Dibenzyl ether
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Dibenzyl ether
structure -
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CAS No:
103-50-4
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Formula:
C14H14O
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Chemical Name:
Dibenzyl ether
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Synonyms:
Benzene,1,1′-[oxybis(methylene)]bis-;Benzyl ether;1,1′-[Oxybis(methylene)]bis[benzene];Benzyl oxide;Dibenzyl ether;Plastikator BA;BA (plasticizer);BA;NSC 5931;[(Benzyloxy)methyl]benzene;(Oxybis(methylene))dibenzene
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CAS No:
Description
Liquid
Dibenzyl ether is a colorless liquid with a mild odor.|Liquid|Colourless liquid, slightly mushroom aroma
Dibenzyl ether is a colorless liquid with a mild odor.|Dibenzyl ether is a benzyl ether in which the oxygen atom is connected to two benzyl groups. It has a role as a metabolite.
Dibenzyl ether Basic Attributes
198.26
198.26
1911156
203-118-2
2O6CNO27RJ
5931
DTXSID5025819
COLORLESS LIQUID|VERY PALE YELLOW
2909309090
Characteristics
9.2
3.3
Clear colorless to pale yellow Liquid
0.99735 g/cm3 @ Temp: 25 °C
3.6 °C
298 °C
275 °F
1.569
H2O: insoluble
Store below +30°C.
1.03X10-3 mm Hg @ 25 deg C
6.84 (NTP, 1992) (Relative to Air)
Oral-Rat LD50: 2500 mg/kg
Heat and open flame are flammable; burning produces irritating smoke; the high concentration of steam itself has an anesthetic effect on people
FAINT, ALMOND ODOR
MUSHROOM TASTE
Liquid molar volume = 0.190344 cu m/kmol
Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. Insoluble in water.
Ethers
Peroxidizable Compound
DIBENZYL ETHER can act as a base to form salts with strong acids and addition complexes with Lewis acids. May react violently with strong oxidizing agents. Burns readily but relatively inert in other reactions, which typically involve the breaking of the carbon-oxygen bond.
Dibenzyl ether|D: Other compounds that may form peroxides|1 samples had 1 ppm peroxide; age >1 yrs; |Kelly
Safety Information
III
9
UN 3082 9/PG 3
2
36/37/38-51/53
23-61
DQ6125000
Xi,N
Treasury is ventilated, low temperature and dry; stored separately from oxidant
Reacts violently with oxidants; may explode on its own
Stable. Combustible. Incompatible with strong acids, strong oxidizing agents.
P273-P304 + P340 + P312-P391-P501
H335-H410
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Dibenzyl ether is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.
This chemical is combustible. (NTP, 1992)
|Warning|H317 (64.41%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, P391, and P501|Aggregated GHS information provided by 2186 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P264, P305+P351+P338, P312, P332+P313, and P337+P313
Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing. Fire Extinguishing Agents: Dry chemical, carbon dioxide (USCG, 1999)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, keep it away from oxidizing materials, and store it at refrigerate temperatures. (NTP, 1992)
Goggles or face shield; rubber gloves (USCG, 1999)
During attempted reductive cleavage of the ether with aluminium dichloride hydride etherate an explosion occurred. Peroxides may have been present in the susceptible ether.
IT WOULD NOT APPEAR THAT DIBENZYL ETHER HAS CAUSED POISONING IN THE FACTORY BUT ITS VOLATILITY...IS RELATIVELY HIGH, & USUAL PROTECTIVE MEASURES MUST BE TAKEN...PROVISION OF GOOD VENTILATION IS MOST IMPORTANT.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.
SEDIMENT: Dibenzyl ether was identified in the Niagara River watershed (Bloody Run Creek) in sediment at a level of 0.5-2 ppm(1).
Toxicity
moderately
Dibenzyl ether's production and use as a synthetic flavoring ingredient(1), a plasticizer for synthetic rubber(2), a plasticizer for nitrocellulose(3) and a solvent in perfumery(3) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1500(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that dibenzyl ether will have slight mobility in soil(SRC). Volatilization of dibenzyl ether is not expected to occur from moist soils, based on an estimated Henry's Law constant of 8.3X10-8 atm-cu m/mol(4) or from dry soils based on an experimental vapor pressure of 1.03X10-3 mm Hg(5). According to a MITI biodegradation test, biodegradation of dibenzyl ether is not expected to be an important fate process in soil(6). However, another study with seawater and river water indicated biodegradation may be rapid(7).|AQUATIC FATE: An estimated Koc value of 1500(SRC), determined from an experimental log Kow(1) and a recommended regression-derived equation(2), indicates that dibenzyl ether would adsorb to suspended solids and sediment(2,SRC) in the water. Dibenzyl ether will be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 8.3X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Experimental BCF values of 171-429 and 187-345(5) suggest that bioconcentrate of dibenzyl ether will be high aquatic organisms(SRC) according to a classification scheme(4). According to a MITI biodegradation test, biodegradation of dibenzyl ether is not expected to be an important fate process in water(5). However, another study with seawater and river water indicated biodegradation may be rapid(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibenzyl ether, which has an experimental vapor pressure of 1.03X10-3 mm Hg at 25 °C(2) will exist as a vapor in the ambient atmosphere. Vapor-phase dibenzyl ether is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 18 hours(3,SRC).
The rate constant for the vapor-phase reaction of dibenzyl ether with photochemically produced hydroxyl radicals has been estimated as 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 18 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).
269.15|An estimated BCF value of 190 was calculated for dibenzyl ether(SRC), using an experimental log Kow of 3.31(1) and a recommended regression-derived equation(2). An 8-week bioconcentration study using carp and dibenzyl ether concentrations of 0.2 mg/l and 0.02 mg/l gave bioconcentration factors of 171-429 and 187-345, respectively(4). According to a classification scheme(3), these experimental BCF values suggest that bioconcentration in aquatic organisms is high(SRC).
The Koc of dibenzyl ether is estimated as approximately 1500(SRC), using an experimental log Kow of 3.31(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that dibenzyl ether has slight mobility in soil(SRC).
The Henry's Law constant for dibenzyl ether is estimated as 8.3X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that dibenzyl ether will be essentially nonvolatile from water surfaces(2,SRC). Dibenzyl ether's vapor pressure, 1.03X10-3 mm Hg(3) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil may not occur(SRC).
DRINKING WATER: Dibenzyl ether was qualitatively identified in Japanese tap water(1).|SURFACE WATER: Dibenzyl ether was identified in the Niagara River watershed at 70 ppm in the 102nd Street Bay area and in Bloody Run Creek water at a level of 0.1-1 ppb(1). Dibenzyl ether was also qualitatively identified in the Niagara River(2). Dibenzyl ether was detected in the River Rhine at three different locations in the Netherlands: Lobith, 0.3 ug/l; Maassluis, 0.01 and 0.1 ug/l; and at Gorinchem, 0.03 ug/l(3).
General and occupational exposure to ethers, such as dibenzyl ether(SRC), can occur through dermal contact, inhalation, and ingestion(1).
Drug Information
4.27 Days
Inhalation may cause nausea because of disagreeable odor. Contact of liquid with eyes causes mild irritation. Prolonged exposure of skin to liquid causes reddening and irritation. Ingestion produces nausea. (USCG, 1999)
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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, immediately transport the victim to a hospital. 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. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
IRRITANT &.../SRP: CNS DEPRESSANT/ IN HIGH CONCN.
dibenzyl ether
Dibenzyl ether Use and Manufacturing
The by-product of the benzyl alcohol hydrolysis from benzyl chloride production, if a concentrated base is used instead of carbonate in this reaction, the yield can be increased to 50% or higher.
spices. Mainly used to prepare mushroom and cherry flavors. Used as a plasticizer for gas chromatography stationary liquid and nitrocellulose, also used in the preparation of spices; used as a medium-level antioxidant, mainly used in the manufacture of sponge rubber products, and also used in the preparation of spices
(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS
GRADE: TECHNICAL
Benzene, 1,1'-[oxybis(methylene)]bis-: ACTIVE|IT PLASTICIZES VINYL RESINS, PARTICULARLY POLYVINYL ACETATE, GIVING FLEXIBLE FILMS...
Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index
Flavoring Agents
Computed Properties
Molecular Weight:198.26
XLogP3:3.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:198.104465066
Monoisotopic Mass:198.104465066
Topological Polar Surface Area:9.2
Heavy Atom Count:15
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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