106-92-3 Usage
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.
Preparation
In a condensation reaction, epichlorohydrin and allyl alcohol are used in the synthesis of allyl glycidyl ether.
Uses
Different sources of media describe the Uses of 106-92-3 differently. You can refer to the following data:
1. Allyl glycidyl ether is utilized in sealants and adhesives. It is also used in the production of polyvinylcaprolactam.
2. Resin intermediate, stabilizer of chlorinated
compounds, vinyl resins, and rubber.
3. 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.
4. Reactive diluent in epoxy resin
systems; stabilizer of chlorinated compounds;
manufacture of rubber
Chemical Properties
Different sources of media describe the Chemical Properties of 106-92-3 differently. You can refer to the following data:
1. colourless liquid
2. Allyl glycidyl ether is a stable, colorless, flammable liquid with a pleasant odor. It is incompatible
with strong oxidizers agents, acids, and bases. It may form peroxides in storage if
in contact with air.
3. Allyl glycidyl ether is a colorless liquid with a strong, sweet odor
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).
Production Methods
AGE is manufactured through the condensation of allyl
alcohol and epichlorohydrin with subsequent dehydrochlorination
with caustic to form the epoxy ring.
General Description
A colorless liquid with a pleasant odor. Flash point 135°F. Slightly less dense than water and insoluble in water. Hence floats on water. Poisonous by ingestion and mildly toxic by inhalation and skin contact. Very irritating to skin and eyes. Used to make other chemicals.
Air & Water Reactions
Flammable. Insoluble in water.
Reactivity Profile
Allyl glycidyl ether reacts violently with oxidizing agents. Can form peroxides. Polymerizes readily [Handling Chemicals Safely 1980. p.128].
Hazard
Skin, eye, and upper respiratory tract irri-
tant, and dermatitis. Questionable carcinogen.
Health Hazard
Different sources of media describe the Health Hazard of 106-92-3 differently. You can refer to the following data:
1. May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
2. Occupational workers exposed to allyl glycidyl ether develop severe symptoms of poisoning
that include, but are not limited to, irritation of the eyes, redness, pain, blurred vision,
deep skin burns, respiratory system; causes damage of the mucous membranes, dermatitis,
burning sensation, shortness of breath, headache, drowsiness, dullness, nausea, vomiting,
pulmonary edema, narcosis, possible hematopoietic and reproductive effects. Acute
exposure may cause CNS depression. The major target organs include the eyes, skin, respiratory
system, blood, and the reproductive system.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Contact allergens
Allyl glycidyl ether is a monoglycidyl derivative, used
as a reactive epoxy diluent for epoxy resins. As an
impurity, it was considered to be the sensitizing agent
in a plastic industry worker allergic to 3-glycidyloxypropyl
trimethoxysilane, an epoxy silane compound
used as a fixing additive in silicone and polyurethane
Safety Profile
Confirmed animal carcinogen. Poison by ingestion. Moderately toxic by inhalation and skin contact. Mutation data reported. A severe skin and eye irritant. Can cause central nervous system depression and pulmonary edema. A flammable liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical.When heated to decomposition it emits acrid smoke and irritating fumes. See also ALLYL COMPOUNDS
Potential Exposure
Used as a solvent and emulsifier; making epoxy resins, chlorinated compounds; and rubber.
Carcinogenicity
In a 2-year inhalation carcinogenicity
study in Osborne Mendel rats and B6C3F1 mice
(50 of each sex at each exposure level), animals were exposed
to concentrations of 0, 5, or 10 ppm AGE, 6 h/day, 5 days/
week. Although occasional respiratory epithelial tumors
were observed, the NTP concluded the data provided only
equivocal evidence of carcinogenicity in male rats and
female mice. No evidence was obtained to support a carcinogenic
effect in female rats. Some evidence was provided
for a carcinogenic response in male mice, which included
three adenomas of the respiratory epithelium, dysplasia in
four mice, and focal basal cell hyperplasia of the respiratory
epithelium in the nasal passages of seven mice .
Environmental fate
Biological. Bridié et al. (1979) reported BOD and COD values of 0.06 and 1.99 g/g using
filtered effluent from a biological sanitary waste treatment plant. These values were determined
using a standard dilution method at 20 °C for a period of 5 d. The ThOD for allyl glycidyl ether is
2.11 g/g.
Chemical/Physical. Hydrolysis of the epoxide ring is likely forming 1-allyloxy-2,3-
dihydroxypropane (Perez and Osterman-Golkar, 2000).
storage
Allyl glycidyl ether should be kept stored in a cool, dark, fi reproof area separated from
strong oxidants, strong bases, and strong acids.
Shipping
UN2219 Allyl glycidal ether, Hazard Class: 3; Labels: 3-Flammable liquid
Incompatibilities
May form explosive mixture with air. Contact with acids or bases may cause explosive polymerization. Contact with oxidizers or amines may cause fire and explosions.
Waste Disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.
Precautions
During use and/or handling of allyl glycidyl ether, occupational workers should not be
near open flames, sparks, or smoking areas. For temperatures above 48°C, use a closedsystem
ventilation and explosion-proof electrical equipment. Workers should use protective
gloves, protective clothing, and avoid all contact.
Check Digit Verification of cas no
The CAS Registry Mumber 106-92-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 106-92:
(5*1)+(4*0)+(3*6)+(2*9)+(1*2)=43
43 % 10 = 3
So 106-92-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O2/c1-2-3-7-4-6-5-8-6/h2,6H,1,3-5H2/t6-/m1/s1
106-92-3Relevant articles and documents
Synthesis and characterization of a new poly α-amino acid Co(II)-complex supported on magnetite graphene oxide as an efficient heterogeneous magnetically recyclable catalyst for efficient free-coreductant gram-scale epoxidation of olefins with molecular oxygen
Kazemnejadi, Milad,Mahmoudi, Boshra,Sharafi, Zeinab,Nasseri, Mohammad Ali,Allahresani, Ali,Esmaeilpour, Mohsen
, p. 59 - 69 (2019)
A novel magnetic nanocomposite was prepared by immobilization of a cobalt complex of a synthetic poly α-amino acid on Fe3O4-doped graphene oxide (GO/Fe3O4@PAA Co(II)) and was demonstrated to be a highly efficient catalyst for the epoxidation of olefins in mild conditions. PAA was synthesized through a multi-step synthesis, first by a poly condensation reaction of salicylaldehyde followed by the Strecker synthesis. The synthesized nanocomposite was characterized by various analytical and spectroscopic methods including FTIR, ICP, XRD, EDX, XPS, FE-SEM, TEM, TGA, VSM and DLS analyses. A wide variety of olefins could be tolerated toward epoxidation in the presence of molecular oxygen without the need for any co-reductant. The magnetic nanocomposite could be readily separated by a magnet from the mixture and reused for several times without any significant reactivity loss, which represents its potential for practical and industrial application. Also, the scalability of the process was investigated in this work.
-
Byrom,N.T. et al.
, p. 216 - 217 (1976)
-
Rational design 2-hydroxypropylphosphonium salts as cancer cell mitochondria-targeted vectors: Synthesis, structure, and biological properties
Amerhanova, Syumbelya K.,Dimukhametov, Mudaris N.,Gubaidullin, Aidar T.,Islamov, Daut R.,Litvinov, Igor A.,Lyubina, Anna P.,Mironov, Vladimir F.,Nemtarev, Andrey V.,Pashirova, Tatiana N.,Titov, Eugenii A.,Tsepaeva, Olga V.,Voloshina, Alexandra D.
, (2021/11/01)
It has been shown for a wide range of epoxy compounds that their interaction with triphenylphosphonium triflate occurs with a high chemoselectivity and leads to the formation of (2-hydroxypropyl)triphenylphosphonium triflates 3 substituted in the 3-position with an alkoxy, alkylcarboxyl group, or halogen, which were isolated in a high yield. Using the methodology for the disclosure of epichlorohydrin with alcohols in the presence of boron trifluoride ether-ate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium iodides 4 were also obtained. The molecular and supramolec-ular structure of the obtained phosphonium salts was established, and their high antitumor activity was revealed in relation to duodenal adenocarcinoma. The formation of liposomal systems based on phosphonium salt 3 and L-α-phosphatidylcholine (PC) was employed for improving the bioavailabil-ity and reducing the toxicity. They were produced by the thin film rehydration method and exhibited cytotoxic properties. This rational design of phosphonium salts 3 and 4 has promising potential of new vectors for targeted delivery into mitochondria of tumor cells.
Co(II) Schiff base complex decorated on polysalicylaldehyde as an efficient, selective, heterogeneous and reusable catalyst for epoxidation of olefins in mild and self-coreductant conditions
Kazemnejadi, Milad,Shakeri, Alireza,Nikookar, Mahsa,Mohammadi, Mohammad,Esmaeilpour, Mohsen
, p. 6889 - 6910 (2017/10/05)
Abstract: A new Co(II)-Schiff base complex was decorated on a polysalicylaldehyde (PSA) framework and used as a selective and efficient catalyst for the epoxidation of alkenes in the presence of O2 as a green source of oxygen without aco-reductant. The catalyst was characterized step by step by FTIR, UV–Vis, 1H NMR, TGA, CHN, XPS and EDX analyses. Loading an amount of Co ions in the catalyst as well as its leaching amount were studied by an ICP-OES instrument. The catalyst demonstrated excellent activity for the of a variety of alkenes in a mild, inexpensive and efficient protocol. Also, the catalyst can be simply recovered from the reaction mixture and reused for several times without any noteiceable loss in its activity. Reaction parameters including temperature, oxygen flow volume, catalyst amount and solvent were screened by reaction time. Catalytic studies including XPS spectroscopy and some blank experiments were performed to obtain an initial insight into the reaction mechanism. Also, the reactivity of the novel catalyst was evaluated as the turnover frequency. Graphical Abstract: A new and efficient protocol have been developed for the selective epoxidation of olefins using a heterogeneous recyclable Co(II)-Schiff base complex of polysalicylaldehyde in mild and self-coreductant conditions by molecular oxygen.
