26356-10-5

Usage

Uses

Used in Fuel Industry:
MTBE is used as a fuel additive for gasoline to increase the oxygen content, which improves the combustion efficiency and reduces emissions. This application helps in enhancing the performance of engines and reducing air pollution caused by incomplete combustion.
Used in Industrial Processes:
MTBE serves as a solvent in various industrial processes, such as in the manufacturing of paints, coatings, and adhesives. Its solvent properties enable the dissolution of various substances, facilitating their application in different industries.
Used in Organic Synthesis:
MTBE is utilized as a reagent in organic synthesis, where it aids in the formation of new chemical compounds. Its reactivity and stability make it a valuable component in the synthesis of various organic compounds.
However, due to the potential environmental and health risks associated with MTBE, its use has been phased out or banned in many countries, leading to the exploration of alternative fuel additives and solvents.

Upstream product

• 67-56-1 methanol 
• 563-79-1 2,3-Dimethyl-2-butene 
• 26356-06-9 2-Bromo-3,3-dimethylbutane 
• 2510-55-6 9-cyanophenanthrene 
• 594-60-5 2,3-dimethylbutan-2-ol 
• 74-88-4 methyl iodide 
• 75-83-2 2,2-Dimethylbutane 
• 563-78-0 2,3-Dimethyl-1-butene 
• 201230-82-2 carbon monoxide 
• 64-18-6 formic acid 

Downstream Products

• 563-79-1 2,3-Dimethyl-2-butene 
• 563-78-0 2,3-Dimethyl-1-butene 

Relevant academic research and scientific papers

Hydride Ion Transfer Reactions in the Gas Phase. Pressure Dependence of Reaction Efficiency as a Criterion for the Recognition of Anchimeric Assistance

The efficiency (kobs/kcoll) of the gas phase hydride ion transfer from 2,2-dimethylbutane to tert-butyl cation displays a pronounced positive pressure dependence, which suggests significant anchimeric assistance of the methyl groups of 2,2-dimethylbutane adjacent to the departing CH2 hydride in the transition state.

METHOXYCARBONYLATION WITH FORMIC ACID AS CO SOURCE

Process for methoxycarbonylation with formic acid as the CO source.

Development of efficient palladium catalysts for alkoxycarbonylation of alkenes

Herein, we report a general and efficient Pd-catalysed alkoxycarbonylation of sterically hindered and demanding olefins including a variety of tri-, tetra-substituted and 1,1-disubstituted alkenes. In the presence of 1,3-bis(tert-butyl(pyridin-2-yl)phosphanyl)propane L3 or 1,4-bis(tert-butyl(pyridin-2-yl)phosphanyl)butane L4 the desired esters are obtained in good yields and selectivities. Similar transformation is obtained using tertiary ether as showcased in the carbonylation of MTBE to the corresponding linear ester in high yield and selectivity.

Palladium-catalyzed selective generation of CO from formic acid for carbonylation of alkenes

A general and selective palladium-catalyzed alkoxycarbonylation of all kinds of alkenes with formic acid (HCOOH, FA) is described. Terminal, di-, tri-, and tetra-substituted including functionalized olefins are converted into linear esters with high yields and regioselectivity. Key-to-success is the use of specific palladium catalysts containing ligands with built-in base, e.g., L5. Comparison experiments demonstrate that the active catalyst system not only facilitates isomerization and carbonylation of alkenes but also promotes the selective decomposition of HCOOH to CO under mild conditions.

Benzene-based diphosphine ligands for alkoxycarbonylation

The invention relates to benzene-based diphosphine ligands for alkoxycarbonylation. Specifically, the invention relates to compounds of formula (I), where m and n are each independently 0 or 1; R1, R2, R3, R4 are each independently selected from -(C1-C12)-alkyl, -(C3-C12)-cycloalkyl, -(C3-C12)-heterocycloalkyl, -(C6-C20)-aryl, -(C3-C20)-heteroaryl; at least one of the R1, R2, R3, R4 radicals is a -(C3-C20)-heteroaryl radical; and to the use thereof as ligands in alkoxycarbonylation.

Isomerizing Methoxycarbonylation of Alkenes to Esters Using a Bis(phosphorinone)xylene Palladium Catalyst

The synthesis and characterization of bulky diphosphine 1,2-bis(4-phosphorinone)xylene, BPX, and its palladium complexes [(BPX)PdCl2] and [(BPX)Pd(O2CCF3)2] are described. BPX was evaluated as a ligand in Pd-catalyzed isomerizing methoxycarbonylation. A broad range of alkenes, including terminal, internal, branched, and functionalized alkenes, can be converted to esters with activities and selectivities matching or surpassing the performance of the state-of-the-art palladium bis(di(tert-butyl)phosphino-o-xylene (Pd-DTBPX) catalyst. A molecular structure of the precatalyst [(BPX)Pd(O2CCF3)2] was obtained showing a square planar geometry and a bite angle of 100.11(3)°. Rhodium carbonyl complexes [(BPX)Rh(CO)Cl] and [(DTBPX)Rh(CO)Cl] were synthesized to compare the relative electronic parameters, revealing a ν(C≡O) of 1956.8 and 1948.3 cm-1, respectively, suggesting a reduced ability of BPX to donate electron density to the metal relative to DTBPX. Competitive protonation experiments between BPX and DTBPX in the presence of CH3SO3H exclusively produce [DTBPX(H)2]2+, providing additional evidence that BPX is a much weaker base than DTBPX. This could be due to either the effect of the electron-withdrawing ketone group in the phosphorinone ring or the compression of the C-P-C bond angle induced by the ring structure. The 31P NMR (CDCl3) chemical shift of BPX is 5.6 ppm, upfield of DTBPX at 27.6 ppm. This anomalous result is attributed to a strong gamma substituent effect of C=O in the BPX ligand. The improved activity of Pd-BPX, relative to Pd-DTBPX, could be attributed to a more electrophilic PdII center, which could accelerate the rate-determining methanolysis step.

Silica-supported sulfated zirconia: A new effective acid solid for etherification

Silica-supported sulfated zirconia exhibits a comparable and even higher ether production than a reference acid resin (Amberlyst 15) giving an ether yield of 30% at 50% conversion.

Synthesis of 2,3-Dimethyl-2-methoxybutane and 2-Methyl-2-methoxypentane from Methanol and Propylene Dimers Produced by the Dimerization of Propylene on Complex Nickel Catalysts

A study has been made of the addition of methanol under the action of acid catalysts to propylene dimers 2,3-dimethylbut-1-ene, 2,3-dimethylbut-2-ene, 2-methyl-1-pentene and 2-methyl-2-pentene with the formation of 2,3-dimethyl-2-methoxybutane and 2-methyl-2-methoxypentane respectively.

Solvomercuration-Demercuration. 12. The Solvomercuration-Demercuration of Olefins in Alcohol Solvents with Mercuric Trifluoroacetate--An Ether Synthesis of Wide Generality

Studies on the solvomercuration-demercuration (SM-DM) of olefins in methyl, ethyl, isopropyl, and tert-butyl alcohols with mercuric trifluoroacetate have been extended. 1-Dodecene undergoes the SM-DM sequence with typical results for a monosubstituted olefin.Cyclopentene similarly exhibited behavior characteristic of a 1,2-disubstituted olefin in methanol, ethanol, and 2-propanol, giving high yields, >90percent of the corresponding ethers.However, in tert-butyl alcohol, the yields of ether were lower than normal and decreased somewhat with time. 2-Methyl-1-butene gives >90percent yields of the Markovnikov methyl ether.On the other hand, the yields of ethyl, isopropyl, and tert-butyl ethers are lower and decrease with time.Major improvements in yields, however, are possible by lowering the reaction temperature from room temperature to 0 deg C.Cyclooctene, surprisingly, behaves more like a tri-, tetra-, or isosubstituted olefin than a 1,2-disubstituted olefin.The yields of cyclooctyl methyl ether are >90percent and do not decrease with time.However, yields of the ethyl, isopropyl, and tert-butyl ethers are lower and drop with time.Again, lowering the reaction temperature from room temperature to 0 deg C markedly improves the yields of the cyclooctyl ethers.These results, coupled with those of a previous study, clearly reveal the exceptional superiority of mercuric trifluoroacetate for the SM-DM of olefins in alcohol solvents.

Solvomercuration-Demercuration. 11. Alkoxymercuration-Demercuration of Representative Alkenes in Alcohol Solvents with the Mercuric Salts Acetate, Trifluoroacetate, Nitrate, and Methanesulfonate

The alkoxymercuration-demercuration of seven representative olefins with the mercuric salts acetate, trifluoroacetate, nitrate, and methanesulfonate, in methyl, ethyl, isopropyl, and tert-butyl alcohols was examined.Mercuric acetate was effective only in methanol and ethanol.On the other hand, mercuric trifluoroacetate was effective in all four solvents, giving in most cases high yields of the corresponding ethers.Both mercuric nitrate and mercuric methanesulfonate were effective in methanol, ethanol, and 2-propanol.However, in several cases poor selectivity for the ether was observed, as evidenced by the formation of significant amounts of side products.Both electronic and steric effects are important factors in the reaction.Moreover, the structure of the olefin has a pronounced effect, both on the types of oxymercurials formed and on their stability to the reaction conditions.