1,4-Butanediol diglycidyl ether

1,4-Butanediol diglycidyl ether (B14DODGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has two epoxide (oxirane) groups per molecule.[1] Its main use is in modifying epoxy resins especially viscosity reduction.

1,4-Butanediol diglycidyl ether
Names
IUPAC name
2-[4-(Oxiran-2-ylmethoxy)butoxymethyl]oxirane
Other names
    • 1,4-Bis(2,3-epoxypropoxy)butane
    • (Tetramethylenebis(oxymethylene))dioxirane
    • 1,4-Bis(2,3-epoxypropyloxy)butane
    • 1,4-Bis(glycidyloxy)butane
    • 1,4-Bis(oxiranylmethyloxy)butane
    • 1,4-Butane diglycidyl ether
    • 1,4-Butanediol diglycidyl ether
    • 1,4-Diglycidyloxybutane
    • Butane-1:4-diol diglycidyl ether
    • Butanediol diglycidyl ether
    • Tetramethylene glycol diglycidyl ether
    • 2,2'-(1,4-Butanediylbis(oxymethylene)bisoxirane)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.017.611
EC Number
  • 219-371-7
KEGG
  • InChI=1S/C10H18O4/c1(3-11-5-9-7-13-9)2-4-12-6-10-8-14-10/h9-10H,1-8H2
    Key: SHKUUQIDMUMQQK-UHFFFAOYSA-N
  • C1C(O1)COCCCCOCC2CO2
Properties
C10H18O4
Molar mass 202.250 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is REACH registered.[2] The IUPAC name is 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane.

Synthesis

1,4-Butanediol and epichlorohydrin are reacted in the presence of a Lewis acid as catalyst to form a halohydrin: each hydroxyl group of the diol reacts with an epoxide on epichlorohydrin. This process is followed by washing with sodium hydroxideto re-form the epoxide rings in dehydrochlorination reaction.[3] One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

Uses

A key use is modifying the viscosity and properties of epoxy resins[4] which may then be formulated into CASE applications: Coatings,[5] Adhesives, Sealants and Elastomers, fillers, putties, plasters, modelling clay and semiconductors. It also has a number of medical applications.[6][7][8] The molecule is also used to synthesize other molecules.[9][10] As an Epoxy modifier it is classed as an epoxy Reactive diluent.

Toxicity

The toxicity is fairly well known and understood and is rated as a severe skin and eye irritant. Contact dermatitis is also possible.[11][12]

References
  1. PubChem. "1,4-Butanediol diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-02.
  2. "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-04-02.
  3. 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.
  4. 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, retrieved 2022-03-29
  5. Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" page 23 Master of Science Thesis April 1997 Imperial College London
  6. Ji, Gyu Yeul; Oh, Chang Hyun; Moon, Byung Gwan; Yi, Seong; Han, In Bo; Heo, Dong Hwa; Kim, Ki-Tack; Shin, Dong Ah; Kim, Keung Nyun (June 2015). "Efficacy and Safety of Sodium Hyaluronate with 1,4-Butanediol Diglycidyl Ether Compared to Sodium Carboxymethylcellulose in Preventing Adhesion Formation after Lumbar Discectomy". Korean Journal of Spine. 12 (2): 41–47. doi:10.14245/kjs.2015.12.2.41. ISSN 1738-2262. PMC 4513167. PMID 26217381.
  7. Nicoletti, A.; Fiorini, M.; Paolillo, J.; Dolcini, L.; Sandri, M.; Pressato, D. (2013-01-01). "Effects of different crosslinking conditions on the chemical–physical properties of a novel bio-inspired composite scaffold stabilised with 1,4-butanediol diglycidyl ether (BDDGE)". Journal of Materials Science: Materials in Medicine. 24 (1): 17–35. doi:10.1007/s10856-012-4782-4. ISSN 1573-4838. PMID 23053811. S2CID 22093094.
  8. Fiorani, Andrea; Gualandi, Chiara; Panseri, Silvia; Montesi, Monica; Marcacci, Maurilio; Focarete, Maria Letizia; Bigi, Adriana (2014-10-01). "Comparative performance of collagen nanofibers electrospun from different solvents and stabilized by different crosslinkers". Journal of Materials Science: Materials in Medicine. 25 (10): 2313–2321. doi:10.1007/s10856-014-5196-2. ISSN 1573-4838. PMID 24664673. S2CID 5270837.
  9. Wu, Chi; Zuo, Ju; Chu, Benjamin (February 1989). "Molecular weight distribution of a branched epoxy polymer: 1,4-butanediol diglycidyl ether with cis-1,2-cyclohexanedicarboxylic anhydride". Macromolecules. 22 (2): 633–639. Bibcode:1989MaMol..22..633W. doi:10.1021/ma00192a021. ISSN 0024-9297.
  10. Xue, Yu; Chen, Hongyue; Xu, Chao; Yu, Dinghua; Xu, Huajin; Hu, Yi (2020). "Synthesis of hyaluronic acid hydrogels by crosslinking the mixture of high-molecular-weight hyaluronic acid and low-molecular-weight hyaluronic acid with 1,4-butanediol diglycidyl ether". RSC Advances. 10 (12): 7206–7213. Bibcode:2020RSCAd..10.7206X. doi:10.1039/C9RA09271D. S2CID 214083413.
  11. "1,4-Butanediol diglycidyl ether - Hazardous Agents | Haz-Map". haz-map.com. Retrieved 2022-04-02.
  12. Jolanki, Riitta; Estlander, Tuula; Kanerva, Lasse (February 1987). "Contact allergy to an epoxy reactive diluent: 1,4-butanediol diglycidyl ether". Contact Dermatatis. 16 (2): 87–92. doi:10.1111/j.1600-0536.1987.tb01385.x. PMID 2952443. S2CID 36846087 – via Wiley online.

Further reading

External websites
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