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]

References

  1. ↑ PubChem. "2,5-Hexanediol". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-01-04.
  2. ↑ "hexane-2,5-diol properties". materials.springer.com. Retrieved 2024-01-04.
  3. ↑ Peter Werle; Marcus Morawietz; Stefan Lundmark; Kent Sörensen; Esko Karvinen; Juha Lehtonen (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2. ISBN   978-3-527-30673-2.
  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.
  9. ↑ Lieser, Joan K. (July 1983). "A Simple Synthesis of (S, S)-2, 5-Hexanediol" . Synthetic Communications. 13 (9): 765–767. doi:10.1080/00397918308063707. ISSN   0039-7911.
  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.
  14. ↑ Herrmann, Wolfgang; Cornils, Boy; Zanthoff, Horst; Xu, Jian-He, eds. (2019-04-08). Catalysis from A to Z: A Concise Encyclopedia (1 ed.). Wiley. doi:10.1002/9783527809080.cataz09294. ISBN   978-3-527-34311-9. S2CID   219100145.
  15. ↑ Kannan, K.; Singh, K. P.; Goel, S. K.; Shanker, Ravi (1985-02-01). "Effect of 2,5-hexanediol on immunocompetence of mice" . Environmental Research. 36 (1): 14–25. Bibcode:1985ER.....36...14K. doi:10.1016/0013-9351(85)90003-9. ISSN   0013-9351. PMID   3967636.
  16. ↑ Abou-Donia, Mohamed B.; Makkawy, H. M.; Campbell, Gerald M. (January 1985). "Pattern of neurotoxicity of n -hexane, methyl n -butyl ketone, 2,5-hexanediol, and 2,5-hexanedione alone and in combination with O -ethyl O -4-nitrophenyl phenylphosphonothioate in hens" . Journal of Toxicology and Environmental Health. 16 (1): 85–100. Bibcode:1985JTEH...16...85A. doi:10.1080/15287398509530721. ISSN   0098-4108. PMID   4068058.
  17. ↑ Abou-Donia, Mohamed B.; Makkawy, Hany-Anwar M.; Graham, Doyle G. (1982-03-15). "The relative neurotoxicities of n-hexane, methyl n-butyl ketone, 2,5-hexanediol, and 2,5-hexanedione following oral or intraperitoneal administration in hens" . Toxicology and Applied Pharmacology. 62 (3): 369–389. Bibcode:1982ToxAP..62..369A. doi:10.1016/0041-008X(82)90139-9. ISSN   0041-008X. PMID   7071856.
  18. ↑ Eben, Anneliese; Flucke, Winfried; Mihail, Florin; Thyssen, Jürgen; Kimmerle, Georg (1979-06-01). "Toxicological and metabolic studies of methyl n-butylketone, 2,5-hexanedione, and 2,5-hexanediol in male rats" . Ecotoxicology and Environmental Safety. 3 (2): 204–217. Bibcode:1979EcoES...3..204E. doi:10.1016/0147-6513(79)90012-5. ISSN   0147-6513. PMID   540560.
  19. ↑ Jones, H. B.; Cavanagh, J. B. (1982-12-01). "Recovery from 2,5-hexanediol intoxication of the retinotectal tract of the rat" . Acta Neuropathologica. 58 (4): 286–290. doi:10.1007/BF00688611. ISSN   1432-0533. PMID   6891552. S2CID   39467729.
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