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60-29-7

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60-29-7 Usage

Chemical Description

Different sources of media describe the Chemical Description of 60-29-7 differently. You can refer to the following data:
1. Diethyl ether is a common organic solvent.
2. Diethyl ether is a solvent used to wash a product in the article.
3. Diethyl ether is a colorless, highly flammable liquid with a sweet, fruity odor.
4. Diethyl ether is used for extraction purposes.
5. Diethyl ether is a colorless, volatile, and highly flammable liquid that is commonly used as a solvent.
6. Diethyl ether is an organic solvent commonly used for extractions.
7. Diethyl ether is used as a solvent in the reaction with compound 5 to form compounds 6-8.
8. Diethyl ether and THF are used as solvents.
9. Diethyl ether and dichloromethane are solvents used in the reactions, while sodium-benzophenone ketyl and calcium hydride are used to remove oxygen and water from the solvents.

Chemical Properties

Different sources of media describe the Chemical Properties of 60-29-7 differently. You can refer to the following data:
1. Diethyl ether is inactive at room temperatures, but some reactions may also occur. Peroxides are prone to prolonged exposure to oxygen (or light) to become ether peroxide (also known as ether hydroperoxide). Peroxide ether is a viscous liquid that hardly evaporates. Antioxidants are often added in storage of ether to avoid the slow oxidation. Diethyl ether will crack in case of being oxidized violently. In the presence of catalysts, it can break down into aldehydes or acids. It reacts with an organic acid anhydride to form an ester in the presence of a catalyst, or reacts with an inorganic acid anhydride to form an ester without any catalyst. It can react with metal halides to produce addition compounds such as cerium chloride adduct 2(C2H5)2O?BeCl2. It can react with halogen to produce monohalogenated ethers and polyhaloethers. Ether can react with sulfuric acid generating an adduct.
2. Ether, (C2H5)2,also known as ethyl ether, is a colorless liquid. It is used as a solvent,a denaturant, and as an anesthetic in medicine. lt is an organic compound in which two hydrocarbon radicals are joined by an atom of oxygen.
3. Ethyl ether is a colorless, mobile, highly flammable, volatile liquid. Characteristic pungent odor. The Odor Threshold is 0.63 ppm.

Medical uses

It can be used to test the arm-to-lung blood circulation time. After being injected into the upper arm vein, the drug liquid goes from the right atrium, passes right ventricle to reach the lungs, and is then discharged from the respiratory tract. It normally takes 4 to 6 seconds for the patients to smell ether odor from the infusion moment (or 3 to 8 seconds). 【Usage and Dosage】 Take 1ml of ether and 2ml of 0.9% sodium chloride solution, mix them and then inject from the arm vein. Adverse reactions such as temporary chest discomfort, cough, and local pain may occur. 【Precautions】 Patients with potential heart failure are banned. Do not inject Diethyl ether outside the blood vessels mistakenly. Exposure to air or in storage for long, ether forms an explosive mixture of ether peroxides and aldehydes etc. 【Specifications】 Injection: 3ml. 【Warning】 Patients with severe intracranial hypertonia, acute inflammation of the upper respiratory tract, active tuberculosis, severe respiratory disease, cardiovascular disease, liver and kidney functional impairment, severe metabolic disorders and uncontrolled diabetes are strictly prohibited for Ether anesthesia. If the administration is excessive during the operation, respiratory dangers such as weakness of breathing, fall of blood pressure, rapid pulse and pupil dilation will occur. Inhalation at 10% concentration can result in death. The maximum allowable concentration in the workplace is 400×10-6.

First-aid

Rinse with soap when contact with eyes and skin.? Help with the breathing using oxygen gas containing 5% carbon dioxide when breathing is abnormal and the face turns blue. Drink hot tea and coffee to prevent vomiting.

Production

Diethyl ether is produced by dehydrating ethanol at 300 °C in the presence of catalyst.

Description

Diethyl ether is a component of starting fluids and is used as a solvent in the manufacture of synthetic dyes and plastics. Because of its characteristics, diethyl ether was widely used in many countries as an anesthetic agent, but was then replaced by other substances in the 1960s.

Physical properties

Colorless, hygroscopic, volatile liquid with a sweet, pungent odor. Odor threshold concentration is 330 ppb (quoted, Keith and Walters, 1992).

History

Ether was supposedly discovered by Raymundus Lullus (1232–1315) around 1275, although there is no extant evidence of this in his writings. The discoverer of ether is often credited to the German physician and botanist Valerius Cordus (1515–1554), who gave the first description of the preparation of ether in the mid-16th century. Cordus called the substance oleum vitrioli dulce, which is translated as sweet oil of vitriol. Cordus used sulfuric acid (oil of vitriol) to catalyze the conversion of alcohol to ether. At approximately the same time Paracelsus (1493–1541), a Swiss physician who is also cited as a discoverer of ether, observed that chickens were safely put to sleep by breathing vapors from sweet oil of vitriol. In 1730, August Siegmund Frobenius changed the name of sweet vitriol to ether.

Uses

Different sources of media describe the Uses of 60-29-7 differently. You can refer to the following data:
1. Ethyl ether is used as a solvent for fats, oils,waxes, gums, perfumes, and nitrocellulose;in making gun powder; as an anesthetic; andin organic synthesis.
2. Ether was applied topically, inhaled, and consumed for medical purposes well before it was used as an anesthetic. Ether is only slightly soluble in water (6.9%), but it is a good solvent for nonpolar organic compounds. Approximately 65% of ether production is used as a solvent for waxes, fats, oils, gums, resins, nitrocellulose, natural rubber, and other organics. As a solvent, it is used as an extracting agent for plant and animal compounds in the production of pharmaceuticals and cosmetics. Another 25% of total ether production is used in chemical synthesis. It is an intermediate used in the production of monoethanolamine (MEA, C2H7NO). Ether is used in the production of Grignard reagents. A Grignard reagent has the general form RMgX, where R is an alkyl or aryl group and X is a halogen. Grignard reagents are widely used in industrial organic synthesis. A Grignard reagent is typically made by reacting a haloalkane with magnesium in an ether solution, for example, CH3I + MgCH3MgI. Ether is a common starting fluid, especially for diesel engines.
3. Diethyl ether has been used extensively as a general anesthetic.
4. ethyl ether is a solvent that may cause skin irritation. Although considered a non-comedogenic raw material, it is rarely used in cosmetics.
5. Solvent for waxes, fats, oils, perfumes, alkaloids, gums. Excellent solvent for nitrocellulose when mixed with alcohol. Important reagent in organic syntheses, especially in Grignard and Wurtz type reactions. Easily removable extractant of active principles (hormones, etc.) from plant and animal tissues. In the manufacture of gun powder. As primer for gasoline engines.

Definition

Different sources of media describe the Definition of 60-29-7 differently. You can refer to the following data:
1. ChEBI: An ether in which the oxygen atom is linked to two ethyl groups.
2. diethyl ether: A colourless flammablevolatile ether, C2H5OC2H5; r.d. 0.71;m.p. –116°C; b.p. 34.5°C. It can bemade by Williamson’s synthesis. Itis an anaesthetic and useful organicsolvent.

Production Methods

Ether is produced by the dehydration of ethanol using sulfuric acid: 2CH3CH2OH +2H2SO4 → (CH3CH2)2O + H2SO4 + H2O.the temperature of the reaction is carriedout at about 140°C to control for unwanted products.the volatile ether is distilled from themixture. Ether can also be prepared by Williamson synthesis. In this reaction, ethanol reactswith sodium to form sodium ethanolate (Na+C2H5O?). Sodium ethanolate then reacts withchloroethane to form ether and sodium chloride: Na+C2H5O? +C2H5Cl → C2H5OC2H5 +NaCl. Ether is also produced as a by-product in the production of ethanol.

General Description

A clear colorless liquid with an anesthetic odor. Flash point -49°F. Less dense than water and slightly soluble in water. Hence floats on water. Vapors are heavier than air. Used as a solvent and to make other chemicals.

Air & Water Reactions

Highly flammable. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. A mixture of liquid air and Diethyl ether exploded spontaneously, [MCA Case History 616(1960)].

Reactivity Profile

Occasional explosions have occurred when aluminum hydride was stored in ether. The explosions have been blamed on the presence of carbon dioxide impurity in the ether, [J. Amer. Chem. Soc. 70:877(1948)]. Diethyl ether and chromium trioxide react violently at room temperature. Solid acetyl peroxide in contact with ether or any volatile solvent may explode violently. A 5-gram portion in ether detonated while being carried, [Chem. Eng. News 27:175(1949)]. Nitrosyl perchlorate ignites and explodes with Diethyl ether. A mixture of ether and ozone forms aldehyde and acetic acid and a heavy liquid, ethyl peroxide, an explosive, [Mellor 1:911(1946-1947)].

Hazard

CNS depressant by inhalation and skin absorption. Very flammable, severe fire and explosion hazard when exposed to heat or flame. Forms explosive peroxides. Explosive limits in air 1.85– 48%.

Health Hazard

Different sources of media describe the Health Hazard of 60-29-7 differently. You can refer to the following data:
1. Vapor inhalation may cause headache, nausea, vomiting, and loss of consciousness. Contact with eyes will be irritating. Skin contact from clothing wet with the chemical may cause burns.
2. The acute toxicity of diethyl ether is low. Inhalation of high concentrations can cause sedation, unconsciousness, and respiratory paralysis. These effects are usually reversible upon cessation of exposure. Diethyl ether is mildly irritating to the eyes and skin, but does not generally cause irreversible damage. Repeated contact can cause dryness and cracking of the skin due to removal of skin oils. The liquid is not readily absorbed through the skin, in part because of its high volatility. Diethyl ether is slightly toxic by ingestion. Diethyl ether is regarded as having adequate warning properties. There is no evidence for carcinogenicity of diethyl ether, and no reproductive effects have been reported. Chronic exposure to diethyl ether vapor may lead to loss of appetite, exhaustion, drowsiness, dizziness, and other central nervous system effects.
3. Ethyl ether is a narcotic substance and a mildirritant to the skin, eyes, and nose; at lowconcentrations, <200 ppm in air, exposure tothis compound does not produce noticeableeffects in humans. Eye and nasal irritationmay become intolerable at 250–300 ppm.Repeated exposure can cause drying andcracking of skin, due to extraction of oils.Inhalation of its vapors at high concentra tions, above 1% (by volume in air), couldbe hazardous to human health. A concen tration of 3.5–6.5% could produce an anes thetic effect; respiratory arrest may occurabove this concentration (Hake and Rowe1963). Inhalation of 10% ethyl ether by vol ume in air can cause death (ACGIH 1986).Repeated exposure to this compound exhib ited the symptoms of exhaustion, loss ofappetite, sleepiness, and dizzinessAcute oral toxicity of ethyl ether wasfound to be low to moderate, varying withspecies. Ingestion of 300–350 mL can befatal to humans.LC50 value, inhalation (mice): 6500 ppm/100 minLD50 value, oral (rats): 1215 mg/kgIn a comparison with other anestheticagents, diethyl ether was reported to beless toxic than methoxyfluorane [76-38-0], halothane , and isoflurane on test animals upon repeatedexposures at subanesthetic concentrations(Chenoweth et al. 1972; Stevens et al. 1975).At 2000 ppm it did not cause hepatotoxicresponses. Matt et al. (1983) reportedthat ether exposure for 6 minutes inducedsignificant and variable elevations of serumprolactin in female goldenhamstersIn contrast to volatile hydrocarbons, therespiratory arrest caused by ethyl etherwas reversible (Swann et al. 1974). Suchreversibility, however, was observed at alower concentration, about 105 ppm for a 5-minute exposure period in mice. There is noreport of its carcinogenicity in animals orhumans.

Fire Hazard

Different sources of media describe the Fire Hazard of 60-29-7 differently. You can refer to the following data:
1. Diethyl ether is extremely flammable (NFPA rating = 4) and is one of the most dangerous fire hazards commonly encountered in the laboratory, owing to its volatility and extremely low ignition temperature. Ether vapor may be ignited by hot surfaces such as hot plates and static electricity discharges, and since the vapor is heavier than air, it may travel a considerable distance to an ignition source and flash back. Ether vapor forms explosive mixtures with air at concentrations of 1.9 to 36% (by volume). Carbon dioxide or dry chemical extinguishers should be used for ether fires. Diethyl ether forms unstable peroxides on exposure to air in a reaction that is promoted by light; the presence of these peroxides may lead to explosive residues upon distillation.
2. Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back. Decomposes violently when heated.

Flammability and Explosibility

Diethyl ether is extremely flammable (NFPA rating = 4) and is one of the most dangerous fire hazards commonly encountered in the laboratory, owing to its volatility and extremely low ignition temperature. Ether vapor may be ignited by hot surfaces such as hot plates and static electricity discharges, and since the vapor is heavier than air, it may travel a considerable distance to an ignition source and flash back. Ether vapor forms explosive mixtures with air at concentrations of 1.9 to 36% (by volume). Carbon dioxide or dry chemical extinguishers should be used for ether fires. Diethyl ether forms unstable peroxides on exposure to air in a reaction that is promoted by light; the presence of these peroxides may lead to explosive residues upon distillation.

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.

Industrial uses

Diethyl ether as a commercial product is available in several grades and is used as an extraction solvent, reaction solvent, and as a general anesthetic. Ethyl ether is an excellent solvent for alkaloids, dyes, fats, gums, oils, resins, and waxes. Blends of ethyl ether and ethanol are excellent solvents for cellulose nitrate used in the manufacture of guncotton, in collodion solutions and pyroxylin plastics. Ethyl ether is used in the recovery of acetic acid from aqueous solutions in the cellulose acetate and plastic industry. It is used as a starter fuel for diesel engines and as a denaturant in denatured ethanol formulations. Grignard and Wurtz-Fillig synthesis reactions use diethyl ether as an anhydrous, inert reaction medium.

Safety Profile

Moderately toxic to humans by ingestion. Poison experimentally by subcutaneous route. Moderately toxic by intraperitoneal and intravenous routes. badly toxic by inhalation. Human systemic effects by inhalation: olfactory changes. Mutation data reported. A severe eye and moderate skin irritant. Ethyl ether is not corrosive or dangerously reactive. It must not be considered safe for indlviduals to inhale or ingest. It is a depressant of the central nervous system and is capable of producing intoxication, drowsiness, stupor, and unconsciousness. Death due to respiratory failure may result from severe and continued exposure. A very dangerous fire and explosion hazard when exposed to heat or flame. A storage hazard. It auto-oxidizes to form explosive polymeric 1 -oxy-peroxides. Explosive reaction with boron triazide, bromine trifluoride, bromine pentafluoride, perchloric acid, uranyl nitrate + light, wood pulp extracts + heat. Violent reaction or igmtion on contact with halogens (e.g., bromine, chlorine), interhalogens (e.g., iodine heptafluoride), oxidants (e.g., silver perchlorate, nitrosyl perchlorate, nitryl perchlorate, chromyl chloride, fluorine nitrate, permanganic acid, nitric acid, hydrogen peroxide, peroxodisulfuric acid, iodine(VⅡ) oxide, solum peroxide, ozone, and liquid air), sulfur and sulfur compounds (e.g., sulfur when dried with peroxidzed ether, sulfuryl chloride). Can react vigorously with acetyl peroxide, air, bromoazide, ClF3, CrO3, Cr(OCl)2, LiAlH2, NOClO4,02, NClO2, (H2so4 + permanganates), K2O2, [(C2H5)3di + air], [(CH3)d + air]. To fight fire, use alcohol foam, CO2, dry chemical. Used in production of drugs of abuse. When heated to decomposition it emits acrid smoke and irritating fumes. See also ETHERS.

Potential Exposure

Ethyl ether is used as a solvent for waxes, fats, oils, perfumes, alkaloids, dyes, gums, resins, nitrocellulose, hydrocarbons, raw rubber, and smokeless powder. It is also used as an inhalation anesthetic; a refrigerant; in diesel fuels; in dry cleaning; as an extractant; and as a chemical reagent for various organic reactions

Environmental fate

Photolytic. The rate constant for the reaction of ethyl ether and OH radicals in the atmosphere at 300 K is 5.4 x 10-12 cm3/molecule?sec (Hendry and Kenley, 1979). Chemical/Physical. The atmospheric oxidation of ethyl ether by OH radicals in the presence of nitric oxide yielded ethyl formate as the major product. Minor products included formaldehyde and nitrogen dioxide. In the absence of nitric oxide, the products were ethyl formate and acetaldehyde (Wallington and Japar, 1991). Ethyl ether will not hydrolyze (Kollig, 1993).

storage

ether should be used only in areas free of ignition sources (including hot plates, incandescent light bulbs, and steam baths), and this substance should be stored in tightly sealed metal containers in areas separate from oxidizers. Because of the tendency of diethyl ether to form peroxides on contact with air, containers should be dated upon receipt and at the time they are opened. Diethyl ether is generally supplied with additives that inhibit peroxide formation; distillation removes these inhibitors and renders the liquid more prone to peroxide formation. Material found to contain peroxides should be treated to destroy the peroxides before use or disposed of properly.

Shipping

UN1155 Diethyl ether or Ethyl ether, Hazard Class: 3; Labels: 3-Flammable liquid

Purification Methods

Usual impurities are water, EtOH, diethyl peroxide (which is explosive when concentrated), and aldehydes. Peroxides [detected by liberation of iodine from weakly acid (HCl) solutions of KI, or by the blue colour in the ether layer when 1mg of Na2Cr2O7 and 1 drop of dilute H2SO4 in 1mL of water is shaken with 10mL of ether] can be removed in several different ways. The simplest method is to pass dry ether through a column of activated alumina (80g Al2O3/700mL of ether). More commonly, 1L of ether is shaken repeatedly with 5-10mL of a solution comprising 6.0g of ferrous sulfate and 6mL of conc H2SO4 in 110mL of water. Aqueous 10% Na2SO3 or stannous chloride can also be used. The ether is then washed with water, dried for 24hours with CaCl2, filtered and dried further by adding sodium wire until it remains bright. The ether is stored in a dark cool place, until distilled from sodium before use. Peroxides can also be removed by wetting the ether with a little water, then adding excess LiAlH4 or CaH2 and leaving to stand for several hours. (This also dried the ether.) Werner [Analyst 58 335 1933] removed peroxides and aldehydes by adding 8g AgNO3 in 60mL of water to 1L of ether, then 100mL of 4% NaOH and shaking for 6minutes. Fierz-David [Chimia 1 246 1947] shook 1L of ether with 10g of a zinc-copper couple. (This reagent is prepared by suspending zinc dust in 50mL of hot water, adding 5mL of 2M HCl and decanting after 20seconds, washing twice with water, covering with 50mL of water and 5mL of 5% cuprous sulfate with swirling. The liquid is decanted and discarded, and the residue is washed three times with 20mL of ethanol and twice with 20mL of diethyl ether). Aldehydes can be removed from diethyl ether by distillation from hydrazine hydrogen sulfate, phenyl hydrazine or thiosemicarbazide. Peroxides and oxidisable impurities have also been removed by shaking with strongly alkaline-saturated KMnO4 (with which the ether was left to stand in contact for 24hours), followed by washing with water, conc H2SO4, water again, then drying (CaCl2) and distillation from sodium, or sodium containing benzophenone to form the ketyl. Other purification procedures include distillation from sodium triphenylmethide or butyl magnesium bromide, and drying with solid NaOH or P2O5. [Beilstein 1 IV 1314.] Rapid purification: Same as for 1,4-dioxane.

Toxicity evaluation

Inhalation is the main route of exposure to diethyl ether. Occupational exposure to diethyl ether may occur through inhalation and dermal contact with this compound at workplaces where diethyl ether is used. Exposure to this chemical may also occur via inhalation of ambient air and ingestion of contaminated drinking water. Although rare, intentional (suicidal) exposure is also reported. The industrial use of diethyl ether may result in its release to the environment through various waste streams. In air, diethyl ether will exist as a vapor and will be degraded in the atmosphere after reacting with hydroxyl and nitrate radicals. Halflives of these reactions in air are estimated to be 1.2 and 5.8 days, respectively. In soil and water, diethyl ether is expected to volatilize and biodegradation is likely to be a slow process. Bioconcentration of diethyl ether in aquatic organisms is low.

Incompatibilities

May form explosive mixture with air. Incompatible with strong acids; strong oxidizers halogens, sulfur, sulfur compounds, causing fire and explosion hazard. Can form peroxides from air, heat, sunlight; may explode when container is unstoppered or otherwise opened. Attacks some plastics, rubber and coatings. Being a nonconductor, chemical may accumulate static electric charges that may result in ignition of vapor.

Waste Disposal

Concentrated waste containing no peroxides-discharge liquid at a controlled rate near a pilot flame. Concentrated waste containing peroxidesperforation of a container of the waste from a safe distance followed by open burning. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal

Check Digit Verification of cas no

The CAS Registry Mumber 60-29-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 60-29:
(4*6)+(3*0)+(2*2)+(1*9)=37
37 % 10 = 7
So 60-29-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3

60-29-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Diethyl ether

1.2 Other means of identification

Product number -
Other names Ethane, 1,1‘-oxybis-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food Additives: EXTRACTION_SOLVENT
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:60-29-7 SDS

60-29-7Synthetic route

ethanol
64-17-5

ethanol

diethyl ether
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;
ethanol
64-17-5

ethanol

A

diethyl ether
60-29-7

diethyl ether

B

ethene
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%
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

1-ethyl-3-methyl-1H-imidazol-3-ium chloride
65039-09-0

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

A

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate
377739-43-0

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

B

diethyl ether
60-29-7

diethyl ether

C

chloroethane
75-00-3

chloroethane

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

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

N,N,N',N',N'',N''-hexamethylguanidinium chloride
30388-20-6

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

A

hexamethylguanidinium tris(pentafluoroethyl)trifluorophosphate

hexamethylguanidinium tris(pentafluoroethyl)trifluorophosphate

B

diethyl ether
60-29-7

diethyl ether

C

chloroethane
75-00-3

chloroethane

Conditions
ConditionsYield
at 80℃; for 3h;A 98.9%
B n/a
C n/a
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

1-ethyl-3-methylimidazolium hexafluorophosphate
155371-19-0

1-ethyl-3-methylimidazolium hexafluorophosphate

A

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate
377739-43-0

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

B

diethyl ether
60-29-7

diethyl ether

C

1-fluoroethane
353-36-6

1-fluoroethane

D

phosphorus pentafluoride
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
triethyloxonium bis(trifluoromethylsulfonyl)imide
945614-34-6

triethyloxonium bis(trifluoromethylsulfonyl)imide

1-cyano-4-N,N-dimethylaminopyridinium bromide
59016-54-5

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

A

ethyl bromide
74-96-4

ethyl bromide

B

diethyl ether
60-29-7

diethyl ether

C

1-cyano-4-dimethylaminopyridinium bis(trifluoromethylsulfonyl)imide
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%
triethyloxonium bis(trifluoromethylsulfonyl)imide
945614-34-6

triethyloxonium bis(trifluoromethylsulfonyl)imide

1-ethyl-3-methyl-1H-imidazol-3-ium chloride
65039-09-0

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

A

diethyl ether
60-29-7

diethyl ether

B

chloroethane
75-00-3

chloroethane

C

1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
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%
Dimethylphenylsilane
766-77-8

Dimethylphenylsilane

paracetaldehyde
123-63-7

paracetaldehyde

A

diethyl ether
60-29-7

diethyl ether

B

1,1,3,3-tetramethyl-1,3-diphenyldisiloxane
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%
ethyl acetate
141-78-6

ethyl acetate

A

diethyl ether
60-29-7

diethyl ether

B

ethoxytriethylsilane
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)

bis(pentamethylcyclopentadienyl)ytterbium(diethyl ether)

tetraethyldiphosphine disulfide
3790-23-6

tetraethyldiphosphine disulfide

A

((CH3)5C5)2Yb(S2P(C2H5)2)
115018-02-5

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

B

diethyl ether
60-29-7

diethyl ether

C

1,1,2,2-tetraethyldiphosphane
3040-63-9

1,1,2,2-tetraethyldiphosphane

D

tetraethyldiphosphane monosulfide

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
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

1-decyl-3-methylimidazol-3-ium chloride

1-decyl-3-methylimidazol-3-ium chloride

A

diethyl ether
60-29-7

diethyl ether

B

chloroethane
75-00-3

chloroethane

C

1-decyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate
916807-26-6

1-decyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate

Conditions
ConditionsYield
at 80℃; for 3h;A n/a
B n/a
C 96%
methyldiphenylsilane
776-76-1

methyldiphenylsilane

paracetaldehyde
123-63-7

paracetaldehyde

A

diethyl ether
60-29-7

diethyl ether

B

1,3-Dimethyl-1,1,3,3-tetraphenyldisiloxan
807-28-3

1,3-Dimethyl-1,1,3,3-tetraphenyldisiloxan

Conditions
ConditionsYield
With (pentamethylcyclopentadienyl)Ge(II)+B(ArF)4- In dichloromethane-d2 at 50℃; Catalytic behavior;A n/a
B 96%
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

trityl chloride
76-83-5

trityl chloride

A

diethyl ether
60-29-7

diethyl ether

B

chloroethane
75-00-3

chloroethane

C

tritylium tris(pentafluoroethyl)trifluorophosphate

tritylium tris(pentafluoroethyl)trifluorophosphate

Conditions
ConditionsYield
at 80℃; for 10h;A n/a
B n/a
C 93.6%
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

1-cyano-4-N,N-dimethylaminopyridinium bromide
59016-54-5

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

A

ethyl bromide
74-96-4

ethyl bromide

B

diethyl ether
60-29-7

diethyl ether

C

1-cyano-4-dimethylaminopyridinium tris(pentafluoroethyl)trifluorophosphate
945614-37-9

1-cyano-4-dimethylaminopyridinium tris(pentafluoroethyl)trifluorophosphate

Conditions
ConditionsYield
at 60℃; for 5h;A n/a
B n/a
C 93.2%
N-(n-hexyl)-N-methylpyrrolidinium chloride

N-(n-hexyl)-N-methylpyrrolidinium chloride

triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

A

diethyl ether
60-29-7

diethyl ether

B

chloroethane
75-00-3

chloroethane

C

1-hexyl-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate
945614-40-4

1-hexyl-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate

Conditions
ConditionsYield
at 80℃; for 3h;A n/a
B n/a
C 93%
Diethyl carbonate
105-58-8

Diethyl carbonate

A

diethyl ether
60-29-7

diethyl ether

B

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With NaX faujasite at 180 - 240℃; for 6h;A 93%
B 5%
ethene
74-85-1

ethene

acetic acid
64-19-7

acetic acid

A

diethyl ether
60-29-7

diethyl ether

B

ethanol
64-17-5

ethanol

C

ethyl acetate
141-78-6

ethyl acetate

Conditions
ConditionsYield
Stage #1: acetic acid With water at 92.4℃;
Stage #2: ethene; cesium nitrate; tungstophosphoric acid; water; mixture of, dried, tabletted at 92.4 - 194.4℃; under 6750.68 Torr; Product distribution / selectivity; Gas phase;
A 3.2%
B 3.6%
C 92.7%
With water; cesium nitrate; tungstophosphoric acid; water; mixture of, dried, tabletted at 92.4 - 165℃; under 6750.68 Torr; Product distribution / selectivity; Gas phase;A 3%
B 3.4%
C 91.5%
With water; lithium nitrate; silica; tungstophosphoric acid; water; mixture of, heated at 150 C at 102.2 - 165℃; under 6750.68 Torr; Product distribution / selectivity; Gas phase;A 2.2%
B 5%
C 90.1%
With water; lithium nitrate; silica; tungstosilicic acid; water; mixture of, heated at 150 C at 102.2 - 165℃; under 6750.68 Torr; Conversion of starting material; Gas phase;A 4.7%
B 7.6%
C 87.7%
ethene
74-85-1

ethene

acrylic acid
79-10-7

acrylic acid

A

diethyl ether
60-29-7

diethyl ether

B

ethanol
64-17-5

ethanol

C

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With water; cesium nitrate; tungstophosphoric acid; water; mixture of, dried, tabletted at 85.6 - 165℃; under 2250.23 Torr; Product distribution / selectivity; Gas phase;A 3.5%
B 4.3%
C 91.8%
ethanol
64-17-5

ethanol

1,3-bis(p-nitrophenyl)-2-thia-1,3-diazaallene
15148-19-3

1,3-bis(p-nitrophenyl)-2-thia-1,3-diazaallene

A

diethyl ether
60-29-7

diethyl ether

B

diethyl sulphite
623-81-4

diethyl sulphite

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With copper dichloride for 24h; Product distribution; Ambient temperature; other reagent;A 93.6 % Chromat.
B 70%
C 91%
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

1-ethyl-3-methylimidazolium tetrafluoroborate
143314-16-3

1-ethyl-3-methylimidazolium tetrafluoroborate

A

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate
377739-43-0

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

B

diethyl ether
60-29-7

diethyl ether

C

1-fluoroethane
353-36-6

1-fluoroethane

D

boron trifluoride
7637-07-2

boron trifluoride

Conditions
ConditionsYield
at 100℃; for 10h; Product distribution / selectivity;A 90.3%
B n/a
C n/a
D n/a
diethyl ether
60-29-7

diethyl ether

hexafluoro-3-oxatricyclo<3.2.0.02,4>hept-6-ene
74415-68-2

hexafluoro-3-oxatricyclo<3.2.0.02,4>hept-6-ene

A

1-fluoroethane
353-36-6

1-fluoroethane

B

pentafluoro-2-ethoxycyclohexa-2,5-dienone

pentafluoro-2-ethoxycyclohexa-2,5-dienone

Conditions
ConditionsYield
for 2160h; Ambient temperature;A 100%
B 75%
for 2160h; Yields of byproduct given;A n/a
B 21%
diethyl ether
60-29-7

diethyl ether

A

1-fluoroethane
353-36-6

1-fluoroethane

B

pentafluoro-2-ethoxycyclohexa-2,5-dienone

pentafluoro-2-ethoxycyclohexa-2,5-dienone

Conditions
ConditionsYield
With hexafluoro-3-oxatricyclo<3.2.0.02,4>hept-6-ene for 2160h; Ambient temperature;A 100%
B 75%
diethyl ether
60-29-7

diethyl ether

trifluoroacetyl triflate
68602-57-3

trifluoroacetyl triflate

A

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

B

trifluoromethanesulfonic acid ethyl ester
425-75-2

trifluoromethanesulfonic acid ethyl ester

Conditions
ConditionsYield
at 0℃;A 100%
B 100%
diethyl ether
60-29-7

diethyl ether

2,3-bis(dimethylsilyl)-1,1,4,4-tetramethyl-1,4-disila-1,4-dihydronaphthalene

2,3-bis(dimethylsilyl)-1,1,4,4-tetramethyl-1,4-disila-1,4-dihydronaphthalene

[2,3-bis(dimethylsilyl)-1,1,4,4-tetramethyl-1,4-disila-1,4-dihydronaphthalenato]bis[(diethyl ether)lithium(I)]

[2,3-bis(dimethylsilyl)-1,1,4,4-tetramethyl-1,4-disila-1,4-dihydronaphthalenato]bis[(diethyl ether)lithium(I)]

Conditions
ConditionsYield
With lithium at 20℃; for 20h; Reduction;100%
diethyl ether
60-29-7

diethyl ether

2,3,6,7-tetrakis(dimethylsilyl)-1,1,4,4,5,5,8,8-octamethyl-1,4,5,8-tetrasila-1,4,5,8-tetrahydroanthracene

2,3,6,7-tetrakis(dimethylsilyl)-1,1,4,4,5,5,8,8-octamethyl-1,4,5,8-tetrasila-1,4,5,8-tetrahydroanthracene

[2,3,6,7-tetrakis(dimethylsilyl)-1,1,4,4,5,5,8,8-octamethyl-1,4,5,8-tetrasila-1,4,5,8-tetrahydroanthracenato]tetrakis[(diethyl ether)lithium(I)]

[2,3,6,7-tetrakis(dimethylsilyl)-1,1,4,4,5,5,8,8-octamethyl-1,4,5,8-tetrasila-1,4,5,8-tetrahydroanthracenato]tetrakis[(diethyl ether)lithium(I)]

Conditions
ConditionsYield
With lithium at 20℃; for 20h; Reduction;100%
diethyl ether
60-29-7

diethyl ether

2-(trifluoromethyl)phenol
444-30-4

2-(trifluoromethyl)phenol

1,4-bis(bromomethyl)-2,5-dibromobenzene
35335-16-1

1,4-bis(bromomethyl)-2,5-dibromobenzene

1,4-dibromo-2,5-bis(2-trifluoromethylphenoxymethyl)benzene
474330-25-1

1,4-dibromo-2,5-bis(2-trifluoromethylphenoxymethyl)benzene

Conditions
ConditionsYield
With sodium hydroxide; potassium carbonate In dichloromethane; acetone100%
4-[[[4-[4-(ethyloxycarbonyl)-1-piperazinyl]phenyl]amino]carbonyl]-1-t-butyloxycarbonyl-piperidine
193902-67-9

4-[[[4-[4-(ethyloxycarbonyl)-1-piperazinyl]phenyl]amino]carbonyl]-1-t-butyloxycarbonyl-piperidine

diethyl ether
60-29-7

diethyl ether

4-[[[4-[4-(ethyloxycarbonyl)-1-piperazinyl]phenyl]amino]carbonyl]piperidine
193902-68-0

4-[[[4-[4-(ethyloxycarbonyl)-1-piperazinyl]phenyl]amino]carbonyl]piperidine

Conditions
ConditionsYield
In 1,4-dioxane; hydrogenchloride100%
diethyl ether
60-29-7

diethyl ether

phenol
108-95-2

phenol

2-phenoxytetrahydropyran
4203-50-3

2-phenoxytetrahydropyran

Conditions
ConditionsYield
With hydrogenchloride In 3,4-dihydro-2H-pyran100%
oxalyl dichloride
79-37-8

oxalyl dichloride

diethyl ether
60-29-7

diethyl ether

3,3-diphenylpropan-1-ol
20017-67-8

3,3-diphenylpropan-1-ol

3,3-diphenylpropanal
4279-81-6

3,3-diphenylpropanal

Conditions
ConditionsYield
With dimethyl sulfoxide; triethylamine In dichloromethane100%
2-(2-ethyl-benzofuran-3-yl)-propionic acid
63606-55-3

2-(2-ethyl-benzofuran-3-yl)-propionic acid

diethyl ether
60-29-7

diethyl ether

2-(2-ethyl-benzofuran-3-yl)-propionamide
63606-56-4

2-(2-ethyl-benzofuran-3-yl)-propionamide

Conditions
ConditionsYield
In thionyl chloride100%
diethyl ether
60-29-7

diethyl ether

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

2-(dimethylamino)benzyllithium
64308-58-3

2-(dimethylamino)benzyllithium

Conditions
ConditionsYield
With n-butyllithium In hexane100%
With n-butyllithium In hexane
diethyl ether
60-29-7

diethyl ether

trans-dichloro(ethylene)(2,4,6-trimethylpyridine)platinum
52341-13-6, 12264-20-9

trans-dichloro(ethylene)(2,4,6-trimethylpyridine)platinum

trans-dichloro(diethyl ether)(2,4,6-trimethylpyridine)platinum(II)
91068-18-7

trans-dichloro(diethyl ether)(2,4,6-trimethylpyridine)platinum(II)

Conditions
ConditionsYield
In diethyl ether byproducts: ethylene; Irradiation (UV/VIS);100%
In diethyl ether Irradiation (UV/VIS); the Pt-complex dissolved in Et2O was introduced into a muffshaped Schlenk tube surrounding a 125-W medium-pressure mercury lamp, Philips HPK 125, irradn. for 15 min at room temp., λ<310 nm was eliminated by Pyrex filter; the solvent was removed under reduced pressure at -30°C, the solid was recrystd. at -30°C in pentane-CH2Cl2;95%
diethyl ether
60-29-7

diethyl ether

dimethylgallium tetrahydroborate

dimethylgallium tetrahydroborate

(CH3)2GaBH4(CH3CH2)2O
326903-59-7

(CH3)2GaBH4(CH3CH2)2O

Conditions
ConditionsYield
In diethyl ether (high vac. line); condensing gallium complex in an ampoule with Et2O, warming to room temp. over a period of 30 min; fractionation, collection in a trap at -30°C;100%
diethyl ether
60-29-7

diethyl ether

[(C5H4N)C(CH3)(CH2N(C6H2(CH3)3))2]Zr(CH3)2
293764-40-6

[(C5H4N)C(CH3)(CH2N(C6H2(CH3)3))2]Zr(CH3)2

methyllithium
917-54-4

methyllithium

[C5H4NC(CH3)(CH2NC6H2(CH3)3)2]Zr(methyl)3[Li*diethyl ether]
486413-21-2

[C5H4NC(CH3)(CH2NC6H2(CH3)3)2]Zr(methyl)3[Li*diethyl ether]

Conditions
ConditionsYield
In diethyl ether N2; addn. of methyllithium as 4.4 M ether soln. to ether suspn. of Zr complex at -30° C, stirring at room temp. for 10 min; filtration through Celite, drying the filtrate in vac.; elem. anal.;100%
diethyl ether
60-29-7

diethyl ether

bis[bis(pentamethylcyclopentadienyl)(μ-hydride)yttrium]

bis[bis(pentamethylcyclopentadienyl)(μ-hydride)yttrium]

benzene-d6
1076-43-3

benzene-d6

A

((CH3)5C5)2Y(OC2H5)
165269-59-0

((CH3)5C5)2Y(OC2H5)

B

((CH3)5C5)2Y(D)((C2H5)2O)

((CH3)5C5)2Y(D)((C2H5)2O)

Conditions
ConditionsYield
In diethyl ether; benzene-d6 byproducts: ethane; N2-atmosphere; room temp. (20 min);A 100%
B n/a
diethyl ether
60-29-7

diethyl ether

[La(η5-C5(CH3)5)H]2
98720-39-9

[La(η5-C5(CH3)5)H]2

((CH3)5C5)2La(OC2H5)(O(C2H5)2)
165269-60-3

((CH3)5C5)2La(OC2H5)(O(C2H5)2)

Conditions
ConditionsYield
In benzene-d6 byproducts: ethane; N2-atmosphere; room temp. (10 min); evapn. (vac.);100%
diethyl ether
60-29-7

diethyl ether

supersilylgallium dichloride, dimer

supersilylgallium dichloride, dimer

supersilylgallium dichloride-diethyl ether (1/1)

supersilylgallium dichloride-diethyl ether (1/1)

Conditions
ConditionsYield
In dichloromethane (inert conditions); removal of volatiles (vac.);100%
lithium aluminium tetrahydride
16853-85-3

lithium aluminium tetrahydride

diethyl ether
60-29-7

diethyl ether

Gallium trichloride
13450-90-3

Gallium trichloride

gallane etherate

gallane etherate

Conditions
ConditionsYield
In diethyl ether (N2), GaCl3 in Et2O added dropwise to soln. of LiAlH4 in Et2O at 0°C, stirred at 0°C for 2 h; stored overnight at -20°C, filtered cold, evapd. at -78°C;100%
diethyl ether
60-29-7

diethyl ether

C20H30O6

C20H30O6

A

(1S,3aR,5S,5'S,6R,6a'R)-2,2'-dimethyl-5'-(2-methyl-1,3-dioxolan-4-yl)dihydro-3a'H-3-oxaspiro[bicyclo[3.2.0.]heptane-6,6'-furo[2,3-d][1,3]dioxole]
1244773-04-3

(1S,3aR,5S,5'S,6R,6a'R)-2,2'-dimethyl-5'-(2-methyl-1,3-dioxolan-4-yl)dihydro-3a'H-3-oxaspiro[bicyclo[3.2.0.]heptane-6,6'-furo[2,3-d][1,3]dioxole]

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate); benzene Inert atmosphere; Irradiation;A 65%
B 100%
diethyl ether
60-29-7

diethyl ether

bis(trimethylsilyl)-trifluoromethylsulfonium tetrakis(pentafluorophenyl)borate
1235436-62-0

bis(trimethylsilyl)-trifluoromethylsulfonium tetrakis(pentafluorophenyl)borate

diethyl(trimethylsilyl)oxonium tetrakis(pentafluorophenyl)borate

diethyl(trimethylsilyl)oxonium tetrakis(pentafluorophenyl)borate

Conditions
ConditionsYield
react. bis(trimethylsilyl)-trifluoromethylsulfonium tetrakis(pentafluorophenyl)borate with Et2O;100%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

benzophenone
119-61-9

benzophenone

diethyl ether
60-29-7

diethyl ether

C18H23IMgO2

C18H23IMgO2

Conditions
ConditionsYield
at 20℃; for 12h;100%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

diethyl ether
60-29-7

diethyl ether

acetophenone
98-86-2

acetophenone

C13H21IMgO2

C13H21IMgO2

Conditions
ConditionsYield
at 20℃; for 12h;100%
diethyl ether
60-29-7

diethyl ether

Cp*Ru(μ-SnC4Et4)2RuCp*

Cp*Ru(μ-SnC4Et4)2RuCp*

lithium
7439-93-2

lithium

[Li(Et2O)]2[Cp*Ru(μ-SnC4Et4)2RuCp*]

[Li(Et2O)]2[Cp*Ru(μ-SnC4Et4)2RuCp*]

Conditions
ConditionsYield
at 20℃; for 1h; Inert atmosphere;100%
diethyl ether
60-29-7

diethyl ether

Ce(decafluorodiphenylamide)3

Ce(decafluorodiphenylamide)3

Ce(decafluorodiphenylamide)3(diethyl ether)2
1445605-48-0

Ce(decafluorodiphenylamide)3(diethyl ether)2

Conditions
ConditionsYield
for 0.5h; Inert atmosphere;100%
chloro(1,5-cyclooctadiene)rhodium(I) dimer

chloro(1,5-cyclooctadiene)rhodium(I) dimer

diethyl ether
60-29-7

diethyl ether

(R,Rb)-[1,1'-binaphthalene]-2,2'-diyl(2'-methoxy-[1,1'-binaphthalen]-2-yl)phosphonite
1365891-80-0, 1365891-81-1

(R,Rb)-[1,1'-binaphthalene]-2,2'-diyl(2'-methoxy-[1,1'-binaphthalen]-2-yl)phosphonite

[RhCl((R,R)-C41H27O3P)(η4-cod)]*(C2H5)2O
1436385-41-9

[RhCl((R,R)-C41H27O3P)(η4-cod)]*(C2H5)2O

Conditions
ConditionsYield
In dichloromethane for 0.5h; Inert atmosphere; Schlenk technique;100%
diethyl ether
60-29-7

diethyl ether

bis(3,5-di-tert-butyl-2-phenol)amine trilithium salt

bis(3,5-di-tert-butyl-2-phenol)amine trilithium salt

tantalum pentachloride
7721-01-9

tantalum pentachloride

(bis(3,5-di-tert-butyl-2-phenol)amine-3H)TaCl2(Et2O)

(bis(3,5-di-tert-butyl-2-phenol)amine-3H)TaCl2(Et2O)

Conditions
ConditionsYield
In toluene Inert atmosphere; Glovebox;100%
morpholine
110-91-8

morpholine

diethyl ether
60-29-7

diethyl ether

N-ethylmorpholine;
100-74-3

N-ethylmorpholine;

Conditions
ConditionsYield
With alumina at 270℃; under 760.051 Torr; Inert atmosphere; Gas phase; Green chemistry;100%
diethyl ether
60-29-7

diethyl ether

Mo2[μ-κ2-PhB(N-2,6-iPr2C6H3)2]2

Mo2[μ-κ2-PhB(N-2,6-iPr2C6H3)2]2

[(tetrahydrofuran)2K18-C-6]2[Mo2{μ-κ2-PhB(2,6-iPr2C6H3)2}2]

[(tetrahydrofuran)2K18-C-6]2[Mo2{μ-κ2-PhB(2,6-iPr2C6H3)2}2]

[(Et2O)K18-C-6][Mo2{μ-κ2-PhB(N-2,6-iPr2C6H3)2}2]

[(Et2O)K18-C-6][Mo2{μ-κ2-PhB(N-2,6-iPr2C6H3)2}2]

Conditions
ConditionsYield
at -35 - 20℃; Inert atmosphere;100%
diethyl ether
60-29-7

diethyl ether

ethylene dibromide
106-93-4

ethylene dibromide

magnesium bromide diethyl etherate
29858-07-9

magnesium bromide diethyl etherate

Conditions
ConditionsYield
With magnesium Heating;100%

60-29-7Relevant articles and documents

Ethylation of Ethanol in the Gas Phase

Audier, H. E.,Monteiro, C.,Robin, D.

, p. 146 (1989)

-

Study of the Ethylation of Ethanol by Using a Dual-cell Fourier Transform Mass Spectrometer

Bjarnason, Asgeir

, p. 847 - 848 (1989)

-

Heterogeneous Parahydrogen-Induced Polarization of Diethyl Ether for Magnetic Resonance Imaging Applications

Salnikov, Oleg G.,Svyatova, Alexandra,Kovtunova, Larisa M.,Chukanov, Nikita V.,Bukhtiyarov, Valerii I.,Kovtunov, Kirill V.,Chekmenev, Eduard Y.,Koptyug, Igor V.

, p. 1316 - 1322 (2021)

Magnetic resonance imaging (MRI) with the use of hyperpolarized gases as contrast agents provides valuable information on lungs structure and function. While the technology of 129Xe hyperpolarization for clinical MRI research is well developed, it requires the expensive equipment for production and detection of hyperpolarized 129Xe. Herein we present the 1H hyperpolarization of diethyl ether vapor that can be imaged on any clinical MRI scanner. 1H nuclear spin polarization of up to 1.3 % was achieved using heterogeneous hydrogenation of ethyl vinyl ether with parahydrogen over Rh/TiO2 catalyst. Liquefaction of diethyl ether vapor proceeds with partial preservation of hyperpolarization and prolongs its lifetime by ≈10 times. The proof-of-principle 2D 1H MRI of hyperpolarized diethyl ether was demonstrated with 0.1×1.1 mm2 spatial and 120 ms temporal resolution. The long history of use of diethyl ether for anesthesia is expected to facilitate the clinical translation of the presented approach.

THE SURFACE STRUCTURE AND CATALYTIC PROPERTIES OF ONE-ATOMIC LAYER AMORPHOUS NIOBIUM-OXIDE ATTACHED ON SiO2

Asakura, Kiyotaka,Twasawa, Yasuhiro

, p. 859 - 862 (1986)

A SiO2-attached one-atomic layer amorphous niobium-oxide catalyst was prepared by the two-stage attaching reaction between silanol groups and Nb(OC2H5)5 followed by chemical treatments with H2O and O2.The one-atomiclayer Nb oxide catalyst was found to be active and selective for ethene formation from ethanol.

-

Skaerblom

, (1928)

-

Solvent effects in liquid-phase dehydration reaction of ethanol to diethylether catalysed by sulfonic-acid catalyst

Vanoye, Laurent,Zanota, Marie-Line,Desgranges, Audrey,Favre-Reguillon, Alain,De Bellefon, Claude

, p. 276 - 280 (2011)

The liquid-phase dehydration of ethanol to diethylether over heterogeneous sulfonic-acid catalysts was carried out in a stirred batch reactor. The different Amberlyst catalysts were found to have similar activities for this reaction; even though Amberlyst 70 showed a lower acid capacity compensated by a higher specific activity. By comparing the conversion of ethanol as a function of reaction mixture composition, it was found that reaction rates greatly depended on ethanol concentration but also on reaction mixture polarity. The swelling of the used resins could not explain the observed variations of initial reaction rate since this effect was observed both with resins and with homogeneous catalyst, i.e. p-toluenesulfonic acid. The initial ethanol concentration has a complex effect on initial reaction rates that could not be correlated by usual kinetic models. Taking account of the intrinsic reactivity trends of the SN2 etherification reaction, a strong dependence was found between solvent properties and initial reaction rate.

Conversion of ethanol and glycerol to olefins over the Re- and W-containing catalysts

Zharova,Chistyakov,Zavelev,Kriventsov,Yakimchuk,Kryzhovets,Petrakova,Drobot,Tsodikov

, p. 337 - 345 (2015)

The catalytic conversion of a mixture of ethanol and glycerol over the Re - W/Al2O3 catalysts was studied. The Re - W binary system exhibits a non-additive cocatalytic effect in the conversion of ethanol and its mixture with glycerol into the fraction of olefins C4 - C9. The non-additive increase in the catalytic activity is associated with the specific structure of the binuclear metallocomplex precursors, due to which the supported metals are arranged in the immediate vicinity from each other on the support surface and intensively interact to form Re7+. The study of the combined conversion of ethanol and glycerol made it possible to find an optimum ratio of the reactants in the initial mixture. The yield of target hydrocarbons attains 50 wt.% based on the amount of carbon passed through the reactor.

Catalytic activity of heteropoly tungstate catalysts for ethanol dehydration reaction: Deactivation and regeneration

Verdes, Orsina,Sasca, Viorel,Popa, Alexandru,Suba, Mariana,Borcanescu, Silvana

, p. 123 - 132 (2021)

The pure and palladium doped 12-tungstophosphoric acid - H3PW12O40 (HPW) and its cesium salts CsxH3-xPW12O40 (x = 1, 2, 2.25 and 2.5) were prepared and characterized by thermal analysis, FTIR, XRD, BET and XPS methods. In this paper were determined the optimal reaction temperature and the effect of palladium on the coke content during the dehydration of ethanol in the temperature range of 200?350 °C. Above 300 °C, a strong deactivation of the catalysts was caused by coke formation. The catalytic tests demonstrate that by supporting the HPW and PdyPW (y = 0.15, 0.2 and 0.25) on mesoporous molecular sieve SBA-15 the catalytic activity in ethanol dehydration reaction was improved. Palladium doping of HPW/SBA-15 significantly decreases the formation of coke deposit. The formation of coke during the ethanol dehydration does not affect the Keggin structure which led us to conclude that such catalysts can be regenerated in air and regain their catalytic activity for a short time.

An Unusually Acidic and Thermally Stable Cesium Titanate CsxTi2- yMyO4 (x = 0.67 or 0.70; M = vacancy or Zn)

Maluangnont, Tosapol,Wuttitham, Boonyawat,Hongklai, Panisa,Khunmee, Pongsatorn,Tippayasukho, Sorawat,Chanlek, Narong,Sooknoi, Tawan

, p. 6885 - 6892 (2019)

Proton-free, alkali-containing layered metal oxides are thermally stable compared to their protonic counterparts, potentially allowing catalysis by Lewis acid sites at elevated temperatures. However, the Lewis acidic nature of these materials has not been well explored, as alkali ions are generally considered to promote basic but to suppress acidic character. Here, we report a rare example of an unusually acidic cesium-containing oxide CsxTi2-yMyO4 (x = 0.67 or 0.70; M = Ti vacancy or Zn). These lepidocrocite-type microcrystals desorbed NH3 at >400 °C with a total acidity of 410 μmol g-1 at a specific surface area of only 5 m2 g-1, without the need for lengthy proton-ion exchange, pillaring, delamination, or restacking. The soft and easily polarized Cs+ ion essentially drives the formation of the Lewis acidic site on the surfaces as suggested by IR of sorbed pyridine. The two-dimensional layered structure was preserved after the oxide was employed in the ethanol conversion at 380 °C, the temperature at which the protonic form could have converted to anatase. The structure was also retained after the NH3 temperature-programmed desorption measurement up to 700 °C. The production of ethylene from ethanol, well-known to occur over acid sites, unambiguously confirmed the acidic nature of this cesium titanate.

Gilman et al.

, p. 1034,1038,1039 (1954)

A study of commercial transition aluminas and of their catalytic activity in the dehydration of ethanol

Phung, Thanh Khoa,Lagazzo, Alberto,Rivero Crespo, Miguel Angel,Sanchez Escribano, Vicente,Busca, Guido

, p. 102 - 113 (2014)

Conversion of ethanol was investigated over four commercial aluminas prepared by different industrial procedures and one commercial silica-alumina. Characterization was performed by TEM, XRD, SBET and porosity measurements, and IR spectroscopy of the surface OH groups and of adsorbed CO and pyridine. Different features are attributed to different phases (γ-, δ-, θ-Al2O3) and different impurities (Na +, Cl-). Total conversion of ethanol with >99% selectivity to ethylene is achieved at 623 K over the purer Al2O 3 catalyst (Na 3+ sites in a tetrahedral environment located on edges and corners of the nanocrystals. Ethanol adsorbs dissociatively on Lewis acid-base pair sites but may also displace water and/or hydroxyl groups from Lewis acidic Al3+ sites forming the active intermediate ethoxy species. Surface ethoxy groups are supposed to be intermediate species for both diethyl ether and ethylene production. Silica-alumina also works as a Lewis acid catalyst. The slightly lower activity on surface area basis of silica-alumina than aluminas attributed to the lower density of Lewis acid sites and the absence of significant basicity.

Catalytic activity of LiZr2(PO4)3 nasicon-type phosphates in ethanol conversion process in conventional and membrane reactors

Ilin, Andrey B.,Orekhova, Natalia V.,Ermilova, Margarita M.,Yaroslavtsev, Andrey B.

, p. 29 - 36 (2016)

In this paper synthesis and catalytic properties of new catalysts based on double lithium-zirconium phosphate (LiZr2(PO4)3) with monoclinic NASICON-type structure, doped by indium, niobium and molybdenum are discussed. The obtained samples with particle size of 50-300 nm were characterized by X-ray diffraction, scanning electron microscopy and X-ray microanalysis. The synthesized samples exhibit catalytic activity in the dehydration and dehydrogenation reactions of ethanol conversion. The main products were acetaldehyde, diethyl ether, hydrogen, C2- and C4-hydrocarbons. Indium- and molibdenum-doped samples were characterized by high activity in dehydrogenation processes, while niobium-doped was more active in dehydration processes. The highest selectivity in diethyl ether formation was achieved for LiZr2(PO4)3 and Nb-doped samples (90 and 60% at 300°C). The highest hydrogen yield (up to 60%) was obtained with the use of In-doped catalyst. LiZr2(PO4)3 and Mo-doped samples are also noticeable for high C4-hydrocarbons formation, selectivity to which reaches 60% at 390°C. Use of a 100% hydrogen selective palladium-ruthenium alloy membrane increases hydrogen yield by 20%.

Novel synthesis of homogenous CsxWO3 nanorods with excellent NIR shielding properties by a water controlled-release solvothermal process

Guo, Chongshen,Yin, Shu,Zhang, Peilin,Yan, Mei,Adachi, Kenji,Chonan, Takeshi,Sato, Tsugio

, p. 8227 - 8229 (2010)

Nanosize homogenous rod-like tungsten bronze CsxWO3 with excellent NIR shielding ability was successfully synthesized by a novel and facile water controlled-release solvothermal process (WCRSP).

Calingaert,Soroos,Hnizda

, p. 392 (1942)

Rigid Arrangements of Ionic Charge in Zeolite Frameworks Conferred by Specific Aluminum Distributions Preferentially Stabilize Alkanol Dehydration Transition States

Bates, Jason S.,Di Iorio, John R.,Gounder, Rajamani,Hibbitts, David,Hoffman, Alexander J.,Nimlos, Claire T.,Nystrom, Steven V.

, p. 18686 - 18694 (2020)

Zeolite reactivity depends on the solvating environments of their micropores and the proximity of their Br?nsted acid sites. Turnover rates (per H+) for methanol and ethanol dehydration increase with the fraction of H+ sites sharing six-membered rings of chabazite (CHA) zeolites. Density functional theory (DFT) shows that activation barriers vary widely with the number and arrangement of Al (1–5 per 36 T-site unit cell), but cannot be described solely by Al–Al distance or density. Certain Al distributions yield rigid arrangements of anionic charge that stabilize cationic intermediates and transition states via H-bonding to decrease barriers. This is a key feature of acid catalysis in zeolite solvents, which lack the isotropy of liquid solvents. The sensitivity of polar transition states to specific arrangements of charge in their solvating environments and the ability to position such charges in zeolite lattices with increasing precision herald rich catalytic diversity among zeolites of varying Al arrangement.

A new method for quantifying iodine in a starch-iodine matrix

Manion, Bruce A.,Holbein, Bruce E.,Marcone, Massimo F.,Seetharaman, Koushik

, p. 2698 - 2704 (2010)

A rapid and sensitive method for quantifying iodine in intact starch granules using gas chromatography is described with detection limits as low as 0.2% (w/w) iodine in starch. Sample preparation includes NaBH4 reduction of the various iodine species associated with starch to the colorless soluble iodide ion, followed by its quantitative derivatization to EtI using Et3O+BF4- in CH2Cl2. Identification and quantification of EtI is carried out by extraction and injection of the EtI so generated in CH2Cl2 into a gas chromatography-mass spectrometer (GC-MS). Routine quantification of EtI was then performed using GC with a flame ionization detector (GC-FID). Results for different iodine:potassium iodide ratios of the initially bound iodine and for seven different starch matrices showed that in all cases regression coefficients for the standards were high (R2 >0.96).

Alvorado

, p. 790 (1928)

EFFECT OF THE NATURE OF THE CARRIER AND REDUCTION CONDITIONS ON THE PROPERTIES OF RHENIUM CATALYSTS OF HYDROGENATION OF ETHYL ACETATE

Avaev, V. I.,Ryashentseva, M. A.,Minachev, Kh. M.

, p. 15 - 19 (1988)

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Direct conversion of ethanol into ethylene oxide on gold-based catalysts: Effect of CeOx and Li2O addition on the selectivity

Lippits,Nieuwenhuys

, p. 142 - 149 (2010)

Results are presented concerning the behavior of alumina-supported gold catalysts and the effects of addition of Li2O and CeOx on the oxidation, dehydrogenation and dehydration reactions of ethanol. Pure alumina mainly acts as an acidic catalyst and produces diethyl ether and ethylene. Gold particles play an important role in converting ethanol into ethylene oxide and acetaldehyde. Addition of Li2O influences the selectivity by suppressing the formation of diethyl ether and ethylene. With the Au/Li2O/Al2O3 catalysts, a high selectivity toward ethylene oxide can be obtained. The influence of the oxygen concentration on the gas flow is investigated. It is suggested that at low concentrations, the role of oxygen is mainly to prevent coke formation on the catalytic surface.

Ethanol dehydration and dehydrogenation on γ-Al2O3: Mechanism of acetaldehyde formation

DeWilde, Joseph F.,Czopinski, Christopher J.,Bhan, Aditya

, p. 4425 - 4433 (2014)

Steady state kinetics and measured pyridine inhibition of ethanol dehydration and dehydrogenation rates on γ-alumina above 623 K show that ethanol dehydrogenation can be described with an indirect hydrogen transfer mechanism to form acetaldehyde and ethane and that this mechanism proceeds through a shared surface intermediate with ethylene synthesis from ethanol dehydration. Ethane is produced at a rate within experimental error of acetaldehyde production, demonstrating that ethane is a coproduct of acetaldehyde synthesis from ethanol dehydrogenation. Steady state kinetic measurements indicate that acetaldehyde synthesis rates above 623 K are independent of co-fed water partial pressure up to 1.7 kPa and possess an ethanol partial pressure dependence between 0 and 1 (Pethanol = 1.0-16.2 kPa), consistent with ethanol dehydrogenation rates being inhibited only by ethanol monomer surface species. The surface density of catalytically active sites for ethylene and diethyl ether production were estimated from in situ pyridine titration experiments to be ~0.2 and ~1.8 sites nm-2, respectively, at 623 K. Primary kinetic isotope effects for ethylene and acetaldehyde are measured only when the C-H bonds of ethanol are deuterated, verifying that C-H bond cleavage is kinetically limiting for both products. The proposed indirect hydrogen transfer model for acetaldehyde synthesis is consistent with experimentally observed reaction rate dependences and kinetic isotope effects and highlights the complementary role of hydrogen adatom removal pathways in the formation of aldehydes on Lewis acidic systems. (Chemical Equation Presented).

A comparative study of direct versus post-synthesis alumination of mesoporous FSM-16 silica

Zimowska,Michalik-Zym,Kry?ciak-Czerwenka,Dula,Socha,Pamin,Bazarnik,Bahranowski,Olejniczak,Lityńska-Dobrzyńska,Serwicka

, p. 623 - 631 (2016)

Al-FSM-16 mesoporous silicas were synthesized either by direct method, from Al-kanemite (Al-FSM-16/D), or by post-synthesis impregnation of purely siliceous FSM-16 with Al(NO3)3 (Al-FSM-16/P) and characterized with XRD, XRF, SEM, TEM, nitrogen sorption isotherms, 27Al and 29Si MAS NMR, FTIR, XPS, NH3-TPD, FTIR of pyridine adsorption and catalytic decomposition of ethanol. Only substitutional Al sites exist in Al-FSM-16/D, while in Al-FSM-16/P some Al remains in extra-lattice positions. Upon transformation of Al-FSM-16/D into hydrogen form a certain amount of extra-framework Al is formed. Direct alumination introduces a higher degree of structural disorder. In Al-FSM-16/D, Al is preferentially accumulated at inner pore walls, while in Al-FSM-16/P external surface is Al-rich. Post-synthesis alumination is more efficient in introducing acid sites into FSM-16. The generated acidity is of Br?nsted and Lewis nature, the latter being stronger than the former.

-

Clark,Graham,Winter

, p. 2753 (1925)

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Method for quantifying redox site densities in metal oxide catalysts: Application to the comparison of turnover frequencies for ethanol oxidative dehydrogenation over alumina-supported VOx, MoOx, and WOx catalysts

Nair, Hari,Baertsch, Chelsey D.

, p. 1 - 4 (2008)

Isothermal anaerobic titration with ethanol as a probe molecule is proposed as an accurate technique to quantify active redox site densities in supported metal oxide catalysts. It is shown that the number of active redox sites for VOx-Al2O3, MoOx-Al2O3, and WOx-Al2O3 catalysts is a function of both the metal atom and its oxide surface density, but the intrinsic redox rate per active site is independent of both of these factors. Thus, the difference in steady-state redox rates per metal atom is due only to differences in the number of redox sites under reaction conditions.

Nanocrystalline h-rth zeolite: An efficient catalyst for the low-temperature dehydration of ethanol to ethene

Lee, Jeong Hwan,Lee, Sujin,Hong, Suk Bong

, p. 2035 - 2039 (2018)

The low-temperature dehydration of bioethanol is an environmentally benign route to ethene production. Here we compare the catalytic properties of a series of cage-based small-pore zeolites with different framework structures, acid strengths, and/or crystallite sizes for ethanol dehydration at 200 8C under wet conditions (H2 O/EtOH = 0.2). Among the zeolites studied here, nanocrystalline H-RTH was found to be considerably more effective than H-mordenite, the best catalyst for this reaction known to date, which can be rationalized by product shape selectivity. Whereas the acidity of this zeolite also plays a crucial role in selectively forming ethene, its nanocrystallinity is primarily responsible for the observed high catalyst durability.

Sulfated zirconia foams synthesized by integrative route combining surfactants, air bubbles and sol-gel transition applied to heterogeneous catalysis

Alves-Rosa, Marinalva A.,Martins, Leandro,Hammer, Peter,Pulcinelli, Sandra H.,Santilli, Celso V.

, p. 6686 - 6694 (2016)

Sulfated zirconia ceramic foams were produced by the sol-gel process using air-liquid foam and surfactants as dual pore templates. The results showed the presence of high porosity (until 93%) and surface area (105 m2 g-1), and a hierarchical structure of pore sizes in the range of macro (between 10 and 76 μm), and meso-scales (?6 nm). The hierarchical porous structure and pore wall texturization of ceramic foams produced by this process, besides the presence of strong acid sites, certify these materials as heterogeneous catalysts for dehydration reactions.

Dehydrogenative ester synthesis from enol ethers and water with a ruthenium complex catalyzing two reactions in synergy

Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Luo, Jie,Milstein, David,Rauch, Michael

supporting information, p. 1481 - 1487 (2022/03/07)

We report the dehydrogenative synthesis of esters from enol ethers using water as the formal oxidant, catalyzed by a newly developed ruthenium acridine-based PNP(Ph)-type complex. Mechanistic experiments and density functional theory (DFT) studies suggest that an inner-sphere stepwise coupled reaction pathway is operational instead of a more intuitive outer-sphere tandem hydration-dehydrogenation pathway.

Low-Flammable Parahydrogen-Polarized MRI Contrast Agents

Ariyasingha, Nuwandi M.,Chekmenev, Eduard Y.,Chukanov, Nikita V.,Gelovani, Juri G.,Joalland, Baptiste,Koptyug, Igor V.,Kovtunov, Kirill V.,Nantogma, Shiraz,Salnikov, Oleg G.,Younes, Hassan R.

, p. 2774 - 2781 (2021/01/18)

Many MRI contrast agents formed with the parahydrogen-induced polarization (PHIP) technique exhibit biocompatible profiles. In the context of respiratory imaging with inhalable molecular contrast agents, the development of nonflammable contrast agents would nonetheless be highly beneficial for the biomedical translation of this sensitive, high-throughput and affordable hyperpolarization technique. To this end, we assess the hydrogenation kinetics, the polarization levels and the lifetimes of PHIP hyperpolarized products (acids, ethers and esters) at various degrees of fluorine substitution. The results highlight important trends as a function of molecular structure that are instrumental for the design of new, safe contrast agents for in vivo imaging applications of the PHIP technique, with an emphasis on the highly volatile group of ethers used as inhalable anesthetics.