. This concentrates peroxides that may be present, which can then detonate unexpectedly destroying the vessel in which they have deposited or igniting nearby flammable liquids.<ref>{{cite web | url = http://www.ccohs.ca/oshanswers/chemicals/organic/organic_peroxide.html#_1_2 | title = Organic peroxide hazards | publisher = [[Canadian Centre for Occupational Health and Safety]] | accessdate = 2012-07-03}}</ref>


==See also==
==See also==
Line 40: Line 65:
{{reflist}}
{{reflist}}


[[Category:Dialkyl ethers]]

[[Category:Ethers]]
[[Category:Symmetrical ethers]]
[[Category:Sweet-smelling chemicals]]

{{Organic-compound-stub}}

[[de:Dipropylether]]
[[fr:Propoxypropane]]
[[nl:Dipropylether]]
[[pt:Éter dipropílico]]

Latest revision as of 16:36, 4 November 2021

Di-n-propyl ether
Names
Preferred IUPAC name
1-Propoxypropane
Other names
Propyl ether, di-
Dipropyl ether, normal isomer
Di-n-propyl ether
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.518 Edit this at Wikidata
UNII
  • InChI=1S/C6H14O/c1-3-5-7-6-4-2/h3-6H2,1-2H3
    Key: POLCUAVZOMRGSN-UHFFFAOYSA-N
  • InChI=1/C6H14O/c1-3-5-7-6-4-2/h3-6H2,1-2H3
    Key: POLCUAVZOMRGSN-UHFFFAOYAT
  • O(CCC)CCC
Properties
C6H14O
Molar mass 102.177 g·mol−1
Appearance Colorless liquid
Density 0.75 g/cm3[1]
Melting point −122 °C (−188 °F; 151 K)[1]
Boiling point 90 °C (194 °F; 363 K)[1]
3 g/L (20 °C)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
3
1
Flash point −18 °C (0 °F; 255 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dipropyl ether is the symmetrical ether of two n-propyl groups. It is a colorless, flammable liquid with a sweet odor typical of ethers.

Preparation

[edit]

Acid catalyzed ether synthesis

[edit]

Dipropyl ether can be synthesized by reacting two molecules of n-propanol in the presence of p-toluenesulfonic acid (a strong acid) and heat, in the same way other symmetrical ethers may be formed.[2]

Williamson ether synthesis

[edit]

This ether may also be prepared by way of the Williamson ether synthesis in which n-propoxide, the conjugate base of n-propanol, is reacted with an n-propyl halide:[3]

Williamson ether synthesis of dipropyl ether.

Safety

[edit]

As is typical of ethers, dipropyl ether may slowly form explosive organic peroxides over long periods in storage.[2] Antioxidants such as butylated hydroxytoluene are often added to ethers to prevent this process.[4]

Due to the shock and light sensitive nature of organic peroxides, dipropyl ether should never be boiled or evaporated to dryness. This concentrates peroxides that may be present, which can then detonate unexpectedly destroying the vessel in which they have deposited or igniting nearby flammable liquids.[5]

See also

[edit]

References

[edit]
  1. ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b O'Neil, Maryadele; Heckelman, Patricia; Koch, Cherie; Roman, Kristin, eds. (2006). Merck Index of Chemicals and Drugs (14th ed.). Merck Research Laboratories. ISBN 978-0-911910-00-1.
  3. ^ Fox, Marye; Whitesell, James (2004). Organic Chemistry, 3rd ed. Jones & Bartlett Publishers. ISBN 978-0763735869.
  4. ^ "Diethyl ether product listing". Sigma-Aldrich. Retrieved 2012-07-03.
  5. ^ "Organic peroxide hazards". Canadian Centre for Occupational Health and Safety. Retrieved 2012-07-03.
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