Bisphenol A diglycidyl ether

Summary

Bisphenol A diglycidyl ether
Chemical structure of bisphenol A diglycidyl ether
Names
Preferred IUPAC name
5,5-Dimethyl-3,7-dioxa-1,9(2)-bis(oxirana)-4,6(2,4)-dibenzenanonaphane
Other names
Diglycidyl ether of bisphenol A; 2,2-Bis(4-glycidyloxyphenyl)propane; Epoxide A
Identifiers
  • 1675-54-3 checkY
3D model (JSmol)
  • Interactive image
Abbreviations BADGE; DGEBA
ChemSpider
  • 2199 ☒N
ECHA InfoCard 100.015.294 Edit this at Wikidata
EC Number
  • 216-823-5
KEGG
  • C14348 ☒N
MeSH C019273
  • 2286
UNII
  • F3XRM1NX4H checkY
  • DTXSID6024624 Edit this at Wikidata
  • InChI=1S/C21H24O4/c1-21(2,15-3-7-17(8-4-15)22-11-19-13-24-19)16-5-9-18(10-6-16)23-12-20-14-25-20/h3-10,19-20H,11-14H2,1-2H3 ☒N
    Key: LCFVJGUPQDGYKZ-UHFFFAOYSA-N ☒N
  • InChI=1/C21H24O4/c1-21(2,15-3-7-17(8-4-15)22-11-19-13-24-19)16-5-9-18(10-6-16)23-12-20-14-25-20/h3-10,19-20H,11-14H2,1-2H3
    Key: LCFVJGUPQDGYKZ-UHFFFAOYAQ
  • CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4
Properties
C21H24O4
Molar mass 340.419 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Bisphenol A diglycidyl ether (commonly abbreviated BADGE or DGEBA) is an organic compound used as constituent of epoxy resins. The compound is a colorless solid (commercial samples can appear yellow) that melts slightly above room temperature.[1]

Preparation and reactions

It is prepared by O-alkylation of bisphenol A with epichlorohydrin. This reaction mainly affords bisphenol A diglycidyl ether, as well as some oligomer. The degree of polymerization may be as low as 0.1.[2] The epoxide content of such epoxy resins is of interest. This parameter is commonly expressed as the epoxide number, which is the number of epoxide equivalents in 1 kg of resin (Eq./kg), or as the equivalent weight, which is the weight in grams of resin containing 1 mole equivalent of epoxide (g/mol). Since unsymmetrical epoxides are chiral, the bis epoxide consists of three stereoisomers, although these are not separated.

Bisphenol A diglycidyl ether slowly hydrolyzes to 2,2-bis[4(2,3-hydroxypropoxy)phenyl)propane (bis-HPPP).

Similarly, DGEBA reacts with acrylic acid to give vinyl ester resins. The reaction results in opening of the epoxide ring, generating unsaturated esters at each terminus of the molecule. Such materials are often diluted with styrene and converted to resin.

Epoxy resins are thermosetting polymers, which are crosslinked using hardeners (curing agents). The most common curing agents for epoxy resins are polyamines, aminoamides, and phenolic compounds.[3]

Safety

BADGE is highly reactive and forms a number of species upon exposure to water or HCl and many of these compounds (including BADGE) are suspected endocrine disruptors[4] Hydrolysis of the ether bonds liberates bisphenol A, which is also strongly suspected of being an endocrine disruptor.[5][6] From the 1990s onward, concern has been raised over the use of BADGE-based epoxy resins in the lining of some tin cans for foodstuffs, with the chemical being found to leach into foods.[5]

See also

References

  1. ^ Pham, Ha Q.; Marks, Maurice J. (2012). "Epoxy Resins". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_547.pub2.
  2. ^ Mark, Herman (16 October 2013). "Epoxy Resins". Encyclopedia of Polymer Science and Technology. ISBN 9780470073698.
  3. ^ Forrest, M.J.: Coatings and Inks for Food Contact Materials, in RAPRA review reports, vol. 16, no. 6 (2005), p.8
  4. ^ Wang, Dongqi; Zhao, Haoduo; Fei, Xunchang; Synder, Shane Allen; Fang, Mingliang; Liu, Min (October 2021). "A comprehensive review on the analytical method, occurrence, transformation and toxicity of a reactive pollutant: BADGE". Environment International. 155: 106701. doi:10.1016/j.envint.2021.106701.
  5. ^ a b Walfried Rauter, Gerald Dickinger, Rudolf Zihlarz and Josef Lintschinger, "Determination of Bisphenol A diglycidyl ether (BADGE) and its hydrolysis products in canned oily foods from the Austrian market", Z. Lebensm. Unters. Forsch. A 208 (1999) 208–211
  6. ^ "Leitlinie zur hygienischen Beurteilung von organischen Beschichtungen im Kontakt mit Trinkwasser (Beschichtungsleitlinie)" [Guideline for public health evaluation of organic chemical coatings in contact with drinking water (coating guideline)] (PDF). www.umweltbundesamt.de (in German). 16 March 2016.