1,5-pentanediol

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Structural formula
Structural formula of 1,5-pentanediol
General
Surname 1,5-pentanediol
other names
  • Pentane-1,5-diol
  • 1,5-dihydroxypentane
  • Pentamethylene glycol
  • 1,5-PENTANEDIOL ( INCI )
Molecular formula C 5 H 12 O 2
Brief description

colorless, viscous liquid

External identifiers / databases
CAS number 111-29-5
EC number 203-854-4
ECHA InfoCard 100.003.505
PubChem 8105
Wikidata Q161557
properties
Molar mass 104.15 g mol −1
Physical state

liquid

density

0.99 g cm −3 (20 ° C)

Melting point

−16 ° C

boiling point

242 ° C

Vapor pressure

1 Pa (20 ° C)

solubility

miscible with water

Refractive index

1.4499

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
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

1,5-Pentanediol is a chemical compound from the group of alkanediols . It consists of the basic structure of n -pentane , at the terminal positions of which there are hydroxyl groups .

Extraction and presentation

Technically, 1,5-pentanediol can be obtained by hydrogenolysis of tetrahydrofurfuryl alcohol at temperatures of 250-300 ° C. and pressures of 230-430 bar over Adkins catalysts based on spinel copper chromite .

Hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol in the presence of an Adkins catalyst based on copper chromite

In addition, the compound can be obtained by catalytic hydrogenation of glutaric acid , glutaraldehyde or glutaric acid esters.

Another synthetic route is the hydrogenation of furfural with molecular hydrogen and iron (II) chloride on a platinum catalyst .

properties

1,5-pentanediol is a colorless liquid that boils at a temperature of 242 ° C.

At higher temperatures it forms flammable vapor-air mixtures. The compound has a flash point of 142 ° C. The explosion range is between 1.3 vol.% As the lower explosion limit (LEL) and 13.1 vol.% As the upper explosion limit (UEL). The ignition temperature is 330 ° C. The substance therefore falls into temperature class T2.

use

1,5-Pentanediol is used as a plasticizer in the plastics industry. By reaction with potassium iodide , phosphorus pentoxide and phosphoric acid can be 1,5-diiodopentane be won.

Individual evidence

  1. Entry on 1,5-PENTANEDIOL in the CosIng database of the EU Commission, accessed on February 25, 2020.
  2. a b c d e f g h i j Entry for CAS no. 111-29-5 in the GESTIS substance database of the IFA , accessed on December 3, 2018(JavaScript required) .
  3. a b W. E. Kaufmann, R. Adams: The Use of Platinum Oxide in the Reduction of Organic Compounds: IV Reduction of Furfural and its Derivatives , in: J. Am. Chem. Soc. , 1923 , 45 , pp. 3029-3044, doi : 10.1021 / ja01665a033 .
  4. D. Kaufman, W. Reeve: 1,5-Pentanediol In: Organic Syntheses . 26, 1946, p 83, doi : 10.15227 / orgsyn.026.0083 ( PDF ).
  5. Entry on pentanediols. In: Römpp Online . Georg Thieme Verlag, accessed on July 25, 2019.
  6. E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.
  7. TRIPURARI PUJAN: Synthesis, Reactions, Characterization and Supramolecular Associations of Some Organotellurium Derivatives ( Memento from July 5, 2017 in the Internet Archive ), LUCKNOW (INDIA), 2013, accessed on October 31, 2018