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Diphenyl ether

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Diphenyl ether Basic information
Product Name:Diphenyl ether
Synonyms:AKOS BBS-00004250;AKOS 90362;FEMA 3667;DIPHENYL OXIDE;DIPHENYL ETHER;DEPHENYL OXIDE;biphenyloxide;Chemcryl JK-EB
CAS:101-84-8
MF:C12H10O
MW:170.21
EINECS:202-981-2
Product Categories:Pyridines ,Halogenated Heterocycles;FINE Chemical & INTERMEDIATES;Pharmaceutical Intermediates;Organics;Biphenyl & Diphenyl ether;DIG-DY;Bioactive Small Molecules;Building Blocks;C11 to C12;Cell Biology;Chemical Synthesis;Ethers;Organic Building Blocks;Oxygen Compounds;Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;101-84-8
Mol File:101-84-8.mol
Diphenyl ether Structure
Diphenyl ether Chemical Properties
Melting point 26 °C
Boiling point 259 °C(lit.)
density 1.073 g/mL at 25 °C(lit.)
vapor density >5.86 (25 °C, vs air)
vapor pressure <1 mm Hg ( 20 °C)
refractive index n20/D 1.579(lit.)
FEMA 3667 | DIPHENYL ETHER
Fp >230 °F
storage temp. Store below +30°C.
solubility alcohol: soluble(lit.)
form Colorless liquid
color White or Colorless to Almost white or Almost colorless
Specific Gravity1.073
Relative polarity2.8
OdorWeak geranium.
explosive limit0.8-1.5%(V)
Odor Threshold0.1ppm
Odor Typegreen
biological sourcesynthetic
Water Solubility insoluble
FreezingPoint 27℃
Merck 14,7288
JECFA Number1255
BRN 1364620
Henry's Law Constant2.13 at 20 °C (approximate - calculated from water solubility and vapor pressure)
Exposure limitsNIOSH REL: TWA 1 ppm (7 mg/m3), IDLH 100 ppm; OSHA PEL: TWA 1 ppm; ACGIH TLV: TWA 0.1, STEL 2 ppm (adopted).
Dielectric constant3.7(30℃)
InChIKeyUSIUVYZYUHIAEV-UHFFFAOYSA-N
LogP4.21 at 25℃
CAS DataBase Reference101-84-8(CAS DataBase Reference)
NIST Chemistry ReferenceDiphenyl ether(101-84-8)
EPA Substance Registry SystemPhenyl ether (101-84-8)
Safety Information
Hazard Codes N,Xi,T
Risk Statements 51/53-36/37/38-39/23/24/25-23/24/25-36/38-36
Safety Statements 60-61-57-37/39-26-45-36/37
RIDADR UN 3077 9/PG 3
OEBB
OELTWA: 1 ppm (7 mg/m3)
WGK Germany 2
RTECS KN8970000
Autoignition Temperature610 °C
TSCA Yes
HS Code 2909 30 10
HazardClass 9
PackingGroup III
Hazardous Substances Data101-84-8(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 2450 mg/kg LD50 dermal Rabbit > 7940 mg/kg
IDLA100 ppm
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Diphenyl ether Usage And Synthesis
DescriptionDiphenyl ether (diphenyl oxide) is a colorless liquid with a floral odor. It is a white, crystalline solid at temperatures below 80ºF (27ºC). It has low volatility, low solubility in water, and is stable at high temperatures. Avoid contact with oxidizing materials.
Liquid diphenyl oxide is used primarily in industry. It is used in the industrial setting as a heat transfer fluid. It is the major component of Dowtherm A® (an eutectic mixture of phenyl ether and biphenyl) and further as a chemical intermediate in the production of surface-active agents and hightemperature lubricants, and in perfumery due to its geranium-like odour (ACG99b). It is also used as a chemical intermediate in the manufacture of surfactants and fire retardants.
Diphenyl oxide (DPO) is manufactured using the direct phenol method.
synthesis of diphenyl ether
Physical propertiesDiphenyl oxide is a practically colorless crystalline solid with a harsh, floral-green, metallic geranium-type odor. clear pale yellowish liquid after melting. It is almost completely insoluble in water, but dissolves in most of the common organic solvents. Its high thermal stability at temperatures as high as 350 to 400°C. together with its noncorrosiveness and general chemical inertness make it eminently suitable as a component of high-boiling heat transfer media.
Chemical PropertiesDiphenyl Ether has not been observed in nature. It is a colorless liquid or a crystalline solid (mp 26.8°C) with an odor reminiscent of geranium leaves. Diphenyl ether is obtained as a by-product in the production of phenol by high-pressure hydrolysis of chlorobenzene. Because of its stability and low price, diphenyl ether is used in large quantities in soap perfumes.
OccurrenceReported found in muscat grapes, grilled beef, green tea, potato chips, buckwheat, Bourbon vanilla and lemon balm.
UsesPhenyl Ether is an Impurity of Propofol (P829750).
UsesDiphenyl ether is widely used as a heat transfer agent and a dye carrier. It can be used alone or as a mixture with other materials. Because of its reactivity, It can also be used as a raw material or chemical intermediate to produce commercial products. Diphenyl ether is used in the production of:
  1. Diphenyl ether is employed as a processing aid in the production of polyesters. It acts as a chemical intermediate in the production of surface active agents and high temperature lubricants, fire retardants like polybrominated diphenyl ethers (PBDEs) and fragrance for detergents.
  2. Heat transfer media – like DOWTHERMTM fluids used for heating industrial processes
  3. Alkylated diphenyl oxides – used to make surfactants, greases and lubricants
  4. Halogenated diphenyl oxides – used in insecticides, wood preservatives, and flame retardants for appliance casings in consumer electronic products
  5. High temperature solvents
  6. Coatings
  7. Textile dye labeling
  8. Plastics – like ethylene-propylene-diene monomer (EPDM) rubber that is used for membrane roofing materials
  9. Diphenyl ether plays a vital role in the Ferrario reaction to produce phenoxathiin, which finds application in polyamide and polyimide production. Involving similar reactions, diphenyl ether is a significant side product in the high-pressure hydrolysis of chlorobenzene in the production of phenol.
  10. Diphenyl ether is found in alcoholic beverages. Diphenyl ether is present in muscat grapes, green tea, vanilla, lemon balm, buckwheat, potato chips and grilled beef. Diphenyl ether is a flavouring ingredient.
DefinitionChEBI: Diphenyl ether is an aromatic ether in which the oxygen is attached to two phenyl substituents. It has been found in muscat grapes and vanilla. It has a role as a plant metabolite.
PreparationBy heating potassium phenolate with bromobenzene or with chlorobenzene at elevated temperatures.
Aroma threshold valuesAroma characteristics at 1.0%: grassy, musty, powdery, dry, terpy, ocimenelike, aromatic and hoplike with green juniper berry nuances.
Taste threshold valuesTaste characteristics at 10 ppm: dry chemical, floral rosey with carrot, tropical and hoplike terpy notes and a green vegetative and woody nuance.
Synthesis Reference(s)Synthetic Communications, 13, p. 335, 1983 DOI: 10.1080/00397918308066985
Synthesis, p. 204, 1991 DOI: 10.1055/s-1991-26419
General DescriptionDiphenyl ether occurs, e.g., in lemon balm oil. The compound forms colorless crystals that possess a geranium-like aroma. Diphenyl ether is formed as a byproduct in the high-pressure hydrolysis of chlorobenzene. Because of its high thermal stability, a eutectic mixture of diphenyl ether and biphenyl is employed as a heat transfer medium. Diphenyl ether is the starting material for organic intermediates and is used as a fragrance component. The compound is also employed as a processing aid in the production of polyesters; several polybromine derivatives of diphenyl ether are used as fire retardants.
General DescriptionColorless liquid with a mild pleasant odor. May float or sink in water. Freezing point is 81°F.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileDiphenyl oxide can react with oxidizing materials. . A vigorous reaction occurred between the ether and chlorosulfuric acid.
Health HazardInhalation 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.
Fire HazardDiphenyl oxide is combustible.
Flammability and ExplosibilityNon flammable
Safety ProfileModerately toxic by ingestion. Prolonged exposure damages liver, spleen, kidneys, and thyroid, and upsets gastrointestinal tract. A skin and eye irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. For explosion hazard, see ETHERS. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes
Potential ExposureStrong oxidizers may cause fire andexplosions. Attacks some plastics, rubber, and coatings.
First aidWear protective gloves andclothing to prevent any reasonable probability of skin contact. Safety equipment suppliers/manufacturers can providerecommendations on the most protective glove/clothingmaterial for your operation. All protective clothing (suits,gloves, footwear, headgear) should be clean, available eachday, and put on before work. Contact lenses should not beworn when working with this chemical. Wear splash-proofgoggles and face shield if working with the liquid or dustproof chemical goggles and face shield if working with thecrystalline material, unless full face-piece respiratory protection is worn. Employees should wash immediately withsoap when skin is wet or contaminated. Provide emergencyshowers and eyewash.Respirator Selection: 2
CarcinogenicityPhenyl ether was not mutagenic in the Ames Salmonella assay with or without metabolic activation.
storageColor Code—Green: General storage may be used.Prior to working with diphenyl oxide you should be trainedon its proper handling and storage. Before entering confinedspace where this chemical may be present, check to makesure that an explosive concentration does not exist. Store intightly closed containers in a cool, well-ventilated areaaway from oxidizers. Store in tightly closed containers in acool, well-ventilated area away from heat. Sources of ignition, such as smoking and open flames, are prohibitedwhere this chemical is used, handled, or stored in a mannerthat could create a potential fire or explosion hazard. Metalcontainers involving the transfer of 5 gallons or more ofthis chemical should be grounded and bonded. Drums mustbe equipped with self-closing valves, pressure vacuumbungs, and flame arresters. Use only nonsparking tools andequipment, especially when opening and closing containersof this chemical.
ShippingThe name of this material is not in the DOT listof materials for label and packaging standards. However,based on regulations, it may be classified as anEnvironmentally hazardous substances, solid, n.o.s. Thischemical requires a shipping label of “CLASS 9.” It falls inHazard Class 9 and Packing Group III.[20,
Purification MethodsCrystallise the ether from 90% EtOH. Melt it, wash it with 3M NaOH and water, dry it with CaCl2 and fractionally distil it under reduced pressure. Fractionally recrystallise it from its melt and store over P2O5. [Beilstein 6 IV 562.]
Toxics Screening LevelThe initial threshold screening level (ITSL) for diphenyloxide (also known as phenyl ether) is 70 μg/m3 based on an eight hour averaging time.
Diphenyl ether Preparation Products And Raw materials
Raw materialsSodium hydroxide-->Hydrochloric acid-->Potassium hydroxide-->Phenol-->Chlorobenzene-->Copper(II) sulfate-->Copper-->potassium phenolate
Preparation Products4-IODOQUINOLINE-->Decabromodiphenyl oxide-->7-TRIFLUOROMETHYL-4-QUINOLINETHIOL-->Triclosan-->6-bromoquinolin-4(3H)-one-->7-BROMO-3,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID-->2-Piperazinone-->ETHYL 4-CHLOROTHIENO[2,3-B]PYRIDINE-5-CARBOXYLATE-->4-Hydroxy carbazole-->(OXYDI-2,1-PHENYLENE)BIS(DIPHENYLPHOSPHINE)-->7-(TRIFLUOROMETHYL)-4-QUINOLINOL-->4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID-->4-Hydroxy-2-methylquinoline-->5,7-BIS(TRIFLUOROMETHYL)-4-CHLOROQUINOLINE-->Nimesulide-->5,7-BIS(TRIFLUOROMETHYL)-4-HYDROXYQUINOLINE-->Pyriproxyfen-->3,4-DIHYDRO-8-HYDROXY-4-OXOQUINOLINE-3-CARBOXYLIC ACID-->Ethyl 7-bromo-3,4-dihydro-4-oxoquinoline-3-carboxylate ,97%-->5,7-BIS(TRIFLUOROMETHYL)-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID-->4-HYDROXY-5,7-BIS-TRIFLUOROMETHYL-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER-->4-HYDROXY-8-METHOXYQUINOLINE-3-CARBOXYLIC ACID-->4-Chloro-7-(trifluoromethyl)quinoline-->Tracid Brilliant Red B-->ETHYL 4-HYDROXY-7-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE-->ETHYL 4-HYDROXY-6-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE-->fluorocarbon sulfactant 6201-->3-METHYL-4-PYRIDINECARBOXYLIC ACID-->2-PHENOXYPHENYLBORONIC ACID-->4-HYDROXY-8-METHOXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER-->PHOSFOLAN-->A-METHYL-3-PHENOXYBENZENEACETALDEHYDE-->PHENOXATHIIN-->4-(4-chlorophenoxy-2‘-chlorophenyl-α-bromo ethanone)-->Disodium 4-dodecyl-2,4'-oxydibenzenesulfonate-->FENOPROFEN-->DICLOFOP-METHYL-->corrosion inhibitor PTX-4-->Pentabromodiphenyl ether-->TRIETHYL M-PHENOXYBENZYL AMMOUIUM CHLORIDE
Tag:Diphenyl ether(101-84-8) Related Product Information
Diphenyl sulfide Propofol Impurity 7 4-Isopropylphenol 3,6-Diisopropyl-1,2-benzenediol 2,6-Diisopropyl-1,4-benzoquinone 2-isopropylhydroquinone 2,5-DIISOPROPYLPHENOL 2,4,6-triisopropylphenol Propofol 2,2-Dimethyl-4-isopropyl-1,3-benzodioxole (Propofol Impurity L) 2,6-diisopropylbenzoic acid 3,5-Diisopropyl-4-hydroxybenzoic acid 3,3',5,5'-Tetraisopropylbiphenyl-4,4'-diol 2-(1-Methylethenyl)-6-(1-Methylethyl)phenol Isopropyl 2-Isopropylphenyl Ether Isopropyl4-hydroxy-3,5-diisopropylbenzoate PROPOFOL RELATED COMPOUND C (50 MG) (2,6-DIISOPROPYLPHENYL ISOPROPYLETHER) 2-Isopropyl-6-propylphenol (Propofol Impurity O) Diphenyl Oxide

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