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

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

Uses

Used in Aerospace Industry:
3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is used as a resin for [application reason] in the aerospace industry. Its thermal stability, weatherability, and electrical conductivity make it a suitable choice for this application.
Used in Electronics Industry:
3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is used as an adhesive and a composite material for [application reason] in the electronics industry. Its properties of thermal stability and electrical conductivity contribute to its effectiveness in this field.
Used in Automobile Industry:
3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is used as a resin in the automobile industry for [application reason]. Its combination of thermal stability, weatherability, and electrical conductivity makes it an ideal material for various automotive applications.
Used as a Reactive Diluent:
3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is used as a reactive diluent for [application reason]. Its properties allow it to be an effective component in the formulation of various products.
Used for Filament Winding:
3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is used in filament winding as a [application type] for [application reason]. Its characteristics make it suitable for this specific application.
Used as an Acid Scavenger:
3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is used as an acid scavenger for [application reason]. Its ability to neutralize acids makes it a valuable component in certain industrial processes.
Used as a Plasticizer:
3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is used as a plasticizer for [application reason]. Its properties enhance the flexibility and workability of certain materials.
Safety Note:
Vapor hazard is slight at ambient temperature due to its moderately high boiling point. However, skin contact should be avoided to ensure safety during handling and use.

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.

PROCESS FOR THE EPOXIDATION OF OLEFINS

The subject invention is related to a process for the epoxidation of olefin with peroxide, comprising reacting peroxide with olefin in the presence a solvent, wherein the solvent has Hansen Solubility Parameters (HSPs) of δT,solvent and δH,solvent and the epoxide product has Hansen Solubility Parameters (HSPs) of δT,product and δH,product, and wherein: [in-line-formulae]δT,product?6≦δT,solvent≦δT,product+6, and[/in-line-formulae] [in-line-formulae]δH,product?6≦δH,solvent.[/in-line-formulae]

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.

The method for producing the epoxy compound

PROBLEM TO BE SOLVED: To provide a process for producing an alicyclic epoxy compound using hydrogen peroxide, which efficiently gives polyfunctional epoxy resins, to provide a curable resin composition containing an epoxy resin obtained by the production process for the epoxy resins, and to provide cured products thereof. SOLUTION: There is provided the epoxidation method including an oxidizing reaction of carbon-carbon double bonds using hydrogen peroxide, in which at least two kinds of tungstic acids, phosphoric acid (or a phosphate), a quaternary ammonium salt having ≥16 carbon atoms in total, and an aqueous hydrogen peroxide solution are essentially used. COPYRIGHT: (C)2011,JPOandINPIT

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.

PROCESS FOR PRODUCING EPOXY COMPOUND

According to the present, invention, a process for producing an epoxy compound, where an epoxy compound can be selectively produced from olefins with good yield at low cost in a safe manner by a simple operation under mild conditions without using a quaternary ammonium salt or a metal compound, is provided. The present invention relates to a process for producing an epoxy compound, comprising epoxidizing a carbon-carbon double bond of an organic compound having a carbon-carbon double bond by using hydrogen peroxide as an oxidant, wherein the epoxidation is carried by out using an organic nitrile compound and an organic amine compound.

PROCESS FOR PRODUCING EPOXIDES FROM OLEFINIC COMPOUNDS

A process for producing an epoxide such as a cycloaliphatic diepoxide by the reaction of an olefin such as a cycloaliphatic diene with hydrogen peroxide (H2O2) as an oxidant in the presence of a catalytic system under pH control for example at a pH of less than about 5. The present invention is advantageously used for the epoxidation of olefinic compounds such as olefins and aliphatic or aromatic dienes.