Allyl glycidyl ether

Base Information

• Chemical Name: Allyl glycidyl ether
• CAS No.: 106-92-3
• Deprecated CAS: 112186-06-8,90907-93-0,90907-93-0
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• Hs Code.: 29109000
• European Community (EC) Number: 203-442-4
• ICSC Number: 0096
• NSC Number: 18596,631
• UN Number: 2219
• UNII: HDC0791894
• DSSTox Substance ID: DTXSID9039232
• Nikkaji Number: J34.520B
• Wikipedia: Allyl_glycidyl_ether
• Wikidata: Q2467070
• ChEMBL ID: CHEMBL1528174
• Mol file: 106-92-3.mol

Synonyms:Oxirane,[(2-propenyloxy)methyl]- (9CI);Propane, 1-(allyloxy)-2,3-epoxy- (6CI,8CI);1,2-Epoxy-3-allyloxypropane;1-(2-Propenyloxy)-2,3-epoxypropane;1-Allyloxy-2,3-epoxypropane;2-(Allyloxymethyl)oxirane;2-[[(2-Propenyl)oxy]methyl]oxirane;AGE;Allyl 2,3-epoxypropyl ether;Allyl oxiranemethyl ether;Denacol EX 111;Glycidyl2-propenyl ether;Glycidyl allyl ether;NSC 18596;NSC 631;[(2-Propenyloxy)methyl]oxirane;[(Allyloxy)methyl]oxirane;

Chemical Property of Allyl glycidyl ether

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 4.7 mm Hg ( 25 °C)
• Melting Point: -100 °C
• Refractive Index: n20/D 1.433(lit.)
• Boiling Point: 153.2 °C at 760 mmHg
• Flash Point: 57.2 °C
• PSA: 21.76000
• Density: 0.962 g/cm³
• LogP: 0.58780
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: 50 g/L (20°C)
• Water Solubility.: 50 g/L (20 ºC)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 114.068079557
• Heavy Atom Count: 8
• Complexity: 80.6
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Allyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-20/22-37/38-40-41-43-52/53-62-68
• Safety Statements: 24/25-26-36/37/39-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Glycidyl Ethers
• Canonical SMILES: C=CCOCC1CO1
• Recent ClinicalTrials: The Effect of Aged Garlic Extract Supplementation on Immune System
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: Corrosive. The substance is corrosive to the eyes, skin and respiratory tract. Inhalation of the vapour may cause lung oedema. Exposure could cause central nervous system depression. Exposure could cause lowering of consciousness. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization. May cause genetic damage in humans. Animal tests show that this substance possibly causes toxicity to human reproduction or development. This substance is possibly carcinogenic to humans.
• Description: Allyl glycidyl ether is a colorless liquid clycidyl ether with a pleasant odor. The compound is insoluble in water and less dense than water, therefore can easily float on water. When ingested or inhaled, allyl glycidyl ether is mildly toxic. It is not classified as a human carcinogen.
• Uses: Allyl glycidyl ether is utilized in sealants and adhesives. It is also used in the production of polyvinylcaprolactam. Resin intermediate, stabilizer of chlorinated compounds, vinyl resins, and rubber. Allyl glycidyl ether is a monoglycidyl derivative, used as a reactive epoxy diluent for epoxy resins. As an impurity, it was considered as the sensitizing agent in a plastic industry worker allergic to 3-glycidyloxypropyltrimethoxysilane, an epoxy silane compound used as a fixing additive in silicone and polyurethane. Reactive diluent in epoxy resin systems; stabilizer of chlorinated compounds; manufacture of rubber
• Physical properties: Clear, colorless, watery, combustible liquid with a strong, pleasant odor. An odor threshold value of 47 mg/m3 was reported (quoted, Verschueren, 1983).

Technology Process of Allyl glycidyl ether

There total 10 articles about Allyl glycidyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.17%

allyl alcohol (107-18-6) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → Allyl glycidyl ether (106-92-3,25639-25-2,90907-93-0)

Guidance literature:

allyl alcohol; epichlorohydrin; With trifluorormethanesulfonic acid; sulfuric acid; at 45 - 55 ℃; for 5h; Molecular sieve;

With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; at 40 - 45 ℃; for 3h; Reagent/catalyst; Temperature;

Reference yield: 83.0%

Allyl ether (557-40-4) → Allyl glycidyl ether (106-92-3,25639-25-2,90907-93-0)

Guidance literature:

With oxygen; In acetonitrile; at 60 ℃; for 3h; under 760.051 Torr; chemoselective reaction; Catalytic behavior;

DOI:10.1007/s11164-017-3027-z

Reference yield: 82.0%

3-allyloxy-1-chloro-2-propanol (4638-03-3) → Allyl glycidyl ether (106-92-3,25639-25-2,90907-93-0)

Guidance literature:

With sodium hydroxide; In diethyl ether; at 0 - 20 ℃; for 8h;

DOI:10.3390/molecules26216350

upstream raw materials:

peracetic acid

Allyl ether

allyl alcohol

epichlorohydrin

Downstream raw materials:

phenyl thiocyanate

2-[3-(4-methoxy-phenyl)-2-thiocyanato-propoxymethyl]-oxirane

phenyl isothiocyanate

4-(2-propenyloxymethyl)-2-(p-chlorophenyl)-1,3-dioxolane

Refernces

• 1、 Jungk, Steven John,Moore, Jane Ann,Gandour, Richard David. "Efficient Synthesis of C-Pivot Lariat Ethers. 2-(Alkoxymethyl)-1,4,7,10,13,16-hexaoxacyclooctadecanes". . p. 1116 - 1120. Retrieved 1983.
• 2、 Wu, Peng,Liu, Yueming,He, Minyuan,Tatsumi, Takashi. "A novel titanosilicate with MWW structure Catalytic properties in selective epoxidation of diallyl ether with hydrogen peroxide". . p. 183 - 191. Retrieved 2004.
• 3、 Cleveland, Alexander H.,Fronczek, Frank R.,Kartika, Rendy. "Synthesis of Vicinal Dichlorides via Activation of Aliphatic Terminal Epoxides with Triphosgene and Pyridine". . p. 3367 - 3377. Retrieved 2018/03/26.