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Diglycidyl resorcinol ether

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Diglycidyl resorcinol ether
Names
IUPAC name
2-[[3-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane
Other names
1,3-Bis(2,3-epoxypropoxy)benzene; 1,3-Diglycidyloxybenzene; 2,2'-(1,3-Phenylenebis(oxymethylene))bisoxirane; Araldite ERE 1359; m-bis(2,3-epoxypropoxy)-Benzene ; Diglycidyl ether of resorcinol; Diglycidylresorcinol ether; m-Bis(2,3-epoxypropoxy)benzene; m-Bis(glycidyloxy)benzene; Resorcinol bis(2,3-epoxypropyl) ether; Resorcinol diglycidyl ether; Oxirane, 2,2'-(1,3-phenylenebis(oxymethylene))bis-
Identifiers
3D model (JSmol)
Abbreviations DGRE
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.716 Edit this at Wikidata
EC Number
  • 202-987-5
KEGG
RTECS number
  • VH1050000
UNII
UN number 2811
  • InChI=1S/C12H14O4/c1-2-9(13-5-11-7-15-11)4-10(3-1)14-6-12-8-16-12/h1-4,11-12H,5-8H2
    Key: WPYCRFCQABTEKC-UHFFFAOYSA-N
  • C1C(O1)COC2=CC(=CC=C2)OCC3CO3
Properties
C12H14O4
Molar mass 222.239 g/mol
Density 1.21
Melting point 32–33 °C (90–91 °F; 305–306 K)
Hazards
GHS labelling:[1]
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H302, H311, H315, H317, H319, H341, H350, H412
P203, P261, P264, P264+P265, P270, P272, P273, P280, P281, P301+P317, P302+P352, P305+P351+P338, P316, P318, P321, P330, P332+P317, P333+P313, P337+P317, P361+P364, P362+P364, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diglycidyl resorcinol ether, also called Resorcinol diglycidyl ether (RDGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether.[2][3]

The formula is C12H14O4[4] and the CAS Registry Number 101-90-6.[5] It is one of a number of glycidyl ethers available commercially that are used to reduce the viscosity of epoxy resins.[6] These are then further used in coatings, sealants, adhesives and elastomers.[7] It has the CAS Registry Number 101-90-6.[8] It has the IUPAC name 2-[[3-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane and is registered on TSCA (Toxic Substances Control Act of 1976) as Oxirane, 2,2'-[1,3-phenylenebis(oxymethylene)]bis-.[9] It is REACH registered and on EINECS.[10]

Synonyms

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  • 1,3-Bis(2,3-epoxypropoxy)benzene
  • 1,3-Diglycidyloxybenzene
  • 2,2'-(1,3-Phenylenebis(oxymethylene))bisoxirane[11]
  • Araldite ERE 1359
  • Diglycidyl ether of resorcinol
  • m-Bis(2,3-epoxypropoxy)benzene[12]
  • meta-Bis(glycidyloxy)benzene
  • Oxirane, 2,2'-(1,3-phenylenebis(oxymethylene))bis-
  • RDGE
  • Resorcinol bis(2,3-epoxypropyl)ether
  • Resorcinol diglycidyl ether

Synthesis

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Resorcinol and epichlorohydrin are reacted in the presence of a base and not a Lewis acid catalyst as normal with glycidyl ethers. A halohydrin is formed. This is followed by washing with sodium hydroxide in dehydrochlorination step. This forms Resorcinol diglycidyl ether.[13] 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

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The material has two oxirane groups and is thus used mainly in epoxy resins systems as a reactive diluent and modifier.[14][15][16] It has found use as an additive for bonding resin systems[17] and also as a modifier for phenolic resins[18] Despite the toxicity it generally gives excellent properties and so there are military applications.[19] The use of the diluent does effect mechanical properties and microstructure of epoxy resins. However, this diluent is one of the best for not reducing properties too much.[20][21]

Toxicology

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It is classed as IARC group 2B by the International Agency for Research on Cancer. The toxicology has been studied for a long time and is fairly well understood.[22][23]

See also

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References

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  1. ^ "Diglycidyl resorcinol ether". pubchem.ncbi.nlm.nih.gov. Retrieved 27 May 2022.
  2. ^ "Resorcinol diglycidyl ether | C12H14O4 | ChemSpider". www.chemspider.com. Retrieved 2022-05-25.
  3. ^ "NCI Thesaurus". ncithesaurus.nci.nih.gov. Retrieved 2022-05-25.
  4. ^ "Resorcinol diglycidyl ether". www.chemsrc.com. Retrieved 2022-05-25.
  5. ^ Inc, Abt Associates. "Toxics Release Inventory (TRI) GuideME". ordspub.epa.gov. Retrieved 2022-05-25. {{cite web}}: |last= has generic name (help)
  6. ^ "Resorcinol diglycidyl ether | CAS 101-90-6". www.scbt.com. Retrieved 2022-05-25.
  7. ^ Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 23,24,39 Master of Science Thesis April 1997 Imperial College London
  8. ^ PubChem. "Diglycidyl resorcinol ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-05-27.
  9. ^ "New Jersey Resorcinol Diglycidyl Ether Hazardous Substance Sheet" (PDF). New Jersey government.
  10. ^ "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-05-27.
  11. ^ "Oxirane, 2,2'-[1,3-phenylenebis(oxymethylene)]bis-". webbook.nist.gov. Retrieved 2022-05-25.
  12. ^ PubChem. "Hazardous Substances Data Bank (HSDB) : 4166". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-05-25.
  13. ^ 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.
  14. ^ 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.
  15. ^ Sorokin, V. P.; Bobylev, V. A.; Eselev, A. D. (2007-09-01). "Epoxy resins based on resorcinol and its derivatives". Polymer Science Series C. 49 (3): 272–275. doi:10.1134/S1811238207030149. ISSN 1555-614X. S2CID 94228644.
  16. ^ "Diglycidyl Resorcinol Ether - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2022-05-25.
  17. ^ WO application 2021124125, Zafar, Ashar; Pham, Huynh Tram Anh & Hägg, Katarina et al., "Process for the preparation of a bonding resin", published 2021-06-24, assigned to Stora Enso Oyj 
  18. ^ US 11161976, Goodwin, Kimberly; Viswanathan, Ganapathy S. & Peace, Scott et al., "Phenolic epoxy system", published 2021-11-02, assigned to Hexion Vad LLC 
  19. ^ Booth, Hubert J. (1973-07-26). "Synthesis of Epoxy Resins for Property-Structure Studies". Archived from the original on May 14, 2021. {{cite journal}}: Cite journal requires |journal= (help)
  20. ^ 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.
  21. ^ 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.
  22. ^ National Toxicology Program (2011). "Diglycidyl resorcinol ether". Report on Carcinogens: Carcinogen Profiles. 12: 163–164. ISSN 1551-8280. PMID 21852825.
  23. ^ 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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External Websites

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