1,4-Cyclohexanedimethanol diglycidyl ether

1,4-Cyclohexanedimethanol diglycidyl ether is an organic chemical in the glycidyl ether family.[2] It has the formula C14H24O4 and the IUPAC name is 2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane, and the CAS number 14228-73-0.[3] It is REACH registered in Europe.[4] It is an industrial chemical and a key use is in the reduction of viscosity of epoxy resin systems functioning as a reactive diluent.[5][6]

1,4-Cyclohexanedimethanol diglycidyl ether
Names
IUPAC name
2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane
Other names
    • 1,4-Bis(glycidyloxymethyl)cyclohexane
    • 1,4-Bis((2,3-epoxypropoxy)methyl)cyclohexane
    • 2,2'-(1,4-Cyclohexanediylbis(methyleneoxymethylene))bis-oxirane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.034.620
EC Number
  • 238-098-4
  • InChI=1S/C14H24O4/c1-2-12(6-16-8-14-10-18-14)4-3-11(1)5-15-7-13-9-17-13/h11-14H,1-10H2
    Key: VQMQXWYQIIUJIT-UHFFFAOYSA-N
  • C1CC(CCC1COCC2CO2)COCC3CO3
Properties
C14H24O4
Molar mass 256.342 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H317, H319, H412
P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P313, P337+P317, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synonyms

The material is known under various names which include:[7]

  • 2,2'-[1,4-Cyclohexanediylbis(methyleneoxymethylene)]bis[oxirane]
  • 1,4-Bis(glycidoxymethyl)cyclohexane
  • 1,4-Bis(hydroxymethyl)cyclohexane diglycidyl Ether
  • 1,4-Bis[(2,3-epoxypropoxy)methyl]cyclohexane
  • 1,4-Bis[(glycidyloxy)methyl]cyclohexane
  • 1,4-Cyclohexanedimethanol diglycidyl Ether

Manufacture

The manufacturing process involves reacting cyclohexanedimethanol with epichlorohydrin, using a Lewis acid as catalyst, to form a halohydrin. This is followed by washing with sodium hydroxide in a dehydrochlorination step to form the epoxide rings.[8] The waste products are water and sodium chloride and excess caustic soda. One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

Uses

As the molecule has oxirane functionality, a key use is reducing the viscosity of epoxy resins.[9] These reactive diluent modified epoxy resins may then be further formulated into which may then be formulated into CASE applications: Coatings,[10] Adhesives, Sealants,[11] Elastomers, and electronic encapsulant.[12] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[13][14]

It is also used as a monomer in UV curing systems.[15] In addition it is used to synthesize other molecules such as the acrylated version.[16]

Toxicology

The material is classed as a skin irritant.[17][18]

See also

References
  1. "1,4-Bis((2,3-epoxypropoxy)methyl)cyclohexane". pubchem.ncbi.nlm.nih.gov. Retrieved 12 April 2022.
  2. "1,4-Cyclohexanedimethanol diglycidyl ether". www.carbosynth.com. Archived from the original on 2022-04-11. Retrieved 2022-04-10.
  3. PubChem. "1,4-Bis((2,3-epoxypropoxy)methyl)cyclohexane". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2022-04-10. Retrieved 2022-04-10.
  4. "Substance Information – ECHA". echa.europa.eu. Archived from the original on 2022-04-11. Retrieved 2022-04-11.
  5. EP 2621994, Hefner, Robert E., "Epoxy resin compositions", published 2013-08-07, assigned to Dow Global Technologies LLC
  6. Jagtap, Ameya Rajendra; More, Aarti (2022-08-01). "Developments in reactive diluents: a review". Polymer Bulletin. 79 (8): 5667–5708. doi:10.1007/s00289-021-03808-5. ISSN 1436-2449. S2CID 235678040.
  7. "14228-73-0 | 1,4-Cyclohexanedimethanol Diglycidyl Ether | 2,2'-[1,4-Cyclohexanediylbis(methyleneoxymethylene)]bis[oxirane]; 1,4-Bis(glycidoxymethyl)cyclohexane; 1,4-Bis(hydroxymethyl)cyclohexane diglycidyl Ether; 1,4-Bis[(2,3-epoxypropoxy)methyl]cyclohexane; 1,4-Bis[(glycidyloxy)methyl]cyclohexane; 1,4-Cyclohexanedimethanol diglycidyl Ether | C
    14    H
    24    O
    4     | TRC"    . www.trc-canada.com. Archived from the original on 2022-04-11. Retrieved 2022-04-11.
  8. Crivello, James V. (2006). "Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization". Journal of Polymer Science Part A: Polymer Chemistry. 44 (21): 6435–6448. Bibcode:2006JPoSA..44.6435C. doi:10.1002/pola.21761. ISSN 0887-624X.
  9. Monte, Salvatore J. (1998), Pritchard, Geoffrey (ed.), "Diluents and viscosity modifiers for epoxy resins", Plastics Additives: An A-Z reference, Polymer Science and Technology Series, Dordrecht: Springer Netherlands, vol. 1, pp. 211–216, doi:10.1007/978-94-011-5862-6_24, ISBN 978-94-011-5862-6, archived from the original on 2022-04-11, retrieved 2022-03-29
  10. WO application 2015095994, Shen, Yue; Zhan, Fu & Wu, Yan et al., "Epoxy resin composition", published 2015-07-02, assigned to Dow Global Technologies LLC
  11. "14228-73-0 | CAS DataBase". www.chemicalbook.com. Archived from the original on 2022-04-11. Retrieved 2022-04-11.
  12. JP 4965715, Hosono, Yohei & Homma, Hiroki, "Epoxy resin composition and semiconductor sealing material using the same", published 2012-07-04, assigned to Namics Corp.
  13. Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali (2019-08-01). "The effect of reactive diluent on mechanical properties and microstructure of epoxy resins". Polymer Bulletin. 76 (8): 3905–3927. doi:10.1007/s00289-018-2577-6. ISSN 1436-2449. S2CID 105389177.
  14. Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas (2023-07-01). "The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings". Journal of Coatings Technology and Research. 20 (4): 1207–1221. doi:10.1007/s11998-022-00737-4. ISSN 1935-3804. S2CID 256749849.
  15. Sangermano, M.; Bongiovanni, R.; Malucelli, G.; Priola, A.; Pollicino, A.; Recca, A. (2003-08-08). "Fluorinated epoxides as surface modifying agents of UV-curable systems". Journal of Applied Polymer Science. 89 (6): 1524–1529. doi:10.1002/app.12244. ISSN 0021-8995.
  16. Huang, Biwu; Deng, Chong; Xu, Qinchang; Chen, Weiqing; Zou, Huaihua (2014-12-01). "Synthesis of a novel UV-curable oligmer [sic] 1,4-cyclohexanedimethanol glycidyl ether acrylate and study on its UV-curing properties". Journal of Wuhan University of Technology-Mater. Sci. Ed. 29 (6): 1283–1289. doi:10.1007/s11595-014-1082-5. ISSN 1993-0437. S2CID 94880993. Archived from the original on 2022-04-11. Retrieved 2022-04-11.
  17. "An assessment of skin sensitisation by the use of epoxy resin in the construction industry" (PDF). UK Health and Safety Executive. April 2022. Archived (PDF) from the original on 2021-10-09. Retrieved 2022-04-11.
  18. Berdasco, Nancy Anne M.; Waechter, John M. (2012-08-17), Bingham, Eula; Cohrssen, Barbara; Powell, Charles H. (eds.), "Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds", Patty's Toxicology, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. 491–528, doi:10.1002/0471435139.tox083.pub2, ISBN 978-0-471-12547-1, retrieved 2022-07-28

Further reading
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