fatty alcohols which have been 'capped' with ~1 propylene oxide unit are extensively marketed as defoamers. Ethoxysulfates Ethoxylated fatty alcohols are often converted to the corresponding organosulfates, which can be easily deprotonated to give anionic surfactants such as sodium laureth sulfate. Being salts, ethoxysulfates exhibit good water solubility (high HLB value). The conversion is achieved by treating ethoxylated alcohols with sulfur trioxide. Laboratory scale synthesis may be performed using chlorosulfuric acid: R(OC2H4)nOH + SO3 → R(OC2H4)nOSO3H R(OC2H4)nOH + HSO3Cl → R(OC2H4)nOSO3H + HCl The resulting sulfate esters are neutralized to give the salt: R(OC2H4)nOSO3H + NaOH → R(OC2H4)nOSO3Na + H2O Small volumes are neutralized with alkanolamines such as triethanolamine (TEA). In 2008, 381,000 metric tons of alcohol ethoxysulfates were consumed in North America. Other materials Although alcohols are by far the major substrate for ethoxylation, many nucleophiles are reactive toward ethylene oxide. Primary amines will react to give di-chain materials such as polyethoxylated tallow amine. The reaction of ammonia produces important bulk chemicals such as ethanolamine, diethanolamine, and triethanolamine. Applications of ethoxylated products Alcohol ethoxylates (AE) and alcohol ethoxysulfates (AES) are surfactants found in products such as laundry detergents, surface cleaners, cosmetics, agricultural products, textiles, and paint. Alcohol ethoxylates As alcohol ethoxylate based surfactants are non-ionic they typically require longer ethoxylate chains than their sulfonated analogues in order to be water-soluble. Examples synthesized on an industrial scale include octyl phenol ethoxylate, polysorbate 80 and poloxamers. Ethoxylation is commonly practiced, albeit on a much smaller scale, in the biotechnology and pharmaceutical industries to increase water solubility and, in the case of pharmaceuticals, circulatory half-life of non-polar organic compounds. In this application, ethoxylation is known as "PEGylation" (polyethylene oxide is synonymous with polyethylene glycol, abbreviated as PEG). Carbon chain length is 8-18 while the ethoxylated chain is usually 3 to 12 ethylene oxides long in home products. They feature both lipophilic tails, indicated by the alkyl group abbreviation, R, and relatively polar headgroups, represented by the formula (OC2H4)nOH. Alcohol ethoxysulfates AES found in consumer products generally are linear alcohols, which could be mixtures of entirely linear alkyl chains or of both linear and mono-branched alkyl chains. A high-volume example of these is sodium laureth sulfate a foaming agent in shampoos and liquid soaps, as well as industrial detergents. Environmental and safety Alcohol ethoxylates (AEs) Human health Alcohol ethoxylates are not observed to be mutagenic, carcinogenic, or skin sensitizers, nor cause reproductive or