tert-Butyl ethyl ether

Base Information

• Chemical Name: tert-Butyl ethyl ether
• CAS No.: 637-92-3
• Molecular Formula: C6H14 O
• Molecular Weight: 102.177
• Hs Code.: 2909199090
• European Community (EC) Number: 211-309-7
• ICSC Number: 1706
• NSC Number: 1069
• UN Number: 1179
• UNII: 3R9B16WR19
• DSSTox Substance ID: DTXSID0025604
• Nikkaji Number: J45.669A
• Wikipedia: Ethyl_tert-butyl_ether
• Wikidata: Q424480
• ChEMBL ID: CHEMBL1409831
• Mol file: 637-92-3.mol

Synonyms:2-ethoxy-2-methylpropane;ETBE;ethyl tert-butyl ether;ethyl tertiary-butyl ether;tert-butyl ethyl ether

Chemical Property of tert-Butyl ethyl ether

Chemical Property:

• Appearance/Colour: clear, colorless liquid.
• Vapor Pressure: 155 mm Hg ( 25 °C)
• Melting Point: ?97 °C(lit.)
• Refractive Index: n20/D 1.375(lit.)
• Boiling Point: 70 °C at 760 mmHg
• Flash Point: -19 C (closed cup)
• PSA: 9.23000
• Density: 0.742 g/mL at 25 °C(lit.)
• LogP: 1.82140
• Storage Temp.: Flammables area
• Solubility.: water: soluble1.2 g/100g at 20°C(lit.)
• Water Solubility.: Miscible with alcohol, ethyl ether. Slightly miscible with water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 102.104465066
• Heavy Atom Count: 7
• Complexity: 42.6
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99.9% ^*data from raw suppliers

tert-Butyl Ethyl Ether >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): FXi
• Hazard Codes: F,Xi
• Statements: 11-36/38-67
• Safety Statements: 16-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ethers (
• Canonical SMILES: CCOC(C)(C)C
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. If swallowed the substance easily enters the airways and could result in aspiration pneumonitis. The substance may cause effects on the central nervous system. Exposure could cause lowering of consciousness.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis.
• Description: In the 1990s, the production of other fuel oxygenates began, with the appearance of ethyl tertiary-butyl ether, CAS RN 637- 92-3 (ETBE), first produced in France in 1992, and tertiary-amyl methyl ether, CAS RN 994-05-8 (TAME). To their number others have been added, such as diisopropyl ether, CAS RN 108-20-3 (DIPE) and, most recently, tertiary-amyl ethyl ether, CAS RN 919-94-8 (TAEE), which is being produced in Germany; however, the use of these oxygenates is currently small scale. Alcohols, such as ethanol, CAS RN 64-17-5 (EtOH) and methanol, may also be used as fuel oxygenates, but methanol is not used as such, although it is used in China as a liquid fuel for passenger cars and for synthesis of dimethyl ether as an alternative to diesel fuel for trucks and buses. Ethers have the advantage over alcohols in currently designed engines because alcohols in petrol tend to make the blend very volatile and water soluble, possibly creating problems in the fueldistribution system and vehicle engine. Perhaps the larger-scale use of ethanol in fuel oxygenation is in the production of ETBE or coblending with ETBE.
• Uses: Gasoline additive. tert-Butyl ethyl ether is synthesized from ethanol and isobutene and is used primarily as an oxygenate that is added to gasoline to improve the automobile exhaust quality by reducing the ozone and carbon monoxide emissions (HSDB, 2012). tert-Butyl ethyl ether has similar utility compared to another widely used oxygenate, methyl tertiary butyl ether (MTBE), and thus is a potential replacement for MTBE.Usage of ETBE as a fuel additive has halted in the United States, falling from 2 to 4 million barrels per month in 2005 to 0 barrels in 2006 (DOE, 2007). tert-Butyl ethyl ether continues to be used widely in Europe (EFOA, 2010). Since ETBE is used almost exclusively in fuels, contamination of groundwater as a result of spillage or leakage of the underground storage tanks is a major source of environmental release. In 2006, because of litigation and liability fears, the blending (but not the production) of MTBE into petrol in the United States was discontinued, whereas the European Union (EU) has continued its use of ethers in blending. Other global producers and consumers of fuel ether oxygenates are the Middle East, South America (excluding Brazil), Mexico, and a large portion of Asia. The current global production capacity is estimated to be approximately 18 Mton year1. The expected demand for MTBE t ETBE in Asia is 11.9 Mton. In 2010, China was the world’s largest producer of MTBE (6.8 Mton year1), yet was also importing MTBE at 740 kton in the same year. In Japan, Bio-ETBE is the biofuel of choice for petrol. It is preferred over alcohols in Japan on the basis of emission benefits, vehicle performance, and existing regulations. tert-Butyl ethyl ether is used as an oxygenate gasoline additive oxygenate during its production from crude oil. It is used as an extractant in human urine by using single-walled carbon nanotubes as an adsorbent. It plays an important role as a fuel component in petrol to enhance its octane rating.

Technology Process of tert-Butyl ethyl ether

There total 43 articles about tert-Butyl ethyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

potassium tert-butylate (865-47-4) + N-carbomethoxy-N'-methyl-2-ethoxyimidazolinium fluoroborate → 1-methyl-2-imidazolidone (694-32-6) + Ethyl tert-butyl ether (637-92-3) + N-carbomethoxy-N'-methylimidazolidone (61076-69-5)

Guidance literature:

In dichloromethane; for 18h; Product distribution; Ambient temperature;

DOI:10.1021/ja00531a041

Reference yield: 83.0%

ethyl bromide (74-96-4) + tert-butyl alcohol (75-65-0) → Ethyl tert-butyl ether (637-92-3)

Guidance literature:

With sodium hydroxide; cetyltrimethylammonim bromide; In water; at 70 ℃;

DOI:10.1016/S0040-4020(01)90106-1

Reference yield: 65.0%

tert-butyl vinyl ether (926-02-3) + hydrogen (1333-74-0) → Ethyl tert-butyl ether (637-92-3)

Guidance literature:

With C₆₁H₉₈ClN₃P₂Ru; In dichloromethane-d2; at 50 ℃; for 24h; under 3040.2 Torr; Reagent/catalyst; Time;

DOI:10.1039/c4dt03156c

upstream raw materials:

ethanol

tertiary butyl chloride

t-butyl bromide

ethyl iodide

Downstream raw materials:

acetic acid tert-butyl ester

ethyl acetate

formaldehyd

methyl nitrate

Refernces

• 1、 Iborra,Izquierdo,Tejero,Cunill. "Equilibrium constant for ethyl tert-butyl ether vapor-phase synthesis". . p. 1 - 5. Retrieved 1989.
• 2、 Vlasenko,Kochkin, Yu. N.,Kovalenko. "Preparation of hybrid organo-inorganic catalysts based on msm-41 mesoporous molecular sieves and their properties in synthesis of ethyl tert-butyl ether". . p. 2166 - 2173. Retrieved 2009.
• 3、 Vlasenko, Nina V.,Kochkin, Yuri N.,Telbiz, German M.,Shvets, Oleksiy V.,Strizhak, Peter E.. "Insight into the active site nature of zeolite H-BEA for liquid phase etherification of isobutylene with ethanol". . p. 35957 - 35968. Retrieved 2019/11/20.
• 4、 -. "Method for coproducing isobutene and ETBE from tert-Butanol mixture". Page/Page column 6-12. . Retrieved 2015/11/09.