Diglycidyl resorcinol ether

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Diglycidyl resorcinol ether
File:Resorcinol diglycidyl ether.svg
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 Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number
  • 202-987-5
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
KEGG
RTECS number
  • VH1050000
UNII
UN number 2811
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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

[edit | edit source]
  • 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

[edit | edit source]

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

[edit | edit source]

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

[edit | edit source]

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

[edit | edit source]
  1. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  4. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  5. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  6. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  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. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  9. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  10. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  11. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  12. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  13. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  14. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  15. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  16. ^ WO application 2021124125, Zafar, Ashar; Pham, Huynh Tram Anh & Hägg, Katarina et al., "Process for the preparation of a bonding resin", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Stora Enso Oyj 
  17. ^ US 11161976, Goodwin, Kimberly; Viswanathan, Ganapathy S. & Peace, Scott et al., "Phenolic epoxy system", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Hexion Vad LLC 
  18. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  19. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  20. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  21. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  22. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

Further reading

[edit | edit source]
  • Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  • Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  • Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  • Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

External Websites

[edit | edit source]
Retrieved from "http://70.231.62.181/index.php?title=Diglycidyl_resorcinol_ether&oldid=12032667"