Name: 1,2-Epoxy ethane
SKU: 75-21-8

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Basic Information

Molecular Structure:
CAS No.:	75-21-8
Name:	1,2-Epoxy ethane
Article Data:	191

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
Appearance:	clear colorless gas with an ethereal odor
Hazard Symbols:	F+; T
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 74-84-0
ethane

: 75-21-8
oxirane

Conditions

Conditions	Yield
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

Conditions	Yield
at 200℃; Pyrolysis;

: 93-59-4
Perbenzoic acid

: 74-85-1
ethene

: 75-21-8
oxirane

Conditions

Conditions	Yield
With iodine; 1,1,2,2-tetrachloroethane

Raw Materials

106-93-4

107-21-1

107-06-2

105-53-3

141-97-9

64-17-5

371-62-0

75-00-3

Downstream Products

503-66-2

927-74-2

5464-12-0

868-77-9

818-61-1

4074-88-8

97-90-5

111-46-6

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- China (Mainland)(24)
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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.

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