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Tetramethylammonium chloride is the phase transfer catalyst in organic synthesis phase with its catalytic activity being stronger than triphenylphosphine and triethylamine.
At room temperature, Tetramethylammonium chloride is a white crystalline powder, and is volatile, irritant, and easy to absorb moisture.
Tetramethylammonium chloride is easily soluble in methanol, soluble in water and hot ethanol but insoluble in ether and chloroform.
CAS: 75-57-0
MF: C4H12ClN
MW: 109.6
EINECS: 200-880-8
Synonyms:Ammonium, tetramethyl-, chloride;Methanaminium, N,N,N-trimethyl-, chloride;TETRAMETHYLAMMONIUM CHLORIDETETRAMETHYLAMMONIUM CHLORIDETETRAMETHYLAMMONIUM CHLORIDETETRAMETHYLAMMONIUM CHLORIDE;Methanaminium,N,N,N-trimethyl-,chloride;n,n,n-trimethyl-methanaminiuchloride;tetramethyl-ammoniuchloride;tetraminechloride;USAF AN-8
Being heated to above 230 °C causes Tetramethylammonium chloride's decomposition into trimethylamine and methyl chloride.
Median lethal dose (mice, intraperitoneal) is around 25mg/kg.
Tetramethylammonium chloride is also used for the synthesis of liquid crystal epoxy compound, and Pope and polarographic analysis, as well as electronic industry.
Tetramethylammonium chloride is an organic molecular entity.
Tetramethylammonium chloride is a quaternary ammonium salt commonly used as a catalyst due to its thermal stability and also tolerance towards strong aqueous bases or nucleophiles.
Tetramethylammonium chloride is one of the simplest quaternary ammonium salts, with four methyl groups tetrahedrally attached to the central N.
The chemical formula (CH3)4N+Cl− is often abbreviated further as Me4N+Cl−.
Tetramethylammonium chloride is a hygroscopic colourless solid that is soluble in water and polar organic solvents.
Tetramethylammonium chloride is a major industrial chemical, being used widely as a chemical reagent and also as a low-residue bactericide in such processes as hydrofracking.
In the laboratory, Tetramethylammonium chloride has fewer synthetic chemical applications than quaternary ammonium salts containing longer N-alkyl substituents, which are used extensively as phase-transfer catalysts.
Tetramethylammonium chloride is a kind of organic base, and has a broad range of application in the field of both industry and scientific research.
In our own country, Tetramethylammonium chloride is mainly used as the catalyst in the synthesis of organic silicon products, such as synthetic silicone oil, silicone rubber, and silicone resin.
Although Tetramethylammonium chloride has a low usage amount, but it can significantly affect both the yield and quality of the product.
In abroad, Tetramethylammonium chloride is mainly used for polyester-based polymers, textiles, plastics, food, leather, wood processing, electroplating, and some kinds of microorganisms.
Now Tetramethylammonium chloride has entered the advanced technology areas.
For example, in the field of manufacturing industry of electronic circuit and microscopic sheets production, Tetramethylammonium chloride can be used as the cleaning agent of integrated circuit board as well as the anisotropic corrosive agents of the Si-SiO2 interface in semiconductor microfabrication technique.
With the development of science and technology, the requirements of this type of chemicals are also increasing, posing higher requirements for both the quality and the quantity of the Tetramethylammonium chloride.
The basic principle of using electrolytic method for preparation of Tetramethylammonium chloride is that the aqueous solution of tetramethylammonium chloride in the anode compartment of the electrolytic bath, under the action of the electric force, has its chloride ions migrate to the direction of anode until discharge of anode occurs to generate chlorine.
Meanwhile, because of the selective permeability of the ion-exchange membrane, chloride can’t penetrate through the ion-exchange membrane through diffusion.
Instead, only tetramethylammonium ions can selectively penetrate into the cathode compartment through, and be enriched over there.
The water molecule in the electrolyzer cathode chamber is decomposed into hydrogen and hydroxyl ions.
The latter one exactly binds to the tetramethylammonium ions migrated from the anode chamber to generate Tetramethylammonium chloride.
With the increase of electricity, Tetramethylammonium chloride concentration continues to improve, finally achieving the desired final concentration of crude.
The anodic electrochemical reaction is:
(CH3) 4NCl → (CH3) 4N ++ Clˉ2Clˉ-2e → Cl2 ↑
The cathodic electrochemical reaction is:
H2O → H + + OHˉ (CH3) 4N ++ OHˉ → (CH3) 4NOH 2H ++ 2e → H2 ↑
The total reaction is:
2 (CH3) 4NCl + 2H2O → 2 (CH3) 4NOH + H2 ↑ + Cl2 ↑
The hydrogen generated during electrolysis is vented with the resulting chlorine absorbed by alkaline solution to generate sodium hypochlorite which is major raw materials for producing bleach.
Therefore, this method of producing Tetramethylammonium chloride is simple with high purity and causing no environmental pollution.
Tetramethylammonium chloride Chemical Properties
Melting point: >300 °C (lit.)
Boiling point: 165.26°C (rough estimate)
density: 1,17 g/cm3
refractive index: 1.5320 (estimate)
storage temp.: Store below +30°C.
solubility methanol: 0.1 g/mL, clear, colorless
form: Hygroscopic Crystalline Powder
color: White to ivory
Specific Gravity: 1.169
Odor: Odorless
PH Range: 6 - 8
PH: 6-8 (100g/l, H2O, 20℃)
Water Solubility: >60 g/100 mL (20 ºC)
Sensitive: Hygroscopic
λmax λ: 260 nm Amax: 0.02
λ: 280 nm Amax: 0.02
BRN : 2496575
Stability: Stable. Incompatible with strong oxidizing agents, water. Hygroscopic.
CAS DataBase Reference: 75-57-0(CAS DataBase Reference)
NIST Chemistry Reference: Tetramethylammonium chloride(75-57-0)
EPA Substance Registry System: Tetramethylammonium chloride (75-57-0)
Preparation and laboratory uses
Tetramethylammonium chloride is efficiently produced by the reaction of trimethylamine and methyl chloride.
N(CH3)3 + CH3Cl → N(CH3)4+Cl−
Tetramethylammonium chloride is produced by the alkylation of ammonium chloride with dimethyl carbonate in the presence of an ionic liquid catalyst.
Except under extraordinary conditions, Tetramethylammonium chloride is typically employed as a source of the inert counter cation Me4N+.
Similarly, Tetramethylammonium chloride serves as a lipophilic precipitating agent.
In low concentrations, Tetramethylammonium chloride is used in polymerase chain reactions to increase yields and specificity.
Tetramethylammonium chloride has been shown to enhance yields 5–10 fold at 60mM by stabilizing the AT base pairs.
Uses
1. Tetramethylammonium chloride can be used as polarographic analysis reagents which is widely used in the electronics industry.
2. Tetramethylammonium chloride is the phase transfer catalyst in organic synthesis with its catalytic activity being stronger than triphenylphosphine and triethylamine.
At room temperature, Tetramethylammonium chloride is a white crystalline powder, and is volatile, irritant, and easy to absorb moisture.
Tetramethylammonium chloride is easily soluble in methanol, soluble in water and hot ethanol but insoluble in ether and chloroform.
Being heated to above 230 °C causes its decomposition into trimethylamine and methyl chloride.
Median lethal dose (mice, intraperitoneal) is around 25mg/kg.
Tetramethylammonium chloride is also used for the synthesis of liquid crystal epoxy compound, and Pope and polarographic analysis, as well as electronic industry.
Tetramethylammonium chloride along with N-hydroxyphthalimide and xanthone may be used as an efficient chloride catalytic system for the aerobic oxidation of hydrocarbons to form the corresponding oxygenated compounds.
Tetramethylammonium chloride may also be used as a phase transfer catalyst for the synthesis of aryl fluorides via selective chloride/fluoride exchange reaction of activated aryl chlorides with potassium fluoride in solid-liquid phase.
Tetramethylammonium chloride may be used in ion-exchange procedures to show the increase of pH in understanding the chemical behaviour of catalyst [CTA]Si-MCM-41 using Knoevenagel condensation model.
