2,6-di-tert-butylphenol
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2,6-di-tert-butylphenol
2,6-Di-''tert''-butylphenol is an organic compound with the structural formula 2,6-((CH3)3C)2C6H3OH. This colorless solid alkylated phenol and its derivatives are used industrially as UV stabilizers and antioxidants for hydrocarbon-based products ranging from petrochemicals to plastics. Illustrative of its usefulness, it prevents gumming in aviation fuels. Production 2,6-Di-''tert''-butylphenol is prepared industrially via the Friedel–Crafts alkylation of phenol with isobutene catalyzed by aluminium phenoxide: :C6H5OH + 2 CH2=C(CH3)2 → ((CH3)3C)2C6H3OH In this way, approximately 2.5M kg/y are produced. Applications Its dominant use is as an antioxidant. 2,6-di-''tert''-butylphenol is a precursor to more complex compounds used as antioxidants and light-protection agents for the stabilization for polymers. Of particular note is methyl-3-(3,5-di-''tert''-butyl-4-hydroxyphenyl)-propionate (CAS# 6386-38-5), which is formed by the Michael addition of methyl methac ...
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Antioxidant
Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. This can lead to polymerization and other chain reactions. They are frequently added to industrial products, such as fuels and lubricants, to prevent oxidation, and to foods to prevent spoilage, in particular the rancidification of oils and fats. In cells, antioxidants such as glutathione, mycothiol or bacillithiol, and enzyme systems like superoxide dismutase, can prevent damage from oxidative stress. The only dietary antioxidants are vitamins A, C, and E, but the term ''antioxidant'' has also been applied to numerous other dietary compounds that only have antioxidant properties in vitro, with little evidence for antioxidant properties in vivo. Dietary supplements marketed as antioxidants have not been shown to maintain health or prevent disease in humans. History As part of their adaptation from marine life, terrestrial plants began producing non-marine a ...
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Antioxidants
Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. This can lead to polymerization and other chain reactions. They are frequently added to industrial products, such as fuels and lubricants, to prevent oxidation, and to foods to prevent spoilage, in particular the rancidification of oils and fats. In cells, antioxidants such as glutathione, mycothiol or bacillithiol, and enzyme systems like superoxide dismutase, can prevent damage from oxidative stress. The only dietary antioxidants are vitamins A, C, and E, but the term ''antioxidant'' has also been applied to numerous other dietary compounds that only have antioxidant properties in vitro, with little evidence for antioxidant properties in vivo. Dietary supplements marketed as antioxidants have not been shown to maintain health or prevent disease in humans. History As part of their adaptation from marine life, terrestrial plants began producing non-marine antioxida ...
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Butylated Hydroxytoluene
Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids (e.g. fuels, oils) and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be " generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an antiviral drug, but as of December 2022 , use of BHT as a drug is not supported by the scientific literature and it has not been approved by any drug regulatory agency for use as an antiviral. Natural occurrence Phytoplankton, including the green algae '' Botryococcus braunii'', as well as three different cyanobacter ...
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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. Liv ...
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Irganox 1098
Irganox 1098 is the trade name for ''N'',''N''′-(hexane-1,6-diyl)bis -(3,5-di-''tert''-butyl-4-hydroxyphenyl)propanamide'', a primary antioxidant manufactured by BASF primarily used for stabilizing polymers, especially polyamide A polyamide is a polymer with repeating units linked by amide bonds. Polyamides occur both naturally and artificially. Examples of naturally occurring polyamides are proteins, such as wool and silk. Artificially made polyamides can be made through ...s. It is noted for its thermal stability as well as its non-discoloring properties. See also * Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) References Phenol antioxidants {{polymer-stub ...
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Alkylphenols
Alkylphenols are a family of organic compounds obtained by the alkylation of phenols. The term is usually reserved for commercially important propylphenol, butylphenol, amylphenol, heptylphenol, octylphenol, nonylphenol, dodecylphenol and related "long chain alkylphenols" (LCAPs). Methylphenols and ethylphenols are also alkylphenols, but they are more commonly referred to by their specific names, cresols and xylenols. Production The long-chain alkylphenols are prepared by alkylation of phenol with alkenes: :C6H5OH + RR'C=CHR" → RR'CH−CHR"−C6H4OH In this way, about 500M kg/y are produced. Environmental controversy over nonylphenols Alkylphenols are xenoestrogens. Long chain Alkylphenols have the most potent estrogenic activity. The European Union has implemented sales and use restrictions on certain applications in which nonylphenols are used because of their alleged "toxicity, persistence, and the liability to bioaccumulate" but the United States EPA has taken a ...
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Para Tertiary Butyl Phenol
4-''tert''-Butylphenol is an organic compound with the formula (CH3)3CC6H4OH. It is one of three isomeric ''tert''-butyl phenols. It is a white solid with a distinct phenolic odor. It dissolves in basic water. Manufacture It can be prepared by acid-catalyzed alkylation of phenol with isobutene, 2-''tert''-butylphenol being the major side product. It can be produced by diverse transalkylation reactions. Uses It major uses are in the production of epoxy resins and curing agents and also in polycarbonate resins. It has also found use in the production of phenolic resins. Another use is in the production of para tertiary butylphenol formaldehyde resin. It has also found use as a plasticizer. Bisphenol A is difunctional and used to produce epoxy resin and polycarbonate. 4-''tert''-Butylphenol is monofunctional and so in polymer science terms, bisphenol A is a polymer chain extender but 4-''tert''-butylphenol is a chain stopper or sometimes called endcapper. It is thus use to ...
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2,4-Dimethyl-6-tert-butylphenol
2,4-Dimethyl-6-''tert''-butylphenol is the organic compound with the formula Me2(''tert''-Bu)C6H2OH (Me = methyl, ''tert''-Bu = tertiary butyl). It is a colorless oil that is classified as an alkylated phenol. Preparation, reactions, uses It is used as an antioxidant, e.g. to prevent gumming in fuels, and as an ultraviolet stabilizer. It is used in jet fuels, gasolines, and avgas. It is prepared by alkylation of xylenol with isobutylene. This alkylation provides a means to separate 2,4-xylenol from 2,5-xylenol since 2,4-dimethyl-6-tert-butylphenol is insoluble in 10% NaOH but 2,5-dimethyl-6-tert-butylphenol is soluble. Subsequent to separation, the tert-butyl group can be removed in strong acid. Tradenames One of its trade names is Topanol A. It is found in antioxidant mixtures AO-30, AO-31, AO-32, IONOL K72, IONOL K78, IONOL K98, and others. See also * 2,6-Di-''tert''-butylphenol *Butylated hydroxytoluene * Propofol (Structural isomer) *List of gasoline additives ...
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Probucol
Probucol, sold under the trade name Lorelco among others, is an anti- hyperlipidemic drug initially developed for the treatment of coronary artery disease. Clinical development was discontinued after it was found that the drug may have the undesired effect of lowering HDL in patients with a previous history of heart disease. It may also cause QT interval prolongation. Probucol was initially developed in the 1970s by a chemical company to maximize airplane tire longevity. Mechanism of action Probucol lowers the level of cholesterol in the bloodstream by increasing the rate of LDL catabolism. Additionally, probucol may inhibit cholesterol synthesis and delay cholesterol absorption. Probucol is a powerful antioxidant which inhibits the oxidation of cholesterol in LDLs; this slows the formation of foam cells, which form atherosclerotic plaques. After promising test results in mouse models, Probucol is under study at Weston Brain Institute of McGill University as a possible aid ...
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CGP-7930
CGP-7930 is a compound used in scientific research which acts as a positive allosteric modulator at the GABAB receptor. It has anxiolytic effects in animal studies, and has a synergistic effect with GABAB agonists such as baclofen and GHB, as well as reducing self-administration of alcoholic drinks and cocaine Cocaine (from , from , ultimately from Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly used recreationally for its euphoric effects. It is primarily obtained from the leaves of two Coca species native to South Am .... References {{GABAergics Phenols Secondary alcohols GABAB receptor positive allosteric modulators Tert-butyl compounds ...
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Methyl Methacrylate
Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA). Production and properties Given the scale of production, many methods have been developed starting from diverse two- to four-carbon precursors.. Two principal routes appear to be commonly practiced. Cyanohydrin route The compound is manufactured by several methods, the principal one being the acetone cyanohydrin (ACH) route. ACH is produced by condensation of acetone and hydrogen cyanide. The cyanohydrin is hydrolyzed in the presence of sulfuric acid to a sulfate ester of the methacrylamide. Methanolysis of this ester gives ammonium bisulfate and MMA. Although widely used, the ACH route coproduces substantial amounts of ammonium sulfate. :(CH3)2CO + HCN → (CH3)2C(OH)CN :(CH3)2C(OH)CN + H2SO4 → (CH3)2C(OSO3H)C(O)NH ...
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