2386-87-0

Basic information

• Product Name: 3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate
• Synonyms: 3,4-epoxycyclohexanecarboxylicacid(3,4-epoxycyclohexylmethyl)ester;3,4-epoxycyclohexanemethyl3,4-epoxycyclohexanecarboxylate;3,4-epoxycyclohexylmethyl3,4-epoxycyclo-hexaneca;7-oxabicyclo(4.1.0)heptane-3-carboxylicacid,7-oxabicyclo(4.1.0)hept-3-ylmethy;7-Oxabicyclo[4,1,0]heptane-3-carboxylicacid,7-oxabicyclo[4,1,0]hept-3-ylmethylester;chissonox221monomer;erl-4221;ut632
• CAS NO: 2386-87-0
• Molecular Formula: C₁₄H₂₀O₄
• Molecular Weight: 252.31
• EINECS: 219-207-4
• Product Categories: Epoxide Monomers;Monomers;Polymer Science
• Mol File: 2386-87-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: −37 °C(lit.)
• Boiling Point: 355.49°C (rough estimate)
• Flash Point: 245 °F
• Appearance: Pale Yellow to Colorless Liquid
• Density: 1.17 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.8E-05mmHg at 25°C
• Refractive Index: n20/D 1.498(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly)
• PKA: 4.61±0.20(Predicted)
• Water Solubility: 13.85g/L at 20.2℃
• CAS DataBase Reference: 3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate(2386-87-0)
• EPA Substance Registry System: 3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate(2386-87-0)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 1
• RTECS: RN7750000
• Hazardous Substances Data: 2386-87-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale yellow to colorless transparent liquid

Uses

Different sources of media describe the Uses of 2386-87-0 differently. You can refer to the following data:
1. This compound can be made by treatment of the corresponding bis-unsaturated ester with peracetic acid. It is used as a reactive diluent, for filament winding, as an acid scavenger, or as a plasticizer. Vapor hazard is slight at ambient temperature because of its moderately high boiling point. Skin contact is to be avoided.
2. EEC is an epoxy monomer that can be used as a resin in aerospace, electronics and automobile industries as an adhesive and a composite material.

General Description

3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (EEC) is a cycloaliphatic epoxy that can be synthesized by the reaction of 3′-cyclohexenylmethyl 3-cyclohexenecarboxylate with peracetic acid. Its aliphatic backbone and molecular structure provide a number of useful properties such as thermal stability, weatherability, and electrical conductivity.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C14H20O4/c15-14(9-2-4-11-13(6-9)18-11)16-7-8-1-3-10-12(5-8)17-10/h8-13H,1-7H2

Synthetic route

3-cyclohexene-1-carboxylic acid 3-cyclohexen-1-ylmethyl ester (2611-00-9) → 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (2386-87-0)

Conditions	Yield
With phosphotungstic acid; trioctylmethylammonium acetate; phosphoric acid; dihydrogen peroxide; sodium carbonate In water; toluene at 50℃; for 15h; Inert atmosphere;	94%
With 1H-imidazole; tristetrahexylammonium tetrakis(diperoxotungsto) phosphate; dihydrogen peroxide In water; acetonitrile at 49.84℃; under 760.051 Torr; for 24h; Reagent/catalyst; Inert atmosphere;	82%
With dihydrogen peroxide; acetonitrile; triethylamine In water at 60℃; for 10h; Conversion of starting material;	46%

3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (2386-87-0) + carbon dioxide (124-38-9) → C16H20O8

Conditions	Yield
With tetrabutylammomium bromide In neat (no solvent) at 100℃; for 12h; chemoselective reaction;	99%

3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (2386-87-0) + carbon dioxide (124-38-9) → C16H20O8

Conditions	Yield
With calcium iodide In neat (no solvent) at 90℃; under 37503.8 Torr; for 48h; diastereoselective reaction;	98%

3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (2386-87-0) + methacryloyl anhydride (760-93-0) → 3,4-bis(methacryloyloxy)cyclohexanecarboxylic acid 3,4-bis(methacryloyloxy)cyclohexylmethyl ester

Conditions	Yield
With benzyltrimethylammonium chloride; 4-methoxy-phenol at 100℃; for 24h;	81%

4-butanolide (96-48-0) + 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (2386-87-0) → Reaxys ID: 11465227

Conditions	Yield
at 97 - 100℃; for 3h;

3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (2386-87-0) + poly(bisphenol A-co-epichlorohydrin) glycidyl end-capped → [poly(bisphenol A-co-epichlorohydrin) glycidyl end-capped]-(3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate) copolymer

Conditions	Yield
With CD-1012 near-IR femtosecond irradiation;

3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (2386-87-0) + Epon SU-8 → (Epon SU-8)-(3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate) copolymer

Conditions	Yield
With CD-1010 near-IR femtosecond irradiation;

3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (2386-87-0) → poly[7-oxa-bicyclo[4.1.0]heptane-3-carboxylic acid 7-oxa-bicyclo[4.1.0]hept-3-ylmethyl ester], photopolymerization; monomer: UVR 6110

Conditions	Yield
With (4-iPr-phenyl)-4'-methylphenyliodonium (C6F5)4-gallate Kinetics; Further Variations:; Reagents; UV-irradiation;

1,2-propylene cyclic carbonate (108-32-7) + 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (2386-87-0) → Reaxys ID: 11465275

Conditions	Yield
Cr3+ catalyst at 75 - 94℃; for 3h;

Upstream product

• 2611-00-9 3-cyclohexene-1-carboxylic acid 3-cyclohexen-1-ylmethyl ester 

Relevant articles and documents

Safe, environment-friendly and controllable synthetic process of di-epoxide

The invention relates to the field of synthesis of epoxide, and more specifically, relates to a safe, environment-friendly and controllable synthetic process of di-epoxide. The synthetic process of the di-epoxide at least comprises the following steps: mixing diolefin, carboxylic acids, basic salt and solvent, and cooling; dropwise adding a hydrogen peroxide solution for 1-12 h; standing for layering to obtain a lower layer organic phase-1, washing the organic phase-1 with a cleaning solution, and standing for layering to obtain a lower layer organic phase-2; purifying. The reaction system ofthe synthetic process is simple, environmentally friendly, safe and controllable, is low in production cost, and can meet the requirements of technical economy; the prepared di-epoxide is high in purity and yield and low in solvent content, chroma and halogen content, and is suitable for large-scale industrial production.

The method for producing the epoxy compound

PROBLEM TO BE SOLVED: To provide a high-purity epoxy compound.SOLUTION: (1) A method for producing the epoxy compound includes subjecting a compound having a carbon-carbon double bond to an oxidation reaction in the presence of hydrogen peroxide, a quaternary ammonium salt, and polyacids and subsequently removing the quaternary ammonium salt remaining in the reaction mixture by a phenol formaldehyde-based resin. (2) The production method described in (1) uses the phenol formaldehyde-based resin having a phenolic hydroxyl group and an amino group as functional groups.

Highly selective epoxidation of cycloaliphatic alkenes with aqueous hydrogen peroxide catalyzed by [PO4{WO(O2) 2}4]3-/imidazole

In the presence of imidazole as an additive, a phosphorus-containing tetranuclear peroxotungstate, THA3[PO4{WO(O 2)2}4] (I, THA=tetra-n-hexylammonium), could act as an efficient catalyst for epoxidation of cycloaliphatic alkenes with 30% aqueous hydrogen peroxide (H2O2). Compound I showed higher catalytic activity and selectivity to epoxide than other tungstates. By using the I/imidazole system, various kinds of cycloaliphatic alkenes could be highly selectively converted into the acid-sensitive epoxides including industrially important diepoxides in high to excellent yields under the almost stoichiometric conditions. The 1H NMR spectroscopy showed that imidazole would work not only as a proton acceptor but also as a Lewis base to remarkably suppress the acid-catalyzed ring opening of epoxides.