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Heck Coupling
The HECK REACTION (also called the MIZOROKI-HECK REACTION) is the chemical reaction of an unsaturated halide (or triflate ) with an alkene in the presence of a base and a palladium catalyst (or palladium nanomaterial-based catalyst ) to form a substituted alkene. It is named after Tsutomu Mizoroki and Richard F. Heck . Heck was awarded the 2010 Nobel Prize in Chemistry , which he shared with Ei-ichi Negishi and Akira Suzuki , for the discovery and development of this reaction. This reaction was the first example of a carbon-carbon bond-forming reaction that followed a Pd(0)/Pd(II) catalytic cycle, the same catalytic cycle that is seen in other Pd(0)-catalyzed cross-coupling reactions . The Heck reaction is of great importance, as it allows one to do substitution reactions on planar sp2-hybridized carbon atoms. THE HECK REACTIONThe reaction is performed in the presence of an organopalladium catalyst
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Stilbene
STILBENE may refer to one of the two stereoisomers of 1,2-diphenylethene: * (E)-Stilbene
(E)-Stilbene
(trans isomer) * (Z)-Stilbene (cis isomer)SEE ALSO * Stilbenoids , a class of molecules found in plants * 1,1-Diphenylethylene This set index page lists chemical compounds articles ass
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Styrene
STYRENE, also known as ETHENYLBENZENE, VINYLBENZENE, and PHENYLETHENE, is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid that evaporates easily and has a sweet smell, although high concentrations have a less pleasant odor. Styrene
Styrene
is the precursor to polystyrene and several copolymers. Approximately 25 million tonnes (55 billion pounds) of styrene were produced in 2010
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Methanol
METHANOL (/ˈmɛθənɒl/ ), also known as METHYL ALCOHOL among others, is a chemical with the formula C H 3O H (often abbreviated MeOH). Methanol
Methanol
acquired the name "WOOD ALCOHOL" because it was once produced chiefly as a byproduct of the destructive distillation of wood. Today, industrial methanol is produced in a catalytic process directly from carbon monoxide , carbon dioxide , and hydrogen . Methanol
Methanol
is the simplest alcohol , being only a methyl group linked to a hydroxyl group. It is a light, volatile , colorless, flammable liquid with a distinctive odor very similar to that of ethanol (drinking alcohol). However, unlike ethanol, methanol is highly toxic and unfit for consumption. At room temperature, it is a polar liquid , and is used as an antifreeze , solvent , fuel , and as a denaturant for ethanol . It is also used for producing biodiesel via transesterification reaction
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Autoclave
An AUTOCLAVE is a pressure chamber used to carry out industrial processes requiring elevated temperature and pressure different from ambient air pressure. Autoclaves are used in medical applications to perform sterilization and in the chemical industry to cure coatings and vulcanize rubber and for hydrothermal synthesis . They are also used in industrial applications, especially regarding composites, see autoclave (industrial) . Many autoclaves are used to sterilize equipment and supplies by subjecting them to high-pressure saturated steam at 121 °C (249 °F) for around 15–20 minutes depending on the size of the load and the contents. The autoclave was invented by Charles Chamberland in 1879, although a precursor known as the steam digester was created by Denis Papin in 1679. The name comes from Greek auto-, ultimately meaning self, and Latin clavis meaning key, thus a self-locking device
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Potassium Acetate
POTASSIUM ACETATE (KCH3COO) is the potassium salt of acetic acid . CONTENTS * 1 Preparation * 2 Applications * 2.1 Deicing * 2.2 Food additive * 2.3 Medicine and biochemistry * 2.4 Death penalty * 2.5 Industry * 3 Historical * 4 References * 5 External links PREPARATIONIt can be prepared by treating a potassium-containing base such as potassium hydroxide or potassium carbonate with acetic acid : CH3COOH + KOH → CH3COOK + H2O This sort of reaction is known as an acid-base neutralization reaction. Sesquihydrate in water solution (CH3COOK·1½H2O) begins to form semihydrate at 41.3 °C. Potassium acetate is the salt that forms along with water as acetic acid and potassium hydroxide are neutralized together. Conditions/substances to avoid are: moisture , heat , flames , ignition sources, and strong oxidizing agents
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Iodobenzene
IODOBENZENE is an organoiodine compound consisting of a benzene ring substituted with one iodine atom. It is useful as a synthetic intermediate in organic chemistry . It is a volatile colorless liquid, although aged samples appear yellowish. CONTENTS * 1 Preparation * 2 Reactions * 3 See also * 4 References * 5 Further reading PREPARATION Iodobenzene
Iodobenzene
is commercially available, but it can be prepared in the laboratory from aniline via the Sandmeyer reaction . In the first step, the amine functional group is diazotized with hydrochloric acid and sodium nitrite . Potassium iodide is added to the resultant phenyldiazonium chloride , causing nitrogen gas to evolve. The product is separated by steam distillation. Alternatively, it can be produced by refluxing iodine and nitric acid with benzene
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Sodium Acetate
SODIUM ACETATE, CH3COONa, also abbreviated Na O Ac , also known as SODIUM ETHANOATE, is the sodium salt of acetic acid . This colorless deliquescent salt has a wide range of uses. CONTENTS* 1 Applications * 1.1 Industrial * 1.2 Concrete longevity * 1.3 Food * 1.4 Buffer solution * 1.5 Heating pad * 2 Preparation * 3 Reactions * 4 References * 5 External links APPLICATIONSINDUSTRIALSodium acetate is used in the textile industry to neutralize sulfuric acid waste streams and also as a photoresist while using aniline dyes . It is also a pickling agent in chrome tanning and helps to impede vulcanization of chloroprene in synthetic rubber production. In processing cotton for disposable cotton pads, sodium acetate is used to eliminate the buildup of static electricity
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Phosphinooxazolines
PHOSPHINOOXAZOLINES (often abbreviated PHOX) are a class of chiral ligands used in asymmetric catalysis . Their complexes are particularly effective at generating single enatiomers in reactions involving highly symmetric transition states , such as allylic substitutions, which are typically difficult to perform stereoselectively. The ligands are bidentate and have been shown to be hemilabile with the softer P‑donor being more firmly bound than the harder N‑donor. CONTENTS * 1 Synthesis * 2 In catalysis * 2.1 Allylic substitutions * 2.2 Heck Reaction * 2.3 Asymmetric Hydrogenation * 3 See also * 4 References SYNTHESISThe synthesis of phosphinooxazolines is modular and it is not normally necessary to introduce the phosphine and oxazoline moieties in any particular order
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BINAP
BINAP
BINAP
(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) is an organophosphorus compound . This chiral ligand is widely used in asymmetric synthesis . It consists of a pair of 2-diphenylphosphinonaphthyl groups linked at the 1 and 1´ positions. This C2-symmetric framework lacks a stereogenic atom , but has axial chirality due to restricted rotation (atropisomerism ). The barrier to racemization is high due to steric hindrance, which limits rotation about the bond linking the naphthyl rings. The dihedral angle is approximately 90˚. USE AS LIGAND IN ASYMMETRIC CATALYSIS BINAP
BINAP
is used in organic synthesis for enantioselective transformations catalyzed by its complexes of ruthenium , rhodium , and palladium . As pioneered by Ryōji Noyori
Ryōji Noyori
and his co-workers, Rh complexes of BINAP
BINAP
are useful for the synthesis of (–)-menthol
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Triethylamine
TRIETHYLAMINE is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et 3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium , for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia and is also the smell of the hawthorn plant. Like diisopropylethylamine (Hünig’s base), triethylamine is commonly encountered in organic synthesis . CONTENTS * 1 Synthesis and properties * 2 Applications * 2.1 Niche uses * 3 References * 4 External links SYNTHESIS AND PROPERTIES Triethylamine
Triethylamine
is prepared by the alkylation of ammonia with ethanol : NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2O The pKa of protonated triethylamine is 10.75, and it can be used to prepare buffer solutions for that pH
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Potassium Carbonate
POTASSIUM CARBONATE (K2 CO3 ) is a white salt, soluble in water (insoluble in ethanol ) which forms a strongly alkaline solution. It can be made as the product of potassium hydroxide 's absorbent reaction with carbon dioxide . It is deliquescent , often appearing a damp or wet solid . Potassium
Potassium
carbonate is used in the production of soap and glass . CONTENTS * 1 History * 2 Production * 3 Applications * 4 References * 5 Bibliography * 6 External links HISTORY Potassium
Potassium
carbonate is the primary component of potash and the more refined PEARL ASH or salts of tartar. Historically, pearl ash was created by baking potash in a kiln to remove impurities. The fine, white powder remaining was the pearl ash. The first patent issued by the US Patent
Patent
Office was awarded to Samuel Hopkins in 1790 for an improved method of making potash and pearl ash
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Palladium Acetate
PALLADIUM(II) ACETATE is a chemical compound of palladium described by the formula n, abbreviated n. It is more reactive than the analogous platinum compound . Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions. CONTENTS * 1 Structure * 2 Preparation * 3 Catalysis * 4 Precursor to other Pd compounds * 5 See also * 6 References STRUCTUREWith a 1:2 stoichiometric ratio of palladium atoms and acetate ligands , the compound exists as molecular and polymeric forms. Pd achieves approximate square planar coordination in both forms. As prepared by Wilkinson and coworkers in 1965 and later characterized by Skapski and Smart in 1970 by single crystal X-ray diffraction, palladium(II) acetate is a red-brown solid that crystallizes as monoclinic plates
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Catalytic Cycle
In chemistry , a CATALYTIC CYCLE is a multistep reaction mechanism that involves a catalyst . The catalytic cycle is the main method for describing the role of catalysts in biochemistry , organometallic chemistry , bioinorganic chemistry , materials science, etc. Often such cycles show the conversion of a precatalyst to the catalyst. Since catalysts are regenerated, catalytic cycles are usually written as a sequence of chemical reactions in the form of a loop. In such loops, the initial step entails binding of one or more reactants by the catalyst, and the final step is the release of the product and regeneration of the catalyst. Articles on the Monsanto process, the Wacker process, and the Heck reaction show catalytic cycles. Catalytic cycle
Catalytic cycle
for conversion of A and B into C. A catalytic cycle is not necessarily a full reaction mechanism
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Sonogashira Coupling
The SONOGASHIRA REACTION is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds . It employs a palladium catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vinyl halide . R H + R X base, rt Pd cat., Cu cat. R R {displaystyle {begin{matrix}{}\{ce {R-!{equiv }!-H}}+{color {Red}{ce {R'}}}!-!{ce {X->R-!{equiv }!}}{color {Red}{ce {-R'}}}end{matrix}}} * R': Aryl or Vinyl * X: I, Br, Cl or OTfThe Sonogashira cross-coupling reaction has been employed in a wide variety of areas, due to its usefulness in the formation of carbon–carbon bonds. The reaction can be carried out under mild conditions, such as at room temperature, in aqueous media, and with a mild base, which has allowed for the use of the Sonogashira cross-coupling reaction in the synthesis of complex molecules
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Wacker Process
The WACKER PROCESS or the HOECHST-WACKER PROCESS (named after the chemical companies of the same name) refers to the oxidation of ethylene to acetaldehyde in the presence of palladium(II) chloride as the catalyst . This chemical reaction was one of the first homogeneous catalysis with organopalladium chemistry applied on an industrial scale. CONTENTS * 1 History * 2 Reaction mechanism * 2.1 Historical mechanistic studies * 3 Industrial process * 3.1 One-stage process * 3.2 Two-stage process * 4 Wacker–Tsuji oxidation * 5 References HISTORYThe development of the chemical process now known as the Wacker process began in 1956 at Wacker Chemie . At the time, many industrial compounds were produced from acetylene , derived from calcium carbide , an expensive and environmentally unfriendly technology
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