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Home > Encyclopedia > Allyl glycidyl ether

Allyl glycidyl ether

Allyl glycidyl ether structure

Allyl glycidyl ether 

structure
  • CAS No:

    106-92-3

  • Formula:

    C6H10O2

  • Chemical Name:

    Allyl glycidyl ether

  • Synonyms:

    Oxirane,2-[(2-propen-1-yloxy)methyl]-;Propane,1-(allyloxy)-2,3-epoxy-;Oxirane,[(2-propenyloxy)methyl]-;2-[(2-Propen-1-yloxy)methyl]oxirane;Allyl 2,3-epoxypropyl ether;Allyl glycidyl ether;Glycidyl allyl ether;1,2-Epoxy-3-allyloxypropane;1-Allyloxy-2,3-epoxypropane;[(Allyloxy)methyl]oxirane;Glycidyl 2-propenyl ether;Allyl oxiranemethyl ether;(±)-Allyl glycidyl ether;[(2-Propenyloxy)methyl]oxirane;Denacol EX 111;AGE;NSC 18596;NSC 631;1-(2-Propenyloxy)-2,3-epoxypropane;A 32608;2-[(2-Propenyloxy)methyl]oxirane;2-(Allyloxymethyl)oxirane;2-[(Prop-2-en-1-yloxy)methyl]oxirane;AGE 500;Silong 191;2-(Prop-2-enoxymethyl)oxirane;112186-06-8;90907-93-0

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Colorless liquid with a pleasant odor.


Allyl glycidyl ether appears as a colorless liquid with a pleasant odor. 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.|DryPowder; Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|Colorless liquid with a pleasant odor.


Allyl glycidyl ether appears as a colorless liquid with a pleasant odor. 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.

Allyl glycidyl ether Basic Attributes

114.14

114.14

105871

203-442-4

0096

18596|631

2219

DTXSID9039232

COLORLESS LIQUID|Colorless liquid ...

29109000

Characteristics

21.8

0.78

Clear colorless Liquid

0.9698 g/cm3 @ Temp: 20 °C

-100 °C

153.9 °C @ Press: 760 Torr

135 °F

1.444

H2O: 50 g/L (20 ºC)

Refrigerator (+4°C)

4.7 mm Hg ( 25 °C)

3.9 (vs air)

Oral-rat LD50: 1600 mg/kg; Oral-Mouse LD50: 390 mg/kg

Flammable; spicy and irritating smoke is released from the fire

Explosive limits , vol% in air: see Notes

CHARACTERISTIC, NOT UNPLEASANT ODOR

Flammable. Insoluble in water.

Ethers

Polymerizable

ALLYL GLYCIDYL ETHER reacts violently with oxidizing agents. Can form peroxides. Polymerizes readily [Handling Chemicals Safely 1980. p.128].

1-Allyloxy-2,3-epoxypropane|B*: Compounds that form peroxides on concentration (distillation/evaporation)|Bretherick's|Detonation during distillation despite negative peroxide test result (some chemicals may require multiple testing methods). See Bretherick's.

264 °C

Class II Combustible Liquid: Fl.P. at or above 100°F and below 140°F.

Safety Information

III

3

UN 2219 3/PG 3

3

10-20/22-37/38-40-41-43-52/53-62-68

24/25-26-36/37/39-61

RR0875000

Xn

Treasury is ventilated, low temperature and dry; stored and transported separately from oxidant

Steam and air can be explosive when mixed

Stable. Combustible. Incompatible with strong oxidizing agents, acids, bases. May form peroxides in storage if in contact with air.

P261-P273-P280-P305 + P351 + P338

H226-H302-H315-H317-H318-H332-H335-H341-H351-H361f-H412

Strong oxidizers.

DHHS/NTP; Toxicology & Carcinogenesis Studies of Allyl glycidyl ether in Osborne-Mendel Rats and B6C3F1 Mice (Inhalation Studies) Technical Report Series No. 376 (1990) NIH Publication No. 90-2831

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Flammable. Above 48 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree, Reactive - 1st degree

|Danger|H226: Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P333+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P321, P330, P332+P313, P333+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 352 companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P280, P281, P284, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P314, P320, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P311, P312, P314, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam. Do not use dry chemical extinguishers to control fires involving nitromethane (UN1261) or nitroethane (UN2842). LARGE FIRE: Water spray, fog or alcohol-resistant foam. Do not use straight streams. Move containers from fire area if you can do it without risk. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016)|Use powder, foam, carbon dioxide, water. In case of fire: keep drums, etc., cool by spraying with water.

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. (NIOSH, 2016)|Workers should be provided with and required to use chemical protective clothing, gloves, face shields (8 inch minimum), and other appropriate protective clothing necessary to prevent skin contact with allyl glycidyl ether. ... Use splash-proof safety goggles where allyl glycidyl ether may come in contact with the eyes.|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|For more Personal Protective Equipment (PPE) (Complete) data for ALLYL GLYCIDYL ETHER (7 total), please visit the HSDB record page.|(See protection codes)

Explosive limits , vol% in air:

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Clothing which becomes contaminated with allyl glycidyl ether should removed immediately and placed in closed containers for storage until it can be discarded or until provision is made for removal of alllyl glycidyl ether from clothing. If the clothing is to be laundered or cleaned, the person performing the operation should be informed of allyl glycidyl ether's hazardous properties.|Where there is any possibility of a worker's eyes being exposed to AGE, an eye-wash fountain should be provided within the immediate work area for emergency use. ...|Where there is any possibility of a worker's body being exposed to AGE, facilities for quick drenching of the body should be provided within the immediate work area for emergency use. ...|For more Preventive Measures (Complete) data for ALLYL GLYCIDYL ETHER (6 total), please visit the HSDB record page.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Fire or Explosion: 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Health: 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.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for ALLYL GLYCIDYL ETHER (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Skin and eye irritant.|/Glycidyl ethers/ are primary skin & eye irritants. ... /Glycidyl ethers/|Dermal contact is the usual mode of exposure, but droplets in mist can also attack the eyes and respiratory tract. Glycidyl & diglycidyl ethers tend to be irritants and sensitizing agents. /Glycidyl & diglycidyl ethers/

Permissible Exposure Limit: Table Z-1 Ceiling value: 10 ppm (45 mg/cu m).|Vacated 1989 OSHA PEL TWA 5 ppm (22 mg/cu m); STEL 10 ppm (44 mg/cu m) is still enforced in some states.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 5 ppm (22 mg/cu m).|Recommended Exposure Limit: 15 Min Short-Term Exposure Limit: 10 ppm (44 mg/cu m). Skin.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in inert absorbent. Wash away remainder with plenty of water. Store and dispose of according to local regulations. Do NOT let this chemical enter the environment.

Fireproof. Separated from strong oxidants, strong bases and strong acids. Cool. Keep in the dark.

A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.

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.

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.

NO open flames, NO sparks and NO smoking. Above 48 °C use a closed system, ventilation and explosion-proof electrical equipment.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield, safety goggles or eye protection in combination with breathing protection.

Toxicity

highly toxic

LD50 Rabbit percutaneous 2.55 g/kg|LC50 Mouse inhalation 270 ppm/4 hours|LC50 Rat inhalation 670 ppm/8 hr|LD50 Mouse intragastric 0.39 g/kg|LD50 Rat intragastric 1.60 g/kg

Toxicology and carcinogenesis studies were conducted by exposing groups of 50 Osborne-Mendel rats and B6C3F1 mice of each sex to allyl glycidyl ether (greater than 97% pure) by inhalation for 6 hr/day, 5 days/wk for ... 2 yr. ... Under the conditions of these 2 yr inhalation studies, there was equivocal evidence of carcinogenic activity of allyl glycidyl ether for male Osborne-Mendel rats, based on the presence of one papillary adenoma of respiratory epithelial origin, one squamous cell carcinoma of the respiratory epithelial origin, and one poorly differentiated adenocarcinoma of olfactory epithelial origin, all occurring in the nasal passage of males exposed to 10 ppb. There was no evidence of carcinogenic activity of allyl glycidyl ether for female rats. One papillary adenoma of the respiratory epithelium was present in a female rat exposed to 5 ppm. There was some evidence of carcinogenic activity of allyl glycidyl ether for male B6C3F1 mice based on the presence of three adenomas of the respiratory epithelium, dysplasia in four males, and focal basal cell hyperplasia of the respiratory epithelium in seven males in the nasal passage of mice exposed to 10 ppm. There was equivocal evidence of carcinogenic activity of allyl glycidyl ether for female mice, based on the presence of one adenoma of the respiratory epithelium and focal basal cell hyperplasia of the respiratory epithelium in seven females exposed to 10 ppm. The sensitivity of the assay to detect potential carcinogenicity may have been reduced in male rats because of poor survival in all groups.

Drug Information

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: 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. (ERG, 2016)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)|(See procedures)


Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

SEVERAL CASES OF DERMATITIS AND 1 CASE OF EYE IRRITATION CONSTITUTE THE HUMAN DATA.|Allyl glycidyl ether is a CNS depressant and also causes acute pulmonary edema. It is classified as slightly toxic after oral administration and percutaneous application, appreciably irritating and injurious to the eyes and skin, capable of causing skin sensitization in human subjects ... .|Short-term (acute): Exposure to AGE can cause moderate irritation of the skin and severe irritation of the eyes and respiratory tract. Long-term (chronic): Exposure to AGE can cause dermatitis with itching, swelling, and blisters. Skin sensitization to AGE and cross sensitization with other epoxy agents can also occur.|Dermal contact is the usual mode of exposure, but droplets in mist can also attack the eyes and respiratory tract. Glycidyl & diglycidyl ethers tend to be irritants and sensitizing agents. /Glycidyl & diglycidyl ethers/

allyl glycidyl ether

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact

irritation eyes, skin, nose, respiratory system; dermatitis; pulmonary edema; narcosis; possible hematopoietic, reproductive effects


Cough. Sore throat. Burning sensation. Drowsiness. Lethargy.


MAY BE ABSORBED! Dry skin. Redness. Pain. Blisters.


Redness. Pain. Blurred vision. Severe deep burns.

Eyes, skin, respiratory system, blood, reproductive system

Allyl glycidyl ether Use and Manufacturing

Methods of Manufacturing

... MANUFACTURED THROUGH THE CONDENSATION OF ALLYL ALCOHOL & EPICHLOROHYDRIN WITH SUBSEQUENT DEHYDROCHLORINATION WITH CAUSTIC TO FORM THE EPOXY RING.

Uses

The molecule contains both carbon-carbon double bonds and epoxy bonds, and is an important polymerized monomer and organic synthesis intermediate.


Adhesives and sealant chemicals


Electrical and electronic products

Production

1,000,000 - 10,000,000 lb

All other basic organic chemical manufacturing|Oxirane, 2-[(2-propen-1-yloxy)methyl]-: ACTIVE|TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.|IT IS NOT CLASSIFIED AS DANGEROUS ARTICLE AND IS NOT REGULATED BY THE BUREAU OF EXPLOSIVES.

SAMPLING AND ANALYTICAL METHODS WERE DEVELOPED FOR 130 SUBSTANCES INCLUDING ALLYL GLYCIDYL ETHER.|THE HYDROCHLORIC ACID-DIOXANE METHOD FOR EPOXY GROUPS OR GLC IS SUGGESTED FOR DETERMINATION IN ATMOSPHERE.|PHOTOMETRIC DETERMINATION OF ALLYL GLYCIDYL ETHER IN AIR. SENSITIVITY IS 1-5 MG/5 ML OF AIR.|NIOSH Method S346. Analyte: Allyl glycidyl ether. Matrix: Air. Procedure: Gas chromatography flame ionization detection. Method Evaluation: Method was validated over the range of 19 to 87 mg/cu m using a 3 liter sample. Precision (CVt): 0.057.|Solid sorbent sampling and chromatographic determination of glycidyl ethers in air.

Fire Hazards -> Flammable - 2nd degree, Reactive - 1st degree

Computed Properties

Molecular Weight:114.14
XLogP3:0.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:114.068079557
Monoisotopic Mass:114.068079557
Topological Polar Surface Area:21.8
Heavy Atom Count:8
Complexity:80.6
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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