View source for Bisphenol A diglycidyl ether

{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 411628499
|Name = Bisphenol A diglycidyl ether
|ImageFile = Bisphenol A diglycidyl ether 200.svg
|ImageName = Chemical structure of bisphenol A diglycidyl ether
|ImageSize = 250
|PIN = 5,5-Dimethyl-3,7-dioxa-1,9(2)-bis(oxirana)-4,6(2,4)-dibenzenanonaphane
|OtherNames = Diglycidyl ether of bisphenol A; 2,2-Bis(4-glycidyloxyphenyl)propane; Epoxide A
|Section1={{Chembox Identifiers
|Abbreviations = BADGE; DGEBA
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 1675-54-3
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = F3XRM1NX4H
|PubChem = 2286
|KEGG_Ref = {{keggcite|changed|kegg}}
|KEGG = C14348
|EINECS = 216-823-5
|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
|ChemSpiderID = 2199
|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
|InChIKey = LCFVJGUPQDGYKZ-UHFFFAOYAQ
|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
|StdInChI = 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
|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
|StdInChIKey = LCFVJGUPQDGYKZ-UHFFFAOYSA-N
|MeSHName = C019273
|SMILES = CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4
}}
|Section2={{Chembox Properties
|C=21 | H=24 | O=4
}}
}}
'''Bisphenol A diglycidyl ether''' (commonly abbreviated '''BADGE''' or '''DGEBA''') is an [[organic compound]] and is a liquid [[epoxy resin]].<ref>{{Cite book |last=Ellis |first=Bryan |url=https://www.worldcat.org/oclc/851368739 |title=Chemistry and Technology of Epoxy Resins |date=1993 |publisher=Springer Netherlands |isbn=978-94-011-2932-9 |location=Dordrecht |oclc=851368739}}</ref><ref>{{Cite web |title=Bisphenol A Liquid Epoxy Resins {{!}} Business & Products |url=https://www.dic-global.com/en/products/epoxy/bpa_liquid/ |access-date=2023-01-11 |website=DIC Corporation |language=en}}</ref><ref>{{Cite web |title=Epoxy: A Complete Guide |url=https://www.coppsindustries.com/epoxy-a-complete-guide/ |access-date=2023-01-11 |website=Copps Industries |archive-date=2023-01-11 |archive-url=https://web.archive.org/web/20230111193542/https://www.coppsindustries.com/epoxy-a-complete-guide/ |url-status=dead }}</ref><ref>{{Cite web |last=PubChem |title=Bisphenol A diglycidyl ether |url=https://pubchem.ncbi.nlm.nih.gov/compound/2286 |access-date=2023-01-11 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref><ref>{{Cite web |title=2,2-Bis(4-glycidyloxyphenyl)propane 1675-54-3 {{!}} TCI AMERICA |url=https://www.tcichemicals.com/US/en/p/B1796 |access-date=2023-01-11 |website=www.tcichemicals.com}}</ref>  The compound is a colorless viscous liquid (commercial samples can appear pale straw-coloured).<ref>Hofer, Arnold; Schneider, Hildegard, and Siegenthaler, Nikolaus (1996) "Epoxy resin mixtures containing advancement catalysts", {{US Patent|5521261}}.</ref><ref name="Ullmann">{{Ullmann|last1=Pham|first1=Ha Q.|last2=Marks|first2=Maurice J.|title=Epoxy Resins|year=2012|doi=10.1002/14356007.a09_547.pub2}}</ref> It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.<ref>{{Citation |last=Ashcroft |first=W. R. |title=Curing agents for epoxy resins |date=1993 |url=http://link.springer.com/10.1007/978-94-011-2932-9_2 |work=Chemistry and Technology of Epoxy Resins |pages=37–71 |editor-last=Ellis |editor-first=Bryan |place=Dordrecht |publisher=Springer Netherlands |language=en |doi=10.1007/978-94-011-2932-9_2 |isbn=978-94-010-5302-0 |access-date=2023-01-11}}</ref>
[[File:Epoxy prepolymer chemical structure.png|thumb|Structure of bisphenol-A diglycidyl ether epoxy resin: ''n'' denotes the number of polymerized subunits and is typically in the range from 0 to 25]]
==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.<ref>{{cite encyclopedia|last1=Mark|first1=Herman |encyclopedia=Encyclopedia of Polymer Science and Technology|date=16 October 2013 |isbn=9780470073698 |url=https://books.google.com/books?id=Vfh1AQAAQBAJ&q=DGEBA+degree+of+polymerization&pg=PA388|article = Epoxy Resins}}</ref>  The epoxide content of such epoxy resins is of interest.  This parameter is commonly expressed as the [[epoxy value|epoxide number]], which is the number of epoxide equivalents in 1&nbsp;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 [[Bis-HPPP|2,2-bis[4(2,3-dihydroxypropoxy)phenyl)propane]] (bis-HPPP).
Similarly, DGEBA reacts with acrylic acid to give [[vinyl ester resin]]s.  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 [[polyamine]]s, aminoamides, and phenolic compounds.<ref name="Coatings and Inks">Forrest, M.J.: Coatings and Inks for Food Contact Materials, in RAPRA review reports, vol. 16, no. 6 (2005), p.8</ref>
==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 disruptor]]s.<ref>{{cite journal |last1=Wang |first1=Dongqi |last2=Zhao |first2=Haoduo |last3=Fei |first3=Xunchang |last4=Synder |first4=Shane Allen |last5=Fang |first5=Mingliang |last6=Liu |first6=Min |title=A comprehensive review on the analytical method, occurrence, transformation and toxicity of a reactive pollutant: BADGE |journal=Environment International |date=October 2021 |volume=155 |pages=106701 |doi=10.1016/j.envint.2021.106701|pmid=34146765 |doi-access=free|bibcode=2021EnInt.15506701W |hdl=10356/161451 |hdl-access=free }}</ref> Hydrolysis of the [[ether]] bonds liberates bisphenol A, which is also strongly suspected of being an endocrine disruptor.<ref name="rauter">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</ref><ref name="Coating Guideline">{{cite web |trans-title = Guideline for public health evaluation of organic chemical coatings in contact with drinking water (coating guideline) |date = 16 March 2016 |website = www.umweltbundesamt.de |language = de |url = https://www.umweltbundesamt.de/sites/default/files/medien/374/dokumente/160316_beschichtungsleitlinie_neu.pdf |title = Leitlinie zur hygienischen Beurteilung von organischen Beschichtungen im Kontakt mit Trinkwasser (Beschichtungsleitlinie) |access-date = 6 October 2019 |archive-date = 9 January 2017 |archive-url = https://web.archive.org/web/20170109035010/http://www.umweltbundesamt.de/sites/default/files/medien/374/dokumente/160316_beschichtungsleitlinie_neu.pdf |url-status = dead }}</ref>
From the 1990s onward, concern has been raised over the use of BADGE-based epoxy resins in the lining of some cans for foodstuffs, with the chemical being found to leach into foods.<ref name="rauter" /><ref>{{Citation |last1=Berdasco |first1=Nancy Anne M. |title=Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds |date=2012-08-17 |url=https://onlinelibrary.wiley.com/doi/10.1002/0471435139.tox083.pub2 |work=Patty's Toxicology |pages=491–528 |editor-last=Bingham |editor-first=Eula |place=Hoboken, NJ, USA |publisher=John Wiley & Sons, Inc. |language=en |doi=10.1002/0471435139.tox083.pub2 |isbn=978-0-471-12547-1 |access-date=2022-07-28 |last2=Waechter |first2=John M. |editor2-last=Cohrssen |editor2-first=Barbara |editor3-last=Powell |editor3-first=Charles H.}}</ref> Bisphenol A Diglycidyl ether-based epoxy coatings are extensively used for coating the inside of cans which come into contact with food and are thus [[food contact materials]]. The materials and analogues and conjugates have been extensively tested for and analytical methods developed.<ref>{{Cite journal |last1=Lestido-Cardama |first1=Antía |last2=Sendón |first2=Raquel |last3=Rodríguez Bernaldo de Quirós |first3=Ana |date=2022-11-01 |title=Tentative identification of BADGE derivatives in epoxy type coatings in a model sample: a beverage can |url=https://doi.org/10.1007/s11998-022-00662-6 |journal=Journal of Coatings Technology and Research |language=en |volume=19 |issue=6 |pages=1893–1900 |doi=10.1007/s11998-022-00662-6 |s2cid=251912604 |issn=1935-3804}}</ref><ref>{{Cite journal |last1=Beszterda |first1=Monika |last2=Tądrowska |first2=Magdalena |last3=Frański |first3=Rafał |date=2022-11-01 |title=Multi-detection method for the fast screening of bisphenol A diglycidyl ether conjugates in the can-coating material |url=https://doi.org/10.1007/s11998-022-00668-0 |journal=Journal of Coatings Technology and Research |language=en |volume=19 |issue=6 |pages=1901–1907 |doi=10.1007/s11998-022-00668-0 |s2cid=252213795 |issn=1935-3804}}</ref>
==See also==
* [[Bisphenol AF]] (BPAF)
* [[Bisphenol S]] (BPS)
* [[EPI-001]]
==References==
{{Reflist}}
{{Androgen receptor modulators}}
{{PPAR modulators}}
{{Glycidyl ethers}}
[[Category:Glycidyl ethers]]
[[Category:IARC Group 3 carcinogens]]
[[Category:Nonsteroidal antiandrogens]]
[[Category:Phenol ethers]]
[[Category:PPAR agonists]]
[[Category:2,2-Bis(4-hydroxyphenyl)propanes]]