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

Flash point:

>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 Gravity

1.073

Relative polarity

2.8

Odor

Weak geranium.

Odor Threshold

0.1ppm

explosive limit

0.8-1.5%(V)

Water Solubility 

insoluble

FreezingPoint 

27℃

Merck 

14,7288

JECFA Number

1255

BRN 

1364620

Henry's Law Constant

2.13 at 20 °C (approximate - calculated from water solubility and vapor pressure)

Exposure limits

NIOSH REL: TWA 1 ppm (7 mg/m³), IDLH 100 ppm; OSHA PEL: TWA 1 ppm; ACGIH TLV: TWA 0.1, STEL 2 ppm (adopted).

InChIKey

USIUVYZYUHIAEV-UHFFFAOYSA-N

LogP

4.21 at 25℃

CAS DataBase Reference

101-84-8(CAS DataBase Reference)

NIST Chemistry Reference

Diphenyl ether(101-84-8)

EPA Substance Registry System

Phenyl 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

WGK Germany 

2

RTECS 

KN8970000

Autoignition Temperature

610 °C

TSCA 

Yes

HS Code 

2909 30 10

HazardClass 

9

PackingGroup 

III

Hazardous Substances Data

101-84-8(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 2450 mg/kg LD50 dermal Rabbit > 7940 mg/kg

IDLA

100 ppm

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Diphenyl ether Usage And Synthesis

Description

Diphenyl 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.

Chemical Properties

Diphenyl oxide is a practically colorless crystalline solid with a strong geranium-like 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 Properties

Diphenyl 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.

Chemical Properties

Diphenyl ether has a harsh, floral-green, metallic geranium-type odor.

Physical properties

Colorless solid or liquid with a geranium-like odor. An experimentally determined odor threshold concentration of 100 ppb_v was reported by Leonardos et al. (1969).

Occurrence

Reported found in muscat grapes, grilled beef, green tea, potato chips, buckwheat, Bourbon vanilla and lemon balm.

Uses

Phenyl Ether is an Impurity of Propofol (P829750).

Uses

Diphenyl 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.

Uses

Heat-transfer medium; in perfuming soaps; in organic syntheses

Definition

ChEBI: An aromatic ether in which the oxygen is attached to two phenyl substituents. It has been found in muscat grapes and vanilla.

Preparation

By heating potassium phenolate with bromobenzene or with chlorobenzene at elevated temperatures.

Aroma threshold values

Aroma characteristics at 1.0%: grassy, musty, powdery, dry, terpy, ocimenelike, aromatic and hoplike with green juniper berry nuances.

Taste threshold values

Taste 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 Description

Colorless liquid with a mild pleasant odor. May float or sink in water. Freezing point is 81°F.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Diphenyl oxide can react with oxidizing materials. . A vigorous reaction occurred between the ether and chlorosulfuric acid.

Health Hazard

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.

Fire Hazard

Diphenyl oxide is combustible.

Flammability and Explosibility

Nonflammable

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Moderately 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

Carcinogenicity

Phenyl ether was not mutagenic in the Ames Salmonella assay with or without metabolic activation.

Purification Methods

Crystallise 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.]

Diphenyl ether(101-84-8)Related Product Information

• 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
• Propofol Impurity
• PROPOFOL RELATED COMPOUND C (50 MG) (2,6-DIISOPROPYLPHENYL ISOPROPYLETHER)
• 2-Isopropyl-6-propylphenol (Propofol Impurity O)
• 2-Isopropylphenol
• 2,4-DIISOPROPYLPHENOL