142-22-3

Basic information

• Product Name: Diallyl 2,2'-oxydiethyl dicarbonate
• Synonyms: 01m;2,5,8,10-Tetraoxatridec-12-enoicacid,9-oxo-,2-propenylester;2,5,8-trioxa-nonanedioicaciddiallylester;5,8,10-tetraoxatridec-12-enoicacid,9-oxo-2-propenylester;allyldiglycerolcarbonate;bis(allylcarbonate)-diethyleneglyco;carbonicacid,allylester,diesterwithdiethyleneglycol;carbonicacid,oxydi-2,1-ethanediyldi-2-propenylester
• CAS NO: 142-22-3
• Molecular Formula: C₁₂H₁₈O₇
• Molecular Weight: 274.27
• EINECS: 205-528-7
• Product Categories: monomer
• Mol File: 142-22-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: −4 °C(lit.)
• Boiling Point: 161 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: liquid
• Density: 1.15 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000105mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Water Solubility: 2.36g/L at 20℃
• Stability: Stability Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Diallyl 2,2'-oxydiethyl dicarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diallyl 2,2'-oxydiethyl dicarbonate(142-22-3)
• EPA Substance Registry System: Diallyl 2,2'-oxydiethyl dicarbonate(142-22-3)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36/37/38-50-38
• Safety Statements: 26-36/37/39-61-37/39-28-7/9
• RIDADR: UN 3237 4.1
• WGK Germany: 2
• RTECS: FG2080000
• Hazardous Substances Data: 142-22-3(Hazardous Substances Data)

Usage

Chemical Properties

liquid

Uses

Transparent organic glass in the manufacture of optical corrective lenses.

Definition

A colorless monomer of diethylene glycol bis(allyl carbonate).

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 6205, 1995 DOI: 10.1021/jo00124a044

InChI:InChI=1/C12H18O7/c1-3-5-16-11(13)18-9-7-15-8-10-19-12(14)17-6-4-2/h3-4H,1-2,5-10H2

Synthetic route

Peroxydikohlensaeure-diethylester (14666-78-5) → 2,5,8-Trioxanonanedioic acid di-2-propenyl ester (142-22-3)

Conditions	Yield
at 40℃; Equilibrium constant; Zersetzung;
at 50℃; Equilibrium constant; Zersetzung;
at 60℃; Equilibrium constant; Zersetzung;

diisopropyl peroxydicarbonate (105-64-6) → 2,5,8-Trioxanonanedioic acid di-2-propenyl ester (142-22-3)

Conditions	Yield
at 40℃; Zersetung;
at 50℃; Zersetung;
at 60℃; Zersetung;

diethylene glycol bischloroformate (106-75-2) + allyl alcohol (107-18-6) → 2,5,8-Trioxanonanedioic acid di-2-propenyl ester (142-22-3)

Conditions	Yield
With calcium carbonate at 50 - 90℃;

Allyl chloroformate (2937-50-0) + diethylene glycol (111-46-6) → 2,5,8-Trioxanonanedioic acid di-2-propenyl ester (142-22-3)

Conditions	Yield
With pyridine
With pyridine

carbon dioxide (124-38-9) + 3-chloroprop-1-ene (107-05-1) + diethylene glycol (111-46-6) → 2,5,8-Trioxanonanedioic acid di-2-propenyl ester (142-22-3)

Conditions	Yield
With 2-cyclohexyl-1,1,3,3-tetramethylguanidine 1.) CH3CN 80 psi, 2.) 80 psi, 55 deg C, 14 h; Yield given. Multistep reaction;

2,5,8-Trioxanonanedioic acid di-2-propenyl ester (142-22-3) → Reaxys ID: 15741496

Conditions	Yield
1,1-bis(tert-hexylperoxy)-3,3,5-trimethycyclohexane at 110 - 130℃; for 4h; Product distribution / selectivity;

Upstream product

• 124-38-9 carbon dioxide 
• 107-05-1 3-chloroprop-1-ene 
• 111-46-6 diethylene glycol 
• 2937-50-0 Allyl chloroformate 
• 106-75-2 diethylene glycol bischloroformate 
• 107-18-6 allyl alcohol 
• 105-64-6 diisopropyl peroxydicarbonate 
• 14666-78-5 Peroxydikohlensaeure-diethylester 

Relevant articles and documents

Replacement of Phosgene with Carbon Dioxide: Synthesis of Alkyl Carbonates

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