3,4-Epoxycyclohexanecarboxylate methyl ester refers to organic compounds with the formula C6H9OCO2CH3. These are bifunctional compounds consisting of an ester and cycloaliphatic epoxide groups. It exists as two diastereomers both of which are chiral. These species are of interest in polymer chemistry.
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Preferred IUPAC name
Methyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate | |
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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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).
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Synthese and reactions
edit3,4-Epoxycyclohexanecarboxylate methyl ester is prepared by epoxidation of 4-cyclohexenecarboxylate methyl ester with peracid.[3] It is a crosslinking agent in the production of epoxy resins.[3][4] 3,4-Epoxycyclohexanecarboxylate methyl ester itself would give a linear polymer when homopolymerized.
Properties
edit3,4-Epoxycyclohexanecarboxylate methyl ester has a viscosity of 6 mPa·s.[3]
References
edit- ^ 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.
- ^ 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.
- ^ a b c Pham, Ha Q.; Marks, Maurice J. (2005). "Epoxy Resins". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_547.pub2. ISBN 9783527303854.
- ^ US 6201070 Naofumi Kumabe filing date 2001-03-13