1,3-butanediol

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Structural formula
Structural formula of 1,3-butanediol
Structural formula without stereochemistry
General
Surname 1,3-butanediol
other names
  • Butane-1,3-diol
  • 1,3-butylene glycol
  • 1,3-BG
  • BUTYLENE GLYCOL ( INCI )
Molecular formula C 4 H 10 O 2
Brief description

colorless, odorless liquid

External identifiers / databases
CAS number
  • 107-88-0 ( racemate )
  • 6290-03-5 [( R ) -1,3-butanediol]
  • 24621-61-2 [( S ) - (+) - 1,3-butanediol]
EC number 203-529-7
ECHA InfoCard 100.003.209
PubChem 7896
ChemSpider 13837670
DrugBank DB02202
Wikidata Q161496
properties
Molar mass 90.12 g mol −1
Physical state

liquid

density

1.01 g cm −3

Melting point

<−50 ° C

boiling point

207 ° C

Vapor pressure

0.08 hPa (20 ° C)

solubility
  • miscible with water
  • soluble in ethanol and acetone
Refractive index

1.44 (20 ° C)

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

1,3-Butanediol is a chemical compound from the group of alcohols , more precisely the diols or butanediols .

Extraction and presentation

By base-catalyzed aldol condensation of acetaldehyde , 3-hydroxybutanal is obtained in the first step . This can be further processed to 1,3-butanediol by hydrogenation , for example on Raney nickel .

Synthesis of 1,3-butanediol

A possible secondary product is 1,3-butadiene obtained by acid-catalyzed dehydration .

properties

1,3-Butanediol, also known synonymously as 1,3-butylene glycol, is a chain-like organic compound that consists of four carbon and eight hydrogen atoms and two hydroxyl groups , making it a diol. 1,3-Butanediol has a center of chirality on the C3 carbon.

The compound is miscible with water, acetone and diethyl ether and soluble in oils and ethanol. The flash point is 116 ° C, the ignition temperature is 375 ° C and the explosion limits are between 1.9% by volume (below the explosion limit) and 12.6% by volume (upper explosion limit).

use

1,3-Butanediol is mainly used as an intermediate in the manufacture of plasticizers for plastics .

Since it is non-toxic and has a slight bacteriostatic and fungicidal effect, it can be used in surfactants or solvents for flavorings.

It is used as part of ear drops with antibiotic and fungicidal effects. (Otobacid N)

Individual evidence

  1. ↑ Entry on BUTYLENE GLYCOL 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 Entry on 1,3-butanediol in the GESTIS substance database of the IFA , accessed on December 22, 2019(JavaScript required) .
  3. ↑ a b c Food and Agriculture Organization of the United Nations: Compendium of Food Additive Specifications Combined Specifications from 1st Through the 37th Meetings, 1956-1990 . Food & Agriculture Org., 1992, ISBN 978-92-5103375-3 , pp. 241 ( limited preview in Google Book search).
  4. ↑ a b Data sheet 1,3-Butanediol anhydrous, ≥ 99% from Sigma-Aldrich , accessed on January 15, 2010 ( PDF ).
  5. ↑ Entry on butanediols. In: Römpp Online . Georg Thieme Verlag, accessed on June 16, 2014.
  6. ↑ fao.org: BUTANE - 1,3 - DIOL , accessed on May 3, 2016
  7. ↑ Victor O. Sheftel: Indirect Food Additives and Polymers Migration and Toxicology . CRC Press, 2000, ISBN 978-1-56670-499-1 , pp. 51 ( limited preview in Google Book search).

Web links

  • Metabolism of R- and S-1,3-butanediol in perfused livers from meal-fed and starved rats; PMC 1132838 (free full text, PDF)