Isethionic acid | |
Names | |
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Preferred IUPAC name 2-Hydroxyethane-1-sulfonic acid | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.003.169 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C2H6O4S | |
Molar mass | 126.13 g/mol |
Density | 1.63 g/cm3 |
Acidity (pKa) | 1.39 (predicted) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isethionic acid is an organosulfur compound containing an alkyl sulfonic acid located beta to a hydroxy group. Its discovery is generally attributed to Heinrich Gustav Magnus, who prepared it by the action of solid sulfur trioxide on ethanol in 1833. [1] It is a white water-soluble solid used in the manufacture of certain surfactants and in the industrial production of taurine. It is most commonly available in the form of its sodium salt (sodium isethionate).
The original synthesis of the compound, involving the reaction of sulfur trioxide with ethanol, has largely been replaced by more advanced methods. An alternative production method involves the hydrolysis of carbyl sulfate, which is derived from the sulfonation of ethylene.
However the most common route is the reaction of ethylene oxide with aqueous sodium bisulfite, which produces the sodium salt (sodium isethionate):
Isethionic acid is used as a starting material in the industrial production of taurine.
Dehydration of isethionic acid gives vinylsulfonic acid. [2]
Fatty acid esters of isethionic acid (such as sodium lauroyl isethionate and sodium cocoyl isethionate) are used as biodegradable anionic surfactants. [3] These materials are much milder to skin that other sulfate based surfactants (i.e. sodium lauryl sulfate) [4] making them popular for use in make-up, shampoos and detergent bars including those made by Dove.
Isethionic acid is also used as a counter ion in certain pharmaceutical formulations, including the antimicrobials hexamidine and pentamidine. [5]
Studies made on dog heart slices suggested that heart tissue may be capable of converting taurine to isethionic acid, further experiments demonstrated that this tissue may synthesize taurine from cystine. [6]
Sodium laureth sulfate (SLES), an accepted contraction of sodium lauryl ether sulfate (SLES), also called sodium alkylethersulfate, is an anionic detergent and surfactant found in many personal care products and for industrial uses. SLES is an inexpensive and very effective foaming agent. SLES, sodium lauryl sulfate (SLS), ammonium lauryl sulfate (ALS), and sodium pareth sulfate are surfactants that are used in many cosmetic products for their cleaning and emulsifying properties. It is derived from palm kernel oil or coconut oil. In herbicides, it is used as a surfactant to improve absorption of the herbicidal chemicals and reduces time the product takes to be rainfast, when enough of the herbicidal agent will be absorbed.
Sodium dodecyl sulfate (SDS) or sodium lauryl sulfate (SLS), sometimes written sodium laurilsulfate, is an organic compound with the formula CH3(CH2)11OSO3Na and structure H3C−(CH2)11−O−S(=O)2−O−Na+. It is an anionic surfactant used in many cleaning and hygiene products. This compound is the sodium salt of the 12-carbon organosulfate. Its hydrocarbon tail combined with a polar "headgroup" give the compound amphiphilic properties that make it useful as a detergent. SDS is also component of mixtures produced from inexpensive coconut and palm oils. SDS is a common component of many domestic cleaning, personal hygiene and cosmetic, pharmaceutical, and food products, as well as of industrial and commercial cleaning and product formulations.
A detergent is a surfactant or a mixture of surfactants with cleansing properties when in dilute solutions. There are a large variety of detergents, a common family being the alkylbenzene sulfonates, which are soap-like compounds that are more soluble in hard water, because the polar sulfonate is less likely than the polar carboxylate to bind to calcium and other ions found in hard water.
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 in 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.
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, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.
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.
Dodecanol, or lauryl alcohol, is an organic compound produced industrially from palm kernel oil or coconut oil. It is a fatty alcohol. Sulfate esters of lauryl alcohol, especially sodium lauryl sulfate, are very widely used as surfactants. Sodium lauryl sulfate and the related dodecanol derivatives ammonium lauryl sulfate and sodium laureth sulfate are all used in shampoos. Dodecanol is tasteless, colorless, and has a floral odor.
Laundry detergent is a type of detergent used for cleaning dirty laundry (clothes). Laundry detergent is manufactured in powder and liquid form.
Sulfation is the chemical reaction that entails the addition of SO3 group. In principle, many sulfations would involve reactions of sulfur trioxide (SO3). In practice, most sulfations are effected less directly. Regardless of the mechanism, the installation of a sulfate-like group on a substrate leads to substantial changes.
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.
Sodium tetradecyl sulfate (STS) is a common anionic surfactant. The compound consists of the sodium salt of the micelle-forming sulfate ester of tetradecanol. It is a white, water-soluble solid of low toxicity with many practical uses.
Cleaning agents or hard-surface cleaners are substances used to remove dirt, including dust, stains, foul odors, and clutter on surfaces. Purposes of cleaning agents include health, beauty, removing offensive odors, and avoiding the spread of dirt and contaminants to oneself and others. Some cleaning agents can kill bacteria and clean at the same time. Others, called degreasers, contain organic solvents to help dissolve oils and fats.
1,3-Propane sultone is the organosulfur compound with the formula (CH2)3SO3. It is a cyclic sulfonate ester, a class of compounds called sultones. It is a readily melting colorless solid.
In chemistry, disulfate or pyrosulfate is the anion with the molecular formula S
2O2−
7. Disulfate is the IUPAC name. It has a dichromate-like structure and can be visualised as two corner-sharing SO4 tetrahedra, with a bridging oxygen atom. In this anion, sulfur has an oxidation state of +6. Disulfate is the conjugate base of the hydrogen disulfate (hydrogen pyrosulfate) ion HS
2O−
7, which in turn is the conjugate base of disulfuric acid (pyrosulfuric acid).
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.
Carbyl sulfate is an organosulfur compound. The white solid is the product of the reaction of sulfur trioxide and ethylene. It is used in preparation of some dyes and other organosulfur compounds. Carbyl sulfate is a colorless, crystalline, hygroscopic substance although commercial product can appear as a liquid. Because of its unpleasant properties carbyl sulfate is difficult to handle and is usually not isolated but further processed to give secondary products.
Taurates (or taurides) are a group of mild anionic surfactants. They are composed of a hydrophilic head group, consisting of N-methyltaurine (2-methylaminoethanesulfonic acid) and a lipophilic residue, consisting of a long-chain carboxylic acid (fatty acid), both linked via an amide bond. The fatty acids used could be lauric (C12), myristic (C14), palmitic (C16) or stearic acid (C18), but mainly mixtures of oleic acid (C18:1) and coconut fatty acid (C8 – C18) are used. Besides sodium, no other counterions play a relevant role (these could be e. g. ammonium or other alkali or alkaline earth metals).
N-Methyltaurine is an aminosulfonic acid which is present as a zwitterion in the crystalline state and in polar solvents. In contrast to the widespread taurine, N-methyltaurine has been found in nature only in red algae, where it is formed by methylation of taurine. It is suitable for esterification with long-chain carboxylic acids to taurides (acylaminoethansulfonaten) because of its high polarity and the relatively good solubility of its alkaline earth metal salts, which are also used as mild anionic surfactants.
α-Olefin sulfonates are a group of anionic surfactants, which are used as detergents. The compounds contain a - mostly linear, primary - alkyl R and a monovalent cation M, preferably sodium. The most frequently used example of this group of substances is sodium α-olefin sulfonate.