Diglycidyl resorcinol ether

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
CAS Number	101-90-6 ;
3D model (JSmol)	Interactive image;
Abbreviations	DGRE
ChEBI	CHEBI:82318;
ChEMBL	ChEMBL1338613;
ChemSpider	7305;
ECHA InfoCard	100.002.716
EC Number	202-987-5;
KEGG	C19228;
PubChem CID	7586;
RTECS number	VH1050000;
UNII	FXN2Y6QZ2W;
UN number	2811
CompTox Dashboard (EPA)	DTXSID2020470 ;
	InChI 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;
	SMILES C1C(O1)COC2=CC(=CC=C2)OCC3CO3;
Properties
Chemical formula	C12H14O4
Molar mass	222.239 g/mol
Density	1.21
Melting point	32–33 °C (90–91 °F; 305–306 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311, H315, H317, H319, H341, H350, H412
Precautionary statements	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). Infobox references

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

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

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

The material has two oxirane groups and is thus used mainly in epoxy resins systems as a reactive diluent and modifier.^[14]^[15] It has found use as an additive for bonding resin systems^[16] and also as a modifier for phenolic resins^[17] Despite the toxicity it generally gives excellent properties and so there are military applications.^[18] 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.^[19]^[20]

Toxicology

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.^[21]^[22]

References

^ "Diglycidyl resorcinol ether". pubchem.ncbi.nlm.nih.gov. Retrieved 27 May 2022.
^ "Resorcinol diglycidyl ether | C12H14O4 | ChemSpider". www.chemspider.com. Retrieved 2022-05-25.
^ "NCI Thesaurus". ncithesaurus.nci.nih.gov. Retrieved 2022-05-25.
^ "Resorcinol diglycidyl ether". www.chemsrc.com. Retrieved 2022-05-25.
^ Inc, Abt Associates. "Toxics Release Inventory (TRI) GuideME". ordspub.epa.gov. Archived from the original on November 28, 2021. Retrieved 2022-05-25. {{cite web}}: |last= has generic name (help)
^ "Resorcinol diglycidyl ether | CAS 101-90-6". www.scbt.com. Retrieved 2022-05-25.
^ 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
^ PubChem. "Diglycidyl resorcinol ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-05-27.
^ "New Jersey Resorcinol Diglycidyl Ether Hazardous Substance Sheet" (PDF). New Jersey government.
^ "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-05-27.
^ "Oxirane, 2,2'-[1,3-phenylenebis(oxymethylene)]bis-". webbook.nist.gov. Retrieved 2022-05-25.
^ PubChem. "Hazardous Substances Data Bank (HSDB) : 4166". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-05-25.
^ 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.
^ Jagtap, Ameya Rajendra; More, Aarti (August 2022). "Developments in reactive diluents: a review". Polymer Bulletin. 79 (8): 5667–5708. doi:10.1007/s00289-021-03808-5.
^ Sorokin, V. P.; Bobylev, V. A.; Eselev, A. D. (September 2007). "Epoxy resins based on resorcinol and its derivatives". Polymer Science Series C. 49 (3): 272–275. doi:10.1134/S1811238207030149.
^ 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
^ US 11161976, Goodwin, Kimberly; Viswanathan, Ganapathy S. & Peace, Scott et al., "Phenolic epoxy system", published 2021-11-02, assigned to Hexion Vad LLC
^ Booth, Hubert J (26 July 1973). Synthesis of Epoxy Resins for Property-Structure Studies (Report). OCLC 831523253. DTIC AD0765694.
^ Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas (July 2023). "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.
^ Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali (August 2019). "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.
^ National Toxicology Program (2011). "Diglycidyl resorcinol ether". Report on Carcinogens: Carcinogen Profiles. 12: 163–164. PMID 21852825.
^ Berdasco, Nancy Anne M.; Waechter, John M. (2012). "Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds". Patty's Toxicology. pp. 491–528. doi:10.1002/0471435139.tox083.pub2. ISBN 978-0-471-31943-6.

External Websites

[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. Archived from the original on November 28, 2021. 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.

[14] Jagtap, Ameya Rajendra; More, Aarti (August 2022). "Developments in reactive diluents: a review". Polymer Bulletin. 79 (8): 5667–5708. doi:10.1007/s00289-021-03808-5.

[15] Sorokin, V. P.; Bobylev, V. A.; Eselev, A. D. (September 2007). "Epoxy resins based on resorcinol and its derivatives". Polymer Science Series C. 49 (3): 272–275. doi:10.1134/S1811238207030149.

[16] 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

[17] US 11161976, Goodwin, Kimberly; Viswanathan, Ganapathy S. & Peace, Scott et al., "Phenolic epoxy system", published 2021-11-02, assigned to Hexion Vad LLC

[18] Booth, Hubert J (26 July 1973). Synthesis of Epoxy Resins for Property-Structure Studies (Report). OCLC 831523253. DTIC AD0765694.

[19] Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas (July 2023). "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.

[20] Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali (August 2019). "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.

[21] National Toxicology Program (2011). "Diglycidyl resorcinol ether". Report on Carcinogens: Carcinogen Profiles. 12: 163–164. PMID 21852825.

[22] Berdasco, Nancy Anne M.; Waechter, John M. (2012). "Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds". Patty's Toxicology. pp. 491–528. doi:10.1002/0471435139.tox083.pub2. ISBN 978-0-471-31943-6.

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