Conditions | Yield |
---|---|
With sodium hydroxide at 60 - 70℃; Reagent/catalyst; Temperature; | 97.97% |
With -base at 25℃; | |
With potassium hydroxide |
Conditions | Yield |
---|---|
With potassium hydride In [D3]acetonitrile at 0 - 45℃; for 10.6667h; Inert atmosphere; | A n/a B 96% |
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% |
Conditions | Yield |
---|---|
With potassium hydroxide; sodium formate; Aliquat 336 at 105℃; for 0.25h; | 70% |
ethyl acetoacetate
ethylene dibromide
A
oxirane
B
ethyl 1-acetylcyclopropanecarboxylate
C
ethylene glycol
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis; | A n/a B 22% C n/a |
ethylene dibromide
diethyl malonate
A
oxirane
B
diethyl cyclopropane-1,1-dicarboxylate
C
ethylene glycol
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis; | A n/a B 13% C n/a |
ethylene dibromide
malonic acid dimethyl ester
A
oxirane
B
dimethyl 1,1-cyclopropanedicarboxylate
C
ethylene glycol
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis; | A n/a B 11% C n/a |
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; |
[1,3]-dioxolan-2-one
A
oxirane
B
methylammonium carbonate
Conditions | Yield |
---|---|
at 200℃; Pyrolysis; |
Conditions | Yield |
---|---|
With iodine; 1,1,2,2-tetrachloroethane |
Conditions | Yield |
---|---|
With sodium oxide at 180℃; |
Conditions | Yield |
---|---|
With silver(l) oxide at 150℃; |
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
With silver(l) oxide at 250℃; | |
With sodium oxide at 180℃; |
Conditions | Yield |
---|---|
at 25℃; |
Conditions | Yield |
---|---|
With hydrazine |
Conditions | Yield |
---|---|
With methane; water; oxygen at 37.5℃; Mechanism; Product distribution; Thermodynamic data; Irradiation; ΔH0; |
Conditions | Yield |
---|---|
at 159℃; for 5.5h; |
Conditions | Yield |
---|---|
In water Quantum yield; Irradiation; |
epoxybutene
2-(phenylselenyl)ethanol
A
oxirane
B
(+/-)-1-(phenylseleno)-but-3-en-2-ol
Conditions | Yield |
---|---|
at 159℃; for 5.5h; |
epoxybutene
2-diphenylphosphinoethanol
A
oxirane
B
ethene
C
acetaldehyde
Conditions | Yield |
---|---|
In chlorobenzene at 100℃; for 1h; Mechanism; a new decomposition path of reaction; |
glycidyl n-butyl ether
2-(phenylselenyl)ethanol
A
oxirane
B
1-butoxy-3-(phenylselanyl)propan-2-ol
Conditions | Yield |
---|---|
at 159℃; for 5.5h; |
Conditions | Yield |
---|---|
vanadia at 350℃; flow-type reactor; | 0.2 g |
vanadia at 350℃; Product distribution; flow-type reactor; | 0.2 g |
styrene oxide
2-(phenylselenyl)ethanol
A
oxirane
B
1-phenyl-2-(phenylselanyl)ethanol
Conditions | Yield |
---|---|
at 159℃; for 5.5h; |
styrene oxide
2-diphenylphosphinoethanol
A
oxirane
B
styrene
C
ethene
D
acetaldehyde
E
acetophenone
Conditions | Yield |
---|---|
In chlorobenzene at 150℃; for 1h; Mechanism; a new decomposition path of reaction; |
β-Propiolactone
A
oxirane
B
methane
C
ethene
D
acetaldehyde
Conditions | Yield |
---|---|
With mercury at 100℃; Product distribution; Irradiation; other reagent, other temperature; |
Conditions | Yield |
---|---|
With oxygen at 500℃; under 15 Torr; for 0.00833333h; Kinetics; Rate constant; Mechanism; variation of temperature, and pressure; |
Conditions | Yield |
---|---|
With oxygen for 0.5h; Product distribution; also without CF4; | A 1.2 mol B 6.7 mol |
t-butyl 2-hydroxyethyl peroxide
A
oxirane
B
glycolic Acid
C
methane
D
Glycolaldehyde
E
acetone
F
tert-butyl alcohol
Conditions | Yield |
---|---|
In water at 99.9 - 149.9℃; Thermodynamic data; Kinetics; Product distribution; further solvent; various pH; in the presence of FeCl2 also; in glass and steel test tube in the presence of HCl; activation energy; |
Conditions | Yield |
---|---|
With isopropoxydiisobutylaluminum In hexane Product distribution; Ambient temperature; other oxiranes; var. Lewis acids; var. solvents; var. temperatures; | 100% |
With aluminum isopropoxide 1.) RT, 2 h, 2.) RT, 15 h; Yield given. Multistep reaction; |
oxirane
3-bromo-2,4-dimethylpenta-1,3-diene
3-isopropenyl-4-methyl-pent-3-en-1-ol
Conditions | Yield |
---|---|
Stage #1: 3-bromo-2,4-dimethylpenta-1,3-diene With tert.-butyl lithium In tetrahydrofuran at -78℃; for 0.166667h; Metallation; Stage #2: oxirane In tetrahydrofuran at -78 - 0℃; Substitution; | 100% |
Stage #1: 3-bromo-2,4-dimethylpenta-1,3-diene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Stage #2: oxirane In tetrahydrofuran; pentane at -78 - 21℃; for 2h; | 83% |
With tert.-butyl lithium -78 deg C to 21 deg C; | 78% |
Conditions | Yield |
---|---|
With 3-(2-hydroxylethyl)-1-(3-aminopropyl)imidazolium bromide grafted onto divinylbenzene polymer (PDVB-HEIMBr) at 140℃; under 15001.5 Torr; for 3h; Autoclave; | 100% |
With bis[(1R,2R)-N,N'-bis(3,5-di-tert-butyl-salicylidene)cyclohexane-1,2-diaminoaluminium(III)]oxide; tetrabutylammomium bromide at 26℃; under 2280.15 Torr; for 24h; | 100% |
With choline chloride; zinc dibromide at 110℃; under 11251.1 Torr; for 1h; Autoclave; neat (no solvent); | 100% |
oxirane
N-(1-chlorohexafluoro-1-methylethyl)benzenesulfinimidoyl chloride
C11H9Cl2F6NOS
Conditions | Yield |
---|---|
In tetrachloromethane at 25℃; for 48h; | 100% |
oxirane
N-(2-chlorohexafluoroisopropyl)-p-toluenesulfinimidoyl chloride
C12H11Cl2F6NOS
Conditions | Yield |
---|---|
In tetrachloromethane at 25℃; for 48h; | 100% |
oxirane
N-(2-chlorohexafluoroisopropyl)-p-nitrobenzenesulfinimidoyl chloride
C11H8Cl2F6N2O3S
Conditions | Yield |
---|---|
In tetrachloromethane at 25℃; for 48h; | 100% |
Conditions | Yield |
---|---|
In methanol at 5 - 7℃; for 336h; | 100% |
Conditions | Yield |
---|---|
In methanol at 5 - 7℃; for 336h; | 100% |
Conditions | Yield |
---|---|
In methanol at 5 - 7℃; for 336h; | 100% |
oxirane
3-(2-methoxy-5-methylphenyl)-3-phenylpropan-1-ol
Conditions | Yield |
---|---|
Stage #1: oxirane; (2-methoxy-5-methylphenyl)phenylmethane With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 4h; Stage #2: With water; ammonium chloride In tetrahydrofuran | 100% |
oxirane
phenobarbital
5-ethyl-1,3-bis-(2-hydroxy-ethyl)-5-phenyl-pyrimidine-2,4,6-trione
Conditions | Yield |
---|---|
With tetraethylammonium chloride In N-methyl-acetamide | 100% |
Conditions | Yield |
---|---|
With hydrogen cation In tetrahydrofuran shaken for 10 min at room temp.; centrifuged, decanted, soln. contains naphthalene, pptn. hydrolysed in THF: butanediol detd. by GLC in the organic layer and a pptn. (Yb(OH)3); | A 83% B 100% C 75% |
Conditions | Yield |
---|---|
Stage #1: oxirane; ricinus oil; 1-amino-3-(dimethylamino)propane With sodium tetrahydroborate; sodium methylate In methanol at 130℃; for 2h; Stage #2: dimethyl sulfate at 65℃; for 4h; | 100% |
oxirane
4-(4-(trifluoromethoxy)phenoxy)piperidine
2-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl)ethanol
Conditions | Yield |
---|---|
at 0℃; for 0.833333h; | 100% |
In dichloromethane at 0℃; for 3h; | 100% |
oxirane
Conditions | Yield |
---|---|
Stage #1: 7-morpholino-6-nitro-3,4-dihydroquinolin-2(1H)-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 60℃; for 0.5h; Stage #2: oxirane In N,N-dimethyl-formamide; mineral oil at 60℃; for 18h; | 100% |
oxirane
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
Stage #1: methyloxirane; recorcinol With potassium hydroxide In toluene at 48.8789℃; for 1.5h; Under N2; Stage #2: oxirane at 48.8789℃; for 2h; | 99.7% |
oxirane
p-acetylaminobenzenesulfonyl chloride
2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate
Conditions | Yield |
---|---|
Stage #1: p-acetylaminobenzenesulfonyl chloride With sodium metabisulfite; sodium hydroxide at 30℃; pH=7 - 7.5; Stage #2: oxirane at 40℃; pH=7.5 - 8; Stage #3: With sulfuric acid at 150 - 160℃; under 3750.38 Torr; | 99.7% |
Conditions | Yield |
---|---|
With hydrogen sulfide at 20℃; Temperature; | 99.5% |
With hydrogen sulfide |
Conditions | Yield |
---|---|
With sodium hydrogen sulfate at 40℃; for 0.25h; Temperature; Large scale; | 99.5% |
With water; sodium hydrogensulfite | |
With sodium metabisulfite |
Conditions | Yield |
---|---|
With Tau at 102 - 133℃; for 4h; Temperature; Autoclave; Inert atmosphere; Industrial scale; | 99.4% |
With methanol | |
With water at 100℃; im Rohr; |
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.
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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