637-92-3

Usage

Uses

Used in Gasoline Additive Industry:
TERT-BUTYL ETHYL ETHER is used as an oxygenate to improve automobile exhaust quality by reducing ozone and carbon monoxide emissions. It serves as a potential replacement for methyl tertiary butyl ether (MTBE) due to its similar utility.
Used in Fuel Additive Industry:
TERT-BUTYL ETHYL ETHER is used as a fuel additive to enhance the octane rating of petrol. Its production and use have been halted in the United States due to litigation and liability concerns, but it continues to be widely used in Europe and other parts of the world, including the Middle East, South America, Mexico, and Asia.
Used in Extractant Industry:
TERT-BUTYL ETHYL ETHER is used as an extractant in human urine, utilizing single-walled carbon nanotubes as an adsorbent. This application plays an important role in various analytical and diagnostic processes.

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.]

InChI:InChI=1/C6H14O/c1-5-7-6(2,3)4/h5H2,1-4H3

Upstream product

• 64-17-5 ethanol 
• 507-20-0 tertiary butyl chloride 
• 507-19-7 t-butyl bromide 
• 75-03-6 ethyl iodide 
• 865-48-5 sodium t-butanolate 
• 121-44-8 triethylamine 
• 115-11-7 isobutene 
• 75-65-0 tert-butyl alcohol 
• 109-94-4 formic acid ethyl ester 
• 425-24-1 tert-butyl heptafluorobutyrate 
• 865-47-4 potassium tert-butylate 
• 558-17-8 tert-Butyl iodide 
• 74-96-4 ethyl bromide 
• 507-40-4 tert-butylhypochlorite 

Downstream Products

• 540-88-5 acetic acid tert-butyl ester 
• 141-78-6 ethyl acetate 
• 93-89-0 benzoic acid ethyl ester 
• 50-00-0 formaldehyd 
• 598-58-3 methyl nitrate 
• 762-75-4 tert-butyl formate 
• 64-17-5 ethanol 
• 115-11-7 isobutene 
• 74-84-0 ethane 
• 75-28-5 Isobutane 
• 74-85-1 ethene 
• 75-07-0 acetaldehyde 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 255041-56-6 2-(2-tert-butoxyethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Thermodynamic study of liquid phase synthesis of ethyl tert-butyl ether using tert-butyl alcohol and ethanol

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

Equilibrium constant for ethyl tert-butyl ether vapor-phase synthesis

Equilibrium constants for the vapor-phase synthesis of ethyl tert-butyl ether (ETBE) were determined experimentally at temperatures from 319 to 373 K. Equilibrium was established in the addition of ethanol to isobutene for obtaining ETBE over Amberlyst-15 in a flow reactor maintained at atmospheric pressure. The equilibrium constants obtained in the present work were compared with estimates from thermochemical data. The values of ?H°, ?G°, ?S° at 298 K were obtained from the variation of equilibrium constant with temperature: ?H° = -14.87 ± 0.5 cal·mol-1, ?GΔR = -2.8 ± 0.8 kcal·mol-1, and ?S° =-40.5 ± 1.3 cal·mol-1·K-1. By use of published thermochemical data together with the experimental data, the enthalpy of formation, ?Hf°298, free energy of formation ?Gf°298, and absolute entropy, S°298, of ETBE were calculated to be -75.03 POM 0.5 kcal·mol-1, -29.14 ± 0.5 kcal·mol-1, and 97.1 ± 1 cal·mol-1·K-1, respectively.

Comparative vapor phase synthesis of ETBE from ethanol and isobutene over different acid zeolites

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.

Preparation of hybrid organo-inorganic catalysts based on msm-41 mesoporous molecular sieves and their properties in synthesis of ethyl tert-butyl ether

A series of sulfoorganosilica (vinyl-containing) catalysts based on MSM-41 mesoporous molecular sieves were prepared by template synthesis. The structure and properties of these catalysts and their catalytic characteristics in synthesis of ethyl tert-buty

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

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.

Insight into the active site nature of zeolite H-BEA for liquid phase etherification of isobutylene with ethanol

The nature of active acid sites of zeolite H-BEA with different Si/Al ratios (15-407) in liquid phase etherification of isobutylene with ethanol in a continuous flow reactor in the temperature range 80-180 °C has been explored. We describe and discuss data concerning the strength and concentration of acid sites of H-BEA obtained by techniques of stepwise (quasi-equilibrium) thermal desorption of ammonia, X-ray diffraction, low-Temperature adsorption of nitrogen, FTIR spectroscopy of adsorbed pyridine and solid-state 27Al MAS NMR. The average values of the adsorption energy of NH3 on H-BEA were experimentally determined as 63.7; 91.3 and 121.9 mmol g-1 (weak, medium, and strong, respectively). In agreement with this, a correlation between the rate of ethyl-Tert-butyl ether synthesis and the concentration of weak acid sites (ENH3 = 61.6-68.9 kJ mol-1) has been observed. It was concluded that the active sites of H-BEA for this reaction are Br?nsted hydroxyls representing internal silanol groups associated with octahedrally coordinated aluminum in the second coordination sphere.

METHOD FOR PRODUCING ASYMMETRIC ALKYL ETHER HAVING TERTIARY ALKYL GROUP

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

1,2,3-Triazolylidene ruthenium(ii)-cyclometalated complexes and olefin selective hydrogenation catalysis

Silver(i) 1,2,3-triazol-5-ylidenes [(RCH2C2N2(NMe)Ph)2Ag][AgCl2] (R = Ph 3a, C6H2iPr33b, C6H2Me33c) and [(PhCH2C2N2(NMe)R)2Ag][AgCl2] (R = C6H4Me 3d, C6H4CF33e) were synthesized and subsequently treated with RuHCl(PPh3)3 and RuHCl(H2)(PCy3)2. The reaction of 3a with RuHCl(PPh3)3 gave RuHCl(PPh3)2(PhCH2C2N2(NMe)Ph) (4a1) as the minor product and the cyclometalated complex RuCl(PPh3)2(PhCH2C2N2(NMe)C6H4) (4a2) as the major product. However, similar reaction with 3b selectively formed the cyclometalated complex RuCl(PPh3)2((C6H2iPr3)CH2C2N2(NMe)C6H4) (4b2). Similarly the silver(i) triazolylidenes 3a and 3b were reacted with RuHCl(H2)(PCy3)2; gave RuHCl(PCy3)2(PhCH2C2N2(NMe)Ph) (5a1), RuCl(PCy3)2(PhCH2C2N2(NMe)C6H4) (5a2) and RuCl(PCy3)2((C6H2iPr3)CH2C2N2(NMe)C6H4) (5b2), respectively. Species 3c, 3d and 3e resulted in the cyclometalated complexes (5c2, 5d2 and 5e2) as the major products as well as the ruthenium-hydride complexes (5c1, 5d1 and 5e1) as the minor products. The cyclometalated species are derived from the ruthenium-hydride complexes via C(sp2)-H activation. These Ru-complexes were shown to act as hydrogenation catalyst precursors for olefinic substrates including those containing a variety of functional groups. This journal is

Method for coproducing isobutene and ETBE from tert-Butanol mixture

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.

Half sandwich ruthenium(ii) hydrides: Hydrogenation of terminal, internal, cyclic and functionalized olefins

Bis(1,2,3-triazolylidene) silver(i) complex 1a was reacted with [RuCl2(p-cymene)]2 to give the ruthenium complex [PhCH2N2(NMe)C2(C6H4CF3)]RuCl2(p-cymene) (2a) as major product in addition to the minor C(sp2)-H activated product [PhCH2N2(NMe)C2(C6H3CF3)]RuCl(p-cymene) (2a′). Similar ruthenium complexes 2b, 2c, 2d and 2e with general formula RuCl2(p-cymene)(NHC) (NHC = MesCH2N2(NMe)C2Ph 2b, PhCH2N2(NMe)C2Ph 2c, TripCH2N2(NMe)C2Ph 2d, IMes 2e) were also synthesized. Subsequent reaction of Me3SiOSO2CF3 with 2a and 2b resulted in cationic ruthenium species [(PhCH2N2(NMe)C2(C6H4CF3))RuCl(p-cymene)][OSO2CF3] (3a) and [(MesCH2N2(NMe)C2Ph)RuCl(p-cymene)][OSO2CF3] (3b), respectively. Complexes 3a and 3b dissolved in CD3CN to give [(PhCH2N2(NMe)C2(C6H4CF3))RuCl(CD3CN)(p-cymene)][OSO2CF3] (4a) and [(MesCH2N2(NMe)C2Ph)RuCl(CD3CN)(p-cymene)][OSO2CF3] (4b), respectively. Cationic ruthenium species 4a and 4b failed to show catalytic activity towards hydrogenation of olefins. Ruthenium(ii) complexes 2b-e with the general formula RuCl2(p-cymene)(NHC) were reacted with Et3SiH to generate a series of ruthenium(ii) hydrides 5b-e. These compounds 5b-e are effective catalysts for the hydrogenation of terminal, internal and cyclic and functionalized olefins.