17351-61-0

Basic information

• Product Name: TETRAETHYLAMMONIUM BICARBONATE
• Synonyms: Tetraethylammonium bicarbonate purum, >=95.0% (T);Tetraethylammonium bicarbonate >=95.0% (T)
• CAS NO: 17351-61-0
• Molecular Formula: CHO₃*C₈H₂₀N
• Molecular Weight: 0
• Mol File: 17351-61-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: TETRAETHYLAMMONIUM BICARBONATE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAETHYLAMMONIUM BICARBONATE(17351-61-0)
• EPA Substance Registry System: TETRAETHYLAMMONIUM BICARBONATE(17351-61-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 17351-61-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Tetraethylammonium bicarbonate is used as a reagent for the synthesis of carbamate esters from amines. Its ability to facilitate this reaction makes it a valuable component in the production of various chemical compounds.
Used in Catalyst Production:
In the field of catalysis, tetraethylammonium bicarbonate serves as a precipitant for synthesizing Cu/ZnO catalysts via the coprecipitation method. This application highlights its importance in the development of efficient and effective catalysts for industrial processes.
Used in Radiochemistry:
Tetraethylammonium bicarbonate is used as an alternative to the traditional phase-transfer system in [18F]radiofluorinations. Its role in preventing microreactor blockages makes it a preferred choice for enhancing the efficiency and safety of radiochemical reactions.
Used in Pharmaceutical Synthesis:
In the synthesis of oxazolidine-2,4-diones, tetraethylammonium bicarbonate is used as a promoter for carboxylation of secondary carboxamides bearing a leaving group at the α-position. This application demonstrates its utility in the development of pharmaceutical compounds with potential therapeutic applications.

Upstream product

• 124-38-9 carbon dioxide 
• 56-34-8 tetraethylammonium chloride 
• 665-46-3 tetraethylammonium fluoride 
• 429-41-4 tetrabutyl ammonium fluoride 
• 144-55-8 sodium hydrogencarbonate 
• 77-98-5 tetraethylammonium hydroxide 
• 105-58-8 Diethyl carbonate 

Downstream Products

• 17153-05-8 N-benzyl-oxazolidine-2,4-dione 
• 3759-90-8 3-Phenyl-1,3-oxazolidin-2,4-dion 
• 5466-93-3 diethyl 1,4-phenylenediamine-N,N'-dicarboxylate 
• 99305-42-7 dibutyl (methylene-bis(cyclohexane-4,1,diyl))dicarbamate 
• 526-35-2 3-allyl-5-methyloxazolidine-2,4-dione 
• 58006-99-8 3,5-dimethyloxazolidine-2,4-dione 
• 2621-78-5 ethyl N-benzylcarbamate 
• 5325-60-0 ethyl N-allylcarbamate 
• 59325-17-6 ethyl benzyl(methyl)carbamate 
• 101-99-5 N-carboethoxyaniline 
• 185910-72-9 ethyl N-(3-phenylpropyl)carbamate 
• 7451-55-0 ethyl 4-methoxyphenylcarbamate 
• 3580-74-3 cyclohexylcarbamic acid isopropyl ester 
• 1541-19-1 ethyl N-cyclohexylcarbamate 

Relevant articles and documents

Sustainable Carboxylation of Diamines with Hydrogen Carbonate

A protocol for the carboxylation of diamines employing quaternary ammonium hydrogen carbonates as C1 source is presented. The approach is used to obtain industrially relevant bis-O-alkyl carbamates with diverse structural features in very high yield, even on gram scale. The quaternary ammonium salts, formally acting as "transporters" of the carboxylating agent, can be recovered after the reaction, and recycled with high efficiency. Regeneration of the hydrogen carbonates on ion-exchange resin grants excellent atom economy in the process.

Use of tetraethylammonium bicarbonate as a precipitation agent on the preparation of coprecipitated Cu/ZnO catalysts

Cu/ZnO catalysts were prepared by coprecipitation using tetraethylammonium bicarbonate (TEA+HCO3?), and their properties and methanol synthesis activities were compared to those of the catalysts prepared using Na+HCO3? usually employed for commercial Cu/ZnO/(Al2O3) catalysts. When washed fully, TEA+- and Na+-based precursors showed typical zincian malachite (zM) without any other structures, and both catalysts obtained after calcination and H2 reduction exhibited the similar specific copper surface area and, in turn, the similar methanol productivity. Since this result explains that TEA+ does not affect zM structure if Cu,Zn precipitate is fully washed, no washed and less washed TEA+- and Na+-based precursors were prepared. It was interesting that all TEA+-based catalysts exhibited the similar methanol productivity irrespective of the washing efficiency whereas Na+-based catalyst containing more residual Na+ showed the smaller copper surface area and lower methanol productivity (i.e., linear correlation between the two parameters). This resulted from the inhibiting effect of Na+ on the degree of Cu2+ substitution by Zn2+ and the formation of high-temperature carbonate, consequently leading to a lower catalytic activity. These negative effects of Na+ were absent or lessened when TEA+HCO3? was used as a precipitation agent, which is effective in preparing an active methanol synthesis catalyst.

Chemical fixation of atmospheric co2 by copper(Ii) complexes of a tridentate n-donor ligand

Using an unsymmetrical tridentate N-donor ligand (2-pyridylethyl){2-(1-methylimidazolyl)methyl}methylamine (L3), synthesis, spectral (IR, UV/Vis, ESI-MS, and EPR), magnetic (as solid/in solution) and redox properties of a monomeric green [(L3)CuIICl2]·MeOH (1), a dimeric light-blue [{(L3)CuII(μ-OH)}2](ClO4)2 (2), a dimeric blue [{(L3)CuII(μ-OMe)}2](ClO4)2 (3), and a trimeric ink-blue [{(L3)CuII(OClO3)}3(μ3-OCO2)](ClO4) (4) complexes were achieved. Complexes 1, 3, and 4 were structurally characterized. Isolation of 4 was achieved by the reaction between {(L3)2CuII2(μ-OH)2}2+ species (formed from the reaction between (i) solution-generated yellow [(L3)CuI(MeCN)]1+ species and O2, followed by reaction with moisture and (ii) 1 and NaOH in water and CO2 in open air, under ambient conditions. Reactivity of 2 with MeOH results in the formation of 3. The observed CO2 fixation by reactive complex 2 to afford 4 was rationalized, through designed experiments including kinetic measurements. Thermodynamic parameters of HCO3–/CO2 binding were also derived. Temperature-dependent magnetic measurements of 4 indicated a ferromagnetic exchange-coupling (J = 48 cm–1). Notably, 4 exhibits largest ferromagnetic coupling (J = 48 cm–1) amongst all complexes reported so far with similar mode of carbonate-bridging.

Capture and displacement-based release of the bicarbonate anion by calix[4]pyrroles with small rigid straps

Two-phenoxy walled calix[4]pyrroles 1 and 2 strapped with small rigid linkers containing pyridine and benzene, respectively, have been synthesized. 1H NMR spectroscopic analyses carried out in CDCl3 revealed that both of receptors 1 and 2 recognize only F- and HCO3- among various test anions with high preference for HCO3- (as the tetraethylammonium, TEA+ salt) relative to F- (as the TBA+ salt). The bound HCO3- anion was completely released out of the receptors upon the addition of F- (as the tetrabutylammonium, TBA+ salt) as a result of significantly enhanced affinities and selectivities of the receptors for F- once converted to the TEAHCO3 complexes. Consequently, relatively stable TEAF complexes of receptors 1 and 2 were formed via anion metathesis occurring within the receptor cavities. By contrast, the direct addition of TEAF to receptors 1 and 2 produces different complexation products initially, although eventually the same TEAF complexes are produced as via sequential TEAHCO3 and TBAF addition. These findings are rationalized in terms of the formation of different ion pair complexes involving interactions both inside and outside of the core receptor framework. This journal is

SUSTAINABLE SYNTHESIS OF CARBAMATE COMPOUNDS

A method for the production of carbamate compounds comprises the steps of: A) reacting an organic primary amine with an organic halogen compound in the presence of a quaternary organic ammonium carbonate and/or bicarbonate, thereby obtaining a reaction mixture comprising a carbamate compound and a quaternary organic ammonium salt; B) separating the quaternary organic ammonium salt from the reaction mixture obtained after step A); C) contacting the quaternary organic ammonium salt obtained after step B) with a carbonate and/or bicarbonate anion-exchange resin, thereby obtaining a quaternary organic ammonium carbonate and/or bicarbonate; D) repeating step A) at least once, wherein the quaternary organic ammonium carbonate and/or bicarbonate employed in this next step A) is at least partially sourced from the quaternary organic ammonium carbonate and/or bicarbonate obtained from the preceding step C).

Tetraethylammonium hydrogen carbonate: A cheap, efficient, and recyclable catalyst for transesterification reactions under solvent-free conditions

Tetraethylammonium hydrogen carbonate (TEAHC) was proven to be an efficient catalyst for transesterification reactions in the absence of solvent. The reaction between isopropenyl or ethyl acetate and an alcohol (not efficient in the absence of catalyst) was induced by the presence of TEAHC, which seems to assist the proton transfer from the alcohol to the ester, yielding the corresponding acetate in very good yields in the absence of any solvent. Moreover, the TEAHC can be recycled several times without significant loss in activity.

Epoxidation of alkenes with aqueous hydrogen peroxide and quaternary ammonium bicarbonate catalysts

A range of solid and liquid catalysts containing bicarbonate anions were synthesised and tested for the epoxidation of alkenes with aqueous hydrogen peroxide. The combination of bicarbonate anions and quaternary ammonium cations opens up for new catalytic systems that can help to overcome challenges with catalyst separation and reuse. Graphical Abstract: [Figure not available: see fulltext.]

Process for producing a high purity quaternary ammonium hydroxide

A process for production of high purity quaternary ammonium hydroxides, comprising electrolyzing quaternary ammonium hydrogencarbonates represented by the general formula: (wherein the symbols are as defined in the appended claims) in an electrolytic cell comprising an anode compartment and a cathode compartment defined by a cation exchange membrane. In accordance with this process, high purity quaternary ammonium hydroxides can be produced with high electrolytic efficiency and further without causing corrosion of equip-ment. Since the quaternary ammonium hydroxides produced by the present invention are of high purity, they can be effectively used as, for example, cleaners, etchants or developers for wafers in the production of IC and LSI in the field of electronics and semiconductors.