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Tert-butyl Hydroperoxide
''tert''-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is one of the most widely used hydroperoxides in a variety of oxidation processes, for example the Halcon process. It is normally supplied as a 69–70% aqueous solution. Compared to hydrogen peroxide and organic peracids, ''tert''-butyl hydroperoxide is less reactive and more soluble in organic solvents. Overall, it is renowned for the convenient handling properties of its solutions. Its solutions in organic solvents are highly stable. Application Industrially, ''tert''-butyl hydroperoxide is used to prepare propylene oxide. In the Halcon process, molybdenum-based catalysts are used for this reaction: :(CH3)3COOH + CH2=CHCH3 → (CH3)3COH + CH2OCHCH3 The byproduct t-butanol, which can be dehydrated to isobutene and converted to MTBE. On a much smaller scale, ''tert''-butyl hydroperoxide is used to produce some fine chemicals by the Sharpless epoxidation. Synthesis and pro ...
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Hydroperoxides
Hydroperoxides or peroxols are compounds containing the hydroperoxide functional group (ROOH). If the R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds. Properties The O−O bond length in peroxides is about 1.45  Å, and the R−O−O angles (R = H, C) are about 110° (water-like). Characteristically, the C−O−O−H dihedral angles are about 120°. The O−O bond is relatively weak, with a bond dissociation energy of , less than half the strengths of C−C, C−H, and C−O bonds. Hydroperoxides are typically more volatile than the corresponding alcohols: * ''tert''-BuOOH (b.p. 36°C) vs ''tert''-BuOH (b.p. 82-83°C) * CH3OOH (b.p. 46°C) vs CH3OH (b.p. 65°C * cumene hydroperoxide (b.p. 153°C) vs cumyl alcohol (b.p. 202°C) Misc ...
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Isobutane
Isobutane, also known as ''i''-butane, 2-methylpropane or methylpropane, is a chemical compound with molecular formula HC(CH3)3. It is an isomer of butane. Isobutane is a colourless, odourless gas. It is the simplest alkane with a tertiary carbon atom. Isobutane is used as a precursor molecule in the petrochemical industry, for example in the synthesis of isooctane. Production Isobutane is obtained by isomerization of butane. : Uses Isobutane is the principal feedstock in alkylation units of refineries. Using isobutane, gasoline-grade "blendstocks" are generated with high branching for good combustion characteristics. Typical products created with isobutane are 2,4-dimethylpentane and especially 2,2,4-trimethylpentane. Solvent In the Chevron Phillips slurry process for making high-density polyethylene, isobutane is used as a diluent. As the slurried polyethylene is removed, isobutane is "flashed" off, and condensed, and recycled back into the loop reactor for this purpose. ...
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Reagents For Organic Chemistry
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a substance ''consumed'' in the course of a chemical reaction. ''Solvents'', though involved in the reaction mechanism, are usually not called reactants. Similarly, '' catalysts'' are not consumed by the reaction, so they are not reactants. In biochemistry, especially in connection with enzyme-catalyzed reactions, the reactants are commonly called substrates. Definitions Organic chemistry In organic chemistry, the term "reagent" denotes a chemical ingredient (a compound or mixture, typically of inorganic or small organic molecules) introduced to cause the desired transformation of an organic substance. Examples include the Collins reagent, Fenton's reagent, and Grignard reagents. Analytical chemistry In analytical chemistry, a reage ...
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Hydroperoxides
Hydroperoxides or peroxols are compounds containing the hydroperoxide functional group (ROOH). If the R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds. Properties The O−O bond length in peroxides is about 1.45  Å, and the R−O−O angles (R = H, C) are about 110° (water-like). Characteristically, the C−O−O−H dihedral angles are about 120°. The O−O bond is relatively weak, with a bond dissociation energy of , less than half the strengths of C−C, C−H, and C−O bonds. Hydroperoxides are typically more volatile than the corresponding alcohols: * ''tert''-BuOOH (b.p. 36°C) vs ''tert''-BuOH (b.p. 82-83°C) * CH3OOH (b.p. 46°C) vs CH3OH (b.p. 65°C * cumene hydroperoxide (b.p. 153°C) vs cumyl alcohol (b.p. 202°C) Misc ...
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Di-tert-butyl Peroxide
Di-''tert''-butyl peroxide or DTBP is an organic compound consisting of a peroxide group bonded to two tert-butyl groups. It is one of the most stable organic peroxides, due to the ''tert''-butyl groups being bulky. It is a colorless liquid. Reactions The peroxide bond undergoes homolysis at temperatures above 100 °C. For this reason di-''tert''-butyl peroxide is commonly used as a radical initiator in organic synthesis and polymer chemistry. The decomposition reaction proceeds via the generation of methyl radicals. :(CH3)3COOC(CH3)3 → 2 (CH3)3CO• :(CH3)3CO• → (CH3)2CO + :2 → C2H6 DTBP can in principle be used in engines where oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as ... is limited, since the molecule supplies both the oxidizer and the fuel. ...
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Oxidant
An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxidizer is any substance that oxidizes another substance. The oxidation state, which describes the degree of loss of electrons, of the oxidizer decreases while that of the reductant increases; this is expressed by saying that oxidizers "undergo reduction" and "are reduced" while reducers "undergo oxidation" and "are oxidized". Common oxidizing agents are oxygen, hydrogen peroxide and the halogens. In one sense, an oxidizing agent is a chemical species that undergoes a chemical reaction in which it gains one or more electrons. In that sense, it is one component in an oxidation–reduction (redox) reaction. In the second sense, an oxidizing agent is a chemical species that transfers electronegative atoms, usually oxygen, to a substrate. Co ...
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NFPA 704
"NFPA 704: Standard System for the Identification of the Hazards of Materials for Emergency Response" is a standard maintained by the U.S.-based National Fire Protection Association. First "tentatively adopted as a guide" in 1960, and revised several times since then, it defines the colloquial "Safety Square" or "Fire Diamond" which is used by emergency personnel to quickly and easily identify the risks posed by hazardous materials. This helps determine what, if any, special equipment should be used, procedures followed, or precautions taken during the initial stages of an emergency response. It is an internationally accepted safety standard, and is crucial while transporting chemicals. Codes The four divisions are typically color-coded with red on top indicating flammability, blue on the left indicating level of health hazard, yellow on the right for chemical reactivity, and white containing codes for special hazards. Each of health, flammability and reactivity is rated on a ...
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US Department Of Transportation
The United States Department of Transportation (USDOT or DOT) is one of the executive departments of the U.S. federal government. It is headed by the secretary of transportation, who reports directly to the President of the United States and is a member of the president's Cabinet. The department's mission is "to develop and coordinate policies that will provide an efficient and economical national transportation system, with due regard for need, the environment, and the national defense." History Prior to the creation of the Department of Transportation, its functions were administered by the under secretary of commerce for transportation. In 1965, Najeeb Halaby, administrator of the Federal Aviation Agency (predecessor to the Federal Aviation Administration, FAA), suggested to President Lyndon B. Johnson that transportation be elevated to a cabinet-level post, and that the FAA be folded into the DOT. It was established by Congress in the Department of Transportatio ...
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Auto-oxidation
Autoxidation (sometimes auto-oxidation) refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the gradual degradation of organic compounds in air at ambient temperatures. Many common phenomena can be attributed to autoxidation, such as food going rancid, the 'drying' of varnishes and paints, and the perishing of rubber. It is also an important concept in both industrial chemistry and biology. Autoxidation is therefore a fairly broad term and can encompass examples of photooxygenation and catalytic oxidation. The common mechanism is a free radical chain reaction, where the addition of oxygen gives rise to hydroperoxides and their associated peroxy radicals (ROO•). Typically, an induction period is seen at the start where there is little activity; this is followed by a gradually accelerating take-up of oxygen, giving an autocatalytic reaction which can only be ...
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Oxidation
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a decrease in the oxidation state. There are two classes of redox reactions: * ''Electron-transfer'' – Only one (usually) electron flows from the reducing agent to the oxidant. This type of redox reaction is often discussed in terms of redox couples and electrode potentials. * ''Atom transfer'' – An atom transfers from one substrate to another. For example, in the rusting of iron, the oxidation state of iron atoms increases as the iron converts to an oxide, and simultaneously the oxidation state of oxygen decreases as it accepts electrons released by the iron. Although oxidation reactions are commonly associated with the formation of oxides, other chemical species can serve the same function. In hydrogenation, C=C (and other) bonds a ...
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Sharpless Epoxidation
The Sharpless epoxidation reaction is an enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary allylic alcohols. The oxidizing agent is ''tert''-butyl hydroperoxide. The method relies on a catalyst formed from titanium tetra(isopropoxide) and diethyl tartrate. 2,3-Epoxyalcohols can be converted into diols, aminoalcohols, and ethers. The reactants for the Sharpless epoxidation are commercially available and relatively inexpensive. K. Barry Sharpless was awarded the 2001 Nobel Prize in Chemistry for this and related work on asymmetric oxidations. The prize was shared with William S. Knowles and Ryōji Noyori. Catalyst 5–10 mol% of the catalyst is typical. The presence of 3Å molecular sieves (3Å MS) is necessary. The structure of the catalyst is uncertain although it is thought to be a dimer of []. Selectivity The epoxidation of allylic alcohols is a well-utilized conversion in fine chemical synthesis. The chirality of the produc ...
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MTBE
Methyl ''tertiary''-butyl ether (MTBE), also known as methyl tert-butyl ether and ''tert''-butyl methyl ether, is an organic compound with a structural formula (CH3)3COCH3. MTBE is a volatile, flammable, and colorless liquid that is sparingly soluble in water. Primarily used as a fuel additive, MTBE is blended into gasoline to increase its octane rating and knock resistance, and reduce unwanted emissions. Production and properties MTBE is manufactured via the chemical reaction of methanol and isobutylene. Methanol is primarily derived from natural gas, where steam reforming converts the various light hydrocarbons in natural gas (primarily methane) into carbon monoxide and hydrogen. The resulting gases then further react in the presence of a catalyst to form methanol. Isobutylene can be produced through a variety of methods. One process the isomerization of ''n''-butane into isobutane, which then undergoes dehydrogenation to form the isobutylene. In the Halcon process, t-Butyl ...
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