637-92-3 Usage
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.
Chemical Properties
tert-Butyl ethyl ether is a colourless to light yellow liquid at a temperature range of -94 to 72.6 °C. It is soluble in ethanol, ethyl ether, and water. tert-Butyl ethyl ether has a strong, highly objectionable odor and taste at relatively low concentrations. This chemical is highly flammable and reacts with strong oxidizing agents. tert-Butyl ethyl ether is stable when stored at room temperature in tightly closed containers.
Uses
Different sources of media describe the Uses of 637-92-3 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.
Synthesis Reference(s)
Tetrahedron Letters, 29, p. 2445, 1988 DOI: 10.1016/S0040-4039(00)87903-4
Air & Water Reactions
Highly flammable. TERT-BUTYL ETHYL ETHER may react with air to form dangerous peroxides. . Insoluble in water.
Reactivity Profile
TERT-BUTYL ETHYL ETHER can act as a base to form salts with strong acids and addition complexes with Lewis acids. May react violently with strong oxidizing agents. Relatively inert in other reactions, which typically involve the breaking of the carbon-oxygen bond.
Health Hazard
Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Fire Hazard
TERT-BUTYL ETHYL ETHER is flammable.
Flammability and Explosibility
Highlyflammable
Environmental Fate
Due to the usage of Ethyl tertiary butyl ether (ETBE ) as a fuel additive, ETBE may be released into air, soil, and water. Ethyl tertiary butyl ether will exist as a vapor at 25 °C due to its vapor pressure of 124mmHg and is estimated to have a half-life of 2 days. Upon release into the soil, ETBE is anticipated to have a high mobility based on the high soil organic carbon–water partitioning coefficient of 9–160. Once in the water, ETBE is not predicted to adsorb onto suspended particles and is likely to resist biodegradation (Deeb et al., 2001). Based on the Henry’s law constant, ETBE is likely to be volatized from the surface of the water (HSDB, 2012). A volatilization halflife of 3 h to 4 days is anticipated from water solutions. A bioconcentration factor (BCF) of 9 was estimated for ETBE to accumulate in fish, suggesting a relatively low propensity for aquatic bioaccumulation (HSDB, 2012).
Purification Methods
Dry the ether with CaSO4, pass it through an alumina column, and fractionally distil it. [Beilstein 1 IV 1618.]
Check Digit Verification of cas no
The CAS Registry Mumber 637-92-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 7 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 637-92:
(5*6)+(4*3)+(3*7)+(2*9)+(1*2)=83
83 % 10 = 3
So 637-92-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H14O/c1-5-7-6(2,3)4/h5H2,1-4H3
637-92-3Relevant articles and documents
Thermodynamic study of liquid phase synthesis of ethyl tert-butyl ether using tert-butyl alcohol and ethanol
Ozbay, Nalan,Oktar, Nuray
, p. 3208 - 3214 (2009)
In this study, a detailed thermodynamic analysis of the ethyl tert-butyl ether (ETBE) synthesis reaction between tert-butyl alcohol (TBA) and ethanol is performed to determine a liquid phase equilibrium constant expression. The result is of practical sign
Comparative vapor phase synthesis of ETBE from ethanol and isobutene over different acid zeolites
Poncelet,Collignon
, p. 68 - 77 (2001)
Vapor phase synthesis of ETBE from ethanol and isobutene was studied over US-Y, Beta, and ZSM-5 zeolites with different Si/Al ratios, using Amberlyst-15 as a reference catalyst. The sequence of activity was Beta zeolite > US-Y> Mordenite > Omega ≥ ZSM-5. At maximum isobutene to ETBE conversion, the Beta zeolites yielded more ETBE than the commercial samples and acid resin. With external surface area of > 200 sq m/g, Beta zeolites were the most active among the zeolites. Amberlyst-15 and Beta zeolites were 100% selective below 55°C. Extra-framework Al species showed negative effect on the reaction, and their removal by a mild acid leaching was beneficial.
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.
METHOD FOR PRODUCING ASYMMETRIC ALKYL ETHER HAVING TERTIARY ALKYL GROUP
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Paragraph 0019, (2017/01/31)
PROBLEM TO BE SOLVED: To provide a method capable of obtaining an asymmetric alkyl ether having a tertiary alkyl group easily and industrially. SOLUTION: (1) There is provided a method for producing an asymmetric alkyl ether having a tertiary alkyl group by subjecting a tertiary alcohol and a primary alcohol or a secondary alcohol to a dehydration reaction using activated clay as a catalyst. (2) There is provided the method for producing an asymmetric alkyl ether having a tertiary alkyl group according to (1), where the tertiary alcohol is any one selected from the group consisting of tert-butanol, tert-amylalcohol and 1-adamantyl alcohol. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
Method for coproducing isobutene and ETBE from tert-Butanol mixture
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Page/Page column 6-12, (2015/11/09)
This invention describes a method for co-producing isobutene and ethyl tert-butyl ether from tert-butanol mixture in a catalytic distillation column, wherein catalyzing the tert-butanol mixture with the ethanol undergoes dehydration and etherification. The tert-butanol mixture contains absolute ethanol or aqueous ethanol as the antifreeze agent. The isobutene and the ethyl tert-butyl ether withdrawn from the column top are further separated, thus high purity isobutene and ethyl tert-butyl ether for fuel-additive are obtained.