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Terephthalonitrile
1,4-Dicyanobenzene is an organic compound with the formula C6H4(CN)2. Two other isomers exist, phthalonitrile and isophthalonitrile. All three isomers are produced commercially by ammoxidation of the corresponding xylene isomers. 1,4-Dicyanobenzene is a colorless or white solid with low solubility in water. Hydrogenation of isophthalonitrile affords p-xylylenediamine. 1,4-dicyanobenzene is electrochemically active, forming a stable persistent radical at anodes. For this reason, it has been used as a catalyst for automated reaction discovery Automation describes a wide range of technologies that reduce human intervention in processes, namely by predetermining decision criteria, subprocess relationships, and related actions, as well as embodying those predeterminations in machines ..., testing whether other species are redox active. Safety The (rat, oral) is 6400 mg/kg. References {{DEFAULTSORT:Dicyanobenzene, 1,4- Benzonitriles ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Livin ...
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Phthalonitrile
Phthalonitrile is an organic compound with the formula C6H4(CN)2, which is an off-white crystal solid at room temperature. It is a derivative of benzene, containing two adjacent nitrile groups. The compound has low solubility in water but is soluble in common organic solvents. The compound is used as a precursor to phthalocyanine and other pigments, fluorescent brighteners, and photographic sensitizers. Synthesis Phthalonitrile is produced industrially in a single-stage continuous process, by the ammoxidation of ''o''-xylene at 480 °C. The reaction is catalyzed by vanadium oxide-antimony-oxide in a fluidized bed reactor.Lorz, Peter M. "Phthalic Acid and Derivatives" in Ulmanns Encyclopedia of Industrial Chemistry. Wiley-VCH: Weinheim, 2002. . : Phthalonitrile was first described in 1896 by Johannes Pinnow. It was noted as a byproduct of the synthesis of ortho-dicyanodiazoamidobenzene via the reaction of ortho-amidobenzonitrile hydrochloride, sodium nitrite, and hydroc ...
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Isophthalonitrile
Isophthalonitrile is an organic compound with the formula C6H4(CN)2. Two other isomers exist, phthalonitrile and terephthalonitrile. All three isomers are produced commercially by ammoxidation of the corresponding xylene isomers. Isophthalonitrile is a colorless or white solid with low solubility in water.{{Ullmann, doi=10.1002/14356007.a17_363, title=Nitriles, year=2000, last1=Pollak, first1=Peter, last2=Romeder, first2=Gérard, last3=Hagedorn, first3=Ferdinand, last4=Gelbke, first4=Heinz-Peter, isbn=3527306730 Hydrogenation of isophthalonitrile affords m-xylylenediamine, a curing agent in epoxy resins and a component of some urethanes. Safety LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is the ... (rat, oral) is 288 mg/kg. References Benzonitriles ...
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Ammoxidation
In organic chemistry, ammoxidation is a process for the production of nitriles () using ammonia () and oxygen (). It is sometimes called the SOHIO process, acknowledging that ammoxidation was developed at Standard Oil of Ohio. The usual substrates are alkenes. Several million tons of acrylonitrile are produced in this way annually: :CH3CH=CH2 + 3/2 O2 + NH3 -> N#CCH=CH2 + 3 H2O Scope Ammoxidation of alkenes exploits the weak C-H bonds that are located in the allylic position of unsaturated hydrocarbons. Benzylic C-H bonds are also susceptible to ammoxidation, reflecting the weakness of their C-H bonds. Benzonitrile is produced from toluene, and phthalonitriles are produced from xylenes. The reaction represents a partial oxidation. Many byproducts are generated, but the feedstocks are often simple, which compensates for these losses. Additionally, some byproducts are useful or recyclable. For the production of acrylonitrile, byproducts include hydrogen cyanide, acrole ...
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Xylene
In organic chemistry, xylene or xylol (; IUPAC name: dimethylbenzene) are any of three organic compounds with the formula . They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are substituted determines which of three structural isomers results. It is a colorless, flammable, slightly greasy liquid of great industrial value. The mixture is referred to as both xylene and, more precisely, xylenes. Mixed xylenes refers to a mixture of the xylenes plus ethylbenzene. The four compounds have identical empirical formulas . Typically the four compounds are produced together by various catalytic reforming and pyrolysis methods. Occurrence and production Xylenes are an important petrochemical produced by catalytic reforming and also by coal carbonisation in the manufacture of coke fuel. They also occur in crude oil in concentrations of about 0.5–1%, depending on the source. Small quantities occur in gasoline and aircraft f ...
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Electrochemistry
Electrochemistry is the branch of physical chemistry concerned with the relationship between electrical potential difference, as a measurable and quantitative phenomenon, and identifiable chemical change, with the potential difference as an outcome of a particular chemical change, or vice versa. These reactions involve electrons moving via an electronically-conducting phase (typically an external electrical circuit, but not necessarily, as in electroless plating) between electrodes separated by an ionically conducting and electronically insulating electrolyte (or ionic species in a solution). When a chemical reaction is driven by an electrical potential difference, as in electrolysis, or if a potential difference results from a chemical reaction as in an electric battery or fuel cell, it is called an ''electrochemical'' reaction. Unlike in other chemical reactions, in electrochemical reactions electrons are not transferred directly between atoms, ions, or molecules, but via ...
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Persistent Radical
In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired valence electron. With some exceptions, these unpaired electrons make radicals highly chemically reactive. Many radicals spontaneously dimerize. Most organic radicals have short lifetimes. A notable example of a radical is the hydroxyl radical (HO·), a molecule that has one unpaired electron on the oxygen atom. Two other examples are triplet oxygen and triplet carbene (꞉) which have two unpaired electrons. Radicals may be generated in a number of ways, but typical methods involve redox reactions. Ionizing radiation, heat, electrical discharges, and electrolysis are known to produce radicals. Radicals are intermediates in many chemical reactions, more so than is apparent from the balanced equations. Radicals are important in combustion, atmospheric chemistry, polymerization, plasma chemistry, biochemistry, and many other chemical processes. A majority ...
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Anode
An anode is an electrode of a polarized electrical device through which conventional current enters the device. This contrasts with a cathode, an electrode of the device through which conventional current leaves the device. A common mnemonic is ACID, for "anode current into device". The direction of conventional current (the flow of positive charges) in a circuit is opposite to the direction of electron flow, so (negatively charged) electrons flow from the anode of a galvanic cell, into an outside or external circuit connected to the cell. For example, the end of a household battery marked with a "+" is the cathode (while discharging). In both a galvanic cell and an electrolytic cell, the anode is the electrode at which the oxidation reaction occurs. In a galvanic cell the anode is the wire or plate having excess negative charge as a result of the oxidation reaction. In an electrolytic cell, the anode is the wire or plate upon which excess positive charge is imposed. A ...
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Automated Reaction Discovery
Automation describes a wide range of technologies that reduce human intervention in processes, namely by predetermining decision criteria, subprocess relationships, and related actions, as well as embodying those predeterminations in machines. Automation has been achieved by various means including mechanical, hydraulic, pneumatic, electrical, electronic devices, and computers, usually in combination. Complicated systems, such as modern factories, airplanes, and ships typically use combinations of all of these techniques. The benefit of automation includes labor savings, reducing waste, savings in electricity costs, savings in material costs, and improvements to quality, accuracy, and precision. Automation includes the use of various equipment and control systems such as machinery, processes in factories, boilers, and heat-treating ovens, switching on telephone networks, steering, and stabilization of ships, aircraft, and other applications and vehicles with reduced human int ...
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