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. [1] Some members of this group of compounds have proven controversial. [2] .
The long-chain alkylphenols are prepared by alkylation of phenol with alkenes:
In this way, about 500M kg/y are produced. Alkylphenols ethoxylates are common surfactants. Long-chain alkylphenols are used extensively as precursors to detergents. By condensation with formaldehyde, some alkylphenols are components in phenolic resins. [1] These compounds are also used as building-block chemicals in making fragrances, thermoplastic elastomers, antioxidants, oil field chemicals, and fire retardant materials. As plastizers and antioxidants, alkylphenols are also found in tires, adhesives, coatings, carbonless copy paper and high performance rubber products.
Alkylphenols are xenoestrogens. [3] Long chain Alkylphenols have the most potent estrogenic activity. [3] 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 slower approach to make sure that action is based on sound science. [4] [5]
Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word "surfactant" is a blend of surface-active agent, coined c. 1950. As they consist of a water-repellent and a water-attracting part, they enable water and oil to mix; they can form foam and facilitate the detachment of dirt.
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.
Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region of 10 million tonnes.
In organic chemistry, ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates.
In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.
Nonylphenols are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. Nonylphenols can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers. They are used extensively in epoxy formulation in North America but its use has been phased out in Europe. These compounds are also precursors to the commercially important non-ionic surfactants alkylphenol ethoxylates and nonylphenol ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. Nonylphenol has attracted attention due to its prevalence in the environment and its potential role as an endocrine disruptor and xenoestrogen, due to its ability to act with estrogen-like activity. The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain. Nonylphenol has been found to act as an agonist of the GPER (GPR30).
Fatty alcohols (or long-chain alcohols) are usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils. The precise chain length varies with the source. Some commercially important fatty alcohols are lauryl, stearyl, and oleyl alcohols. They are colourless oily liquids (for smaller carbon numbers) or waxy solids, although impure samples may appear yellow. Fatty alcohols usually have an even number of carbon atoms and a single alcohol group (–OH) attached to the terminal carbon. Some are unsaturated and some are branched. They are widely used in industry. As with fatty acids, they are often referred to generically by the number of carbon atoms in the molecule, such as "a C12 alcohol", that is an alcohol having 12 carbons, for example dodecanol.
Xenoestrogens are a type of xenohormone that imitates estrogen. They can be either synthetic or natural chemical compounds. Synthetic xenoestrogens include some widely used industrial compounds, such as PCBs, BPA, and phthalates, which have estrogenic effects on a living organism even though they differ chemically from the estrogenic substances produced internally by the endocrine system of any organism. Natural xenoestrogens include phytoestrogens which are plant-derived xenoestrogens. Because the primary route of exposure to these compounds is by consumption of phytoestrogenic plants, they are sometimes called "dietary estrogens". Mycoestrogens, estrogenic substances from fungi, are another type of xenoestrogen that are also considered mycotoxins.
Triton X-100 is a nonionic surfactant that has a hydrophilic polyethylene oxide chain and an aromatic hydrocarbon lipophilic or hydrophobic group. The hydrocarbon group is a 4-(1,1,3,3-tetramethylbutyl)-phenyl group. Triton X-100 is closely related to IGEPAL CA-630, which might differ from it mainly in having slightly shorter ethylene oxide chains. As a result, Triton X-100 is slightly more hydrophilic than Igepal CA-630 thus these two detergents may not be considered functionally interchangeable for most applications.
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.
Polyethoxylated tallow amine refers to a range of non-ionic surfactants derived from animal fats (tallow). They are a class of polyethoxylated amines (POEAs). The abbreviation 'POEA' is often erroneously used to refer to POE-tallowamine. They are used primarily as emulsifiers and wetting agents for agrochemical formulations, such as pesticides and herbicides.
In ground deicing of aircraft, aircraft deicing fluid (ADF), aircraft deicer and anti-icer fluid (ADAF) or aircraft anti-icing fluid (AAF) are commonly used for both commercial and general aviation. Environmental concerns include increased salinity of groundwater where de-icing fluids are discharged into soil, and toxicity to humans and other mammals.
In organosulfur chemistry, organosulfates are a class of organic compounds sharing a common functional group with the structure R−O−SO−3. The SO4 core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols and sulfuric acid although many are not prepared in this way. Many sulfate esters are used in detergents, and some are useful reagents. Alkyl sulfates consist of a hydrophobic hydrocarbon chain, a polar sulfate group and either a cation or amine to neutralize the sulfate group. Examples include: sodium lauryl sulfate and related potassium and ammonium salts.
NP-40 is a commercially available detergent with CAS Registry Number 9016-45-9. NP-40 is an ethoxylated nonylphenol for non-ionic surfactants and can act as emulsifier and demulsifier agent.
Nonoxynols also known as nonaethylene glycol or polyethylene glycol nonyl phenyl ether are mixtures of nonionic surfactants used as detergents, emulsifiers, wetting agents or defoaming agents. The most commonly discussed compound nonoxynol-9 is a spermicide, formulated primarily as a component of vaginal foams and creams. Nonoxynol was found to metabolize into free nonylphenol when administered to lab animals. Arkopal-N60, with on average 6 ethylene glycol units is a related used surfactant.
Walter Giger is a Swiss chemist. He had been working at the Swiss Federal Institute of Aquatic Science and Technology (Eawag), where he was the head of the division Chemische Problemstoffe. He has been a professor for environmental chemistry at the ETH Zurich since 1995.
Environmental impacts of cleaning products entail the consequences that come as a result of chemical compounds in cleaning products. These cleaning products can contain chemicals that have detrimental impacts on the environment or on people.
Paint has four major components: pigments, binders, solvents, and additives. Pigments serve to give paint its color, texture, toughness, as well as determining if a paint is opaque or not. Common white pigments include titanium dioxide and zinc oxide. Binders are the film forming component of a paint as it dries and affects the durability, gloss, and flexibility of the coating. Polyurethanes, polyesters, and acrylics are all examples of common binders. The solvent is the medium in which all other components of the paint are dissolved and evaporates away as the paint dries and cures. The solvent also modifies the curing rate and viscosity of the paint in its liquid state. There are two types of paint: solvent-borne and water-borne paints. Solvent-borne paints use organic solvents as the primary vehicle carrying the solid components in a paint formulation, whereas water-borne paints use water as the continuous medium. The additives that are incorporated into paints are a wide range of things which impart important effects on the properties of the paint and the final coating. Common paint additives are catalysts, thickeners, stabilizers, emulsifiers, texturizers, biocides to fight bacterial growth, etc.
Alkylbenzene sulfonates are a class of anionic surfactants, consisting of a hydrophilic sulfonate head-group and a hydrophobic alkylbenzene tail-group. Along with sodium laureth sulfate, they are one of the oldest and most widely used synthetic detergents and may be found in numerous personal-care products and household-care products . They were introduced in the 1930s in the form of branched alkylbenzene sulfonates (BAS). However following environmental concerns these were replaced with linear alkylbenzene sulfonates (LAS) during the 1960s. Since then production has increased significantly from about one million tons in 1980, to around 3.5 million tons in 2016, making them most produced anionic surfactant after soaps.
2,4,6-Tri-tert-butylphenol (2,4,6-TTBP) is a phenol symmetrically substituted with three tert-butyl groups and thus strongly sterically hindered. 2,4,6-TTBP is a readily oxidizable aromatic compound and a weak acid. It oxidizes to give the deep-blue 2,4,6-tri-tert-butylphenoxy radical. 2,4,6-TTBP is related to 2,6-di-tert-butylphenol, which is widely used as an antioxidant in industrial applications. These compounds are colorless solids.
{{cite web}}: CS1 maint: multiple names: authors list (link)