1-pentanol

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Structural formula
Structure of 1-pentanol
General
Surname 1-pentanol
other names
  • Pentan-1-ol
  • n -pentanol
  • Amyl alcohol
  • Butyl carbinol
  • Pentyl alcohol
  • AMYL ALCOHOL ( INCI )
Molecular formula C 5 H 12 O
Brief description

colorless liquid

External identifiers / databases
CAS number 71-41-0
EC number 200-752-1
ECHA InfoCard 100,000,684
PubChem 6276
Wikidata Q151733
properties
Molar mass 88.15 g mol −1
Physical state

liquid

density

0.81 g cm −3

Melting point

−78 ° C

boiling point

138 ° C

Vapor pressure
  • 1.3 hPa (20 ° C)
  • 4.8 hPa (30 ° C)
  • 20 hPa (50 ° C)
  • 50 hPa (65 ° C)
solubility

little in water (22 g l −1 at 20 ° C)

Refractive index

1.4101 (20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
02 - Highly / extremely flammable 05 - Corrosive 07 - Warning

danger

H and P phrases H: 226-315-318-332-335
P: 210-302 + 352-305 + 351 + 338
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1-Pentanol is an organic chemical compound and belongs to the group of alcohols . It is one of eight structural isomers of pentanols (called "amyl alcohols").

Extraction and presentation

In the past, amyl alcohols were obtained by distilling fusel oils. Around 1925, the Sharples company developed the chlorination and subsequent hydrolysis of pentane .

Production of 1-pentanol by hydrolysis of 1-chloropentane

Today, 1-pentanol is mainly obtained from 1-butene by oxo synthesis ( hydroformylation and subsequent hydrogenation ) .

properties

1-Pentanol is a colorless liquid with a characteristic odor that only slightly dissolves in water. 1-Pentanol dissolves lithium chloride , which is important for the qualitative detection of lithium .

Thermodynamic properties

According to Antoine, the vapor pressure function results from log 10 (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.68277, B = 1492.549 and C = −91.621 in the temperature range from 307 to 411 K.

Compilation of the most important thermodynamic properties
property Type Value [unit] Remarks
Standard enthalpy of formation Δ f H 0 liquid
Δ f H 0 gas 		−351.62 kJ mol −1
−298 kJ mol −1
Standard entropy S 0 l
S 0 g 		258.9 J mol −1 K −1
401.3 J mol −1 K −1 		as a liquid
as a gas
Enthalpy of combustion Δ c H 0 liquid −3330.91 kJ mol −1
Heat capacity c p 123.1 J mol −1 K −1 (25 ° C)
167.91 J mol −1 K −1 (130.35 ° C) 		as a liquid
as a gas
Enthalpy of fusion Δ f H 0 10.502 kJ mol −1 at the melting point
Entropy of fusion Δ f S 0 53.70 kJ mol −1 at the melting point
Enthalpy of evaporation Δ V H 0 44.36 kJ mol −1 at normal pressure boiling point

The temperature dependence of the enthalpy of vaporization can be calculated according to the equation Δ V H 0 = A e (−αT r ) (1 − T r ) β (Δ V H 0 in kJ / mol, T r = (T / T c ) reduced temperature ) with A = 67.55 kJ / mol, α = −0.8195, β = 0.8272 and T c = 588.2 K in the temperature range between 298 and 421 K.

Safety-related parameters

1-Pentanol is considered a flammable liquid. Flammable vapor-air mixtures can form above the flash point. The compound has a flash point of 42.5 ° C. The explosion range is between 1.3% by volume (47 g / m 3 ) as the lower explosion limit (LEL) and 10.5% by volume (385 g / m 3 ) as the upper explosion limit (UEL). The maximum explosion pressure is 8.4 bar. The limit gap width was determined to be 0.89 mm. This results in an assignment to explosion group IIA. The ignition temperature is 320 ° C. The substance therefore falls into temperature class T2. The ignition temperature decreases with increasing pressure. It is 260 ° C at 3.1 bar, 250 ° C at 4.6 bar and 241 ° C at 10.05 bar.

use

1-pentanol is used as a solvent and for the production of pharmaceuticals, cosmetics, dyes, etc. Flavors used. Because of its antibiotic and antiseptic effects, it is still contained in disinfectants.

toxicity

All pentanols are significantly more toxic than most lower alcohols such as ethanol . Oral doses of 1-pentanol (from about 50 ml) are considered to be potentially lethal for humans. In addition to oral ingestion, damage via the respiratory tract and irritation of the eyes and skin are possible. In animal experiments, 1-pentanol caused kidney dysfunction, breathing difficulties up to pulmonary edema and depressive behavior up to drowsiness in rats and mice .

1-Pentanol was included by the EU in 2015 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of the substance evaluation in the Community's ongoing action plan ( CoRAP ). The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the uptake of 1-pentanol were concerns about consumer use , exposure of workers , high risk characterization ratio (RCR) and widespread use, as well as the possible danger from sensitizing properties. The re-evaluation started in 2016 and was carried out by Lithuania . A final report was then published.

Individual evidence

  1. ↑ Entry on AMYL ALCOHOL in the CosIng database of the EU Commission, accessed on February 25, 2020.
  2. ↑ a b c d e f g h i j k l m n o p q r s t Entry on 1-pentanol in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  3. ↑ a b c d e f Entry on pentanols. In: Römpp Online . Georg Thieme Verlag, accessed on May 15, 2018.
  4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-416.
  5. ↑ Entry on pentan-1-ol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  6. ↑ Production of Isoamyl Alcohol ( Memento from March 12, 2016 in the Internet Archive ): "Pentane chlorination process"
  7. ↑ Richard L. Kenyon, Gordon C. Inskeep, Leslie Gillette, J. Frank Price: Amyl Compounds From Pentane . In: Industrial & Engineering Chemistry . tape 42 , no. 12 , 1950, pp. 2388-2401 , doi : 10.1021 / ie50492a004 .
  8. ^ Wiley-VCH: Ullmann's Fine Chemicals . John Wiley & Sons, 2014, ISBN 978-3-527-68359-8 ( limited preview in Google Book Search).
  9. ↑ a b Science-Online-Lexika: Entry on amyl alcohols in the Lexikon der Chemie. Retrieved February 10, 2009.
  10. ^ HR Kemme, SI Kreps: Vapor pressure of primary n-alkyl chlorides and alcohols . In: Journal of Chemical & Engineering Data . tape 14 , no. 1 , 1969, p. 98-102 , doi : 10.1021 / je60040a011 .
  11. ^ A b C. Mosselman, H. Dekker: Enthalpies of formation of n-alkan-1-ols . In: Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases . tape 71 , 1975, p. 417-424 , doi : 10.1039 / F19757100417 .
  12. ↑ Entry on 1-pentanol . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed July 20, 2012.
  13. ↑ a b c d J. F. Counsel, EB Lees, JF Martin: Thermodynamic properties of organic oxygen compounds. Part XIX. Low-temperature heat capacity and entropy of propan-1-ol, 2-methylpropan-1-ol, and pentan-1-ol . In: Journal of the Chemical Society A: Inorganic, Physical, Theoretical . 1968, p. 1819–1923 , doi : 10.1039 / J19680001819 .
  14. ↑ GC Benson, PJ D'Arcy: Excess isobaric heat capacities of some binary Mixtures: (a C5-alkanol + n-heptane) at 298.15 K . In: The Journal of Chemical Thermodynamics . tape 18 , no. 5 , 1986, pp. 493-498 , doi : 10.1016 / 0021-9614 (86) 90099-6 .
  15. ↑ Erik stromsoe, Hans G. Ronne, Aksel L. Lydersen: Heat capacity of alcohol vapors at atmospheric pressure . In: Journal of Chemical & Engineering Data . tape 15 , no. 2 , 1970, p. 286-290 , doi : 10.1021 / je60045a040 .
  16. ^ A b V. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation. Blackwell Scientific Publications, Oxford 1985, p. 300.
  17. ↑ a b c E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.
  18. ↑ Chemsafe database for safety-related parameters in explosion protection, PTB Braunschweig / BAM Berlin, accessed on December 6, 2018.
  19. ^ National Technical Information Service. Vol. OTS0534716.
  20. ^ RA Scala, EG Burtis: Acute Toxicity of a Homologous Series of Branched-Chain Primary Alcohols . In: American Industrial Hygiene Association Journal . tape 34 , no. 11 , 1973, p. 493-499 , doi : 10.1080 / 0002889738506887 .
  21. ↑ European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report
  22. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): pentan-1-ol , accessed on March 26, 2019.