Bisphenol A diglycidyl ether
 | |
| Names | |
|---|---|
| IUPAC name
2-[[4-[2-[4-(Oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenoxy]methyl]oxirane | |
| Other names
Diglycidyl ether of bisphenol A; 2,2-Bis(4-glycidyloxyphenyl)propane; Epoxide A | |
| Identifiers | |
1675-54-3  | |
| Abbreviations | BADGE; DGEBA |
| ChemSpider | 2199  |
| EC Number | 216-823-5 |
| Jmol interactive 3D | Image |
| KEGG | C14348 |
| MeSH | C019273 |
| PubChem | 2286 |
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| |
| Properties | |
| C21H24O4 | |
| Molar mass | 340.42 g·mol−1 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| 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
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).
Epoxy resins are crosslinked using hardeners (curing agents). The most common curing agents for epoxy resins are polyamines, aminoamides, and phenolic compounds.[3]
Safety
Bisphenol A has attracted much attention as a potential endocrine disruptor.[4][5] It has antiandrogen and PPARγ-modulating properties.
BADGE is listed as an IARC Group 3 carcinogen, meaning it is "not classifiable as to its carcinogenicity to humans".[6] From the 1990s onward, concern has been raised over this possible carcinogenicity because BADGE is also used in epoxy resins in the lining of some tin cans for foodstuffs, and unreacted BADGE may end up in the contents of those cans.[4]
See also
- Bisphenol AF (BPAF)
- Bisphenol S (BPS)
- EPI-001
References
- ↑ Pham, Ha Q.; Marks, Maurice J. (2012). "Epoxy Resins". Ullmann's Encyclopedia of Industrial Chemistry (Wiley-VCH). doi:10.1002/14356007.a09_547.pub2.
- ↑ Mark, Herman. Encyclopedia of Polymer Science and Technology.
- ↑ Forrest, M.J.: Coatings and Inks for Food Contact Materials, in RAPRA review reports, vol. 16, no. 6 (2005), p.8
- 1 2 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
- ↑ Guideline for public health evaluation of organic chemical coatings in contact with drinking water (coating guideline) http://www.umweltbundesamt.de/wasser/themen/downloads/trinkwasser/beschichtungsleitlinie.pdf
- ↑ Group 3: Not classifiable as to carcinogenicity to humans, International Agency for Research on Cancer
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