Difference between revisions of "Propan-1-ol"

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(Imported from http://en.wikipedia.org/w/index.php?title=Propan-1-ol&oldid=306580204)
 
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|  OtherNames = 1-propanol<br />propyl alcohol<br />''n''-propanol<br />''n''-propyl alcohol<br />propanol
 
|  OtherNames = 1-propanol<br />propyl alcohol<br />''n''-propanol<br />''n''-propyl alcohol<br />propanol
 
| Section1 = {{Chembox Identifiers
 
| Section1 = {{Chembox Identifiers
−
|  SMILES = CCCO
+
|  InChI = 1/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
 +
|  StdInChI = 1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
 +
|  InChIKey = BDERNNFJNOPAEC-UHFFFAOYAO
 +
|  StdInChIKey = BDERNNFJNOPAEC-UHFFFAOYSA-N
 
|  CASNo = 71-23-8
 
|  CASNo = 71-23-8
 
|    CASNo_Ref = {{cascite}}
 
|    CASNo_Ref = {{cascite}}
 +
|  EC-number = 200-746-9
 
|  ChemSpiderID = 1004
 
|  ChemSpiderID = 1004
 
|  RTECS = UH8225000
 
|  RTECS = UH8225000
 +
|  SMILES = CCCO
 
   }}
 
   }}
 
| Section2 = {{Chembox Properties
 
| Section2 = {{Chembox Properties
 +
|  Reference = <ref name="ICSC">{{ICSC-ref|05|53|name=1-Propanol|date=October 1999}}.</ref>
 
|  Formula = C<sub>3</sub>H<sub>8</sub>O
 
|  Formula = C<sub>3</sub>H<sub>8</sub>O
−
|  MolarMass = 60.10 g/mol
+
|  MolarMass = 60.095 g/mol
−
|  Appearance = Clear, colourless liquid
+
|  Appearance = colourless liquid
 
|  Density = 0.8034 g/cm<sup>3</sup>, liquid
 
|  Density = 0.8034 g/cm<sup>3</sup>, liquid
−
|  Solubility = Fully [[miscible]]
+
|  Solubility = miscible
 
|  MeltingPt = −126.5 °C (146.7 K)
 
|  MeltingPt = −126.5 °C (146.7 K)
 
|  BoilingPt = 97.1 °C (370.3 K)
 
|  BoilingPt = 97.1 °C (370.3 K)
−
|  Heat Capacity = 1.386 kJ&thinsp;K<sup>&minus;1</sup>&thinsp;kg<sup>&minus;1</sup> (288.15 K, 1 atm)
+
|  pKa = ~16
−
|  pKa = (~16)
+
|  Viscosity = 1.938 cP at 25°C
−
|  Viscosity = 1.938 [[Poise|cP]] at 25°C
+
|  Dipole = 1.68 D
 +
|  LogP = 0.25
 +
|  VaporPressure = 2.0 kPa (20 ºC)
 
   }}
 
   }}
−
| Section3 = {{Chembox Structure
+
| Section3 = {{Chembox Thermochemistry
−
|  Dipole = 1.68 [[Debye|D]]
+
|  Heat Capacity = 1386 J&thinsp;K<sup>&minus;1</sup>&thinsp;kg<sup>&minus;1</sup>
 
   }}
 
   }}
 
| Section7 = {{Chembox Hazards
 
| Section7 = {{Chembox Hazards
−
|  ExternalMSDS =
+
|  Reference = <ref name="ICSC"/><ref>{{CLP Regulation|index=603-003-00-0|page=477}}</ref><ref>{{PGCH|0533|name=n-Propyl alcohol}}.</ref>
−
|   EUClass = Flammable ('''F''')<br />Irritant ('''Xi''')
+
|  ExternalMSDS = {{ICSC-small|05|53}}
−
|   NFPA-H = 1
+
|  EUIndex = 603-003-00-0
−
|  NFPA-F = 3
+
|  GHSPictograms = {{GHS02|Flam. Liq. 2}}{{GHS05|Eye Dam. 1}}{{GHS07|STOT SE 3}}
−
|  NFPA-R =
+
|  GHSSignalWord = DANGER
−
|  RPhrases = {{R11}}, {{R41}}, {{R67}}
+
|  HPhrases = {{H-phrases|225|318|336}}
−
|  SPhrases = {{S2}}, {{S7}}, {{S16}}, {{S24}},<br />{{S26}}, {{S39}}
+
|  FlashPt = 15 °C (59 ºF)
−
|  FlashPt = 15 °C
+
|   Autoignition = 371 ºC (700 ºF)
−
   }}<!--
+
|  ExploLimits = 2.1–13.5%
−
 
+
|   PEL = 200 ppm TWA
−
 
+
|   IDLH = 800 ppm
−
| [[Propan-1-ol chemdata supplement#Structure and properties|Structure and<br />properties]]
+
  }}
−
 
 
−
| [[Propan-1-ol chemdata supplement#Thermodynamic properties|Thermodynamic<br />data]]
 
−
 
 
−
 
 
−
-->
 
 
| Section8 = {{Chembox Related
 
| Section8 = {{Chembox Related
−
|  Function = [[alcohol]]s
+
|  OtherFunctn = [[Ethanol]]<br/>[[Isopropanol]]<br/>[[Butan-1-ol]]
−
|  OtherFunctn = [[Ethanol]]<br />[[Isopropyl alcohol|Propan-2-ol]]<br />[[Butan-1-ol]]
+
|    Function = [[alcohol]]s
−
|  OtherCpds = [[Propionaldehyde]]<br />[[Propionic acid]]<br />[[1-Chloropropane]]<br />[[Propyl acetate]]
+
|  OtherCpds = [[Propionaldehyde]]<br/>[[Propionic acid]]<br/>[[1-Chloropropane]]<br/>[[Propyl acetate]]
 
   }}
 
   }}
 
}}
 
}}
  
−
'''Propan-1-ol''' is a primary [[alcohol]] with the Molecular formula of C<sub>3</sub>H<sub>8</sub>O<sub></sub>.  It is also known as '''1-propanol''', '''1-propyl alcohol''', '''n-propyl alcohol''', or simply '''propanol'''. It is an [[isomer]] of [[propan-2-ol]]. It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters.  It is formed naturally in small amounts during many fermentation processes.
+
'''Propan-1-ol''' is a primary [[alcohol]] with the Molecular formula of C<sub>3</sub>H<sub>8</sub>O<sub></sub>.  It is also known as '''1-propanol''', '''1-propyl alcohol''', '''''n''-propyl alcohol''', or simply '''propanol'''. It is an [[isomer]] of [[propan-2-ol]]. It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters.  It is formed naturally in small amounts during many fermentation processes.
  
 
==Chemical properties==
 
==Chemical properties==
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1-Propanol is manufactured by catalytic [[hydrogenation]] of [[propionaldehyde]].  The propionaldehyde is itself produced via the [[oxo process]], by [[hydroformylation]] of [[ethylene]] using [[carbon monoxide]] and [[hydrogen]] in the presence of a catalyst such as [[dicobalt octacarbonyl|cobalt octacarbonyl]] or a [[rhodium]] complex.
 
1-Propanol is manufactured by catalytic [[hydrogenation]] of [[propionaldehyde]].  The propionaldehyde is itself produced via the [[oxo process]], by [[hydroformylation]] of [[ethylene]] using [[carbon monoxide]] and [[hydrogen]] in the presence of a catalyst such as [[dicobalt octacarbonyl|cobalt octacarbonyl]] or a [[rhodium]] complex.
  
−
:(1) [[Ethylene|H<sub>2</sub>C=CH<sub>2</sub>]]  + [[Carbon monoxide|CO]]  + [[Hydrogen|H<sub>2</sub>]]  →  [[Propionaldehyde|CH<sub>3</sub>CH<sub>2</sub>CH=O]]
+
:(1) H<sub>2</sub>C=CH<sub>2</sub> + CO + H<sub>2</sub> →  CH<sub>3</sub>CH<sub>2</sub>CH=O
−
 
 
 
:(2) CH<sub>3</sub>CH<sub>2</sub>CH=O  +  H<sub>2</sub>  →  CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH
 
:(2) CH<sub>3</sub>CH<sub>2</sub>CH=O  +  H<sub>2</sub>  →  CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH
  
−
A traditional laboratory preparation of 1-propanol involves treating [[N-Propyl iodide|''n''-propyl iodide]] with moist [[silver(I) oxide|Ag<sub>2</sub>O]].
+
A traditional laboratory preparation of 1-propanol involves treating [[1-Iodopropane|''n''-propyl iodide]] with moist [[silver(I) oxide|Ag<sub>2</sub>O]].
  
 
==History==
 
==History==
−
1-Propanol was discovered in [[1853]] by Chancel, who obtained it by [[fractional distillation]] of [[fusel oil]].
+
Propan-1-ol was discovered in 1853 by Chancel, who obtained it by [[fractional distillation]] of [[fusel oil]].
  
 
==References==
 
==References==
 
{{reflist}}
 
{{reflist}}
−
# {{vogelOrganic}}
+
 
−
# {{Cite book
+
==Further reading==
−
| edition = 87
+
*{{VogelOrganic5th}}
−
| publisher = TF-CRC
+
*{{RubberBible87th}}
−
| isbn = 0849304873
+
*{{Merck14th}}
−
| editor-last = Lide
+
*{{Citation | last1 = Perkin | first1 = W. H. | last2 = Kipping | first2 = F. S | title = Organic Chemistry | publisher = W. & R. Chambers | location = London | year = 1922}}
−
| editor-first = David R.
+
 
−
| title = CRC Handbook of Chemistry and Physics, 87th Edition
 
−
| date = 2006-06-26
 
−
}}
 
−
# {{Cite book
 
−
| edition = 14
 
−
| publisher = Merck
 
−
| isbn = 091191000X
 
−
| editor= Maryadele J. O'Neil
 
−
| title = The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals
 
−
| date = 2006-11-03
 
−
}}
 
−
# {{Cite book
 
−
|title=Organic Chemistry
 
−
|publisher=W. & R. Chambers
 
−
|year=1922
 
−
|last1=Perkin
 
−
|first1=W. H.
 
−
|last2=Kipping
 
−
|first2=F. S
 
−
|location=London
 
−
}}
 
 
==External links==
 
==External links==
−
*[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc05/icsc0553.htm International Chemical Safety Card 0553]
+
*{{ICSC|05|53}}
−
*[http://www.cdc.gov/niosh/npg/npgd0533.html NIOSH Pocket Guide to Chemical Hazards]
+
*{{PGCH|0533}}
  
−
{{Alcohols}}
 
 
{{Antiseptics and disinfectants}}
 
{{Antiseptics and disinfectants}}
  
 +
{{DEFAULTSORT:Propanol-1}}
 
[[Category:Alcohols]]
 
[[Category:Alcohols]]
  
 
{{Imported from Wikipedia|name=Propan-1-ol|id=306580204}}
 
{{Imported from Wikipedia|name=Propan-1-ol|id=306580204}}

Revision as of 09:30, 22 August 2009

Propanol
Propan-1-ol
Propan-1-ol-2D-flat.png
Propan-1-ol-3D-balls.png
IUPAC name propan-1-ol
Other names 1-propanol
propyl alcohol
n-propanol
n-propyl alcohol
propanol
Identifiers
InChI InChI=1/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
InChIKey BDERNNFJNOPAEC-UHFFFAOYAO
Standard InChI InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
Standard InChIKey BDERNNFJNOPAEC-UHFFFAOYSA-N
CAS number [71-23-8]
EC number 200-746-9
RTECS UH8225000
ChemSpider 1004
SMILES
Properties[1]
Chemical formula C3H8O
Molar mass 60.095 g/mol
Appearance colourless liquid
Density 0.8034 g/cm3, liquid
Melting point

−126.5 °C (146.7 K)

Boiling point

97.1 °C (370.3 K)

Solubility in water miscible
log P 0.25
Vapor pressure 2.0 kPa (20 ºC)
Acidity (pKa) ~16
Viscosity 1.938 cP at 25°C
Dipole moment 1.68 D
Thermochemistry
Hazards[1][2][3]
Material safety data sheet (MSDS) ICSC 0553
EU index number 603-003-00-0
GHS pictograms Flam. Liq. 2Eye Dam. 1STOT SE 3
GHS signal word DANGER
GHS hazard statements H225, H318, H336
Flash point 15 °C (59 ºF)
Autoignition temp. 371 ºC (700 ºF)
Explosive limits 2.1–13.5%
PEL (U.S.) 200 ppm TWA
IDLH level 800 ppm
Related compounds
Other alcohols Ethanol
Isopropanol
Butan-1-ol
Other compounds Propionaldehyde
Propionic acid
1-Chloropropane
Propyl acetate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Propan-1-ol is a primary alcohol with the Molecular formula of C3H8O. It is also known as 1-propanol, 1-propyl alcohol, n-propyl alcohol, or simply propanol. It is an isomer of propan-2-ol. It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters. It is formed naturally in small amounts during many fermentation processes.

Chemical properties

1-Propanol shows the normal reactions of a primary alcohol. Thus it can be converted to alkyl halides; for example red phosphorus and iodine produce n-propyl iodide in 90% yield, while PCl3 with catalytic ZnCl2 gives 1-chloropropane. Reaction with acetic acid in the presence of an H2SO4 catalyst under Fischer esterification conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with Na2Cr2O7 and H2SO4 gives only a 36% yield of propionaldehyde, and therefore for this type of reaction higher yielding methods using PCC or the Swern oxidation are recommended. Oxidation with chromic acid yields propionic acid

Some example reactions of 1-propanol


Preparation

1-Propanol is a major constituent of fusel oil, a by-product formed from certain amino acids when potatoes or grains are fermented to produce ethanol. This is no longer a significant source of propanol.

1-Propanol is manufactured by catalytic hydrogenation of propionaldehyde. The propionaldehyde is itself produced via the oxo process, by hydroformylation of ethylene using carbon monoxide and hydrogen in the presence of a catalyst such as cobalt octacarbonyl or a rhodium complex.

(1) H2C=CH2 + CO + H2 → CH3CH2CH=O
(2) CH3CH2CH=O + H2 → CH3CH2CH2OH

A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide with moist Ag2O.

History

Propan-1-ol was discovered in 1853 by Chancel, who obtained it by fractional distillation of fusel oil.

References

  1. ↑ 1.0 1.1 1-Propanol; International Chemical Safety Card 0553; International Labour Organization: Geneva, October 1999, <http://www.inchem.org/documents/icsc/icsc/eics0553.htm>.
  2. ↑ Index no. 603-003-00-0 of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006. OJEU L353, 31.12.2008, pp 1–1355 at p 477.
  3. ↑ n-Propyl alcohol, NIOSH Pocket Guide to Chemical Hazards.

Further reading

  • Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman: Harlow, 1989. ISBN 0-582-46236-3
  • CRC Handbook of Chemistry and Physics, 87th ed.; Lide, David R., Ed.; CRC Press: Boca Raton, FL, 2006. ISBN 0-8493-0487-3
  • The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 14th ed.; O'Neil, Maryadele J., Ed.; Merck, 2006. ISBN 091191000X
  • Perkin, W. H.; Kipping, F. S Organic Chemistry; W. & R. Chambers: London, 1922

External links

Template:Antiseptics and disinfectants

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