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60-29-7

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Basic Information
CAS No.: 60-29-7
Name: Diethyl ether
Article Data: 681
Molecular Structure:
Molecular Structure of 60-29-7 (Diethyl ether)
Formula: C4H10O
Molecular Weight: 74.1228
Synonyms: Ether(6CI);Ethyl ether (8CI);1,1'-Oxybisethane;3-Oxapentane;Anaesthetic ether;Anesthesia ether;Anesthetic ether;Diethyl oxide;Ethoxyethane;Ethyl oxide;NSC 100036;Pronarcol;Sulfuric ether;Ethyl ether;Ethane, 1,1'-oxybis-;
EINECS: 200-467-2
Density: 0.734 g/cm3
Melting Point: -116 °C
Boiling Point: 33.177 °C at 760 mmHg
Flash Point: -45 °C
Solubility: 69 g/L (20 °C) in water
Appearance: Colourless liquid
Hazard Symbols: HighlyF+, HarmfulXn, ToxicT
Risk Codes: 12-19-22-66-67-39/23/24/25-23/24/25
Safety: 9-16-29-33-45-36/37
Transport Information: UN 1155 3/PG 1
PSA: 9.23000
LogP: 1.04280
Synthetic route
64-17-5

ethanol

60-29-7

diethyl ether

Conditions
ConditionsYield
With reduced Sn/hydrotalcite catalyst at 250℃; under 25502.6 Torr; Catalytic behavior; Reagent/catalyst; Temperature; Pressure;99%
With SA5 at 199.84℃; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;2.6%
With sulfuric acid at 130 - 140℃; Darstellung im grossen;
64-17-5

ethanol

A

60-29-7

diethyl ether

B

74-85-1

ethene

Conditions
ConditionsYield
With alumina at 449.84℃; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Overall yield = 100 %;A 0.1%
B 98.9%
C2I2O2Rh(1-)*C8H20N(1+); tetraethylammonium iodide; hydrogen iodide In water at 110℃; Product distribution / selectivity; Inert atmosphere; Autoclave;A 10%
B 50%
1-methyl-3-(propyl-3-sulfonyl)imidazolium trifluoromethanesulfonate; CF3O3S(1-)*CHF3O3S*C7H13N2O3S(1+) at 240 - 260℃; for 4h; Product distribution / selectivity;A n/a
B 12%
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

65039-09-0

1-ethyl-3-methyl-1H-imidazol-3-ium chloride

A

377739-43-0

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate

B

60-29-7

diethyl ether

C

75-00-3

chloroethane

Conditions
ConditionsYield
at 80℃; for 3h; Product distribution / selectivity;A 98.9%
B n/a
C n/a
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

30388-20-6

N,N,N',N',N'',N''-hexamethylguanidinium chloride

A

hexamethylguanidinium tris(pentafluoroethyl)trifluorophosphate

B

60-29-7

diethyl ether

C

75-00-3

chloroethane

Conditions
ConditionsYield
at 80℃; for 3h;A 98.9%
B n/a
C n/a
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

155371-19-0

1-ethyl-3-methylimidazolium hexafluorophosphate

A

377739-43-0

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate

B

60-29-7

diethyl ether

C

353-36-6

1-fluoroethane

D

7647-19-0, 874483-74-6

phosphorus pentafluoride

Conditions
ConditionsYield
at 100℃; for 10h; Product distribution / selectivity;A 98.7%
B n/a
C n/a
D n/a
945614-34-6

triethyloxonium bis(trifluoromethylsulfonyl)imide

59016-54-5

1-cyano-4-N,N-dimethylaminopyridinium bromide

A

74-96-4

ethyl bromide

B

60-29-7

diethyl ether

C

945614-38-0

1-cyano-4-dimethylaminopyridinium bis(trifluoromethylsulfonyl)imide

Conditions
ConditionsYield
at 60℃; for 5h;A n/a
B n/a
C 98.2%
945614-34-6

triethyloxonium bis(trifluoromethylsulfonyl)imide

65039-09-0

1-ethyl-3-methyl-1H-imidazol-3-ium chloride

A

60-29-7

diethyl ether

B

75-00-3

chloroethane

C

174899-82-2

1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide

Conditions
ConditionsYield
at 80℃; for 3h;A n/a
B n/a
C 97.9%
766-77-8

Dimethylphenylsilane

123-63-7

paracetaldehyde

A

60-29-7

diethyl ether

B

56-33-7

1,1,3,3-tetramethyl-1,3-diphenyldisiloxane

Conditions
ConditionsYield
With (pentamethylcyclopentadienyl)Ge(II)+B(ArF)4- In dichloromethane-d2 at 50℃; Catalytic behavior; Reagent/catalyst;A n/a
B 97%
141-78-6

ethyl acetate

A

60-29-7

diethyl ether

B

597-67-1

ethoxytriethylsilane

Conditions
ConditionsYield
With triethylsilane; [CpW(CO)2(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)]B(C6F5)4 at 23℃; for 26h; Conversion of starting material;A 5.9%
B 96.3%

bis(pentamethylcyclopentadienyl)ytterbium(diethyl ether)

3790-23-6

tetraethyldiphosphine disulfide

A

115018-02-5

((CH3)5C5)2Yb(S2P(C2H5)2)

B

60-29-7

diethyl ether

C

3040-63-9

1,1,2,2-tetraethyldiphosphane

D

tetraethyldiphosphane monosulfide

Conditions
ConditionsYield
In toluene stirring, 2 h, under N2; concn., cooling to -10°C; elem. anal.;A 96%
B n/a
C n/a
D n/a
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History

   Alchemist Raymundus Lullus is credited with discovering the compound in 1275 AD, although there is no contemporary evidence of this. 
   Ethyl ether (CAS NO.60-29-7) was first synthesized in 1540 by Valerius Cordus, who called it "oil of sweet vitriol" (oleum dulcis vitrioli)—the name was because it was originally discovered by distilling a mixture of ethanol and sulfuric acid (then known as oil of vitriol)—and noted some of its medicinal properties. At about the same time, Theophrastus Bombastus von Hohenheim, better known as Paracelsus, discovered ether's analgesic properties. In 1730 ,August Siegmund Frobenius gave the name ether  to the substance  .

Consensus Reports

IARC Cancer Review: Animal No Adequate Data IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 93.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Standards and Recommendations

OSHA PEL: TWA 400 ppm; STEL 500 ppm
ACGIH TLV: TWA 400 ppm; STEL 500 ppm
DFG MAK: 400 ppm (1200 mg/m3)
DOT Classification:  3; Label: Flammable Liquid

Analytical Methods

For occupational chemical analysis use NIOSH: Ethyl Ether, 1610.

Specification

The Ethyl ether with CAS registry number of 60-29-7 is also known as Diethyl ether. The IUPAC name is Ethoxyethane. It belongs to product categories of Refrigerants; Anhydrous Solvents; Synthetic Organic Chemistry; Chemistry. Its EINECS registry number is 200-467-2. In addition, the formula is C4H10O and the molecular weight is 74.12. This chemical is a colourless liquid and should be cool and dry place away from oxidizing agents.

Physical properties about Ethyl ether are: (1)ACD/LogP: 1.04; (2)ACD/LogD (pH 5.5): 1.041; (3)ACD/LogD (pH 7.4): 1.041; (4)ACD/BCF (pH 5.5): 3.638; (5)ACD/BCF (pH 7.4): 3.638; (6)ACD/KOC (pH 5.5): 87.722; (7)ACD/KOC (pH 7.4): 87.722; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 9.23Å2; (11)Index of Refraction: 1.361; (12)Molar Refractivity: 22.326 cm3; (13)Molar Volume: 100.925 cm3; (14)Surface Tension: 19.09 dyne/cm; (15)Density: 0.734 g/cm3; (16)Enthalpy of Vaporization: 26.52 kJ/mol; (17)Boiling Point: 33.177 °C at 760 mmHg; (18)Vapour Pressure: 566.752 mmHg at 25 °C.

Preparation of Ethyl ether. Firstly, mix ethanol (95%) and concentrated sulfuric acid (98%) with ratio of 1:1 and heat the reaction mixture to 83 °C. Then pass into ethanol vapor and stir the mixture at 120-125 °C. After the reaction, gaseous product is washed through sodium hydroxide solution, saturated solution of sodium bisulfite and distilled water at atmospheric pressure. At last, product is obtained by collecting fraction of 33.5-34.5 °C.

Ethyl ether is prepared by reaction of ethanol (95%) and concentrated sulfuric acid (98%).

Uses of Ethyl ether: it is important anesthetic in medicine. Besides, it is used as analytical reagent for nickel, potassium, magnesium and other analysis. What's more, it is used as solvent, cleaning agent and also used in medicine, electronic and other industries. For example, it is used to produce benzoic acid ethyl ester by reaction with benzoyl chloride. The reaction needs catalyst anhydrous cobalt(II) chloride and solvent acetonitrile at ambient temperature for 8 hours. The tield is about 49%.

The chemical is used to produce benzoic acid ethyl ester by reaction with benzoyl chloride.

When you are using this chemical, please be cautious about it. As a chemical, it is extremely flammable and may form explosive peroxides. What's more, it has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. Besides, its repeated exposure may cause skin dryness or cracking vapours may cause drowsiness and dizziness. During using it, wear suitable protective clothing and gloves and do not empty into drains. Keep container in a well-ventilated place and away from sources of ignition. In case of accident or if you feel unwell seek medical advice immediately. It is necessary to take precautionary measures against static discharges.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CCOCC
2. InChI: InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
3. InChIKey: RTZKZFJDLAIYFH-UHFFFAOYSA-N

The toxicity data is as follows: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LCLo inhalation 76000ppm (76000ppm)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1294, 1935.
frog LDLo subcutaneous 24gm/kg (24000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1295, 1935.
guinea pig LDLo intraperitoneal 2gm/kg (2000mg/kg)   American Industrial Hygiene Association Journal. Vol. 35, Pg. 21, 1974.
human TCLo inhalation 200ppm (200ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 282, 1943.
man LDLo oral 260mg/kg (260mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LC50 inhalation 31000ppm/30M (31000ppm) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Experimental Animals. Jikken Dobutso Iho. Vol. 34, Pg. 379, 1985.
mouse LD50 intraperitoneal 2420mg/kg (2420mg/kg)   Proceedings of the Western Pharmacology Society. Vol. 27, Pg. 511, 1984.
mouse LD50 intravenous 996mg/kg (996mg/kg)   Journal of Pharmaceutical Sciences. Vol. 67, Pg. 566, 1978.
mouse LDLo subcutaneous 8mg/kg (8mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1295, 1935.
rabbit LCLo inhalation 106000ppm (106000ppm)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1294, 1935.
rabbit LD50 skin > 20mL/kg (20mL/kg)   American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
rat LCLo inhalation 32000ppm/4H (32000ppm)   American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
rat LD50 oral 1215mg/kg (1215mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 699, 1971.