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75-21-8

Basic Information
CAS No.: 75-21-8
Name: Ethylene oxide
Article Data: 191
Cas Database
Molecular Structure:
Molecular Structure of 75-21-8 (Ethylene oxide)
Formula: C2H4O
Molecular Weight: 44.0532
Synonyms: Ethyleneoxide (8CI);Ethyleneoxy (6CI);1,2-Epoxyethane;Dihydrooxirene;Dimethylene oxide;ETO;Epoxyethane;Ethene oxide;Oxacyclopropane;Oxane;Oxidoethane;Oxirene, dihydro-;Oxyfume;Oxyfume 12;Oxyfume 2002;T-Gas;
EINECS: 200-849-9
Density: 0.995 g/cm3
Melting Point: - 111 °C(lit.)
Boiling Point: 10.699 °C at 760 mmHg
Flash Point: 低于-17.7oC
Solubility: N/A
Appearance: clear colorless gas with an ethereal odor
Hazard Symbols: HighlyF+; ToxicT
Risk Codes: 45-46-12-23-36/37/38
Safety: 53-45-36/37-16-24/25-23
Transport Information: UN 2037 2.3
PSA: 12.53000
LogP: 0.01660
Synthetic route
107-07-3

2-chloro-ethanol

75-21-8

oxirane

Conditions
ConditionsYield
With sodium hydroxide at 60 - 70℃; Reagent/catalyst; Temperature;97.97%
With -base at 25℃;
With potassium hydroxide
1243300-84-6

C20H13AsF12O3

A

75-21-8

oxirane

B

C18H8AsF12O2(1-)*K(1+)

Conditions
ConditionsYield
With potassium hydride In [D3]acetonitrile at 0 - 45℃; for 10.6667h; Inert atmosphere;A n/a
B 96%
74-85-1

ethene

75-21-8

oxirane

Conditions
ConditionsYield
With nitrogen; chloroethane; carbon dioxide; oxygen; silver and cesium in alpha-aluminum oxide support at 225℃; under 12001.2 Torr; Product distribution / selectivity; Microchannel reactor;92.7%
With oxygen at 225℃; Reagent/catalyst; Temperature; Inert atmosphere;21.28%
With sulfur dioxide; phosphorus-vanadium-titanium catalyst KFK-77 at 400℃;20%
107-06-2

1,2-dichloro-ethane

75-21-8

oxirane

Conditions
ConditionsYield
With potassium hydroxide; sodium formate; Aliquat 336 at 105℃; for 0.25h;70%
141-97-9

ethyl acetoacetate

106-93-4

ethylene dibromide

A

75-21-8

oxirane

B

32933-03-2

ethyl 1-acetylcyclopropanecarboxylate

C

107-21-1

ethylene glycol

Conditions
ConditionsYield
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis;A n/a
B 22%
C n/a
106-93-4

ethylene dibromide

105-53-3

diethyl malonate

A

75-21-8

oxirane

B

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

C

107-21-1

ethylene glycol

Conditions
ConditionsYield
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis;A n/a
B 13%
C n/a
106-93-4

ethylene dibromide

108-59-8

malonic acid dimethyl ester

A

75-21-8

oxirane

B

6914-71-2

dimethyl 1,1-cyclopropanedicarboxylate

C

107-21-1

ethylene glycol

Conditions
ConditionsYield
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis;A n/a
B 11%
C n/a
74-84-0

ethane

75-21-8

oxirane

Conditions
ConditionsYield
With oxygen at 310℃;1.2%
With oxygen; Ni-Nb-O mixed oxides on γ-alumina (15% Ni, 4.02% Nb); Ag/γ-alumina (15% Ag) at 350℃; under 7500.75 Torr; Product distribution / selectivity;
With oxygen; Ag/γ-alumina (15% Ag) at 350℃; under 7500.75 Torr; Product distribution / selectivity;
96-49-1

[1,3]-dioxolan-2-one

A

75-21-8

oxirane

B

15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

Conditions
ConditionsYield
at 200℃; Pyrolysis;
93-59-4

Perbenzoic acid

74-85-1

ethene

75-21-8

oxirane

Conditions
ConditionsYield
With iodine; 1,1,2,2-tetrachloroethane
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History

  Ethylene oxide (CAS NO.75-21-8) prepared it by treating 2-chloroethanol with a base. It was first reported in 1859 by the French chemist Charles-Adolphe Wurtz, it achieved industrial importance during World War I as a precursor to both the coolant ethylene glycol and the chemical weapon mustard gas. In 1931, Theodore Lefort, another French chemist, discovered a means to prepare ethylene oxide directly from ethylene and oxygen, using silver as a catalyst. Since 1940, almost all ethylene oxide(75-21-8) produced industrially has been made using this method. Ethylene oxide(75-21-8) sterilization for the preservation of spices was patented in 1938 by the American chemist Lloyd Hall, and it is still used in that role.
 

Specification

The Ethylene oxide, with the CAS registry number 75-21-8 and EINECS registry number 200-849-9, has the systematic name of oxirane. And the molecular formula of this chemical is C2H4O. It is a kind of colorless gas with a faintly sweet odor, and belongs to the following product categories: Organics; Oxiranes; Simple 3-Membered Ring Compounds; Fumigants Chromatography; General Use; Air Monitoring Standards; Alpha Sort; E; E-LAlphabetic; Insecticides; Volatiles/ Semivolatiles.

The Ethylene oxide, also known as oxirane, is a cyclic ether. It is the simplest epoxide, and because of its special molecular structure, it easily participates in the addition reaction, opening its cycle, and thus easily polymerizes. What's more, it is isomeric with acetaldehyde.
 
The physical properties of Ethylene oxide are as following: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 11.501; (5)ACD/KOC (pH 7.4): 11.501; (6)#H bond acceptors: 1; (7)#H bond donors: 0; (8)#Freely Rotating Bonds: 0; (9)Polar Surface Area: 12.53 Å2; (10)Index of Refraction: 1.404; (11)Molar Refractivity: 10.829 cm3; (12)Molar Volume: 44.283 cm3; (13)Polarizability: 4.293×10-24cm3; (14)Surface Tension: 31.257 dyne/cm; (15)ensity: 0.995 g/cm3; (16)Enthalpy of Vaporization: 25.54 kJ/mol; (17)Boiling Point: 10.699 °C at 760 mmHg; (18)Vapour Pressure: 1255.443 mmHg at 25°C.

Preparation of Ethylene oxide: It is industrially produced by direct oxidation of ethylene in the presence of silver catalyst. It can also be prepared by treating 2-chloroethanol with potassium hydroxide:
Cl–CH2CH2–OH + KOH → (CH2CH2)O + KCl + H2O

Uses of Ethylene oxide: It is one of the most important raw materials used in the large-scale chemical production. It is used for synthesis of ethylene glycols, including diethylene glycol and triethylene glycol. It is also used for the synthesis of ethylene glycol ethers, ethanolamines and ethoxylates. What's more, it is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. In addition, it is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. Last but not the least, it is extremely flammable and explosive and is used as a main component of thermobaric weapons.

You should be cautious while dealing with this chemical. It is a highly flammable chemical which irritates eyes, respiratory system and skin. It has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. What's more, it may cause cancer and heritable genetic damage. Therefore, you had better take the following instructions: Wear suitable protective clothing and gloves; Avoid contact with skin and eyes; Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer); Keep away from sources of ignition - No smoking; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible); Avoid exposure - obtain special instruction before use.

You can still convert the following datas into molecular structure:
(1)SMILES: C1CO1
(2)InChI: InChI=1/C2H4O/c1-2-3-1/h1-2H2
(3)InChIKey: IAYPIBMASNFSPL-UHFFFAOYAX

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo subcutaneous 100mg/kg (100mg/kg)   "Beitrage zur Toxikologie des Athylenoxyds und der Glykole, Dissertation," Hofbauer, A., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1933Vol. -, Pg. -, 1933.
dog LC50 inhalation 960ppm/4H (960ppm) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
AMA Archives of Industrial Health. Vol. 13, Pg. 237, 1956.
dog LD50 intravenous 330mg/kg (330mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Thoracic and Cardiovascular Surgery. Vol. 61, Pg. 309, 1971.
guinea pig LC50 inhalation 1500mg/m3/4H (1500mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 67, 1982.
guinea pig LD50 oral 270mg/kg (270mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.
human TCLo inhalation 12500ppm/10S (12500ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Journal of Hygiene. Vol. 32, Pg. 409, 1932.
mouse LC50 inhalation 836ppm/4H (836ppm)   National Technical Information Service. Vol. PB214-270,
mouse LD50 intraperitoneal 175mg/kg (175mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(1), Pg. 23, 1983.
mouse LD50 intravenous 290mg/kg (290mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 43, Pg. 69, 1978.
rabbit LDLo intravenous 175mg/kg (175mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: REGIDITY
Journal of Hygiene. Vol. 32, Pg. 409, 1932.
rat LC50 inhalation 800ppm/4H (800ppm) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

LIVER: OTHER CHANGES
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 258, 1969.
rat LD50 oral 72mg/kg (72mg/kg)   Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 17, 1978.
rat LD50 subcutaneous 187mg/kg (187mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(1), Pg. 23, 1983.
rat LDLo unreported 200mg/kg (200mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LIVER: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 258, 1969.
women TCLo inhalation 500ppm/2M (500ppm) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Drug Intelligence and Clinical Pharmacy. Vol. 15, Pg. 384, 1981.