Phase-transfer Catalysis
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Phase-transfer Catalysis
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 heterogeneous catalysis. 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. By using a PTC process, one can achieve faster reactions, obtain higher conversions or yields, make fewer byproducts, eliminate the need for expensive or dangerous solvents that will dissolve all the reactants in one phase, eliminate the need for expensive raw materials and/or minimize waste problems. Phase-transfer catalysts are especially useful in green chemistry—by allowing the use of water, the n ...
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Chemistry
Chemistry is the scientific study of the properties and behavior of matter. It is a natural science that covers the elements that make up matter to the compounds made of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they undergo during a reaction with other substances. Chemistry also addresses the nature of chemical bonds in chemical compounds. In the scope of its subject, chemistry occupies an intermediate position between physics and biology. It is sometimes called the central science because it provides a foundation for understanding both basic and applied scientific disciplines at a fundamental level. For example, chemistry explains aspects of plant growth ( botany), the formation of igneous rocks ( geology), how atmospheric ozone is formed and how environmental pollutants are degraded ( ecology), the properties of the soil on the moon ( cosmochemistry), how medications work ( pharmacology), and how to collec ...
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Hydrophilic
A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are not attracted to water and may seem to be repelled by it. Hygroscopics ''are'' attracted to water, but are not dissolved by water. Molecules A hydrophilic molecule or portion of a molecule is one whose interactions with water and other polar substances are more thermodynamically favorable than their interactions with oil or other hydrophobic solvents. They are typically charge-polarized and capable of hydrogen bonding. This makes these molecules soluble not only in water but also in other polar solvents. Hydrophilic molecules (and portions of molecules) can be contrasted with hydrophobic molecules (and portions of molecules). In some cases, both hydrophilic and hydrophobic properties occur in a single molecule. An example of these ...
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Polyethylene Glycol
Polyethylene glycol (PEG; ) is a polyether compound derived from petroleum with many applications, from industrial manufacturing to medicine. PEG is also known as polyethylene oxide (PEO) or polyoxyethylene (POE), depending on its molecular weight. The structure of PEG is commonly expressed as H−(O−CH2−CH2)n−OH. Uses Medical uses * Pharmaceutical-grade PEG is used as an excipient in many pharmaceutical products, in oral, topical, and parenteral dosage forms. * PEG is the basis of a number of laxatives (as ''MiraLax''). Whole bowel irrigation with polyethylene glycol and added electrolytes is used for bowel preparation before surgery or colonoscopy. * PEG is used in medicines for treating disimpaction and maintenance therapy for children with constipation. * When attached to various protein medications or drug carriers, polyethylene glycol of suitable length slows down their clearance from the blood. * The possibility that PEG could be used to fuse axons is being ex ...
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Crown Ether
In organic chemistry, crown ethers are cyclic chemical compounds that consist of a ring containing several ether groups (). The most common crown ethers are cyclic oligomers of ethylene oxide, the repeating unit being ethyleneoxy, i.e., . Important members of this series are the tetramer (''n'' = 4), the pentamer (''n'' = 5), and the hexamer (''n'' = 6). The term "crown" refers to the resemblance between the structure of a crown ether bound to a cation, and a crown sitting on a person's head. The first number in a crown ether's name refers to the number of atoms in the cycle, and the second number refers to the number of those atoms that are oxygen. Crown ethers are much broader than the oligomers of ethylene oxide; an important group are derived from catechol. Crown ethers strongly bind certain cations, forming complexes. The oxygen atoms are well situated to coordinate with a cation located at the interior of the ring, whereas the exterior of ...
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Methyltrioctylammonium Chloride
Aliquat 336 (Starks' catalyst) is a quaternary ammonium salt used as a phase transfer catalyst and metal extraction reagent. It contains a mixture of C8 (octyl) and C10 (decyl) chains with C8 predominating. It is an ionic liquid. Applications Organic Chemistry Aliquat 336 is used as a phase transfer catalyst, including in the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid. This reaction is more environmentally friendly. It is an example of green chemistry, compared with the traditional method of oxidizing cyclohexanol or cyclohexanone with nitric acid or potassium permanganate, which produce hazardous wastes. Aliquat 336 was used in the total synthesis of manzamine A by Darren Dixon in an early step to the electrophile. Solvent extraction of metals {{Main, Liquid–liquid extraction Aliquat 336 has been used for the extraction of metals, it does so by acting as a liquid anion exchanger. It is often used while diluted in hydrocarbon solvents such as aromatic ker ...
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Tetra-n-butylammonium Bromide
Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst. It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white solid. In addition to being cheap, tetrabutylammonium bromide is also environmentally friendly, has a greater degree of selectivity, is operationally simple, non-corrosive, and can be recycled easily as well. Preparation and reactions Tetrabutylammonium bromide can be prepared by the alkylation of tributylamine with 1-bromobutane. Tetrabutylammonium bromide is used to prepare other salts of the tetrabutylammonium cation by salt metathesis reactions., , ;. It serves as a source of bromide ions for substitution reactions. It is one of a commonly-used phase transfer catalyst. As its melting point is just over 100 °C and decreases in the presence of other reagents, it can be considered an ionic liquid. Role in semi-clathrate formation TBAB ...
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Cyanide
Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms. In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. In inorganic cyanides, the cyanide group is present as the anion . Soluble salts such as sodium cyanide (NaCN) and potassium cyanide (KCN) are highly toxic. Hydrocyanic acid, also known as hydrogen cyanide, or HCN, is a highly volatile liquid that is produced on a large scale industrially. It is obtained by acidification of cyanide salts. Organic cyanides are usually called nitriles. In nitriles, the group is linked by a covalent bond to carbon. For example, in acetonitrile (), the cyanide group is bonded to methyl (). Although nitriles generally do not release cyanide ions, the cyanohydrins do and are thus rather toxic. Bonding The cyanide ion is isoelectronic with carbon monoxi ...
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Ether
In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether" (). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin. Structure and bonding Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141  pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water ...
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Sodium Cyanide
Sodium cyanide is a poisonous compound with the formula Na C N. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its high reactivity toward metals. It is a moderately strong base. Production and chemical properties Sodium cyanide is produced by treating hydrogen cyanide with sodium hydroxide: :HCN + NaOH → NaCN + H2O Worldwide production was estimated at 500,000 tons in the year 2006. Formerly it was prepared by the Castner process involving the reaction of sodium amide with carbon at elevated temperatures. : NaNH2 + C → NaCN + H2 The structure of solid NaCN is related to that of sodium chloride. The anions and cations are each six-coordinate. Potassium cyanide (KCN) adopts a similar structure. When treated with acid, it forms the toxic gas hydrogen cyanide: : NaCN + H+ → HCN + Na+ Because the salt is derived from a weak acid ...
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Nucleophilic Substitution
In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The molecule that contains the electrophile and the leaving functional group is called the substrate. The most general form of the reaction may be given as the following: :\text\mathbf + \ce + \text\mathbf The electron pair (:) from the nucleophile (Nuc) attacks the substrate () and bonds with it. Simultaneously, the leaving group (LG) departs with an electron pair. The principal product in this case is . The nucleophile may be electrically neutral or negatively charged, whereas the substrate is typically neutral or positively charged. An example of nucleophilic substitution is the hydrolysis of an alkyl bromide, R-Br under basic conditions, where the attacking nucleophile is hydroxyl () and the leaving group is bromide (). :R-Br + OH ...
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Phosphine Oxide
Phosphine oxides are phosphorus compounds with the formula OPX3. When X = alkyl or aryl, these are organophosphine oxides. Triphenylphosphine oxide is an example. An inorganic phosphine oxide is phosphoryl chloride (POCl3). Structure and bonding Tertiary phosphine oxides Tertiary phosphine oxides are the most commonly encountered phosphine oxides. With the formula R3PO, they are tetrahedral compounds. They are usually prepared by oxidation of tertiary phosphines. The P-O bond is short and polar. According to molecular orbital theory, the short P–O bond is attributed to the donation of the lone pair electrons from oxygen p-orbitals to the antibonding phosphorus-carbon bonds. The nature of the P–O bond was once hotly debated. Some discussions invoked a role for phosphorus-centered d-orbitals in bonding, but this analysis is not supported by computational analyses. In terms of simple Lewis structure, the bond is more accurately represented as a dative bond, as is currently ...
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Phosphonium Salt
In polyatomic cations with the chemical formula (where R is a hydrogen or an alkyl, aryl, or halide group). These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions. Types of phosphonium cations Protonated phosphines The parent phosphonium is as found in the iodide salt, phosphonium iodide. Salts of the parent are rarely encountered, but this ion is an intermediate in the preparation of the industrially useful tetrakis(hydroxymethyl)phosphonium chloride: :PH3 + HCl + 4 CH2O → Many organophosphonium salts are produced by protonation of primary, secondary, and tertiary phosphines: :PR3 + H+ → The basicity of phosphines follows the usual trends, with R = alkyl being more basic than R = aryl. Tetraorganophosphonium cations The most common phosphonium compounds have four organic substituents attached to phosphorus. The quaternary phosphonium cations include tetraphenylphosphonium, (C6H5)4P+ and tetramethylphosphoniu ...
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