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Names | |
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IUPAC name N,N,N-Tripropylpropan-1-aminium | |
Other names Tetrapropylammonium Tetrapropylazanium Tetra-n-propylammonium TPA | |
Identifiers | |
3D model (JSmol) | |
1748523 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C12H28N+ | |
Molar mass | 186.362 g·mol−1 |
Structure | |
Tetrahedral | |
Related compounds | |
Other cations |
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Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Tetrapropylammonium (TPA) is a quaternary ammonium cation with the formula [N(C3H7)4]+, also denoted [NPr4]+ (where Pr = propyl group). It is a precursor to several significant industrial and laboratory catalysts.
TPA is chemically similar to other quaternary ammonium cations with saturated alkyl groups. As such, it is highly electrochemically stable, degrading only in the presence of particularly strong bases and nucleophiles. [1]
It is isoelectronic with tetrapropyltin and the tetrapropylboranuide anion.
Like other quaternary ammonium cations, TPA is prepared by the alkylation of the corresponding ammonia analogue, tripropylamine. Treatment of the amine with a primary propyl halide such as n-bromopropane yields the corresponding TPA halide salt in a Menshutkin reaction:
The halide salts are then converted to the more industrially valuable hydroxide by reaction with aqueous silver oxide, electrolysis, ion-exchange resin, or electrodialysis. [2]
The tetrapropylammonium cation is used as a structure-directing agent in the production of synthetic zeolites, in particular ZSM-5 [3] and titanium-bearing TS-1 catalysts. [4] After synthesis, TPA is removed by thermolysis. [5]
The TPA salt tetrapropylammonium perruthenate (TPAP) is an effective and highly selective oxidiser, with numerous applications in organic synthesis. [6] [7] Combined with a cooxidant, it serves as a catalyst for the oxidation of primary and secondary alcohols to aldehydes and ketones.
Catalysis is the increase in rate of a chemical reaction due to an added substance known as a catalyst. Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst.
Zeolite is a family of several microporous, crystalline aluminosilicate materials commonly used as commercial adsorbents and catalysts. They mainly consist of silicon, aluminium, oxygen, and have the general formula Mn+
1/n(AlO
2)−
(SiO
2)
x・yH
2O where Mn+
1/n is either a metal ion or H+.
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.
In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At its simplest, it's a useful way of converting alkanes, which are relatively inert and thus low-valued, to olefins, which are reactive and thus more valuable. Alkenes are precursors to aldehydes, alcohols, polymers, and aromatics. As a problematic reaction, the fouling and inactivation of many catalysts arises via coking, which is the dehydrogenative polymerization of organic substrates.
The Suzuki reaction or Suzuki coupling is an organic reaction that uses a palladium complex catalyst to cross-couple a boronic acid to an organohalide. It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of noble metal catalysis in organic synthesis. This reaction is sometimes telescoped with the related Miyaura borylation; the combination is the Suzuki–Miyaura reaction. It is widely used to synthesize polyolefins, styrenes, and substituted biphenyls.
In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.
Tetrapropylammonium perruthenate (TPAP or TPAPR) is the chemical compound described by the formula N(C3H7)4RuO4. Sometimes known as the Ley–Griffith reagent, this ruthenium compound is used as a reagent in organic synthesis. This salt consists of the tetrapropylammonium cation and the perruthenate anion, RuO−4.
In chemistry, a phase-transfer catalyst or PTC is a catalyst that facilitates the transition of a reactant from one phase into another phase where reaction occurs. Phase-transfer catalysis is a special form of catalysis and can act through homogeneous catalysis or heterogeneous catalysis methods depending on the catalyst used. Ionic reactants are often soluble in an aqueous phase but insoluble in an organic phase in the absence of the phase-transfer catalyst. The catalyst functions like a detergent for solubilizing the salts into the organic phase. Phase-transfer catalysis refers to the acceleration of the reaction upon the addition of the phase-transfer catalyst.
In organic chemistry, the Kumada coupling is a type of cross coupling reaction, useful for generating carbon–carbon bonds by the reaction of a Grignard reagent and an organic halide. The procedure uses transition metal catalysts, typically nickel or palladium, to couple a combination of two alkyl, aryl or vinyl groups. The groups of Robert Corriu and Makoto Kumada reported the reaction independently in 1972.
ZSM-5, Zeolite Socony Mobil–5 (framework type MFI from ZSM-5 (five)), is an aluminosilicate zeolite belonging to the pentasil family of zeolites. Its chemical formula is NanAlnSi96–nO192·16H2O (0<n<27). Patented by Mobil Oil Company in 1975, it is widely used in the petroleum industry as a heterogeneous catalyst for hydrocarbon isomerization reactions.
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−. It 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, it has fewer synthetic chemical applications than quaternary ammonium salts containing longer N-alkyl substituents, which are used extensively as phase-transfer catalysts.
Organogold chemistry is the study of compounds containing gold–carbon bonds. They are studied in academic research, but have not received widespread use otherwise. The dominant oxidation states for organogold compounds are I with coordination number 2 and a linear molecular geometry and III with CN = 4 and a square planar molecular geometry.
Photoredox catalysis is a branch of photochemistry that uses single-electron transfer. Photoredox catalysts are generally drawn from three classes of materials: transition-metal complexes, organic dyes, and semiconductors. While organic photoredox catalysts were dominant throughout the 1990s and early 2000s, soluble transition-metal complexes are more commonly used today.
Praseodymium(III,IV) oxide is the inorganic compound with the formula Pr6O11 that is insoluble in water. It has a cubic fluorite structure. It is the most stable form of praseodymium oxide at ambient temperature and pressure.
Raymond John Gorte is an American chemical engineer, currently the Russel Pearce and Elizabeth Crimian Heuer Endowed Professor of Chemical and Biomolecular Engineering (CBE) and Materials Science & Engineering (MSE) at the University of Pennsylvania. Throughout his career at the University of Pennsylvania and the University of Minnesota, he has advanced the study of fuel cells and catalysts including heterogeneous metals and zeolite materials. He is a member of the U.S. National Academy of Engineering.
Water oxidation catalysis (WOC) is the acceleration (catalysis) of the conversion of water into oxygen and protons:
Steven L. Suib is an American inorganic chemist, academic and researcher. He is a Board of Trustees Distinguished Professor of Chemistry at University of Connecticut. He is a director of the Institute of Materials Science and of the Center for Advanced Microscopy and Materials Analysis.
Alexis Tarassov Bell is an American chemical engineer. He is currently the Dow professor of Sustainable Chemistry in the Department of Chemical and Biomolecular Engineering in UC Berkeley's college of chemistry. He is also the Faculty Senior Scientist at Lawrence Berkeley National Laboratory. He is known for his work with heterogenous catalysts and characterizing the mechanisms of these reactions on a quantum level.
Perruthenate is an oxyanion of ruthenium in its +7 oxidation state. It is a mild oxidising agent useful in organic synthesis.
Ammonium hypoiodites are a class of reactive intermediates used in certain organic oxidation reactions. They consist of either ammonium itself or an alkylammonium with various substituents as cation, paired with a hypoiodite anion as the active oxidant. The hypoiodite is generated in situ from the analogous iodide reagent using peroxides, oxone, peracids, or other strong oxidizing agents. The hypoiodite is then capable of oxidizing various organic substrates. The iodide is regenerated, meaning the reaction runs with the iodide/hypoiodite as a catalyst in the presence of excess of the original strong oxidizing agent.