3,4-Epoxycyclohexanecarboxylate methyl ester

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3,4-Epoxycyclohexanecarboxylate methyl ester
3,4-Epoxycyclohexancarboxylatmethylester.svg
Names
Preferred IUPAC name
Methyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C8H12O3/c1-10-8(9)5-2-3-6-7(4-5)11-6/h5-7H,2-4H2,1H3
    Key: QCGKUFZYSPBMAY-UHFFFAOYSA-N
  • COC(=O)C1CCC2C(C1)O2
Properties
C8H12O3
Molar mass 156.181 g·mol−1
Appearance Colorless liquid[1]
Boiling point 109.5–110.5 °C (229.1–230.9 °F; 382.6–383.6 K)[2] (17 mmHg)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3,4-Epoxycyclohexanecarboxylate methyl ester is a cycloaliphatic epoxide, which is added as monovalent monomer to other monomers for the production of crosslinked epoxy resins.[3][4] 3,4-Epoxycyclohexanecarboxylate methyl ester itself would give a linear polymer when homopolymerized.

Production[]

3,4-Epoxycyclohexanecarboxylate methyl ester is prepared by epoxidation of 4-cyclohexenecarboxylate methyl ester with peracid.[3]

Properties[]

3,4-Epoxycyclohexanecarboxylate methyl ester has a viscosity of 6 mPa·s.[3]

References[]

  1. ^ James V. Crivello, Ulrike Varlemann (October 1995). "Mechanistic study of the reactivity of 3,4-epoxycyclohexylmethyl 3′,4′-epoxycyclohexancarboxylate in photoinitiated cationic polymerizations". Journal of Polymer Science Part A: Polymer Chemistry. 33 (14): 2473–2486. doi:10.1002/pola.1995.080331421.
  2. ^ NORMAN A. NELSON , GEORGE A. MORTIMER (October 1957). "Bicyclo[3.1.0]hexane Derivatives. I. Synthesis of Bicyclo[3.1.0]-2-hexanone and Methyl Bicyclo[3.1.0]hexane-1-carboxylate". The Journal of Organic Chemistry. 22 (10): 1146–1153. doi:10.1021/jo01361a003.
  3. ^ a b c Pham, Ha Q.; Marks, Maurice J. "Epoxy Resins". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_547.pub2.
  4. ^ US 6201070  "METHOD FOR ENHANCING THE TOUGHNESS OF CYCLOALIPHATIC EPOXIDE-BASED COATINGS."
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