2,5-Hexanediol

Last updated
2,5-Hexanediol
2,5-Hexandiol Formula V1.svg
2,5-Hexanediol 3D.png
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.019.010 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 220-910-3
PubChem CID
  • InChI=1S/C6H14O2/c1-5(7)3-4-6(2)8/h5-8H,3-4H2,1-2H3
    Key: OHMBHFSEKCCCBW-UHFFFAOYSA-N
  • CC(CCC(C)O)O
Properties
C6H14O2
Molar mass 118.176 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H315, H319, H335
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,5-Hexanediol is an organic compound with the formula CH3CH(OH)CH2CH2CH(OH)CH3. It is both a glycol and a secondary alcohol. [1] It is a colorless water-soluble viscous liquid. [2] [3] [4] The chemical properties are well understood and have been extensively reported and studied. [5] It has the IUPAC name of hexane-2,5-diol [6] and the CAS Registry Number CAS 2935-44-6. [7]

Contents

Other names

Manufacture

One common method of manufacture of the compound is from yeast. [8] Another method involves the reduction of acetonylacetone. [9] The material has two chiral carbons and thus has a number of enantiomers. Processes have been researched and developed to produce enantiopure products and by a continuous process. [10] [11] Some synthesis has been carried out from keto hexanoates. [12]

Uses

One of the uses of the material is to synthesize polyesters. [13] and also fine chemicals. [14]

Toxicity

The toxicity of the material has been studied and is reasonably well understood. [15] [16] [17] [18] It can affect the eyes and has some neurotoxic effects. [19]

Related Research Articles

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References

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  4. "2,5-Hexanediol (CAS 2935-44-6)". Cheméo. Retrieved 2024-01-04.
  5. "2,5-Hexanediol (CAS 2935-44-6)". Cheméo. Retrieved 2024-01-04.
  6. PubChem. "2,5-Hexanediol". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-01-04.
  7. "2,5-Hexanediol". nist.gov.
  8. Xiao, Meitian; Ye, Jing; Zhang, Yawu; Huang, Yayan (2009-06-01). "Reaction Characteristics of Asymmetric Synthesis of (2S,5S)-2,5-Hexanediol Catalyzed with Baker's Yeast Number 6". Chinese Journal of Chemical Engineering. 17 (3): 493–499. doi:10.1016/S1004-9541(08)60236-0. ISSN   1004-9541.
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  10. Haberland, Jürgen; Hummel, Werner; Daussmann, Thomas; Liese, Andreas (2002-07-01). "New Continuous Production Process for Enantiopure (2 R ,5 R )-Hexanediol". Organic Process Research & Development. 6 (4): 458–462. doi:10.1021/op020023t. ISSN   1083-6160.
  11. Schroer, Kirsten; Lütz, Stephan (2009-11-20). "A Continuously Operated Bimembrane Reactor Process for the Biocatalytic Production of (2 R ,5 R )-Hexanediol". Organic Process Research & Development. 13 (6): 1202–1205. doi:10.1021/op9001643. ISSN   1083-6160.
  12. Rudloff, E. von (1958-03-01). "Synthesis of Some Hexanediols". Canadian Journal of Chemistry. 36 (3): 486–491. doi:10.1139/v58-069. ISSN   0008-4042.
  13. O'Malley, James J.; Stauffer, Walter J. (April 1974). "Synthesis and characterization of isomeric polyesters based on sebacic acid and hexanediols". Journal of Polymer Science: Polymer Chemistry Edition. 12 (4): 865–874. Bibcode:1974JPoSA..12..865O. doi:10.1002/pol.1974.170120416. ISSN   0360-6376.
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